Nitrogen Or Oxygen Bonded Directly To The Carbon Of The -c(=o)o- Group (e.g., Carbamic And Carbonic Compounds, Etc.) Patents (Class 44/387)
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Patent number: 5651799Abstract: Polylactone aminocarbamates having the formula: ##STR1## wherein R.sub.1 is a hydrocarbyl group having a sufficient number of carbon atoms to render the compound soluble in hydrocarbons boiling in the gasoline or diesel fuel range;R.sub.2 is an alkylene group of about 2 to 5 carbon atoms;A is a polyamine moiety having at least one basic nitrogen atom;and x is an integer from 1 to 25.The polylactone aminocarbamates of formula I are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: June 20, 1996Date of Patent: July 29, 1997Assignee: Chevron Chemical CompanyInventor: Richard E. Cherpeck
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Patent number: 5637120Abstract: Polyoxyalkylene polylactone aminocarbamates having the formula: ##STR1## wherein R.sub.1 is a hydrocarbyl group having a sufficient number of carbon atoms to render the compound soluble in hydrocarbons boiling in the gasoline or diesel fuel range;R.sub.2 and R.sub.3 are each independently hydrogen or lower alkyl having about 1 to about 6 carbon atoms and each R.sub.2 and R.sub.3 is independently selected in each --O--CHR.sub.2 --CHR.sub.3 -- unit;R.sub.4 is an alkylene group of about 2 to about 5 carbon atoms;A is a polyamine moiety having at least one basic nitrogen atom;x is an integer from about 1 to about 100; andy is an integer from about 1 to about 25.The polyoxyalkylene polylactone aminocarbamates of formula I are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: June 20, 1996Date of Patent: June 10, 1997Assignee: Chevron Chemical CompanyInventor: Richard E. Cherpeck
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Patent number: 5618319Abstract: Alkylamine polylactone aminocarbamates having the formula: ##STR1## wherein R.sub.1 is a hydrocarbyl group having a sufficient number of carbon atoms to render the compound soluble in hydrocarbons boiling in the gasoline or diesel fuel range;R.sub.2 is an alkylene group of about 2 to about 5 carbon atoms;A is a polyamine moiety having at least one basic nitrogen atom;and x is an integer from about 1 to about 25.The alkylamine polylactone aminocarbamates of formula I are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: June 20, 1996Date of Patent: April 8, 1997Assignee: Chevron Chemical CompanyInventor: Richard E. Cherpeck
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Patent number: 5514190Abstract: A highly effective fuel additive composition for control of intake valve deposits is described. It comprises (a) a gasoline-soluble Mannich reaction product of (i) a high molecular weight alkyl-substituted phenol, (ii) amine, and (iii) aldehyde; (b) a gasoline-soluble poly(oxyalkylene) carbamate; and (c) a gasoline-soluble poly(oxyalkylene) alcohol, glycol or polyol, or mono or diether thereof. Fuel compositions and methods of controlling engine deposits are also described.Type: GrantFiled: December 8, 1994Date of Patent: May 7, 1996Assignee: Ethyl CorporationInventors: Lawrence J. Cunningham, Thomas L. Zahalka
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Patent number: 5509943Abstract: The present invention provides a novel class of compounds, useful as gasoline detergent additives, comprising hydrocarbyloxypolyether allophonate esters of 2-hydroxy ethane. The present invention also provides a motor fuel composition containing the novel allophonate esters and further provides a method of synthesizing the allophonate esters of the present invention.Type: GrantFiled: January 11, 1995Date of Patent: April 23, 1996Assignee: Texaco Inc.Inventors: Sheldon Herbstman, Constance A. Cadorette
