US4416667A
Expired / Lapsed
US
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Methanol, ethanol, or gasohol fuel containing as a wear-inhibiting additive a reaction product of an ether-amine with a phosphate or a substituted phosphonic acid
Assignee: Texaco Inc
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Filing: 1981-12-31
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Granted: 1983-11-22
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Expires: 2001-12-31
Abstract
Abstract A novel fuel composition contains ethanol or gasohol plus, as a wear-inhibiting additive, a quaternary ammonium reaction product of an ether amine (R-O-R") a -NH 3-a , typically C 13 H 27 -O-(CH 2 ) 3 -NH 2 and a phosphate or phosphonate, typically tetradecyl phosphonate.
Inventors
- 👤 Benjamin J. Kaufman
- 👤 Rodney L. Sung
- 👤 William M. Sweeney
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 12:02
CPC Classifications
C; C10; C10L; C10L10/00; C10L10/08; C10L1/00; C10L1/10; C10L1/14; C10L10/04; C10L1/22; C10L1/222; C10L1/2222; C10L1/2225; C10L1/26; C10L1/2608; C10L1/2625; C10L1/2633; C10L1/2641; C10L1/2658
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
152 words
A fuel composition for internal combustion engines comprising: (a) a major portion of a fuel containing (i) at least one alcohol selected from the group consisting of ethanol and methanol and (ii) gasoline in amount of 0-50 volumes per volume of alcohol; and (b) a minor wear-inhibiting amount, 0.2-3 w %, of, as a wear-inhibiting additive, a reaction product of (i) an amine having the formula (ROR") a -NH 3-a wherein R contains 1-30 carbon atoms and is selected from the group consisting of alkyl, alkenyl, alkaryl, aralkyl, cycloalkyl, and aryl groups and R" is a divalent hydrocarbon group containing 1-30 carbon atoms and is selected from the group consisting of alkylene, alkenylene, alkarylene, aralkylene, cycloalkylene, and arylene groups, and a is an integer 1-3 with (ii) a phosphonic acid ##STR16## wherein R' contains 1-30 carbon atoms and is selected from the group consisting of alkyl, alkenyl, alkaryl, aralkyl, cycloalkyl, and aryl.
Claim 2
Dependent Claim
152 words
A fuel composition for internal combustion engines comprising: (a) a major portion of a fuel containing (i) at least one alcohol selected from the group consisting of ethanol and methanol and (ii) gasoline in amount of 0-50 volumes per volume of alcohol; and (b) a minor wear-inhibiting amount, 0.2-3 w %, of, as a wear-inhibiting additive, a reaction product of (i) an amine having the formula (ROR") a -NH 3-a wherein R contains 1-30 carbon atoms and is selected from the group consisting of alkyl, alkenyl, alkaryl, aralkyl, cycloalkyl, and aryl groups and R" is a divalent hydrocarbon group containing 1-30 carbon atoms and is selected from the group consisting of alkylene, alkenylene, alkarylene, aralkylene, cycloalkylene, and arylene groups, and a is an integer 1-3 with (ii) a phosphonic acid ##STR16## wherein R' contains 1-30 carbon atoms and is selected from the group consisting of alkyl, alkenyl, alkaryl, aralkyl, cycloalkyl, and aryl.
Claim 3
Dependent Claim
18 words
A fuel composition for internal combustion engines as claimed in claim 1 wherein said fuel is an alcohol.
Claim 4
Dependent Claim
17 words
A fuel composition for internal combustion engines as claimed in claim 1 wherein said fuel is methanol.
Claim 5
Dependent Claim
17 words
A fuel composition for internal combustion engines as claimed in claim 1 wherein said fuel is ethanol.
Claim 6
Dependent Claim
19 words
A fuel composition for internal combustion engines as claimed in claim 1 wherein said fuel is a commercial ethanol.
Claim 7
Dependent Claim
21 words
A fuel composition for internal combustion engines as claimed in claim 1 wherein said fuel is a commercial ethanol containing acid.
Claim 8
Dependent Claim
22 words
A fuel composition for internal combustion engines as claimed in claim 1 wherein said fuel is a commercial ethanol containing acetic acid.
Claim 9
Dependent Claim
18 words
A fuel composition for internal combustion engines as claimed in claim 1 wherein said fuel is a gasohol.
Claim 10
Dependent Claim
18 words
A fuel composition for internal combustion engines as claimed in claim 1 wherein said fuel is substantially anhydrous.
