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WO2025217091A1 - Substances odorantes pour fluides, fluides odorants, procédés et systèmes - Google Patents

Substances odorantes pour fluides, fluides odorants, procédés et systèmes

Info

Publication number
WO2025217091A1
WO2025217091A1 PCT/US2025/023542 US2025023542W WO2025217091A1 WO 2025217091 A1 WO2025217091 A1 WO 2025217091A1 US 2025023542 W US2025023542 W US 2025023542W WO 2025217091 A1 WO2025217091 A1 WO 2025217091A1
Authority
WO
WIPO (PCT)
Prior art keywords
odorant
ppmw
fluid
composition
odorized
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2025/023542
Other languages
English (en)
Inventor
Nicolas Blouin
Jasper SMETS
Brooke L. Small
Chad W. Brown
Christophe Laroche
Kristof DOX
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chevron Phillips Chemical Co LP
Original Assignee
Chevron Phillips Chemical Co LP
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chevron Phillips Chemical Co LP filed Critical Chevron Phillips Chemical Co LP
Publication of WO2025217091A1 publication Critical patent/WO2025217091A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
    • C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
    • C10L3/10—Working-up natural gas or synthetic natural gas
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/16—Hydrocarbons
    • C10L1/1608—Well defined compounds, e.g. hexane, benzene
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/02—Inorganic or organic compounds containing atoms other than C, H or O, e.g. organic compounds containing heteroatoms or metal organic complexes
    • C10L2200/0277—Hydrogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/08—Inhibitors
    • C10L2230/081—Anti-oxidants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/10—Function and purpose of a components of a fuel or the composition as a whole for adding an odor to the fuel or combustion products
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/14—Function and purpose of a components of a fuel or the composition as a whole for improving storage or transport of the fuel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L2270/00—Specifically adapted fuels
    • C10L2270/06—Specifically adapted fuels for fuel cells

Definitions

  • This disclosure relates to odorants for fluids, such as fuel gases, odorized fluids, and methods for odorizing fluids, such as fuel gases.
  • Odorants have been added to fluids, including various dangerous gases, for decades. Odorants can allow for the detection of a leak without external equipment. Odorants can also allow for leak detection in locations where it can be difficult or impossible to place detectors, such as outdoor locations. Since odorants that are easily detectable by the human olfactory system can be used, small fluid leaks can be easily detected.
  • Sulfur compounds that are commonly used as odorizing agents include tetrahydrothiophene, /c77-butylmcrcaptan, dimethyl sulfide, and ethyl mercaptan.
  • Fuel gases that do not have sufficient intrinsic odor are usually mixed with compounds having an intense smell, e.g., an odorant, so that leaks can be easily perceived.
  • odorants that are added to fuel gases ideally should have a perceptible odor in a number of circumstances, such as high dilution, and cause an alarm association in humans due to an unpleasant odor.
  • Hydrogen is an odorless and hazardous gas. Hydrogen gas has a very low density, which allows it to disperse and mix readily with air, thereby creating explosion or ignition hazards. A hydrogen molecule also is very small and typically has a high diffusion coefficient in other gases and solids. When considering hydrogen leaks, its high buoyancy generally affects gas motion considerably more than its high diffusivity. Hydrogen typically has a flow rate that is about 25% higher than methane through an identical leak and with the same associated pressure drop. The minimum ignition energy of hydrogen is very low, e.g., lower than natural gas. For one or more of these reasons, the odorization of hydrogen should increase the safety of its use, especially as a fuel gas.
  • a promising application for hydrogen includes hydrogen powered fuel cells.
  • Hydrogen fuel cells typically use a catalyst comprising a precious metal to oxidize hydrogen electrochemically at the anode of a cell. If the active sites of the precious metal catalyst are occupied by a molecule other than hydrogen, the activity of the catalyst, and hence the efficiency and performance of the fuel cell, can decrease dramatically.
  • odorants are provided, such as odorants for a fluid, which can include a gas.
  • the gas can be a fuel gas.
  • the odorants include a hexyne, a heptyne, an octyne, or a combination thereof.
  • the hexyne can include a 1 -hexyne, a 2-hexyne, or a combination thereof.
  • the heptyne can include a 2-heptyne, a 3 -heptyne, or a combination thereof.
  • the octyne can include a 3 -octyne, a 4-octyne, or a combination thereof.
  • embodiments of the odorants provided herein such as the 2-/3-heptynes and 3-/4-octynes, surprisingly have a lower odor detection threshold than 1 -heptyne and 1 -octyne, and/or an alarming odor profile compared to 1- heptyne and 1 -octyne.
  • odorants provided herein, such as the 2-/3-heptynes and 3-/4-octynes, surprisingly have a lower odor detection threshold than 1 -heptyne and 1 -octyne, and/or an alarming odor profile compared to 1- heptyne and 1 -octyne.
  • One or both of these features can provide one or more significant safety advantages.
  • odorant compositions are provided.
  • the odorant compositions include an odorant and an additive.
  • the additive can include an odiferous compound, a stabilizer, a diluent, or a combination thereof.
  • methods of odorizing a fluid include providing a fluid, and contacting the (i) fluid, such as a gas, and (ii) an odorant or an odorant composition to form an odorized fluid, such as any of those provided herein.
  • methods of generating energy include providing a fuel cell that includes an anode; and contacting the anode and an odorized fluid as provided herein.
  • the contacting of the anode and the odorized fluid can produce an oxidized odorized fluid.
  • the methods also can include removing the odorant from the odorized fluid, the oxidized odorized fluid, or both the odorized fluid and the oxidized odorized fluid.
  • systems include (i) a sensor, and (ii) an odorant or an odorant composition provided herein.
  • a sensor can be configured to permit the use of any of the odorants provided herein at a concentration that is not detectable by an average human.
  • FIG. 1 depicts the results of a durability test of an embodiment of a protonexchange membrane fuel cell (PEMFC) using hept-2-yne as a hydrogen odorant.
  • PEMFC protonexchange membrane fuel cell
  • FIG. 2 depicts the results of a durability test of an embodiment of a PEMFC using hept-3-yne as a hydrogen odorant.
  • FIG. 3 depicts the results of a durability test of an embodiment of a PEMFC using oct-4-yne as a hydrogen odorant.
  • FIG. 4 depicts the results of a durability test of an embodiment of a PEMFC using l-hexen-5-yne as a hydrogen odorant.
  • FIG. 5 depicts the results of a durability test of an embodiment of a PEMFC using hept-l-en-6-yne as a hydrogen odorant.
  • FIG. 6 depicts the results of a durability test of an embodiment of a PEMFC using 3,3-dimethyl-but-l-yne as a hydrogen odorant.
  • FIG. 7 depicts the results of a durability test of an embodiment of a PEMFC using hex-l-yne as a hydrogen odorant.
  • FIG. 8 depicts the results of a durability test of an embodiment of a PEMFC using hex-2-yne as a hydrogen odorant.
  • FIG. 9 depicts the results of a durability test of an embodiment of a PEMFC using butyraldehyde as a hydrogen odorant.
  • FIG. 10 depicts the results of a durability test of an embodiment of a PEMFC using tetrahydrothiophene (THT) as a hydrogen odorant.
  • compositions and methods are described in terms of “comprising” various components or steps, the compositions and methods can also “consist essentially of’ or “consist of’ the various components or steps, unless stated otherwise.
  • Applicant’s intent is to recite individually 5 mg/m 3 n, 6 mg/m 3 n, 7 mg/m 3 n, 8 mg/m 3 n, 9 mg/m 3 n, 10 mg/m 3 n, 11 mg/m 3 n, 12 mg/m 3 n, 13 mg/m 3 n, 14 mg/m 3 n, 15 mg/m 3 n, 16 mg/m 3 n, 17 mg/m 3 n, 18 mg/m 3 n, 19 mg/m 3 n, and 20 mg/m 3 n, including any sub-ranges and combinations of sub-ranges encompassed therein, and these methods of describing such ranges are interchangeable.
  • Values or ranges may be expressed herein as “about,” from “about” one particular value, and/or to “about” another particular value. When such values or ranges are expressed, other embodiments disclosed include the specific value recited, from the one particular value, and/or to the other particular value. Similarly, when values are expressed as approximations, by use of the antecedent “about,” it will be understood that the particular value forms another embodiment. It will be further understood that there are a number of values disclosed therein, and that each value is also herein disclosed as “about” that particular value in addition to the value itself. In another aspect, each use of the term “about” can, independently, mean +20% of the stated value, ⁇ 15% of the stated value, ⁇ 10% of the stated value, ⁇ 5% of the stated value, or ⁇ 3% of the stated value.
  • any name or structure (general or specific) presented is intended to encompass all conformational isomers, regioisomers, stereoisomers, and mixtures thereof that can arise from a particular set of substituents, unless otherwise specified.
  • the name or structure also encompasses all enantiomers, diastereomers, and other optical isomers (if there are any) whether in enantiomeric or racemic forms, as well as mixtures of stereoisomers, as would be recognized by a skilled artisan, unless otherwise specified.
  • a general reference to a “Ce alkane,” “hexane” or “hexanes” includes n-hexane, 2-methylpentane, 3 -methylpentane, 2, 2-di methylbutane, and 2,3-dimethylbutane; and a general reference to a “C4 alkyl” or “butyl group” includes an //-butyl group, a .see -butyl group, an zso-butyl group, and a /-butyl group.
  • substituted when used to describe a group, for example, when referring to a substituted analog of a particular group, is intended to describe the compound or group wherein any non-hydrogen moiety formally replaces hydrogen in that group or compound, and is intended to be non-limiting.
  • a compound or group can also be referred to herein as “unsubstituted” or by equivalent terms such as “non-substituted,” which refers to the original group or compound.
  • “Substituted” is intended to be non-limiting and include inorganic substituents or organic substituents as specified and as understood by one of ordinary skill in the art.
  • contact product is used herein to describe compositions and methods wherein the components are contacted together in any order, in any manner, and for any length of time, unless specified otherwise.
  • the components can be contacted by blending or mixing.
  • the contacting of any component can occur in the presence or absence of any other component of the compositions and methods described herein. Combining additional materials or components can be done by any suitable method.
  • the term “contact product” includes mixtures, blends, solutions, slurries, reaction products, and the like, or combinations thereof. Although “contact product” can, and often does, include reaction products, it is not required for the respective components to react with one another.
  • alkyl group is used herein in accordance with the definition specified by IUPAC: a univalent group formed by removing a hydrogen atom from an alkane.
  • the alkyl group may be linear or branched unless otherwise specified.
  • a “cycloalkane” is used herein to refer to a saturated cyclic hydrocarbon, with or without side chains, for example, cyclobutane, cyclopentane, cyclohexane, methyl cyclopentane, and methyl cyclohexane.
  • Other identifiers may be utilized to indicate the presence of particular groups, if any, in the cycloalkane (for example, halogenated cycloalkane indicates the presence of one or more halogen atoms replacing an equivalent number of hydrogen atoms in the cycloalkane).
  • hydrocarbyl group is used herein in accordance with the definition specified by IUPAC: a univalent group formed by removing a hydrogen atom from a hydrocarbon (that is, a group containing only carbon and hydrogen).
  • a hydrocarbyl group includes alkyl groups (linear or branched), cycloalkyl groups, alkenyl groups, aryl groups, and the like.
  • Non-limiting examples of hydrocarbyl groups include methyl, ethyl, butyl, hexyl, phenyl, tolyl, propenyl, and the like.
  • substituent when used herein with regard to the selection of a substituent, the term “independently” indicates that two differently labeled substituents, e.g., R 1 and R 2 , selected from the same pool of substituents may be the same or different.
  • the present disclosure is directed to odorants, odorant compositions, and methods of odorizing materials, such as fluids, which can include a fuel gas.
  • Compounds are provided herein, such as odorants for a fluid.
  • the odorants can be non-toxic (e.g., to humans or mammals) or have a detectable odor below a toxicity level.
  • the compounds can be non-toxic (e.g., to humans or mammals) or have a detectable odor below a toxicity level.
  • the compounds can be environmentally benign by not posing health or toxicity concerns to human or biological species.