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Patent number: 5503644Abstract: Intake valve deposits in port fuel injected engines are reduced by using a fuel containing a mixture of (a) an oil soluble polyamine selected from (i) an aliphatic alkylene polyamine containing at least one olefinic polymer chain attached to a nitrogen and/or carbon atom of the alkylene radical(s) connecting the amino nitrogen atoms and said polyamine having a number average molecular weight in the range of from about 600 to about 10,000, (ii) a Mannich polyamine comprising the condensation product of a high molecular weight sulfur-free alkyl-substituted hydroxyaromatic compound wherein the alkyl group has a number average molecular weight from about 600 to about 10,000, an amine which contains an amino group having at least one active hydrogen atom, and an aldehyde, wherein the respective molar ratio of reactants is 1:0.1-10:0.Type: GrantFiled: April 26, 1994Date of Patent: April 2, 1996Assignee: Shell Oil CompanyInventors: Leonard B. Graiff, Robert P. Aiello, H. Dale Millay, Michael J. Riley, Kevin W. Poindexter
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Patent number: 5484463Abstract: Poly(oxyalkylene) hydroxy and amino aromatic carbamates having the formula: ##STR1## or a fuel-soluble salt thereof; wherein X is hydroxy or amino;R is hydrogen or lower alkyl having 1 to 6 carbon atoms;R.sub.1 and R.sub.2 are each independently hydrogen, hydroxy, lower alkyl having 1 to 6 carbon atoms, lower alkoxy having 1 to 6 carbon atoms, nitro, amino, N-alkylamino wherein the alkyl group contains 1 to 6 carbon atoms, or N,N-dialkylamino wherein each alkyl group independently contains 1 to 6 carbon atoms;R.sub.3 and R.sub.4 are each independently hydrogen or lower alkyl having 1 to 6 carbon atoms;R.sub.5 is hydrogen, alkyl having 1 to 30 carbon atoms, phenyl, aralkyl or alkaryl having 7 to 36 carbon atoms, or an acyl group having the formula: ##STR2## wherein R.sub.6 is alkyl having 1 to 30 carbon atoms, phenyl, or aralkyl or alkaryl having 7 to 36 carbon atoms;and n is an integer from 5 to 100.Type: GrantFiled: May 2, 1994Date of Patent: January 16, 1996Assignee: Chevron Chemical CompanyInventor: Richard E. Cherpeck
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Patent number: 5445749Abstract: Hybrid engines containing a metal-ceramic interface can be lubricated with composition comprising a carrier fluid and a molybdenum thiocarbamate. Friction and wear are low even when detergent and dispersant additives are present in the lubricant.Type: GrantFiled: August 23, 1994Date of Patent: August 29, 1995Assignee: The Lubrizol CorporationInventor: Hyun-Soo Hong
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Patent number: 5413615Abstract: Polyalkyl hydroxy and amino aromatic carbamates having the formula: ##STR1## or a fuel-soluble salt thereof; wherein X is hydroxy or amino;R.sub.1 and R.sub.2 are independently hydrogen, hydroxy, lower alkyl having 1 to 6 carbon atoms, lower alkoxy having 1 to 6 carbon atoms, nitro, amino, N-alkylamino wherein the alkyl group contains 1 to 6 carbon atoms, or N,N-dialkylamino wherein each alkyl group independently contains 1 to 6 carbon atoms;R.sub.3 is hydrogen or lower alkyl having 1 to 6 carbon atoms; andR.sub.4 is a polyalkyl group having an average molecular weight in the range of about 400 to 5,000.The polyalkyl hydroxy and amino aromatic carbamates of formula I are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: May 2, 1994Date of Patent: May 9, 1995Assignee: Chevron Chemical CompanyInventor: Richard E. Cherpeck
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Patent number: 5413614Abstract: Mannich condensation products prepared by the condensation of a compound of the formula: ##STR1## wherein R is hydrogen or lower alkyl having 1 to 6 carbon atoms; R.sub.1 is hydrogen, hydroxy, lower alkyl or lower alkoxy; R.sub.3 and R.sub.4 are independently hydrogen or lower alkyl; R.sub.5 is hydrogen, alkyl, phenyl, aralkyl, alkaryl, or an acyl group of the formula: ##STR2## wherein R.sub.6 is alkyl, phenyl, aralkyl or alkaryl; and n is an integer from 5 to 100;with an aldehyde and a nitrogen base selected from ammonia, lower alkylamine, a polyamine and mixtures thereof.The Mannich condensation products and their fuel soluble salts are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: May 2, 1994Date of Patent: May 9, 1995Assignee: Chevron Chemical CompanyInventor: Richard E. Cherpeck
