Process for the selective hydrogenation of vegetable oils

Patent metadata

Field	Value
Publication number	US-9650327-B2
Application number	US-201414900762-A
Country	US
Kind code	B2
Filing date	Jun 25, 2014
Priority date	Jun 27, 2013
Publication date	May 16, 2017
Grant date	May 16, 2017

Abstract

This invention relates to a process for the selective hydrogenation of vegetable oils. In particular the invention relates to a process for the hydrogenation of vegetable oils which is capable of selectively converting polyunsaturated fatty acids into mono-unsaturated fatty acids and products obtained therefrom. The vegetable oils obtained from the process according to the invention have in particular a high mono-unsaturated fatty acids content and are particularly suitable for use as raw materials for the synthesis of chemical intermediates.

First claim

The invention claimed is:

1. Process for the catalytic hydrogenation of a vegetable oil wherein the oil is placed in contact with molecular hydrogen in the presence of a catalyst comprising supported metallic Palladium, wherein said process is performed in the presence of an amount of water in an amount between 5:1 and 100:1 with respect to the weight of metallic Palladium, and at a temperature from 0° C. to 130° C.

2. Process according to claim 1 , wherein said process is performed in the presence of an amount of water from 7:1 to 50:1 with respect to the weight of metallic Palladium.

3. Process according to claim 1 , wherein the hydrogenation is performed in the presence of 30 mg/kg-500 mg/kg of metallic Palladium with respect to the vegetable oil.

4. Process according to claim 1 , wherein said catalyst comprises 0.1-1% by weight of metallic Palladium.

5. Process according to claim 1 , wherein said metallic Palladium is supported on a support selected from the group consisting of alumina, carbon, CeO 2 , ZrO 2 , CrO 2 , TiO 2 , silica, inorganic-organic sol-gel matrix, polycrystalline oxide substrates, amorphous carbon, zeolites, aluminosilicates, alkaline earth carbonates such as magnesium carbonate, calcium carbonate or barium carbonate, barium sulphate, montmorillonites, polymeric matrices, multifunctional resins, ceramic supports.

6. Process according to claim 5 , wherein the catalyst comprises metallic Palladium supported on alumina or on carbon.

7. Process according to claim 1 , wherein said process is performed at a molecular hydrogen pressure from 1 to 15 bar.

8. Process according to claim 1 , wherein said process is performed at a temperature from 70 to 130° C. and at hydrogen pressure from 1 to 6 bar.

9. Process according to claim 1 , wherein said process is performed at temperatures from 0 to 50° C., at hydrogen pressures of from 1 to 2 bar, and in the presence of an organic solvent.

10. Process according to claim 9 wherein the organic solvent is selected from hydrocarbons, esters, ketones.

11. Process according to claim 1 , wherein said vegetable oil is selected from the group consisting of soya oil, olive oil, castor oil, sunflower oil, peanut oil, maize oil, palm oil, jatropha oil, cardoon oil, cuphea oil, Brassicaceae oil, Lesquerella oil, waste frying oils, exhausted vegetable oils or mixtures thereof.

12. A process for the conversion of a polyunsaturated fatty acid into a monounsaturated fatty acid of a vegetable oil, which comprises hydrogenating the vegetable oil with at least a catalyst comprising metallic Palladium, said hydrogenating being performed in presence of an amount of water between 5:1 and 100:1 with respect to the weight of the metallic Palladium.

13. Process according to claim 12 wherein the vegetable oil is selected from the group consisting of sunflower oil, oil from Brassicaceae, cardoon oil or mixtures thereof.

14. An oxidative cleavage process wherein the staring material comprises a vegetable oil obtained from the process according to claim 1 .

15. A vegetable oil which comprises:
a di-unsaturated acid content of less than 10% by weight with respect to the total fatty acids content;
a mono-unsaturated acid content of more than 70% by weight with respect to the total fatty acids content;
a trans monounsaturated isomer content higher than 1.5% and lower than 12% by weight with respect to the total fatty acids content.

16. A vegetable oil according to claim 15 wherein the mono-unsaturated acids comprise more than 80% of 9-cis and 12-cis isomers.

17. An oxidative cleavage process wherein the staring material comprises the vegetable oil of claim 15 .

18. Process according to claim 2 , wherein the hydrogenation is performed in the presence of 30 mg/kg-500 mg/kg of metallic Palladium with respect to the vegetable oil.

19. Process according to claim 2 , wherein said catalyst comprises 0.1-1% by weight of metallic Palladium.

Assignees

• Novamont Spa

Inventors

• Borsotti Giampietro
• Capuzzi Luigi
• Digioia Francesca

Classifications

• C11C3/126 Primary

  using catalysts based principally on other metals or derivates · CPC title

• C07C51/36 Primary

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

• B01J23/44

  Palladium · CPC title