Claim 11
Dependent Claim
22 words
A fuel composition for internal combustion engines as claimed in claim 1 wherein said fuel contains less than 0.3 v % water.
Claim 12
Dependent Claim
13 words
A fuel composition as claimed in claim 1 wherein said amine is ROR"-NH.sub.2.
Claim 13
Dependent Claim
22 words
A fuel composition as claimed in claim 1 wherein said amine is ROR"-NH.sub.2 wherein R is a C 6 -C 15 alkyl.
Claim 14
Dependent Claim
24 words
A fuel composition as claimed in claim 1 wherein said amine is ROR"-NH.sub.2 wherein R" is a C 2 -C 3 straight chain alkyl.
Claim 15
Dependent Claim
35 words
A fuel composition as claimed in claim 1 wherein said amine is ROR"-NH.sub.2 wherein R is a C 6 -C 15 straight chain alkyl and R" is a C 2 -C 3 straight chain alkyl.
Claim 16
Dependent Claim
19 words
A fuel composition as claimed in claim 1 wherein said amine is C.sub.13 H.sub.27 O CH.sub.2 CH.sub.2 CH.sub.2 --NH.sub.2.
Claim 17
Dependent Claim
14 words
A fuel composition as claimed in claim 1 wherein said amine is (ROR").sub.3 N.
Claim 18
Dependent Claim
23 words
A fuel composition as claimed in claim 1 wherein said amine is (ROR").sub.3 N wherein R is a C 6 -C 15 alkyl.
Claim 19
Dependent Claim
25 words
A fuel composition as claimed in claim 1 wherein said amine is (ROR").sub.3 N wherein R" is a C 2 -C 3 straight chain alkyl.
Claim 20
Dependent Claim
36 words
A fuel composition as claimed in claim 1 wherein said amine is (ROR").sub.3 N wherein R is a C 6 -C 15 straight chain alkyl and R" is a C 2 -C 3 straight chain alkyl.
Claim 21
Dependent Claim
19 words
A fuel composition as claimed in claim 1 wherein said amine is (C.sub.13 H.sub.27 O CH.sub.2 CH.sub.2 CH.sub.2).sub.3 N.
Claim 22
Dependent Claim
15 words
A fuel composition as claimed in claim 1 wherein said amine is (ROR").sub.2 NH .
Claim 23
Dependent Claim
23 words
A fuel composition as claimed in claim 1 wherein said amine is (ROR").sub.2 NH wherein R is a C 6 -C 15 alkyl.
Claim 24
Dependent Claim
25 words
A fuel composition as claimed in claim 1 wherein said amine is (ROR").sub.2 NH wherein R" is a C 2 -C 3 straight chain alkyl.
Claim 25
Dependent Claim
36 words
A fuel composition as claimed in claim 1 wherein said amine is (ROR").sub.2 NH wherein R is a C 1 -C 15 straight chain alkyl and R" is a C 2 -C 3 straight chain alkyl.
Claim 26
Dependent Claim
20 words
A fuel composition as claimed in claim 1 wherein said amine is (C.sub.13 H.sub.27 O CH.sub.2 CH.sub.2 CH.sub.2).sub.2 NH .
Claim 27
Dependent Claim
25 words
A fuel composition as claimed in claim 1 wherein said phosphorus ester has the formula ##STR17## wherein R' is a C 10 -C 18 alkyl.
Claim 28
Dependent Claim
26 words
A fuel composition as claimed in claim 26 wherein R is a C 10 -C 18 alkyl and the phosphorus ester is an alkyl phosphate ester.
Claim 29
Dependent Claim
16 words
A fuel composition as claimed in claim 27 wherein the phosphorus ester is dilauryl phosphate ##STR18##
Claim 30
Dependent Claim
16 words
A fuel composition as claimed in claim 27 wherein the phosphorus ester is di-decyl phosphate ##STR19##
Claim 31
Dependent Claim
16 words
A fuel composition as claimed in claim 1 wherein the phosphonate ester contains 5-40 carbon atoms.
Claim 32
Dependent Claim
15 words
A fuel composition as claimed in claim 1 wherein the phosphonic acid is tetradecyl phosphonate.
Claim 33
Dependent Claim
20 words
A fuel composition as claimed in claim 1 wherein the amine and the ester are reacted in substantially equimolar quantities.
Claim 34
Dependent Claim
26 words
A fuel composition as claimed in claim 1 wherein the amine and the phosphonic acid are reacted in mole ratio of one phosphonic acid: two amine.
