US4014663A
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US
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Synergistic low temperature flow improver in distillate fuel
Assignee: ExxonMobil Technology and Engineering Co
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Filing: 1975-11-28
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Granted: 1977-03-29
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Expires: 1995-11-28
Abstract
Abstract The low temperature filterability of a petroleum middle distillate fuel, such as a heating oil or a diesel fuel is improved by adding to the fuel a synergistic combination of an N-aliphatic hydrocarbyl succinamic acid or derivative thereof with a dimer of an alpha olefin, with a polymer of such dimer, or with an alkylated aromatic compound such as an alkylated diphenyl or an alkylated diphenyl ether. The olefin dimers are of alpha olefins of from 16 to 40 carbon atoms. The alkyl groups on the alkylated aromatics are derived from C16-C50 olefins or from dimers of C16-C40 alpha-olefins. This invention is particularly advantageous in improviing the flow of a diesel fuel through a fine filter at low temperatures.
Inventors
- 👤 Nicholas Feldman
- 👤 Arthur W. Langer, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 22:14
CPC Classifications
C; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/143; C10L1/16; C10L1/1608; C10L1/1625; C10L1/1633; C10L1/1641; C10L1/1691; C10L1/18; C10L1/185; C10L1/1852; C10L1/19; C10L1/20; C10L1/202; C10L1/22; C10L1/222; C10L1/2222; C10L1/2225; C10L1/224; C10L1/23; C10L1/231; C10L1/234; C10L1/238; C10L1/2383; F; F02; F02B; F02B3/00; F02B3/06
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
191 words
A petroleum middle distillate fuel which has been improved with respect to its low temperature flow properties by adding thereto a minor amount of a flow improving additive combination of synergistic proportions of: A. a hydrocarbyl succinamic acid material of the formula: ##STR7## wherein R is a straight chain aliphatic hydrocarbon having from 0 to 1 site of olefinic unsaturation and from 14 to 40 carbon atoms and attached at a secondary carbon atom to the succinyl group; one of X 2 and X 3 is --NYY 1 , wherein Y and Y 1 are aliphatic hydrocarbyl groups of from 14 to 28 carbon atoms, the other of X 2 and X 3 is of the formula: --OH(NHY.sup.2 Y.sup.3).sub.n wherein n varies from 0 to 1, Y 2 and Y 3 are hydrogen, aliphatic hydrocarbon of from 1 to 30 carbon atoms or oxyaliphatic hydrocarbon of from 1 to 30 carbon atoms, and may be taken together with the nitrogen to which they are attached to form a heterocyclic ring of from 5 to 7 annular members; and B. a derivative of an alpha olefin selected from the group consisting of:
Claim 2
Dependent Claim
191 words
A petroleum middle distillate fuel which has been improved with respect to its low temperature flow properties by adding thereto a minor amount of a flow improving additive combination of synergistic proportions of: A. a hydrocarbyl succinamic acid material of the formula: ##STR7## wherein R is a straight chain aliphatic hydrocarbon having from 0 to 1 site of olefinic unsaturation and from 14 to 40 carbon atoms and attached at a secondary carbon atom to the succinyl group; one of X 2 and X 3 is --NYY 1 , wherein Y and Y 1 are aliphatic hydrocarbyl groups of from 14 to 28 carbon atoms, the other of X 2 and X 3 is of the formula: --OH(NHY.sup.2 Y.sup.3).sub.n wherein n varies from 0 to 1, Y 2 and Y 3 are hydrogen, aliphatic hydrocarbon of from 1 to 30 carbon atoms or oxyaliphatic hydrocarbon of from 1 to 30 carbon atoms, and may be taken together with the nitrogen to which they are attached to form a heterocyclic ring of from 5 to 7 annular members; and B. a derivative of an alpha olefin selected from the group consisting of:
Claim 3
Dependent Claim
32 words
a dimer of an alpha olefin that has from 16 to 40 carbon atoms; 2. a polymer of dimer (1); 3. An aromatic compound that has been alkylated with dimer (1); and
Claim 4
Dependent Claim
32 words
a dimer of an alpha olefin that has from 16 to 40 carbon atoms; 2. a polymer of dimer (1); 3. An aromatic compound that has been alkylated with dimer (1); and
Claim 5
Dependent Claim
136 words
an aromatic compound that has been alkylated with an alpha olefin having from 16 to 50 carbon atoms; said aromatic compound that is alkylated under (3) or (4) being selected from aromatic hydrocarbons having from 1 to 3 benzene rings, from 0 to 3 alkyl groups of from 1 to 20 carbon atoms each, and from 0 to 3 other substituents per ring, said other substituents being selected from the group consisting of COOR, OR, NR 2 , F, Cl, Br and NO 2 wherein R is alkyl of 1 to 20 carbon atoms, phenyl or alkylated phenyl having 1 to 2 alkyl groups totalling 1 to 20 carbon atoms; the relative weight ratios of the additives in the combination ranging from 0.01 to 10 parts by weight of B per part by weight of A.
