CN1807432A - Methylphenyldichlor disilane synthesis method - Google Patents
Methylphenyldichlor disilane synthesis method Download PDFInfo
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- CN1807432A CN1807432A CN 200510061266 CN200510061266A CN1807432A CN 1807432 A CN1807432 A CN 1807432A CN 200510061266 CN200510061266 CN 200510061266 CN 200510061266 A CN200510061266 A CN 200510061266A CN 1807432 A CN1807432 A CN 1807432A
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- alkyl imidazole
- synthetic method
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- chlorobenzene
- alkyl
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- QIIUATJDXXKQMX-UHFFFAOYSA-N dichloro-methylsilyl-phenylsilane Chemical compound C[SiH2][Si](Cl)(Cl)C1=CC=CC=C1 QIIUATJDXXKQMX-UHFFFAOYSA-N 0.000 title 1
- 238000001308 synthesis method Methods 0.000 title 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 18
- 238000004821 distillation Methods 0.000 claims abstract description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 44
- -1 alkyl imidazole Chemical compound 0.000 claims description 42
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims description 30
- 238000010189 synthetic method Methods 0.000 claims description 13
- 239000002994 raw material Substances 0.000 claims description 10
- 238000011084 recovery Methods 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 7
- 239000012429 reaction media Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- LEHNQGSPRXHYRT-UHFFFAOYSA-N 2-dodecyl-1h-imidazole Chemical class CCCCCCCCCCCCC1=NC=CN1 LEHNQGSPRXHYRT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 27
- 239000000463 material Substances 0.000 abstract description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000004062 sedimentation Methods 0.000 abstract description 3
- 238000007086 side reaction Methods 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 238000006386 neutralization reaction Methods 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 238000010908 decantation Methods 0.000 abstract 1
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002632 imidazolidinyl group Chemical group 0.000 abstract 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 abstract 1
- 239000005048 methyldichlorosilane Substances 0.000 abstract 1
- 238000005057 refrigeration Methods 0.000 abstract 1
- 229940083608 sodium hydroxide Drugs 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 238000007711 solidification Methods 0.000 abstract 1
- 230000008023 solidification Effects 0.000 abstract 1
- 238000005292 vacuum distillation Methods 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 7
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 7
- QLNWYPZFNHLJGO-UHFFFAOYSA-N dichloromethyl(phenyl)silane Chemical class ClC(Cl)[SiH2]C1=CC=CC=C1 QLNWYPZFNHLJGO-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MMDFSEGJGPURPF-UHFFFAOYSA-N 2-octyl-1h-imidazole Chemical class CCCCCCCCC1=NC=CN1 MMDFSEGJGPURPF-UHFFFAOYSA-N 0.000 description 2
- 239000002608 ionic liquid Substances 0.000 description 2
- 239000005055 methyl trichlorosilane Substances 0.000 description 2
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 2
- 229920000548 poly(silane) polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910008045 Si-Si Inorganic materials 0.000 description 1
- 229910006411 Si—Si Inorganic materials 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 229920000555 poly(dimethylsilanediyl) polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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Abstract
The convention relates to the Synthesis of methyl phenyl dichlorosilane. It needs to resolve the technical matters of offering a methyl phenyl dichlorosilane's synthesis which the material is cheap, nonuse of volatile solvent, low reaction temperature, litter side reaction and high productivity. The character rests with using methyldichlorosilane and chlorobenzene as material, imidazolidinyl as acid- attach agent in the process of synthesize and the producing alkyl imidazolalcaine salt as reaction agent in molten condition. Reaction by heating and agitating fully, cedin g the upper product by decantation and collecting distillation by vacuum distillation, then the production of methyl phenyl dichlorosilane will be getted. At the same time, after the reaction ended, separating alkyl imidazolalcaine salt and production by refrigeration, solidification and sedimentation, the alkyl imidazolalcaine which is regetted by neutralization of sodium-hydroxide, potassium hydroxide and alkyl imidazolalcaine salt can be used circularly.
Description
Technical field
The present invention relates to organic chemistry filed, specifically be a kind of alkyl imidazole as acid binding agent, fusion alkyl imidazole hydrochloride is the method for synthesis of methyl phenyl dichlorosilane under the reaction medium.