Claim 35
Dependent Claim
57 words
A fuel composition comprising a major portion of a fuel containing (i) at least one of ethanol and methanol and (ii) gasoline in amount of 0-50 volumes per volume of alcohol; and (i) 0.2 w %-10 w % of the reaction product of C 13 H 27 --O--(CH 2 ) 3 --NH 2 and (ii) di-lauryl phosphate.
Claim 36
Dependent Claim
57 words
A fuel composition comprising a major portion of a fuel containing (i) at least one of ethanol and methanol and (ii) gasoline in amount of 0-50 volumes per volume of alcohol; and (i) 0.2 w %-10 w % of the reaction product of C 13 H 27 --O--(CH 2 ) 3 --NH 2 and (ii) di-lauryl phosphate.
Claim 37
Dependent Claim
62 words
A fuel composition comprising a major portion of a fuel containing (i) at least one of ethanol and methanol and (ii) gasoline in amount of 0-50 volumes per volume of alcohol; and (i) 0.2 w %-10 w % of the reaction product of C 13 H 27 -O-(CH 2 ) 3 -NH 2 and (ii) an equimolar amount of tetradecyl phosphonic acid.
Claim 38
Dependent Claim
62 words
A fuel composition comprising a major portion of a fuel containing (i) at least one of ethanol and methanol and (ii) gasoline in amount of 0-50 volumes per volume of alcohol; and (i) 0.2 w %-10 w % of the reaction product of C 13 H 27 -O-(CH 2 ) 3 -NH 2 and (ii) an equimolar amount of tetradecyl phosphonic acid.
Claim 39
Dependent Claim
62 words
A fuel composition comprising a major portion of a fuel containing (i) at least one of ethanol and methanol and (ii) gasoline in amount of 0-50 volumes per volume of alcohol; and (i) 0.2 w %-10 w % of the reaction product of C 13 H 27 -O-(CH 2 ) 3 -NH 2 and (ii) a bimolar amount of tetradecyl phosphonic acid.
Claim 40
Dependent Claim
62 words
A fuel composition comprising a major portion of a fuel containing (i) at least one of ethanol and methanol and (ii) gasoline in amount of 0-50 volumes per volume of alcohol; and (i) 0.2 w %-10 w % of the reaction product of C 13 H 27 -O-(CH 2 ) 3 -NH 2 and (ii) a bimolar amount of tetradecyl phosphonic acid.
Claim 41
Independent Claim
147 words
The method of improving the wear-resistance properties of a fuel containing (i) at least one alcohol selected from the group consisting of ethanol and methanol and (ii) 0-50 volume of gasoline per volume of alcohol which comprises adding to said fuel a minor, wear-inhibiting amount of 0.2 -3 w % of the reaction product of (i) an amine having the formula (ROR") a -NH 3-a wherein R contains 1-30 carbon atoms and is selected from the group consisting of alkyl, alkenyl, alkaryl, aralkyl, cycloalkyl, and aryl groups and R" is a divalent hydrocarbon group containing 1-30 carbon atoms and is selected from the group consisting of alkylene, alkenylene, alkarylene, aralkylene, cycloalkylene, and arylene groups, and a is an integer 1-3 with (ii) a phosphonic acid ##STR20## wherein R' contains 1-30 carbon atoms and is selected from the group consisting of alkyl, alkenyl, alkaryl, aralkyl, cycloalkyl, and aryl.
Claim 42
Independent Claim
147 words
The method of improving the wear-resistance properties of a fuel containing (i) at least one alcohol selected from the group consisting of ethanol and methanol and (ii) 0-50 volume of gasoline per volume of alcohol which comprises adding to said fuel a minor, wear-inhibiting amount of 0.2 -3 w % of the reaction product of (i) an amine having the formula (ROR") a -NH 3-a wherein R contains 1-30 carbon atoms and is selected from the group consisting of alkyl, alkenyl, alkaryl, aralkyl, cycloalkyl, and aryl groups and R" is a divalent hydrocarbon group containing 1-30 carbon atoms and is selected from the group consisting of alkylene, alkenylene, alkarylene, aralkylene, cycloalkylene, and arylene groups, and a is an integer 1-3 with (ii) a phosphonic acid ##STR20## wherein R' contains 1-30 carbon atoms and is selected from the group consisting of alkyl, alkenyl, alkaryl, aralkyl, cycloalkyl, and aryl.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-11-21 | 1987-05-23 | 1987-11-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-11-21 | 1991-05-23 | 1991-11-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-11-21 | 1995-05-23 | 1995-11-22 | $7700.00 | Window Closed / Lapsed |