U.S. patent application number 11/245786 was filed with the patent office on 2006-09-21 for (organothiomethyl)chlorosilanes and their preparation methods.
This patent application is currently assigned to Korea Institute of Science and Technology. Invention is credited to Joon Soo Han, Mi-kyoung Hong, Weon Cheol Lim, Bok Ryul Yoo.
Application Number | 20060211876 11/245786 |
Document ID | / |
Family ID | 35478313 |
Filed Date | 2006-09-21 |
United States Patent
Application |
20060211876 |
Kind Code |
A1 |
Yoo; Bok Ryul ; et
al. |
September 21, 2006 |
(ORGANOTHIOMETHYL)CHLOROSILANES AND THEIR PREPARATION METHODS
Abstract
This invention relates to (organothiomethyl)chlorosilanes and
methods for their preparation by the dehydrohalogenative Si--C
coupling reaction of oranothiomethyl halides with Si--H containing
chlorosilanes (hydrosilanes), wherein a mixture of oranothiomethyl
halide and hydrosilane is heated in the presence of tertiary amine
or organic salts (quaternary organoammonium and organophosphonium
halides to give (organothiomethyl)chlorosilanes, which is existing
a sulfur atom in alkyl chain, (formula::
R.sup.2SCH.sub.2SiCl.sub.2R.sup.1) in good yield, wherein R.sup.1
represents a hydrogen atom, halogen, or C.sub.1-C.sub.6 alkyl;
R.sup.2 is selected from the group consisting of C.sub.1-C.sub.6
alkyl or an aryl group. Especially, this reaction using organic
salt as a catalyst provide better economical matter and yield
compared with conventional methods, because only catalytic amount
of organic salt is required and the catalyst can be separated from
the reaction mixture and recycled easily.
Inventors: |
Yoo; Bok Ryul; (Seoul,
KR) ; Han; Joon Soo; (Kyunggi-Do, KR) ; Lim;
Weon Cheol; (Seoul, KR) ; Hong; Mi-kyoung;
(Gyeonggi-do, KR) |
Correspondence
Address: |
EDWARDS & ANGELL, LLP
P.O. BOX 55874
BOSTON
MA
02205
US
|
Assignee: |
Korea Institute of Science and
Technology
Seoul
KR
136-791
|
Family ID: |
35478313 |
Appl. No.: |
11/245786 |
Filed: |
October 7, 2005 |
Current U.S.
Class: |
556/426 |
Current CPC
Class: |
C07F 7/12 20130101 |
Class at
Publication: |
556/426 |
International
Class: |
C07F 7/08 20060101
C07F007/08 |
Foreign Application Data
Date |
Code |
Application Number |
Mar 21, 2005 |
KR |
10-2005-0023276 |
Claims
1. (Organothiomethyl)chlorosilane derivatives of the following
formula 1, ##STR4## wherein R.sup.1 represents a hydrogen atom,
halogen or C.sub.1-C.sub.6 alkyl; R.sup.2 is selected from the
group consisting of a C.sub.1-C.sub.6 alkyl or an aryl group.
2. A process for preparing (organothiomethyl)chlorosilane compounds
of the following formula 1, comprising a dehydrohalogenative
coupling reaction of hydrochlorosilane of the following formula 2
with organothiomethyl halides of the following formula 3 in the
presence of an organic salt (quaternary phosphonium salt or
quaternary ammonium salt) or tertiary amine as a catalyst, ##STR5##
wherein R.sup.1 represents a hydrogen atom, halogen or
C.sub.1-C.sub.6 alkyl; R.sup.2 is selected from the group
consisting of a C.sub.1-C.sub.6 alkyl or an aryl group; X
represents halogens.
3. A method of preparing (organothiomethyl)chlorosilane compounds
according to claim 2, wherein organic salt such as quaternary
phosphonium salt or quaternary ammonium salt, expressed by the
following Formula 4, is used for said catalyst, (R'').sub.4EX (4)
wherein E represents a phosphorus or nitrogen atom; X represents
halogens and R'' may be identical or different and is a
C.sub.1-C.sub.12 alkyl, phenyl group or
--CnH.sub.2n+1--C.sub.6H.sub.5 (n is an integer of 0-6); and two of
the R'' functional groups may be covalently bonded to form a
C.sub.4-C.sub.8 ring.
