Continuous process for the production of derivatives of saturated carboxylic acids

Patent metadata

Field	Value
Publication number	US-9868688-B2
Application number	US-201615049400-A
Country	US
Kind code	B2
Filing date	Feb 22, 2016
Priority date	Dec 30, 2009
Publication date	Jan 16, 2018
Grant date	Jan 16, 2018

Abstract

Provided is a continuous process for the oxidative cleavage of derivatives of unsaturated carboxylic acids for the production of saturated carboxylic acids and their derivatives which comprises the steps of:
a) feeding to a first reactor at least a derivative of an unsaturated carboxylic acid, an oxidizing compound and a catalyst capable of catalyzing the oxidation reaction of the olefinic double bond to obtain an intermediate compound containing vicinal diols, and of b) feeding to a second 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 derivatives of saturated carboxylic acids with more than one acid function (ii); c) separating the saturated monocarboxylic acids (i) from the derivatives of carboxylic acids having more than one acid function (ii).

First claim

The invention claimed is:

1. A continuous process for the oxidative cleavage of esters of unsaturated carboxylic acids for the production of saturated carboxylic acids, characterized by comprising the steps of:
a) feeding to a first continuous reactor at least an ester of an unsaturated carboxylic acid, an oxidizing compound and 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, 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 esters of saturated carboxylic acids with more than one acid function (ii);
c) separating the saturated monocarboxylic acids (i) from the esters of carboxylic acids having more than one acid function (ii);
d) hydrolyzing the esters of carboxylic acids having more than one acid function (ii) obtaining alcohol and saturated carboxylic acids having more than one acid function,
wherein in said steps a) and b the operations to feed reagents and to remove products take place simultaneously for the entire duration of the process, and in each of said step the process conditions remain substantially unchanged.

2. The process according to claim 1 , wherein the hydrolysis of step d) is performed with water, with strong acid ion exchange resins or by catalyzing the reaction with enzymes.

3. The process according to claim 1 , wherein the hydrolysis of step d) is performed with water at temperatures between 150 and 350° C. at the corresponding vapor equilibrium pressure, whereby an aqueous phase and an organic phase are formed.

4. The process according to claim 3 wherein the aqueous phase/organic phase ratio is comprised between 0.5:1 and 5:1.

5. The process according to claim 1 , wherein the hydrolysis of step d) is performed at 100° C. by continuously feeding an organic phase/aqueous phase emulsion to one or more columns containing ion exchange acid resins.

6. The process according to claim 5 , wherein said aqueous phase/organic phase weight ratio of the organic phase/aqueous emulsion is comprised between 5:1 and 2:1.

7. The process according to claim 5 , wherein said organic phase/aqueous emulsion is obtained in the presence a surfactant.

8. The process according to claim 5 , wherein said columns containing ion exchange acid resins are provided with a fractionating column on the top.

9. The process according to claim 1 , wherein said saturated carboxylic acids having more than one acid function obtained at the end of step d) are further purified by distillation and extraction in water.

Assignees

• Novamont Spa

Inventors

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

Classifications

• C07C51/353 Primary

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

• C07C67/42

  by oxidation of secondary alcohols or ketones · CPC title

• C07C51/09 Primary

  from carboxylic acid esters or lactones · CPC title

• C07C53/126

  Acids containing more than four carbon atoms · CPC title

• B01D15/361

  Ion-exchange · CPC title