CN108948061A - A kind of synthetic method of aryl three (three R radical siloxane bases) silane - Google Patents
A kind of synthetic method of aryl three (three R radical siloxane bases) silane Download PDFInfo
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- CN108948061A CN108948061A CN201810561945.9A CN201810561945A CN108948061A CN 108948061 A CN108948061 A CN 108948061A CN 201810561945 A CN201810561945 A CN 201810561945A CN 108948061 A CN108948061 A CN 108948061A
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- aryl
- silane
- radical siloxane
- synthetic method
- bases
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- -1 radical siloxane Chemical class 0.000 title claims abstract description 45
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 34
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 33
- 238000010189 synthetic method Methods 0.000 title claims abstract description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 22
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000012074 organic phase Substances 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 239000005052 trichlorosilane Substances 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 238000001914 filtration Methods 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 9
- 230000008901 benefit Effects 0.000 abstract description 4
- 238000005580 one pot reaction Methods 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 12
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
- 239000005054 phenyltrichlorosilane Substances 0.000 description 5
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 5
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000010907 mechanical stirring Methods 0.000 description 3
- 229940089952 silanetriol Drugs 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- 239000005046 Chlorosilane Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WOMUGKOOLXQCTQ-UHFFFAOYSA-N trichloro-(4-methylphenyl)silane Chemical compound CC1=CC=C([Si](Cl)(Cl)Cl)C=C1 WOMUGKOOLXQCTQ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- RIYSXAJPRALYFR-UHFFFAOYSA-M O[U]c1ccccc1 Chemical compound O[U]c1ccccc1 RIYSXAJPRALYFR-UHFFFAOYSA-M 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- REPWJCMYAKEVRF-UHFFFAOYSA-N phenyl(silyloxysilyloxy)silane Chemical class [SiH3]O[SiH2]O[SiH2]C1=CC=CC=C1 REPWJCMYAKEVRF-UHFFFAOYSA-N 0.000 description 1
- TZPUFQUQYUYVQC-UHFFFAOYSA-N phenylsilylmethanamine Chemical compound NC[SiH2]C1=CC=CC=C1 TZPUFQUQYUYVQC-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- FCVNATXRSJMIDT-UHFFFAOYSA-N trihydroxy(phenyl)silane Chemical compound O[Si](O)(O)C1=CC=CC=C1 FCVNATXRSJMIDT-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 229940094989 trimethylsilane Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0874—Reactions involving a bond of the Si-O-Si linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Silicon Polymers (AREA)
Abstract
The present invention relates to technical field of organic chemistry, to solve the problems, such as that there are step complexity during aryl three (three R radical siloxane bases) silane synthetic method, the present invention proposes a kind of synthetic method of aryl three (three R radical siloxane bases) silane, using organic solvent as solvent, trialkylsilane and hydrogen peroxide react 1-2 hours, are then respectively adding triethylamine, aryl trichlorosilane, then react 1-5 hour, filtering, concentration organic phase, obtain aryl three (three R radical siloxane bases) silane.This method takes one pot reaction, has the advantages that mild condition, yield are high, product purity is high, and simple process.
Description
Technical field
The present invention relates to technical field of organic chemistry, and in particular to a kind of conjunction of aryl three (three R radical siloxane bases) silane
At method.
Background technique
Aryl three (three R radical siloxane bases) silane is widely used in polymeric material field, (the three R radical siloxanes of aryl three
Base) silane-modified high molecular material can be obviously improved the heat resistance, weatherability and mechanical property of material, it is now widely used in silicon rubber
Glue is modified, resin modified and silicon oil modified.For example silicon rubber is modified: aryl three (three R radical siloxane bases) silane can be used for producing
High transparency LED packaging plastic, thermostable heat-conductive electron pouring sealant and the thermally conductive lithium battery group of heat-resistant fireproof encapsulate casting glue；Silicon tree
Rouge is modified: aryl three (three R radical siloxane bases) silane-modified epoxy resin is remarkably improved the mechanical property, heat-resisting of epoxy resin
Performance and antistripping ability；Silicon oil modified: aryl three (three R radical siloxane bases) silane-modified methyl-silicone oil is resistance to promotion silicone oil
High-temperature behavior, being prepared can be in the silicone oil product of 300-400 DEG C of steady operation.
