WO2006052985A1 - Lactones en tant que nouveaux additifs de carburant oxygénés, carburants basés sur lesdites lactones et méthodes d’emploi desdits carburants - Google Patents

Lactones en tant que nouveaux additifs de carburant oxygénés, carburants basés sur lesdites lactones et méthodes d’emploi desdits carburants Download PDF

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Publication number
WO2006052985A1
WO2006052985A1 PCT/US2005/040465 US2005040465W WO2006052985A1 WO 2006052985 A1 WO2006052985 A1 WO 2006052985A1 US 2005040465 W US2005040465 W US 2005040465W WO 2006052985 A1 WO2006052985 A1 WO 2006052985A1
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WIPO (PCT)
Prior art keywords
lactone
acid
butyrolactone
hydroxy
group
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PCT/US2005/040465
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English (en)
Inventor
J. Michael Robinson
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The Board Of Regents Of The University Of Texas System
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Publication of WO2006052985A1 publication Critical patent/WO2006052985A1/fr

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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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/023—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for spark ignition
    • 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, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • 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
    • C10L1/1855—Cyclic ethers, e.g. epoxides, lactides, lactones

Definitions

  • the present invention relates to new oxygenate additives for fuels, to fuels including the new fuel additives and to method for making and using same.
  • the present invention relates to new oxygenate additives for fuels, where the additives include cyclic esters having between four and 20 carbon atoms, to fuels including the new fuel additives and to method for making and using same, where the new oxygenate additives improve combustion efficiency and/or reduce emissions.
  • the present invention provides a fuel additive including one or a plurality of lactones of the general formula (I):
  • R 1 , R 2 , each R 3 , each R 4 , R 5 , and R 6 are the same or different and are selected from the group consisting of a hydrogen atom, an alkyl group having between 1 and about 20 carbon atoms, an aryl group having between about 6 and about 20 carbons atoms, an araalkyl group having between about 7 and about 20 carbons atoms, an alkaaryl group having between about 7 and about 20 carbons atoms, hetero analogs where one or more of the carbon atoms are substituted for oxygen, and n is an integer having a value between 0 and 4 and mixtures or combinations thereof, and where the fuel additive improves combustion efficiency and/or reduces emissions.
  • the present invention provides a preferred class of new oxygenated fuel additives, where the preferred class includes one or a plurality of four membered lactones of the formula (H):
  • R 7 , R 8 , R 9 , and R 10 are the same or different and are selected from the group consisting of a hydrogen atom, an alkyl group having between 1 and about 20 carbon atoms, an aryl group having between about 6 and about 20 carbons atoms, an araalkyl group having between about 7 and about 20 carbons atoms, an alkaaryl group having between about 7 and about 20 carbons atoms, hetero analogs where one or more of the carbon atoms are substituted for oxygen, and mixtures or combinations thereof, and where the fuel additive improves combustion efficiency and/or reduces emissions.
  • the present invention also provides another preferred class of new oxygenated fuel additives, where the additives including one or a plurality of five-membered lactones of the formula (DI):
  • R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 are the same or different and are selected from the group consisting of a hydrogen atom, an alkyl group having between 1 and about 20 carbon atoms, an aryl group having between about 6 and about 20 carbons atoms, an araalkyl group having between about 7 and about 20 carbons atoms, an alkaaryl group having between about 7 and about 20 carbons atoms, hetero analogs where one or more of the carbon atoms are substituted for oxygen, and mixtures or combinations thereof, and where the fuel additive improves combustion efficiency and/or reduces emissions.
  • the present invention provides another preferred class of new oxygenated fuel additives, where the additives include one or a plurality of six-membered lactones of the formula (IV):.
  • R 21 R 22 R19R20 where R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , and R 24 axe the same or different and are selected from the group consisting of a hydrogen atom, an alkyl group having between 1 and about 20 carbon atoms, an aryl group having between about 6 and about 20 carbons atoms, an araalkyl group having between about 7 and about 20 carbons atoms, an alkaaryl group having between about 7 and about 20 carbons atoms, hetero analogs where one or more of the carbon atoms are substituted for oxygen, and mixtures or combinations thereof, and where the fuel additive improves combustion efficiency and/or reduces emissions.
  • the present invention provides another preferred class of new oxygenated fuel additives, where the additives include one or a plurality of seven-membered lactones of the formula (V):
