JPH11158187A - Production of compound containing silicon and polymer-containing silicon - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an industrially useful compound containing silicon and having acetylene bond, and polymer containing silicon simply by reacting a specific (hydro) silyl compound with a (di)ethynyl compound in the presence of metal compounds. SOLUTION: This compound containing silicon consisting of a silylacetylene compound expressed by formula I [(i) is <= m positive integer], is obtained by reacting a silyl compound expressed by the formula: R4-m SiHm [(m) is <=4 positive integer; R is a 1-30C alkyl, an akenyl, an alkinyl, phenyl, naphthyl or the like] with an ethynyl compound expressed by the formula: R<1> -C≡CH (R<1> is H or the same kind as R) in the presence of metal compounds. Further, a polymer containing silicon of formula IV or V is obtained by reacting a hydrosilyl compound expressed by formula II (R<2> , R<3> are the same kind with R<1> ) with a diethynyl compound expressed by formula III [R<4> is a 1-30C alkylene, phenylene or the like; (n) is 0, <=4 positive integer] in the presence of metal compounds.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel process for producing industrially useful silicon-containing compounds and polymers from silyl compounds and acetylene compounds using metal compounds as catalysts.

[0002]

2. Description of the Related Art Conventionally, as a method for synthesizing a silicon-containing compound or a silicon-containing polymer having an acetylene bond from a silyl compound and an acetylene compound, cuprous chloride described in a paper by JF Harrod et al. With cocatalyst (Hua Qin Liu and John F. Harr
od, Canadian Journal of Chemistry, Vol. 68, 1100-1
105 (1990)), a method using a basic metal oxide catalyst proposed by the present inventors (for example, see JP-A-5-345825,
Japanese Patent Application No. 4-240593 is known. But J.
In the method of F. Harrod et al., It is difficult to remove the amine compound as a cocatalyst. In addition, the method using a basic metal oxide catalyst requires time and effort for catalyst activation such as thermal decomposition of a metal hydroxide at a high temperature.

[0003]

DISCLOSURE OF THE INVENTION The present inventors have conducted intensive studies in order to solve the above-mentioned problems, and as a result, using a metal compound as a catalyst, a silicon-containing compound having an acetylene bond can be more efficiently used than a silyl compound and an ethynyl compound. It has also been found that a silicon-containing polymer can be easily obtained from a hydrosilyl compound and a diethynyl compound.

[0004]

SUMMARY OF THE INVENTION The present invention provides a method for producing R _4-m -Si
H _m (wherein, m is a positive integer of 4 or less, and R is an aromatic group such as an alkyl group, an alkenyl group, an alkynyl group, a phenyl group or a naphthyl group having 1 to 30 carbon atoms, and is a halogen atom, a hydroxyl group. , An amino group, a carboxyl group, an ether group, etc., where m is 1 or 2
R may be the same or different. )
In silyl compound R ¹ -C≡CH (wherein represented, R ¹ is an aromatic group such as an alkyl group, an alkenyl group, an alkynyl group, a phenyl group or a naphthyl group number of 1 to 30 hydrogen or C A ethynyl compound represented by the general formula (1), which may contain a substituent such as a halogen atom, a hydroxyl group, an amino group, a carboxyl group, or an ether group) in the presence of a metal compound. 1) (Chem. 5)

[0005]

Embedded image (In the formula, m is a positive integer of 4 or less, and R is an aromatic group such as an alkyl group, an alkenyl group, an alkynyl group, a phenyl group or a naphthyl group having 1 to 30 carbon atoms, and is a halogen atom, a hydroxyl group, an amino group. And m may contain a substituent such as a carboxyl group, an ether group, etc. When m is 1 or 2, each R may be the same or different, and R ¹ may be a hydrogen atom or a C 1-30 group. An aromatic group such as an alkyl group, an alkenyl group, an alkynyl group, a phenyl group, and a naphthyl group, which may contain a substituent such as a halogen atom, a hydroxyl group, an amino group, a carboxyl group, or an ether group. This is a method for producing a silylacetylene compound represented by the formula:

In the present invention, R ² —SiH ₂ —R ³ (wherein R ² and R ³ independently represent a hydrogen atom or an alkyl, alkenyl, alkynyl or phenyl group having 1 to 30 carbon atoms) Or an aromatic group such as a naphthyl group, which may contain a substituent such as a halogen atom, a hydroxyl group, an amino group, a carboxyl group, or an ether group.) Formula (2)

[0007]

Embedded image (In the formula, R ⁴ is a divalent aromatic group such as an alkylene group, alkenylene group, alkynylene group, phenylene group, or naphthylene group having 1 to 30 carbon atoms, or an aromatic group having 1 to 30 carbon atoms directly or by a crosslinking member. Alkylene group, alkenylene group, alkynylene group, a group linked to an aromatic group,
These groups may include a substituent such as a halogen atom, a hydroxyl group, an amino group, a carboxyl group, and an ether group. n is 0 or a positive integer of 4 or less. Wherein the diethynyl compound represented by the general formula (3) is reacted in the presence of a metal compound.

[0008]

Embedded image (Wherein R ² and R ³ are each independently a hydrogen atom or an aromatic group such as an alkyl group having 1 to 30 carbon atoms, an alkenyl group, an alkynyl group, a phenyl group or a naphthyl group,
These groups may include a substituent such as a halogen atom, a hydroxyl group, an amino group, a carboxyl group, and an ether group. ) Or general formula (4)

[0009]

Embedded image (Wherein R ² and R ³ are each independently a hydrogen atom or an aromatic group such as an alkyl group having 1 to 30 carbon atoms, an alkenyl group, an alkynyl group, a phenyl group or a naphthyl group,
These groups may include a substituent such as a halogen atom, a hydroxyl group, an amino group, a carboxyl group, and an ether group. R ⁴ is an alkylene group having 1 to 30 carbon atoms such as an alkylene group having 1 to 30 carbon atoms, an alkenylene group, an alkynylene group, a divalent aromatic group such as a phenylene group or a naphthylene group, It is a group linked to an alkenylene group, an alkynylene group, or an aromatic group, and these groups may include a substituent such as a halogen atom, a hydroxyl group, an amino group, a carboxyl group, or an ether group.
n is 0 or a positive integer of 4 or less. This is a method for producing a silicon-containing polymer having an acetylene bond containing a repeating unit represented by the following formula:

Further, the present invention is characterized in that a silyl compound represented by R _4-m -SiH _m and an ethynyl compound represented by R ¹ -C≡CH are reacted in the presence of a metal compound. A method for producing a silylacetylene compound represented by the general formula (1), wherein the metal compound is an organometallic compound in the method for producing a silylacetylene compound represented by the general formula (1). Further, the present invention relates to R
_4-m silyl compound represented by -SiH _m and R ¹ -C≡CH
Wherein the metal compound is an alkoxide in the method for producing a silylacetylene compound represented by the general formula (1), wherein the ethynyl compound is reacted in the presence of a metal compound. This is a method for producing a silylacetylene compound represented by the general formula (1). Further, the present invention provides a compound represented by the general formula (R) wherein a silyl compound represented by R _4-m -SiH _m and an ethynyl compound represented by R ¹ -C≡CH are reacted in the presence of a metal compound. A method for producing a silylacetylene compound represented by the general formula (1), wherein the metal compound is a metal amide in the method for producing a silylacetylene compound represented by 1).

Further, the present invention is characterized in that a hydrosilyl compound represented by R ² —SiH ₂ —R ³ is reacted with acetylene or a diethynyl compound represented by the general formula (2) in the presence of a metal compound. In the method for producing a silicon-containing polymer having an acetylene bond containing a repeating unit represented by the general formula (3) or (4), the metal compound is an organometallic compound. ) Or a method for producing a silicon-containing polymer having an acetylene bond containing a repeating unit represented by the general formula (4). In addition, the present invention is characterized by reacting a hydrosilyl compound represented by R ² —SiH ₂ —R ³ with acetylene or a diethynyl compound represented by the general formula (2) in the presence of a metal compound. In the method for producing a silicon-containing polymer having an acetylene bond containing a repeating unit represented by (3) or (4), the metal compound is an alkoxide, wherein the metal compound is an alkoxide. This is a method for producing a silicon-containing polymer having an acetylene bond containing a repeating unit represented by 4). In addition, the present invention relates to a hydrosilyl compound represented by R ² —SiH ₂ —R ³ and acetylene or the general formula (2)
A method for producing a silicon-containing polymer having an acetylene bond containing a repeating unit represented by the general formula (3) or (4), characterized by reacting a diethynyl compound represented by the following formula (1) with a metal compound: Wherein the metal compound is a metal amide
Or a method for producing a silicon-containing polymer having an acetylene bond containing a repeating unit represented by the general formula (4).

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION The characteristics of the production method of the present invention can be summarized by referring to the reaction formula (5).

[0013]

Embedded image By reacting a silyl compound represented by R _4-m -SiH _m and an ethynyl compound represented by R ¹ -C≡CH in the presence of metal compounds, The point is that the silylacetylene compound represented by (1) can be produced.

