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US4525174A Expired / Lapsed US ⏱️ 0.0 years remaining

Method and fuel composition for control of octane requirement increase

Assignee: Union Oil Company of California
•
Filing: 1983-12-27
•
Granted: 1985-06-25
•
Expires: 2003-12-27
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Abstract

Abstract The control of the octane requirement increase phenomenon in a spark ignition, internal combustion engine is achieved by continuously or intermittently introducing with the combustion charge a fuel composition containing (a) an oil-soluble iron compound, (b) a volatile carboxylic acid or ester, and (c) a nonvolatile polar compound capable of solubilizing carbonaceous engine deposits, wherein said nonvolatile polar compound is introduced either simultaneously with said oil-soluble iron compound and said volatile carboxylic acid or ester during the intermission. Preferably said nonvolatile polar compound comprises an oxidation resistant hydrocarbon moiety covalently connected to a polar moiety selected from the group consisting of primary and secondary amino, formamido and sulfo radicals.

Inventors

  • 👤 Michael C. Croudace

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 21:35
CPC Classifications
C; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/18; C10L1/188; C10L1/1881; C10L1/19; C10L1/30; C10L1/305; F; F02; F02B; F02B75/00; F02B75/02; F02B2075/022; F02B2075/027

Claims Analysis

Total Claims: 64
Claim 1
Independent Claim 82 words
A method for operating a spark ignition internal combustion engine which comprises continuously or intermittently introducing, with the combustion intake charge to said engine, a fuel composition containing an octane requirement increase-inhibiting amount of (a) an oil-soluble iron compound, (b) a volatile mono carboxylic acid or ester, and (c) a non-volatile polar compound capable of solubilizing carbonaceous engine deposits, wherein said non-volatile polar compound is introduced either simultaneously with said oil-soluble iron compound and said volatile carboxylic acid or during the intermission.
Claim 2
Independent Claim 82 words
A method for operating a spark ignition internal combustion engine which comprises continuously or intermittently introducing, with the combustion intake charge to said engine, a fuel composition containing an octane requirement increase-inhibiting amount of (a) an oil-soluble iron compound, (b) a volatile mono carboxylic acid or ester, and (c) a non-volatile polar compound capable of solubilizing carbonaceous engine deposits, wherein said non-volatile polar compound is introduced either simultaneously with said oil-soluble iron compound and said volatile carboxylic acid or during the intermission.
Claim 3
Dependent Claim 23 words
The method of claim 1 wherein said oil-soluble iron compound is selected from the group consisting of cyclopentadienyl iron and substituted derivatives thereof.
Claim 4
Dependent Claim 45 words
The method of claim 2 wherein said soluble iron compound is selected from the group consisting of cyclopentadienyl iron and C 1 and C 3 alkyl substituted derivatives thereof wherein one or both of the cyclopentadienyl rings are substituted with one to two alkyl groups.
Claim 5
Dependent Claim 13 words
The method of claim 1 wherein said oil-soluble iron compound is dicyclopentadienyl iron.
Claim 6
Dependent Claim 28 words
The method of claim 1 wherein said carboxylic acid or ester is selected from the group consisting of the esters of C 2 to C 10 monocarboxylic acids.
Claim 7
Dependent Claim 30 words
The method of claim 5 wherein said ester is the derivative of a C 2 to C 4 monocarboxylic acid and a C 4 to C 8 tertiary alkyl alcohol.
Claim 8
Dependent Claim 11 words
The method of claim 6 wherein said ester is t-butyl acetate.
Claim 9
Dependent Claim 19 words
The method of claim 1 wherein said oil-soluble iron compound is dicyclopentadienyl iron and said oxygen-containing compound is t-butylacetate.
Claim 10
Dependent Claim 36 words
