Hydrosilylation reaction catalyst

Patent metadata

Field	Value
Publication number	US-10000515-B2
Application number	US-201515503266-A
Country	US
Kind code	B2
Filing date	Aug 12, 2015
Priority date	Aug 12, 2014
Publication date	Jun 19, 2018
Grant date	Jun 19, 2018

Abstract

A hydrosilylation reaction catalyst prepared from: a catalyst precursor comprising a transition metal compound, excluding platinum, belonging to group 8-10 of the periodic table, e.g., iron acetate, cobalt acetate, nickel acetate, etc.; and a ligand comprising a carbine compound such as 1,3-dimesitylimidazol-2-ylidene, etc.. The hydrosilylation reaction catalyst has excellent handling and storage properties. As a result of using this catalyst, a hydrosilylation reaction can be promoted under gentle conditions.

First claim

The invention claimed is:

1. A hydrosilylation reaction catalyst which is prepared from:
a metal salt compound having the formula (1):
M a (L) b (X) c   (1)

wherein (i) M is Fe, Co or Ni, a is 1, b is 2, and c is 0; (ii) M is Rh, a is 2, b is 4, and c is 0; or (iii) M is Ru, a is 2, b is 4, and c is 1,
X is a halogen atom,
L is a monovalent organic group of at least one type selected from the formulae (3) to (5),
—O—R 1   (3)

—OCO—R 1   (4)

—OSO 2 —R 1   (5)

wherein R 1 is each independently an optionally substituted, C 1 -C 30 monovalent organic group which may be separated by at least one atom selected from oxygen, nitrogen, sulfur and phosphorus, or a monovalent organic group having the formula (6):
—(A) p —R 2   (6)

wherein A is a C 1 -C 30 divalent organic group which may be substituted with halogen,
p is an integer of 0 or 1, satisfying p =0 or 1 when L is a monovalent organic group having formula (3), and p =1 when L is a monovalent organic group having formula (4) or (5),
R 2 is a group having the formula (7):
—{Si(R 3 ) 2 —R 4 } s —Si(R 3 ) d {[(OSI (R 3 ) 2 )] f —R 3 } e   (7)

wherein R 3 is each independently an optionally substituted, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 6 -C 20 aryl group or C 7 -C 20 aralkyl group which may be separated by at least one atom selected from oxygen, nitrogen, sulfur and phosphorus, R 4 is a C 1 -C 10 divalent hydrocarbon group, s is an integer of 0 or 1, d is an integer of 0 to 3, e is an integer of 0 to 3, satisfying d+e =3, and f is an integer of 1 to 300, and
a carbene compound having one or two adjoining nitrogen atoms, represented by the formula (2):

wherein Y is a carbon, nitrogen or oxygen atom, g is 3 when Y is carbon, g is 2 when Y is nitrogen, g is 1 when Y is oxygen, R 4 and R 5 are each independently a C 1 -C 30 alkyl, aryl or aralkyl group which may be substituted with a halogen atom or alkoxy group, and any one of R 4 and any one of R 5 may bond together to form a divalent organic group so that the compound has a cyclic structure which may contain a nitrogen atom and/or unsaturated bond.

2. The hydrosilylation reaction catalyst of claim 1 wherein in formula (7), s is 0.

3. The hydrosilylation reaction catalyst of claim 1 which is prepared in a system where hydrosilylation reaction of a compound having an aliphatic unsaturated bond with a hydrosilane compound having a Si—H group or organohydropolysiloxane compound is carried out.

4. The hydrosilylation reaction catalyst of claim 1 wherein the carbene compound of formula (2) has the formula (8):

wherein Z is a C 2 -C 5 divalent organic group which may contain a nitrogen atom and/or unsaturated bond, R 4 and R 5 are each independently a C 1 -C 30 alkyl, aryl or aralkyl group which may be substituted with a halogen atom or alkoxy group.

5. The hydrosilylation reaction catalyst of claim 1 wherein L is a monovalent organic group having formula (4).

6. A method for preparing an addition compound comprising the step of carrying out hydrosilylation reaction of a compound having an aliphatic unsaturated bond with a hydrosilane compound having a Si—H group or organohydropolysiloxane compound in the presence of the hydrosilylation reaction catalyst of claim 1 .

7. The method for preparing an addition compound of claim 6 wherein the compound having an aliphatic unsaturated bond is an organopolysiloxane having an alkenyl group.

Assignees

• Univ Kyushu Nat Univ Corp
• Shinetsu Chemical Co

Inventors

• Nagashima Hideo
• Sunada Yusuke
• TAHARA Atsushi
• Noda Daisuke
• SOEJIMA Hiroe
• Sakuta Koji

Classifications

• B01J2531/845

  Cobalt · CPC title

• C07F7/0829 Primary

  Hydrosilylation reactions · CPC title

• B01J31/2273

  with only nitrogen as heteroatomic ring members, e.g. 1,3-diarylimidazoline-2-ylidenes · CPC title

• B01J2531/842

  Iron · CPC title

• B01J2231/323

  Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation · CPC title