  • R 25 , R 26 , R 27 , R 28 ,R 29 ,R 30 ,R 31 , R 32 , R 33 , and R 34 are the same or different and are selected from the group consisting of a hydrogen atom, an alkyl group having between 1 and about 20 carbon atoms, an aryl group having between about 6 and about 20 carbons atoms, an araalkyl group having between about 7 and about 20 carbons atoms, an alkaaryl group having between about 7 and about 20 carbons atoms, hetero analogs where one or more of the carbon atoms are substituted for oxygen, and mixtures or combinations thereof, and where the fuel additive improves combustion efficiency and/or reduces emissions.
  • the present invention provides another preferred class of new oxygenated fuel additives, where the additives include one or a plurality of eight-membered lactones of the formula (VI): R 45 R 46 C CR 35 R 36
  • R 35 , R 36 , R 37 , R 38 , R 39 , R 40 , R 41 , R 42 , R 43 , R 44 , R 45 , and R 46 are the same or different and are selected from the group consisting of a hydrogen atom, an alkyl group having between 1 and about 20 carbon atoms, an aryl group having between about 6 and about 20 carbons atoms, an araalkyl group having between about 7 and about 20 carbons atoms, an alkaaryl group having between about 7 and about 20 carbons atoms, hetero analogs where one or more of the carbon atoms are substituted for oxygen, and mixtures or combinations thereof, and where the fuel additive improves combustion efficiency and/or reduces emissions.
  • the present invention also provides a fuel including a fuel additive having at least one lactone of the general formula (T):
  • R 1 , R 2 , each R 3 , each R 5 , and R 6 are the same or different and are selected from the group consisting of a hydrogen atom, an alkyl group having between 1 and about 20 carbon atoms, an aryl group having between about 6 and about 20 carbons atoms, an araalkyl group having between about 7 and about 20 carbons atoms, an alkaaryl group having between about 7 and about 20 carbons atoms, hetero analogs where one or more of the carbon atoms are substituted for oxygen, and n is an integer having a value between 0 and 4 and mixtures or combinations thereof, and where the fuel additive improves combustion efficiency and/or reduces emissions.
  • the present invention also provides a fuel additive having one or a plurality of lactones of the general formulas (E-VI) as previously described, where the fuel additive improves combustion efficiency and/or reduces emissions.
  • the present invention provides a method for reducing emissions and improving combustion efficiencies from the burning of fuels including the steps of: supplying a fuel including a fuel additive having at least one lactone of the general formula
  • R 1 , R 2 , each R 3 , each R 5 , and R 6 are the same or different and are selected from the group consisting of a hydrogen atom, an alkyl group having between 1 and about 20 carbon atoms, an aryl group having between about 6 and about 20 carbons atoms, an araalkyl group having between about 7 and about 20 carbons atoms, an alkaaryl group having between about 7 and about 20 carbons atoms, hetero analogs where one or more of the carbon atoms are substituted for oxygen, and n is an integer having a value between 0 and 4 and mixtures or combinations thereof and where the fuel additive improves combustion efficiency and/or reduces emissions.
  • the present invention provides a method for reducing emissions and improving combustion from the burning of fossil fuels including the steps of: supplying a fuel including a fuel additive including at least one lactone of the general formulas (H- VI) as described above to an internal combustion engine, a fossil fuel powered generator, or a fuel powered energy conversion unit, where the fuel additive improves combustion efficiency and/or reduces emissions, and other devices that convert chemical energy in a fuel to mechanical and/or electrical energy, and other energy conversion systems that convert chemical energy stored in a fuel to mechanical and/or electrical energy. burning the fuel in the engine, generator or unit to convert energy stored in the fuel to a useable form of energy.
  • lactones cyclic esters
  • AKI Anti Knock Index
  • the inventors have found that lactones are suitable for blending with gasoline fuels to enhance octane rating and in this manner and perhaps other means to also reduce pollutants when such blended fuels are utilized.
  • the lactones can also be used in other fuels such as diesel, jet fuel, heating oil, etc.
  • the present invention broadly relates to a fuel additive including a lactone of the general formula (I):
  • R 1 , R 2 , each R 3 , each R 4 , R 5 , and R 6 are the same or different and are selected from the group consisting of a hydrogen atom, an alkyl group having between 1 and about 20 carbon atoms, an aryl group having between about 6 and about 20 carbons atoms, an araalkyl group having between about 7 and about 20 carbons atoms, an alkaaryl group having between about 7 and about 20 carbons atoms, hetero analogs where one or more of the carbon atoms are substituted for oxygen, and n is an integer having a value between 0 and 4 and mixtures or combinations thereof and to fuels including the fuel additives and where the fuel additive improves combustion efficiency and/or reduces emissions.
  • the present invention also broadly relates to a method for reducing emissions and improving combustion from the burning of fossil fuels including the steps of: supplying a fuel including a fuel additive having at least one lactone of the general formula