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Patent number: 5366517Abstract: A fuel additive composition comprising:(a) a poly(oxyalkylene) hydroxyaromatic ether having the formula: ##STR1## or a fuel-soluble salt thereof; where R.sub.1 and R.sub.2 are each independently hydrogen, hydroxy, lower alkyl having 1 to 6 carbon atoms, or lower alkoxy having 1 to 6 carbon atoms; R.sub.3 and R.sub.4 are each independently hydrogen or lower alkyl having 1 to 6 carbon atoms; R.sub.5 is hydrogen, alkyl having 1 to 30 carbon atoms, phenyl, aralkyl or alkaryl having 7 to 36 carbon atoms, or an acyl group of the formula: ##STR2## where R.sub.6 is alkyl having 1 to 30 carbon atoms, phenyl, or aralkyl or alkaryl having 7 to 36 carbon atoms; n is an integer from 5 to 100; and x is an integer from 0 to 10; and(b) a poly(oxyalkylene) amine having at least one basic nitrogen atom and a sufficient number of oxyalkylene units to render the poly(oxyalkylene) amine soluble in hydrocarbons boiling in the gasoline or diesel fuel range.Type: GrantFiled: December 18, 1992Date of Patent: November 22, 1994Assignee: Chevron Research and Technology CompanyInventor: Richard E. Cherpeck
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Patent number: 5348560Abstract: Carbamates having a long-chain N-alkyl radical, a process for the preparation of the carbamates in a conventional manner and fuels and lubricants which contain these carbamates as additives.Type: GrantFiled: November 13, 1992Date of Patent: September 20, 1994Assignee: BASF AktiengesellschaftInventors: Juergen Mohr, Knut Oppenlaender, Wolf-Dieter Balzer, Juergen Thomas, Peter Schreyer
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Patent number: 5322529Abstract: Disclosed are liquid alkylphenyl poly(oxypropylene) aminocarbamates which do not form a wax when cooled to -40.degree. C. in a 50 weight percent solution with toluene, said aminocarbamates having at least one basic nitrogen and an average molecular weight of about 600 to 6,000 and wherein the alkyl group is substantially straight-chain of from 25 to 50 carbon atoms. Also disclosed are fuel compositions and concentrates as well as lubricating oil compositions and concentrates containing said alkylphenyl poly(oxypropylene) aminocarbamates.Type: GrantFiled: September 12, 1990Date of Patent: June 21, 1994Assignee: Chevron Research and Technology CompanyInventor: Thomas F. Buckley, III
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Patent number: 5312460Abstract: Disclosed is a fuel composition comprising a hydrocarbon boiling in the gasoline or diesel range and from about 30 to about 5,000 parts per million of an alkylphenyl poly(oxypropylene) aminocarbamate having at least one basic nitrogen and an average molecular weight of about 600 to 6,000 and wherein the alkyl group is substantially straight-chain of at least 15 carbon atoms. The instant invention is based on the discovery that use of the unique hydrocarbyl group, i.e., an alkylphenyl group wherein the alkyl group is derived from a substantially straight-chain alkyl group of at least 15 carbon atoms imparts to the alkylphenyl poly(oxypropylene) aminocarbamate not only lubricating oil compatibility but also an unexpected decrease in crankcase deposits.Type: GrantFiled: November 17, 1992Date of Patent: May 17, 1994Assignee: Chevron Research CompanyInventor: Thomas F. Buckley, III
