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WO1989005339A1 - Additifs pour l'essence ameliorant l'indice d'octane - Google Patents

Additifs pour l'essence ameliorant l'indice d'octane Download PDF

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Publication number
WO1989005339A1
WO1989005339A1 PCT/US1988/004257 US8804257W WO8905339A1 WO 1989005339 A1 WO1989005339 A1 WO 1989005339A1 US 8804257 W US8804257 W US 8804257W WO 8905339 A1 WO8905339 A1 WO 8905339A1
Authority
WO
WIPO (PCT)
Prior art keywords
gasoline
octane
gal
lead
ethanol
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.)
Ceased
Application number
PCT/US1988/004257
Other languages
English (en)
Inventor
William J. Wells, Iii
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.)
CHEMICAL FUELS Corp
Original Assignee
CHEMICAL FUELS Corp
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 CHEMICAL FUELS Corp filed Critical CHEMICAL FUELS Corp
Publication of WO1989005339A1 publication Critical patent/WO1989005339A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/10—Use of additives to fuels or fires for particular purposes for improving the octane number
    • 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
    • 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
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • 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
    • C10L1/30—Organic compounds compounds not mentioned before (complexes)
    • C10L1/305—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond)
    • 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
    • C10L1/30—Organic compounds compounds not mentioned before (complexes)
    • C10L1/305—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond)
    • C10L1/306—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond) organo Pb compounds