  • R 1 , R 2 , each R 3 , each R 5 , and R 6 are the same or different and are selected from the group consisting of a hydrogen atom, an alkyl group having between 1 and about 20 carbon atoms, an aryl group having between about 6 and about 20 carbons atoms, an araalkyl group having between about 7 and about 20 carbons atoms, an alkaaryl group having between about 7 and about 20 carbons atoms, hetero analogs where one or more of the carbon atoms are substituted for oxygen, and n is an integer having a value between 0 and 4 and mixtures or combinations thereof and where the fuel additive improves combustion efficiency and/or reduces emissions.
  • Preferred lactones or cyclic esters include, without limitation, lactones of formulas (E), (DI), (TV), (V) and (VI). Particularly preferred lactones include, without limitation, lactones of formula (IH) and (IV).
  • lactones suitable for use as a fuel additive of this invention include, without limitation, ⁇ -propiolactone or hydracrylic acid ⁇ -lactone or 3-hydroxypropionic acid lactone (C 3 H 4 O 2 ); ⁇ -crotonolactone or 2-buten-l,4-olide-25H-furanone (C 4 H 4 O 2 ); ⁇ - butyrolactone or 4-methyl-2-oxetanone or ⁇ -methyl- ⁇ -propiolactone or 3-hydroxybutyric acid ⁇ -lactone (C 4 H 6 O 2 ); ⁇ -butyrolactone or 4-hydroxbutyric acid lactone or ⁇ -hydroxybutyric acid lactone (C 4 H 6 O 2 ); ⁇ -hydroxy- ⁇ -butyrolactone (C 4 H 6 O 3 ); ⁇ -hydroxy- ⁇ -butyrolactone or 4,5- dihydro-3-hydroxy-23H-furanone (C 4 H 6 O 3 ); ⁇ -erythronic acid
  • the particularly preferred lactones are five and six membered ring cyclic esters (compounds of formulas (HI) and (TV)) such as gamma-valerolactone (referred to herein as “compound 1 "), gamma-caprolactone (referred to herein as “compound 2”), delta- valerolactone (referred to herein as “compound 3”), delta-caprolactone (referred to herein as “compound 4”) and mixtures or combinations thereof.
  • compound 1 gamma-valerolactone
  • compound 2 gamma-caprolactone
  • compound 3 delta- valerolactone
  • compound 4 delta-caprolactone
  • Suitable fuels for use in this invention include, without limitation, gasoline, diesel, aviation fuel, heating oil, kerosine, etc.
  • the present invention stands in stark contrast to results of Heisler and Eckert disclosed in United States Pat. No. 3,015,547. Heisler and Eckert found that when lactones were admixed with high octane gasoline containing tetraethyl lead, "the lactones appear to be ineffective in raising the octane rating of gasolines unless an organo-lead anti-knock agent, normally tetraethyl lead, is a component of the gasoline mixture.” And further, Heisler and Eckert found that these lactones have no effect on a gasoline containing only aliphatic hydrocarbons with no aromatics. The inventors findings are quite opposite.
  • lactones such as the particularly preferred lactones listed above have relatively high boiling points: compound 1 has a boiling point (bp) 200 0 C, while the bp of compound 2 is 219°C. Moreover, compounds 1 and 2 have a low vapor pressures and low flash points: compound 1 has a flash point 81 0 C and compound 2 has a flash point of 98°C, such compounds normally do not have such high octane numbers.
  • ethanol has a bp of 78°C and flash point of 16°C. It is thought that the low molecular weight of ethanol and its relatively high oxygen to carbon ratio, makes it ideal as an oxygenate fuel additive. It is believed that the additives of this invention have equivalent or improved additive properties as compared to ethanol due to their relatively low vapor pressure and low flash point.
  • Lactones of this invention where one of the R 1"46 groups is a group including a four to six carbon atoms straight chain alkyl group (CH 3 (CH 2 ) j -, where i is 3-18), and all other R groups being hydrogen are ideally suited for diesel additives or for making bio-diesel. These preferred lactones for diesel applications will have high cetane numbers due to the straight chained alkyl group.
  • methyl esters of long chain fatty acids are used for cetane enhancement in oxygenate fuel additives and as standalone fuel in so-called “biodiesel.”
  • the diesel lactone additives of this invention represent new and novel cetane enchancers for diesel fuels or for the production of bio-diesel.
  • the cyclic lactone oxygenated fuel additive of this invention provides an alternative to expensive ethanol as an octane enhancer and oxygenated additive for gasoline and aviation fuels. Some of these lactones have even higher octane numbers than ethanol and much lower Reid vapor pressure values that essentially precludes these compounds from themselves contributing to a vapor that pollutes the atmosphere.
  • the additives of this invention are ideally suited for use in warm climes and seasons where the amount of blended ethanol is limited and for use in high altitude environments where similar constraints are required.
  • the lactone fuel additives of this invention can be synthesized form many resources including carbohydrates from biomass.
  • the lactone fuel additives of this invention are naturally occurring compounds, although they can be synthetically prepared.
  • the lactone fuel additives of this invention are also bio-degradable because the cyclic ester (lactone) is a naturally occurring and biologically labile functional group.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
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Abstract