4. A method of preparing (organothiomethyl)chlorosilane compounds
according to claim 2, wherein organic salt such as quaternary
phosphonium salt or quaternary ammonium salt, expressed by the
following Formula 5, is used for said catalyst,
X(R'').sub.3E-Y-E(R'').sub.3X (5) wherein E, X and R'' are the same
as defined in claim 3; and Y can be C.sub.1-12 alkylene or aromatic
group optionally containing alkyls.
5. A method of preparing (organothiomethyl)chlorosilane compounds
according to claim 2, wherein the organic base of the following
formula 6 may be tertiary organic amines, (R'').sub.3N (6) wherein
R'' is the same as defined in claim 3.
6. A method of preparing (organothiomethyl)chlorosilane compounds
according to any one of claims 3, 4, or 5, wherein its immobilized
compound on inorganic or organic support is used as catalyst.
7. A method of preparing (organothiomethyl)chlorosilane compounds
according to claim 6, wherein said catalyst may be organic salt or
base immobilized on a silicon resin, silica, inorganic supporter or
organic polymer.
8. A method of preparing (organothiomethyl)chlorosilane compounds
according to claim 2, wherein 0.01-1 mol of said catalyst is used
for 1 mol of hydrochlorosilane expressed by formula 2.
9. A method of preparing (organothiomethyl)chlorosilane compounds
according to claim 2, wherein said coupling reaction is performed
in the temperature range of 70-150.degree. C.
10. A method of preparing (organothiomethyl)chlorosilane compounds
according to claim 2, wherein said coupling reaction is performed
without a reaction solvent.
Description
CROSS REFERENCE TO RELATED APPLICATIONS
[0001] This application is based on, and claims priority from
Korean Application No. 2005-0023276, filed on Mar. 21, 2005, the
disclosure of which is hereby incorporated by reference.
FIELD OF THE INVENTION
[0002] This invention relates to (organothiomethyl)chlorosilanes
and methods for their preparation by the dehydrohalogenation Si--C
coupling reaction of organothiomethyl halides with Si--H containing
chlorosilanes (hydrosilanes), wherein a mixture of organothiomethyl
halide and hydrosilane is heated in the presence of tertiary amine
or organic salts (quaternary organoammonium and organophosphonium
halides to give (organothiomethyl)chlorosilanes, which is existing
a sulfur atom in alkyl chain, (formula::
R.sup.2SCH.sub.2SiCl.sub.2R.sup.1) in good yield, wherein R.sup.1
represents a hydrogen atom, halogen, or C.sub.1-C.sub.6 alkyl; R2
is selected from the group consisting of C.sub.1-C.sub.6 alkyl or
an aryl group. Especially, this reaction using organic salt as a
catalyst provide better economical matter and yield compared with
conventional methods, because only a catalytic amount of organic
salt is required and the catalyst can be separated from the
reaction mixture and recycled easily. The
(organothiomethyl)chlorosilane compounds can be widely used for the
synthesis of various silane monomers, silicone polymers, and
surfactants.
BACKGROUND OF THE INVENTION
[0003] Organosilicon compounds are important starting materials for
organosilicon polymers. Especially, sulfur atom containing
organosilicon compounds are interesting and potential monomer
precursors in synthesizing functional inorganic polymers. In 1975,
Voronkov and co-workers reported that sodium alkylthiolate reacted
with haloalkylalkoxysilane to give the corresponding
alkylthio-substituted products through the C--S coupling reaction,
eliminating sodium halide [Voronkov, M. G.; Sorokin, M.S.; D'yakov,
V.M.; Sigalov, M.V. Zhurnal Obshchei Khimii, 1975, 45(8), 1807-11].
Here, 1,1,1-trimethoxy-3-thio-1-silabutane was synthesized by the
reaction of methyl iodide with sodium trimethylsilylmethylthiolate
[NaSCH.sub.2Si(OMe).sub.3].
[0004] In 2001, Sorokin; Voronkov reported that a sulfur
atom-containing alkylalkoxysilane could be prepared by a Si--C
coupling reaction of haloalkylalkoxysilane with RSMgX in
tetrahydrofuran in situ [Sorokin, M. S.; Voronkov, M. G. Russian
Journal of General Chemistry, 2001, 71(12), 1883-90].