Definitions

  • the present invention relates to an improved method for the elevation of the octane index of motor gasoline by oxygenated hydrocarbons in combination with organometallic compounds.
  • Oxygenated hydrocarbons such as alcohols and organometallics, in particular tetraethyl lead, have been used to raise the octane index of gasoline for many years.
  • organomanganese compounds alone or in combination with organolead compounds, have been used to improve the octane index of gasolines for use in combustion engines. See, for example, U.S. Patent Nos.
  • the present invention is a method, and the product thereof, to increase the octane index of gasoline through the use of a combination of oxygenated hydrocarbons and organometallic compounds.
  • a gasoline mixture is prepared containing between 75 to 95% unleaded gasoline, 5 to 25% oxygenated, hydrocarbons such as alcohols of less than 5 carbons, between about 0.05 g to 4 g Pb/gal and between about 0.005 g to 0.15 g Mn/gal.
  • the actual percentages of oxygenated hydrocarbons and organometallic compounds which are added may be optimized as necessary to produce the desired increase in octane using empirical methods similar to the procedures used in the following examples.
  • the preferred alcohol composition consists of between 33 to 100% denatured ethyl alcohol and 0 to 67% methyl alcohol and makes up between 7.5 and 10% by volume of the gasoline mixture.
  • oxygenated hydrocarbons of fewer than 5 carbons which can be used in place of, or in addition to, ethanol and methanol include isomers of propanol and butanol, methyl tertiary-butyl ether (MTBE) and tertiary-amyl methyl ether (TAME) .
  • Acceptable sources of lead and manganese include organolead compounds such as tetraalkyl lead compounds, espeially tetraethyl lead, and derivatives thereof, and organomanganese compounds such as methylcyclopentadienyl manganese tricarbonyl.
  • organolead compounds such as tetraalkyl lead compounds, espeially tetraethyl lead, and derivatives thereof
  • organomanganese compounds such as methylcyclopentadienyl manganese tricarbonyl.
  • the preferred quantities of both lead and manganese are in the range of 0.1 mg metal/gallon
  • the present invention resides in using a combination of an octane-enhancing blend of alcohols or other oxygenated hydrocarbons and organometallic compounds containing manganese and lead.
  • the manganese alone or in combination with the lead, acts in combination with the alcohols to increase the octane index of the gasoline.
  • the preferred embodiment at the present time is the combination of the oxygenated hydrocarbons, organolead compounds and organomanganese compounds. It may be desirable to provide other additives enhancing performance of the gasoline mixture including carburetor detergents, deposit control agents, fuel intake system cleaners, port fuel injector cleaners, corrosion inhibitors to prevent chemical attack by the oxygenated hydrocarbons on lead and zinc alloys, corrosion inhibitors to prevent conventional rusting by dissolved oxygen in the aqueous phase in the event of a phase separation, and oxidative stabilizers.
  • the octane index is derived by determining the "research octane” value and the "motor octane” value and then determining the average octane value of the two.
  • the research octane is the value derived during combustion of the gasoline under low stress, normal operating temperatures and the motor octane is the value derived during combustion of the gasoline under high stress, pressure and temperature. The procedures for making these measurements are well known to those skilled in the art.
  • the oxygenated hydrocarbons and organometallic compounds are added to a gasoline base stock.
  • a gasoline having the lowest possible octane is utilized since this is the most economical starting material.
  • a gasoline mixture having an effective octane index of between 87 and 89 can be produced according to the present invention from a suitable suboctane gasoline having an octane index of (R+M)/2 in the range of between 83 to 84 (Examples 1 and 2) .
  • gasolines and combinations of gasoline and usable refinery blending components may be utilized in the present invention.
  • an 87 octane unleaded gasoline can be used as the base stock for a mixture containing 10% ethanol, 0.1 g Pb/gal., and 0.1 g Mn/gal.
  • This leaded gasohol has an octane rating of 91.55, far in excess of the 89 octane rating required by most state regulatory agencies for leaded gasohol (Example 3) .
  • a blender might mix 90% unleaded gasoline with 10% raffinate to produce a lower octane gasoline base stock. To this new base stock, the blender would then add the alcohol mixture such that the final gasoline meets all of the regulatory specifications and contains 5% methanol, 2.5% ethanol, 0.1 g Pb/gal. , 0.1 g Mn/gal. , and an additive package consistent with the Du Pont Waiver to the Clean Air Act.
  • additives should not be blended with the gasoline mixture which would cause the gasoline to exhibit poor performance at the hands of the consumer.
  • the alcohols preferred for use with this invention include methanol, the two isomers of propanol and the four isomers of butanol, all alcohols of fewer than five carbons. These alcohols have been added to gasoline in percentages ranging up to 15% in the U.S. and up to 25% in Brazil without modification of the automobile. In the U.S., the Environmental Protection Agency now limits the amount of total alcohol in gasoline to a maximum of 10%.
  • MTBE methyl tertiary- butyl ether
  • TAME tertiary-amyl methyl ether
  • TEL tetraethyl lead
  • EDC ethylene dichloride
  • Other lead carriers known to those skilled in the art may also be utilized. Care should be taken to avoid excessive lead quantities since the lead containing compounds, and combustion products, are toxic.
  • Manganese is added to yield up to 0.15 g Mn/gallon. Higher levels cause engine fouling.
  • the only compound used commercially at the present time as a source of manganese in gasoline is methylcyclopentyldienyl manganese tricarbonyl (MMT) . While use of MMT in the United States has been restricted to leaded gasoline due to concerns that manganese, like lead, might foul catalytic converters, MMT is used in combination with unleaded gasoline in Canada. It is therefore possible that the combination of alcohol and MMT might be useful in the production of higher octane unleaded gasoline.
  • the increase provided by alcohol is lower in the presence of lead.
  • 0.1 g Pb/gal increases the octane index by about 1.
  • 0.1 g Mn/gal increases the octane index about 1 or more.
  • the combination of 0.1 g Pb/gal and 0.1 g Mn/gal in gasoline in the absence of alcohols increases the octane index by about 2 to 3.
  • the present invention is further demonstrated by the following non-limiting examples. All percentages are by volume unless otherwise specified.
  • the advantage of the present invention over the use of either lead or alcohol to increase the octane of motor gasoline is demonstrated by these examples.
  • the octane index was determined for the base gasoline composition.
  • the mixture, containing gasoline, oxygenated hydrocarbons, and organometallic compounds, was prepared and the octane value determined.
  • the effect of the additives is illustrated by the difference between the two numbers.
  • TEL tetraethyl lead
  • MMT methylcyclopentadienyl manganese tricarbonyl
  • BOV blending octane value
  • Example 3 Comparison of the effect of Ethanol and Methanol on a higher octane unleaded gasoline.
  • a base gasoline having a fungible 87 octane index was used to compare the effect of 10% Ethanol, 5% Methanol + 2.5% Ethanol, and 0.1 g Pb/gal in combination with 0.1 g Mn/gal, as shown in Table 5.
  • the significance of the effect of combining the alcohol, manganese, and lead with the base gasoline is that, in contrast to the prior art, it allows the refiner to produce a base gasoline for manufacture of his leaded 89 octane grade gasoline which is one to two octane numbers lower than would have been expected; that is, the base gasoline need only be about 83 octane rather than an expected 85 octane.
  • These saved octane numbers result in superior economics for the leaded grade and allow additional manufacture of higher octane, value added premium unleaded gasolines, especially for refiners who are octane short in their conventional petroleum refining configuration and do not want to invest in new crude oil processing equipment.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Combustion & Propulsion (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

