Process for preparing 3-glycidyloxypropyltrialkoxysilanes

Patent metadata

Field	Value
Publication number	US-10464954-B2
Application number	US-201816058762-A
Country	US
Kind code	B2
Filing date	Aug 8, 2018
Priority date	Aug 9, 2017
Publication date	Nov 5, 2019
Grant date	Nov 5, 2019

Abstract

A process can prepare a 3-glycidyloxypropylalkoxysilane of formula (I), (R′)O—(CH 2 ) 3 —Si(OR) 3 (I), where R groups are independently a methyl or ethyl group and R′ represents an H 2 C(O)CHCH 2 — group. The process includes reacting (i) a functionalized alkene of formula (II), (R′)O—C 3 H 5 (II), where R′ represents an H 2 C(O)CHCH 2 — group, with (ii) at least one hydroalkoxysilane of formula (III), HSi(OR) 3 (III), where R groups are independently a methyl or ethyl group. The reacting takes place in the presence of (iii) a Karstedt catalyst or a catalyst having hexachloroplatinic acid as a homogeneous catalyst, and (iv) 2-ethylhexanoic acid, isononanoic acid, or both. The process further includes obtaining a product of the reacting.

First claim

The invention claimed is:

1. A process for preparing a 3-glycidyloxypropylalkoxysilane of formula (I)
(R′)O—(CH 2 ) 3 —Si(OR) 3   (I)

wherein R groups are independently a methyl or ethyl group and R′ represents an H 2 C(O)CHCH 2 — group,
the process comprising:
reacting by hydrosilylation
(i) a functionalized alkene of formula (II)
(R′)O—C 3 H 5   (II)

wherein R′ represents an H 2 C(O)CHCH 2 — group
with
(ii) at least one hydroalkoxysilane of formula (III)
HSi(OR) 3   (III)

wherein R groups are independently a methyl or ethyl group,
in the presence of
(iii) a Karstedt catalyst or a catalyst comprising hexachloroplatinic acid as a homogeneous catalyst, and
(iv) 2-ethylhexanoic acid, isononanoic acid, or both,
and
obtaining a product of the hydrosilylation.

2. The process according to claim 1 , wherein the functionalized alkene (i) and the hydroalkoxysilane (ii) are used in a molar ratio of 0.8 to 1.3:1.

3. The process according to claim 1 , wherein the Karstedt catalyst or catalyst comprising hexachloroplatinic acid is used without the addition or use of any additional solvent.

4. The process according to claim 1 , wherein catalyst (iii), on a basis of a Pt content thereof, is used in a molar ratio relative to the functionalized alkene component (i) of 1:2,000,000 to 1:50,000.

5. The process according to claim 1 , wherein a Pt content of catalyst (iii) and the 2-ethylhexanoic acid and/or isononanoic acid as promoter(s) (iv) are used in a molar ratio of 1:250 to 1:25,000.

6. The process according to claim 1 , wherein
in process variant A, components (i), (ii), (iii) and (iv) are premixed, fed to a reactor or reactor system for performance of the reaction and heated to a reaction temperature while mixing, or
in process variant B, components (i), (iii) and (iv) are initially charged in or fed to a reactor or reactor system and heated to a reaction temperature while mixing, and component (ii) is metered in while mixing, or
in process variant C, components (i) and (ii) are initially charged in or fed to a reactor or reactor system and heated to a reaction temperature while mixing, and components (iii) and (iv) are metered in as such or as a mixture while mixing, or
in process variant D, components (ii), (iii) and (iv) are initially charged in or fed to a reactor or reactor system and heated to a reaction temperature while mixing, and component (i) is metered in while mixing.

7. The process according to claim 1 , wherein the reacting is conducted in a reactor at a reaction temperature between 80 and 230° C. and at a pressure of 0.5 to 20 bar abs.

8. The process according to claim 1 , further comprising:
working up the product obtained from the reacting by fractional distillation of the product obtained from the reacting to obtain a target product.

9. The process according to claim 8 , wherein the reacting and the working up are conducted batchwise or continuously.

10. The process according to claim 1 , wherein the product obtained from the reacting comprises 3-glycidyloxypropyltrimethoxysilane or 3-glycidyloxypropyltriethoxysilane, which is in acetic acid- or acetoxy-free form.

11. The process according to claim 1 , wherein the product obtained from the reacting comprises 3-glycidyloxypropyltrimethoxysilane or 3-glycidyloxypropyltriethoxysilane, and the product obtained from the reacting has a pH of 3.5 to 5.5.

12. The process according to claim 1 , wherein the product obtained from the reacting comprises 3-glycidyloxypropyltrimethoxysilane or 3-glycidyloxypropyltriethoxysilane, and the product obtained from the reacting has a conductivity value of ≤10 μS/cm.

13. 3-Glycidyloxypropyltrimethoxysilane or 3-glycidyloxypropyltriethoxysilane obtained according to the process of claim 1 .

14. The process according to claim 1 , wherein the reacting is conducted in a reactor at a reaction temperature between 100 and 200° C. and at a pressure of 0.5 to 4 bar abs.

15. The process according to claim 1 , wherein the product obtained from the reacting comprises 3-glycidyloxypropyltrimethoxysilane or 3-glycidyloxypropyltriethoxysilane, which is in acetic acid-free form.

16. The process according to claim 1 , wherein the product obtained from the reacting comprises 3-glycidyloxypropyltrimethoxysilane or 3-glycidyloxypropyltriethoxysilane, which is in acetoxy-free form.

17. The process according to claim 1 , wherein the reacting is carried out in the presence of 2-ethylhexanoic acid.

18. The process according to claim 1 , wherein the reacting is carried out in the presence of isononanoic acid.

19. The process according to claim 1 , wherein the reacting is carried out in the presence of 2-ethylhexanoic acid and isononanoic acid.

Assignees

• Evonik Degussa Gmbh

Inventors

• Rudek Markus
• Witzsche Susann
• Bade Stefan
• Drescher Claudia
• John Burkhard
• Peterle Torsten

Classifications

• C07F7/1876 Primary

  by reactions involving the formation of Si-C linkages · CPC title

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title