Background technology
Dichloromethyl phenylsilane is the raw material of synthetic polyphenylmethyl base silane.The main chain of polysilane is made up of Siliciumatom, electronics is in the extensive delocalization of Si-Si main chain, have many special performances such as special photoconductivity, electroconductibility, thermochromism, electroluminescence and nonlinear optics thus, therefore its special structure, performance and potential using value are becoming the research focus (Liao Xuewei etc. of materials chemistry, organosilicon material, 2000,14 (5), 1-3; R.West, L.D.David, J.Am.Soc.Chem., 1981,103,7352).The side group asymmetry that the polyphenylmethyl base silane is had, good solvability, thermostability, chemical stability and film-forming properties make it synthetic just replacing polydimethyl silane with performance and become the emphasis of polysilane investigation of materials.Usually, the synthetic of polyphenylmethyl base silane is under nitrogen protection, obtained with potassium or sodium effect in toluene by dichloromethyl phenylsilane.And as the monomeric dichloromethyl phenylsilane of polyphenylmethyl base silane, then be phenyl-magnesium-bromide and METHYL TRICHLORO SILANE reaction (Liao Xuewei etc., organosilicon material, 2000,14 (5), 1-3; ), or phenyl lithium and METHYL TRICHLORO SILANE reaction (Shi Baochuan etc., Nanjing Normal University's journal, 1997,20 (3), 26) makes.More than two kinds of methods all limit its industrial applications because of cost is too high, at present chemical circle is just in the novel method of active research and exploitation, wherein halogeno-benzene and dimethyl dichlorosilane (DMCS) obtain the method for dichloromethyl phenylsilane because of having reaction simply through the pyrocondensation unification step under certain condition, characteristics such as cost is low, and is easy to operate and have the potential prospects for commercial application.
Summary of the invention
The technical issues that need to address of the present invention are, provide a kind of raw material cheap, do not use solvent flashing, and temperature of reaction is low, and side reaction is few, the synthetic method of the dichloromethyl phenylsilane that yield is high.
Another technical problem that the present invention need solve is that the efficient recovery alkyl imidazole utilizes again.
Since the eighties of last century the nineties, ionic liquid (being generally alkyl imidazole or pyridinium salt) has all obtained application in fields such as organic synthesis, biocatalysis chemistry, material, theoretical chemistries.Compare with conventional organic solvents, make reaction medium, can improve speed of reaction, selectivity of product, product easily separated (T.Welton, Chem.Rev., 1999,99,2071 simultaneously with ionic liquid; P.Wasserscheid, W.Keim, Angew.Chem.Int.Ed., 2000,39,3772-3789; L.A.Blanchard et al, Nature, 1999,399:6731).Ion liquid application is also for the invention provides new technical thought.
The synthetic method of dichloromethyl phenylsilane of the present invention, it is characterized in that with dimethyl dichlorosilane (DMCS) and chlorobenzene be raw material, in building-up process, utilize alkyl imidazole as acid binding agent, the alkyl imidazole hydrochloride that generates under molten state as reaction medium, heated and stirred is fully reacted, decanting process is told the upper strata product, and cut is collected in underpressure distillation, obtains the product dichloromethyl phenylsilane.
Described alkyl imidazole is one or more the mixture in methyl, ethyl, normal-butyl, n-hexyl, n-octyl, positive decyl and the dodecyl imidazoles.
Described raw material thing dimethyl dichlorosilane (DMCS): chlorobenzene: the mol ratio of alkyl imidazole is 1: 1～1.2: 1～1.2.As preferably, mol ratio is 1: 1: 1.
Thereby the present invention makes the alkyl imidazole hydrochloride separate with the product dichloromethyl phenylsilane by cooling curing and sedimentation after reacting and finishing, and alkyl imidazole hydrochloride wherein and alkali neutralize to such an extent that alkyl imidazole is recovered.