Further, the reaction formula (6)

[0015]

Embedded image As shown in the formula, an acetylene bond containing a repeating unit represented by the general formula (3) is obtained by reacting a hydrosilyl compound represented by R ² —SiH ₂ —R ³ with acetylene in the presence of a metal compound. Is to produce a silicon-containing polymer having the following formula:

Further, the reaction formula (7) (Formula 11)

[0017]

Embedded image As shown in the formula, a hydrosilyl compound represented by R ² —SiH ₂ —R ³ is reacted with a diethynyl compound represented by the general formula (2) in the presence of a metal compound to obtain a compound represented by the general formula (4). A silicon-containing polymer having an acetylene bond containing a repeating unit represented by the formula:

The metal compounds usable in the reaction formulas (5), (6) and (7) are compounds in which a hydrocarbon atom, an alkoxy group, an amino group and the like are bonded to a metal atom. And a hydrogen atom or a halogen atom may be bonded to the metal. These metal compounds can be roughly classified into organometallic compounds, metal alkoxides and metal amides.

Examples of the organometallic compounds include an organic metal in which a hydrocarbon group such as an alkyl group, an alkynyl group, an alkenyl group, and an aryl group is bonded to one metal, and a composite organic metal in which two or more metals are bonded. Can be Examples of the metal element include group 1 typical elements such as lithium, sodium, potassium, rubidium and cesium; group 2 typical elements such as beryllium, magnesium, calcium, strontium and barium; group 13 typical elements such as boron and aluminum; and cadmium and zinc. Group 12 transition metal element.

An alkyl group bonded to these metal elements,
Alkynyl, alkenyl, hydrocarbon groups such as aryl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, cyclopentadienyl, hexyl, Cyclohexyl group, octyl group, vinyl group, allyl group, 1-
Propenyl, ethynyl, hexynyl, phenylethynyl, phenyl, naphthyl, benzyl, methylbenzyl, tolyl, mesityl, diphenylmethyl, triphenylmethyl, styryl, α-methylbenzyl, etc. Is mentioned. However, the valence of the metal is 2
In the above case or in the composite organic metal, in addition to these organic groups, a halogen group such as a fluoro group, a chloro group, a bromo group, an iodo group, a hydrogen atom, an alkoxy group such as a methoxy group or an ethoxy group, or an amino group is bonded. It may be.

Examples of the organometallic compounds in which a hydrocarbon group such as an alkyl group, an alkynyl, an alkenyl, and an aryl group is bonded to a metal include methyl lithium, ethyl lithium, propyl lithium, isopropyl lithium, and the like.
n-butyllithium, isobutyllithium, t-butyllithium, pentyllithium, hexyllithium, cyclohexyllithium, octyllithium, vinyllithium, allyllithium, 1-propenyllithium, ethynyllithium, 1-hexynyllithium, phenyllithium, naphthyllithium , Benzyllithium, methylbenzyllithium, tolyllithium, mesityllithium, diphenylmethyllithium, triphenylmethyllithium, styryllithium, α-methylbenzyllithium,
Phenylethynyl lithium, methyl sodium, ethyl sodium, propyl sodium, isopropyl sodium, n-butyl sodium, isobutyl sodium,
t-butyl sodium, pentyl sodium, cyclopentadienyl sodium, hexyl sodium, cyclohexyl sodium, octyl sodium, vinyl sodium, allyl sodium, 1-propenyl sodium, ethynyl sodium, 1-hexynyl sodium,
Phenyl sodium, naphthyl sodium, benzyl sodium, methyl benzyl sodium, tolyl sodium, mesityl sodium, diphenyl methyl sodium, triphenyl methyl sodium, styryl sodium, α-methyl benzyl sodium, phenylethynyl sodium, methyl potassium, ethyl potassium, propyl potassium Isopropyl potassium, n-butyl potassium, isobutyl potassium, t-butyl potassium, pentyl potassium, hexyl potassium, cyclohexyl potassium, octyl potassium, vinyl potassium, allyl potassium, 1-propenyl potassium, ethynyl potassium, 1-
Hexinyl potassium, phenyl potassium, naphthyl potassium, benzyl potassium, methyl benzyl potassium, tolyl potassium, mesityl potassium, diphenyl methyl potassium, triphenyl methyl potassium, styryl potassium, α-methyl benzyl potassium, phenylethynyl potassium, methyl rubidium, ethyl Rubidium, propyl rubidium, isopropyl rubidium, n-butyl rubidium, t-butyl rubidium, phenyl rubidium, methyl cesium, ethyl cesium, propyl cesium, isopropyl cesium, n-butyl cesium, t-
Butyl cesium, phenyl cesium, dimethyl beryllium, diethyl beryllium, dipropyl beryllium, di-n
-Butyl beryllium, di-t-butyl beryllium, dipentyl beryllium, dihexyl beryllium, diphenyl beryllium, methyl beryllium chloride, ethyl beryllium chloride, propyl beryllium chloride, n-
Butyl beryllium chloride, phenyl beryllium chloride, methyl beryllium bromide, ethyl beryllium bromide, propyl beryllium bromide, butyl beryllium bromide, phenyl beryllium bromide, methyl beryllium iodide, ethyl beryllium iodide, propyl beryllium iodide, n-
Butyl beryllium iodide, phenyl beryllium iodide, dimethyl magnesium, diethyl magnesium, dipropyl magnesium, di-n-butyl magnesium, di-t-butyl magnesium, dipentyl magnesium, dihexyl magnesium, diphenyl magnesium, methyl magnesium fluoride, ethyl magnesium fluoride , Propyl magnesium fluoride, n-butyl magnesium fluoride, hexyl magnesium fluoride, phenyl magnesium fluoride, methyl magnesium chloride, ethyl magnesium chloride, propyl magnesium chloride,
Butyl magnesium chloride, t-butyl magnesium chloride, pentyl magnesium chloride, hexyl magnesium chloride, phenyl magnesium chloride, methyl magnesium bromide, ethyl magnesium bromide, propyl magnesium bromide, butyl magnesium bromide, t-butyl magnesium bromide, pentyl magnesium bromide,
Hexyl magnesium bromide, phenyl magnesium bromide, methyl magnesium iodide, ethyl magnesium iodide, propyl magnesium iodide, n-butyl magnesium iodide, hexyl magnesium iodide, phenyl magnesium iodide, ethyl magnesium hydride, ethyl magnesium ethoxide, dimethyl Calcium, diethyl calcium, dipropyl calcium, di-n-butyl calcium, di-t-butyl calcium, dipentyl calcium, dihexyl calcium, diphenyl calcium, methyl calcium chloride, ethyl calcium chloride, propyl calcium chloride, n-butyl calcium chloride, phenyl calcium Chloride, methylcalcium Bromide, ethyl calcium bromide, propyl calcium bromide, n- butyl calcium bromide, phenyl calcium bromide, methyl calcium iodide, ethyl calcium iodide, propyl calcium iodide, n-
Butyl calcium iodide, phenyl calcium iodide, dimethyl strontium, diethyl strontium, dipropyl strontium, di n-butyl strontium, di-t-n-butyl strontium, dipentyl strontium, dihexyl strontium, diphenyl strontium dimethyl barium, diethyl barium, dipropyl Barium, di-n-butyl barium, di-t-n-butyl barium, dipentyl barium,
Dihexyl barium, diphenyl barium, diethynyl barium, di (1-hexynyl) barium, di (phenyl) barium, dinaphthyl barium, dibenzyl barium, ditolyl barium, dimesityl barium, bis (diphenylmethyl) barium, bis ( Triphenylmethyl) barium, styryl) barium, di (α-methylbenzyl) barium, di (phenylethynyl) barium,
Di (3-ethynylphenylethynyl) barium, di (4
-Ethynylphenylethynyl) barium, ethyl barium chloride, ethyl barium bromide, ethyl barium iodide, ethynyl barium hydride, phenyl ethynyl barium hydride, ethyl barium ethoxide, propyl barium propoxide, butyl barium butoxide, ethynyl barium ethoxide, phenyl ethynyl Barium propoxide, phenylethynyl barium butoxide, ethyl barium amide, phenyl barium amide, trimethyl borane, triethyl borane, tripropyl borane, tri-n-butyl borane, tri-n-butyl borane, tripentyl borane, trihexyl borane, triphenyl borane , Trimethylaluminum, triethylaluminum, tripropylaluminum, tri-n-butyl Aluminum, tri-t-n-butyl aluminum, tripentyl aluminum, tri-hexyl aluminum, triphenyl aluminum, chlorodimethyl aluminum, chloro diethylaluminum,
Chlorodipropylaluminum, chlorodi-n-butylaluminum, chlorodiphenylaluminum, bromodimethylaluminum, bromodiethylaluminum, bromodipropylaluminum, bromodin-butylaluminum, bromodiphenylaluminum, dimethylzinc, diethylzinc, dipropylzinc, din- Butyl zinc, dihexyl zinc, diphenyl zinc, dimethyl cadmium, diethyl cadmium, dipropyl cadmium, di-n-butyl cadmium, dihexyl cadmium, diphenyl cadmium and the like.

Among the organometallic compounds, the complex organic metal includes lithium tetraethylaluminum, lithium tetrapropylaluminum, lithium tetrahexynylaluminum, lithium tetra (phenylethynyl) aluminum, lithium tri (phenylethynyl)
Aluminum ethoxide, lithium di (phenylethynyl) aluminum diethoxide, sodium tetraethylaluminum, sodium tetrapropylaluminum, sodium tetrahexynylaluminum, sodium tetra (phenylethynyl) aluminum, lithium triethylzinc, lithium tripropylzinc, lithium tri (phenyl) (Ethynyl) zinc, sodium triethyl zinc, sodium tripropyl zinc, sodium tri (phenylethynyl) zinc, calcium tetraethyl zinc, calcium tetrapropyl zinc, strontium tetraethyl zinc, strontium tetrapropyl zinc, and the like.

