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WO2017172882A1 - Matériaux de filtration de type mousse à base de pyridazine et de pyridazinone pour l'élimination des nucléophiles, des électrophiles, et des métaux - Google Patents

Matériaux de filtration de type mousse à base de pyridazine et de pyridazinone pour l'élimination des nucléophiles, des électrophiles, et des métaux Download PDF

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Publication number
WO2017172882A1
WO2017172882A1 PCT/US2017/024702 US2017024702W WO2017172882A1 WO 2017172882 A1 WO2017172882 A1 WO 2017172882A1 US 2017024702 W US2017024702 W US 2017024702W WO 2017172882 A1 WO2017172882 A1 WO 2017172882A1
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WIPO (PCT)
Prior art keywords
medium
filtration material
nucleophile
polymer
polymer filtration
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Ceased
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PCT/US2017/024702
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English (en)
Inventor
Douglas A. LOY
Robb E. BAGGE
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University of Arizona
Arizona's Public Universities
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University of Arizona
Arizona's Public Universities
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Publication of WO2017172882A1 publication Critical patent/WO2017172882A1/fr
Anticipated expiration legal-status Critical
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/28—Treatment of water, waste water, or sewage by sorption
    • C02F1/288—Treatment of water, waste water, or sewage by sorption using composite sorbents, e.g. coated, impregnated, multi-layered
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds
    • B01J20/264—Synthetic macromolecular compounds derived from different types of monomers, e.g. linear or branched copolymers, block copolymers, graft copolymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
    • B01J20/28042—Shaped bodies; Monolithic structures
    • B01J20/28045—Honeycomb or cellular structures; Solid foams or sponges
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/28—Treatment of water, waste water, or sewage by sorption
    • C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2220/00—Aspects relating to sorbent materials
    • B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
    • B01J2220/49—Materials comprising an indicator, e.g. colour indicator, pH-indicator
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/10—Inorganic compounds
    • C02F2101/101—Sulfur compounds
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/10—Inorganic compounds
    • C02F2101/20—Heavy metals or heavy metal compounds
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2101/00—Nature of the contaminant
    • C02F2101/30—Organic compounds
    • C02F2101/38—Organic compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2303/00—Specific treatment goals
    • C02F2303/02—Odour removal or prevention of malodour