Its reaction mechanism is in conjunction with Fig. 1 schematically as follows:
R＝C
nH
2n-1，n＝1，2，4，6，8，10，12
Key of the present invention is to utilize alkyl imidazole as acid binding agent in building-up process, and the alkyl imidazole hydrochloride of generation as reaction medium, makes dimethyl dichlorosilane (DMCS) and chlorobenzene condensation reaction be easy to carry out under molten state.Simultaneously, by cooling curing, sedimentation the alkyl imidazole hydrochloride is separated thereby reaction finishes the back with product, alkyl imidazole hydrochloride and sodium hydroxide, potassium hydroxide neutralization obtain alkyl imidazole again and recycle.
The method and the direct heat condensation method of bibliographical informations such as the present invention and Liao Xuewei and Shi Baochuan relatively have following characteristics:
1, use chlorobenzene and dimethyl dichlorosilane (DMCS) to be raw material, lower cost;
2, do not use the contour volatile solvent of anhydrous diethyl ether, help environmental protection;
3, reaction and product lock out operation are simple;
4, can recycling as the alkyl imidazole of reaction medium and catalyzer;
5, temperature of reaction is low, and side reaction is few, the yield height.
Description of drawings
Fig. 1 is the inventive method reaction mechanism synoptic diagram.
Embodiment
Below by embodiment, technical scheme of the present invention is described in further detail.
Methylimidazole used in the present invention is a commercial prod, and the preparation method of other alkyl imidazole is referring to document (Wang Xixin etc., chemical reagent, 2001,23 (5), 306).
The preparation process of dichloromethyl phenylsilane: in 500 milliliters there-necked flask; add dimethyl dichlorosilane (DMCS) (0.5 mole) and chlorobenzene (0.5 mole), under the nitrogen protection, drip alkyl imidazole (0.5 mole) by dropping funnel; slowly be warming up to 70～90 ℃; stirring reaction 4～6 hours leaves standstill, and is cooled to room temperature; decanting process is told the upper strata product; 80～85 ℃/1.33kPa cut is collected in underpressure distillation, and carries out purity check on the GC-MS combined instrument, calculates the dichloromethyl phenylsilane yield.Lower floor's solids or fraction are heated to 40～50 ℃, carefully add sodium hydroxide (0.5 mole) in batches, and cooling is filtered, and alkyl imidazole is reclaimed in underpressure distillation.
Embodiment
Below by embodiment technical solution of the present invention is described further.
Embodiment 1
In 500 milliliters there-necked flask, add dimethyl dichlorosilane (DMCS) (0.5 mole) and chlorobenzene (0.5 mole), under the nitrogen protection; drip Methylimidazole (0.5 mole) by dropping funnel, dropwised in about 1 hour, slowly be warming up to 80 ℃; stirring reaction 5 hours leaves standstill, and is cooled to room temperature; lower floor has solid to separate out; decanting process is told the upper strata product, and 80～85 ℃/1.33kPa cut is collected in underpressure distillation, obtains 80.1 gram dichloromethyl phenylsilanes; yield 84%, GC-MS are analyzed its purity 98.5%.Lower floor's solids is heated to 50 ℃, and fusing carefully adds sodium hydroxide (0.5 mole) in batches, and cooling is filtered, and Methylimidazole is reclaimed in underpressure distillation, gets 35.8 grams, the rate of recovery 87.3%.
Embodiment 2
Among the embodiment 1, drip Methylimidazole (0.6 mole), obtain 80.9 gram dichloromethyl phenylsilanes, yield 84.2%, purity 98.3%.Lower floor's solids is heated to 50 ℃, and fusing carefully adds sodium hydroxide (0.6 mole) in batches, and cooling is filtered, and Methylimidazole is reclaimed in underpressure distillation, gets 42.3 grams, the rate of recovery 86.0%.
Embodiment 3
In 500 milliliters there-necked flask; add dimethyl dichlorosilane (DMCS) (0.5 mole) and chlorobenzene (0.5 mole); under the nitrogen protection; drip ethyl imidazol(e) (0.5 mole) by dropping funnel; dropwised in about 1 hour; slowly be warming up to 85 ℃; stirring reaction 5 hours leaves standstill, and is cooled to room temperature; lower floor has solid to separate out; decanting process is told the upper strata product, and 80～85 ℃/1.33kPa cut is collected in underpressure distillation, obtains 76.5 gram dichloromethyl phenylsilanes; yield 80.2%, GC-MS are analyzed its purity 98.4%.Lower floor's solids is heated to 50 ℃, and fusing carefully adds sodium hydroxide (0.5 mole) in batches, and cooling is filtered, and ethyl imidazol(e) is reclaimed in underpressure distillation, gets 41.4 grams, the rate of recovery 85.0%.
