Process for preparing cyclic acetals which can be used as fuel components

Patent metadata

Field	Value
Publication number	US-10087163-B2
Application number	US-201515302819-A
Country	US
Kind code	B2
Filing date	Apr 3, 2015
Priority date	Apr 7, 2014
Publication date	Oct 2, 2018
Grant date	Oct 2, 2018

Abstract

The present invention relates to a process for preparing cyclic acetals having general formula (I) wherein Y and Y′, equal to or different from each other, are selected from H and a group OR, R being a linear or branched alkyl containing from 1 to 8 carbon atoms, comprising at least the following phases: (i) providing a reaction mixture comprising at least one vicinal diol having formula (II) Z—CH 2 —CHOH—CH 2 OH wherein Z is selected from H and a group OR′, R′ being a linear or branched alkyl containing from 1 to 8 carbon atoms, said mixture being substantially free of aldehydes having general formula R I —CHO, wherein R I is a linear or branched alkyl containing from 1 to 6 carbon atoms, possibly substituted by an alkoxide group OR111, wherein R III is an alkyl containing from 1 to 4 carbon atoms; (ii) thermally treating said reaction mixture at a temperature within the range of 100° C.-300° C. in the presence of at least one acid catalyst, obtaining said compound having formula (I). The acetals having formula (I) can be used as fuel components.

First claim

The invention claimed is:

1. A process for preparing at least one compound having general formula (I):

wherein Y and Y′, the same or different, are selected from the group consisting of H and a group OR, R being a linear or branched alkyl containing from 1 to 8 carbon atoms,
comprising at least the following phases:
(i) providing a reaction mixture comprising at least a vicinal diol having formula (II)
Z—CH 2 —CHOH—CH 2 OH  (II),

wherein Z is selected from the group consisting of H and a group OR′, R′ being a linear or branched alkyl containing from 1 to 8 carbon atoms, said mixture being substantially free of aldehydes having general formula R I —CHO, wherein R I is a linear or branched alkyl containing from 1 to 6 carbon atoms, possibly substituted by an alkoxide group OR III , wherein R III is an alkyl containing from 1 to 4 carbon atoms;
(ii) thermally treating said reaction mixture at a temperature within the range of 100° C.-300° C. in the presence of at least one acid catalyst, obtaining said compound having formula (I), and
wherein the thermally treating is carried out while maintaining said reaction mixture in liquid phase.

2. The process according to claim 1 , wherein said temperature is within the range of 150° C.-200° C.

3. The process according to claim 1 , wherein said R is a linear or branched alkyl containing from 1 to 4 carbon atoms.

4. The process according to claim 1 , wherein R is selected from the group consisting of ethyl, n-butyl, i-butyl, 3-methyl-1-butyl, 2-methyl-1-butyl and mixtures thereof.

5. The process according to claim 1 , wherein said acid catalyst is selected from the group consisting of: ion-exchange acid resin, acid zeolite, silica-alumina and mixtures thereof.

6. The process according to claim 1 , wherein said vicinal diol is obtained starting from glycerine.

7. The process according to claim 6 , wherein said vicinal diol is 1,2-propanediol.

8. The process according to claim 7 , further comprising obtaining said 1,2-propanediol by a catalytic hydrogenation process of glycerine with hydrogen.

9. The process according to claim 8 , further comprising purifying by distillation said 1,2-propanediol obtained by means of said hydrogenation reaction before said thermal treatment.

10. The process according to claim 1 , wherein said vicinal diol is obtained by means of an etherification process of glycerine with at least one alcohol.

11. The process according to claim 10 , wherein said at least one alcohol is selected from the group consisting of: ethanol, n-butanol, i-butanol, 3-methyl-1-butanol, 2-methyl-1-butanol and mixtures thereof.

12. The process according to claim 6 , wherein said glycerine is obtained from a trans-esterification reaction of triglycerides.

13. The process according to claim 1 , wherein R I is a linear or branched alkyl containing from 1 to 6 carbon atoms that is substituted by an alkoxide group OR III , wherein R III is an alkyl containing from 1 to 4 carbon atoms.

14. The process according to claim 1 , wherein R is ethyl or n-butyl or mixtures thereof.

15. The process according to claim 10 , said at least one alcohol is ethanol, n-butanol or mixtures thereof.

Assignees

• Eni Spa

Inventors

• Assanelli Giulio
• De Angelis Alberto Renato

Classifications

• C07D317/12 Primary

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms · CPC title

• C10L1/1855

  Cyclic ethers, e.g. epoxides, lactides, lactones · CPC title

• C07D317/26

  Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom · CPC title

• C10L2200/0469

  Renewables or materials of biological origin · CPC title