Catalyst for hydrosilylation reaction, hydrogenation reaction, and hydrosilane reduction reaction

Abstract

Provided is a catalyst which comprises a compound represented by formula (1) and which exhibits activity for at least one type of reaction selected from among hydrosilylation reaction or hydrogenation reaction with respect to an aliphatic unsaturated bond and hydrosilane reduction reaction with respect to a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond. Formula (1): M n (L m ) {M represents Fe, Co, or Ni having an oxidation number of 0, L represents an isocyanide ligand represented by formula (2), n denotes an integer of 1-8, and m denotes an integer of 2-12. Formula (2): (CN) x —R 1 (R 1 represents a mono- to trivalent-organic group having 1-30 carbon atoms, optionally being substituted by a halogen atom, and optionally having interposed therein one or more atoms selected from among O, N, S, and Si; and x denotes an integer of 1-3.)}.

1 . A catalyst comprising a compound represented by formula (1) below, and having activity in at least one reaction selected from hydrosilylation reaction or hydrogenation reaction on an aliphatic unsaturated bond and hydrosilane reduction reaction on a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond,
   M n (L) m   (1)
   wherein M represents Fe, Co, or Ni with an oxidation number of 0, L represents an isocyanide ligand represented by formula (2) below, n represents an integer of 1 to 8, and m represents an integer of 2 to 12,
   (CN) x —R 1   (2)
 
   wherein R 1  represents a monovalent to trivalent organic group that has 1 to 30 carbon atoms, and x represents an integer of 1 to 3,   wherein the monovalent organic group that has 1 to 30 carbon atoms is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosanyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, norbornyl, adamantyl, phenyl, 1-naphthyl, 2-naphthyl, anthryl, phenanthryl, o-biphenylyl, m-biphenylyl, p-biphenylyl, tolyl, 2,6-diisopropylphenyl, a mesityl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, and an arylalkyl group having 7 to 20 carbon atoms.   
     
     
         2 . The catalyst according to  claim 1 , wherein, in the formula (2), x is 1. 
     
     
         3 . The catalyst according to  claim 1 , wherein, in the formula (1), when n=1, m=2, 4, or 5, when n=2 to 4, m=an integer of 6 to 10, and when n=8, m=12. 
     
     
         4 . The catalyst according to  claim 1 , wherein, in the formula (1), when M is Fe, n=1 and m=5, when M is Co, n=2 and m=8, and when M is Ni, n=1 and m=2 or 4, or n=3, 4, or 8 and m=4, 6, 7, or 12. 
     
     
         5 . The catalyst according to  claim 1 , wherein M in the formula (1) is Fe or Co. 
     
     
         6 . A method for producing a product of hydrosilylation reaction between an aliphatic unsaturated bond-containing compound and a Si—H bond-containing compound, wherein the method uses the catalyst according to  claim 1 . 
     
     
         7 . A method for producing a product of hydrogenation reaction of an aliphatic unsaturated bond-containing compound, wherein the method uses the catalyst according to  claim 1 . 
     
     
         8 . The production method according to  claim 6 , wherein the aliphatic unsaturated bond-containing compound is an olefin compound, or a silane compound or an organopolysiloxane having an alkenyl group bonded to a Si atom. 
     
     
         9 . A method for producing a product of reduction reaction by a Si—H bond-containing compound of a compound having a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond, wherein the method uses the catalyst according to  claim 1 . 
     
     
         10 . The method for producing a product of reduction reaction according to  claim 9 , wherein the compound having a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond is an aldehyde compound, a ketone compound, an amide compound, or a nitrile compound.