Method for producing polyol esters

• US 9,284,253 B2
• Filed: 08/10/2013
• Issued: 03/15/2016
• Est. Priority Date: 09/14/2012
• Status: Active Grant

• Current Assignee: OQ Chemicals GmbH (Oxea SARL)
• Original Assignee: OXEA GmbH (Oxea SARL)
• Inventors: Frey, Guido D., Weber, Tonia, Arnold, Jrg, Kreickmann, Thorsten, Strutz, Heinz
• Primary Examiner(s): Zucker, Paul A
• Application Number:
  US14/427,742
• Publication Number:
  US 20150344400A1
• Time in Patent Office: 948 Days
• US Class Current: 1/1
• CPC Class Codes: C07C 67/08 by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
• CPC Class Codes: C07C 69/28 esterified with dihydroxylic compounds

Abstract

A process for preparing polyol esters by reacting polyols with linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atoms, is characterized in that a mixture of the starting compounds is allowed to react in the presence of a Lewis acid containing at least one element of groups 4 to 14 of the periodic table of the elements as a catalyst and in the presence of an adsorbent with removal of the water formed, and then the crude ester obtained is aftertreated by adding a further adsorbent which is an acidic activated carbon having a pH of 1 to 6.5.

Claims

1. Process for preparing polyol esters by reacting polyols of the general formula (II)

H—

(—

O—

[—

CR¹R²—

]_m—

)_o—

OH 

 

(II)

in which R¹ and R² are each independently hydrogen, an alkyl radical having 1 to 5 carbon atoms or a hydroxyalkyl radical having 1 to 5 carbon atoms, m is an integer from 1 to 10, and o is an integer from 2 to 15

with linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atoms, characterized in that a mixture of the starting compounds is allowed to react in the presence of a catalyst selected from the group consisting of titanium, zirconium, hafnium or tin as elements or in the form of compounds thereof and in the presence of an activated carbon adsorbent with removal of the water formed, and then the crude ester obtained is aftertreated by adding a further adsorbent which is an acidic activated carbon having a pH of 1 to 6.5.

2. Process according to claim 1, characterized in that the aftertreatment with the acidic activated carbon is effected at a temperature of room temperature to 140°

C.

3. Process according to claim 1, characterized in that a steam treatment is performed in the presence of the acidic activated carbon.

4. Process according to claim 3, characterized in that the steam treatment is performed at a temperature of 100 to 250°

C.

5. Process according to claim 1, characterized in that the polyol ester is dried at temperatures of 80 to 250°

C. and at pressures of 0.2 to 500 hPa.

6. Process according to claim 1, characterized in that the acidic activated carbon has a pH of 2 to 5.5.

7. Process according to claim 1, characterized in that 0.05 to 2.5 parts by weight of the acidic activated carbon are added per 100 parts by weight of crude ester to be treated.

8. Process according to claim 1, characterized in that the catalyst is used in an amount of 1.0×

10<sup>−

5</sup> to 20 mol %, based on the starting compound used in deficiency.

9. Process according to claim 8, characterized in that the catalyst is used in an amount of 0.01 to 5 mol %, based on the starting compound used in deficiency.

10. Process according to claim 1, characterized in that the tin compounds used are tin(II) oxide, tin(II) oxalate, tin(II) carboxylates, tin(IV) alkoxides or organotin compounds.

11. Process according to claim 1, characterized in that the titanium compounds used are alkoxides, acylates, carboxylates or chelates.

12. Process according to claim 1, characterized in that 0.1 to 5 parts by weight of activated carbon are used in the reaction of polyols with linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atoms per 100 parts by weight of reaction mixture.

13. Process according to claim 1, characterized in that the polyols used are ditrimethylolpropane, dipentaerythritol, diethylene glycol, triethylene glycol, tetraethylene glycol, dipropylene glycol, tripropylene glycol or tetrapropylene glycol.

14. Process according to claim 1, characterized in that the aliphatic monocarboxylic acid converted is propionic acid, n-butyric acid, isobutyric acid, n-pentanoic acid, 2-methylbutyric acid, 3-methylbutyric acid, 2-methylpentanoic acid, n-hexanoic acid, 2-ethylbutyric acid, n-heptanoic acid, 2-methylhexanoic acid, 2-ethylhexanoic acid, n-nonanoic acid, 2-methyloctanoic acid, isononanoic acid, 3,5,5-trimethylhexanoic acid or 2-propylheptanoic acid.

15. Process according to claim 1 for preparation of triethylene glycol di-2-ethylhexanoate, tetraethylene glycol di-n-heptanoate, triethylene glycol di-2-ethylbutyrate, triethylene glycol di-n-heptanoate or tetraethylene glycol di-2-ethylhexanoate.