The alkoxides are classified into a metal alkoxide compound in which the metal bonded to the alkoxy group is one kind and a heterometal alkoxide compound in which the metal is two kinds. Examples of the metal element to which the alkoxy group is bonded include group 1 typical elements such as lithium, sodium, potassium, rubidium and cesium, group 2 typical elements such as beryllium, magnesium, calcium, strontium and barium, and boron, aluminum, gallium and indium. 13
Group III transition metal elements such as Group III transition metal elements such as titanium and zirconium; Group V transition metal elements such as niobium; Group 6 transition metal elements such as chromium; and Group 7 transition metal elements such as manganese And a Group 8 transition metal element such as iron, a Group 9 transition metal element such as cobalt, a Group 10 transition metal element such as nickel, a Group 11 transition metal element such as copper, and a Group 12 transition metal element such as zinc.

The alkoxy groups bonded to these metal elements include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, t-
Butoxy, pentyloxy, hexyloxy, octyloxy, allyloxy, benzyloxy,
Phenoxy, naphthyloxy, methoxyethoxy, methoxyethoxyethoxy, methoxypropoxy and the like. However, when the valence of the metal is 2 or more or in a heterometal alkoxide compound, in addition to these alkoxy groups, alkyl groups, alkynyl groups, alkenyl groups, hydrocarbon groups such as aryl groups, fluoro groups,
A halogen group such as a chloro group, a bromo group and an iodo group, a hydrogen atom or an amino group may be bonded.

Examples of the metal alkoxide compound in which an alkoxy group is bonded to a group 1 typical metal element include lithium methoxide, lithium ethoxide, lithium propoxide, lithium isopropoxide, lithium-n-butoxide, and lithium isopropoxide. Butoxide, lithium-t-butoxide, lithium pentyl oxide, lithium hexyl oxide, lithium octyl oxide, lithium allyl oxide, lithium benzyl oxide, lithium phenoxide, lithium naphthyl oxide, lithium methoxy ethoxide, lithium methoxy ethoxy ethoxide,
Lithium methoxypropoxide, sodium methoxide, sodium ethoxide, sodium propoxide,
Sodium isopropoxide, sodium-n-butoxide, sodium isobutoxide, sodium-t-butoxide, sodium pentyl oxide, sodium hexyl oxide, sodium octyl oxide, sodium allyl oxide, sodium benzyl oxide, sodium phenoxide, sodium naphthyl oxide,
Sodium methoxy ethoxide, sodium methoxy ethoxy ethoxide, sodium methoxy propoxide,
Potassium methoxide, potassium ethoxide, potassium propoxide, potassium isopropoxide, potassium-n
-Butoxide, potassium isobutoxide, potassium-t
-Butoxide, potassium pentyl oxide, potassium hexyl oxide, potassium octyl oxide, potassium allyl oxide, potassium benzyl oxide, potassium phenoxide, potassium naphthyl oxide, potassium methoxy ethoxide, potassium methoxy ethoxy ethoxide, potassium methoxy propoxide, rubidium methoxide, Rubidium ethoxide, rubidium propoxide, rubidium isopropoxide, rubidium-n-butoxide, rubidium-t-butoxide, rubidium benzyl oxide, rubidium phenoxide, rubidium methoxy ethoxide, cesium methoxide, cesium ethoxide, cesium propoxide Isopropoxide, cesium-n-butoxide, cesium-t-butoxide, cesium Njiruokishido, cesium phenoxide, cesium methoxide ethoxide.

Specific examples of the metal alkoxide compound in which an alkoxy group is bonded to a group 2 typical metal element include beryllium di (methoxide), beryllium di (ethoxide), beryllium di (propoxide), and beryllium di (isopropoxide). ), Beryllium di (n-butoxide), beryllium di (isobutoxide), beryllium di (t-butoxide), beryllium di (pentyl oxide), beryllium di (hexyl oxide), beryllium di (octyl oxide), beryllium di (benzyl) Oxide), beryllium di (phenoxide), beryllium di (naphthyl oxide), beryllium di (methoxyethoxide), beryllium di (methoxyethoxyethoxide), beryllium di (methoxypropoxide), magnesium di (methoxide), magnesium Umdi (ethoxide), magnesium di (propoxide), magnesium di (isopropoxide), magnesium di (n-butoxide), magnesium di (isobutoxide), magnesium di (t-butoxide), magnesium di (pentyl oxide), Magnesium di (hexyl oxide), magnesium di (octyl oxide), magnesium di (benzyl oxide), magnesium di (phenoxide), magnesium di (methoxy ethoxide), magnesium di (methoxy ethoxy ethoxide), magnesium di (methoxy propoxide) ), Magnesium, calcium di (methoxide), calcium di (ethoxide),
Calcium di (propoxide), calcium di (isopropoxide), calcium di (n-butoxide), calcium di (isobutoxide), calcium di (t-butoxide), calcium di (pentyl oxide), calcium di (hexyl oxide) ), Calcium di (octyl oxide), calcium di (benzyl oxide), calcium di (phenoxide), calcium di (methoxy ethoxide), calcium di (methoxy ethoxy ethoxide), calcium di (methoxy propoxide), strontium di ( Methoxide), strontium di (ethoxide), strontium di (propoxide), strontium di (isopropoxide), strontium di (n
-Butoxide), strontium di (isobutoxide), strontium di (t-butoxide), strontium di (pentyl oxide), strontium di (hexyl oxide), strontium di (octyl oxide), strontium di (benzyl oxide), strontium di ( Phenoxide), strontium di (methoxy ethoxide), strontium di (methoxy ethoxy ethoxide), strontium di (methoxy propoxide), barium di (methoxide), barium di (ethoxide), barium di (propoxide), barium di (isopropoxide) , Barium di (n-butoxide), barium di (isobutoxide), barium di (s
-Butoxide), barium di (t-butoxide), barium di (pentyl oxide), barium di (hexyl oxide), barium di (octyl oxide), barium di (benzyl oxide), barium di (phenoxide), barium di (methoxy ethoxide), barium di (methoxy ethoxy) Ethoxy ethoxide), barium di (methoxypropoxide) and the like.

Examples of the metal alkoxide compound in which an alkoxy group is bonded to a group 13 typical metal element include boron tri (methoxide), boron tri (ethoxide), and boron tri (methoxide).
Boron tri (propoxide), boron tri (isopropoxide), boron tri (n-butoxide), boron tri (isobutoxide), boron tri (t-butoxide),
Boron tri (pentyl oxide), boron tri (hexyl oxide), boron tri (octyl oxide), boron tri (benzyl oxide), boron tri (phenoxide), boron tri (methoxy ethoxide), boron tri (methoxy ethoxy ethoxide), boron tri (methoxy propoxide) , Aluminum tri (methoxide),
Aluminum tri (ethoxide), aluminum tri (propoxide), aluminum tri (isopropoxide), aluminum tri (n-butoxide), aluminum tri (isobutoxide), aluminum tri (t-
Butoxide), aluminum tri (pentyl oxide), aluminum tri (hexyl oxide), aluminum tri (octyl oxide), aluminum tri (benzyl oxide), aluminum tri (phenoxide), aluminum tri (methoxy ethoxide), aluminum tri (methoxy ethoxy) Ethoxide), aluminum tri (methoxypropoxide), gallium tri (methoxide), gallium tri (ethoxide), gallium tri (propoxide), gallium tri (isopropoxide), gallium tri (n-butoxide), gallium tri ( Isobutoxide), gallium tri (t-butoxide), gallium tri (pentyl oxide), gallium tri (hexyl oxide), gallium tri (octyl oxide), gallium tri (ben Oxide), gallium tri (phenoxide), gallium tri (methoxy ethoxide), gallium tri (methoxyethoxy ethoxide), gallium tri (methoxypropoxide), indium tri (methoxide), indium tri (methoxide), indium tri (ethoxide) ), Indium tri (isopropoxide), indium tri (n-butoxide), indium tri (isobutoxide), indium tri (t-butoxide), indium tri (pentyl oxide), indium tri (hexyl oxide), indium tri (hexyl oxide) (Octyl oxide), indium tri (benzyl oxide), indium tri (phenoxide), indium tri (methoxy ethoxide), indium tri (methoxy ethoxy ethoxide), indium tri (Methoxy propoxide), and the like.

Specific examples of the metal alkoxide compound in which an alkoxy group is bonded to a Group 3 transition metal element include yttrium tri (ethoxide), yttrium tri (isopropoxide side), and yttrium tri (methoxyethoxide side). No.

Specific examples of the metal alkoxide compound in which an alkoxy group is bonded to a Group 4 transition metal element include titanium tetra (methoxide), titanium tetra (ethoxide), titanium tetra (propoxide) and titanium tetra (isopropoxide). ), Titanium tetra (methoxy ethoxide), zirconium tetra (methoxide), zirconium tetra (ethoxide), zirconium tetra (propoxide), zirconium tetra (isopropoxide), zirconium tetra (methoxy ethoxide), and the like.

