Polymers as additives for fuels

Patent metadata

Field	Value
Publication number	US-11566196-B2
Application number	US-202117171456-A
Country	US
Kind code	B2
Filing date	Feb 9, 2021
Priority date	Dec 15, 2016
Publication date	Jan 31, 2023
Grant date	Jan 31, 2023

Abstract

A method minimizes power loss in a direct injection diesel engine by adding a copolymer to a diesel fuel composition. The copolymer contains, in a copolymerized form, (A) maleic anhydride, (B) an α-olefin having from 12 to 30 carbon atoms, (C) optionally an additional aliphatic or cycloaliphatic olefin which has at least 4 carbon atoms and is different from monomer (B), and (D) optionally an additional copolymerizable monomer other than monomers (A), (B) and (C). Monomer (D) can be a vinyl ester, a vinyl ether, a (meth)acrylic ester of an alcohol having at least 5 carbon atoms, an allyl alcohol or an ester thereof, a N-vinyl compound, an ethylenically unsaturated aromatic, an α,β-ethylenically unsaturated nitrile, a (meth)acrylamide, or an allylamine. Anhydride functionalities present in the copolymer are partly reacted with at least one compound (E) comprising an alcohol group and/or an amino group, and the anhydride functionalities present are hydrolyzed.

First claim

The invention claimed is:

1. A method for minimizing power loss in a direct injection diesel engine, the method comprising:
adding a copolymer to a diesel fuel composition,
wherein the copolymer comprises, in a copolymerized form:
(A) maleic anhydride,
(B) an α-olefin having from 12 to 30 carbon atoms,
(C) optionally an additional aliphatic or cycloaliphatic olefin which has at least 4 carbon atoms and is different from monomer (B) and
(D) optionally an additional copolymerizable monomer other than monomers (A), (B) and (C), selected from the group consisting of
(Da) a vinyl ester,
(Db) a vinyl ether,
(Dc) a (meth)acrylic ester of an alcohol having at least 5 carbon atoms,
(Dd) an allyl alcohol or an ester thereof,
(De) a N-vinyl compound selected from the group consisting of a vinyl compound of a heterocycle containing at least one nitrogen atom, a N-vinylamide and a N-vinyllactam,
(Df) an ethylenically unsaturated aromatic,
(Dg) an α,β-ethylenically unsaturated nitrile,
(Dh) a (meth)acrylamide, and
(Di) an allylamine,
wherein anhydride functionalities present in the copolymer are partly reacted with at least one compound (E) comprising an alcohol group and/or an amino group, and the anhydride functionalities present in the copolymer are hydrolyzed.

2. The method according to claim 1 , wherein the at least one compound (E) is selected from the group consisting of a monoalcohol, a diol, a polyol, a monoamine, a diamine, a polyamine and an amino alcohol.

3. The method according to claim 2 , wherein the at least one compound (E) is a monoalcohol,
the monoalcohol is a compound of formula (I):
R 1 —O—[—X i —] n —H  (1)

wherein
R 1 is a straight-chain or branched C 1 - to C 200 -alkyl or C 1 - to C 200 -alkenyl radical and
n is 0 or a positive integer from 1 to 50, and
each X i , where i=1 to n, is optionally independently selected from the group consisting of —CH 2 —CH 2 —O—, —CH 2 —CH(CH 3 )—O—, —CH(CH 3 )—CH 2 —O—, —CH 2 —C(CH 3 ) 2 —O—, —C(CH 3 ) 2 —CH 2 —O—, —CH 2 —CH(C 2 H 5 )—O—, —CH(C 2 H 5 )—CH 2 —O— and —CH(CH 3 )—CH(CH 3 )—O—.

4. The method according to claim 2 , wherein the at least one compound (E) is a monoamine and
the monoamine is a monoamine having 6 to 200 carbon atoms.

5. The method according to claim 4 , wherein the monoamine has formula (II):

wherein
R 2 is hydrogen or C 1-20 -alkyl, and
R 3 is C 12-200 -alkyl which is optionally linear or branched.

