EP0474342A1 - Additifs pour fuel, carbonates dialkyliques asymétriques - Google Patents

Additifs pour fuel, carbonates dialkyliques asymétriques Download PDF

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Publication number
EP0474342A1
EP0474342A1 EP91306278A EP91306278A EP0474342A1 EP 0474342 A1 EP0474342 A1 EP 0474342A1 EP 91306278 A EP91306278 A EP 91306278A EP 91306278 A EP91306278 A EP 91306278A EP 0474342 A1 EP0474342 A1 EP 0474342A1
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EP
European Patent Office
Prior art keywords
carbonate
methyl
composition
butyl
liquid fuel
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.)
Withdrawn
Application number
EP91306278A
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German (de)
English (en)
Inventor
Lawrence J. Karas
David C. Dehm
William J. Piel
John A. Sofranko
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.)
Lyondell Chemical Technology LP
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Arco Chemical Technology LP
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Filing date
Publication date
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Publication of EP0474342A1 publication Critical patent/EP0474342A1/fr
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    • 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
    • C10L10/10—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, 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
    • 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
    • C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
    • 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
    • C10L1/182—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
    • 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
    • C10L1/182—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, 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

Definitions

  • This invention pertains to improved hydrocarbon fuel compositions containing minor amounts of at least one unsymmetrical dialkyl carbonate.
  • the invention relates to blends of gasoline and tertiary alkyl substituted carbonates such as methyl t-butyl carbonate, ethyl t-butyl carbonate, methyl t-amyl carbonate, and ethyl t-amyl carbonate.
  • gasoline used in such engines must have a high octane number throughout its entire distillation range in order to eliminate fuel-wasting and potentially damaging engine knock at all engine speeds and loads. Because of this requirement, gasoline compositions are normally formulated to have a Research Octane Number (RON) greater than about 80 and more preferably greater than about 90. Premium grade fuels may have octane ratings that are even higher. Because of the difficulties and expense associated with refining crude oil to directly yield a high octane fuel, it has been common practice to incorporate an additive into the fuel to increase the octane rating.
  • RON Research Octane Number
  • lead compounds such as tetraethyl lead were widely used as octane rating improvers.
  • the environmental and health problems associated with the discharge of lead into the atmosphere from internal combustion engines have led to a gradual removal of such additives from gasoline.
  • octane rating improvers that have been proposed for use include ethers such as methyl t-butyl ether and methyl t-amyl ether and alcohols such as methanol, ethanol, and t-butyl alcohol. Although blending components of these types are currently being used in commercial practice, certain disadvantages are associated with their use.
  • alcohols such as methanol and ethanol have limited compatibility with gasoline.
  • they tend to absorb water as a result of their polar hydrophilic character. Phase separation is commonly observed in a gasoline-alcohol blend once even a small amount of water is absorbed. This can result in the accelerated corrosion of a fuel system as well as plugging of fuel filters by the corrosion products. Extraordinary precautions must therefore be taken to avoid water contamination of alcohol-containing fuels.
  • adding methanol or ethanol to gasoline increases its vapor pressure and distorts or flattens the front half of the gasoline's distillation curve. Hard starting and vapor lock in hot weather may result. The distorted distillation curve and higher heat of vaporization can also have a combined deleterious effect on cold weather warm-up.
  • methyl t-butyl ether has a high blending RON, it has a relatively low boiling point (55°C) and so its use as an octane improver has the disadvantage that the amount of butane that can be included in the fuel is reduced. This may tend to offset the octane enhancement effect of the ether since butane is a high-octane blending component in its own right.