[0005] As explained above, the current known methods for preparing
sulfur atom-containing organosilanes are limitedly synthesizing
alkoxysilanes by S--C coupling of haloalkylalkoxysilane with
organometal reagents. However, these methods are not applied for
chlorosilane compounds containing Si--Cl bond(s), which can be
modified by alcohol, amine, organometal reagents, etc. and
haloalkylalkoxysilane should be prepared by two step reactions:
hydrosilylation and methoxylations. The former reaction requires a
very expensive platinum catalyst and the latter evolves HCl gas in
the reaction of Si--Cl with methanol and thus needs a trapping
process of HCl.
[0006] The inventors have obtained a patent on a method of
preparing a variety of organosilicon compounds by the
dehydrohalogenation of alkyl halide and chlorosilane in the
presence of the tertiary phosphine [U.S. Pat. No. 6,251,057, Korean
Patent No. 306574]. ##STR1##
[0007] The inventors also prepared organosilicon compounds with
Si--Cl bonds from the Si--C coupling reaction of
chloromethyl-substituted organosiliocn compounds with chlorosilane
containing Si--H bond in better yield using tetraalkylphosphonium
salt catalyst instead of tertiary phosphine or amine compound. This
tetraalkylphosphonium salt catalyzed reaction provide a better
yield compared with phosphine compound-catalyzed reaction, because
the catalyst can be separated from the reaction mixture and
recycled easily [Jung, I.; Yoo, B.; Han, J.; Kang, S. U.S. Pat. NO,
6,392,077 ].
[0008] However, a Si--C coupling reaction of hydrochlorosilane
containing Si--H bond with organothiomthyl halide in the presence
of organic amine, phosphine, or organic salt have never been
reported
SUMMARY OF THE INVENTION
[0009] As above-mentioned, the present inventors have discovered
that a coupling reaction of organothiomethyl halides and
hydrochlorosilanes in the presence of tertiary phosphines,
quaternary ammonium salt, or quaternary phosphonium salt as a
catalyst proceeded to give the corresponding coupled products,
(organothiomethyl)chlorosilicon compounds containing a sulfur atom
in organic group, in good yields.
[0010] Accordingly, it is an object of the present invention to
provide new (organothiomethyl)chlorosilane and methods for their
preparation.
DETAILED DESCRIPTION OF THE INVENTION
[0011] The present invention relates to
(organothiomethyl)chlorosilanes and methods for their preparation
by the dehydrohalogenative Si--C coupling reaction of
oranothiomethyl halides with hydrosilanes expressed by the
following Formula 1 in the presence of quaternary organophosphonium
salt catalyst, ##STR2## wherein R.sup.1 represents a hydrogen atom,
halogen, or C.sub.1-C.sub.6 alkyl; R.sup.2 is selected from the
group consisting of C.sub.1-C.sub.6 alkyl or an aryl group.
[0012] The present invention relates to
(organothiomethyl)chlorosilanes expressed by the following Formula
1 and methods for their preparation by the dehydrohalogenative
Si--C coupling reaction of oranothiomethyl halides expressed by the
following Formula 3 with hydrosilanes expressed by the following
Formula 2 in the presence of quaternary organophosphonium salt,
quaternary organoammonium salt, tertiary amine as a catalyst.
##STR3## wherein R, R.sup.2, and X are the same as defined
above.
[0013] The details of the present invention are described as
follows.
[0014] The present invention relates to preparing new organosilicon
compounds having Si--Cl bonds and organic group with a sulfur atom,
which can be widely used for the synthesis of various functional
organosilicon compounds and silicone monomer, polymers, binders,
etc.
[0015] In a typical preparation, hydrochlorosilanes expressed by
formula II in this invention can be used instead of
(haloalkyl)alkoxysilanes used in conventional methods and the
reaction is carried out at a lower temperature from 70 to 150
.degree. C., preferably 100 to 120 .degree. C. than that in the
dehydrogenative Si--C coupling of alkyl halide, and further can be
applied for a continuous process. The reaction can be carried out
using a small amount of quaternary organophosphonium salt or
quaternary organoammonium salt as a catalyst. Additionally, the
catalyst can be easily recovered from the reaction product and has
good catalytic activity for reuse.
[0016] The coupling reaction of hydrochlorosilanes expressed by
formula II with organothiomethyl halides expressed by formula III
in the present invention in the presence of a catalyst of which one
among quaternary organophosphonium salt, quaternary organoammonium
salt, or organic base can afford organothiomethylchlorosilanes
compounds in good yields. In a typical preparation,
hydrochlorosilanes of the following formula II, organothiomethyl
halides of formula III, and a catalyst are placed all together into
a sealed stainless steel tube under inert atmosphere after sealing
the reaction tube with a stainless steel stopper. The reaction is
carried out at high temperature and under high pressure.