There are mainly two types of route of synthesis for the preparation of aryl three (three R radical siloxane bases) silane, first is that under alkaline condition, benefit
It is reacted with aryl silanetriol with chlorosilane come synthesizing aryl three (three R radical siloxane bases) silane (Journal of
Organometallic Chemistry, 2003,686, (1-2), 313-320), or pass through phenyl silanetriol and triethylsilane
Reaction prepares phenyl trisiloxanes (Jpn 2015196672)；Second is that utilizing aryl tribenzyl silicon oxygen under transition metal-catalyzed
Alkane prepares aryl three (three R radical siloxane bases) silane (Jpn 2013170123 with reacting for chlorosilane；Jpn 2014218449；
RSC.Advance, 2014,19099-19102).But the aryl silanetriol that the former uses need to be hydrolyzed by aryl trichlorosilane
It is made, hydrolysising condition is difficult to control, it is easy to polymerization reaction occur, product purity is low；The latter needs previously prepared three benzyl of aryl
Radical siloxane and aryl silanetriol, step are complicated.
Summary of the invention
To solve the problems, such as that there are step complexity, this hairs during aryl three (three R radical siloxane bases) silane synthetic method
A kind of bright synthetic method for proposing aryl three (three R radical siloxane bases) silane, this method take one pot reaction, have condition temperature
The high advantage with yield height, product purity, and simple process.
The present invention is achieved by the following technical solutions: a kind of synthesis side of aryl three (three R radical siloxane bases) silane
Method are as follows: using organic solvent as solvent, trialkylsilane and hydrogen peroxide react 1-2 hours, are then respectively adding triethylamine, aryl
Trichlorosilane, then 1-5 hour is reacted, filtering, concentration organic phase obtain aryl three (three R radical siloxane bases) silane.
(the three R radical siloxane bases) silane of aryl three has the structural formula as described in (I):
In formula, R1Selected from H, CH3、CH2CH3、F、Cl、B、OCH3、OCH2CH3Middle one kind；R2、R3、R4It is respectively and independently selected from
CH3、CH2CH3、Ph、Middle one kind.
The organic solvent is selected from non-protonic solvent, preferably, non-protonic solvent is selected from benzene, toluene, diformazan
It is benzene, n-hexane, pentane, a kind of in hexamethylene.
The trialkylsilane and hydrogen peroxide molar ratio is 1: 1.1-2.Preferably, trialkylsilane is selected from triethyl group
It is silane, diphenylethlene base silane, trimethyl silane, a kind of in dimethylphenylsilaneand.
The molar ratio of the trialkylsilane and triethylamine is 1: 1-5.
The molar ratio of the aryl trichlorosilane and trialkylsilane is 1: 1.1-2.Preferably, aryl trichlorosilane
It is a kind of in phenyl trichlorosilane, p-methylphenyl trichlorosilane.
Synthetic route are as follows:
The reaction carries out under room temperature (15~30 DEG C).
Compared with prior art, the beneficial effects of the present invention are: this method takes one pot reaction, have mild condition,
The advantage that yield is high, product purity is high, and simple process.
Specific embodiment
Below by embodiment, invention is further described in detail, raw materials used in embodiment to be all made of commercial products
Or it is prepared using conventional method.
Illustrated embodiment is served only for explaining the present invention, is not intended to limit the scope of the present invention.
Embodiment 1
At room temperature, in three mouthfuls of reaction flasks equipped with magnetic stirring apparatus and constant pressure funnel, 500 milliliters of first are added
Benzene, triethylsilane (1mol) are then added dropwise to hydrogen peroxide (1.5mol), and reaction 1 hour is added dropwise, is then added dropwise to three again
Ethamine (1.5mol) and phenyl trichlorosilane (0.5mol) are filtered to remove triethylamine hydrochloride, organic phase after reacting 2 hours
It is concentrated to get aryl three (three R radical siloxane bases) silane, yield is greater than 85%.