Specific examples of the metal alkoxide compound in which an alkoxy group is bonded to a group V transition metal element include niobium penta (ethoxide). Specific examples of the metal alkoxide compound in which an alkoxy group is bonded to a Group 6 transition metal element include chromium tri (ethoxide),
Chromium tri (isopropoxide) and the like. Specific examples of the metal alkoxide compound in which an alkoxy group is bonded to a Group 7 transition metal element include manganese di (methoxide) and manganese di (ethoxide).
Specific examples of the metal alkoxide compound in which an alkoxy group is bonded to a Group 8 transition metal element include iron tri (ethoxide). Specific examples of the metal alkoxide compound in which an alkoxy group is bonded to a Group 9 transition metal element include cobalt di (methoxide) and cobalt di (ethoxide). Specific examples of the metal alkoxide compound in which an alkoxy group is bonded to a Group 10 transition metal element include nickel di (ethoxide) and nickel di (methoxide). Specific examples of the metal alkoxide compound in which an alkoxy group is bonded to a Group 11 transition metal element include copper di (methoxide), copper di (ethoxide), copper di (propoxide), copper di (isopropoxide), and copper di (isopropoxide). Di (n-butoxide), copper di (t-butoxide), copper di (methoxyethoxide) and the like.
Specific examples of the metal alkoxide compound in which an alkoxy group is bonded to a Group 12 transition metal element include zinc diethoxide and zinc di (methoxy ethoxide).

As the heterometal alkoxide compound,
Specifically, lithium aluminum tetramethoxide,
Lithium aluminum tetraethoxide, lithium aluminum tetrapropoxide, sodium aluminum tetrabutoxide, sodium aluminum tetramethoxide, sodium aluminum tetraethoxide, sodium aluminum tetrapropoxide, sodium aluminum tetrabutoxide, potassium aluminum tetramethoxide, potassium aluminum tetraethoxy And potassium aluminum tetrapropoxide, potassium aluminum tetrabutoxide and the like.

In the present invention, a metal amide is a metal amide compound in which one hydrogen atom of ammonia or a primary or secondary amine is substituted with a metal atom; two hydrogen atoms of ammonia or a primary amine are metal atoms. A substituted metal imide compound; and a metal nitride compound in which three hydrogen atoms of ammonia have been replaced by metal atoms.

Examples of the primary or secondary amine include methylamine, dimethylamine, ethylamine, ethylamine, propylamine, dipropylamine, isopropylamine, diisopropylamine, butylamine, dibutylamine, isobutylamine, diisobutylamine, t-butylamine, and dibutylamine. -T-butylamine, pentylamine,
Dipentylamine, hexylamine, dihexylamine, octylamine, allylamine, diallylamine,
Examples include trimethylsilylamine, bis (trimethylsilyl) amine, aniline, diphenylamine and the like.

The metal elements to be substituted include Group 1 typical elements such as lithium, sodium, potassium, rubidium and cesium and Group 2 typical elements such as beryllium, magnesium, calcium, strontium and barium. However, when the valence of the metal is 2 or more, these metal atoms may be a hydrogen atom or a halogen group such as a fluoro group, a chloro group, a bromo group, an iodo group, an alkyl group, an alkynyl group, an alkenyl group, an aryl group, or the like. Hydrocarbon groups,
An alkoxy group such as a methoxy group or an ethoxy group may be bonded.

The metal amide compound in which the metal atom replacing the hydrogen atom is a group 1 typical metal element includes, specifically,
Lithium amide, lithium methylamide, lithium dimethylamide, lithium ethylamide, lithium diethylamide, lithium propylamide, lithium dipropylamide, lithium isopropylamide, lithium diisopropylamide, lithium butylamide, lithium dibutylamide, lithium isobutylamide, lithium diisobutylamide , Lithium-t-butylamide, lithium di-t-butylamide, lithium pentylamide, lithium dipentylamide, lithium hexylamide, lithium dihexylamide, lithium octylamide, lithium allylamide, lithium diallylamide, lithium trimethylsilylamide, lithium bis (trimethylsilyl) Amide, lithium phenylamide, lithium diphenylamide, Thorium amide, sodium methylamide, sodium dimethylamide, sodium ethylamide, sodium diethylamide, sodium propyl amide, sodium dipropylamide, sodium diisopropylamide, sodium diisopropylamide,
Sodium butylamide, sodium dibutylamide,
Sodium isobutylamide, sodium diisobutylamide, sodium t-butylamide, sodium di-t-butylamide, sodium pentylamide, sodium dipentylamide, sodium hexylamide,
Sodium dihexylamide, sodium octylamide, sodium allylamide, sodium diallylamide, sodium trimethylsilylamide, sodium bis (trimethylsilyl) amide, sodium phenylamide, sodium diphenylamide, potassium amide,
Potassium methylamide, potassium dimethylamide, potassium ethylamide, potassium diethylamide, potassium propylamide, potassium dipropylamide, potassium isopropylamide, potassium diisopropylamide,
Potassium butylamide, potassium dibutylamide, potassium isobutylamide, potassium diisobutylamide,
Potassium-t-butylamide, potassium di-t-butylamide, potassium pentylamide, potassium dipentylamide, potassium hexylamide, potassium dihexylamide, potassium octylamide, potassium allylamide, potassium diallylamide, potassium trimethylsilylamide, potassium bis (trimethylsilyl) amide ,
Potassium phenylamide, potassium diphenylamide,
Rubidium amide, rubidium methylamide, rubidium dimethylamide, rubidium ethylamide, rubidium diethylamide, rubidium propylamide, rubidium dipropylamide, rubidium isopropylamide, rubidium diisopropylamide, rubidium butylamide, rubidium dibutylamide, rubidium isobutylamide, rubidium diisobutylamide , Rubidium di-t-butylamide, rubidium dipentylamide, rubidium dihexylamide, rubidium octylamide, rubidium trimethylsilylamide, rubidium bis (trimethylsilyl) amide, cesium amide,
Cesium methylamide, cesium dimethylamide, cesium ethylamide, cesium diethylamide, cesium propylamide, cesium dipropylamide, cesium isopropylamide, cesium diisopropylamide,
Cesium butylamide, cesium dibutylamide, cesium isobutylamide, cesium diisobutylamide,
Cesium di-t-butylamide, cesium dipentylamide, cesium dihexylamide, cesium octylamide, cesium trimethylsilylamide, cesium bis (trimethylsilyl) amide, and the like.

Examples of the metal amide compound in which the metal atom replacing the hydrogen atom is a Group 2 typical metal element include:
Beryllium diamide, beryllium bis (methylamide), beryllium bis (dimethylamide), beryllium bis (ethylamide), beryllium bis (diethylamide), beryllium bis (propylamide), beryllium bis (dipropylamide), beryllium bis (isopropylamide), Beryllium bis (diisopropylamide), beryllium bis (butylamide), beryllium bis (dibutylamide), beryllium bis (isobutylamide), beryllium bis (diisobutylamide), beryllium bis (t-butylamide), beryllium bis (di-t-butylamide) ), Beryllium bis (pentylamide), beryllium bis (dipentylamide), beryllium bis (hexylamide), beryllium bis (dihexylamide), beryllium (Octylamide), beryllium bis (allylamide), beryllium bis (diallylamide), beryllium bis (trimethylsilylamide), beryllium bis (bis (trimethylsilyl) amide), beryllium bis (phenylamide), beryllium bis (diphenylamide), Magnesium diamide, magnesium bis (methylamide), magnesium bis (dimethylamide), magnesium bis (ethylamide), magnesium bis (diethylamide), magnesium bis (propylamide), magnesium bis (dipropylamide), magnesium bis (isopropylamide), Magnesium bis (diisopropylamide), magnesium bis (butylamide), magnesium bis (dibutylamide), magnesium bis (isobutylamide) Amide), magnesium bis (diisobutylamide), magnesium bis (t-butylamide), magnesium bis (di-t-butylamide), magnesium bis (pentylamide), magnesium bis (dipentylamide), magnesium bis (hexylamide), magnesium Bis (dihexylamide), magnesium bis (octylamide), magnesium bis (allylamide),
Magnesium bis (diallylamide), magnesium bis (trimethylsilylamide), magnesium bis (bis (trimethylsilyl) amide), magnesium bis (phenylamide), magnesium bis (diphenylamide), calcium diamide, calcium bis (methylamide), calcium bis ( Dimethylamide), calcium bis (ethylamide), calcium bis (diethylamide), calcium bis (propylamide), calcium bis (dipropylamide), calcium bis (isopropylamide), calcium bis (diisopropylamide), calcium bis (butylamide) , Calcium bis (dibutylamide), calcium bis (isobutylamide), calcium bis (diisobutylamide), calcium bis (t- Chiruamido), calcium bis (di -t- butylamide), calcium bis (pentylamide), calcium bis (dipentyl amide), calcium bis (hexyl amide), calcium bis (dihexyl amide), calcium bis (octyl amide),
Calcium bis (allylamide), calcium bis (diallylamide), calcium bis (trimethylsilylamide), calcium bis (bis (trimethylsilyl) amide), calcium bis (phenylamide), calcium bis (diphenylamide), strontium diamide, strontium bis ( Methylamide), strontium bis (dimethylamide), strontium bis (ethylamide), strontium bis (diethylamide), strontium bis (propylamide), strontium bis (dipropylamide), strontium bis (isopropylamide), strontium bis (diisopropylamide) Strontium bis (butylamide), strontium bis (dibutylamide), strontium bis (isobutyl) Amide), strontium bis (diisobutyl amide), strontium bis (t-
Butylamide), strontium bis (di-t-butylamide), strontium bis (pentylamide), strontium bis (dipentylamide), strontium bis (hexylamide), strontium bis (dihexylamide), strontium bis (octylamide), strontium bis (Allylamide), strontium bis (diallylamide), strontium bis (trimethylsilylamide), strontium bis (bis (trimethylsilyl) amide), strontium bis (phenylamide), strontium bis (diphenylamide), barium diamide, barium bis (methylamide) , Barium bis (dimethylamide), barium bis (ethylamide), barium bis (diethylamide), barium bis (pro Barium bis (dipropylamide), barium bis (isopropylamide), barium bis (diisopropylamide), barium bis (butylamide), barium bis (dibutylamide), barium bis (isobutylamide), barium bis (diisobutylamide) ), Barium bis (t-butylamide), barium bis (di-t-butylamide),
Barium bis (pentylamide), barium bis (dipentylamide), barium bis (hexylamide), barium bis (dihexylamide), barium bis (octylamide), barium bis (allylamide), barium bis (diallylamide), barium bis (Trimethylsilylamide), barium bis (bis (trimethylsilyl) amide), barium bis (phenylamide), barium bis (diphenylamide), barium (hydro) amide, and barium (hydro) dimethylamide.