The method of claim 1 wherein said oil-soluble iron compound is introduced into said engine at a concentration of from at least about 0.0001 to about 10 grams of iron per gallon of said fuel composition.
Claim 11
Dependent Claim 35 words
The method of claim 9 wherein said monocarboxylic acid or ester is introduced into said engine at a concentration of from at least about 0.001 to about 10 grams per gallon of said fuel composition.
Claim 12
Dependent Claim 54 words
The method of claim 8 wherein dicyclopentadienyl iron is introduced into said engine at a concentration of from at least about 0.001 to about 5 grams of iron and said t-butylacetate is introduced into said engine at a concentration of at least about 0.001 to about 10 grams per gallon of said fuel composition.
Claim 13
Dependent Claim 48 words
The method of claim 1 wherein said polar compound comprises a polar radical selected from the group consisting of acetoxy, amino, ammonium, carbamido, carbamyl, carbonyl, carboxy, carboxylate, cyano, formamido, formyl, hydrazino, hydroxamino, hydroxy, imino, mercapto, nitro, nitroso, phosphono, phosphonate, sulfamino, sulfamyl, sulfino, sulfinyl, sulfo, sulfonate and thiocyano radicals.
Claim 14
Dependent Claim 30 words
The method of claim 12 wherein said radical is covalently bound to a non-polar hydrocarbyl or polyoxyalkylene radical having an average molecular weight of from about 200 to about 10,000.
Claim 15
Dependent Claim 19 words
The method of claim 13 wherein said polyalkylene radical is selected from the group consisting of polyoxypropylene and polyoxybutylene.
Claim 16
Dependent Claim 13 words
The method of claim 14 wherein said hydrocarbyl radical is a polybutenyl radical.
Claim 17
Dependent Claim 26 words
The method of claim 14 or 15 wherein said polar radical is selected from the group consisting of primary and secondary amino, formamido, and sulfo radicals.
Claim 18
Dependent Claim 28 words
The method of claim 12 wherein said polar compound is selected from the group consisting of aliphatic hydrocarbyl substituted hydrazines, monocarboxylic acid salts of hydrocarbylamines, hydrocarbylpoly(oxyalkylene)aminoesters, hydrocarbylpoly(oxyalkylene)ureylenecarbamates, hydrocarbylcarbonates.
Claim 19
Dependent Claim 53 words
The method of claim 17 wherein said polar compound is selected from the group consisting of polyisobutenylphenylhydrazine, polyisobutenylhydroxyethylhydrazine, polyisobutenyldimethylhydrazine, polyisobutenylethylenediamine, polyisobutenylethylenediamineoxalate, polyisobutenylethylenediaminecitrate, polyisobutenylethylenediamineacetate, polyisobutenylethylenediaminelactate, polyisobutenylethylenediamineformate, polyisobutenylethylenediaminecarbonate, polypropenyldimethylpropanediamineacetate, polybutenylethylenediaminestearate, polypropenyl N',N-(dimethyltetraethylenepentamine)acetate, polyisobutenylmethylaminestearate, butylpoly(oxypropylene)N-(2-aminoethyl-2-aminopropionate, dodecylphenylpoly(oxybutylene)aminopropionate, butylpoly(oxypropylene)N-(3-dimethylaminoproply)amino-acetate, dodecylphenylpoly(oxybutylene)5-(2-aminoethylamino) valerate, butylpoly(oxypropylene)ureylene aminocarbamate, dodecylphenyl poly(oxybutylene)ureyleneaminocarbamate, polybutenyl(trimethylol propenyl)carbonate, and the reaction product of polybutenylchloroformate and N,N,N',N'-tetra-(2-hydroxypropyl)-ethylenediamine or tetra-(]-hydroxyethyl)-ethylene diamine.
Claim 20
Dependent Claim 15 words
The method of claim 1 wherein said non-volatile polar compound comprises an alkyl phenyl poly(oxyalkylene)-N-(2-aminoethylcarbamate).
Claim 21
Dependent Claim 16 words
The method of claim 11 wherein said non-volatile polar compound comprises an alkyl phenyl poly(oxy-alkylene)-N-(2- aminoethylcarbamate).
Claim 22
Dependent Claim 47 words
A motor fuel composition comprising a mixture of a hydrocarbon of the gasoline boiling range and an octane requirement increase-inhibiting amount of (a) an oil-soluble iron compound, (b) a volatile mono carboxylic acid or ester, and (c) a nonvolatile polar compound capable of solubilizing carbonaceous engine deposits.
Claim 23
Dependent Claim 47 words