  • Combustion products of the compounds also can be environmentally benign.
  • the compounds can be benign to the components of a device system or apparatus, such as a pipeline, combustion system, fuel cell, or any other system, apparatus, or process.
  • the compound includes a terminal alkene.
  • terminal alkene generally refers to organic compounds, including substituted derivatives of organic compounds and/or heteroatom-containing organic compounds, that include a terminal double bond, as depicted in the following moiety:
  • substituted derivatives of organic compounds can include compounds with organic or inorganic substituents.
  • the substituted derivatives of organic compounds include an oxygen substituent.
  • a terminal alkene can include a heteroatom, such as oxygen, nitrogen, etc. When a terminal alkene includes oxygen as a heteroatom, the oxygen can be present as part of an ether moiety.
  • the terminal alkene includes a terminal C3-C20 alkene, a terminal C3-C19 alkene, a terminal C3-C18 alkene, a terminal C3-C17 alkene, a terminal C3-C16 alkene, a terminal C3-C15 alkene, a terminal C3-C14 alkene, a terminal C3-C13 alkene, a terminal C3-C12 alkene, a terminal C3-C11 alkene, a terminal C3-C10 alkene, a terminal C3-C9 alkene, a terminal C3-C alkene, or a terminal C3-C7 alkene.
  • the terminal alkene is hep-l-tene
  • the compound can include a hexene, a heptene, an octene, or a combination thereof.
  • heptene refers to a compound that includes at least one double bond and a linear chain of seven carbon atoms, wherein at least two of the seven carbon atoms are bonded to each other via a double bond, and includes substituted derivatives thereof.
  • octene refers to a compound that includes at least one double bond and a linear chain of eight carbon atoms, wherein at least two of the eight carbon atoms are bonded to each other via a double bond, and includes substituted derivatives thereof.
  • the substituted derivatives of heptene and octene can include, but are not limited to, a C1-C2 substituted heptene or a C1-C2 substituted octene.
  • the substituted derivatives of the heptene and octene can include, but are not limited to, a C1-C2 substituted heptene or a C1-C2 substituted octene.
  • the following table shows a generic schematic of a linear chain of seven carbon atoms, an embodiment of a heptene, and an embodiment of a Ci substituted heptene.
  • a terminal alkene can include one or more double bonds.
  • the compound can be referred to as a “diene.”
  • the diene includes a hexadiene or an octadiene.
  • hexadiene refers to a compound that includes at least two double bonds and a linear chain of six carbon atoms, wherein at least four of the six carbon atoms are bonded to each other via a double bond, and includes substituted derivatives thereof.
  • the hexadiene includes hexa-l,5-diene, where 1,5 refers to the first and second and fifth and sixth carbons, respectively, of the linear chain of six carbon atoms that are bonded to each other via a double bond.
  • the octadiene includes octa-1, 7-diene, where 1,7 refers to the first and second and seventh and eighth carbons, respectively, of the linear chain of eight carbon atoms that are bonded to each other via a double bond.
  • Substituted derivatives of hexadiene or octadiene can include, but are not limited to, a C1-C2 substituted hexadiene or a C1-C2 substituted octadiene.
  • the terminal alkene includes buta-l,3-diene (1,3- butadiene). In some embodiments, the terminal alkene includes hexa-l,5-diene (1,5-hexadiene). In some embodiments, the terminal alkene includes hepta- 1,6-diene (1,6-heptadiene). In some embodiments, the terminal alkene includes octa-1, 7-diene (1,7-octadiene).
  • the heptadiene and/or the octadiene includes a compound of formula (B):
  • the heptadiene and/or the octadiene includes a compound of formula (C):
  • R 1 can be selected from a C3-C12 cycloalkyl, a C3-C10 cycloalkyl, or a C3-C7 cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc.
  • the compound includes a terminal alkyne.
  • terminal alkyne generally refers to organic compounds, including substituted derivatives of organic compounds and/or heteroatom-containing organic compounds, that include a terminal triple bond, as depicted in the following moiety:
  • substituted derivatives of organic compounds can include compounds with organic or inorganic substituents.
  • the substituted derivatives of organic compounds include an oxygen substituent.
  • the terminal alkyne includes a terminal C3-C20 alkyne, a terminal C3-C19 alkyne, a terminal C3-C18 alkyne, a terminal C3-C17 alkyne, a terminal C3-C16 alkyne, a terminal C3-C15 alkyne, a terminal C3-C14 alkyne, a terminal C3-C13 alkyne, a terminal C3-C12 alkyne, a terminal C3-C11 alkyne, a terminal C3-C10 alkyne, a terminal C3-C9 alkyne, a terminal C3-C8 alkyne, or a terminal C3-C7 alkyne.
  • a terminal alkyne can be referred to as a “1 -alkyne”.
  • a “heptyne” can include a 1-heptyne (e.g., hept-l-yne), a 2-heptyne (e.g., hept-2-yne), a 3-heptyne (e.g., hept- 3-yne), or combinations thereof.
  • a terminal alkyne can be a linear terminal alkyne (e.g., but-1- yne), or a branched (e.g., bulky) terminal alkyne, which contains a branched terminal alkyne (e.g., 4-methylpent-l-yne) or a cycloalkane terminal alkyne (e g., cyclopropylacetylene).
  • branched terminal alkyne e.g., 4-methylpent-l-yne
  • a cycloalkane terminal alkyne e.g., cyclopropylacetylene
  • a terminal alkyne can include two or more triple bonds, one or more double bonds, or a combination thereof.
  • the compound can be referred to as an “enyne.”
  • a number of enynes are provided herein, such as but-l-en-3-yne.
  • a double bond of an enyne can be a terminal double bond or a non-terminal double bond.
  • the compound can be referred to as a “diyne.”
  • a diyne can include two terminal triple bonds, or one terminal triple bond and one non-terminal triple bond.
  • a terminal alkyne can include a heteroatom, such as oxygen, nitrogen, etc. When a terminal alkyne includes oxygen as a heteroatom, the oxygen can be present as part of an ether moiety.
  • the odorants include a hexyne, a heptyne, an octyne, or a combination thereof.
  • heptyne refers to a compound that includes at least one triple bond and a linear chain of seven carbon atoms, wherein at least two of the seven carbon atoms are bonded to each other via a triple bond, and includes substituted derivatives thereof.
  • octyne refers to a compound that includes at least one triple bond and a linear chain of eight carbon atoms, wherein at least two of the eight carbon atoms are bonded to each other via a triple bond, and includes substituted derivatives thereof.
  • the substituted derivatives of the heptyne and octyne can include, but are not limited to, a C1-C2 substituted heptyne or a C1-C2 substituted octyne.
  • the following table shows a generic schematic of a linear chain of seven carbon atoms, an embodiment of a heptyne, and an embodiment of a Ci substituted heptyne:
  • the heptyne includes a 2-heptyne, a 3 -heptyne, or a combination thereof.
  • the octyne includes a 3 -octyne, a 4-octyne, or a combination thereof.
  • 3-octyne and “4-octyne”, as used herein, refer to octynes in which (i) the third and fourth carbons, or (ii) the fourth and fifth carbons, respectively, of the linear chain of eight carbon atoms are bonded to each other via a triple bond.
  • the alkyne odorant often can comprise at least 90 mol% of a Ce-Cs alkyne, and more often, at least 95 mol%, at least 97 mol%, at least 98 mol%, or at least 99 mol% of the C&- Cs alkyne.
  • the alkyne odorant can comprise hex-l-yne, hex-2-yne, hept-2-yne, or a combination thereof; alternatively, hex-l-yne; alternatively, hex -2-yne; or alternatively, hept-2- yne.
  • a terminal alkyne includes a compound of formula (I): ⁇ -(CH ⁇ -OC-H; formula (I); wherein n is an integer selected from 0 to 5, or 0 to 4; and wherein R 1 is selected from hydrogen, a Ci-C 6 alkyl, such as methyl, ethyl, propyl, isopropyl, isobutyl, tert-butyl, etc.
  • R 1 can be selected from a C3-C12 cycloalkyl, a C3-C10 cycloalkyl, or a C3-C7 cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc.
  • the terminal alkyne includes a compound of formula (VI): formula (VI); wherein n is an integer selected from 0 to 5, or 0 to 4; and wherein R 3 is hydrogen or a Ci-Ce alkyl, such as methyl, ethyl, propyl, isopropyl, isobutyl, tert-butyl, etc.
  • an alkyne such as an odorant or a terminal alkyne when
  • R 5 or R 6 is hydrogen, includes a compound of formula (VIII):
  • R 5 -C C-R 6 ; formula (VIII); wherein R 5 and R 6 , independently, are hydrogen, a Ci-Ce alkyl, or a Ci-Ce cycloalkyl.
  • the Ci-Ce alkyl can include methyl, ethyl, propyl, isopropyl, isobutyl, tert-butyl, etc.
  • the heptyne and/or the octyne includes a compound of formula (IX):
  • the heptyne and/or the octyne includes a compound of formula (X):
  • the heptyne and/or the octyne includes a compound of formula (XI):
  • the terminal alkene, terminal alkyne, or non-terminal alkyne (such as a compound of formula (VIII) when R or R 6 is hydrogen) includes one or more of the following compounds:
  • odorant compositions include any one or more odorants provided herein and an additive.
  • the additive can be dispersed in the odorant, or vice versa, depending, for example, on whether the additive or the odorant, respectively, is the majority component.
  • the additives for the odorant compositions (and odorized fluid compositions) provided herein can include a stabilizer, an antioxidant, a radical inhibitor, or a combination thereof.
  • the additive is capable of reacting with an odorant poison (such as oxygen (O2), ozone, superoxide anion (Ch’), organic peroxide (ROOR’), organic peroxy radical (ROO»), organic hydroperoxide (ROOH), hydroxyl radical (RO*), inorganic peroxide, hydrogen peroxide, metal oxide, peroxynitrite (ONOO’), nitric oxide (*NO), etc.), thereby avoiding or reducing the likelihood of the (i) formation of one or more undesired products, (ii) polymerization of the odorant, (iii) decomposition of the odorant, or (iv) a combination thereof.
  • an odorant poison such as oxygen (O2), ozone, superoxide anion (Ch’), organic peroxide (ROOR’), organic peroxy radical (
  • the additive such as a radical inhibitor
  • phenolic derivatives exhibit antioxidant properties through two key mechanisms.
  • HAT Hydrogen Atom Transfer
  • phenolic antioxidants can donate a hydrogen atom to free radicals, neutralizing them and preventing oxidative damage of alkynes. This process stabilizes the free radicals by converting them into less reactive species.
  • SET Single Electron Transfer
  • phenolic compounds transfer an electron to free radicals, reducing them and stopping the chain reaction of oxidation. This helps reduce the autocatalytical nature of the alkyne oxidation process.
  • Amine derivatives act as antioxidants primarily by neutralizing free radicals, which are highly reactive molecules that can cause oxidative damage to compounds such as alkynes through three key mechanisms.
  • free radical scavenging amines, particularly aromatic amines, are effective at scavenging free radicals. They donate hydrogen atoms to free radicals, thereby neutralizing them and preventing further oxidative reactions.
  • Some amines can also decompose hydroperoxides, which are intermediates in the oxidation process. This helps to break down potentially harmful compounds before they can cause damage to compounds such as alkynes.
  • Hindered amines such as those derived from 2,2,6,6-tetramethylpiperidine, are particularly effective in protecting materials against UV light degradation.
  • Organic acids such as citric acid, malic acid, and tartaric acid, can act as antioxidants and protect organic compounds from oxidation through two key mechanisms.
  • Organic acids can neutralize free radicals, which are unstable molecules that can cause oxidative damage organic compounds. By donating an electron to these free radicals, organic acids stabilize them and prevent them from causing further damage to compounds such as alkynes.
  • Some organic acids can bind to metal ions impurities like iron and copper, which catalyze oxidative reactions. This reduces the availability of the metal ions to participate in oxidation reactions, thereby protecting other organic compounds such as alkynes.