As the metal imide compound in which the metal atom replacing the hydrogen atom is a Group 1 typical metal element, specifically,
Lithium imide, lithium methyl imide, lithium ethyl imide, lithium propyl imide, lithium isopropyl imide, lithium butyl imide, lithium isobutyl imide, lithium tert-butyl imide, lithium pentyl imide, lithium hexyl imide, lithium octyl imide, lithium allyl imide, lithium Trimethylsilyl imide, lithium phenyl imide, sodium imide, sodium methyl imide, sodium ethyl imide, sodium propyl imide, sodium isopropyl imide, sodium butyl imide, sodium isobutyl imide, sodium tert-butyl imide, sodium pentyl imide, sodium hexyl imide, sodium octyl Imide, sodium allyl imide, sodium trimethyl Imide, sodium phenylimide, potassium imide, potassium methyl imide, potassium ethyl imide, potassium propyl imide, potassium isopropyl imide, potassium butyl imide, potassium isobutyl imide, potassium-t-butyl imide, potassium pentyl imide, potassium hexyl imide, potassium octyl imide , Potassium allyl imide, potassium trimethylsilyl imide, potassium phenyl imide, rubidium imide, rubidium methyl imide, rubidium ethyl imide, rubidium propyl imide, rubidium isopropyl imide, rubidium butyl imide, rubidium isobutyl imide, rubidium-t-butyl imide, rubidium trimethyl silyl imide, Cesium imide, cesium methyl imide, cesium ethyl Bromide, cesium propyl imide, cesium isopropyl imide, cesium butyl imido, cesium isobutyl imide, cesium -
t-butyl imide, cesium trimethylsilyl imide and the like.

Examples of the metal imide compound in which the metal atom replacing the hydrogen atom is a Group 2 typical metal element include:
Beryllium imide, beryllium methyl imide, beryllium ethyl imide, beryllium propyl imide, beryllium isopropyl imide, beryllium butyl imide, beryllium isobutyl imide, beryllium-t-butyl imide, beryllium pentyl imide, beryllium hexyl imide, beryllium octyl imide, beryllium allyl imide, beryllium Trimethylsilyl imide, beryllium phenyl imide, magnesium imide, magnesium methyl imide, magnesium ethyl imide, magnesium propyl imide, magnesium isopropyl imide, magnesium butyl imide, magnesium isobutyl imide, magnesium tert-butyl imide, magnesium pentyl imide, magnesium hexyl imide, magnesium octyl Imi , Magnesium allyl imide, magnesium trimethylsilyl imide, magnesium phenyl imide, calcium imide, calcium methyl imide, calcium ethyl imide, calcium propyl imide, calcium isopropyl imide, calcium butyl imide, calcium isobutyl imide, calcium -t
-Butyl imide, calcium pentyl imide, calcium hexyl imide, calcium octyl imide, calcium allyl imide, calcium trimethyl silyl imide,
Calcium phenyl imide, strontium imide, strontium methyl imide, strontium dimethyl imide, strontium ethyl imide, strontium propyl imide, strontium isopropyl imide, strontium butyl imide, strontium isobutyl imide, strontium-t-butyl imide, strontium pentyl imide, strontium hexyl imide, strontium Octylimide, strontium allylimide, strontium trimethylsilylimide,
Strontium phenyl imide, barium imide, barium methyl imide, barium ethyl imide, barium propyl imide, barium isopropyl imide, barium butyl imide, barium isobutyl imide, barium-
t-butyl imide, barium pentyl imide, barium hexyl imide, barium octyl imide, barium allyl imide, barium trimethylsilyl imide, barium phenyl imide and the like.

Examples of the metal nitride compound include lithium nitride, sodium nitride, potassium nitride, rubidium nitride, cesium nitride, beryllium nitride, magnesium nitride, calcium nitride, strontium nitride, barium nitride and the like. Can be These metal compounds can be used alone or in combination of two or more.

By subjecting a silyl compound represented by R _4-m -SiH _m and an ethynyl compound represented by R ¹ -C 脱 CH to a dehydrogenation reaction in the presence of a metal compound, a compound represented by the general formula (1) is obtained. A method for producing the represented silylacetylene compound will be described. Specific examples of the silyl compound represented by the raw material R _4-m -SiH _m include silane, methylsilane, dimethylsilane, trimethylsilane, ethylsilane, diethylsilane, triethylsilane, phenylsilane, diphenylsilane, triphenylsilane, Hexylsilane,
Vinylsilane, allylsilane, ethynylsilane, 2-propynylsilane, benzoylsilane, trifluoromethylsilane, (3,3,3-trifluoropropyl) silane, 4-silyltoluene, 4-silylstyrene, 4-silyl-α, α , Α-trifluorotoluene, methoxysilane, dimethoxysilane, trimethoxysilane, ethoxysilane, diethoxysilane, triethoxysilane and the like.

Examples of the raw material ethynyl compound represented by R ¹ —C≡CH include acetylene, propyne, 1-butyne, 1-hexyne, vinyl acetylene,
Examples include diacetylene, phenylacetylene, ethynylcyclohexane, 4-ethynyltoluene, 4-ethynylaniline, and 3-ethynylaniline.

Specific examples of the silylacetylene compound represented by the general formula (1) obtained in the present invention include silylacetylene, diethynylsilane, methylsilylacetylene, dimethylsilylacetylene, trimethylsilylacetylene, ethylsilylacetylene, diethyl Silyl acetylene, triethyl silyl acetylene, phenyl silyl acetylene, diphenyl silyl acetylene, triphenyl silyl acetylene, hexyl silyl acetylene, vinyl (ethynyl) silane, allyl (ethynyl) silane, diethynyl silane, 2-propynyl (ethynyl) silane,
Benzoyl (ethynyl) silane, trifluoromethyl (ethynyl) silane, (3,3,3-trifluoropropyl) (ethynyl) silane, 4- (ethynylsilyl) toluene, 4- (ethynylsilyl) styrene, 4- (ethynyl) Silyl) -α, α, α-trifluorotoluene, methoxysilylacetylene, dimethoxysilylacetylene,
Trimethoxysilylacetylene, ethoxysilylacetylene, diethoxysilylacetylene, triethoxysilylacetylene, 1-silyl-1-propyne, bis (1-
Propynyl) silane, methylsilyl-1-propyne, dimethylsilyl-1-propyne, trimethylsilyl-1-
Propyne, ethylsilyl-1-propyne, diethylsilyl-1-propyne, triethylsilyl-1-propyne,
Phenylsilyl-1-propyne, diphenylsilyl-1
-Propyne, triphenylsilyl-1-propyne, hexylsilyl-1-propyne, 1-silyl-1-butyne,
Bis (1-butynyl) silane, tri (1-butynyl) silane, methylsilyl-1-butyne, dimethylsilyl-1
-Butyne, trimethylsilyl-1-butyne, ethylsilyl-1-butyne, diethylsilyl-1-butyne, triethylsilyl-1-butyne, phenylsilyl-1-butyne, diphenylsilyl-1-butyne, triphenylsilyl-1-butyne Hexylsilyl-1-butyne, 1-silyl-1-hexyne, bis (1-hexenyl) silane,
Tri (1-hexenyl) silane, methylsilyl-1-hexyne, dimethylsilyl-1-hexyne, trimethylsilyl-1-hexyne, ethylsilyl-1-hexyne, diethylsilyl-1-hexyne, triethylsilyl-1-
Hexine, phenylsilyl-1-hexine, diphenylsilyl-1-hexyne, triphenylsilyl-1-hexyne, hexylsilyl-1-hexyne, vinylethynylsilane, methylsilyl-2-buten-1-yne, dimethylsilyl-2- Buten-1-yne, trimethylsilyl-
2-buten-1-yne, ethylsilyl-2-butene-1
-In, diethylsilyl-2-buten-1-yne, triethylsilyl-2-buten-1-yne, phenylsilyl-2-buten-1-yne, diphenylsilyl-2-buten-1-yne, triphenylsilyl -2-butene-1-
In, hexylsilyl-2-buten-1-yne, 1-silyl-1,3-butadiyne, methylsilyl-1,3-butadiyne, dimethylsilyl-1,3-butadiyne, trimethylsilyl-1,3-butadiyne, ethylsilyl- 1,3
-Butadiyne, diethylsilyl-1,3-butadiyne,
Triethylsilyl-1,3-butadiyne, phenylsilyl-1,3-butadiyne, diphenylsilyl-1,3-butadiyne, triphenylsilyl-1,3-butadiyne,
Hexylsilyl-1,3-butadiyne, phenylethynylsilane, bis (phenylethynyl) silane, tri (phenylethynyl) silane, tetra (phenylethynyl)
Silane, methylsilyl (phenyl) acetylene, bis (phenylethynyl) methylsilane, tri (phenylethynyl) methylsilane, dimethylsilyl (phenyl) acetylene, bis (phenylethynyl) dimethylsilane,
Trimethylsilyl (phenyl) acetylene, ethylsilyl (phenyl) acetylene, bis (phenylethynyl)
Ethylsilane, tri (phenylethynyl) ethylsilane, diethylsilyl (phenyl) acetylene, bis (phenylethynyl) diethylsilane, triethylsilyl (phenyl) acetylene, phenylsilyl (phenyl)
Acetylene, bis (phenylethynyl) phenylsilane, tri (phenylethynyl) phenylsilane, diphenylsilyl (phenyl) acetylene, bis (phenylethynyl) diphenylsilane, triphenylsilyl (phenyl) acetylene, hexylsilyl (phenyl) acetylene, bis ( Phenylethynyl) hexylsilane, tri (phenylethynyl) hexylsilane, vinyl (phenylethynyl) silane, allyl (phenylethynyl) silane, phenylethynyl (ethynyl) silane, 2-propynyl (phenylethynyl) silane, benzoyl (phenylethynyl) silane , Trifluoromethyl (phenylethynyl) silane, (3,3,3-trifluoropropyl)
(Phenylethynyl) silane, 4- (phenylethynylsilyl) toluene, 4- (phenylethynylsilyl) styrene, 4- (phenylethynylsilyl) -α, α, α
-Trifluorotoluene, methoxysilyl (phenyl)
Acetylene, dimethoxysilyl (phenyl) acetylene, trimethoxysilyl (phenyl) acetylene, ethoxysilyl (phenyl) acetylene, diethoxysilyl (phenyl) acetylene, triethoxysilyl (phenyl) acetylene, silylene, 3-silylethynylaniline, bis ( 3-aminophenylethynyl) silane 3-
(Methylsilylethynyl) aniline, 3- (dimethylsilylethynyl) aniline, 3- (trimethylsilylethynyl) aniline, 3- (phenylsilylethynyl) aniline, bis (3-aminophenylethynyl) (phenyl) silane, 3- (diphenyl) And silylethynyl) aniline, bis (3-aminophenylethynyl) diphenylsilane, 3- (triphenylsilylethynyl) aniline and the like.