A motor fuel composition comprising a mixture of a hydrocarbon of the gasoline boiling range and an octane requirement increase-inhibiting amount of (a) an oil-soluble iron compound, (b) a volatile mono carboxylic acid or ester, and (c) a nonvolatile polar compound capable of solubilizing carbonaceous engine deposits.
Claim 24
Dependent Claim 23 words
The composition of claim 21 wherein said oil-soluble iron compound is selected from the group consisting of cyclopentadienyl iron and substituted derivatives thereof.
Claim 25
Dependent Claim 45 words
The composition of claim 22 wherein said soluble iron compound is selected from the group consisting of cyclopentadienyl iron and C 1 and C 3 alkyl substituted derivatives thereof wherein one or both of the cyclopentadienyl rings are substituted with one to two alkyl groups.
Claim 26
Dependent Claim 13 words
The composition of claim 21 wherein said oil-soluble iron compound is dicyclopentadienyl iron.
Claim 27
Dependent Claim 27 words
The composition of claim 21 wherein said carboxylic acid or ester selected from the group consisting of the esters of C 2 to C 10 monocarboxylic acids.
Claim 28
Dependent Claim 30 words
The composition of claim 25 wherein said ester is the derivative of a C 2 to C 4 monocarboxylic acid and a C 4 to C 8 tertiary alkyl alcohol.
Claim 29
Dependent Claim 11 words
The composition of claim 26 wherein said ester is t-butyl acetate.
Claim 30
Dependent Claim 19 words
The composition of claim 31 wherein said oil-soluble iron compound is dicyclopentadienyl iron and said oxygen-containing compound is t-butylacetate.
Claim 31
Dependent Claim 26 words
The composition of claim 21 wherein said oil-soluble iron compound comprises from about 0.0001 to about 10 grams of iron per gallon of said fuel composition.
Claim 32
Dependent Claim 35 words
The composition of claim 29 wherein said monocarboxylic acid or ester is introduced into said engine at a concentration of from at least about 0.001 to about 10 grams per gallon of said fuel composition.
Claim 33
Dependent Claim 35 words
The composition of claim 28 wherein dicyclopentadienyl iron comprises from about 0.001 to about 5 grams of iron and said t-butylacetate comprises from about 0.001 to about 10 grams per gallon of said fuel composition.
Claim 34
Dependent Claim 48 words
The composition of claim 31 wherein said polar compound comprises a polar radical selected from the group consisting of acetoxy, amino, ammonium, carbamido, carbamyl, carbonyl, carboxy, carboxylate, cyano, formamido, formyl, hydrazino, hydroxamino, hydroxy, imino, mercapto, nitro, nitroso, phosphono, phosphonate, sulfamino, sulfamyl, sulfino, sulfinyl, sulfo, sulfonate and thiocyano radicals.
Claim 35
Dependent Claim 30 words
The composition of claim 32 wherein said radical is covalently bound to a non-polar hydrocarbyl or polyoxyalkylene radical having an average molecular weight of from about 200 to about 10,000.
Claim 36
Dependent Claim 19 words
The composition of claim 33 wherein said polyalkylene radical is selected from the group consisting of polyoxypropylene and polyoxybutylene.
Claim 37
Dependent Claim 13 words
The composition of claim 34 wherein said hydrocarbyl radical is a polybutenyl radical.
Claim 38
Dependent Claim 26 words
The composition of claim 34 or 35 wherein said polar radical is selected from the group consisting of primary and secondary amino, formamido, and sulfo radicals.
Claim 39
Dependent Claim 29 words
The composition of claim 32 wherein said polar compound is selected from the group consisting of aliphatic hydrocarbyl substituted hydrazines, monocarboxylic acid salts of hydrocarbylamines, hydrocarbylpoly(oxyalkylene)aminoesters, hydrocarbylpoly(oxyalkylene)ureylenecarbamates, and hydrocarbylcarbonates.
Claim 40
Dependent Claim 53 words