Embodiment 2
At room temperature, in three mouthfuls of reaction flasks equipped with magnetic stirring apparatus and constant pressure funnel, 500 milliliters are being added just
Hexane, diphenylethlene base silane (1mol) are then added dropwise to hydrogen peroxide (2mol), reaction 1.5 hours are added dropwise, then again
It is added dropwise to triethylamine (2mol) and p-methylphenyl trichlorosilane (0.9mol), after reacting 3 hours, is filtered to remove triethylamine salt
Hydrochlorate, organic phase are concentrated to get corresponding aryl three (three R radical siloxane bases) silane, and yield is greater than 88%.
Embodiment 3
At room temperature, in three mouthfuls of reaction kettles equipped with mechanical stirring device and constant pressure funnel, 25 liters of n-hexanes are added,
Triethylsilane (100mol) is then added dropwise to hydrogen peroxide (160mol), and reaction 2 hours is added dropwise, is then added dropwise to three again
Ethamine (300mol) and phenyl trichlorosilane (60mol) are filtered to remove triethylamine hydrochloride after reacting 4 hours, and organic phase is dense
Contracting obtains corresponding aryl three (three R radical siloxane bases) silane, and yield is greater than 92%.
Embodiment 4
At room temperature, 25 liters of toluene are added in three mouthfuls of reaction kettles equipped with mechanical stirring device and constant pressure funnel, three
Methyl-monosilane (100mol) is then added dropwise to hydrogen peroxide (110mol), and reaction 01.5 hour is added dropwise, is then added dropwise to three again
Ethamine (400mol) and phenyl trichlorosilane (90mol) are filtered to remove triethylamine hydrochloride after reacting 2 hours, and organic phase is dense
Contracting obtains corresponding aryl three (three R radical siloxane bases) silane, and yield is greater than 93%.
Embodiment 5
At room temperature, 25 liters of toluene are added in three mouthfuls of reaction kettles equipped with mechanical stirring device and constant pressure funnel, two
Aminomethyl phenyl silane (100mol) is then added dropwise to hydrogen peroxide (200mol), and reaction 1 hour is added dropwise, is then added dropwise to again
Triethylamine (500mol) and phenyl trichlorosilane (50mol) are filtered to remove triethylamine hydrochloride, organic phase after reacting 1 hour
It is concentrated to get corresponding aryl three (three R radical siloxane bases) silane, yield is greater than 90%.
Claims (7)
1. a kind of synthetic method of aryl three (three R radical siloxane bases) silane, which is characterized in that the synthetic method are as follows: with
Organic solvent reacts 1-2 hours as solvent, trialkylsilane and hydrogen peroxide, is then respectively adding triethylamine, aryl trichlorine silicon
Alkane, then 1-5 hour is reacted, filtering, concentration organic phase obtain aryl three (three R radical siloxane bases) silane.
2. a kind of synthetic method of aryl three (three R radical siloxane bases) silane according to claim 1, which is characterized in that
(the three R radical siloxane bases) silane of aryl three has the structural formula as described in (I):
In formula, R1Selected from H, CH3、CH2CH3、F、Cl、B、OCH3、OCH2CH3Middle one kind；
R2、R3、R4It is respectively and independently selected from CH3、CH2CH3、Ph、Middle one kind.
3. a kind of synthetic method of aryl three (three R radical siloxane bases) silane according to claim 1 or 2, feature exist
In organic solvent is selected from non-protonic solvent.
4. a kind of synthetic method of aryl three (three R radical siloxane bases) silane according to claim 3, which is characterized in that
Non-protonic solvent is a kind of in benzene,toluene,xylene, n-hexane, pentane, hexamethylene.