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Patent number: 5306314Abstract: Poly(alkylene ether) aminocarbamates having the formula: ##STR1## wherein A is a polyamine moiety having at least one basic nitrogen atom; R.sub.1 is a hydrocarbyl group having a sufficient number of carbon atoms to render the poly(vinyl ether) aminocarbamate soluble in hydrocarbons boiling in the gasoline or diesel fuel range; R.sub.2 is an alkylene group having 2 to about 8 carbon atoms; R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are each independently hydrogen or a lower alkyl group having 1 to about 4 carbon atoms; R.sub.9 is an alkyl group having 1 to about 10 carbon atoms; m is 0 or 1; and n is an integer from 5 to 99.The poly(vinyl ether) aminocarbamates of formula I are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: April 1, 1993Date of Patent: April 26, 1994Assignee: Chevron Research and Technology CompanyInventor: Richard E. Cherpeck
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Patent number: 5286265Abstract: The invention relates to an internal combustion fuel concentrate comprising: (a) from 1 to 95% of a chlorine-free carbamate prepared by reacting a carbamate of formula ##STR1## with a compound of the formula R OH (VI) in the presence of either a strone organic base or a tetra hydrocarbyl titanate so as to exchange the group R in formula (I) with a group R.sup.1 in formula (II), and (b) a fuel compatible solvent therefor. In the formula (I) R is a hydrocarbyl or substituted hydrocarbyl group and R.sup.1 is a hydrocarbyl or a hetero-substituted hydrocarbyl group different from R. In formula (I), X and Y are independently any of hydrogen, a hydrocarbyl group, or the group of the formula ##STR2## where Z is either a divalent hydrocarbyl, a substituted hydrocarbyl group or the group of formula(alkylene).sub.m (NH.sub.n (alkylene).sub.Type: GrantFiled: April 14, 1992Date of Patent: February 15, 1994Assignee: BP Chemicals LimitedInventors: Richard A'Court, William J. Fox, John E. Hamlin, Sean P. O'Connor
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Patent number: 5271748Abstract: Additives which improve the low-temperature properties of distillate fuels are the polymeric and/or oligomeric monomers selected from ester/urethane reaction products of a combination of anhydrides and epoxides (or their corresponding acid/diol equivalents), and a urethane precursor and optionally with various suitable reactive materials to provide optional termonomers.Type: GrantFiled: September 17, 1992Date of Patent: December 21, 1993Assignee: Mobil Oil CorporationInventors: David J. Baillargeon, Angeline B. Cardis, Dale B. Heck, Susan W. Johnson
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Patent number: 5248315Abstract: Detergent additive for liquid fuels, obtained by means of the trans-esterification of a tertiary amine bearing at least two hydroxy functions, with a dialkyl carbonate and a higher aliphatic alcohol, and process for preparing said detergent additive.Type: GrantFiled: February 26, 1993Date of Patent: September 28, 1993Assignee: Euron S.p.A.Inventors: Emilio Gatti, Paolo Koch, Antonio Tontodonati
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Patent number: 5234477Abstract: The present invention is an unleaded fuel composition containing a major amount of a hydrocarbon base fuel of the gasoline boiling range containing an amount effective to reduce NO.sub.x emissions from electronic port fuel injected engines of ammonia or an ammonium compound. The invention also includes a method of reducing NO.sub.x emissions from electronic port fuel injected engines by feeding to the engine exhaust gases at a point between the outlet valves and catalytic converter an amount effective to reduce NO.sub.x emissions from the engines of ammonia or an ammonium compound.Type: GrantFiled: April 28, 1992Date of Patent: August 10, 1993Assignee: Shell Oil CompanyInventor: John E. Gwyn
