Continuous process of oxidative cleavage of vegetable oils

Patent metadata

Field	Value
Publication number	US-9790160-B2
Application number	US-201615143838-A
Country	US
Kind code	B2
Filing date	May 2, 2016
Priority date	Dec 30, 2009
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

Abstract

A continuous process for the oxidative cleavage of vegetable oils containing triglycerides of unsaturated carboxylic acids, to obtain saturated carboxylic acids, comprising feeding to a first continuous reactor a vegetable oil, an oxidizing compound and catalyst capable of catalyzing the oxidation reaction of the olefinic double bond to obtain an intermediate compound containing vicinal diols: feeding to a second continuous reactor said intermediate compound, a compound containing oxygen and a catalyst capable of catalyzing the oxidation reaction of the vicinal diols to carboxylic groups, to obtain saturated monocarboxylic acids (i) and triglycerides containing saturated carboxylic acids with more than one acid function (ii); separating the saturated monocarboxylic acids (i) from the triglycerides (ii); hydrolyzing in a third reactor the triglycerides (ii) to obtain glycerol and saturated carboxylic acids with more than one acid function; and purifying said saturated carboxylic acids by fractioned crystallization by means of wash column (melt crystallization).

First claim

The invention claimed is:

1. A continuous process for the oxidative cleavage of vegetable oils containing triglycerides of unsaturated carboxylic acids, for the obtainment of saturated carboxylic acids, comprising the steps of:
a) feeding to a first continuous reactor at least a vegetable oil and an oxidizing compound in the presence of a catalyst capable of catalyzing the oxidation reaction of the olefinic double bond to obtain an intermediate compound containing vicinal diols;
b) feeding to a second continuous reactor said intermediate compound, oxygen or a compound containing oxygen, and a catalyst capable of catalyzing the oxidation reaction of said diols to carboxylic groups in the presence of water, to obtain a product comprising saturated monocarboxylic acids (i) and triglycerides containing saturated carboxylic acids with more than one acid function (ii);
b-i) separating an aqueous phase from the product obtained as output from step b), thereby obtaining an organic phase;
c) transferring the organic phase of the product of step b-i) to an apparatus suitable to separate the saturated monocarboxylic acids (i) from the triglycerides having more than one acid function (ii); and
d) hydrolyzing in a third reactor said triglycerides (ii) to obtain glycerol and saturated carboxylic acids with more than one acid function.

2. The process according to claim 1 wherein the said step b-i) is performed by continuous centrifuging.

3. The process according to claim 2 wherein the said step b-i) is performed by means of a disc separator.

4. The process according to claim 1 wherein the said step b-i) is performed by means of a disc separator.

5. The process according to claim 4 wherein in step b-i) an organic solvent is added to improve the separation of the aqueous phase from the organic phase.

6. The process according to claim 1 wherein in step b-i) an organic solvent is added to improve the separation of the aqueous phase from the organic phase.

7. The process according to claim 2 wherein in step b-i) an organic solvent is added to improve the separation of the aqueous phase from the organic phase.

8. The process according to claim 3 wherein in step b-i) an organic solvent is added to improve the separation of the aqueous phase from the organic phase.

9. The process according to claim 8 wherein the catalysts of steps a) and b) contained in the aqueous phase of step b-i) are recovered and recycled as catalysts of step b).

10. The process according to claim 1 wherein the catalysts of steps a) and b) contained in the aqueous phase of step b-i) are recovered and recycled as catalysts of step b).

11. The process according to claim 2 wherein the catalysts of steps a) and b) contained in the aqueous phase of step b-i) are recovered and recycled as catalysts of step b).

12. The process according to claim 3 wherein the catalysts of steps a) and b) contained in the aqueous phase of step b-i) are recovered and recycled as catalysts of step b).

13. The process according to claim 4 wherein the catalysts of steps a) and b) contained in the aqueous phase of step b-i) are recovered and recycled as catalysts of step b).

14. The process according to claim 5 wherein the catalysts of steps a) and b) contained in the aqueous phase of step b-i) are recovered and recycled as catalysts of step b).

15. The process according to claim 6 wherein the catalysts of steps a) and b) contained in the aqueous phase of step b-i) are recovered and recycled as catalysts of step b).

16. The process according to claim 7 wherein the catalysts of steps a) and b) contained in the aqueous phase of step b-i) are recovered and recycled as catalysts of step b).

Assignees

• Novamont Spa

Inventors

• Bieser Arno
• Borsotti Giampietro
• Digioia Francesca
• Ferrari Adriano
• Pirocco Alessandro

Classifications

• C07C51/09 Primary

  from carboxylic acid esters or lactones · CPC title

• C07C51/353

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

• C07C51/16

  by oxidation (C07C51/145 takes precedence) · CPC title

• C07C51/285 Primary

  with peroxy-compounds · CPC title

• C07C51/245

  of keto groups or secondary alcohol groups · CPC title