Definitions

  • the present invention relates to pyridazine- and pyridazinone-based polymer foams effective for removal of nucleophilic and electrophilic chemicals and metals.
  • Pyridazine and pyridazinone based polymer foam synthesized from a Carboni- Lindsey reaction between substituted tetrazine species and polydienes can be used for the effective removal of both electrophilic and nucleophilic chemicals, as well as metals, in their gaseous, liquid and solid states.
  • polydienes include, but are not limited to, poiybutadiene, polyisoprene, and polychloroprene, !n
  • a foam generated by the reaction of a tetrazine having a ieaving group substitution and a polydiene creates an open-celled porous network which contains reactive sights to trap nucieophilic species (i.e.
  • the substituted tetrazine may be reacted with an alkene-containing polymer to generate a foam.
  • the substituted tetrazine may be reacted with an alkyne-containing polymer to generate a foam.
  • the foam materia! can advantageously change color upon reaction with nucieophilic species and be used as a coiorimetric indicator for determining exposure levels to these species.
  • the material can be modified to filter eiectrophilic species and sequester carbon dioxide and metals, such as mercury, by reacting the foams with amines (ammonia, diamines, multi-amine organics) and/or hydrogen sulfides.
  • amines ammonia, diamines, multi-amine organics
  • hydrogen sulfides such as mercury
  • the present invention may be used in many applications including, but not limited to, lab safety, odor control (water treatment systems, uptake of hydrogen sulfides and amines), chemical warfare agent filtration, and mine safety. None of the presently known prior references or work has the unique inventive technical feature of the present invention.
  • FIG. 1 shows a reaction schematic for the post-functionaiization of foams and nucleophile trapping. Pyridazine substituents can be altered after formation through exposure to a liquid or gaseous nucleophile. Foam samples before and after trapping an amine illustrate the colorimetric indication of the foam,
  • harmful substance may refer to a substance that is toxic to mammals, e.g. human, and that may cause infections or allergic reactions when exposed to said substance.
  • the harmful substances may be contained is a medium such as dust, gasses, or fumes that may be inhaled, or liquids that are consumed, or fluids, gels, or powders that come into direct contact with a person's body.
  • the haiides may refer to carcinogenic alkylating agents such as, for example, mustards, alkyi haiides, benzyl haiides, and ally! haiides.
  • the metals may be any metal cationic species.
  • the metals may have enhanced activity with a dicationic or tricationic main group, transition metals, or f- block metals.
  • the metals can include zero valent, monovalent, and multivalent metals.
  • the metals can be radioactive and nonradioactive.
  • the metal may be from any group of the periodic table for example, a transition metal, an alkali or alkaline earth, a heavy metal, or a rare earth metal.
  • Specific metals can include, but are not limited to: copper (Cu), nickel (Ni), zinc (Zn), lead (Pb), mercury (Hg), cadmium (Cd), silver (Ag), iron (Fe), manganese (Mn), palladium (Pd), platinum (Pt), strontium (St), selenium (Se), arsenic (As), cobalt (Co), tungsten (W), and gold (Au).
  • the transition metal may be a base metal active as a catalyst or catalyst promoter such as Ni, Co or W.
  • the metal may be contaminants such as various copper, nickel, zinc, cobalt, chromium, and iron species,
  • nucleophile refers to a molecule or ion that donates a pair of electrons to form a new covalent bond.
  • a nucleophile is also known as a Lewis base.
  • An electrophile is a molecule or ion that accepts a pair of electrons to make a new covalent bond.
  • An electrophile is also known as a Lewis acid.
  • the term "chelate” refers to the formation of a heterocyclic ring containing a metal ion attached by coordinate bonds to at least two nonmetai ions.
  • the present invention utilizes polymers to remove nucleophiles and electrophiles by chemically reacting them with reactive functional groups in polymers bearing dihydropyridazine or dihydropyridazinone substituents.
  • the iminyi groups with halide or amine leaving groups of the dihydropyridazine or dihydropyridazinone can react with nucleophiles.
  • the electrophile scavenging materials can have pendant nucleophilic or Lewis base groups placed through modification of the tetrazine-precursor or the dihydropyridazine-modified polymer with a nucleophilic species.
  • a polymer filtration material for scavenging a nucleophile, an electrophile, or a metal from a medium is prepared from a polymer backbone having a plurality of alkene functional groups, and a plurality of tetrazine monomers, each having at least one leaving group.
  • each tetrazine monomer can react with one of the alkene functional groups of the polymer backbone via a Carboni-Lindsey reaction, thereby forming a pyridazine moiety attached to the polymer backbone.
  • the polymer filtration material is in the form of a foam.
  • the present invention features a method of producing a polymer filtration material for scavenging a nucleophile, an electrophile, or a metal from a medium.
  • the method may comprise providing a polymer backbone having a plurality of alkene functional groups, providing a plurality of tetrazine monomers, each tetrazine monomer having at least one leaving group, and reacting the tetrazine monomers with the polymer backbone.