5. a kind of synthetic method of aryl three (three R radical siloxane bases) silane according to claim 3, which is characterized in that
Trialkylsilane and hydrogen peroxide molar ratio are 1: 1.1-2.
6. a kind of synthetic method of aryl three (three R radical siloxane bases) silane according to claim 3, which is characterized in that
The molar ratio of trialkylsilane and triethylamine is 1: 1-5.
7. a kind of synthetic method of aryl three (three R radical siloxane bases) silane according to claim 3, which is characterized in that
The molar ratio of aryl trichlorosilane and trialkylsilane is 1: 1.1-2.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201810561945.9A CN108948061A (en) | 2018-06-01 | 2018-06-01 | A kind of synthetic method of aryl three (three R radical siloxane bases) silane |
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| CN201810561945.9A CN108948061A (en) | 2018-06-01 | 2018-06-01 | A kind of synthetic method of aryl three (three R radical siloxane bases) silane |
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU332090A1 (en) * | METHOD OF OBTAINING SILANOLS | |||
| US3965135A (en) * | 1975-09-24 | 1976-06-22 | Olin Corporation | Alkoxysilanol cluster compounds and their preparation |
| US3965136A (en) * | 1975-09-24 | 1976-06-22 | Olin Corporation | Alkoxysilane cluster compounds and their preparation |
| US4207247A (en) * | 1979-06-01 | 1980-06-10 | Olin Corporation | Preparation of trialkoxysilanols |
| DD236531A1 (en) * | 1985-04-24 | 1986-06-11 | Nuenchritz Chemie | PROCESS FOR THE PREPARATION OF TRIS- (TRIMETHYLSILOXY) -PHENYLSILANE |
| EP1219699A1 (en) * | 2000-12-26 | 2002-07-03 | Shin-Etsu Chemical Co., Ltd. | Method of dry cleaning and dry cleaning solvent therefor |
| JP2008070761A (en) * | 2006-09-15 | 2008-03-27 | Canon Inc | Electrophotographic photoreceptor, process cartridge and electrophotographic apparatus |
| CN103232485A (en) * | 2013-04-19 | 2013-08-07 | 扬州三友合成化工有限公司 | High-strength triisopropyl chlorosilane synthesis method |
| CN106957329A (en) * | 2015-10-09 | 2017-07-18 | 信越化学工业株式会社 | Mono-functional's branching type organosilicone compounds and its manufacture method |
-
2018
- 2018-06-01 CN CN201810561945.9A patent/CN108948061A/en active Pending
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU332090A1 (en) * | METHOD OF OBTAINING SILANOLS | |||
| US3965135A (en) * | 1975-09-24 | 1976-06-22 | Olin Corporation | Alkoxysilanol cluster compounds and their preparation |
| US3965136A (en) * | 1975-09-24 | 1976-06-22 | Olin Corporation | Alkoxysilane cluster compounds and their preparation |
| US4207247A (en) * | 1979-06-01 | 1980-06-10 | Olin Corporation | Preparation of trialkoxysilanols |
| DD236531A1 (en) * | 1985-04-24 | 1986-06-11 | Nuenchritz Chemie | PROCESS FOR THE PREPARATION OF TRIS- (TRIMETHYLSILOXY) -PHENYLSILANE |
| EP1219699A1 (en) * | 2000-12-26 | 2002-07-03 | Shin-Etsu Chemical Co., Ltd. | Method of dry cleaning and dry cleaning solvent therefor |
| JP2008070761A (en) * | 2006-09-15 | 2008-03-27 | Canon Inc | Electrophotographic photoreceptor, process cartridge and electrophotographic apparatus |
| CN103232485A (en) * | 2013-04-19 | 2013-08-07 | 扬州三友合成化工有限公司 | High-strength triisopropyl chlorosilane synthesis method |
| CN106957329A (en) * | 2015-10-09 | 2017-07-18 | 信越化学工业株式会社 | Mono-functional's branching type organosilicone compounds and its manufacture method |
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Application publication date: 20181207 |