Process for the preparation of 3-heptanol from a mixture containing 2-ehthylhexanal and 3-heptyl formate

Patent metadata

Field	Value
Publication number	US-9926248-B2
Application number	US-201414902247-A
Country	US
Kind code	B2
Filing date	Jun 25, 2014
Priority date	Jul 2, 2013
Publication date	Mar 27, 2018
Grant date	Mar 27, 2018

Abstract

The invention relates to a method for producing 2,3,5-trimethyl benzoquinone or a compound containing 2,3,5-trimethyl benzoquinone, the method comprising the following steps: Oxidation of 2,3,6-trimethylphenol with oxygen or an oxygen-containing gas in a two- or multi-phase reaction medium in the presence of a catalyst or catalyst system containing at least one copper (II)-halide to a mixture containing 2,3,5-trimethyl benzoquinone, characterized in that the reaction medium contains water and at least one secondary aliphatic acyclic alcohol having 6 or more, preferably 7 or more, carbon atoms.

First claim

The invention claimed is:

1. A process for the preparation of 3-heptanol or of a mixture comprising 3-heptanol, comprising the following step:
(i) adding an aqueous solution (A) comprising one or more alkali metal hydroxide(s) to a mixture (B) at least comprising 2-ethylhexanal and 3-heptyl formate,
wherein the concentration of the alkali metal hydroxide/alkali metal hydroxides in the aqueous solution (A) is at least 40% by weight.

2. The process according to claim 1 , wherein the mixture (B) furthermore comprises one, two or all of the compounds selected from the group consisting of 2-ethylhexanoic acid, 3-heptanol and 3-heptanone.

3. A process for the preparation of 3-heptanol or of a mixture comprising 3-heptanol, comprising the following step:
(i) adding an aqueous solution (A) comprising one or more alkali metal hydroxide(s) to a mixture (B) at least comprising 2-ethylhexanal and 3-heptyl formate,
wherein the concentration of the alkali metal hydroxide/alkali metal hydroxides in the aqueous solution (A) is at least 40% by weight and
wherein the mixture (B) consists of the following constituents:
2-ethylhexanal: 10-20% by weight
3-heptyl formate: 50-60% by weight
3-heptanol: 5-10% by weight
3/4-heptanone: 8-15% by weight
2-ethylhexanoic acid: 2-5% by weight
water: <1% by weight.

4. The process according to claim 1 , wherein the alkali metal hydroxide/alkali metal hydroxides is/are selected from the group consisting of potassium hydroxide and sodium hydroxide, and combinations thereof.

5. The process according to claim 1 , wherein the concentration of the alkali metal hydroxide/alkali metal hydroxides in the aqueous solution (A) is at least 45% by weight.

6. The process according to claim 1 , wherein the molar amount of the alkali metal hydroxide/alkali metal hydroxides is at least 1.5 times the sum of the molar amounts of 3-heptyl formate, 2-ethylhexanal and 2-ethylhexanoic acid in the mixture (B).

7. The process according to claim 1 , wherein the molar amount of the alkali metal hydroxide/alkali metal hydroxides is at least 2 times the sum of the molar amounts of 3-heptyl formate, 2-ethylhexanal and 2-ethylhexanoic acid in the mixture (B).

8. The process according to claim 1 , wherein the addition of the aqueous solution (A) to the mixture (B) takes place over a period of at least 3 hours.

9. The process according to claim 1 , wherein, after the addition of the aqueous solution (A) to the mixture (B) has taken place, the resulting mixture (C) is stirred for a period of at least 6 hours.

10. The process according to claim 1 , wherein the addition of the aqueous solution (A) to the mixture (B) takes place at a temperature of at least 50° C.

11. The process according to claim 1 , wherein the addition of the aqueous solution (A) to the mixture (B) takes place at a pressure of at most 3 bar.

12. The process according to claim 1 , wherein, after the addition of the aqueous solution (A) to the mixture (B) has taken place, the resulting mixture (C) is stirred for a period of at least 12 hours.

13. The process according to claim 1 , wherein the addition of the aqueous solution (A) to the mixture (B) takes place at a temperature of at least 120° C.

14. The process according to claim 1 , wherein the addition of the aqueous solution (A) to the mixture (B) takes place at a pressure of at most 1 bar.

15. The process according to claim 12 , wherein the addition of the aqueous solution (A) to the mixture (B) takes place at a temperature of at least 120° C. and a pressure of at most 1 bar.

16. The process according to claim 1 , wherein, after the addition of the aqueous solution (A) to the mixture (B) has taken place, the resulting mixture (C) is admixed in a further reaction step (ii) with water and the phases that are formed are separated.

17. The process according to claim 11 , wherein, in a further reaction step (iii), the resulting organic phase is washed with water and is optionally then dried.

18. The process according to claim 12 , wherein, in a further reaction step (iv), the washed and optionally dried organic phase is distilled for separation into its constituents.

19. A process for the preparation of 3-heptanol or of a mixture comprising 3-heptanol, consisting essentially of the following step:
(i) adding an aqueous solution (A) comprising one or more alkali metal hydroxide(s) to a mixture (B) at least comprising 2-ethylhexanal and 3-heptyl formate,

wherein the concentration of the alkali metal hydroxide/alkali metal hydroxides in the aqueous solution (A) is at least 40% by weight.

20. The process according to claim 2 , wherein the mixture comprises 2-ethylhexanal and 3-heptyl formate in a total concentration of <5% by weight based on the mixture.

21. The process according to claim 2 , wherein the mixture comprises 2-ethylhexanal and 3-heptyl formate in a total concentration of <2% by weight, based on the mixture.

Assignees

• Basf Se

Inventors

• Teles Joaquim Henrique
• Simon Joachim
• Dehn Martine
• Danz Manuel
• Dehn Richard

Classifications

• C07C29/095

  of esters of organic acids · CPC title

• C07C29/16 Primary

  by oxo-reaction combined with reduction · CPC title

• C07C31/125

  containing five to twenty-two carbon atoms · CPC title

• C07C29/88 Primary

  by treatment giving rise to a chemical modification of at least one compound (chemisorption C07C29/76) · CPC title

• C07C29/09

  by hydrolysis · CPC title