  • the high volatility of methyl t-butyl ether also limits the maximum amount that can be blended into gasoline due to the driveability problems such as vapor lock which can result at high concentrations.
  • Another class of oxygenated organic compounds proposed for use as blending agents to increase the octane rating of gasoline are carbonates (i.e., diesters of carbonic acid).
  • Fuel compositions of this type are described, for example, in Jpn. Pat. No. 60-46473, European Pat. Appl. Nos. 98,691, 112,172, and 82,688, and U.S. Pat. Nos. 2,331,386, 3,001,941, 3,382,181, 4,302,215, 4,380,455, 4,600,408, 4,891,049 and 4,904,279.
  • Dimethyl carbonate and diethyl carbonate while having suitably high Blending Octane Values (BOV), do suffer from certain disadvantages which would tend to discourage their use as octane improvers in gasoline compositions.
  • these compounds are very susceptible to hydrolysis, particularly in the presence of acidic substances which can serve as catalysts.
  • hydrolysis of the carbonates would generate methanol or ethanol; as described previously, the presence of these materials in gasoline is known to result in phase separation, corrosion, and driveability problems.
  • dialkyl carbonates i.e., those containing alkyl groups of more than two carbon atoms, may be more resistant to hydrolysis than diethyl or dimethyl carbonate.
  • the octane enhancement value of dialkyl carbonates tends to decrease as the total number of carbon atoms in the molecule is increased.
  • EP 98,691 teaches that the average blending octane number of a fuel is lowered as the normal alkyl group of a symmetrical carbonate is varied from methyl to ethyl to n-propyl to n-butyl.
  • Di-n-butyl carbonate in fact, provides little or no enhancement of the octane value of a typical gasoline fuel composition.
  • the octane number of a liquid hydrocarbon fuel composition may be significantly increased by the addition of minor amounts (i.e., less than 50 weight percent) of an unsymmetrical dialkyl carbonate selected from the group consisting of methyl t-butyl carbonate, ethyl t-butyl carbonate, methyl t-amyl carbonate, and ethyl t-amyl carbonate.
  • an unsymmetrical dialkyl carbonate selected from the group consisting of methyl t-butyl carbonate, ethyl t-butyl carbonate, methyl t-amyl carbonate, and ethyl t-amyl carbonate.
  • unsymmetrical carbonate additives are highly compatible with the hydrocarbon fuel and are surprisingly resistant to hydrolysis. Exposure of the modified fuel composition to water thus does not result in an undesirable extraction of the carbonate octane enhancer into the water phase or gradual decomposition of the carbonate.
  • the carbonates of this invention unlike dimethyl carbonate and diethyl carbonate, are nearly completely insoluble in water ( ⁇ 0.5% at 70°C); fuel blends containing the unsymmetrical carbonates exhibit a reduced tendency to absorb water.
  • the unsymmetrical carbonates have a mild pleasant odor that would not be objectionable upon blending into gasoline.
  • a further advantage of this invention is that the addition of the unsymmetrical dialkyl carbonate to a gasoline fuel does not adversely affect the Reid vapor pressure of the fuel. That is, the Reid vapor pressure is desirably lowered when the unsymmetrical dialkyl carbonates of this invention are added to a gasoline fuel.
  • This is a distinct advantage since low cost, highly volatile fuel components such as butanes can then be blended into the fuel without exceeding the desired vapor pressure limit.
  • certain conventional octane enhancers having a high volatility such as methyl t-butyl ether may preclude the incorporation of large amounts of butanes.
  • the use of the unsymmetrical dialkyl carbonates of this invention in a fuel is additionally expected to provide a cleaner burning fuel composition as compared to a fuel that does not contain any oxygen-containing additives. That is, by analogy to known oxygenated fuel additives such as ethers, alcohols, and diethyl carbonate, the production of undesirable and harmful engine emissions such as carbon monoxide is expected to be significantly suppressed by the incorporation of an unsymmetrical dialkyl carbonate into a fuel.
  • oxygenated fuel additives such as ethers, alcohols, and diethyl carbonate
  • This invention provides an improved liquid fuel composition
  • a hydrocarbon liquid fuel base and a minor proportion of a carbonate having the general structure wherein R is methyl or ethyl and R′ is tertiary butyl or terti amyl.
  • Figure 1 graphically illustrates the results obtained in Examples 4-8 wherein the octane blending values of several different symmetrical and unsymmetrical carbonates were measur using an unleaded gasoline base fuel.