Claim 6
Dependent Claim
136 words
an aromatic compound that has been alkylated with an alpha olefin having from 16 to 50 carbon atoms; said aromatic compound that is alkylated under (3) or (4) being selected from aromatic hydrocarbons having from 1 to 3 benzene rings, from 0 to 3 alkyl groups of from 1 to 20 carbon atoms each, and from 0 to 3 other substituents per ring, said other substituents being selected from the group consisting of COOR, OR, NR 2 , F, Cl, Br and NO 2 wherein R is alkyl of 1 to 20 carbon atoms, phenyl or alkylated phenyl having 1 to 2 alkyl groups totalling 1 to 20 carbon atoms; the relative weight ratios of the additives in the combination ranging from 0.01 to 10 parts by weight of B per part by weight of A.
Claim 7
Dependent Claim
11 words
The fuel composition of claim 1 wherein B is alkylated diphenyl.
Claim 8
Dependent Claim
12 words
The fuel composition of claim 1 wherein B is alkylated diphenyl ether.
Claim 9
Dependent Claim
19 words
The fuel composition of claim 1 wherein B is diphenyl alkylated with the dimer of C 19 alpha olefin.
Claim 10
Dependent Claim
23 words
The fuel composition of claim 1 wherein B is diphenyl ether alkylated with a mixture of predominantly C 24 -C 28 alpha olefins.
Claim 11
Dependent Claim
23 words
The fuel composition of claim 1 wherein B is a dimer of an alpha olefin that has from 16 to 34 carbon atoms.
Claim 12
Dependent Claim
29 words
The fuel composition of claim 1 wherein B is alkyl diphenyl or alkyl diphenyl ether having from 1 to 5 alkyl groups per diphenyl group or diphenyl ether group.
Claim 13
Dependent Claim
29 words
The fuel composition of claim 1 wherein A is a hydrocarbyl succinamic acid material in which R represents hydrocarbyl groups of mixed C 15 -C 20 cracked wax olefins.
Claim 14
Dependent Claim
47 words
The fuel composition of claim 1 wherein in Component A, the said --NYY 1 group is derived from amines selected from the group consisting of: a. di(hydrogenated tallow) amine (C 16 -C 18 ); b. di(behenyl-arachidyl) amine (C 22 -C 24 ); c. mixtures of the foregoing.
Claim 15
Dependent Claim
30 words
The fuel composition of claim 1 wherein the additive combination is present in a concentration of between about 0.01 and about 3 percent by weight, based on the fuel composition.
Claim 16
Dependent Claim
15 words
The fuel composition of claim 1 wherein the middle distillate fuel is a diesel fuel.
Claim 17
Dependent Claim
15 words
The fuel composition of claim 1 wherein the middle distillate fuel is a heating oil.
