Process for synthesizing alkenyl disiloxane

Patent metadata

Field	Value
Publication number	US-12180238-B2
Application number	US-202017784082-A
Country	US
Kind code	B2
Filing date	Dec 11, 2020
Priority date	Dec 13, 2019
Publication date	Dec 31, 2024
Grant date	Dec 31, 2024

Abstract

Described herein are methods for making alkenyl disiloxanes, comprising combining an alkenyl halosilane with a bis-hydrido terminated alkyl disiloxane and adding the mixture to water, an acidic aqueous solution, or a basic aqueous solution. The ratio of the alkenyl halosilane to the bis-hydrido terminated alkyl disiloxane is about 1:10 to about 10:1. The alkenyl halosilane and bis-hydrido terminated alkyl disiloxane are mixed at about 20° C. to about 45° C. In an example, no organic solvent is present. The reaction product is separated and washed with saturated NaHCO 3 solution (e.g., sodium bicarbonate).

First claim

The invention claimed is:

1. A process for making alkenyl disiloxanes, comprising:
combining an alkenyl halosilane with a bis-hydrido terminated alkyl disiloxane and adding the mixture to water, an acidic aqueous solution, or a basic aqueous solution.

2. The process of claim 1 , wherein the ratio of the alkenyl halosilane to the bis-hydrido terminated alkyl disiloxane is about 1:1.2 to about 1:0.6.

3. The process of claim 1 , wherein the alkenyl halosilane to the bis-hydrido terminated alkyl disiloxane are mixed at about 20° C. to about 45° C.

4. The process of claim 1 , further comprising separating D reaction product including the alkenyl disiloxane, thereby forming separated reaction product and washing the separated reaction product with an aqueous solution of a neutralizing agent.

5. The process of claim 4 , where the aqueous solution is saturated NaHCO 3 solution.

6. The process of claim 4 , further comprising drying the separated reaction product after washing.

7. The process of claim 1 , further comprising recovering the alkenyl disiloxane.

8. The process of claim 1 , wherein the alkenyl disiloxane is a compound of a Formula I:

wherein:
n is 0, 1, 2, 3, 4, 5, or 6;
R 1 is, independently at each occurrence, H or C1-3 alkyl;
R 2 is, independently at each occurrence, H or C1-3 alkyl;
also provided that one or more of R 1 and one or more of R 2 can combine to form a ring;
R 3 is, independently at each occurrence, H or C1-6 alkyl; and
R 4 is, independently at each occurrence, C1-6 alkyl.

9. The process of claim 8 , wherein the compound of Formula I is 1-(hex-5-en-1-yl)-1,1,3,3-tetramethyldisiloxane or 5-norbomen-2-yl(ethyl)-1,1,3,3-tetramethyldisiloxane.

10. The process of claim 1 , wherein the alkenyl halosilane is a compound of a Formula A:

wherein:
X is F, Cl, Br, or I;
n is 0, 1, 2, 3, 4, 5, or 6;
R 1 is, independently at each occurrence, H or C1-3 alkyl;
R 2 is, independently at each occurrence, H or C1-3 alkyl;
also provided that one or more of R 1 and one or more of R 2 can combine to form a ring; and
R 3 is, independently at each occurrence, H or C1-6 alkyl.

11. The process of claim 1 , wherein the alkenyl halosilane is 5-hexenyldimethylchlorosilane or 5-norbornen-2-yl(ethyl)chlorodimethylsilane.

12. The process of claim 1 , wherein the bis-hydrido terminated alkyl disiloxane is a compound of a Formula B:

wherein:
R 4 is, independently at each occurrence, C1-6 alkyl.

13. The process of claim 1 , wherein the bis-hydrido terminated alkyl disiloxane is 1,1,3,3,-tetramethyldisiloxane.

14. The process of claim 5 , further comprising drying the separated reaction product after washing.

15. The process of claim 2 , wherein the alkenyl disiloxane is a compound of a Formula I:

wherein:
n is 0, 1, 2, 3, 4, 5, or 6;
R 1 is, independently at each occurrence, H or C1-3 alkyl;
R 2 is, independently at each occurrence, H or C1-3 alkyl;
also provided that one or more of R 1 and one or more of R 2 can combine to form a ring;
R 3 is, independently at each occurrence, H or C1-6 alkyl; and
R 4 is, independently at each occurrence, C1-6 alkyl.

16. The process of claim 3 , wherein the alkenyl disiloxane is a compound of a Formula I:

wherein:
n is 0, 1, 2, 3, 4, 5, or 6;
R 1 is, independently at each occurrence, H or C1-3 alkyl;
R 2 is, independently at each occurrence, H or C1-3 alkyl;
also provided that one or more of R 1 and one or more of R 2 can combine to form a ring;
R 3 is, independently at each occurrence, H or C1-6 alkyl; and
R 4 is, independently at each occurrence, C1-6 alkyl.

17. The process of claim 2 , wherein the alkenyl halosilane is a compound of a Formula A:

wherein:
X is F, Cl, Br, or I;
n is 0, 1, 2, 3, 4, 5, or 6;
R 1 is, independently at each occurrence, H or C1-3 alkyl;
R 2 is, independently at each occurrence, H or C1-3 alkyl;
also provided that one or more of R 1 and one or more of R 2 can combine to form a ring; and
R 3 is, independently at each occurrence, H or C1-6 alkyl.

18. The process of claim 3 , wherein the alkenyl halosilane is a compound of a Formula A:

wherein:
X is F, Cl, Br, or I;
n is 0, 1, 2, 3, 4, 5, or 6;
R 1 is, independently at each occurrence, H or C1-3 alkyl;
R 2 is, independently at each occurrence, H or C1-3 alkyl;
also provided that one or more of R 1 and one or more of R 2 can combine to form a ring; and
R 3 is, independently at each occurrence, H or C1-6 alkyl.

19. The process of claim 2 , wherein the bis-hydrido terminated alky disiloxane is a compound of a Formula B:

wherein:
R 4 is, independently at each occurrence, C1-6 alkyl.

20. The process of claim 3 , wherein the bis-hydrido terminated alky disiloxane is a compound of a Formula B:

wherein:
R 4 is, independently at each occurrence, C1-6 alkyl.

Assignees

• Dow Silicones Corp

Inventors

• Zhou Xiaoyuan
• Li Zhanjie
• Joffre Eric

Classifications

• C07F7/20

  Purification, separation · CPC title

• C07F7/0896

  Compounds with a Si-H linkage · CPC title

• C07F7/0801 Primary

  General processes · CPC title

• C07F7/0874 Primary

  Reactions involving a bond of the Si-O-Si linkage · CPC title