L'invention concerne un procédé et un produit permettant d'augmenter l'indice d'octane de l'essence par l'utilisation d'une combinaison d'hydrocarbures oxygénés et de composés organométalliques. Un mélange d'essence est préparé et contient entre 75 et 95% d'essence sans plomb, entre 5 et 25% d'hydrocarbures oxygénés tels que des alcools ayant moins de 5 atomes de carbone, entre 0,05 g environ et 4 g Pb/gal et entre 0,005 g et 0,15 g Mn/gal. Les pourcentages d'alcool et de composés organométalliques ajoutés peuvent être optimalisés en fonction des besoins pour produire l'augmentation désirée d'octanes par des procédés empiriques semblables aux procédés utilisés dans les exemples suivants. La composition d'alcool préférée comprend entre 33 et 100% d'alcool éthylique dénaturé et entre 0 et 67% d'alcool méthylique et constitue entre 7,5 et 10% en volume du mélange d'essence. D'autres hydrocarbures oxygénés ayant moins de 5 carbones qui peuvent être utilisés à la place de l'éthanol et du méthanol ou qui peuvent être utilisés en plus de l'éthanol et du méthanol comprennent des isomères de propanol et de butanol, l'éther de méthyle tertiaire-butyle (MTBE) et l'éther de méthyle tertiaire-amyle (TAME). Des sources acceptables de plomb et de manganèse comprennent des composés d'organo-plomb tels que les composés de plomb tétra-alkyle, spécialement le plomb tétra-éthyle, et leurs dérivés, et des composés d'organomanganèse tels que le méthylcyclopentadiényle manganèse tricarbonyle. Les quantités préférées de plomb et de manganèse sont de l'ordre de 0,1 mg de métal par gallon d'essence.
PCT/US1988/004257 1987-12-03 1988-11-29 Additifs pour l'essence ameliorant l'indice d'octane Ceased WO1989005339A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12828387A 1987-12-03 1987-12-03
US128,283 1993-09-29

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Publication Number Publication Date
WO1989005339A1 true WO1989005339A1 (fr) 1989-06-15

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0435631A1 (fr) * 1989-12-22 1991-07-03 Ethyl Petroleum Additives Limited Compositions de combustible diesel
EP0667387A3 (fr) * 1994-02-10 1995-09-27 Ethyl Corp
US5944858A (en) * 1990-09-20 1999-08-31 Ethyl Petroleum Additives, Ltd. Hydrocarbonaceous fuel compositions and additives therefor
KR100351794B1 (ko) * 2001-06-01 2002-09-05 주식회사 서현케미칼 옥탄가를 증대시키는 연료 첨가제
CN101886004A (zh) * 2010-07-12 2010-11-17 山东亿源石化有限公司 一种甲醇汽油添加剂及其配制的甲醇汽油以及它们的生产方法
CN102093918A (zh) * 2009-12-11 2011-06-15 济南开发区星火科学技术研究院 一种汽油辛烷值改进剂及制备方法
US7981170B1 (en) 2000-04-21 2011-07-19 Shell Oil Company Gasoline-oxygenate blend and method of producing the same
CN104073304A (zh) * 2014-07-21 2014-10-01 方秀琴 一种具有防爆和节油功能的汽油添加剂

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2365009A (en) * 1940-12-19 1944-12-12 Standard Oil Dev Co Motor fuels
US3030195A (en) * 1959-01-20 1962-04-17 Sun Oil Co Motor fuels
US3869262A (en) * 1971-05-05 1975-03-04 Oesterr Hiag Werke Ag Fuel and additive for the production thereof
US3950145A (en) * 1975-06-05 1976-04-13 Ethyl Corporation Fuel compositions and additive mixtures containing methanetricarboxylates for reducing exhaust gas catalyst plugging
US4028065A (en) * 1974-05-16 1977-06-07 Standard Oil Company Manganese containing fuels
US4052171A (en) * 1975-06-05 1977-10-04 Ethyl Corporation Fuel compositions and additive mixtures containing methanetricarboxylates for reducing exhaust gas catalyst plugging
US4067699A (en) * 1976-12-17 1978-01-10 Union Oil Company Of California Fuel composition
US4141693A (en) * 1974-12-18 1979-02-27 Standard Oil Company (Ohio) Manganese containing fuels
CA1073207A (fr) * 1975-11-14 1980-03-11 James M. Dejovine Combustible antidetonnant pour moteurs a combustion interne
US4376636A (en) * 1981-11-18 1983-03-15 Adriel Energy Corporation Fuel additive
US4390345A (en) * 1980-11-17 1983-06-28 Somorjai Gabor A Fuel compositions and additive mixtures for reducing hydrocarbon emissions
US4437436A (en) * 1982-10-04 1984-03-20 Shell Oil Company Antiknock additive compositions and unleaded gasoline containing same
EP0121089A2 (fr) * 1983-03-03 1984-10-10 DEA Mineraloel Aktiengesellschaft Combustible pour moteurs
DE3330165A1 (de) * 1983-08-20 1985-03-07 Union Rheinische Braunkohlen Kraftstoff AG, 5000 Köln Motor-kraftstoff