6. The method according to claim 5 , wherein the monoamine is a polyisobuteneamine based on a polyisobutene having a weight average molecular weight of 550 to 2300 g/mol.

7. The method according to claim 4 , wherein the monoamine is a monoalkylamine having 6 to 200 carbon atoms or a dialkylamine.

8. The method according to claim 2 , wherein the at least one compound (E) is a polyamine and
the polyamine is a polyethyleneamine.

9. The method according to claim 8 , wherein the polyamine is selected from the group consisting of ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, and pentaethylenehexamine.

10. The method according to claim 2 , wherein the at least one compound (E) is a compound (E2) selected from the group consisting of 2-dimethylaminoethylamine, 3-dimethylaminopropylamine, and N′,N″,N″-trimethyldiethylenetriamine.

11. The method according to claim 1 , wherein the power loss is caused by introduction of zinc into the diesel fuel.

12. The method according to claim 1 , wherein the power loss is caused by introduction of sodium into the diesel fuel.

13. The method according to claim 1 , wherein the power loss is caused by K, Zn, Ca, and/or Na ions.

14. The method according to claim 1 , wherein the direct injection diesel engine is a diesel engine with a common rail injection system.

15. The method according to claim 1 , wherein the copolymer is added to the diesel fuel in an amount effective for reducing formation of ionic and/or polymeric deposits in the injection system, in comparison to a method using the same amount of a comparative fuel that is the same as the diesel fuel but does not contain the copolymer.

16. A method for reducing power loss during operation of a direct injection diesel engine, comprising:
injecting a diesel fuel into a direct injection diesel engine through a fuel system in fluid communication with the direct injection diesel engine, wherein the fuel system comprises an injection system having injection nozzles and a common rail, and
combusting the diesel fuel in the direct injection diesel engine;
wherein the diesel fuel comprises at least one copolymer m an amount effective for minimizing power loss in a direct injection diesel engine in comparison to a method of injecting and combusting the same amount of a comparative fuel that is the same as the diesel fuel hut does not contain the copolymer;
wherein the copolymer comprises, in a copolymerized form:
(A) maleic anhydride,
(B) an α-olefin having from 12 to 30 carbon atoms,
(C) optionally an additional aliphatic or cycloaliphatic olefin which has at least 4 carbon atoms and is different from monomer (B) and
(D) optionally an additional copolymerizable monomer other than monomers (A), (B) and (C), selected from the group consisting of
(Da) a vinyl ester,
(Db) a vinyl ether,
(Dc) a (meth)acrylic ester of an alcohol having at least 5 carbon atoms,
(Dd) an allyl alcohol or an ester thereof,
(De) a N-vinyl compound selected from the group consisting of a vinyl compound of a heterocycle containing at least one nitrogen atom, a N-vinylamide and a N-vinyllactam,
(Df) an ethylenically unsaturated aromatic,
(Dg) an α,β-ethylenically unsaturated nitrile,
(Dh) a (meth)acrylamide, and
(Di) an allylamine,
wherein the copolymer has one or more anhydride functionalities reacted with a compound (E) comprising an alcohol group and/or an amino group, and at least a portion of the anhydride functionalities are hydrolyzed.

17. The method according to claim 16 , wherein the power loss is caused by introduction of sodium into the diesel fuel.

18. The method according to claim 16 , wherein the power loss is caused by introduction of zinc into the diesel fuel.

19. The method according to claim 16 , wherein the power loss is caused by K, Zn, Ca, and/or Na ions.

20. The method according to claim 16 , wherein the direct injection diesel engine is a diesel engine with a common rail injection system.

Assignees

• Basf Se

Inventors

• Peretolchin Maxim
• Garcia Castro Ivette
• Flores-Figueroa Aaron

Classifications

• C10L1/1966

  poly-carboxylic · CPC title

• C10L10/06

  for facilitating soot removal · CPC title

• C10L2270/026

  for diesel engines, e.g. automobiles, stationary, marine · CPC title

• C10L1/2364

  homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups (C10L1/221 takes precedence) · CPC title

• C10L1/1963 Primary

  mono-carboxylic · CPC title