Process for producing monobranched fatty acids or alkyl esters thereof

Patent metadata

Field	Value
Publication number	US-9771543-B2
Application number	US-201314438051-A
Country	US
Kind code	B2
Filing date	Oct 7, 2013
Priority date	Oct 25, 2012
Publication date	Sep 26, 2017
Grant date	Sep 26, 2017

Abstract

A process for producing a composition having a ratio by weight of C 10 -C 26 monobranched fatty acids or alkyl esters thereof to C 10 -C 26 polybranched fatty acids or alkyl esters thereof of greater than 6 using a zeolite, preferably ferrierite, isomerization catalyst. The zeolite catalyst is preferably the only isomerization catalyst used. The zeolite catalyst can be reused many times after simple separation from the reaction products without having to be regenerated.

First claim

The invention claimed is:

1. A process for producing monobranched fatty acids or alkyl esters thereof which comprises;
(i) isomerising unsaturated C 10 -C 26 fatty acids or alkyl esters thereof in the presence of a catalyst comprising zeolite, wherein a Lewis base is not present as a co-catalyst, wherein the zeolite is a ferrierite, and wherein the isomerisation reaction is carried out at 255° C. to 350° C.,
(ii) optionally removing polymeric fatty acids,
(iii) optionally hydrogenating the reaction product of step (i) or (ii), and
(iv) obtaining a composition from the reaction product of step (i),(ii) or (iii) having a ratio by weight of C 10 -C 26 monobranched fatty acids or alkyl esters thereof to C 10 -C 26 polybranched fatty acids or alkyl esters thereof of greater than 6 and less than 100.

2. A process for producing monobranched fatty acids or alkyl esters thereof which comprises;
A) (i) isomerising unsaturated C 10 -C 26 fatty acids or alkyl esters thereof in the presence of a catalyst comprising zeolite, wherein a Lewis base is not present as a co-catalyst, wherein the zeolite is a ferrierite, and wherein the isomerisation reaction is carried out at 255° C. to 350° C.,
(ii) separating the reaction product of step (i) from the used zeolite,
(iii) optionally removing polymeric fatty acids,
(iv) optionally hydrogenating the reaction product of step (ii) or (iii),
(v) obtaining a composition from the reaction product of step (ii), (iii) or
(iv) having a ratio by weight of C 10 -C 26 monobranched fatty acids or alkyl esters thereof to C 10 -C 26 polybranched fatty acids or alkyl esters thereof of greater than 6 and less than 100, and
(B) wherein the process steps (A)(i) to (v) are repeated more than once using zeolite comprising used zeolite which has been obtained from step (A)(ii) of the previous reaction cycle.

3. The process according to claim 1 wherein the isomerisation catalyst consists of zeolite.

4. The process according to claim 1 wherein the ratio by weight of C 10 -C 26 monobranched fatty acids or alkyl esters thereof to C 10 -C 26 polybranched fatty acids or alkyl esters thereof is greater than 12.

5. The process according to claim 1 wherein the ratio by weight of C 10 -C 26 monobranched fatty acids or alkyl esters thereof to C 10 -C 26 polybranched fatty acids or alkyl esters thereof is greater than 14.

6. The process according to claim 1 wherein the composition comprises greater than 65% by weight of C 10 -C 26 monobranched fatty acids, and/or less than 8% by weight of C 10 -C 26 polybranched fatty acids, both based upon the total weight of the composition.

7. The process according to claim 6 wherein the composition comprises greater than 70% by weight of C 10 -C 26 monobranched fatty acids, and/or less than 6% by weight of C 10 -C 26 polybranched fatty acids, both based upon the total weight of the composition.

8. The process according to claim 1 wherein the composition comprises less than 20% by weight of linear fatty acids and/or less than 3% by weight of lactones, both based upon the total weight of the composition.

9. The process according to claim 2 wherein step (B), in which the zeolite is reused, occurs 3 or more times.

10. The process according to claim 2 wherein the used zeolite catalyst retains at least 90% of its activity.

11. The process according to claim 10 wherein the used zeolite catalyst retains at least 95% of its activity.

12. A steady state process comprising: isomerising unsaturated C 10 -C 26 fatty acids or alkyl esters in the presence of a zeolite catalyst to produce a composition having a ratio by weight of C 10 -C 26 monobranched fatty acids Or alkyl esters thereof to C 10 -C 26 polybranched fatty acids or alkyl esters thereof of greater than 6 and less than 100, wherein the zeolite catalyst is a ferrierite, and wherein the isomerisation reaction is carried out at 255° C. to 350° C., wherein a Lewis base is not present as a co-catalyst; and
separating the zeolite catalyst from the produced composition,
wherein the steady state process is performed continuously.

13. A composition produced by the process according to claim 1 .

14. A composition produced by the process according to claim 2 .

15. The process according to claim 1 wherein a Lewis base is not present in the isomerisation step (i).

16. The process according to claim 2 wherein a Lewis base is not present in the isomerisation step (A)(i).

Assignees

• Croda Int Plc

Inventors

• Bergen-Brenkman Tanja Van
• Rashidi Negar
• Wels Bastiaan

Classifications

• C11C3/12

  by hydrogenation · CPC title

• C11C1/002

  Sources of fatty acids, e.g. natural glycerides, characterised by the nature, the quantities or the distribution of said acids · CPC title

• C07C51/353 Primary

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

• B01J29/65

  of the ferrierite type, e.g. types ZSM-21, ZSM-35 or ZSM-38, as exemplified by patent documents US4046859, US4016245 and US4046859, respectively · CPC title

• C07C51/36

  by hydrogenation of carbon-to-carbon unsaturated bonds · CPC title