Continuous process of oxidative cleavage of vegetable oils

Patent metadata

Field	Value
Publication number	US-10150725-B2
Application number	US-201715697515-A
Country	US
Kind code	B2
Filing date	Sep 7, 2017
Priority date	Dec 30, 2009
Publication date	Dec 11, 2018
Grant date	Dec 11, 2018

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

What is claimed is:

1. A continuous process for the oxidative cleavage of vegetable oils containing triglycerides of unsaturated carboxylic acids, for obtaining saturated carboxylic acids, which comprises 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, to obtain saturated monocarboxylic acids (i) and triglycerides containing saturated monocarboxylic acids with more than one acid function (ii);
c) transferring the product of step b) to an apparatus suitable to separate the saturated monocarboxylic acids (i) from the triglycerides having more than one acid function (ii); and
d) hydrolyzing with water in a third reactor said triglycerides (ii) to obtain glycerol and saturated carboxylic acids with more than one acid function, at a temperature between 150 and 350° C., at the corresponding vapor equilibrium pressure.

2. The process according to claim 1 wherein the temperature of step d) is between 180 and 320° C.

3. The process according to claim 1 wherein in step d) the water/oil ratio is between 0.5:1 and 5:1.

4. The process according to claim 2 wherein in step d) the water/oil ratio is between 0.5:1 and 5:1.

5. The process according to claim 4 wherein step d) is performed with the addition of a catalyst.

6. The process according to claim 1 wherein step d) is performed with the addition of a catalyst.

7. The process according to claim 2 wherein step d) is performed with the addition of a catalyst.

8. The process according to claim 3 wherein step d) is performed with the addition of a catalyst.

9. The process according to claim 1 wherein step d) is performed without the addition of a catalyst.

10. The process according to claim 2 wherein step d) is performed without the addition of a catalyst.

11. The process according to claim 3 wherein step d) is performed without the addition of a catalyst.

12. The process according to claim 4 wherein step d) is performed without the addition of a catalyst.

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

• C07C51/245

  of keto groups or secondary alcohol groups · 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

• C07C51/347

  by reactions not involving formation of carboxyl groups · CPC title