  • an odorant composition or odorized fluid provided herein can be stored (i) for at least 1 month, 6 months, 12 months, 18 months, 24 months, 30 months, 36 months, 42 months, 48 months, 54 months, or 60 months, (ii) at a temperature of at least -40 °C, at least -30 °C, at least -20 °C, at least -10 °C, at least 0 °C, at least 10 °C, at least 15 °C, at least 20 °C, at least 25 °C, at least 35 °C, at least 45 °C, at least 50 °C, at least 55 °C, at least 60 °C, at least 65 °C, at least 70 °C, at least 75 °C, at least 80 °C, at least 85 °C, or at least 90 °C, or (iii) a combination thereof, and during the storing
  • an odorant composition or odorized fluid provided herein can be stored (i) for at least 1 month, 6 months, 12 months, 18 months, 24 months, 30 months, 36 months, 42 months, 48 months, 54 months, or 60 months, (ii) at a temperature of at least -40 °C, at least -30 °C, at least -20 °C, at least -10 °C, at least 0 °C, at least 10 °C, at least 15 °C, at least 20 °C, at least 25 °C, at least 35 °C, at least 45 °C, at least 50 °C, at least 55 °C, at least 60 °C, at least 65 °C, at least 70 °C, at least 75 °C, at least 80 °C, at least 85 °C, or at least 90 °C, or (iii) a combination thereof, and during the storing of the odorant composition or the odorized fluid less than 10 mol%, less than 5
  • odiferous additives include but are not limited to cyclobutanol, 2,4-dimethylpentan- 3-one, 2-methyl-l -pentanol, 4-methyl-2-pentanol, isopropyl ether, 2,2-dimethylbutanol, isoamyl alcohol (isopentanol), 2-methyl-l -butanol, (S)-(+)-4-methyl-2-pentanol, (2R)-2,3-dimethylbutan- l-ol, (2R)-2-methylpentan-l-ol, 2,3-dimethylbutan-l-ol, 3-methylhexan-2-ol, 2,3-dimethyl-2- pentanol, 3-methylpentan-2-ol, 2-methylpentan-3-ol, 3 -methyl-(R)-3 -hexanol, 3 -pentanol, 2- methylpentan-2-ol, 2,3-dimethyl
  • An odiferous additive can contribute to the alarming scent of an odorized fluid.
  • a concentration of odorant that is used in an odorized fluid or an odorant composition can be reduced without undesirably impacting the detectability of the odorized fluid.
  • the additive generally can be any compound that is capable of acting as a stabilizer, an antioxidant, and/or a radical inhibitor, especially for an odorant that includes an alkynyl moiety.
  • stabilizer, antioxidant, and/or radical inhibitor refers to a compound or material that prevents or delays the chemical degradation of a fluid and/or an odorant compound, such as an alkyne.
  • the additive can be present in the composition in any suitable amount.
  • the additive stabilizer, antioxidant, and/or radical inhibitor
  • the additive is present in the composition at a concentration of about 10 ppmw (ppm by weight) to about 10 wt%, about 10 ppmw to about 8 wt%, about 10 ppmw to about 6 wt%, about 10 ppmw to about 4 wt%, about 10 ppmw to about 2 wt%, about 10 ppmw to about 1 wt%, about 10 ppmw to about 5,000 ppmw, about 50 ppmw to about 10 wt%, about 50 ppmw to about 8 wt%, about 50 ppmw to about 6 wt%, about 50 ppmw to about 4 wt%, about 50 ppmw (ppm by weight) to about 10 wt%, about 10 ppmw to about 8 wt%, about 10 ppmw to about 6 wt%, about 10 pp
  • the additive is present in the composition at a concentration of about 10 ppmw (ppm by weight) to about 1,000 ppmw, about 10 ppmw to about 900 ppmw, about 10 ppmw to 750 ppmw, about 10 ppmw to about 500 ppmw, about 50 ppmw to about 1,000 ppmw, about 50 ppmw to 750 ppmw, about 50 ppmw to about 500 ppmw, about 200 ppmw to about 1,000 ppmw, about 200 ppmw to about 900 ppmw, about 200 ppmw to 750 ppmw, or about 200 ppmw to about 500 ppmw, based on the weight of the odorant in the composition.
  • stabilizers, antioxidants, and radical inhibitors include phenolic derivatives including but not limited to, 2-methylphenol (o-cresol), 3 -methylphenol (m-cresol), 4-methylphenol (p-cresol), 2-ethylphenol, 3 -ethylphenol, 4-ethylphenol, 2-propylphenol, 3- propylphenol, 4-propylphenol, 2-butylphenol, 3 -butylphenol, 4-butylphenol, 2-methoxyphenol (guaiacol), 3-methoxyphenol, 4-methoxyphenol or 4-hydroxy anisole or hydroquinone monomethyl ether (also known as MeHQ), 2-ethoxyphenol, 3-ethoxyphenol, 4-ethoxyphenol, 2- methoxy-3 -methylphenol, 4-methoxy-3 -methylphenol, 2-methoxy-4-methylphenol (creosol), 3- methoxy -4-methylphenol, 2-methoxy-5-methylphenol (isocreosol), 3-methoxy-5-methylphenol, 2,6-di-ter
  • caffeic acid caffeic acid, chlorogenic acid, ferulic acid, p-coumaric acid, etc.
  • flavonoids or a derivative thereof (taxifolin, luteolin, apigenin, tangeritin, quercetin, kaempferol, myricetin, fisetin, galangin, isorhamnetin, pachypodol, rhamnazin, pyranoflavonols, furanoflavonols, hesperetin, naringenin, eriodictyol, homoeriodictyol, cyanidin, delphinidin, malvidin, pelargonidin, peonidin, petunidin, catechin, gallocatechin, catechin 3-gallate, gallocatechin 3-gallate, epicatechins, epigallocatechin, epicatechin 3-gallate, epigallocatechin 3-gallate, etc), glutathione, melatonin and uric acid.
  • the additive has a boiling point that is about 300 °C or less, about 270 °C or less, about 250 °C or less, about 220 °C or less, about 190 °C or less, about 160 °C or less, about 130 °C or less, about 120 °C or less, about 110 °C or less, or about 100 °C or less.
  • the additive has a freezing point that is about 100 °C or less, about 50 °C or less, about 0 °C or less, about -80 °C or less, about -70 °C or less, about -60 °C or less, about -50 °C or less, about -40 °C or less, about -30 °C or less, about -20 °C or less, or about -10 °C or less.
  • the additive can be a non-toxic compound.
  • the additive also can be environmentally benign.
  • the additive has an acute oral toxicity of at least 100 mg/kg, at least 200 mg/kg, at least 300 mg/kg, at least 500 mg/kg, at least 1,000 mg/kg, at least 2,000 mg/kg, at least 3,000 mg/kg, at least 4,000 mg/kg, or at least 5,000 mg/kg.
  • the additive can have any volatility.
  • the additive can be relatively volatile.
  • the additive has a vapor pressure (at 20 °C) of at least 0.001 kPa, at least 0.01 kPa, at least 0.1 kPa, or at least 1 kPa.
  • the additive can be a compound that includes an aldehyde moiety, such as a compound selected from ethanal, propanal, 1 -butanal, isobutanal (2-methylpropanal), pentanal (valeraldehyde), isopentanal (isovaleraldehyde or 3 -methylbutanal), 2-methylbutanal, pivaldehyde (2,2-dimethylpropanal), hexanal, 4-methylpentanal, 3-methylpentanal, 2- methylpentanal, 3, 3 -dimethylbutanal, 1 -octanal, furfural, glyoxal, or a combination thereof.
  • an aldehyde moiety such as a compound selected from ethanal, propanal, 1 -butanal, isobutanal (2-methylpropanal), pentanal (valeraldehyde), isopentanal (isovaleraldehyde or 3 -methylbut
  • the additive is a C3-C10 alkyl aldehyde, a C3-C6 alkyl aldehyde, or a derivative thereof, such as a derivative comprising an alkenyl moiety, an alkynyl moiety, or a combination thereof, wherein the alkyl aldehyde is a cyclic or non-cyclic aldehyde.
  • the additive can be a compound that includes a ketone moiety (for example, one ketone moiety, two ketone moieties, three ketone moieties, etc.).
  • the additive can include a compound selected from acetone, butanone, 2-pentanone, 3-pentanone, 3-methyl-2- butanone, 2-hexanone, 3 -hexanone, 3-methyl-2-pentanone, 2-methyl-3 -pentanone, 4- methylpentanone, 3,3-dimethyl-2-butanone, 2,3-butadione, 2,3 -pentadione, 2,4-pentadione, 3- methyl-penta-2, 4-dione, cyclobutanone, cyclopentanone, cyclohexanone, methyl isobutyl ketone, or a combination thereof.
  • the compound is a C3-C10 alkyl ketone, a C3- C10 alkyl diketone, a C4-C8 alkyl ketone, a C4-C8 alkyl diketone, a C3-C6 alkyl ketone, a C3-C6 alkyl diketone, or a derivative thereof, such as a derivative comprising an alkenyl moiety, an alkynyl moiety, or a combination thereof, wherein the alkyl ketone is a cyclic alkyl ketone or a non-cyclic alkyl ketone.
  • the additive can be a compound that includes an alcohol moiety (e.g., one alcohol moiety, two alcohol moieties, etc.).
  • the additive can include a compound selected from methanol, ethanol, propanol, isopropanol, butanol, 2-butanol, tert-butanol, 3-methyl-2- butanol, 2-pentanol, 3-pentanol, 2-methyl-3 -pentanol, butane-2,3-diol, 1-octanol, 2,3 -pentadiol, 2,4-pentadiol, benzyl alcohol, or a combination thereof.
  • the additive includes a C1-C10 alkyl alcohol, a C1-C10 alkyl di-alcohol, a C2-C10 alkyl alcohol, a C2-C10 alkyl di-alcohol, a Ci-Ce alkyl alcohol, a Ci-Ce alkyl di-alcohol, or a derivative thereof, such as a derivative comprising an alkenyl moiety, an alkynyl moiety, or a combination thereof.
  • the additive can be a compound that includes an ester moiety.
  • the additive can include methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, isobutyl acetate, tert-butyl acetate, methyl propionate, ethyl propionate, propyl propionate, isopropyl propionate, methyl sorbate, ethyl sorbate, propyl sorbate, isopropyl sorbate, ethyl 2- butynoate, or a combination thereof.
  • the compound is a C2 to C10 alkyl ester, a C2-C6 alkyl ester, or a derivative thereof, such as a derivative comprising an alkenyl moiety, an alkynyl moiety, or a combination thereof.
  • the additive can be a compound that includes an ether moiety.
  • the additive can include dimethyl ether, diethyl ether, methyl ethyl ether, dipropyl ether, methyl propyl ether, ether propyl ether, diisopropyl ether, methyl isopropyl ether, ethyl isopropyl ether, propyl isopropyl ether, methyl butyl ether, ethyl butyl ether, methyl isobutyl ether, ethyl isobutyl ether, or a combination thereof.
  • the additive includes a C1-C10 dialkyl ether, a Ci-Ce dialkyl ether, a C1-C2 dialkyl ether, or a derivative thereof, such as a derivative comprising an alkenyl moiety, an alkynyl moiety, or a combination thereof.
  • the additive can be an unsubstituted or substituted diphenyl ether, or an unsubstituted or substituted C1-C10 alkylphenyl ether (which can have the following structure: C1-C10 alkyl-O-Ph, wherein, optionally, the phenyl moiety is substituted).
  • the additive is a compound that includes a cycloalkanol moiety, such as a compound selected from cyclopropanol, cyclobutanol, cyclopentanol, or a combination thereof.
  • the additive is a Cs-Cs cycloalkanol, or a C3-C4 cycloalkanol.