Claim 18
Dependent Claim
181 words
A synergistic additive combination that has the property of improving the low temperature filterability of a petroleum distillate fuel when added thereto which comprises: A. a hydrocarbyl succinamic acid material of the formula: ##STR8## wherein R is a straight chain aliphatic hydrocarbon having from 0 to 1 site of olefinic unsaturation and from 14 to 40 carbon atoms and attached at a secondary carbon atom to the succinyl group; one of X 2 and X 3 is --NYY 1 , wherein Y and Y 1 are aliphatic hydrocarbyl groups of from 14 to 28 carbon atoms, the other of X 2 and X 3 is of the formula: --OH(NHY.sup.2 Y.sup.3).sub.n wherein n varies from 0 to 1, Y 2 and Y 3 are hydrogen, aliphatic hydrocarbon of from 1 to 30 carbon atoms or oxyaliphatic hydrocarbon of from 1 to 30 carbon atoms, and may be taken together with the nitrogen to which they are attached to form a heterocyclic ring of from 5 to 7 annular members; B. a derivative of an alpha olefin selected from the group consisting of:
Claim 19
Dependent Claim
181 words
A synergistic additive combination that has the property of improving the low temperature filterability of a petroleum distillate fuel when added thereto which comprises: A. a hydrocarbyl succinamic acid material of the formula: ##STR8## wherein R is a straight chain aliphatic hydrocarbon having from 0 to 1 site of olefinic unsaturation and from 14 to 40 carbon atoms and attached at a secondary carbon atom to the succinyl group; one of X 2 and X 3 is --NYY 1 , wherein Y and Y 1 are aliphatic hydrocarbyl groups of from 14 to 28 carbon atoms, the other of X 2 and X 3 is of the formula: --OH(NHY.sup.2 Y.sup.3).sub.n wherein n varies from 0 to 1, Y 2 and Y 3 are hydrogen, aliphatic hydrocarbon of from 1 to 30 carbon atoms or oxyaliphatic hydrocarbon of from 1 to 30 carbon atoms, and may be taken together with the nitrogen to which they are attached to form a heterocyclic ring of from 5 to 7 annular members; B. a derivative of an alpha olefin selected from the group consisting of:
Claim 20
Dependent Claim
169 words
a dimer of an alpha olefin that has from 16 to 40 carbon atoms; 2. a polymer of dimer (1); 3. an aromatic compound that has been alkylated with dimer (1); and 4. an aromatic compound that has been alkylated with an alpha olefin having from 16 to 50 carbon atoms; said aromatic compound that is alkylated under (3) or (4) being selected from aromatic hydrocarbons having from 1 to 3 benzene rings, from 0 to 3 alkyl groups of from 1 to 20 carbon atoms each, and from 0 to 3 other substituents per ring, said other substituents being selected from the group consisting of COOR, OR, NR 2 , F, Cl, Br and NO 2 wherein R is alkyl of 1 to 20 carbon atoms, phenyl or alkylated phenyl having 1 to 2 alkyl groups totalling 1 to 20 carbon atoms; the relative weight ratios of the additives in the combination ranging from 0.01 to 10 parts by weight of B per part by weight of A.
Claim 21
Dependent Claim
169 words
a dimer of an alpha olefin that has from 16 to 40 carbon atoms; 2. a polymer of dimer (1); 3. an aromatic compound that has been alkylated with dimer (1); and 4. an aromatic compound that has been alkylated with an alpha olefin having from 16 to 50 carbon atoms; said aromatic compound that is alkylated under (3) or (4) being selected from aromatic hydrocarbons having from 1 to 3 benzene rings, from 0 to 3 alkyl groups of from 1 to 20 carbon atoms each, and from 0 to 3 other substituents per ring, said other substituents being selected from the group consisting of COOR, OR, NR 2 , F, Cl, Br and NO 2 wherein R is alkyl of 1 to 20 carbon atoms, phenyl or alkylated phenyl having 1 to 2 alkyl groups totalling 1 to 20 carbon atoms; the relative weight ratios of the additives in the combination ranging from 0.01 to 10 parts by weight of B per part by weight of A.
Claim 22
Dependent Claim
21 words
An additive concentrate comprising about 3 to 60 wt. % of the additive combination of claim 13 in a hydrocarbon oil.
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) | 1980-03-28 | 1980-09-27 | 1981-03-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-28 | 1984-09-27 | 1985-03-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-28 | 1988-09-27 | 1989-03-29 | $7700.00 | Window Closed / Lapsed |