The composition of claim 37 wherein said polar compound is selected from the group consisting of polyisobutenylphenylhydrazine, polyisobutenylhydroxyethylhydrazine, polyisobutenyldimethylhydrazine, polyisobutenylethylenediamine, polyisobutenylethylenediamineoxalate, polyisobutenylethylenediaminecitrate, polyisobutenylethylenediamineacetate, polyisobutenylethylenediaminelactate, polyisobutenylethylenediamineformate, polyisobutenylethylenediaminecarbonate, polypropenyldimethylpropanediamineacetate, polybutenylethylenediaminestearate, polypropenyl N',N-(dimethyltetraethylenepentamine)acetate, polyisobutenylmethylaminestearate, butylpoly(oxypropylene)N-(2-aminoethyl-2-aminopropionate, dodecylphenylpoly(oxybutylene)aminopropionate, butylpoly(oxypropylene)N-(3-dimethylaminoproply)aminoacetate, dodecylphenylpoly(oxybutylene)5-(2-aminoethylamino) valerate, butylpoly(oxypropylene)ureylene aminocarbamate, dodecylphenyl poly(oxybutylene)ureyleneaminocarbamate, polybutenyl(trimethylol propenyl)carbonate, and the reaction product of polybutenylchloroformate and N,N,N',N'-tetra-(2-hydroxypropyl)-ethylene-diamine or tetra-(]-hydroxyethyl)ethylene diamine.
Claim 41
Dependent Claim 15 words
The composition of claim 21 wherein said non-volatile polar compound comprises an alkylphenyl poly(oxyalkylene)-N-(2-aminoethyl carbamate).
Claim 42
Dependent Claim 17 words
The composition of claim 31 wherein said non-volatile polar compound comprises an alkyl phenyl poly(oxyalkylene)-N-(2-amino ethyl carbamate).
Claim 43
Dependent Claim 86 words
A concentrate suitable for use in a liquid hydrocarbon fuel in the gasoline boiling range comprising (a) an oil-soluble iron compound, (b) a volatile mono carboxylic acid or ester, and (c) a nonvolatile polar compound capable of solubilizing carbonaceous engine deposits, and (d) a fuel compatible diluent boiling in the range of from about 50° C. (122° F.) to about 232° C. (450° F.), wherein said (a), (b) and (c) are present in an amount sufficient to provide octane increase inhibiting-effect to said liquid hydrocarbon fuel.
Claim 44
Dependent Claim 86 words
A concentrate suitable for use in a liquid hydrocarbon fuel in the gasoline boiling range comprising (a) an oil-soluble iron compound, (b) a volatile mono carboxylic acid or ester, and (c) a nonvolatile polar compound capable of solubilizing carbonaceous engine deposits, and (d) a fuel compatible diluent boiling in the range of from about 50° C. (122° F.) to about 232° C. (450° F.), wherein said (a), (b) and (c) are present in an amount sufficient to provide octane increase inhibiting-effect to said liquid hydrocarbon fuel.
Claim 45
Dependent Claim 23 words
The concentrate of claim 41 wherein said oil-soluble iron compound is selected from the group consisting of cyclopentadienyl iron and substituted derivatives thereof.
Claim 46
Dependent Claim 29 words
The concentrate of claim 41 wherein said volatile carboxylic acid or ester is selected from the group consisting of the esters of C 2 to C 10 monocarboxylic acids.
Claim 47
Dependent Claim 35 words
The concentrate of claim 41 wherein said monocarboxylic acid or ester is introduced into said engine at a concentration of from at least about 0.001 to about 10 grams per gallon of said fuel composition.
Claim 48
Dependent Claim 43 words
The concentrate of claim 42 or 43 wherein said oil-soluble iron compound comprises from about 0.01 to about 50 grams of iron and said volatile carboxylic acid or ester comprises from about 0.1 to about 100 grams per gallon of said fuel composition.
Claim 49
Dependent Claim 48 words
The concentrate of claim 41 wherein said polar compound comprises a polar radical selected from the group consisting of acetoxy, amino, ammonium, carbamido, carbamyl, carbonyl, carboxy, carboxylate, cyano, formamido, formyl, hydrazino, hydroxamino, hydroxy, imino, mercapto, nitro, nitroso, phosphono, phosphonate, sulfamino, sulfamyl, sulfino, sulfinyl, sulfo, sulfonate and thiocyano radicals.
Claim 50
Dependent Claim 30 words
The concentrate of claim 46 wherein said radical is covalently bound to a non-polar hydrocarbyl or polyoxyalkylene radical having an average molecular weight of from about 200 to about 10,000.
Claim 51
Dependent Claim 19 words
The concentrate of claim 47 wherein said polyalkylene radical is selected from the group consisting of polyoxypropylene and polyoxybutylene.
Claim 52
Dependent Claim 13 words
The concentrate of claim 48 wherein said hydrocarbyl radical is a polybutenyl radical.
Claim 53
Dependent Claim 26 words