  • each tetrazine monomer reacts with one of alkene functional groups of the polymer backbone via a Carboni-Lindsey reaction to form a pyridazine moiety attached to the polymer backbone, thereby producing the polymer filtration material.
  • the polymer filtration material is in the form of a foam.
  • the polymer filtration material is formed in about 30 minutes to 1 hour of reacting the tetrazine monomers with the polymer backbone.
  • the method may be performed at a temperature range of about 10°C to 40°C.
  • At least one equivalent of nitrogen gas can be produced during the reaction of the tetrazine and the polymer backbone for every equivalent of tetrazine used.
  • a carbon dioxide gas is not produced during the reaction of a tetrazine component and a polymeric component unlike during the production of poiyurethane. Therefore, the polymer filtration material formed can be considered as a greener material than polyurethanes, and the resulting foams provide an alternative to polyurethanes.
  • the polymer backbone may be a polydiene, a poiybutadiene, a polyisoprene, or a poiychioroprene.
  • Non-limiting examples of the polymer backbone are as follows:
  • the pyridazine moiety may be a dihydropyridazine or a dihydropyridazinone.
  • the leaving group may be a halide, trifiuoromethanesulfonate, tosylate, amine, diamine, pyrazole, hydrazine, thiol, ester, carboxylate, heteroaromatic, phenyl, alkyi ether, or thioether.
  • the tetrazine monomer may further comprise a second leaving group or an unreactive group.
  • the tetrazine monomer may be according to the following: where Ri is a halide, trifiuoromethanesulfonate, tosylate, amine, diamine, pyrazole, hydrazine, thiol, ester, carboxylate, heteroaromatic, phenyl, alky! ether, or thioether, and where f3 ⁇ 4 is a second leaving group or an unreactive group.
  • the polymer filtration material has a colorimetric indication such that the polymer filtration material can change color when capturing the nucleophile, the electrophile, or the metal from the medium.
  • the colorimetric indicator may be effective to determine a level of exposure to the metals, the electrophiiic chemicals, or the nucleophilic chemicals.
  • the medium is in a gaseous, liquid, or solid state.
  • the present invention features a method of removing a nucleophilic, electrophilic, or metal contaminant from a medium.
  • the method may comprise contacting the medium with any one of the polymer filtration materials described herein.
  • the present invention features a method of removing odors emanating from a medium, such as air or aqueous waste streams.
  • the method may comprise contacting the medium with any one of the polymer filtration materials described herein.
  • the present invention features a method of removing chemical warfare agents from a medium, such as air or potable water.
  • the method may comprise contacting the medium with any one of the polymer filtration materials described herein.
  • a nucleophile scavenging reagent also referred to herein as a nucleophile getter
  • a nucleophile getter may be a polymer prepared by reacting tetrazines with alkenyl bonds of polymers to form a dihydropyridazine group that can react with nucleophilic species.
  • Non-limiting examples of preparing the polymer are shown in Schemes 1 -3.
  • a second substituenf may be a halide (i.e. F, CI, Br, I, Ts, Tf), an amine, or an unreactive group, such aryls, aikyls, aikenyls, ethers, thiol ethers, esters, amides, or cyanides.
  • Scheme 1 Non-limiting example of a reaction schematic for synthesizing filtration materials.
  • R include, but are not limited to, halides, pyrazoies, hydrazines, amines, diamines, thiols, esters, carboxylates, heteroaromatics, phenyls, aikyl ethers, and thioethers.
  • the leaving group is configured to react with the nucleophiie or the electrophile, thereby removing the nucleophiie or the electrophile from the medium.
  • the leaving group can undergo a substitution reaction with the nucleophiie or electrophile, thereby forming a nucleophiie or electrophile substituted material.
  • the nucleophiie or electrophile substituted material is configured to further undergo a substitution reaction with another electrophile or nucleophiie of a second medium, thereby removing the other electrophile or nucleophiie from the second medium.
  • a nitrogen group of the pyridazine moiety such as the iminyl nitrogen or the enaminyi nitrogen, is configured to react with the nucleophiie or the electrophile, thereby removing the nucleophiie or the electrophile from the medium.
  • a nucleophiie can be removed from air or water or solvent by attacking the iminyl group and replacing the haiide or amine group, or by reacting with the iminyl nitrogen or the enaminyi nitrogen, thereby resulting in the nucleophilic group being covendingiy attached to the polymer bearing the scavenging group.
  • nucleophiies can change the physical properties of the polymer. For example, in soluble versions of the nucleophiie scavenging polymer, this can lead to precipitation or gelation of the polymer that can assist in sequestration of the nudeophi!es to remove them more effectively from the environment.
  • an electrophiie scavenging reagent also referred to herein as an electrophiie getter
  • an electrophiie getter may be a polymer with dihydropyridazine or dihydropyridazinone groups having a nudeophi!ic or Lewis base groups that can scavenge electrophiles, such as metal ions, alkyi haiides, or carbon dioxide.