The reactor comprises a part for supplying the raw materials, a stirring device inside the reactor, a part for controlling the temperature of the reactor, and the like. This reaction can be carried out without a solvent or in a solvent. Into the vessel are charged a raw material silyl compound represented by R _4-m -SiH _m , an ethynyl compound represented by R ¹ -C≡CH, metal compounds serving as a catalyst, and, if necessary, a solvent. The metal compounds can be charged in a solution or as it is without being dissolved in a solvent. The order of charging these containers is not particularly limited. The reaction solution is allowed to react for a predetermined time while being stirred while being controlled at a predetermined temperature. After a predetermined reaction time, the product is separated and purified from the reaction solution by a method such as distillation or column separation.

The ratio of the raw materials of the silyl compound represented by R _4-m -SiH _m and the ethynyl compound represented by R ¹ -C≡CH is not particularly limited. On the other hand, from lmmol to 10
000 mmol. The metal compounds as catalysts can be used alone or in combination of two or more.
The amount of the catalyst used is from 0.0001 mmol to 200 mmol per 100 mmol of the ethynyl compound represented by R ¹ -C≡CH.
mmol.

When the raw material silyl compound represented by R _4-m -SiH _m or the ethynyl compound represented by R ¹ -C≡CH is a gas, it may be used as such, or may be made of high-purity nitrogen, high-purity helium, or high-purity. After mixing with an inert gas such as argon,
It is desirable that the reaction be performed by press-fitting into a pressure-resistant container at a pressure of 1 to 250 kg / cm ² G. When both the silyl compound and the ethynyl compound as the raw materials are liquid or solid, it is desirable to replace the inside of the reaction vessel with an inert gas such as high-purity nitrogen or high-purity helium or high-purity argon. When the boiling point of the silyl compound or ethynyl compound is lower than the reaction temperature, the reaction pressure is reduced to 1 to 2 by injecting an inert gas or the like.
It is preferable that the pressure is increased to 50 kg / cm ² G and the boiling point of the raw material is set to the reaction temperature or higher. Examples of the solvent include saturated aliphatic hydrocarbon solvents such as pentane, hexane, heptane, and octane; aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and mesitylene; diethyl ether, n-butyl ether, and anisole. , Diphenyl ether, tetrahydrofuran, dioxane,
Ether solvents such as bis (2-methoxyethyl) ether and 1,2-bis (2-methoxyethoxy) ethane, halogen-containing solvents such as dichloromethane and chloroform, N-methylpyrrolidone, dimethylformamide, dimethylacetamide Or a mixed solvent thereof. The amount of the solvent depends on the R ¹ −
The amount is preferably 0.1 to 40 ml per 1 mmol of the ethynyl compound represented by C≡CH. Further, since water contained in the solvent may reduce the activity of the catalyst, it is preferable to use a solvent which has been previously dehydrated and dried.

The reaction temperature is from 0 to 300 ° C, more preferably from 20 to 150 ° C. The reaction pressure may be either normal pressure or pressurization. However, when the raw material is at normal pressure and the gas or the reaction temperature is higher than the boiling point of the raw material at normal pressure, pressurization is performed using a pressure-resistant reaction vessel (0 to 0). 250 kg / cm ² · G)
It is desirable that the raw material at the reaction temperature be liquid. The reaction time varies depending on the reaction temperature, etc.
~ 200 hours is appropriate.

The purification of the product may be carried out without any treatment of the reaction solution, but is preferably carried out after dispersing the reaction solution in water to decompose and separate the catalyst. The water for decomposing and separating the catalyst may be acidic or neutral, but may be HF, HCl, HBr, HI, H ₂ S
O ₄ , HNO ₃ , H ₂ CO ₃ , H ₃ PO ₄ , HClO ₂ , H
Inorganic acids such as ₂ S, H ₂ SO ₃ , H ₂ S ₂ O ₃ or HCOO
It is preferable to use an organic acid such as H, CH ₃ COOH, C ₆ H ₅ COOH, oxalic acid or the like to make it acidic to pH 0 to pH ₅ . The amount of water is 0.4 ml to 400 per 1 mmol of the catalyst.
ml. No solvent or water solubility 5wt%
When the above reaction solvent is used, an aromatic hydrocarbon solvent such as benzene, toluene and xylene, which has been dehydrated and dried before being dispersed, is used in an amount of 0.1 ml per 1 mmol of the raw material ethynyl compound represented by R ¹ -C≡CH. It is preferable to add ４０40 ml.

Next, a hydrosilyl compound represented by R ² —SiH ₂ —R ³ is reacted with acetylene or a diethynyl compound represented by the general formula (2) in the presence of a metal compound to form a compound represented by the general formula (3). The method for producing a silicon-containing polymer having an acetylene bond containing a repeating unit represented by the formula (1) will be described. R ² —SiH ₂ in the present invention
Silane as a hydrosilyl compound represented by -R ^3,
Methylsilane, dimethylsilane, ethylsilane, diethylsilane, phenylsilane, diphenylsilane, hexylsilane, vinylsilane, allylsilane, ethynylsilane, 1-silyl-2-propyne, benzoylsilane, trifluoromethylsilane, 1-silyl-3,3, 3-trifluoropropane, 4-silyltoluene, 4-silylstyrene, 4-silylethynyltoluene, 4-silyl-
α, α, α-trifluorotoluene, methoxysilane,
Examples include dimethoxysilane silane, ethoxysilane, diethoxysilane, and the like.

As the diethynyl compound represented by the general formula (2) used in the present invention, specifically, diacetylene,
m-diethynylbenzene, p-diethynylbenzene, o
-Diethynylbenzene, 3,5-diethynyltoluene,
2,7-diethynylnaphthalene, 5,10-diethynylanthracene, 4,4′-diethynylbiphenyl, bis (4
-Ethynylphenyl) methane, 2,2-bis (p-ethynylphenyl) propane, 2,2-bis (p-ethynylphenyl) trifluoropropane, bis (4-ethynylphenyl) ether, 2,2-bis (p -Ethynylphenyl) sulfone, 2,6-diethynylpyridine, 2,5
-Diethynylthiophene, chemical formula (8)

[0050]

Embedded image , Chemical formula (9)

[0051]

Embedded image , Chemical formula (10)

[0052]

Embedded image , Chemical formula (11)

[0053]

Embedded image , Chemical formula (12)

[0054]

Embedded image Etc.

Specifically, the silicon-containing polymer having an acetylene bond obtained by the present invention has a repeating unit represented by the following chemical formula (13).