  • the additive is an unsubstituted or substituted phenol, such as 2-methylphenol (o-cresol), 3 -methylphenol (m-cresol), 4-methylphenol (p-cresol), 2- ethylphenol, 3 -ethylphenol, 4-ethylphenol, 2-propylphenol, 3 -propylphenol, 4-propylphenol, 2- butylphenol, 3 -butylphenol, 4-butylphenol, 2-methoxyphenol (guaiacol), 3-methoxyphenol, 4- methoxyphenol or 4-Hydroxyanisole or hydroquinone monomethyl ether (also known as MeHQ), 2-ethoxyphenol, 3-ethoxyphenol, 4-ethoxyphenol, 2-methoxy-3 -methylphenol, 4- methoxy-3 -methylphenol, 2-methoxy-4-methylphenol (creosol), 3-methoxy-4-methylphenol, 2- methoxy-5-methylphenol (isocreosol), 3-methoxy-5-methylphenol, 2,6-
  • 2-methylphenol o-
  • the additive is a compound that includes a carboxylic acid moiety, such as a compound selected from formic acid, acetic acid, benzoic acid, sorbic acid, citric acid, malic acid, tartaric acid, succinic acid, lactic acid, oxalic acid, or a combination thereof.
  • the additive is a C2-C10 alkyl carboxylic acid, or a derivative thereof, such as a derivative comprising an alkenyl moiety, an alkynyl moiety, or a combination thereof.
  • the additive is an unsubstituted or substituted quinoline.
  • the odorized fluid composition containing the additive can be prepared in any suitable manner, but generally, involved a process that comprises contacting the fluid, the additive, and the odorant in any order or sequence. It is important that odor leaks or odor releases be avoided in the preparation of the odorized fluid composition.
  • the odorized fluid composition is prepared by a process that comprises introducing the additive in solid form or liquid form through a first leak- tight inlet port into an odorant vessel; introducing the odorant through the first leak-tight inlet port or a second leak-tight inlet port into the odorant vessel and mixing with the additive to form an odorant composition; and discharging at least a portion of the odorant composition from the odorant vessel through a leak-tight outlet port and contacting with the fluid to form the odorized fluid composition.
  • Mixing can be simply allowing sufficient time for the materials to combine and form a uniform composition, or a suitable agitation technique can be used.
  • the odorant vessel can be any suitable storage tank, isotainer, drum, for example leak-free stainless stain drums commercialized by Wilhelm Schmidt GmbH, and the like.
  • the odorized fluid composition can be prepared by a process that comprises introducing the additive in liquid form into a multiport vessel; connecting the multiport vessel to an odorant vessel containing the odorant and transferring the additive to the odorant vessel through a leak-tight inlet port and mixing the additive with the odorant to form an odorant composition; disconnecting the multiport vessel from the odorant vessel; and discharging at least a portion of the odorant composition from the odorant vessel through a leak- tight outlet port and contacting with the fluid to form the odorized fluid composition.
  • the transfer of the additive from the multiport vessel to the odorant vessel can be accomplished by any suitable means, such as pumping, gravity driven flow, pressure driven flow, and the like.
  • a concentrated solution can be prepared by combining the additive in solid form with a small amount of the odorant and introducing the concentrated solution (in liquid form) into the multiport vessel.
  • the additive can comprise a diluent, such as a diluent for an odorant compound such as an alkyne.
  • the additive can include a Cs-Cs saturated hydrocarbon (e.g., a pentane, a cyclopentane, a hexane, a cyclohexane, a heptane, a cycloheptane, an octane, and/or a fluorinated hydrocarbon, such as, for example, PFC-116, PFC-c216, PFC-218, or PFC- 318).
  • a Cs-Cs saturated hydrocarbon e.g., a pentane, a cyclopentane, a hexane, a cyclohexane, a heptane, a cycloheptane, an octane
  • a fluorinated hydrocarbon such as, for example, PFC-116
  • An odorant generally can be present in an odorant composition at any desirable amount.
  • the odorant is present in an odorant composition at a total amount of at least 1 wt%, at least 5 wt%, at least 10 wt%, at least 20 wt%, at least 30 wt%, at least 40 wt%, at least 50 wt%, at least 60 wt%, at least 70 wt%, at least 80 wt%, or at least 90 wt%, based on the total weight of the odorant composition.
  • an odorant includes two or more compounds, such as a heptyne and an octyne
  • the heptyne and the octyne can be present in the odorant composition at a total amount of at least 1 wt%, at least 5 wt%, at least 10 wt%, at least 20 wt%, at least 30 wt%, at least 40 wt%, at least 50 wt%, at least 60 wt%, at least 70 wt%, at least 80 wt%, or at least 90 wt%, based on the total weight of the odorant composition.
  • heptyne and octyne are present in an odorant composition having a total weight of 100 g, then the heptyne and octyne are present in the odorant composition at a total amount of 50 wt%.
  • An odorant composition generally can be in any phase, e.g., a liquid or gas.
  • An odorant composition can be stored and/or used in any desirable phase.
  • odorized fluids also provided herein are odorized fluids (alternatively referred to as odorized fluid compositions).
  • the odorized fluids generally include (i) a fluid, such as a gas, and (ii) any of the odorants or the odorant compositions disclosed herein.
  • An odorant or an odorant composition can be dispersed, evenly or unevenly, in the fluid.
  • An odorant can be present in an odorized fluid at any desired amount.
  • the odorant composition can be present at an amount that is effective to achieve in the odorized fluid a desirable concentration of the odorant.
  • an odorant is present in an odorized fluid at a concentration of 1,000 mg/m 3 n or less, 900 mg/m 3 n or less, 800 mg/m 3 n or less, 700 mg/m 3 n or less, 600 mg/m 3 n or less, 500 mg/m 3 n or less, 400 mg/m 3 n or less, 300 mg/m 3 n or less, 200 mg/m 3 n or less, 100 mg/m 3 n or less, 90 mg/m 3 n or less, 80 mg/m 3 n or less, 70 mg/m 3 n or less, 60 mg/m 3 n or less, 50 mg/m 3 n or less, 40 mg/m 3 n or less, 30 mg/m 3 n or less, 20 mg/m 3 n or less, or 10 mg/m 3 n or less.
  • an odorant is present in an odorized fluid at a concentration of at least 0.5 mg/m 3 n, at least 1 mg/m 3 n, at least 2 mg/m 3 n, at least 3 mg/m 3 n, at least 4 mg/m 3 n, at least 5 mg/m 3 n, at least 6 mg/m 3 n, at least 7 mg/m 3 n, at least 8 mg/m 3 n, at least 9 mg/m 3 n, or at least 10 mg/m 3 n.
  • an odorant is present in an odorized fluid at a concentration of about 1 mg/m 3 n to about 1,000 mg/m 3 n, about 1 mg/m 3 n to about 900 mg/m 3 n, about 1 mg/m 3 n to about 800 mg/m 3 n, about 1 mg/m 3 n to about 700 mg/m 3 n, about 1 mg/m 3 n to about 600 mg/m 3 n, about 1 mg/m 3 n to about 500 mg/m 3 n, about 1 mg/m 3 n to about 400 mg/m 3 n, about 1 mg/m 3 n to about 300 mg/m 3 n, about 1 mg/m 3 n to about 200 mg/m 3 n, about 1 mg/m 3 n to about 100 mg/m 3 n, about 1 mg/m 3 n to about 90 mg/m 3 n, about 1 mg/m 3 n to about 80 mg/m 3 n, about 1 mg/m 3 n to about 70 mg
  • an odorant is present in an odorized fluid at a concentration of about 5 mg/m 3 n to about 5,000 mg/m 3 n, about 5 mg/m 3 n to about 2,500 mg/m 3 n, about 5 mg/m 3 n to about 1,000 mg/m 3 n, about 5 mg/m 3 n to about 900 mg/m 3 n, about 5 mg/m 3 n to about 800 mg/m 3 n, about 5 mg/m 3 n to about 700 mg/m 3 n, about 5 mg/m 3 n to about 600 mg/m 3 n, about 5 mg/m 3 n to about 500 mg/m 3 n, about 5 mg/m 3 n to about 400 mg/m 3 n, about 5 mg/m 3 n to about 300 mg/m 3 n, about 5 mg/m 3 n to about 200 mg/m 3 n, about 5 mg/m 3 n to about 100 mg/m 3 n, about 5 mg/m 3 n to about 90 mg/m
  • the odorant is present in the odorized fluid at a concentration of about 1 mg/m 3 n to about 50 mg/m 3 n, about 1 mg/m 3 n to about 40 mg/m 3 n, about 1 mg/m 3 n to about 30 mg/m 3 n, about 1 mg/m 3 n to about 20 mg/m 3 n, about 1 mg/m 3 n to about 10 mg/m 3 n, about 2 mg/m 3 n to about 50 mg/m 3 n, about 2 mg/m 3 n to about 40 mg/m 3 n, about 2 mg/m 3 n to about 30 mg/m 3 n, about 2 mg/m 3 n to about 20 mg/m 3 n, about 2 mg/m 3 n to about 15 mg/m 3 n, about 5 mg/m 3 n to about 50 mg/m 3 n, about 5 mg/m 3 n to about 40 mg/m 3 n, about 5 mg/m 3 n to about 30 mg/m 3 n, about 1 mg
  • the odorant is present in the odorized fluid at a concentration of about 2 mg/m 3 n to about 20 mg/m 3 n, about 2 mg/m 3 n to about 15 mg/m 3 n, about 5 mg/m 3 n to about 20 mg/m 3 n, about 5 mg/m 3 n to about 15 mg/m 3 n, or about 5 mg/m 3 n to about 10 mg/m 3 n.
  • the units “mg/m 3 n” indicate a concentration (“mg/m 3 ”) at normal (“n”) atmospheric pressure at a location, which, at sea level, is typically 1 bar or 14.7 psi.
  • An odorized fluid can be an odorized fluid that is suitable for a particular use, depending on the character of a fluid that is present in an odorized fluid.
  • an odorized fluid can be a fuel for a fuel cell, as described herein.
  • the methods include providing a fluid and contacting the fluid and an odorant or an odorant composition as provided herein to form an odorized fluid.
  • the fluid and/or the odorized fluid can be present in a fuel distribution system.
  • the fuel distribution system can include any fuel supply infrastructure (fuel storage, fuel distribution, fuel delivery, etc.).
  • the methods of odorizing a fluid also include disposing the fluid and/or the odorized fluid in a fuel distribution system, such as any fuel supply infrastructure (fuel storage, fuel distribution, fuel delivery, etc.).
  • the providing of a fluid can include capturing the fluid.
  • the fluid can be captured using any technique known in the art.
  • the methods also include pressurizing the odorized fluid, storing the odorized fluid, or a combination thereof.
  • the odorant or the odorant composition can be in any phase, such as a liquid phase, a gaseous phase, or a combination thereof before, during, and/or after the contacting of the fluid and the odorant.
  • the providing of the fluid can include providing a container in which the fluid is disposed, and the contacting of the fluid and the odorant or the odorant composition can include disposing the odorant or the odorant composition in the container.
  • the providing of the fluid can include providing a first stream that includes the fluid. When a first stream that includes the fluid is provided, the contacting of the fluid and the odorant or the odorant composition can include contacting the first stream and a second stream that includes the odorant or the odorant composition.
  • the contacting of the fluid and the odorant or the odorant composition can be achieved using any known technique.
  • the contacting of the fluid and the odorant or odorant composition can include dispensing the odorant or the odorant composition with a liquid meter.
  • the contacting of the fluid and the odorant or the odorant composition can include nebulizing the odorant or the odorant composition.
  • the odorants or odorant compositions provided herein can be used to odorize any fluid, and the odorized fluids can include any fluid.
  • the fluids generally can be in any phase, e.g., liquid or gas.
  • the fluid includes a fuel gas.
  • the fluid can include hydrogen gas (H2) or a hydrogen gas blend.
  • the fluid can include a natural or synthetic combustion gas.
  • the fluid can include natural gas, LNG (liquid natural gas), liquefied petroleum gas (LPG), municipal gas, heating gas, or a combination thereof.
  • the fluid can include methane, ethane, ethene, acetylene, propane, propene, butane, isobutane, butene, pentane, or a combination thereof.
  • the fluid can include water gas, synthesis gas, reform gas, generator gas, coke gas, or a combination thereof.
  • the fluid can include a non-combustible gas.
  • the fluid can include carbon monoxide, carbon dioxide, industrial gases (e.g., nitrogen (N2), oxygen (O2), argon, helium, etc.), or a combination thereof.
