US3719458A - Fuel composition - Google Patents
Fuel composition Download PDFInfo
- Publication number
- US3719458A US3719458A US00137981A US3719458DA US3719458A US 3719458 A US3719458 A US 3719458A US 00137981 A US00137981 A US 00137981A US 3719458D A US3719458D A US 3719458DA US 3719458 A US3719458 A US 3719458A
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- US
- United States
- Prior art keywords
- propanediamine
- fuel composition
- alkyl
- fuel
- substituted
- 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.)
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Classifications
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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
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
Definitions
- R is an alkyl radical having from one to four carbon atoms and R is hydrogen or an alkyl radical having from one to four carbon atoms.
- Unleaded gasolines are presently being marketed in response to these pressures. It has been observed, however, that one of the problems associated with some unleaded gasolines is that bacterial growth proceeds uninhibited in the fuel composition. This growth can proceed to the point where the bacteria formed cause fuel filter plugging in the fuel supply system of an engine.
- R is an alkyl group containing from to 30 carbon atoms
- R,, R, and R are hydrogen atoms or alkyl groups, at least two of which are hydrogen atoms
- R is an alkylene group containing from two to six carbon atoms.
- U.S. Pat. No. 2,961,309 discloses an anti-icing gasolinecomposition containing a minor amount of a glycol in combination with a mono-N-alkyl substituted- ],3-propanediamine wherein the alkyl group contains an average of 12 to 14 carbon atoms.
- U.S'. Pat. No. 2,987,385 discloses an anti-stalling gasoline composition containing the reaction mixture of lecithin and an N-aliphatic hydrocarbon substituted trimethylene diamine having the formula:
- R is an aliphatic hydrocarbon radical havingfrom eight to 20 carbon atoms.
- the fuel composition of the invention will comprise a mixture of hydrocarbons boiling in the range from about to 625F and will contain from about 0.001 to 0.005 weight percent of the prescribed bactericidal N-alkyl-substituted-l ,3-propanediamine.
- N-alkyl-substituted alkylene diamines is effective as a bactericidal additive when employed at a low concentration in a hydrocarbon fuel composition.
- Tests on closely related compounds including N-alkyl-substituted-alkylene diamines and propanediamine showed that they had essentially no bactericidal properties when employed in light distillate hydrocarbon fuels in a low concentration.
- Examples of the effective bactericidal N-alkyl-l,3- propanediamines within the scope of this invention include N-isopropyl-l,3-propanediamine, N,N-dimethyll ,3-propanediamine, N-ethyll ,3-propanediamine N.N-diethyll ,3-propanediamine and N-methyl-l ,3- propanediamine.
- the hydrocarbon fuel'compositionof the invention consists of any light distillate hydrocarbon fraction boiling in the gasoline and/or kerosene boiling ranges.
- the base fuel may consist of paraffinic, naphthenic and/or aromatic hydrocarbons or mixtures thereof suitable for use in either a spark-ignited or a turbine internal combustion engine.
- the base fuels are obtained from the distillation of crude oil, by the catalytic or thermal cracking of I gas oils, by the alkylation of isoparaffins with olefins, or by the polymerization of olefins.
- the boiling range of the base fuel will generally be in the range from 70 to 625F.
- the base fuel composition may also contain additives conventionally employed in gasoline or kerosene, such as anti-oxidants, stabilizers, dyes, anti-icing additives and the like.
- the fuel compositions of the invention were tested for their bactericidal property according to the following procedure: a sample of water was inoculated with a portion of a blood agar microorganixm culture of typical microorganisms obtained from the water bottoms of a mineral fuel oil storage tank. Five cc of the inoculated water was covered with 20 cc of the fuel sample to be tested in a one ounce bottle. The stoppered bottle was maintained at room temperature for 5 days with daily agitation. At the end of this time approximately one drop of the water phase was placed on a blood agar plate which was then maintained at room temperature for 5 days or until a growth occurred, whichever came first. A control fuel sample was run concurrently with the test fuels containing a biocide.
- the base fuel designated Base Fuel A employed in the following test was a premium grade unleaded gasoline boiling in the range from about 90 to 400F. This fuel had a research octane number of about 91. This fuel consists of about 12 percent oletinic hydrocarbons, 25 percent aromatic hydrocarbons and 63 percent saturated hydrocarbons.
- the base fuel employed in the following test was a mixture of straight run gasoline and straight run kerosene having the following values:
- a fuel composition comprising a mixture of hydrocarbons boiling in the range from about to 625F containing from about 0.001 to 0.005 volume percent of an N-alkyl-substituted-l,3-propanediamine having the formula:
- R is an alkyl radical having from one to four carbon atoms and R is hydrogen or an alkyl radical having from one to four carbon atoms.