[0056]

Embedded image , Chemical formula (14)

[0057]

Embedded image , Chemical formula (15)

[0058]

Embedded image , Chemical formula (16)

[0059]

Embedded image , Chemical formula (17)

[0060]

Embedded image , Chemical formula (18)

[0061]

Embedded image , Silyleneethynylene-1,3-phenyleneethynylene (chemical formula (19))

[0062]

Embedded image , Silyleneethynylene-1,4-phenyleneethynylene,
Silyleneethynylene-1,2-phenyleneethynylene, phenylsilyleneethynylene-1,3-phenyleneethynylene (chemical formula (20))

[0063]

Embedded image Phenylsilyleneethynylene-1,4-phenyleneethynylene, phenylsilyleneethynylene-1,2-phenyleneethynylene, methylsilyleneethynylene-1,3-phenyleneethynylene (chemical formula (21))

[0064]

Embedded image Diphenylsilyleneethynylene-1,3-phenyleneethynylene, methylsilyleneethynylene-1,4-phenyleneethynylene, methylsilyleneethynylene-1,2-phenyleneethynylene, chemical formula (22)

[0065]

Embedded image Dimethylsilyleneethynylene-1,3-phenyleneethynylene, chemical formula (23)

[0066]

Embedded image , Chemical formula (24)

[0067]

Embedded image , Chemical formula (25)

[0068]

Embedded image , Chemical formula (26)

[0069]

Embedded image , Chemical formula (27)

[0070]

Embedded image , Chemical formula (28)

[0071]

Embedded image , Chemical formula (29)

[0072]

Embedded image , Chemical formula (30)

[0073]

Embedded image , Chemical formula (31)

[0074]

Embedded image , Chemical formula (32)

[0075]

Embedded image , Chemical formula (33)

[0076]

Embedded image , Chemical formula (34)

[0077]

Embedded image , Chemical formula (35)

[0078]

Embedded image , Chemical formula (36)

[0079]

Embedded image , Chemical formula (37) (Formula 41)

[0080]

Embedded image , Chemical formula (38)

[0081]

Embedded image , Chemical formula (39)

[0082]

Embedded image , Chemical formula (40)

[0083]

Embedded image , Chemical formula (41)

[0084]

Embedded image , Chemical formula (42)

[0085]

Embedded image , Chemical formula (43)

[0086]

Embedded image , Chemical formula (44)

[0087]

Embedded image , Chemical formula (45)

[0088]

Embedded image , Chemical formula (46)

[0089]

Embedded image , Chemical formula (47)

[0090]

Embedded image , Chemical formula (48)

[0091]

Embedded image , Chemical formula (49)

[0092]

Embedded image , Chemical formula (50)

[0093]

Embedded image , Chemical formula (51)

[0094]

Embedded image And so on.

The reactor comprises a part for supplying raw materials, a stirring device inside the reactor, a part for controlling the temperature of the reactor, and the like. This reaction can be carried out without a solvent or in a solvent. Into the vessel are charged raw materials of a hydrosilyl compound represented by R ² —SiH ₂ —R ³ and acetylene or a diethynyl compound represented by the general formula (2), a metal compound as a catalyst, and, if necessary, a solvent. The metal compounds can be charged in a solution state or as it is. The order of charging these containers is not particularly limited. The reaction solution is allowed to react for a predetermined time while being stirred while being controlled at a predetermined temperature. After a predetermined reaction time, by removing the raw materials and the solvent by distillation, by column separation or by dispersing the reaction solution in a poor solvent for the polymer,
The polymer is separated and purified from the reaction solution.

The ratio of the starting material hydrosilyl compound represented by R ² —SiH ₂ —R ³ to acetylene or the diethynyl compound represented by the general formula (2) is not particularly limited, but is preferably based on 100 mmol of the diethynyl compound. It is from 10 mmol to 1000 mmol. The metal compounds as catalysts can be used alone or in combination of two or more. The amount of the catalyst used is 0.0001 mmol per 100 mmol of the acetylene or diethynyl compound.
1 to 200 mmol.

When the raw material acetylene, the hydrosilyl compound represented by R ² —SiH ₂ —R ³ , or the diethynyl compound represented by the general formula (2) is a gas, it may be used as it is, or may be made of high-purity nitrogen, high-purity helium, After mixing with an inert gas such as high-purity argon, 1 to 250 kg / cm ²
It is desirable that the reaction be performed by press-fitting the mixture into a pressure vessel at a pressure of G. When the raw material hydrosilyl compound and diethynyl compound are both liquid or solid, it is desirable to replace the inside of the reaction vessel with an inert gas such as high-purity nitrogen or high-purity helium or high-purity argon. Examples of the solvent include aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and mesitylene; diethyl ether, n-butyl ether, anisole, diphenyl ether, tetrahydrofuran, dioxane, bis (2-methoxyethyl) ether, Ether solvents such as 2-bis (2-methoxyethoxy) ethane, halogen-containing solvents such as dichloromethane and chloroform, and N-
Organic polar solvents such as methylpyrrolidone, dimethylformamide, dimethylacetamide, and mixed solvents thereof can be used. The amount of the solvent is 1 m of the starting diethynyl compound.
0.1-40 ml is preferable with respect to mol. Further, since water contained in the solvent may reduce the activity of the catalyst, it is preferable to use a solvent which has been previously dehydrated and dried.

The reaction temperature is from 0 to 300 ° C., more preferably
20-150 ° C. Reaction pressure is normal pressure or pressurized
However, it does not matter if the raw material is gas or the reaction temperature is
If the temperature is higher than the boiling point of the solvent, use a pressure-resistant reaction vessel.
Pressurization (0-250kg / cm ^Two・ G) Performing the reaction
desirable. The reaction time varies depending on the reaction temperature and the like.
1 to 200 hours is appropriate.

The purification of the product may be carried out without any treatment of the reaction solution, but is preferably carried out after dispersing the reaction solution in water to decompose and separate the catalyst. The water for decomposing and separating the catalyst may be acidic or neutral, but may be HF, HCl, HBr, HI, H ₂ S
O ₄ , HNO ₃ , H ₂ CO ₃ , H ₃ PO ₄ , HClO ₂ , H
Inorganic acids such as ₂ S, H ₂ SO ₃ , H ₂ S ₂ O ₃ or HCOO
It is preferable to use an organic acid such as H, CH ₃ COOH, C ₆ H ₅ COOH, oxalic acid or the like to make it acidic to pH 0 to pH ₅ . The amount of water is 0.4 ml to 400 per 1 mmol of the catalyst.
ml. No solvent or water solubility 5wt%
In the case where the above reaction solvent is used, an aromatic hydrocarbon solvent such as benzene, toluene, or xylene, which has been dehydrated and dried before dispersion, is used in an amount of 0.1 ml to 1 mmol of the starting material for the diethynyl compound represented by the general formula (2). It is preferable to add 40 ml.

The poor solvent which can be used for separating and separating the polymer includes aliphatic hydrocarbons such as pentane, hexane, heptane and octane, and aliphatic alcohols such as methanol, ethanol and propanol. The amount of the poor solvent used is 1 m of acetylene or diethynyl compound as raw material.
The amount is 0.01 to 200 ml, more preferably 0.1 to 50 ml, per mol.

[0101]

The present invention will be described below with reference to examples and comparative examples. Example 1 A magnetic stirrer was installed inside a 100 ml glass container, and the inside of the container was replaced with high-purity nitrogen gas. Subsequently, 5.8 g (54 mmol) of phenylsilane as a raw material, 5.3 g (52 mmol) of phenylacetylene, 10 ml of bis (2-methoxyethyl) ether as a solvent, and n as a catalyst were placed in a container.
0.103 g of -butyllithium hexane solution (corresponding to 0.32 mmol of n-butyllithium) was charged, and the mixture was stirred at 80 ° C for 20 hours. After the reaction, the reaction solution was analyzed by GC (gas chromatography). Phenylethynyl (phenyl) silane (44% yield) and bis (phenylethynyl) (phenyl) silane (9% yield) as products
was gotten. The reaction rates were phenylsilane 62% and phenylacetylene 77%. The results show that silylacetylene compounds can be easily produced by using metal compounds as catalysts.

Examples 2 to 6 The metal compounds shown in Table 1 were used as catalysts, and the reaction was carried out for 8 hours under the same conditions as in Example 1. Table 1 shows the results.

Examples 7 to 20 The metal compounds shown in Table 2 were used as catalysts, and the reaction was carried out in the same manner as in Example 1 except for the other conditions. Table 2 shows the results
Shown in

Example 21 As a catalyst, 0.30 ml of a 1.04 mol / l hexane solution of lithium bis (trimethylsilyl) amide (0.3
The reaction was carried out in the same manner as in Example 1 except for using 1 mmol). Stirring was performed at 80 ° C. for 8 hours. As products, phenylethynyl (phenyl) silane (yield 40% based on the charged amount of phenylsilane) and bis (phenylethynyl) (phenyl) silane (yield 13% based on the charged amount of phenylsilane) were obtained. The reaction rates were phenylsilane 53% and phenylacetylene 70%.

Example 22 0.37 ml of a 1.0 mol / l THF solution of sodium bis (trimethylsilyl) amide as a catalyst (0.37 m
mol) and stirring was carried out at 80 ° C. for 2 hours under the same conditions as in Example 1. Phenylethynyl (phenyl) silane (yield 3 based on phenylsilane charge)
9%) and bis (phenylethynyl) (phenyl) silane (a yield of 19% based on the charged amount of phenylsilane). The conversion was 68% phenylsilane and 94% phenylacetylene.