  • the fluid comprises hydrogen gas (H2) and at least 10 mol%, and more often, at least 20 mol%, at least 30 mol%, at least 50 mol%, at least 75 mol%, at least 85 mol%, at least 90 mol%, at least 95 mol%, at least 97 mol%, at least 98 mol%, or at least 99 mol% of the fluid is the hydrogen gas.
  • the fluid comprises hydrogen gas (H2) and from 10 mol% to 40 mol%, from 10 mol% to 30 mol%, from 10 mol% to 25 mol%, from 15 mol% to 30 mol%, or from 15 mol% to 25 mol% of the fluid is the hydrogen gas.
  • the compounds, such as terminal alkynes or terminal alkenes, or compositions provided herein can be used in combination with a sensor, such as a sensor designed to indicate the presence of a compound that is an odorant. Therefore, systems are provided herein that include a sensor and a compound, such as a terminal alkyne or terminal alkene, that is an odorant, or a sensor and a composition that includes a compound, such as a terminal alkyne or terminal alkene, that is an odorant.
  • a sensor can be coupled to any device or apparatus, such as a pipeline, a fuel supply, a fuel cell, or some other component of the fuel cell system, or any appliance using hydrogen as fuel, or any component of an appliance using hydrogen as fuel.
  • the sensor can be located in proximity to a self-contained fuel supply, a fuel consumption unit, or both, which can permit the sensor to detect any leaks quickly and/or effectively.
  • a sensor also can include circuitry programmed to shut down a fuel cell, other appliance or system, or any other components in the event of a detected leak.
  • the addition of the sensor can facilitate use of organic odorants at very low concentrations that are not detectable by humans for special applications or circumstances.
  • the odorant can be selected so that extremely high sensitivity and selectivity of the sensor can be realized to avoid false alarms.
  • the methods generally can include using any of the odorized fluids provided herein as a source of energy.
  • the odorized fluids can be a fuel for an appliance or device, such as a fuel cell.
  • the methods include providing a fuel cell having an anode and contacting the anode and any of the odorized fluids provided herein, such as odorized hydrogen gas. The contacting of an anode and an odorized fluid can produce an oxidized odorized fluid.
  • the methods include removing (e.g., scrubbing, adsorbing, absorbing, or decomposing) an odorant from the odorized fluid or the oxidized odorized fluid.
  • the removal of the odorant can occur at any one or more points of the methods provided herein.
  • the methods can include removing an odorant from an oxidized odorized fluid or removing an odorant from an odorized fluid prior to contacting an anode and the odorized fluid.
  • Removal of an odorant from a fuel gas can be necessary or desirable, in some instances, such as (i) when an odorant is detrimental for the end-use of a fuel gas or fuel gas consuming appliance and/or device, and/or (ii) when an odorant is not eliminated during the consumption of the fuel gas, which can result in an environmental release of the odorant, thereby possibly negating the ability of the odorant to indicate leaks.
  • the methods include removing (e.g., scrubbing, adsorbing, absorbing, or decomposing) an odorant from an exit, off-gas, or flue gas from a fuel cell or any appliance using hydrogen.
  • the odorants provided herein can be removed by any known technique, such as (i) specially designed or commercially available adsorption and/or absorption processes, (ii) a water trap, and/or (iii) a humidifier system based on an odorant’s solubility in water.
  • the removal e.g., scrubbing, adsorbing, absorbing or decomposing
  • a compound such as a terminal alkyne, terminal alkene, additive, etc.
  • These techniques can include, but are not limited to, catalytic decomposition on metal, metal oxide, zeolite, or other substrates (see US7780933B2, US8658321B2, JP2018153634A, JP06317909B2, JP05766744B2, JP6306377A, JP04745557B2, US8444945B2, JP04822692B2, US7837964B2, US20080090115A1, US10889597 B2); absorption or adsorption on activated carbon, zeolites, silica, or other substrates (see JP07271867B2, JP05949333B2, JP2012143747A, JP2011201975A, JP05295689B2, JP2001019984A, JP2001157709A, US6875410B2, JP05051864B2, US805777B2, EP2337621B1); condensation; concentration; evaporation; filtration; membrane separation; or a combination thereof.
  • a compound can be removed from a fluid, such as a treated fluid or an oxidized treated fluid, by an adsorption or absorption media using one or more materials, such as a porous carrier.
  • materials include silica- alumina; silica; alumina; zeolite, preferably a zeolite containing Ag, Cu, Zn, Ni, Fe, Ce, La, Zr, and Ti metallic element(s), titania, zirconia, magnesia, silica-magnesia, or zinc oxide; a porous inorganic oxide, such as one selected from the group consisting of Ag, Cu, Ni, Zn, Mn, Fe, Co, Al, Si, Ce, an alkali metal, an alkaline earth metal, or a rare earth metal; terra alba; clay; diatomaceous earth; activated carbon; activated carbon oxide; activated carbon formed by activated carbon processing with nitric acid; an organometallic framework compound (MO)
  • a compound can be removed from a treated fluid by catalytic conversion to one or more compounds having a lower odor detection threshold using one or more materials, such as porous inorganic oxide selected from the group consisting of Ag, Cu, Ni, Zn, Mn, Fe, Co, Al, Si, B, P; an alkali metal; an alkaline earth metal (for example, oxides of magnesium, calcium, strontium and barium); a rare earth metal (for example, oxides of scandium, yttrium, cerium, ytterbium and lanthanum); and a transition metal (for example, oxides of nickel, cobalt, vanadium, chromium, manganese, molybdenum, tungsten, copper, silver, zinc, iron, titanium, and zirconium).
  • porous inorganic oxide selected from the group consisting of Ag, Cu, Ni, Zn, Mn, Fe, Co, Al, Si, B, P
  • an alkali metal for example, oxides of magnesium, calcium, strontium
  • the porous inorganic oxide can be selected from the group consisting of alumina, silica, silica-alumina, and cerium oxide; a transition metal oxide; a transition metal compound; an alkaline earth metal oxide; and a rare earth metal oxide.
  • the transition metal is nickel, cobalt, vanadium, chromium, manganese, molybdenum, tungsten, copper, silver, zinc, iron, titanium, and zirconium.
  • the alkaline earth metal is magnesium, calcium, barium, or strontium.
  • the rare earth metal of the rare earth oxide is selected from scandium, yttrium, cerium, ytterbium, and lanthanum.
  • a porous inorganic oxide can be selected from a group 13-14 oxide where the group 13-14 element is selected from boron, aluminum, gallium, silicon, germanium, and tin.
  • a compound can be removed from a treated fluid using a precious metal catalyst such as Pt/Pd/Rh catalyst, Pt/Pd catalyst, Pt/Rh catalyst, Pd/Rh catalyst, Pt catalyst, Pd catalyst, Au catalyst, and Pt/AhCh catalyst; an oxide catalyst such a zeolite, silica-alumina, silica, alumina, zeolite, titania, zirconia, magnesia, silica-magnesia, and zinc oxide; a Cu-ZSM-5 catalyst; an organometallic framework compound (MOF) catalyst; and a perovskite type-catalyst in a granular form, a powder form, or fibrous form.
  • a precious metal catalyst such as Pt/Pd/Rh catalyst, Pt/Pd catalyst, Pt/Rh catalyst, Pd/Rh catalyst, Pt catalyst, Pd catalyst, Au catalyst, and Pt/AhCh catalyst
  • an oxide catalyst such a zeolite
  • a compound can be removed from a treated fluid by scrubbing in a water trap or solvent trap containing alkali metal hydroxides, alkali metal Ci to C4 alkyl acid, inorganic peroxide, organic peroxide, perchlorate, ionic or nonionic emulsifier, or a combination thereof.
  • the removal of at least a portion of the odorant from the odorized fluid or the exhaust gas can include subjecting the odorized fluid or the exhaust gas to condensation.
  • the condensation can include cooling, pressurizing, or a combination thereof the odorized fluid or the exhaust gas to recover the at least a portion of the odorant as a liquid.
  • the removal of at least a portion of the odorant from an odorized fluid or an exhaust gas can include contacting the odorized fluid or the exhaust gas and a membrane or fdter, wherein the membrane or the filter is configured to retain the odorant or the non-odorant components of the odorized fluid or the exhaust gas.
  • the membrane can include a polymer such as polyethylene, polypropylene, a polyamide, a polyimide, a cellulose acetate, a polysulphone, a polydimethylsiloxane, a fluoropolymer (such as polytetrafluoroethylene (PTFE)), polyvinylidene fluoride (PVDF), ethylene and chlorotrifluoroethylene copolymer (ECTFE), perfluoro sulfonic acid polymer, (such as Nafion and Aquivion), a nanoporous material, a silica mesoporous material, a zeolite, a metal-organic framework (MOF), a perovskite, a metal, or a combination thereof.
  • a polymer such as polyethylene, polypropylene, a polyamide, a polyimide, a cellulose acetate, a polysulphone, a polydimethylsiloxane
  • An odorant removal unit can be inserted prior to the storage unit or fuel delivery system to an appliance, such as a fuel cell, to consume the fuel gas.
  • an odorant removal unit can be inserted after the storage unit or the appliance that consumes the fuel gas.
  • the odorant should be below the critical concentration that negatively impacts the performance of the fuel cell (e.g., below the concentration that reduces efficiency).
  • Other processes in which a treated fluid can require removal of an odorant include chemical processes (e.g., hydrogenation and reduction reactions, metal hydride synthesis); petrochemical processes (e.g.
  • An odorant or odorant composition can be at least partially consumable by the fuel cell, thereby improving the performance of the fuel cell, increasing the energy produced by the fuel cell, or a combination thereof relative to a fuel cell operated with the fluid of the odorized fluid in the absence of the odorant or the odorant composition.
  • Dilutions of various odorants were prepared by mixing an organic compound in water to prepare a concentrated solution based on the water solubility of the organic compound. The concentrated solution was then dissolved in water to reach a desired concentration. The actual concentration in the vial headspace and concentration exposure to the panelist varied based on the vapor pressure of the compounds tested and the diffusion of the compounds in air. [0139] The odorant solutions at various concentrations were evaluated by olfactory testing using a method similar those disclosed in literature (see Journal of Applied Toxicology, 3, 272-289, 1983; Perception & Psychophysics, 39, 281-286, 1986) and an olfactory panel of at least 8 panel members.
  • the odor characteristic of each odorant was ranked from 1 (extremely unpleasant) to 10 (extremely pleasant). Each participant also gave a description of the odorant. Participants were exposed to 10-fold changes in concentration to determine the odor detection threshold from 0.001 mg/L to 10 mg/L. The odor detection threshold represented the lowest concentration at which the panelists could detect the odorant.
  • the odor characteristic score for each compound was calculated by averaging the score (1-10) reported by each of the panel members for each dilution, and the lowest of these scores for each compound (independent of dilution) is reported in the following table.
  • Example 1.1 (hept-2-yne), Example 1.3 (oct-3-yne), Example 1.5 (hex- l-en-5-yne), Example 1.6 (hept-l-en-6-yne), Example 1.7 (hex-l-yne), Comparative Example 1.15 (hepta- 1,6-diyne), Comparative Example 1.16 (octa-1, 7-diyne), Comparative Example 1.19 (3-(propan-2-yloxy)-prop-l -yne) and Example 1.28 (hex-2-yne), the compounds provide a comparable or stronger odor than THT at a similar concentration.
  • Dilutions of various odorants were prepared by mixing 50-100 mg/m 3 n of each compound in pure hydrogen gas (class 5.0) in a gas cylinder at 100 bar.
  • the hydrogen cylinders were prepared by a gravimetric method, as defined in ISO 6142.
  • Odorized hydrogen samples were blended with air at ratios from about 50: 1 to 2000: 1. Olfactory panel members were asked to give their impression of the smell character and indicate whether they found the odorant to be unpleasant (e.g., would the odor cause serious concerns if smelled in a real-world application).
  • the odor threshold was determined by stepwise increases of the concentration. The concentration was doubled every step, starting from a dilution rate of 1:2000. In some cases, even at the highest dilution (lowest concentration tested), the odorant could still be detected. In other cases, even at the highest concentration tested, the odorant could not be detected. For odorants in which this occurred, the odor detection threshold and nominal odor concentration are reported as less than ( ⁇ ) or greater than (>) the known concentration.