[0017] In the coupling reaction explained above, the amount of
organothiomethyl halides of formula III is equivalent or more,
preferably 1 to 5 folds, relative to the amount of the
hydrochlorosilane compounds of formula II. Organic salt or organic
base is used as a catalyst in an amount sufficient to catalyze the
reaction, generally, 1 to 100 mol %, preferably 3 to 15 mol %,
relative to the mole of the hydrochlorosilane compounds of formula
II.
[0018] In the coupling reaction explained above, the coupling
reaction can be carried out in most aliphatic or aromatic
hydrocarbon solvents such as hexane, benzene toluene, etc, but also
proceeds in neat condition.
[0019] In the coupling reaction explained above, the reaction is
carried out at a temperature from 70 to 150 .degree. C., preferably
100 to 120 .degree. C.
[0020] In the coupling reaction explained above, the heating and
stirring of a reaction mixture may be applied for a certain period
of time, generally 1 hr to about 48 hours to complete the reaction.
When the reaction is completed, the target compound can be obtained
by distilling the reaction mixture under normal or reduced
pressure.
[0021] The organic salt catalysts such as quaternary
organophosphonium salt and quaternary organoammonium salt can be
easily recovered from the reaction mixture by two following
methods: first, the products are distilled out under atmospheric
pressure and vacuum and the remaining catalyst can be washed with
aliphatic hydrocarbon solvents and purified by recrystallization.
The recovery ratio can be as high as 90%. Second hydrocarbon
solvents are added to the product mixture to precipitate out the
catalyst and the catalyst is filtered and recovered for recycling.
When recovered catalyst is reused for the Si--C coupling reaction,
the similar activity is shown in the repeated five runs of coupling
reactions.
[0022] As mentioned above, even though the recovery ratio can be as
high as 90%, when organic phophonium salt immobilized on silicone
resins, silica, or zeolite is used the recovery of the catalyst is
more convenient and easier for recycling as previously reported
(Jung, I. N.; Cho, K. D.; Lim, J, C; Yoo, B. R., U.S. Pat. No.
4,613,491).
[0023] The details of starting materials and catalysts used in the
Si--C coupling reaction in the present invention are described as
follows.
[0024] As explained above, hydrochlorosilanes with Si--H bond
expressed by formula 2 used in this invention may be
dichlorosilane, trichlorosilane, and alkyldichlorosilane.
[0025] Organothiomethyl halide, raw material of this invention,
expressed by the following Formula 3 may be alkylthiomethyl halide
and arylthiomethyl halide
[0026] Examples of the organothiomethyl halide expressed by Formula
2 are methylthiomethyl chloride and phenylthiomethyl chloride,
etc.
[0027] The catalyst of this invention expressed by the following
Formulae 4, 5 and 6 may be quaternary phosphonium salt, quaternary
ammonium salts and tertiary amine. (R'').sub.3N (6)
[0028] Quaternary organic salt in this invention can be expressed
by the following Formula 4 and 5, E(R'').sub.4X (4) wherein E
represents a phosphorus or a nitrogen atom; X may be chloro, bromo
or iodo; and R'' may be identical or different and is a
C.sub.1-C.sub.12 alkyl, phenyl group or
--CnH.sub.2n+1--C.sub.6H.sub.5 (n is an integer of 0-6); and two of
the R'' functional groups may be covalently bonded to form a
C.sub.4-C.sub.8 ring. X(R'').sub.3E-Y-E(R'').sub.3X (5) wherein E,
X and R'' are defined as above; and Y can be C.sub.1-12 alkylene or
aromatic group optionally containing alkyls.
[0029] The organic, salt of the following formula 4 used in this
invention may be quaternary organophosphonium halide or quaternary
organoammonium halide. Specific examples of the quaternary
organophosphonium salt are tetrabutylphosphonium chloride,
tetrabutylphosphonium bromide, tetrabutylphosphonium iodide,
methyltributylphosphonium chloride, tetramethylphosphonium bromide,
tetraethylphosphonium chloride, hexyltriphenylphosphonium chloride,
and tetraphenylphosphonium chloride, etc. Specific examples of
quaternary organoammonium halide are the same except that nitrogen
atom is replaced instead of phosphorous atom of quaternary
organophosphonium halide. Specific examples of quaternary
organophosphonium salt of the following formula 5 used in this
invention may be bis(chlorotrialkylphosphonium)alkylene,
bis(chlorotrialkylphosphonium)phenylene,
bis(chlorotriphenylphosphonium)alkylene,
bis(chlorotriphenylphosphonium)phenylene, and etc. Specific
examples of quaternary organoammonium halide of the following
formula 5 used in this invention are the same except that nitrogen
atom is replaced instead of phosphorous atom of quaternary
organophosphonium halide.