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2365009A (en) * 1940-12-19 1944-12-12 Standard Oil Dev Co Motor fuels
US3030195A (en) * 1959-01-20 1962-04-17 Sun Oil Co Motor fuels
US3869262A (en) * 1971-05-05 1975-03-04 Oesterr Hiag Werke Ag Fuel and additive for the production thereof
US4028065A (en) * 1974-05-16 1977-06-07 Standard Oil Company Manganese containing fuels
US4141693A (en) * 1974-12-18 1979-02-27 Standard Oil Company (Ohio) Manganese containing fuels
US3950145A (en) * 1975-06-05 1976-04-13 Ethyl Corporation Fuel compositions and additive mixtures containing methanetricarboxylates for reducing exhaust gas catalyst plugging
US4052171A (en) * 1975-06-05 1977-10-04 Ethyl Corporation Fuel compositions and additive mixtures containing methanetricarboxylates for reducing exhaust gas catalyst plugging
CA1073207A (fr) * 1975-11-14 1980-03-11 James M. Dejovine Combustible antidetonnant pour moteurs a combustion interne
US4067699A (en) * 1976-12-17 1978-01-10 Union Oil Company Of California Fuel composition
US4390345A (en) * 1980-11-17 1983-06-28 Somorjai Gabor A Fuel compositions and additive mixtures for reducing hydrocarbon emissions
US4376636A (en) * 1981-11-18 1983-03-15 Adriel Energy Corporation Fuel additive
US4437436A (en) * 1982-10-04 1984-03-20 Shell Oil Company Antiknock additive compositions and unleaded gasoline containing same
EP0121089A2 (fr) * 1983-03-03 1984-10-10 DEA Mineraloel Aktiengesellschaft Combustible pour moteurs
DE3330165A1 (de) * 1983-08-20 1985-03-07 Union Rheinische Braunkohlen Kraftstoff AG, 5000 Köln Motor-kraftstoff

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0435631A1 (fr) * 1989-12-22 1991-07-03 Ethyl Petroleum Additives Limited Compositions de combustible diesel
US5575823A (en) * 1989-12-22 1996-11-19 Ethyl Petroleum Additives Limited Diesel fuel compositions
US5944858A (en) * 1990-09-20 1999-08-31 Ethyl Petroleum Additives, Ltd. Hydrocarbonaceous fuel compositions and additives therefor
EP0667387A3 (fr) * 1994-02-10 1995-09-27 Ethyl Corp
US5511517A (en) * 1994-02-10 1996-04-30 Ethyl Corporation Reducing exhaust emissions from otto-cycle engines
AU688433B2 (en) * 1994-02-10 1998-03-12 Ethyl Corporation Reducing exhaust emissions from otto-cycle engines
US7981170B1 (en) 2000-04-21 2011-07-19 Shell Oil Company Gasoline-oxygenate blend and method of producing the same
KR100351794B1 (ko) * 2001-06-01 2002-09-05 주식회사 서현케미칼 옥탄가를 증대시키는 연료 첨가제
CN102093918A (zh) * 2009-12-11 2011-06-15 济南开发区星火科学技术研究院 一种汽油辛烷值改进剂及制备方法
CN101886004A (zh) * 2010-07-12 2010-11-17 山东亿源石化有限公司 一种甲醇汽油添加剂及其配制的甲醇汽油以及它们的生产方法
CN104073304A (zh) * 2014-07-21 2014-10-01 方秀琴 一种具有防爆和节油功能的汽油添加剂

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Publication number Publication date
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