  • the nominal concentration of the odor strength was established by comparing the odor strength of each compound to a set concentration of the odorant tetrahydrothiophene (THT). This permitted quantification of the concentration of the test compound that matched the odor strength of THT.
  • a lower concentration of odorant it is preferred to use a lower concentration of odorant to achieve the same odor strength as THT, indicating that the odor intensity curve as defined in ISO/DTS 18222 has a steeper slope, and that a compound has a lower odor detection threshold compared to THT.
  • a lower concentration will achieve an alarming level of odor, but the concentration of the odorant should be sufficient to result in an odor similar to that of THT.
  • Results of Example 2 are provided in the following table. The data show that some compounds performed similarly to THT when used as odorants.
  • Example 2.1 hept-2-yne
  • Example 2.2 hept-3-yne
  • Comparative Example 2.6 pent- 1 -yne
  • Example 2.5 hex- 1 -yne
  • Example 2.9 hex-l-en-5-yne
  • Comparative Example 2.11 hepta- 1,6-diyne
  • Example 2.19 hex-2-yne
  • Example 2.1 hept-2-yne
  • Example 2.5 hex-1 -yne
  • 1 -/2-hexynes, 2- /3 -heptynes, and 3-/4-octynes have odor detection thresholds comparable to or lower than previously considered alkynes (e.g.,1 -pentyne) and can serve as a fluid (gas) odorant in hydrogen gas and other fluids despite having a higher number of total aliphatic carbons (which corresponds to a higher boiling point and lower vapor pressure).
  • 1 -/2-hexynes, 2-/3 -heptynes, and 3- /4-octynes have an odor strength equal to or better than other alkynes (e.g., pent-l-yne) and THT.
  • 2-/3-heptynes and 3-/4-octynes demonstrate a distinct and unique odor compared to equivalent terminal alkynes (namely, hept-l-yne and oct-l-yne). These odor characteristics impart an alarming and unique smell similar to typical commercial natural gas odorants.
  • enyne compounds are suitable odorants for fluids, particularly gases.
  • the odor properties and alarming odor character of enyne compounds are comparable to a typical commercial natural gas odorant (THT) and other alkynes considered to be gas odorants such as pent-l-yne.
  • THT commercial natural gas odorant
  • the enyne compounds do not behave like an alkyne or an alkene but instead have their own unique set of odor properties.
  • Embodiments of the enyne compounds have odor detection levels equal to or lower than previously considered alkynes (pent-l-yne); odor strengths equal to or better than previously considered alkynes (pent-l-yne) and a typical commercial natural gas odorant (THT); significantly lower odor detection thresholds compared to similar length dienes and alkynes (for example, 1-heptyne, 1-octyne and 1,5 -hexadiene); and significantly worse odor characteristics compared to similar alkenes, dienes, and alkynes (for example, 1 -hexene, 1- heptyne and 1,5-hexadiene). These are all desirable properties when selecting an odorant compound. [0151] EXAMPLE S
  • Dilutions of various odorants were prepared by mixing an organic compound in hydrogen gas (hydrogen class 5.0) to reach a concentration of about 120 mg/m 3 n in a gas cylinder at 100 bar.
  • the hydrogen cylinders were prepared by a gravimetric method as defined in ISO 6142.
  • the Proton-exchange Membrane Fuel Cell (PEMFC) system was manufactured by Proton Technologies in the Netherlands. The tests were performed using an 8 cm 2 cell from Proton Technologies.
  • the membrane electrode assemblies (MEA) were Proton Technologies Ames MEAs composed of 0.075 mg Pt per cm 2 (HyPer Pt/C 40%wt) for the anode and 0.3 mg Pt per cm 2 (HyPer Pt/C 40%wt) for the cathode on a Nafion 211 support.
  • the PEMFC cell Prior to testing the odorant, the PEMFC cell was purged with pure hydrogen.
  • the change of potential (e.g. voltage) at a constant 1 A/cm 2 current output correlates with the impact of the odorant on the fuel-cell performance during exposure to the odorant.
  • a reference load was measured using pure hydrogen (class 5.0) without odorant to determine the baseline performance of the MEA batch and allow comparison of the degradation effect for each odorant. Results are shown in the table below.
  • PEMFC performance with butyraldehyde shows a rapid decline in performance (as indicated by a 120 mV decrease in electrical potential) in the first 15-30 minutes, followed by a slower performance loss (100 mV decrease in electrical potential) over the remaining duration of the test period as compared to the reference test using pure hydrogen.
  • PEMFC performance with THT shows a rapid decline after 5 minutes of operation. The data clearly show that these compounds deactivate the PEMFC catalyst, which results in the decline in performance.
  • alkynes according to this disclosure are suitable odorants for stable PEMFC operation.
  • the potential (voltage) is maintained or improved over 24 hours under a 1 A/cm 2 current load.
  • the alkynes according to this disclosure have significantly better performance compared to known poisonous substances for PEMFCs, such as aldehydes (e.g. butyraldehyde) and sulfur containing compounds (e.g. THT), further demonstrating their viability as hydrogen odorant in fuel cell applications.
  • the following table shows the GC purity before and after exposure to oxygen and the peroxide level post ageing as determined by titration using the procedure defined above for the alkyne samples with or without the compounds listed in the tables above.
  • the delta between the initial and final purity by GC may be reflective of the efficiency and ability of the compounds to suppress oxidation and degradation.
  • Alkynes tested (Comparative Example 4.1-4) without antioxidant show significant degradation over the duration of the test as demonstrated by the lower purity post ageing and the increase in peroxide content.
  • THT Comparative Example 4.5
  • a commonly used gas odorant also shows a purity loss over the duration of the test. This loss is indicative of the acceptable purity losses for the alkynes if used as gas odorant.
  • any added compounds resulting in a reduction of purity of less than 1% after the ageing and/or a peroxide level below 400 ppmw are considered effective.
  • amine-based compounds such as DABCO (Example 4.34), tri ethylamine (Example 4.35) and DEHA (Example 4.39) have similar or better antioxidant properties to diphenylamine (Example 4.22-4.25), a well-known antioxidant.
  • DEHA and tri ethylamine are preferred compared to diphenylamine.
  • the concentration of amine-based antioxidant should be limited to a maximum of ca. 0.05 ppm (by mol) in the hydrogen gas phase to avoid performance issues in fuel-cell operation according the ISO 14687:2019 specifications which limit the ammonia (NH3) concentration to 0.1 ppm (by mol).
  • the alkyne odorant composition can contain a maximum of ca. 1000 ppmw amine-based antioxidant.
  • amyl acetate (example 4.40) and methyl salicylate (Example 4.52) are not effective as stabilizers or antioxidants for alkynes despite being reported as additives in gas odorant formulation based on acrylates (W02006067111A1 and W02006067115A1).
  • methyl sorbate (example 4.44) is not an effective stabilizer or antioxidant for alkynes despite equivalent sodium, calcium and potassium sorbate and sorbic acid being used as food preservatives.
  • benzyl alcohol (Example 4.53). It is a known antioxidant used in food and cosmetic applications but is not an effective stabilizer or antioxidant for alkynes.
  • isopropanol (Examples 4.10-4.15 & 4.42-4.43) and acetone (Examples 4.17-4.22) are as effective as well-known antioxidants such as BHT and BHA particularly at concentrations above 10000 ppmw.
  • antioxidants such as BHT and BHA particularly at concentrations above 10000 ppmw.
  • triethylamine, DEHA, cresols, ethylphenols, 2-methoxy-4- methyl-phenol, and 2-methoxyphenol are desirable candidates considering their physicochemical properties, e.g., low melting point and/or boiling point and reasonable vapor pressure.
  • triethylamine, DEHA, 2-ethylphenol, 3- ethylphenol, 2-methoxy-4-methyl-phenol, and 2-methoxyphenol are preferred antioxidants among those tested.
  • BHA is preferred over BHT, TBHQ, resorcinol, diphenylamine, and DABCO based on the lack of color formation after the oxidant test, low peroxide content, low byproduct formation, lower toxicity, and predicted better compatibility with fuel -cell due to absence of nitrogen atoms.
  • the maximum concentration in the odorant formulation should not exceed 1000 ppmw, and preferably be equal to or lower than 200 ppmw to comply with technical guidelines defined in ISO 13734 :2013 which require that the mass fraction of odorant residues after evaporation should be less than 0.2 wt%.
  • the odorant composition comprising the compound antioxidant may not be fully vaporized during the gas odorization process, leading to precipitation, deposition on the pipeline walls, and/or blockage or plugging of the odorant injection system.
  • gas mixture C 0.4 dm 3 of the gas mixture B was injected using a gas syringe into a second Tedlar® gas bag filled with 4.6 dm 3 of pure hydrogen gas (class 5.0) to form gas mixture C.
  • the resulting mixture C was analyzed by gas chromatography to confirm that the 1 -hexyne concentration was approximately 10 mg/Nm 3 . Due to its very low concentration in gas mixture C, the antioxidant concentration could not be accurately quantified by gas chromatography. For these tests, the antioxidant concentration in the gas mixture C should be considered equivalent to the weight ratio to its original concentration in solution A, corresponding to 0.0100 +/- 0.0015 mg/Nm 3 .
  • An olfactory panel composed of 5 panelists was used to determine the impact of the antioxidant on the olfactory properties of 1 -hexyne.
  • the panelists were exposed to a reference gas mixture made of pure 1 -hexyne and a test gas mixture including a specific antioxidant and 1 -hexyne mixture undisclosed to the panelists via two separate smelling ports. During the test, the panelists could go back and forth between both ports to determine if the antioxidant containing samples had different olfactory properties as compared to the pure 1 - hexyne reference.
  • test gas mixture was prepared by adjusting the dilution factor of each gas mixture C based on the nominal 1 -hexyne concentration as determined by gas chromatography analysis to achieve the same final concentration of 0.1 mg/m 3 1-hexyne and ca. 0.0001 mg/Nm 3 antioxidant concentration in the gas phase.
  • Each olfactory panel member was asked to give their impression of the odor character and odor strength for a test gas mixture including an undisclosed antioxidant in comparison to the pure 1-hexyne reference.
  • the panelists were asked to indicate whether they found the test gas sample to be unpleasant (e.g., would the odor cause serious concerns if smelled in a real-world application) and if the odor character and odor strength was equivalent to the pure 1-hexyne reference. If a panelist concluded that the test gas sample had equivalent odor character and strength equivalent to the pure 1-hexyne reference, the smell character of the 1- hexyne and antioxidant gas mixture C was considered equivalent to pure 1-hexyne.
  • test gas sample had either different odor character (smell was different than the pure 1-hexyne reference sample)
  • the odor character of the 1-hexyne and antioxidant gas mixture C was considered different as compared to pure 1-hexyne. If a panelist concluded that the test gas sample had different odor strength (higher or lower odor intensity), the antioxidant was considered to have synergistic effects (higher odor strength) or antagonistic effects (lower odor strength, odor masking) compared to pure 1-hexyne.
  • Results are provided in the following table.
  • A, B, C, D and E denote the feedback for each of the five individual panelists.
  • the data shows that some antioxidants had an impact on the 1-hexyne odor characteristic.
  • Example 5.1 (3 -ethylphenol), Example 5.2 (p-cresol), Example 5.4 (2-ethylphenol), and Example 5.5 (DEHA)
  • Example 5.5 DEHA
  • the effective concentration of the antioxidant in the odorant results in an effective concentration in air below the odor detection threshold to avoid odor masking or fading phenomena.
  • 10 mg/Nm 3 alkynes containing 1000 ppmw antioxidant would result, at a concentration in air of 20 % of the hydrogen LEL (i.e. 1% in air), in a concentration of 0.0001 mg/Nm 3 of antioxidant in air during a leak.
  • the odor detection threshold of the antioxidant should be significantly greater than this value to avoid its presence being detected and impacting the smell properties of the odorant. Data for example 5.3 and 5.5 to 5.8 clearly highlight such behavior.