[0030] Tertiary amine in this invention can be expressed by the
following Formula 6 (R'').sub.3N (6) wherein R'' is same as defined
above.
[0031] The organic base of the following formula 5 used in this
invention may be tertiary organic amines.
[0032] Specific examples of tertiary amine compounds are
trimethylamine, triethylamine, tributylamine, etc.
[0033] As explained above, even though organic salt or organic base
is used for the Si--C coupling reaction in this invention, organic
salt or organic base immobilized on silicone resins, silica, or
zeolite can be easier recovery and more convenient for
recycling.
[0034] As explained above, this method uses a small amount of
catalyst, which can be easily recovered for reuse and has good
catalytic activity even at low temperature. Considering these
advantages, the present invention is a very economical and
effective method, which can be used for the preparation of new and
various organothiomethylsilicon compounds. Furthermore, its process
is very simple and the production cost is relatively low.
[0035] Also, the organosilicon compounds, expressed by formula 1,
prepared by this invention can be widely used for the synthesis of
various polymers and silicone surfactants, because organothiomethyl
group of silane can be converted to sulfoxide group applicable to
hydrophilic silicones. These compounds are new type hydrophilic
silicone different from modified polyethylene- or
propyleneoxide-silicones. Generally dialkyl sulfide can be
converted to dialkyl sulfonoxide or sulfone by the oxidation
reaction with hydrogen peroxide (A. Kh. Sharipov, Russian Journal
of Applied Chemistry, 2003, 76, 108-113). Thus
oragnothiomethylchlorosilanes may be chemically bonded to inorganic
substrate and oxidized to make surface to be hydrophilic.
[0036] The invention will be further illustrated by the following
examples. However, they should not construed as limiting the scope
of the present invention.
Example 1
Preparation of (methylthiomethyl)trichlorosilane
[0037]
HSiCl.sub.3+CH.sub.3SCH.sub.2Cl.fwdarw.CH.sub.3SCH.sub.2SiCl.sub.3
[0038] A reaction chamber (a 250 mL stainless steel tube) dried in
an oven was cooled to room temperature under dry nitrogen gas
methylthiomethyl chloride (138.1 g, 1.02 mol), trichlorosilane
(138.1 g, 1.02 mol) and tetrabutylphosphonium chloride (5.01 g,
0.0169 mol) were put in the chamber under nitrogen atmosphere. The
opening of the reaction chamber was closed with a cover and the
reaction was carried out at 100 .degree. C. for 12 hours. This
reaction mixture was distilled under normal pressure to give
(methylthiomethyl)trichlorosilane (52.2 g, yield: 73.8%).
[0039] .sup.1H-NMR(CDCl.sub.3,ppm) .delta.2.26(s, 3H, CH.sub.3),
2.41(s, 2H, CH.sub.2)
Example 2
Preparation of methyl(methylthiomethyl)dichlorosilane
[0040]
CH.sub.3SiHCl.sub.2+CH.sub.3SCH.sub.2Cl.fwdarw.CH.sub.3SCH.sub.2Si-
CH.sub.3Cl.sub.2
[0041] As in Example 1, methylthiomethyl chloride (49.2 g, 0.428
mol), methyldichlorosilane (49.2 g, 0.428 mol) and
tetrabutylphosphonium chloride (2.10 g, 0.00713 mol) were put in a
250 mL stainless steel tube under nitrogen atmosphere. The reaction
chamber was closed with a cover and the reaction was carried out at
100 .degree. C. for 12 hours. This reaction mixture was distilled
to give 25.04 g of methyl(methylthiomethyl)dichlorosilane in 20.2%
yield.