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Patent number: 5192335Abstract: A fuel additive composition comprising:(a) a poly(oxyalkylene) amine having at least one basic nitrogen atom and a sufficient number of oxyalkylene units to render the poly(oxyalkylene) amine soluble in hydrocarbons boiling in the gasoline or diesel range; and(b) a polyalkyl hydroxyaromatic compound or salt thereof wherein the polyalkyl group has sufficient molecular weight and carbon chain length to render the polyalkyl hydroxyaromatic compound soluble in hydrocarbons boiling in the gasoline or diesel range.Type: GrantFiled: March 20, 1992Date of Patent: March 9, 1993Assignee: Chevron Research and Technology CompanyInventor: Richard E. Cherpeck
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Patent number: 5167670Abstract: The present invention is directed to novel poly(olefin)-polyamine-N-substituted polycarbamates, useful for preventing or reducing deposits in engines having the formula I ##STR1## wherein "n" is 2-8; R.sup.1 is a poly(olefin) chain having an average molecular weight of from about 500 to about 9900; R.sup.2 is an alkylene group containing 2 to 8 carbon atoms; R.sup.3 is independently a hydrogen atom, an alkyl group containing from 1 to 7 carbon atoms or --COOR.sup.5 with at least two of R.sup.4 being --COOR.sup.5 and wherein R.sup.5 is a hydrocarbyl or substituted hydrocarbyl group containing up to 20 carbon atoms.Type: GrantFiled: September 20, 1991Date of Patent: December 1, 1992Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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Patent number: 5126477Abstract: A process for the production of a carbamate suitable for use as a detergent additive to internal combustion engine fuels which process comprises reacting either ammonia, a primary amime or a secondary amine with a dihydrocarbyl carbonate in the presence as catalyst of a strong organic base and in the proportions necessary to produce either a mono-carbamate or a bis-carbamate.Type: GrantFiled: July 29, 1991Date of Patent: June 30, 1992Assignee: BP Chemicals LimitedInventors: Richard A'Court, William J. Fox, John E. Hamlin, Sean P. O'Connor
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Patent number: 5103041Abstract: A process for the production of a carbamate having formula (I), wherein X and Y are independently either hydrogen, a hydrocarbyl group or a hetero-substituted hydrocarbyl group or the group of formula (II), wherein Z is either a divalent hydrocarbyl, a substituted hydrocarbyl group or the group of formula (III) [(alkylene)m(NH)n(alkylene)m] in which n=0 to 4 and m=1 to 4, and R is a hydrocarbyl or substituted hydrocarbyl group, provided that if either one of X or Y is the group of formula (II), the other of X or Y is hydrogen, which process comprises reacting a compound of formula (IV), wherein X and Y are independently either hydrogen, a hydrocarbyl group or a hetero-substituted hydrocarbyl group with a dihydrocarbyl carbonate having formula (V), wherein independently R is as defined above in the presence as catalyst of a strong organic base and in the proportions necessary to produce either a mono-carbamate or a bis-carbamate.Type: GrantFiled: January 31, 1989Date of Patent: April 7, 1992Assignee: BP Chemicals LimitedInventors: Richard A'Court, William J. Fox, John E. Hamlin, Sean P. O'Connor
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Patent number: 5057122Abstract: Reaction products in which polyethers are connected to hydroxyalkylated polyamines using diisocyanates have been found to be effective ashless dispersants and detergents for various lubricants and fuels.Type: GrantFiled: December 26, 1989Date of Patent: October 15, 1991Assignee: Mobil Oil Corp.Inventors: David A. Blain, Angeline B. Cardis