  • these electrophiie getters can be prepared by replacing a halide or amine leaving group in the same polymers used for nucieophile getters with groups bearing one or more amines, thiols, thiol ethers, or mixtures thereof.
  • substitutions can be done in the tetrazines used to prepare the polymers, or in the dihydropyndazine modified polymers.
  • binding with electrophiles may also cause physical properties of the polymer to change and can lead to gelation or precipitation, which can further aid in sequestration of the targeted chemical.
  • Scheme 5 A non-limiting example of a polymer with a diamine ligand used to intercept alkyi haiides, metals, and acidic gasses such as carbon dioxide, hydrogen sulfide or hydrogen cyanide, according to an embodiment of the present invention.
  • the present invention does not use pyridy! groups as a substituent that can scavenge meta! ions or Lewis acids.
  • Pyridyl groups may be used as a second substituent, but they are not necessary for use in trapping chemical species.
  • the nitrogen moiety of the pyridyl may be in the meta or para position with respect to the tetrazine, and not necessarily in the ortho position.
  • Scheme 6 A non-limiting schematic for the nucleophiie trapping of amines, alkoxides and hydrogen sulfide according to an embodiment of the present invention.
  • the solid filtration material is effective to sequester carbon dioxide upon reaction of an amine functional group of the filtration material with an electrophilic carbon atom of the carbon dioxide molecule.
  • the carbon dioxide is sequestered by converting the amine functional group to a carbamic acid functional group.
  • the solid filtration material functions to filter electrophilic species and traps the electrophilic species by converting the nucleophilic group (such as amines) into isocyanate.
  • Scheme 7 A non-limiting schematic representation of carbon dioxide sequestration, and electrophiie and nucieophiie trapping according to an embodiment of the present invention.
  • n ranges from about 5-10,000
  • p ranges from about 5-10,000
  • m ranges from about 5-10,000.
  • the polymer filtration material is further configured to chelate the metal, namely, via the leaving groups or the substituting groups, chelating the metal, thereby removing the metal from the medium.
  • the dihydropyridazine or dihydropyridazinone does not participate directly in the metal chelation, i.e. the nitrogen moiety does not form coordinate bonds to the metal. As shown in Scheme 8, at least two leaving groups of the polymer filtration material can chelate the metal.
  • the nucleophile or eiectrophile substituted material can be used to chelate the metal using at least two groups of the nucleophile or eiectrophile substituents, as shown in Scheme 9.
  • the nucleophile or eiectrophile substituted material can form a metal adduct complex with the metal to function as a metal waste collecting sponge.
  • Scheme 9 A non-limiting schematic representation of metal waste collection accordin to an embodiment of the present invention.
  • the filtration material may be according to any of the following structures:
  • the filtration material may be according to any of the following structures:
  • nucleophile substituted filtration material formed by the nucleophilic substitution reaction of the filtration material may be according to any of the followin structures:
  • the nucleophilic groups may be amines, aikoxides, hydroxyls, or thiols.
  • the electrophiie substituted filtration material formed by the electrophilic substitution reaction of the filtration material may be according to any of the following structures:
  • the metal adduct complex formed by the nudeophiie substituted filtration materia! and the metal may be according to any of the following structures:
  • the nucleophilic groups may be amines, alkoxides, hydroxyis, or thiols.
  • the metal adduct complex formed by the electrophile substituted filtration material and the metal comprising at least one or more of the following structures:
  • the method of making a solid composition may comprise adding a tetrazine component as a diene of the Diels-Alder reaction in a reaction vessel and adding the polymeric component as a dienophiie of the Diels-Alder reaction in the same reaction vessel. Then the tetrazine component and the polymeric component are mixed to generate a foam which functions as a filtration material.
  • nucleophiie trapping using an embodiment of the present invention. Equivalents or substitutes are within the scope of the invention.
  • FT-IR (ATR, Si0 2 ): cm “1 - 3207.97, 3004.55, 2923.88, 2852.31 , 1680.39, 1446.23, 1409.48, 1310.72, 1252.57, 1217.44, 1 179.96, 1 155.38, 1074.78, 994.93, 969.40, 915.83, 826.28, 744.54, 723.23, 666.64, 625.94, 610.60, 592.06, 568.10, 545.15, 501 .66, 477.84, 433.79, 416.40.
  • Poly(pyridazine-co-butadiene) foam material (0.095 g) was placed into a 25 mL beaker. The beaker was then placed into a 250 mL beaker containing ammonium hydroxide (20 mL) which was subsequently covered with parafiim to seal in the gaseous ammonia fumes. After five minutes, the foam's color had changed from a light peach color to dark brown, and the material had no observed change in mass (0.095 g).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental & Geological Engineering (AREA)
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Abstract