[0042] .sup.1H-NMR(CDCl.sub.3,ppm) .delta.0.87(s, 3H, SiCH.sub.3),
2.27(s, 3H, SCH.sub.3), 2.28(s, 2H, CH.sub.2)
Example 3
Preparation of (phenylthiomethyl)trichlorosilane
[0043]
HSiCl.sub.3+C.sub.6H.sub.5SCH.sub.2Cl.fwdarw.C.sub.6H.sub.5SCH.sub-
.2SiCl.sub.3
[0044] As in Example 1, phenylthiomethyl chloride (2.97 g, 0.0187
mol)), trichlorosilane (7.61 g, 0.0562 mol) and
tetrabutylphosphonium chloride (2.97 g, 0.0187 mol) were put in a
50 mL stainless steel tube under nitrogen atmosphere. The reaction
chamber was closed with a cover and the reaction was carried out at
120 .degree. C. for 12 hours. This reaction mixture was distilled
under low pressure to give 2.15 g of
(phenylthiomethyl)trichlorosilane in 44.5% yield.
[0045] .sup.1H-NMR(CDCl.sub.3, ppm) .delta.2.91 (s, 3H, CH.sub.2),
7.21-7.42 (m, 5H, ArH)
Example 4
Preparation of methyl(phenylthiomethyl)dichlorosilane
[0046]
CH.sub.3SiHCl.sub.2+C.sub.6H.sub.5SCH.sub.2Cl.fwdarw.C.sub.6H.sub.-
5SCH.sub.2SiCH.sub.3Cl.sub.2
[0047] As in Example 1, phenylthiomethyl chloride (3.31 g, 0.0209
mol), methyldichlorosilane (7.23 g, 0.0628 mol) and
tetrabutylphosphonium chloride (0.615 g, 0.00209 mol) were put in a
50 mL stainless steel tube under nitrogen atmosphere. The reaction
chamber was closed with a cover and the reaction was carried out at
120 .degree. C. for 12 hours. This reaction mixture was distilled
under low pressure to give 1.82 g of
methyl(phenylthiomethyl)dichlorosilane in 36.9% yield.
[0048] .sup.1H NMR(CDCl.sub.3,ppm) .delta.0.84(s, 3H, SiCH.sub.3 ),
2.71(s, 2H, CH.sub.2), 7.19-7.37(m, 5H, ArH)
Example 5
Preparation of (methylthiomethyl)trichlorosilane
[0049]
HSiCl.sub.3+CH.sub.3SCH.sub.2Cl.fwdarw.CH.sub.3SCH.sub.2SiCl.sub.3
1) Reaction in the presence of triethylamine
[0050] As in Example 1, methylthiomethyl chloride (1.16 g, 0.0120
mol), trichlorosilane (8.13 g, 0.0600 mol) and triethylamine (1.21
g, 0.0120 mol) were put in a 50 mL stainless steel tube under
nitrogen atmosphere. The reaction chamber was closed with a cover
and the reaction was carried out at 100 .degree. C. for 12 hours.
This reaction mixture was distilled under low pressure to give 1.12
g of (methylthiomethyl)trichlorosilane in 47.8% yield.
2) Reaction in the presence of tetrabutylammonium chloride
[0051] As in Example 1, methylthiomethyl chloride (1.04 g, 0.0108
mol), trichlorosilane (4.39 g, 0.0324 mol) and tetrabutylammonium
chloride (0.301 g, 0.00108 mol) were put in a 50 mL stainless steel
tube under nitrogen atmosphere. The reaction chamber was closed
with a cover and the reaction was carried out at 100 .degree. C.
for 12 hours. This reaction mixture was distilled under low
pressure to give 1.08 g of (methylthiomethyl)trichlorosilane in 51
% yield.
[0052] Having now fully described the present invention, it will be
apparent to one of ordinary skill in the art that many changes and
modifications can be made thereto without departing from the spirit
of scope of the invention as set forth herein.
INDUSTRIAL APPLICABILITY
[0053] As explained above, the present invention relates to
(organothiomethyl)chlorosilanes with a sulfur-containing alkyl
group and their preparation expressed by Formulas 1 by the Si--C
coupling reaction of Si--H containing chlorosilanes with
organothiomethyl halide in the presence of quaternary organic salt
catalyst or amines. Especially, this reaction using organic salt as
a catalyst provide better economical matter and yield compared with
conventional methods, because only catalytic amount of organic salt
is required and the catalyst can be separated from the reaction
mixture and recycled easily. Si--H containing silanes used in this
invention are an easily available material in the industry.
Therefore, this invention is effective for industrial mass
production of (organothiomethyl)chlorosilane compounds, which are
widely used for raw material of silicon polymers, silicone
adhesives, etc.
* * * * *