Neo-alcohol compounds, processes for making same and use thereof

Patent metadata

Field	Value
Publication number	US-10584083-B2
Application number	US-201816032539-A
Country	US
Kind code	B2
Filing date	Jul 11, 2018
Priority date	Sep 29, 2017
Publication date	Mar 10, 2020
Grant date	Mar 10, 2020

Abstract

This disclosure relates to neo-alcohol compounds derivable from neo-acids, use of such neo-alcohol compounds, and processes for making neo-alcohol products.

First claim

What is claimed is:

1. A compound having a formula (F-I) below:

wherein R 1 and R 2 are identical and are a hydrocarbyl group comprising at least two (2) carbon atoms.

2. The compound of claim 1 , wherein R 1 and R 2 are a C2 to C30 linear or branched alkyl group.

3. The compound of claim 1 , wherein R 1 and R 2 are a linear alkyl group.

4. The compound of claim 2 , wherein R 1 and R 2 are selected from ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, n-icosyl, n-docosyl, n-tetracosyl, n-hexacosyl, and n-octacosyl.

5. The compound of claim 4 , wherein R 1 and R 2 are selected from n-butyl, n-hexyl, n-octyl, n-decyl, and n-dodecyl.

6. The compound of claim 1 , wherein R 1 and R 2 are a branched alkyl group.

7. The compound of claim 1 , wherein R 1 and R 2 are selected from ethylhexyl, 2-propylheptanyl, 2-butyloctyl, and 3,5-dimethyloctyl.

8. A process for making a neo-alcohol product comprising a neo-alcohol compound having a formula (F-I) below:

wherein R 1 and R 2 are identical and are a hydrocarbyl group comprising at least two (2) carbon atoms, the process comprising:
(I) providing a neo-acid product comprising a neo-acid compound having a formula (F-II) below:

and
(II) contacting the neo-acid product with a reducing agent under reducing conditions.

9. The process of claim 8 , wherein in step (II), the reducing agent is hydrogen and the reducing conditions include the presence of a hydrogenation catalyst.

10. The process of claim 9 , wherein in step (II), the reducing agent is selected from: sodium borohydride (NaBH 4 ); lithium aluminum hydride; dithionate; thiosulfates; hydrazine; a mixture of NaBH 4 and iodine; a mixture of NaBH 4 and H 2 SO 4 ; a mixture of NaBH 4 , catechol, and CF 3 COOH; a mixture of NaBH 4 and ZnC 12 ; and a mixture of NaBH 4 and cyanuric chloride.

11. The process of claim 10 , wherein the reducing conditions include a temperature in the range from 10 to 60° C., and a reaction time in the range from 0.5 to 24 hours.

12. The process of claim 8 , wherein R 1 and R 2 are a C2 to C30 linear alkyl groups.

13. The process of claim 8 , wherein R 1 and R 2 are selected from ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, n-icosyl, n-docosyl, n-tetracosyl, n-hexacosyl, and n-octacosyl.

14. The process of claim 13 , wherein R 1 and R 2 are selected from n-butyl, n-hexyl, n-octyl, n-decyl, and n-dodecyl.

15. The process of claim 8 , wherein R 1 and R 2 are a linear alkyl group.

16. The process of claim 8 , wherein step (I) comprises:
(Ia) providing a vinylidene olefin feed comprising a vinylidene olefin having the following formula (F-III):

where R 1 and R 2 correspond to the R 1 and R 2 in formula (F-I);
(Ib) contacting the vinylidene olefin with carbon monoxide in a reactor in the presence of an acid catalyst at a carbon monoxide partial pressure of at least 1.0 MPa to obtain a reaction mixture;
(Ic) contacting the reaction mixture with water to obtain an acid product mixture; and
(Id) obtaining at least a portion of the neo-acid product from the acid product mixture.

17. The process of claim 16 , wherein step (Ia) comprises the following steps:
(Ia.1) providing a monomer feed comprising a terminal olefin
where R 1 and R 2 correspond to the R 1 and R 2 in formula (F-I);
(Ia.2) oligomerizing the monomer feed in an oligomerization reactor in the presence of a catalyst system comprising a metallocene compound to obtain an oligomerization product mixture; and
(Ia.3) obtaining at least a portion of the vinylidene olefin feed from the oligomerization product mixture.

18. The process of claim 17 , wherein step (Ia.2) is carried out in a continuous process.

19. The process of claim 8 , wherein in step (I), the neo-acid compound is selected from: 2-ethyl-2-methylhexanoic acid; 2-methyl-2-propylheptanoic acid; 2-butyl-2-methyloctanoic acid; 2-methyl-2-pentylnonanoic acid; 2-hexyl-2-methyldecanoic acid; 2-heptyl-2-methylundecanoic acid; 2-methyl-2-octyldodecanoic acid; 2-decyl-2-methyltetradecanoic acid; 2-dodecyl-2-methylhexadecanoic acid; 2-methyl-2-tetradecyloctadecanoic acid; and 2-methyl-2-hexadecylicosanoic acid.

Assignees

• Exxonmobil Chemical Patents Inc
• Exxonmobile Chemical Patents Inc

Inventors

• Patil Abhimanyu O
• Lewis Kyle G
• Bodige Satish

Classifications

• C07C31/125

  containing five to twenty-two carbon atoms · CPC title

• C07C29/147 Primary

  of carboxylic acids or derivatives thereof · CPC title