  • the horizontal axis of figure represents the molecular weight of the carbonate, while the vertical axis represents the blending octane value.
  • Base fuels to which the carbonate compounds of this invention may be added to improve the anti-knock properties include all of the volatile liquid fuels known to be suitable for spark ignition internal combustion engines.
  • the hydrocarbon liquid fuel base comprises gasoline, e.g., a hydrocarbon liquid having a boiling range from about 90°F to about 430°F.
  • the liquid fuel base may comprise straight chain or branched chain paraffins, cyclic paraffins, olefins, and substituted or unsubstituted aromatic hydrocarbons or mixtures thereof.
  • This fuel may be produced by any known method, including, for example, distillation or fractionation yielding straight-run product, thermal and catalytic cracking, alkylation, reforming, polymerization, isomerization, and dehydrocyclodimerization.
  • Straight-run naphtha, alkylate gasoline, polymer gasoline, natural gasoline, isomerized or hydrotreated stocks, catalytically cracked or thermally cracked hydrocarbons, catalytically reformed stocks and synthetic liquid hydrocarbon fuels derived from carbonaceous materials such as coal or oil shale are suitable for use in this invention.
  • liquid hydrocarbon fuels heavier than gasoline such as residual fuels, kerosene, jet fuels, heating oils, diesel fuels, light gas oils, heavy gas oils, light cycle gas oils, heavy cycle gas oils, vacuum gas oils, petroleum middle distillate fuels, and diesel fuels.
  • the carbonates useful in the compositions of this invention have the general structure wherein R is methyl or ethyl and R′ is tertiary butyl or tertiary amyl.
  • suitable carbonates include methyl t-butyl carbonate, ethyl t-butyl carbonate, methyl t-amyl carbonate, and ethyl t-amyl carbonate. Mixtures of these carbonates may be used if desired. All of these compounds are characterized in having one C1-C2 primary alkyl group and one C4-C5 tertiary alkyl group attached to a carbonate moiety and have boiling points at atmospheric pressure of from about 140°C to 190°C (284°F to 374°F).
  • the carbonates may be prepared by any of the methods known in the art.
  • a tertiary alkoxide prepared by reacting an alkali metal such as potassium with a tertiary alcohol such as t-butyl alcohol or t-amyl alcohol may be reacted with carbon dioxide and subsequently an alkyl halide such as methyl bromide or ethyl bromide to yield the unsymmetrical carbonate.
  • the carbonates may be produced by reacting a tertiary alkoxide with a haloester such as ethyl chloroformate or methyl chloroformate.
  • a haloester such as ethyl chloroformate or methyl chloroformate.
  • the amount of carbonate is preferably from about 1 to 15 weight percent. Lower amounts will not have a significant effect on the octane number of the fuel composition. Higher amounts will likely be uneconomical. Owing to the high solubility of the carbonates in hydrocarbon fuels, the fuel compositions may be readily prepared by simply blending or mixing the carbonate into the hydrocarbon liquid fuel base.
  • the liquid fuel compositions of this invention may contain, in addition to the unsymmetrical dialkyl carbonate, any of the additives normally employed in fuels such as anti-icing agents, detergents, demulsifiers, corrosion inhibitors, dyes, deposit modifiers, anti-oxidants, metal deactivators, and upper cylinder lubricants, as well as other anti-knock additives such as organometallic compounds (e.g., tetraethyl lead, tetramethyl lead, cyclopentadienyl tricarbonyl manganese), alcohols (e.g., methanol, ethanol, t-butyl alcohol, isopropyl alcohol), ethers (e.g., methyl t-butyl ether, methyl t-amyl ether), and other types of carbonates (e.g., symmetrical dialkyl carbonates such as dimethyl carbonate, diethyl carbonate, di-n-butyl carbonate, di-t-butyl carbonate, and
  • the liquid fuel composition contains no significant amount of any added octane-enhancer other than the unsymmetrical dialkyl carbonate.
  • Unleaded gasoline i.e., gasoline that is essentially free of organo-lead additives
  • leaded gasoline may also be employed if desired.
  • the liquid fuel composition comprises from about 80 to 98 weight percent gasoline and from about 2 to 20 weight percent of an additive mixture.
  • the additive mixture is comprised of from about 1 to 19 weight percent (based on the total weight of the liquid fuel composition) of at least one unsymmetrical dialkyl carbonate of the type described hereinabove and from about 1 to 19 weight percent (based on the total weight of the composition) of at least one additional oxygenated compound.