- a motor fuel composition according to claim 1 boiling in the range from about to 425F.
- a method for producing a light hydrocarbon fuel composition having bactericidal properties which comprises adding from about 0.001 to 0.005 volume percent' of an N-alkyl-substituted-l ,3-propanediamine to a light distillate hydrocarbon fuel composition boiling in the range from about 70 to 625F, said N-alkyl-sub-' stituted-l ,3-propanediamine having the formula:
- R is an alkyl radical having from one to four carbon atoms and R is hydrogen or an alkyl radical having from one to four carbon atoms.
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Liquid Carbonaceous Fuels (AREA)
Abstract
Hydrocarbon fuel composition in the gasoline and kerosene boiling ranges having bactericidal properties containing from about 0.001 to 0.005 weight percent of an N-alkyl-substituted1,3-propanediamine having the formula:
Description
United States Patent 91 Cadorette et al.
[ FUEL COMPOSITION [75] Inventors: Raymond Cadorette; George W. Eckert, both of Wappingers'Falls, N.Y.
[73] Assignee: Texaco Inc., New York, N.Y.
[22] Filed: April 27, 1971 [21] Appl.No.: 137,981
[52] US. Cl ..44/72 [51] Int. Cl. ..Cl0l 1/22 [58] Field of Search ..44/72; 424/325 [56] References Cited UNITED STATES PATENTS 2,975,042 3/1961 Summers, Jr ..44/72 2,975,043 3/1961 Ambrose ..44/72 2,246,524
6/1941 Kyrides ..424/325 1 March 6, 1973 2,891,850 6/1959 Cosgrove et al ..44/72 Primary Examiner-Daniel E. Wyman Assistant Examiner-Mrs. Y. H. Smith Attorney-Thomas H. Whaley and Carl G. Ries [57] ABSTRACT Hydrocarbon fuel composition in the gasoline and kerosene boiling ranges having bactericidal properties containing from about 0.001 to 0.005 weight percent of an N-alkyl-substituted-l,3-propanediamine having the formula:
in which R is an alkyl radical having from one to four carbon atoms and R is hydrogen or an alkyl radical having from one to four carbon atoms.
7 Claims, No Drawings BACKGROUND OF THE INVENTION 1. Field of the Invention For many years, tetraalkyl lead compounds have been employed in gasoline to improve the octane quality of the fuel composition. The tetraalkyl lead compounds imparted a variety of valuable properties to gasoline in addition to improving the octane value. One of these properties was to inhibit the growth of bacteria in the gasoline composition. Bacteria are generally present in storage tank water bottoms and can grow rapidly in a light hydrocarbon fuel in the absence of an effective biocide or growth inhibitor.
Currently, anti-pollution drives and legislative thrust is being directed to the removal or tetraalkyl lead compounds from motor fuel composition. Unleaded gasolines are presently being marketed in response to these pressures. It has been observed, however, that one of the problems associated with some unleaded gasolines is that bacterial growth proceeds uninhibited in the fuel composition. This growth can proceed to the point where the bacteria formed cause fuel filter plugging in the fuel supply system of an engine.
2. Description of the Prior Art (1.8. Pat. No. 2,333,294 discloses a motor fuel composition having improved stability with respect to the formation of color and gum containing an alkylphenol in combination with a substituted alkylene diamine having the formula:
represented by the formula:
RI I v R4 I N--RsN R1/ s in which R is an alkyl group containing from to 30 carbon atoms; R,, R, and R are hydrogen atoms or alkyl groups, at least two of which are hydrogen atoms; and R is an alkylene group containing from two to six carbon atoms.
U.S. Pat. No. 2,961,309 discloses an anti-icing gasolinecomposition containing a minor amount of a glycol in combination with a mono-N-alkyl substituted- ],3-propanediamine wherein the alkyl group contains an average of 12 to 14 carbon atoms.
U.S'. Pat. No. 2,987,385 discloses an anti-stalling gasoline composition containing the reaction mixture of lecithin and an N-aliphatic hydrocarbon substituted trimethylene diamine having the formula:
wherein R is an aliphatic hydrocarbon radical havingfrom eight to 20 carbon atoms.