La présente invention décrit un nouvel additif pour carburant oxygéné, qui est un ester cyclique ou une lactone. La présente invention décrit également un carburant incluant ledit nouvel additif pour carburant oxygéné. La présente invention décrit en outre une méthode permettant d’augmenter l’efficacité de moteurs ou d’autres dispositifs de combustion brûlant un carburant qui inclut ledit nouvel additif pour carburant oxygéné.
PCT/US2005/040465 2004-11-08 2005-11-08 Lactones en tant que nouveaux additifs de carburant oxygénés, carburants basés sur lesdites lactones et méthodes d’emploi desdits carburants WO2006052985A1 (fr)

Applications Claiming Priority (2)

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US10/984,024 2004-11-08
US10/984,024 US20060096158A1 (en) 2004-11-08 2004-11-08 Lactones as new oxygenate fuel additives, fuels based thereon and methods for using same

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WO2006052985A1 true WO2006052985A1 (fr) 2006-05-18

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WO2009143327A1 (fr) 2008-05-21 2009-11-26 Enersol, Inc.., N.A. L.P. Odorisation de l'hydrogène
BRPI0803522A2 (pt) * 2008-09-17 2010-06-15 Petroleo Brasileiro Sa composições de combustìvel do ciclo diesel contendo dianidrohexitóis e derivados
EP2988597B1 (fr) * 2013-04-04 2022-06-08 President and Fellows of Harvard College Macrolides et leurs procédés de préparation et d'utilisation
JP2017531663A (ja) 2014-10-08 2017-10-26 プレジデント アンド フェローズ オブ ハーバード カレッジ １４員ケトライドならびにそれらの調製および使用の方法
EP3273969A4 (fr) 2015-03-25 2018-11-21 President and Fellows of Harvard College Macrolides à sucres modifiés de type désosamine et utilisations de ceux-ci
JP2019010962A (ja) * 2017-06-30 2019-01-24 マツダ株式会社 車両用前照灯及び車両用前照灯の配光制御装置

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EP0661376A1 (fr) * 1993-12-23 1995-07-05 Veba Oel Ag Combustibles pour OTTO-moteurs
EP0905217A1 (fr) * 1997-09-30 1999-03-31 Nippon Oil Co. Ltd. Essence sans plomb pour moteur à essence à injection directe

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