  • the unsymmetrical dialkyl carbonate is most preferably methyl t-butyl carbonate, although ethyl t-butyl carbonate, methyl t-amyl carbonate, ethyl t-amyl carbonate, or mixtures thereof can also be used.
  • the oxygenated compound is selected from the group consisting of alcohols, ethers, symmetrical dialkyl carbonates, and cyclic alkylene carbonates, but most preferably is methyl t-butyl ether.
  • the fuel composition contains from about 1 to 15 weight percent of a mixture of symmetrical and unsymmetrical carbonates corresponding to the following structural formulae: wherein R is the same in carbonates A and B and is methyl or ethyl and R′ is the same in A and C and is tertiary butyl or tertiary amyl,
  • the carbonate mixture may comprise methyl t-butyl carbonate, dimethyl carbonate, and di-t-butyl carbonate.
  • the unsymmetrical carbonate A is the predominate component of the carbonate mixture (i,e., at least about 34 mole percent).
  • alkyl carbonate may reduce the effectiveness of some conventional corrosion inhibitors that are used to control the tendency of fuel system components to rust or otherwise corrode when placed in contact with the fuel.
  • the addition of one or more corrosion inhibitors of the type typically used in conventional oxygenate-containing fuels will provide adequate protection against rusting.
  • An example of a suitable corrosion inhibitor is "DCI 11", available from E. I. du Pont de Nemours. Addition of this inhibitor at a 20 ppm level into a gasoline-based fuel containing indolene and methyl t-butyl carbonate yielded a composition having an NACE rust rating (ASTM D665) of A.
  • Toluene (100 parts by volume) was employed as the hydrocarbon liquid fuel base in a composition containing 10 parts by volume methyl t-butyl carbonate.
  • Two phases formed when 5 parts by volume water was added, indicating that the methyl t-butyl carbonate does not significantly increase the hydrophilicity of the fuel composition.
  • the two phase mixture was allowed to stand in a stoppered glass volumetric flask for three weeks at room temperature with occasional agitation. No hydrolysis of the methyl t-butyl carbonate was detectable by gas chromatographic analysis of the organic and aqueous phases. The aqueous phase did not extract any of the methyl t-butyl carbonate from the organic layer.
  • Fuel compositions were prepared by blending 10 volume percent of various organic carbonates into a sample of regular unleaded gasoline obtained from a commercial source.
  • the research and motor octane values of each composition were determined using modifications of ASTM methods D2699 and D2700 developed by the Pittsburgh Applied Research Corporation and its predecessor Gulf Oil. These modified test methods have been in use for over 40 years in the industry, have been tested and verified using National Exchange Group samples, and have been proven to be as reliable as the standard ASTM procedures.
  • a constant pressure micro method carburetor is installed on the fourth bowl of a four bowl carburetor CFR-octane test unit using a special holder attached to the sight glass. A glass micro-bowl holding the fuel sample to be tested is inserted into the holder.
  • the standard CFR horizontal metering jet is replaced with a modified micro-bowl jet (different jets are required for the RON and MON tests).
  • the modified jet is equipped with a "T" to drain fuel and is connected to the micro-bowl with tubing for fuel flow to the CFR cylinder. Constant pressure is maintained by the use of a rubber stopper, drilled to hold a piece of copper tubing, and an air vent valve inserted into the micro-bowl.
  • the procedure used to measure octane values is otherwise the same as that of the standard ASTM method
  • methyl t-butyl carbonate was found to have an octane blending value considerably higher than methyl n-butyl carbonate (105.5 vs. 96.2). This result was unexpected since methyl t-butyl carbonate and methyl n-butyl carbonate are isomers and differ only with respect to the structure of the butyl group. Additionally, the blending octane value of methyl t-butyl carbonate was significantly greater than that of dimethyl carbonate. This finding was particularly surprising in view of the general expectation from the prior art that octane value decreases as the molecular weight and number of carbons per molecule increase.
  • Reid Vapor Pressure values for the fuel compositions were also determined using ASTM method D4953; the experimental values are given in Table 1. The results demonstrate that the incorporation of 10 volume percent of methyl t-butyl carbonate into a standard gasoline fuel has the desirable effect of decreasing the vapor pressure of the fuel composition.