  • compounds such as 3 -ethylphenol are not desirable antioxidant candidates due to the very low odor detection threshold.
  • the reported odor detection threshold in the literature is lower than 0.0001 mg/Nm 3 , and it is reasonable to expect that the odorant olfactive properties would be affected by such compounds as demonstrated in Example 5.1.
  • Phenolic compounds such as BHT, BHA, 2-ethylphenol, 4-ethylphenol, m-cresol, 2-methoxy-4-methylphenol, methyl salicylate, and 2-methoxyphenol are preferred considering the odor detection threshold reported in the literature.
  • amine-based compounds such as DEHA and diphenylamine are ideal candidates considering the very high odor detection threshold reported in the literature, ensuring that the odorant olfactive properties are not impacted by the presence of the antioxidant at a concentration where the antioxidant is effective. In comparison, one could use a significantly higher concentration of acetone and IPA as antioxidant due to their much higher odor detection. One of reasonable skill in the art would expect that the olfactory properties of the odorant will not be impacted even if concentrations as high as 50,000 ppmw IPA or acetone are used as antioxidant. [0178] For some applications, it is beneficial that the antioxidant enhances the alarming smell of the odorant.
  • antioxidants such as DEHA, DABCO, triethylamine, 2-methoxyphenol and 4- ethylphenol enhance the alarming characteristics of the odorant due to their highly unpleasant odor character profiles.
  • Aspect 1 An odorant for a fluid, such as a gas, the odorant comprising, consisting essentially of, or consisting of an alkene or a substituted derivative thereof, an alkyne, or a substituted derivative thereof.
  • Aspect 2 The odorant of Aspect 1, wherein the alkene is a terminal alkene, such as a terminal C3-C20 alkene, a terminal C3-C19 alkene, a terminal C3-C18 alkene, a terminal C3-C17 alkene, a terminal C3-C16 alkene, a terminal C3-C15 alkene, a terminal C3-C14 alkene, a terminal C3-C13 alkene, a terminal C3-C12 alkene, a terminal C3-C11 alkene, a terminal C3-C10 alkene, a terminal C3-C9 alkene, a terminal C3-C8 alkene, or a terminal C3-C7 alkene.
  • a terminal alkene such as a terminal C3-C20 alkene, a terminal C3-C19 alkene, a terminal C3-C18 alkene, a terminal C3-C17 alkene,
  • Aspect 3 The odorant of any of the preceding Aspects, wherein the alkene is a diene, such as a butadiene, hexadiene, heptadiene or octadiene.
  • Aspect 4 The odorant of any of the preceding Aspects, wherein the alkyne is a terminal alkyne, such as a terminal C3-C20 alkyne, a terminal C3-C19 alkyne, a terminal C3-C18 alkyne, a terminal C3-C17 alkyne, a terminal C3-C16 alkyne, a terminal C3-C15 alkyne, a terminal C3-C14 alkyne, a terminal C3-C13 alkyne, a terminal C3-C12 alkyne, a terminal C3-C11 alkyne, a terminal C3-C10 alkyne, a terminal C3-C9 alkyne, a terminal C3-C8 alkyne, or a terminal C3-C7 alkyne.
  • a terminal alkyne such as a terminal C3-C20 alkyne, a terminal C3-C19 alkyne
  • Aspect 5 The odorant of any of the preceding Aspects, wherein the alkyne is a diyne, such as a heptadiyne or octadiyne.
  • Aspect 6 The odorant of any of the preceding Aspects, wherein the odorant is an enyne, such as a heptenyne or octenyne.
  • Aspect 7 The odorant of any of the preceding Aspects, wherein the alkyne is a heptyne or a substituted derivative thereof, an octyne or a substituted derivative thereof, or a combination thereof.
  • Aspect 8 The odorant of any of the preceding Aspects, wherein the odorant is non-toxic (e.g., to humans and/or other animals).
  • Aspect 9 The odorant of any of the preceding Aspects, wherein the odorant has a detectable odor below a toxicity level (e.g., for humans and/or other animals).
  • Aspect 10 The odorant of any of the preceding Aspects, wherein the odorant is environmentally benign, such as by not posing health, toxicity, or ecological concern to humans or other animals.
  • Aspect 11 The odorant of any of the preceding Aspects, wherein the odorant, upon combustion, is environmentally benign as a combustion product, such as by not posing health, toxicity, or ecological concern to humans or other animals.
  • Aspect 12 The odorant of any of the preceding Aspects, wherein the odorant does not undesirably impact the components of a device system, such as a combustion system, fuel cell, or any other appliance (for example, the odorant does not impact, or impacts by less than 1%, or less than 0.1 %, the performance (e.g., energy output) of a device).
  • a device system such as a combustion system, fuel cell, or any other appliance
  • Aspect 13 The odorant of any of the preceding Aspects, wherein the heptyne comprises, consists essentially of, or consists of a 2-heptyne.
  • Aspect 14 The odorant of any of the preceding Aspects, wherein the heptyne comprises, consists essentially of, or consists of a 3-heptyne.
  • Aspect 15 The odorant of any of the preceding Aspects, wherein the octyne comprises, consists essentially of, or consists of a 3-octyne.
  • Aspect 16 The odorant of any of the preceding Aspects, wherein the octyne comprises, consists essentially of, or consists of a 4-octyne.
  • Aspect 17 The odorant of any of the preceding Aspects, wherein the hexadiene, heptadiene, and/or octadiene includes a compound of formula (A):
  • CH 2 CH(CH 2 ) m
  • CH CH 2 formula (A); wherein m is 2, 3 or 4 (e.g., m is 2 for a hexadiene and 4 for an octadiene).
  • Aspect 18 The odorant of any of the preceding Aspects, wherein the hexadiene heptadiene, and/or octadiene includes a compound of formula (B):
  • Aspect 19 The odorant of any of the preceding Aspects, wherein the hexadiene, heptadiene and/or octadiene includes a compound of formula (C):
  • Aspect 20 The odorant of any of the preceding Aspects, wherein the heptyne and/or the octyne comprises, consists essentially of, or consists of a compound of formula (IX):
  • Aspect 23 The odorant of any of the preceding Aspects, wherein the heptyne and/or the octyne comprises, consists essentially of, or consists of at least one of the following compounds:
  • Aspect 24 An odorant composition comprising, consisting essentially of, or consisting of the odorant of any of the preceding Aspects and an additive.
  • Aspect 25 The odorant composition of Aspect 24, wherein the additive is dispersed in the odorant, or the odorant is dispersed in the additive.
  • Aspect 26 The odorant composition of any of the preceding Aspects, wherein the additive is an odoriferous additive.
  • Aspect 27 The odorant composition of any of the preceding Aspects, wherein
  • the additive comprises, consists essentially of, or consists of methacrylic acid, an acrylic acid Ci-Ce alkyl ester, or a combination thereof; or (B) the additive does not include methacrylic acid, an acrylic acid Ci-Cs alkyl ester, or a combination thereof.
  • Aspect 28 The odorant composition of any of the preceding Aspects, wherein the additive includes a non-odiferous additive.
  • Aspect 29 The odorant composition of any of the preceding Aspects, wherein the additive is a stabilizer (i.e., a compound that prevents or delays the chemical degradation of an odorant).
  • Aspect 30 The odorant composition of any of the preceding Aspects, wherein the stabilizer comprises, consists essentially of, or consists of an antioxidant, a radical inhibitor, or a combination thereof.
  • Aspect 31 The odorant composition of any of the preceding Aspects, wherein the stabilizer comprises, consists essentially of, or consists of vitamin C or a derivative thereof (ascorbyl palmitate, ascorbyl acetate, etc.), a tocopherol or a derivative thereof (vitamin E, vitamin E acetate, etc.), vitamin A or a derivative thereof (vitamin A palmitate, etc.), a phenolic benzylamine, formic acid, acetic acid, benzoic acid, sorbic acid, butylated hydroxytoluene (tertbutyl hydroxytoluene (BHT)), butylated hydroxyanisole (BOA or BHA), 4-tert-butylcatechol (TBC), tert-butyl hydroxyanisole, 4-methoxyphenol (hydroquinone monomethyl ether (MeHQ)), 2-methoxyphenol (guaiacol), 2,6-di-tert-butyl phenol
  • Aspect 33 The odorant composition of any of the preceding Aspects, wherein the additive comprises, consists essentially of, or consists of a Cs-Cs saturated hydrocarbon (a pentane, a cyclopentane, a hexane, a cyclohexane, a heptane, a cycloheptane, an octane, and/or a fluorinated hydrocarbon, such as, for example, PFC-116, PFC-c216, PFC218, or PFC-318).
  • a Cs-Cs saturated hydrocarbon a pentane, a cyclopentane, a hexane, a cyclohexane, a heptane, a cycloheptane, an octane, and/or a fluorinated hydrocarbon, such as, for example, PFC-116, PFC-c216, PFC218, or PFC-318).
  • Aspect 34 The odorant composition of any of the preceding Aspects, wherein the heptyne is present is present in the odorant composition at an amount of at least 1 wt%, at least 5 wt%, at least 10 wt%, at least 20 wt%, at least 30 wt%, at least 40 wt%, at least 50 wt%, at least 60 wt%, at least 70 wt%, at least 80 wt%, or at least 90 wt%, based on the total weight of the odorant composition.
  • Aspect 35 The odorant composition of any of the preceding Aspects, wherein the octyne is present is present in the odorant composition at an amount of at least 1 wt%, at least 5 wt%, at least 10 wt%, at least 20 wt%, at least 30 wt%, at least 40 wt%, at least 50 wt%, at least 60 wt%, at least 70 wt%, at least 80 wt%, or at least 90 wt%, based on the total weight of the odorant composition.
  • Aspect 36 The odorant composition of any of the preceding Aspects, wherein the heptyne and the octyne are present in the odorant composition at a total amount of at least 1 wt%, at least 5 wt%, at least 10 wt%, at least 20 wt%, at least 30 wt%, at least 40 wt%, at least 50 wt%, at least 60 wt%, at least 70 wt%, at least 80 wt%, or at least 90 wt%, based on the total weight of the odorant composition (e.g., if 20 g of a heptyne and 30 g of an octyne are present in an odorant composition having a total weight of 100 g, then the heptyne and octyne are present in the odorant composition at a “total amount” of 50 wt%).
  • Aspect 37 An odorized fluid (or odorized fluid composition) comprising, consisting essentially of, or consisting of (i) a fluid, such as a gas, and (ii) the odorant of any of the preceding Aspects, or the odorant composition of any of the preceding Aspects, wherein the odorant or the odorant composition is dispersed in the fluid.
  • Aspect 38 The odorized fluid of Aspect 37, wherein the odorant or the odorant composition is evenly or unevenly dispersed in the fluid.
  • Aspect 39 The odorized fluid of any of the preceding Aspects, wherein the odorant is present in the odorized fluid at a concentration of 1,000 mg/m 3 n or less, 900 mg/m 3 n or less, 800 mg/m 3 n or less, 700 mg/m 3 n or less, 600 mg/m 3 n or less, 500 mg/m 3 n or less, 400 mg/m 3 n or less, 300 mg/m 3 n or less, 200 mg/m 3 n or less, 100 mg/m 3 n or less, 90 mg/m 3 n or less, 80 mg/m 3 n or less, 70 mg/m 3 n or less, 60 mg/m 3 n or less, 50 mg/m 3 n or less, 40 mg/m 3 n or less, 30 mg/m 3 n or less, 20 mg/m 3 n or less, or 10 mg/m 3 n or less.
  • Aspect 40 The odorized fluid of any of the preceding Aspects, wherein the odorant is present in the odorized fluid at a concentration of at least 0.5 mg/m 3 n, at least 1 mg/m 3 n, at least 2 mg/m 3 n, at least 3 mg/m 3 n, at least 4 mg/m 3 n, at least 5 mg/m 3 n, at least 6 mg/m 3 n, at least 7 mg/m 3 n, at least 8 mg/m 3 n, at least 9 mg/m 3 n, or at least 10 mg/m 3 n.