L'invention concerne des mousses à base de pyridazine et de pyridazinone synthétisées par une réaction de Carboni-Lindsey. Ces mousses peuvent être fabriquées à partir de matériaux de départ bon marché et sont efficaces pour éliminer à la fois les produits chimiques nucléophiles et électrophiles, les substances nocives, et les métaux. Elles peuvent également être utilisées comme indicateur colorimétrique pour déterminer le niveau d'exposition à des substances nocives. Les applications desdites mousses comprennent la sécurité des laboratoires, la lutte contre les odeurs, la filtration des agents de guerre chimique et la sécurité des mines.
PCT/US2017/024702 2016-03-29 2017-03-29 Matériaux de filtration de type mousse à base de pyridazine et de pyridazinone pour l'élimination des nucléophiles, des électrophiles, et des métaux Ceased WO2017172882A1 (fr)

Applications Claiming Priority (2)

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US201662314813P 2016-03-29 2016-03-29
US62/314,813 2016-03-29

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WO2017172882A1 true WO2017172882A1 (fr) 2017-10-05

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004047568A1 (fr) * 2002-11-26 2004-06-10 Philip Morris Products, S.A. Poudres inorganiques a selectivite pour le monoxyde de carbone, hcn ou no
US20040262217A1 (en) * 2002-02-07 2004-12-30 Bridgestone Corporation Fluid cleaning filter and filter device
US6866045B1 (en) * 1999-09-13 2005-03-15 Sun Zero Filtration method and filter consisting of nitrogen-containing cycles or heterocycles such as DNA or RNA
US20110171076A1 (en) * 2008-02-21 2011-07-14 3M Innovative Properties Company Adducts of amines and polycarboxylic acids, and filter media comprising such adducts
US20140113844A1 (en) * 2012-10-24 2014-04-24 Exxonmobil Research And Engineering Company Functionalized polymers and oligomers as corrosion inhibitors and antiwear additives

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6866045B1 (en) * 1999-09-13 2005-03-15 Sun Zero Filtration method and filter consisting of nitrogen-containing cycles or heterocycles such as DNA or RNA
US20040262217A1 (en) * 2002-02-07 2004-12-30 Bridgestone Corporation Fluid cleaning filter and filter device
WO2004047568A1 (fr) * 2002-11-26 2004-06-10 Philip Morris Products, S.A. Poudres inorganiques a selectivite pour le monoxyde de carbone, hcn ou no
US20110171076A1 (en) * 2008-02-21 2011-07-14 3M Innovative Properties Company Adducts of amines and polycarboxylic acids, and filter media comprising such adducts
US20140113844A1 (en) * 2012-10-24 2014-04-24 Exxonmobil Research And Engineering Company Functionalized polymers and oligomers as corrosion inhibitors and antiwear additives

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