Example 23 m-diethynylbenzene in place of phenylacetylene
6.7 g (53 mmol) were used, and other conditions were
Stirring was performed at 80 ° C. for 20 hours in the same manner as in Example 1. Anti
When the reaction solution was analyzed by GC, the reaction rate of phenylsilane was
64%, and the conversion of m-diethynylbenzene was 76%.
Was. 20 ml of dehydrated toluene was added to the reaction solution, and 1N salt was added.
It was dispersed in 20 ml of an acid aqueous solution. The organic phase is 1N hydrochloric acid
After washing with 5 ml of aqueous solution, the pH of the aqueous phase is adjusted with 5 ml of pure water at a time.
Washed until 6. CaSO _Four Dehydrated by
Thereafter, vacuum drying is performed at 5 mmHg for 50 hours to obtain 8.4 g.
Was obtained (67% yield). GPC (Gel Perm
Polystyrene exchange by crystallization chromatography
The calculated weight average molecular weight was about 2,200. For further fractionation
Using a GPC column with a molecular weight of 3600 to 1600
The components were separated and subjected to NMR and IR measurements.¹ H-NMR (ppm, CDCl_Three) 3.1 (C≡C-H), 4.7 (SiH ₂ ), 5.1 (S
iH), 7.3-7.9 (Ph-H).¹³ C-NMR (ppm, CDCl_Three) 78.1 (-C≡CH), 82.4 (-C(≡CH), 8
6.5 (Si-C≡C-), 107.2 (Si-C≡C-), 122.7 (Ph), 128.3 ~
135.9 (Ph).²⁹ Si-NMR (ppm, CDCl_Three) -59.8 (-SiH2-Ph), -63.5 (>SiH-P
h), -69.4 (>Si<). IR (cm^-1435, 476, 493, 602, 696, 73
6, 796, 845, 950, 1112, 1167, 1264, 1430, 1474, 15
92, 2156, 3069, 3291. From the NMR and IR spectra, this polymer was identified as
345825, the same polymer as the polymer synthesized in Example 1.
(Phenylsilyleneethynylene-1,3-phenyleneethyl
Nylene). From this result, metallization
Acetylene bond can be easily formed by using compounds as catalysts.
It has been shown that a silicon-containing polymer having the same can be synthesized.

Example 24 As a catalyst, barium diisopropoxide 0.26 mmol
l, 6.2 g (49 mmol) of m-diethynylbenzene was used as a diethynyl compound, and stirring was carried out at 80 ° C. for 3.75 hours under the same conditions as in Example 23. When the reaction solution was analyzed by GC, the conversion of phenylsilane was 90%, and the conversion of m-diethynylbenzene was 98%.
%Met. Add 60 ml of dehydrated tetrahydrofuran to the reaction solution.
And 20 ml of dehydrated toluene.
Dispersed in 0 ml. The organic phase is 5N aqueous 1N hydrochloric acid
After washing with 1 l, the aqueous phase was washed with 5 ml of a 13 wt% aqueous solution of sodium chloride until the pH of the aqueous phase reached 6. After dehydration with CaSO _4, vacuum drying was performed at 5 mmHg for 12 hours to obtain 9.8 g of a yellow polymer (yield: 83).
%). The weight average molecular weight in terms of styrene measured by GPC (gel permeation chromatography) was about 530,000. The NMR and IR spectra were the same as those of the polymer synthesized in Example 23.

Example 25 As a catalyst, 0.30 ml (0.34 ml) of a 1.04 mol / l lithium bis (trimethylsilyl) amide solution in hexane was used.
1 mmol), and the mixture was stirred at 80 ° C. for 8 hours under the other conditions as in Example 23. The reaction mixture was analyzed by GC. As a result, the conversion of phenylsilane was 65%, and the conversion of m-diethynylbenzene was 78%. 20 ml of dehydrated toluene was added to the reaction solution, and 20 ml of a 1 N hydrochloric acid aqueous solution was added.
Dispersed inside. The organic phase was washed with 5 ml of a 1 N aqueous hydrochloric acid solution, and then washed with 5 ml of a 13 wt% aqueous sodium chloride solution until the pH of the aqueous phase reached 6. After dehydration with CaSO _4, vacuum drying was performed at 5 mmHg for 50 hours to obtain 7.9 g of a polymer (yield: 68%). GPC
The weight average molecular weight in terms of styrene measured by (gel permeation chromatography) was 2,400. Further, using a preparative GPC column, the molecular weight was 3600 to 16
00 components were collected. The NMR and IR spectra of this component were the same as the polymer synthesized in Example 23.

[0109]

[Table 1] 1) Yield 2 for phenylsilane charged amount) AB: phenylethynyl (phenyl) silane 3) AB _2: Bis (phenylethynyl) (phenyl) silane

[0110]

[Table 2] 1) Yield 2 for phenylsilane charged amount) AB: phenylethynyl (phenyl) silane 3) AB _2: Bis (phenylethynyl) (phenyl) silane

[0111]

According to the present invention, by using a metal compound as a catalyst,
A silyl acetylene compound was easily produced from a silyl compound and an ethynyl compound, and a silicon-containing polymer was easily produced from a hydrosilyl compound and a diethynyl compound.

────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. ⁶ Identification symbol FI C08G 77/08 C08G 77/08 77/20 77/20 // C07B 61/00 300 C07B 61/00 300 (72) Inventor Ito Masayoshi 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa Prefecture Inside Mitsui Chemicals Co., Ltd. (72) Inventor Shiro Fujikake 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa prefecture

Claims (8)

[Claims] 1. R _4-m -SiH _m (wherein m is a positive integer of 4 or less, and R is an alkyl group having 1 to 30 carbon atoms, alkenyl group, alkynyl group, phenyl group, naphthyl group, etc.) Is an aromatic group of a halogen atom, a hydroxyl group, an amino group,
It may contain a substituent such as a carboxyl group or an ether group. When m is 1 or 2, each R may be the same or different. ) And R ¹
—C≡CH (wherein, R ¹ is a hydrogen atom or an aromatic group such as an alkyl group having 1 to 30 carbon atoms, an alkenyl group, an alkynyl group, a phenyl group or a naphthyl group, a halogen atom, a hydroxyl group, an amino group, (It may contain a substituent such as a carboxyl group or an ether group.) The ethynyl compound represented by the general formula (1) is reacted in the presence of a metal compound. ] (In the formula, m is a positive integer of 4 or less, and R is an aromatic group such as an alkyl group, an alkenyl group, an alkynyl group, a phenyl group or a naphthyl group having 1 to 30 carbon atoms, and is a halogen atom, a hydroxyl group, an amino group. And m may contain a substituent such as a carboxyl group, an ether group, etc. When m is 1 or 2, each R may be the same or different, and R ¹ may be a hydrogen atom or a C 1-30 group. An aromatic group such as an alkyl group, an alkenyl group, an alkynyl group, a phenyl group, and a naphthyl group, which may contain a substituent such as a halogen atom, a hydroxyl group, an amino group, a carboxyl group, or an ether group. A method for producing a silylacetylene compound represented by the formula: 2. R ² —SiH ₂ —R ³ (wherein R ² and R ³
Are each independently a hydrogen atom or an aromatic group such as an alkyl group having 1 to 30 carbon atoms, an alkenyl group, an alkynyl group, a phenyl group or a naphthyl group, and these groups are a halogen atom, a hydroxyl group, an amino group, a carboxyl group. And a substituent such as an ether group. ) And acetylene or the general formula (2). (In the formula, R ⁴ is a divalent aromatic group such as an alkylene group, alkenylene group, alkynylene group, phenylene group, or naphthylene group having 1 to 30 carbon atoms, or an aromatic group having 1 to 30 carbon atoms directly or by a crosslinking member. Alkylene group, alkenylene group, alkynylene group, a group linked to an aromatic group,
These groups may include a substituent such as a halogen atom, a hydroxyl group, an amino group, a carboxyl group, and an ether group. n is 0 or a positive integer of 4 or less. Wherein the diethynyl compound represented by the general formula (3) is reacted in the presence of a metal compound. (Wherein R ² and R ³ are each independently a hydrogen atom or an aromatic group such as an alkyl group having 1 to 30 carbon atoms, an alkenyl group, an alkynyl group, a phenyl group or a naphthyl group,
These groups may include a substituent such as a halogen atom, a hydroxyl group, an amino group, a carboxyl group, and an ether group. ) Or general formula (4) (Wherein R ² and R ³ are each independently a hydrogen atom or an aromatic group such as an alkyl group having 1 to 30 carbon atoms, an alkenyl group, an alkynyl group, a phenyl group or a naphthyl group,
These groups may include a substituent such as a halogen atom, a hydroxyl group, an amino group, a carboxyl group, and an ether group. R ⁴ is an alkylene group having 1 to 30 carbon atoms such as an alkylene group having 1 to 30 carbon atoms, an alkenylene group, an alkynylene group, a divalent aromatic group such as a phenylene group or a naphthylene group, It is a group linked to an alkenylene group, an alkynylene group, or an aromatic group, and these groups may include a substituent such as a halogen atom, a hydroxyl group, an amino group, a carboxyl group, or an ether group.
n is 0 or a positive integer of 4 or less. A method for producing a silicon-containing polymer having an acetylene bond containing a repeating unit represented by the formula (1). 3. The method according to claim 1, wherein the metal compound is an organometallic compound. 4. The method for producing a silylacetylene compound represented by the general formula (1), wherein the metal compound is an alkoxide. 5. The method for producing a silylacetylene compound represented by the general formula (1), wherein the metal compound is a metal amide in claim 1. 6. The silicon-containing polymer having an acetylene bond containing a repeating unit represented by the general formula (3) or (4), wherein the metal compound is an organometallic compound according to claim 2. Manufacturing method. 7. The production of a silicon-containing polymer having an acetylene bond containing a repeating unit represented by the general formula (3) or (4), wherein the metal compound is an alkoxide according to claim 2. Method. 8. The silicon-containing polymer having an acetylene bond containing a repeating unit represented by the general formula (3) or (4), wherein the metal compound is a metal amide according to claim 2. Production method.