Continuous process of oxidative cleavage of vegetable oils

Patent metadata

Field	Value
Publication number	US-9346732-B2
Application number	US-201414456243-A
Country	US
Kind code	B2
Filing date	Aug 11, 2014
Priority date	Dec 30, 2009
Publication date	May 24, 2016
Grant date	May 24, 2016

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 derivatives of unsaturated carboxylic acids for the production of saturated carboxylic acids, which comprises the steps of:
a) feeding to a first continuous reactor at least a vegetable oil having an olefinic double bond 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 carboxylic acids having 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);
d) hydrolyzing in a third reactor said triglycerides (ii) to obtain glycerol and saturated carboxylic acids with more than one acid function;
e) purifying said saturated carboxylic acids with more than one acid function by fractioned crystallization by means of wash column (melt crystallization);
wherein operations to feed reagents and to remove products take place simultaneously for the entire duration of the process, and in each of said steps the process conditions remain substantially unchanged.

2. The process according to claim 1 , wherein the saturated carboxylic acids with more than one acid function of step d) are further purified by distillation in a thin film evaporator or by means of molecular distillation before step e).

3. The process according to claim 2 , wherein the evaporated carboxylic acids are further purified by means of column distillation before step e).

Assignees

• Novamont Spa

Inventors

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

Classifications

• C07C51/353

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

• C07C51/16

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

• C07C51/09 Primary

  from carboxylic acid esters or lactones · CPC title

• C07C51/245

  of keto groups or secondary alcohol groups · CPC title

• C07C51/347

  by reactions not involving formation of carboxyl groups · CPC title