SUMMARY OF THE INVENTION of hydrocarbons in gasoline and/or kerosine boiling ranges containing a minor bactericidal amount of N- alkyl-l,3-propanediamine having the formula:
in which R is an alkyl radical having from one to four carbon atoms and R is hydrogen or an alkyl radical having from one to four carbon atoms. More specifically, the fuel composition of the invention will comprise a mixture of hydrocarbons boiling in the range from about to 625F and will contain from about 0.001 to 0.005 weight percent of the prescribed bactericidal N-alkyl-substituted-l ,3-propanediamine.
The discovery that a particular class of N-alkyl-substituted alkylene diamines is effective as a bactericidal additive when employed at a low concentration in a hydrocarbon fuel composition was unexpected. Tests on closely related compounds including N-alkyl-substituted-alkylene diamines and propanediamine showed that they had essentially no bactericidal properties when employed in light distillate hydrocarbon fuels in a low concentration.
Examples of the effective bactericidal N-alkyl-l,3- propanediamines within the scope of this invention include N-isopropyl-l,3-propanediamine, N,N-dimethyll ,3-propanediamine, N-ethyll ,3-propanediamine N.N-diethyll ,3-propanediamine and N-methyl-l ,3- propanediamine.
The hydrocarbon fuel'compositionof the invention consists of any light distillate hydrocarbon fraction boiling in the gasoline and/or kerosene boiling ranges. The base fuel may consist of paraffinic, naphthenic and/or aromatic hydrocarbons or mixtures thereof suitable for use in either a spark-ignited or a turbine internal combustion engine. The base fuels are obtained from the distillation of crude oil, by the catalytic or thermal cracking of I gas oils, by the alkylation of isoparaffins with olefins, or by the polymerization of olefins. The boiling range of the base fuel will generally be in the range from 70 to 625F. Motor fuel or gasoline generally boils from about to 425F and kerosene base or turbine fuels generally boils from about 325 to 625F. The base fuel composition may also contain additives conventionally employed in gasoline or kerosene, such as anti-oxidants, stabilizers, dyes, anti-icing additives and the like.
The fuel compositions of the invention were tested for their bactericidal property according to the following procedure: a sample of water was inoculated with a portion of a blood agar microorganixm culture of typical microorganisms obtained from the water bottoms of a mineral fuel oil storage tank. Five cc of the inoculated water was covered with 20 cc of the fuel sample to be tested in a one ounce bottle. The stoppered bottle was maintained at room temperature for 5 days with daily agitation. At the end of this time approximately one drop of the water phase was placed on a blood agar plate which was then maintained at room temperature for 5 days or until a growth occurred, whichever came first. A control fuel sample was run concurrently with the test fuels containing a biocide. The base fuel designated Base Fuel A employed in the following test was a premium grade unleaded gasoline boiling in the range from about 90 to 400F. This fuel had a research octane number of about 91. This fuel consists of about 12 percent oletinic hydrocarbons, 25 percent aromatic hydrocarbons and 63 percent saturated hydrocarbons.
The test results are set forth in the table below:
The base fuel employed in the following test was a mixture of straight run gasoline and straight run kerosene having the following values:
INSPECTION TEST ON BASE FUEL B (AVJET B) Gravity, API 56.7 Distillation Temperature, F
EP 500 Sulphur, 0.023 Freezing Point, "F 76 Heat of Combustion B.T.U./Ih ca 18,000 Luminometer No. 50 to 55 Aromatic Content, I: 16 to 18 Fuel compositions according to the invention were tested for their bactericidal property in the manner described above as set forth in the following table.
TABLE II RESULTS OF CULTURE TEST Fuel Composition Additive Culture Concentration Test 1. Base Fuel B none profuse growth 2. Base Fuel B N-isopropyl The foregoing data show that the fuel composition of the invention containing a prescribed N-alkyl-substituted 1,3-propanedramme had effective bactericidal properties. In contract, related N-alkyldiamines had no bactericidal properties.
We claim:
1. A fuel composition comprising a mixture of hydrocarbons boiling in the range from about to 625F containing from about 0.001 to 0.005 volume percent of an N-alkyl-substituted-l,3-propanediamine having the formula:
in which R is an alkyl radical having from one to four carbon atoms and R is hydrogen or an alkyl radical having from one to four carbon atoms.
2. A fuel composition according to claim 1 in which said N-alkyl-substitutedd,3-propanediamine is N-isopropyll ,3-propanediamine.
3. A fuel composition according to claim 1 in which N-alkyl-substitutedl ,3-propanediamine is N-N- dimethyl-l ,3-propanediamine.
4. A fuel composition according to claim 1 in which said N-alkyl-substituted-l,3-propanediamine is N- ethyll ,3-propanediamine.