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Patent number: 5055607Abstract: Long-chain aliphatic hydrocarbyl polyamino additives which comprise a long-chain aliphatic hydrocarbyl moiety, a polyamino moiety and an oxy-carbonyl connecting group which joins the aliphatic hydrocarbyl moiety and the polyamino moiety are useful as dispersants in fuel compositions and in lubricating oil compositions.Type: GrantFiled: September 9, 1988Date of Patent: October 8, 1991Assignee: Chevron Research CompanyInventor: Thomas F. Buckley, III
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Patent number: 5024678Abstract: Process for the prevention of reduction of deposits in carburetors, injection devices or similar devices of engines, which are operated with alcohol fuels comprising 99.9 to 75 Vol.-% methanol, ethanol or a mixture thereof and at least one corrosion inhibitor characterized in that one or several polyol ethers are added to the alcohol fuels in a quantity of 15 ppm up to 1 weight-%, whereby the polyol ether(s) has (have) the general formula ##STR1## wherein R is H, linear or branched C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.20 -alkenyl, polyunsaturated C.sub.1 -C.sub.20 - alkyl, C.sub.1 -C.sub.20 - cycloalkyl, mono- or bicyclo-C.sub.6 -C.sub.14 -aryl, unsubstituted or substituted, R.sub.1 is H, C.sub.1 -C.sub.8 -alkyl, unsubstituted or substituted aryl, R.sub.2 is H, C.sub.1 -C.sub.8 -alkyl, unsubstituted or substituted aryl, and R.sub.3 is OR.sub.5, SR.sub.5, N(R.sub.5).sub.2, wherein R.sub.5 is H, linear or branched C.sub.1 -C.sub.20 -alkyl, C.sub.1 -C.sub.20 -cycloalkyl, mono- and bicyclo-C.sub.6 -C.sub.Type: GrantFiled: April 5, 1988Date of Patent: June 18, 1991Assignee: DEA Mineralol AktiengesellschaftInventors: Dagmar Mertens-Gottselig, Hartmut Hammer, Heinrich Muller, Manfred Wildersohn
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Patent number: 5009670Abstract: Fuels for gasoline engines contain small amounts of copolymers of alkyl (meth)-acrylates where the alkyl radical is of 8 to 40 carbon atoms and/or vinyl esters of carboxylic acids of 8 to 40 carbon atoms and monoethylenically unsaturated mono- and/or dicarboxylic acids of 3 to 12 carbon atoms and/or monoethylenically unsaturated compounds having sulfo and/or phosphonic acid groups, having a total molecular weight of from 500 to 20,000 g per mole, some or all of the carboxyl, sulfo and phosphonic acid groups of the copolymers having been reacted with an alkali or alkaline earth with formation of the alkali metla salts or alkaline earth metal salts and the remainder of the acid groups having been reacted with ammonia and/or amines of not more than 50 carbon atoms to give the corresponding amide groups and/or ammonium salts.Type: GrantFiled: May 16, 1989Date of Patent: April 23, 1991Assignee: BASF AktiengesellschaftInventors: Franz-Dieter Martischius, Hans-Henning Vogel, Norbert Greif, Knut Oppenlaender, Walter Denzinger, Heinrich Hartmann
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Patent number: 5004480Abstract: Diesel fuel compositions containing dimethyl carbonate reduce pollution levels resulting when said fuel is combusted in a diesel engine.Type: GrantFiled: May 31, 1988Date of Patent: April 2, 1991Assignee: Union Oil Company of CaliforniaInventor: Diane D. Kanne
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Patent number: H1071Abstract: Liquid hydrocarbon fuels such as diesel fuel and aviation jet fuel are stabilized by insertion of solid porous stabilizing foam into storage tanks. Fuel-insoluble particles resulting from degradation of the fuel which form during prolonged storage are absorbed by the foam. The absorbed particles are removed from the foam by contacting it with a polar solvent. The foam thus regenerated is re-used for continued stabilization of stored liquid hydrocarbon fuels. The polar solvent having fuel-insoluble particles dissolved therein is recovered by distillation for re-use.Type: GrantFiled: December 13, 1990Date of Patent: July 7, 1992Assignee: United States of AmericaInventors: Margaret A. Wechter, Dennis R. Hardy