Low sulfur diesel blockage inhibitor, preparation method therefor and use thereof

Patent metadata

Field	Value
Publication number	US-11912657-B2
Application number	US-201917758282-A
Country	US
Kind code	B2
Filing date	Dec 31, 2019
Priority date	Dec 31, 2019
Publication date	Feb 27, 2024
Grant date	Feb 27, 2024

Abstract

A low sulfur diesel blockage inhibitor as shown in formula (I), a preparation method therefor, and use thereof are provided. In formula (I), x and y are each an integer between 0 and 4; m and n are each selected from H, a C1-C6 linear or branched alkyl group, or a C3-C6 cycloalkyl group. By using a vegetable oil as a raw material, a modified vegetable oil fatty acid is first obtained, and then a polar group of an unsaturated dialdehyde with a certain chain length is introduced into a molecular chain of the modified vegetable oil fatty acid.

First claim

The invention claimed is:

1. A compound represented by Formula (I):

wherein x and y are each an integer between 0 and 4; m and n are each an integer between 3 and 9, and 10≤m+n≤14; and R 1 and R 2 are independently chosen from H, a C1-C6 linear or branched alkyl group, or a C3-C6 cycloalkyl group.

2. The compound according to claim 1 , wherein m is 4 or 5.

3. The compound according to claim 1 , wherein x and y are each independently 0 or 1, or m+n=12, or both.

4. The compound according to claim 1 , wherein R 1 and R 2 are independently chosen from H, methyl, or ethyl.

5. A method for preparing a vegetable oil based blockage inhibitor, wherein the method comprises the following steps:
(1) subjecting a non-conjugated vegetable oil to a haptoreaction with an alkali or an alcohol solution of an alkali under isomerization reaction condition;
(2) acidifying and washing a product obtained from the haptoreaction, and then separating out an aqueous phase to obtain a modified vegetable oil fatty acid;
(3) contacting the modified vegetable oil fatty acid with an unsaturated dialdehyde under Diels-Alder addition reaction condition to form a mixture; and
(4) removing unreacted raw materials from the mixture obtained from step (3).

6. The method according to claim 5 , wherein the non-conjugated vegetable oil of step (1) has non-conjugated carbon-carbon double bonds, a linolenic acid content of not more than 0.6%, and an iodine value of not less than 60 mgKOH/g.

7. The method according to claim 6 , wherein the non-conjugated vegetable oil of step (1) has an iodine value of not less than 85 mgKOH/g.

8. The method according to claim 7 , wherein the non-conjugated vegetable oil of step (1) is one or more selected from the group consisting of corn oil, cottonseed oil, peanut oil, sesame oil, and shinyleaf yellowhorn oil.

9. The method according to claim 5 , wherein, in step (1), the akali is potassium hydroxide and/or sodium hydroxide at an amount of 0.5-0.6 times of the non-conjugated vegetable oil by mass; the alcohol is one or more selected from the group consisting of ethylene glycol, 1,3-propanediol, and 1,4-butanediol, and an amount of said alcohol is 2.5-3.5 times of the non-conjugated vegetable oil by mass.

10. The method according to claim 5 , wherein the isomerization reaction condition in step (1) comprise a temperature of 180-220° C. and a duration of 3-5 hours.

11. The method according to claim 5 , wherein the unsaturated dialdehyde in step (3) is one or more selected from the group consisting of 2-butene dialdehyde, 2-pentene dialdehyde, 2-hexene dialdehyde, 3-hexene dialdehyde, 2-heptene dialdehyde, 3-heptene dialdehyde, 2-octene dialdehyde, 3-octene dialdehyde, and 4-octene dialdehyde.

12. The method according to claim 5 , wherein a molar ratio of unsaturated dialdehyde to vegetable oil fatty acid is 0.5:1-3:1.

13. The method according to claim 12 , wherein the molar ratio of unsaturated dialdehyde to vegetable oil fatty acid is 0.8:1-2:1.

14. The method according to claim 5 , wherein the Diels-Alder addition reaction condition of step (3) comprise a temperature of 190-210° C. and a time of 0.5-2 hours.

15. The method according to claim 5 , wherein removing the unreacted raw materials in step (4) comprises subjecting the mixture obtained from step ( 3 ) to a reduced pressure distillation under a pressure of 30-150 Pa and a temperature of 180-220° C.

16. The method according to claim 15 , wherein the reduced pressure distillation is carried out under a pressure of 65-120 Pa and a temperature of 195-205° C.

17. A low sulfur diesel blockage inhibitor composition comprising the compound according to claim 1 .

18. The low sulfur diesel blockage inhibitor composition according to claim 17 , wherein the low sulfur diesel blockage inhibitor composition comprises 70-90 wt % of vegetable oil based blockage inhibitor, 0.2-2 wt % of antioxidant, and 8-29 wt % of aromatic hydrocarbon solvent oil, based on the total amount of the low sulfur diesel blockage inhibitor composition.

19. A low sulfur diesel with improved blockage inhibition property, comprising a low sulfur diesel and a blockage inhibitor, wherein the blockage inhibitor is the compound according to claim 1 .

20. The low sulfur diesel according to claim 19 , wherein the content of said blockage inhibitor is 0.008-0.01 parts by weight relative to 100 parts by weight of the low sulfur diesel base oil.

Assignees

• China Petroleum & Chem Corp
• Sinopec Dalian Res Inst Petroleum & Petrochemicals Co Ltd

Inventors

• Li Lanpeng
• Cao Changhai
• Cheng Jin
• Li Xiuzheng
• Wang Yidi

Classifications

• C07C59/74 Primary

  containing —CHO groups · CPC title

• C07C51/353

  by isomerisation; by change of size of the carbon skeleton · CPC title

• C10L1/1881

  carboxylic group attached to an aliphatic carbon atom · CPC title

• C10L10/08

  for improving lubricity; for reducing wear · CPC title

• C10M129/93

  having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms · CPC title