5. A motor fuel composition according to claim 1 boiling in the range from about to 425F.
6. A turbine fuel composition according to Claim 1 boiling in the range from about 325 to 625F.
7. A method for producing a light hydrocarbon fuel composition having bactericidal properties which comprises adding from about 0.001 to 0.005 volume percent' of an N-alkyl-substituted-l ,3-propanediamine to a light distillate hydrocarbon fuel composition boiling in the range from about 70 to 625F, said N-alkyl-sub-' stituted-l ,3-propanediamine having the formula:
H N-CH CH:CH NRR in which R is an alkyl radical having from one to four carbon atoms and R is hydrogen or an alkyl radical having from one to four carbon atoms.
Claims (6)
1. A fuel composition comprising a mixture of hydrocarbons boiling in the range from about 70* to 625*F containing from about 0.001 to 0.005 volume percent of an N-alkyl-substituted-1, 3-propanediamine having the formula: H2-N-CH2CH2CH2-NRR'' in which R is an alkyl radical having from one to four carbon atoms and R'' is hydrogen or an alkyl radical having from one to four carbon atoms.
2. A fuel composition according to claim 1 in which said N-alkyl-substituted-1,3-propanediamine is N-iso-propyl-1,3-propanediamine.
3. A fuel composition according to claim 1 in which N-alkyl-substituted-1,3-propanediamine is N-N-dimethyl-1,3-propanediamine.
4. A fuel composition according to claim 1 in which said N-alkyl-substituted-1,3-propanediamine is N-ethyl-1,3-propanediamine.
5. A motor fuel composition according to claim 1 boiling in the range from about 90* to 425*F.
6. A turbine fuel composition according to Claim 1 boiling in the range from about 325* to 625*F.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13798171A | 1971-04-27 | 1971-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3719458A true US3719458A (en) | 1973-03-06 |
Family
ID=22479901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00137981A Expired - Lifetime US3719458A (en) | 1971-04-27 | 1971-04-27 | Fuel composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3719458A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166725A (en) * | 1974-10-15 | 1979-09-04 | Standard Oil Company (Indiana) | Oil-soluble biocide combination for distillate fuels |
| US20030079399A1 (en) * | 2001-09-14 | 2003-05-01 | Malfer Dennis J. | Fuels compositions for direct injection gasoline engines |
| US20150160183A1 (en) * | 2013-12-05 | 2015-06-11 | Sk Innovation Co., Ltd. | Diamine-Based Oil Marker Compositions and Method of Identifying Oil Product Using the Same |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2246524A (en) * | 1938-08-10 | 1941-06-24 | Monsanto Chemicals | Germicide |
| US2891850A (en) * | 1955-08-08 | 1959-06-23 | Shell Dev | Gasoline compositions |
| US2975043A (en) * | 1955-12-30 | 1961-03-14 | Gulf Research Development Co | Treatment of distillate fuel oils with aqueous anti-microbial agents |
| US2975042A (en) * | 1955-09-29 | 1961-03-14 | Gulf Oil Corp | Fuel oil compositions containing antimicrobial agents |
-
1971
- 1971-04-27 US US00137981A patent/US3719458A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2246524A (en) * | 1938-08-10 | 1941-06-24 | Monsanto Chemicals | Germicide |
| US2891850A (en) * | 1955-08-08 | 1959-06-23 | Shell Dev | Gasoline compositions |
| US2975042A (en) * | 1955-09-29 | 1961-03-14 | Gulf Oil Corp | Fuel oil compositions containing antimicrobial agents |
| US2975043A (en) * | 1955-12-30 | 1961-03-14 | Gulf Research Development Co | Treatment of distillate fuel oils with aqueous anti-microbial agents |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166725A (en) * | 1974-10-15 | 1979-09-04 | Standard Oil Company (Indiana) | Oil-soluble biocide combination for distillate fuels |
| US20030079399A1 (en) * | 2001-09-14 | 2003-05-01 | Malfer Dennis J. | Fuels compositions for direct injection gasoline engines |
| US7112230B2 (en) * | 2001-09-14 | 2006-09-26 | Afton Chemical Intangibles Llc | Fuels compositions for direct injection gasoline engines |
| US20150160183A1 (en) * | 2013-12-05 | 2015-06-11 | Sk Innovation Co., Ltd. | Diamine-Based Oil Marker Compositions and Method of Identifying Oil Product Using the Same |
| US9482656B2 (en) * | 2013-12-05 | 2016-11-01 | Sk Innovation Co., Ltd. | Diamine-based oil marker compositions and method of identifying oil product using the same |
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