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Combustion & Propulsion (AREA)
  • Liquid Carbonaceous Fuels (AREA)
EP91306278A 1990-09-05 1991-07-11 Additifs pour fuel, carbonates dialkyliques asymétriques Withdrawn EP0474342A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US712779 1985-03-18
US57805390A 1990-09-05 1990-09-05
US578053 1990-09-05
US71277991A 1991-06-10 1991-06-10

Publications (1)

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EP0474342A1 true EP0474342A1 (fr) 1992-03-11

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EP91306278A Withdrawn EP0474342A1 (fr) 1990-09-05 1991-07-11 Additifs pour fuel, carbonates dialkyliques asymétriques

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EP (1) EP0474342A1 (fr)
JP (1) JPH04234491A (fr)
CA (1) CA2048706A1 (fr)
MX (1) MX9100887A (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994004636A1 (fr) * 1992-08-24 1994-03-03 Orr William C Composition de carburant sans plomb a base de mmt
EP0748364A1 (fr) * 1994-03-02 1996-12-18 ORR, William C. Compositions de carburant mmt sans plomb
EP1751816A2 (fr) * 2004-05-26 2007-02-14 Société BIC Appareil et procede de production in situ de combustible pour pile a combustible
FR2894976A1 (fr) * 2005-12-16 2007-06-22 Total France Sa Essence aviation sans plomb
WO2008135801A2 (fr) * 2007-05-08 2008-11-13 Brenes Mario Araya Composition de composant renforçateur de puissance du carburant ajustable
GB2475785A (en) * 2009-11-24 2011-06-01 Shell Int Research Fuel formulations
US7977447B2 (en) 2008-11-18 2011-07-12 Sabic Innovative Plastics Ip B.V. Method for making carbonates and esters
US8557001B2 (en) 2009-11-24 2013-10-15 Shell Oil Company Fuel formulations
US8663346B2 (en) 2009-11-24 2014-03-04 Shell Oil Company Fuel formulations
US8741126B2 (en) 2008-06-30 2014-06-03 Total Marketing Services Aviation gasoline for aircraft piston engines, preparation process thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005029715A (ja) * 2003-07-08 2005-02-03 National Institute Of Advanced Industrial & Technology バイオディーゼルフューエルの製造方法
MX365334B (es) * 2011-12-30 2019-05-30 Butamax Advanced Biofuels Llc Composiciones inhibidoras de la corrosion para gasolinas oxigenadas.

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0098691A2 (fr) * 1982-06-21 1984-01-18 Imperial Chemical Industries Plc Compositions combustibles
EP0112172A1 (fr) * 1982-12-15 1984-06-27 The British Petroleum Company p.l.c. Procédé de production de carbonates de dihydrocarbyle, leur utilisation comme additifs d'essence
US4600408A (en) * 1985-04-29 1986-07-15 Union Oil Company Of California Gasoline compositions containing carbonates
US4891049A (en) * 1985-12-20 1990-01-02 Union Oil Company Of California Hydrocarbon fuel composition containing carbonate additive

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0098691A2 (fr) * 1982-06-21 1984-01-18 Imperial Chemical Industries Plc Compositions combustibles
EP0112172A1 (fr) * 1982-12-15 1984-06-27 The British Petroleum Company p.l.c. Procédé de production de carbonates de dihydrocarbyle, leur utilisation comme additifs d'essence
US4600408A (en) * 1985-04-29 1986-07-15 Union Oil Company Of California Gasoline compositions containing carbonates
US4891049A (en) * 1985-12-20 1990-01-02 Union Oil Company Of California Hydrocarbon fuel composition containing carbonate additive

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 11, no. 43 (C-402)(2490) February 1987 & JP-A-61 207 496 ( TOYO SODA MFG CO LTD ) 13 September 1986 *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994004636A1 (fr) * 1992-08-24 1994-03-03 Orr William C Composition de carburant sans plomb a base de mmt
EP0748364A1 (fr) * 1994-03-02 1996-12-18 ORR, William C. Compositions de carburant mmt sans plomb
EP0748364A4 (fr) * 1994-03-02 1997-07-23 William C Orr Compositions de carburant mmt sans plomb
EP1751816A4 (fr) * 2004-05-26 2009-08-12 Bic Soc Appareil et procede de production in situ de combustible pour pile a combustible
EP1751816A2 (fr) * 2004-05-26 2007-02-14 Société BIC Appareil et procede de production in situ de combustible pour pile a combustible
FR2894976A1 (fr) * 2005-12-16 2007-06-22 Total France Sa Essence aviation sans plomb
WO2007074226A1 (fr) * 2005-12-16 2007-07-05 Total France Essence aviation sans plomb
WO2008135801A2 (fr) * 2007-05-08 2008-11-13 Brenes Mario Araya Composition de composant renforçateur de puissance du carburant ajustable
WO2008135801A3 (fr) * 2007-05-08 2009-02-26 Brenes Mario Araya Composition de composant renforçateur de puissance du carburant ajustable
US8741126B2 (en) 2008-06-30 2014-06-03 Total Marketing Services Aviation gasoline for aircraft piston engines, preparation process thereof
US7977447B2 (en) 2008-11-18 2011-07-12 Sabic Innovative Plastics Ip B.V. Method for making carbonates and esters
GB2475785A (en) * 2009-11-24 2011-06-01 Shell Int Research Fuel formulations
US8557001B2 (en) 2009-11-24 2013-10-15 Shell Oil Company Fuel formulations
GB2475785B (en) * 2009-11-24 2014-01-15 Shell Int Research Fuel formulations
US8663346B2 (en) 2009-11-24 2014-03-04 Shell Oil Company Fuel formulations

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CA2048706A1 (fr) 1992-03-06
MX9100887A (es) 1992-05-04
JPH04234491A (ja) 1992-08-24

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