The concentrate of claim 48 or 15 wherein said polar radical is selected from the group consisting of primary and secondary amino, formamido, and sulfo radicals.
Claim 54
Dependent Claim 29 words
The concentrate of claim 46 wherein said polar compound is selected from the group consisting of aliphatic hydrocarbyl substituted hydrazines, monocarboxylic acid salts of hydrocarbylamines, hydrocarbylpoly(oxyalkylene)aminoesters, hydrocarbylpoly(oxyalkylene)ureylenecarbamates, and hydrocarbylcarbonates.
Claim 55
Dependent Claim 53 words
The concentrate of claim 51 wherein said polar compound is selected from the group consisting of polyisobutenylphenylhydrazine, polyisobutenylhydroxyethylhydrazine, polyisobutenyldimethylhydrazine, polyisobutenylethylenediamine, polyisobutenylethylenediamineoxalate, polyisobutenylethylenediaminecitrate, polyisobutenylethylenediamineacetate, polyisobutenylethylenediaminelactate, polyisobutenylethylenediamineformate, polyisobutenylethylenediaminecarbonate, polypropenyldimethylpropanediamineacetate, polybutenylethylenediaminestearate, polypropenyl N',N-(dimethyltetraethylenepentamine)acetate, polyisobutenylmethylaminestearate, butylpoly(oxypropylene)N-(2-aminoethyl-2-aminopropionate, dodecylphenylpoly(oxybutylene)aminopropionate, butylpoly(oxypropylene)N-(3-dimethylaminoproply)aminoacetate, dodecylphenylpoly(oxybutylene)5-(2-aminoethylamino) valerate, butylpoly(oxypropylene)ureylene aminocarbamate, dodecylphenyl poly(oxybutylene)ureyleneaminocarbamate, polybutenyl(trimethylol propenyl)carbonate, and the reaction product of polybutenylchloroformate and N,N,N',N'-tetra-(2-hydroxypropyl)-ethylene-diamine or tetra-(]-hydroxyethyl)-ethylene diamine.
Claim 56
Dependent Claim 15 words
The concentrate of claim 41 wherein said non-volatile polar compound comprises an alkylphenyl poly(oxyalkylene)-N-(2-aminoethyl carbamate).
Claim 57
Dependent Claim 16 words
The concentrate of claim 45 wherein said non-volatile polar compound comprises an alkyl phenyl poly(oxyalkylene)-N-(aminoethyl carbamate).
Claim 58
Dependent Claim 21 words
The concentrate of claim 54 wherein said oil-soluble iron compound is dicyclopentadienyl iron and said carboxylic acid or ester is t-butylacetate.
Claim 59
Dependent Claim 29 words
The concentrate of claim 41 wherein said diluent is selected from the group consisting of hydrocarbons boiling in the range of from about 50° C. to about 232° C.
Claim 60
Dependent Claim 12 words
The concentrate of claim 56 wherein said hydrocarbon is an aromatic hydrocarbon.
Claim 61
Dependent Claim 20 words
The method of claim 1 wherein said nonvolatile polar compound is introduced during said intermission in a separate fuel composition.
Claim 62
Dependent Claim 21 words
The method of claim 1 wherein said nonvolatile polar compound is introduced simultaneously with said fuel composition containing (a) and (b).
Claim 63
Independent Claim 59 words
A method for operating a spark ignition internal combustion engine which comprises continuously or intermittently introducing, with the combustion intake charge to said engine, a fuel composition containing an octane requirement increase inhibitng amount of (a) an oil-soluble iron compound, (b) a volatile monocarboxylic acid or ester, and (c) a nonvolatile polar compound capable of solubilizing carbonaceous engine deposits.
Claim 64
Independent Claim 59 words
A method for operating a spark ignition internal combustion engine which comprises continuously or intermittently introducing, with the combustion intake charge to said engine, a fuel composition containing an octane requirement increase inhibitng amount of (a) an oil-soluble iron compound, (b) a volatile monocarboxylic acid or ester, and (c) a nonvolatile polar compound capable of solubilizing carbonaceous engine deposits.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-06-24 1988-12-24 1989-06-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-06-24 1992-12-24 1993-06-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-06-24 1996-12-24 1997-06-25 $7700.00 Window Closed / Lapsed

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