  • Aspect 41 The odorized fluid of any of the preceding Aspects, wherein the odorant is present in the odorized fluid at a concentration of about 1 mg/m 3 n to about 1,000 mg/m 3 n, about 1 mg/m 3 n to about 900 mg/m 3 n, about 1 mg/m 3 n to about 800 mg/m 3 n, about 1 mg/m 3 n to about 700 mg/m 3 n, about 1 mg/m 3 n to about 600 mg/m 3 n, about 1 mg/m 3 n to about 500 mg/m 3 n, about 1 mg/m 3 n to about 400 mg/m 3 n, about 1 mg/m 3 n to about 300 mg/m 3 n, about 1 mg/m 3 n to about 200 mg/m 3 n, about 1 mg/m 3 n to about 100 mg/m 3 n, about 1 mg/m 3 n to about 90 mg/m 3 n, about 1 mg/m 3 n to about 80 mg/m
  • Aspect 42 The odorized fluid of any of the preceding Aspects, wherein the odorant is present in the odorized fluid at a concentration of about 5 mg/m 3 n to about 5,000 mg/m 3 n, about 5 mg/m 3 n to about 2,500 mg/m 3 n, about 5 mg/m 3 n to about 1,000 mg/m 3 n, about 5 mg/m 3 n to about 900 mg/m 3 n, about 5 mg/m 3 n to about 800 mg/m 3 n, about 5 mg/m 3 n to about 700 mg/m 3 n, about 5 mg/m 3 n to about 600 mg/m 3 n, about 5 mg/m 3 n to about 500 mg/m 3 n, about 5 mg/m 3 n to about 400 mg/m 3 n, about 5 mg/m 3 n to about 300 mg/m 3 n, about 5 mg/m 3 n to about 200 mg/m 3 n, about 5 mg/m 3 n to about 100 mg
  • Aspect 43 The odorized fluid of any of the preceding Aspects, wherein the odorized fluid is a fuel for a fuel cell or other device or system.
  • Aspect 44 A method of odorizing a fluid, the method comprising, consisting essentially of, or consisting of providing a fluid, and contacting the (i) fluid, such as a gas, and (ii) the odorant of any of the preceding Aspects, or the odorant composition of any of the preceding Aspects to form an odorized fluid.
  • Aspect 45 The method or odorized fluid of any of the preceding Aspects, wherein the fluid and/or the odorized fluid is present in a fuel distribution system (such as any fuel supply infrastructure (fuel storage, fuel distribution, fuel delivery, etc.)).
  • a fuel distribution system such as any fuel supply infrastructure (fuel storage, fuel distribution, fuel delivery, etc.)
  • Aspect 46 The method of any of the preceding Aspects, further comprising disposing the fluid and/or the odorized fluid in a fuel distribution system (such as any fuel supply infrastructure (fuel storage, fuel distribution, fuel delivery, etc.)).
  • a fuel distribution system such as any fuel supply infrastructure (fuel storage, fuel distribution, fuel delivery, etc.)
  • Aspect 47 The method of any of the preceding Aspects, wherein the providing of the fluid comprises capturing the fluid.
  • Aspect 48 The method of any of the preceding Aspects, further comprising pressurizing the odorized fluid, storing the odorized fluid, or a combination thereof.
  • Aspect 49 The method of any of the preceding Aspects, wherein the odorant or the odorant composition is in a liquid phase, a gaseous phase, or a combination thereof before, during, and/or after the contacting of the fluid and the odorant.
  • Aspect 50 The method of any of the preceding Aspects, wherein the contacting of the fluid and the odorant, or the fluid and the odorant composition comprises dispensing the odorant or the odorant composition with a liquid meter.
  • Aspect 51 The method of any of the preceding Aspects, wherein the contacting of the fluid and the odorant or the odorant composition comprises nebulizing the odorant or the odorant composition.
  • Aspect 52 The method of any of the preceding Aspects, wherein the providing of the fluid comprises providing a container in which the fluid is disposed, and wherein the contacting of the fluid and the odorant or the odorant composition comprises disposing the odorant or the odorant composition in the container.
  • Aspect 53 The method of any of the preceding Aspects, wherein the providing of the fluid comprises providing a first stream comprising the fluid, and wherein the contacting of the fluid and the odorant or the odorant composition comprises contacting the first stream and a second stream comprising the odorant or the odorant composition.
  • Aspect 54 The odorant, odorant composition, odorized fluid, or method of any of the preceding Aspects, wherein the fluid is a gas (at atmospheric pressure and ambient temperature).
  • Aspect 55 The odorant, odorant composition, odorized fluid, or method of any of the preceding Aspects, wherein the fluid comprises, consists essentially of, or consists of a fuel gas.
  • Aspect 56 The odorant, odorant composition, odorized fluid, or method of any of the preceding Aspects, wherein the fluid comprises, consists essentially of, or consists of hydrogen gas (H2) or a hydrogen gas blend.
  • H2 hydrogen gas
  • Aspect 57 The odorant, odorant composition, odorized fluid, or method of any of the preceding Aspects, wherein the fluid comprises, consists essentially of, or consists of a natural or synthetic combustion gas.
  • Aspect 58 The odorant, odorant composition, odorized fluid, or method of any of the preceding Aspects, wherein the fluid comprises, consists essentially of, or consists of natural gas, LNG (liquid natural gas), liquefied petroleum gas (LPG), municipal gas, heating gas, or a combination thereof.
  • LNG liquid natural gas
  • LPG liquefied petroleum gas
  • Aspect 59 The odorant, odorant composition, odorized fluid, or method of any of the preceding Aspects, wherein the fluid comprises, consists essentially of, or consists of methane, ethane, ethene, acetylene, propane, propene, butane, isobutane, butene, pentane, or a combination thereof.
  • Aspect 60 The odorant, odorant composition, odorized fluid, or method of any of the preceding Aspects, wherein the fluid comprises consists essentially of, or consists of water gas, synthesis gas, reform gas, generator gas, coke gas, or a combination thereof.
  • Aspect 61 The odorant, odorant composition, odorized fluid, or method of any of the preceding Aspects, wherein the fluid comprises, consists essentially of, or consists of a noncombustible gas.
  • Aspect 62 The odorant, odorant composition, odorized fluid, or method of any of the preceding Aspects, wherein the fluid comprises, consists essentially of, or consists of carbon monoxide, carbon dioxide, an industrial gas (e.g., nitrogen (N2), oxygen (O2), argon, helium, etc.), or a combination thereof.
  • Aspect 63 A method of generating energy, the method comprising, consisting essentially of, or consisting of providing a fuel cell, the fuel cell comprises an anode; and contacting the anode and the odorized fluid of any of the preceding Aspects.
  • Aspect 64 The method of Aspect 63, wherein the contacting of the anode and the odorized fluid produces an oxidized odorized fluid.
  • Aspect 65 The method of any of the preceding Aspects, further comprising removing the odorant from the odorized fluid, wherein, optionally, the removing of the odorant is performed at least in part with any of the apparatuses or techniques provided herein, including, but not limited to, the use of catalytic decomposition, an adsorption media, an absorption media, a water trap, a solvent trap, etc.
  • Aspect 66 The method of any of the preceding Aspects, further comprising removing the odorant from the oxidized odorized fluid, wherein, optionally, the removing of the odorant is performed at least in part with any of the apparatuses or techniques provided herein, including, but not limited to, the use of catalytic decomposition, an adsorption media, an absorption media, a water trap, a solvent trap, etc.
  • a method of removal comprising providing the odorized fluid or the oxidized odorized fluid of any of the preceding Aspects; contacting the odorized fluid or the oxidized odorized fluid and a removal substrate or scrubber; wherein the removal substrate or scrubber reduces an amount of the odorant in the odorized fluid or the oxidized odorized fluid by adsorption, absorption, or chemical reaction by the use of catalytic decomposition, an adsorption or absorption media, a water trap, or a solvent trap to produce a deodorized fluid; wherein, optionally, the removal substrate or scrubber reduces the amount of the odorant in the odorized fluid or the oxidized odorized fluid by at least 80 %, at least 85 %, at least 90 %, at least 95 %, at least 99 %, at least 99.9 %, or 100 % (e.g., if the amount of odorant is reduced by 90 %, then a
  • Aspect 68 The method of any of the preceding Aspects, wherein the odorant or the odorant composition is at least partially consumable by the fuel cell, thereby optionally improving the performance of the fuel cell, increasing the energy produced by the fuel cell, or a combination thereof relative to a fuel cell operated with the fluid of the odorized fluid in the absence of the odorant or the odorant composition.
  • Aspect 69 The method of any of the preceding Aspects, wherein the odorant or the odorant composition is at least partially consumable by the fuel cell, thereby optionally improving the performance of the fuel cell, increasing the energy produced by the fuel cell, or a combination thereof relative to a fuel cell operated with the fluid of the odorized fluid in the absence of the odorant or the odorant composition.
  • an amount of the odorant in the deodorized fluid is less than a critical concentration
  • the critical concentration is a concentration of the odorant that, if exceeded, undesirably impacts the performance of an apparatus or a process in which the deodorized fluid is used, or to which the deodorized fluid is subjected.
  • Aspect 70 The method of any of the preceding Aspects wherein the deodorized fluid is used in and/or subjected to a fuel cell, a chemical process (e.g., hydrogenation and reduction reactions, metal hydride synthesis); petrochemical process (e.g.
  • hydrocracking, reforming, desulfurization steel production process (for example, using direct reduced iron (DRI)); glass production process; semiconductor and electronic production process (including cleaning, annealing, epitaxy, doping, ion implantation, passivation, chemical vapor deposition (CVD), physical vapor deposition (PVD), atomic layer deposition (ALD), plasma etching, atomic layer etching (ALE), diborane and digermane stabilization, and generating EUV light sources); cement production process; a pharmaceutical production process, a food and beverage production process, a heat generation (e.g., combustion or catalytic) process, or a mechanical power generation (e.g., combustion) process and other emerging technologies or process requiring a deodorized fluid, or a combination thereof.
  • CVD chemical vapor deposition
  • PVD physical vapor deposition
  • ALD atomic layer deposition
  • ALE atomic layer etching
  • diborane and digermane stabilization and generating EUV light sources
  • Aspect 71 A system comprising (i) a sensor, and (ii) the odorant or the odorant composition of any of the preceding Aspects.
  • Aspect 72 The system of Aspect 71, wherein the sensor is coupled to, or configured to be coupled to, a fuel supply, a fuel cell, another component of a fuel cell system, any appliance that uses hydrogen as fuel, or any component of an appliance that uses hydrogen as fuel.
  • Aspect 73 The system of any of the preceding Aspects, wherein the sensor comprises circuitry programmed to shut down a fuel cell, an appliance, or other system or component thereof in the event of a leak.
  • Aspect 74 The system of any of the preceding Aspects, wherein the sensor is configured to permit the use of any of the odorants of the preceding Aspects at a concentration that is not detectable by an average human.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des substances odorantes et des compositions de substances odorantes qui comprennent un hexyne, un heptyne ou un octyne, tel qu'un 1-hexyne, un 2-hexyne, un 2-heptyne, un 3-heptyne, un 3-octyne ou un 4-octyne. L'invention concerne des procédés d'odorisation d'un matériau, tel qu'un fluide. Le fluide peut être un gaz, tel que l'hydrogène gazeux, le méthane gazeux, ou une combinaison de ceux-ci. L'invention concerne des fluides odorants qui comprennent un fluide et une substance odorante ou une composition de substances odorantes. L'invention concerne également des procédés de génération d'énergie qui peuvent comprendre la mise en contact d'une anode d'une pile à combustible avec un fluide odorant qui comprend une substance odorante et de l'hydrogène gazeux, du méthane gazeux, ou une combinaison de ceux-ci. L'invention concerne des systèmes qui comprennent une substance odorante ou une composition de substances odorantes, et un capteur.
PCT/US2025/023542 2024-04-09 2025-04-08 Substances odorantes pour fluides, fluides odorants, procédés et systèmes Pending WO2025217091A1 (fr)

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US202463631534P 2024-04-09 2024-04-09
US202463631556P 2024-04-09 2024-04-09
US63/631,534 2024-04-09
US63/631,556 2024-04-09

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