Embodiment 4
Among the embodiment 1, drip the mixture of Methylimidazole (0.25 mole) and ethyl imidazol(e) (0.25 mole), obtain 79.7 gram dichloromethyl phenylsilanes, yield 83.6%, purity 97.8%.Lower floor's solids is heated to 50 ℃, and fusing carefully adds sodium hydroxide (0.5 mole) in batches, and cooling is filtered, and the mixture of Methylimidazole and ethyl imidazol(e) is reclaimed in underpressure distillation, gets 35.6 grams, the rate of recovery 80.1%.
Embodiment 5
In 500 milliliters there-necked flask; add dimethyl dichlorosilane (DMCS) (0.5 mole) and chlorobenzene (0.5 mole); under the nitrogen protection; drip normal-butyl imidazoles (0.5 mole) by dropping funnel; dropwised in about 1 hour; slowly be warming up to 85 ℃; stirring reaction 5 hours leaves standstill, and is cooled to room temperature; lower floor has solid to separate out; decanting process is told the upper strata product, and 80～85 ℃/1.33kPa cut is collected in underpressure distillation, obtains 75.6 gram dichloromethyl phenylsilanes; yield 79.2%, GC-MS are analyzed its purity 98.7%.Lower floor's solids is heated to 50 ℃, and fusing carefully adds sodium hydroxide (0.5 mole) in batches, and cooling is filtered, and the normal-butyl imidazoles is reclaimed in underpressure distillation, gets 52.7 grams, the rate of recovery 85.0%.
Embodiment 6
In 500 milliliters there-necked flask; add dimethyl dichlorosilane (DMCS) (0.5 mole) and chlorobenzene (0.5 mole); under the nitrogen protection; drip n-octyl imidazoles (0.5 mole) by dropping funnel; dropwised in about 1 hour; slowly be warming up to 90 ℃, stirring reaction 5 hours leaves standstill; be cooled to room temperature; layering, lower floor is an oily matter, decanting process is told the upper strata product; 80～85 ℃/1.33kPa cut is collected in underpressure distillation; obtain 71.3 gram dichloromethyl phenylsilanes, yield 74.7%, GC-MS are analyzed its purity 98.3%.Layer oily matter is heated to 50 ℃, carefully adds sodium hydroxide (0.5 mole) in batches, and cooling is filtered, and the n-octyl imidazoles is reclaimed in underpressure distillation, gets 72 grams, the rate of recovery 80.0%.
Claims (10)
1, a kind of synthetic method of dichloromethyl phenylsilane, it is characterized in that with dimethyl dichlorosilane (DMCS) and chlorobenzene be raw material, in building-up process, utilize alkyl imidazole as acid binding agent, the alkyl imidazole hydrochloride that generates under molten state as reaction medium, heated and stirred is fully reacted, decanting process is told the upper strata product, and cut is collected in underpressure distillation, obtains the product dichloromethyl phenylsilane.
2, synthetic method according to claim 1 is characterized in that described stirring reaction 70～90 ℃ of following stirring reactions 4～6 hours, collects 80～85 ℃/1.33kPa cut, obtains the product dichloromethyl phenylsilane.
3, synthetic method according to claim 1 and 2 is characterized in that described alkyl imidazole is one or more the mixture in methyl, ethyl, normal-butyl, n-hexyl, n-octyl, positive decyl and the dodecyl imidazoles.
4, synthetic method according to claim 1 and 2, it is characterized in that described raw material thing dimethyl dichlorosilane (DMCS): chlorobenzene: the mol ratio of alkyl imidazole is 1: 1～1.2: 1～1.2.
5, synthetic method according to claim 3, it is characterized in that described raw material thing dimethyl dichlorosilane (DMCS): chlorobenzene: the mol ratio of alkyl imidazole is 1: 1～1.2: 1～1.2.
6, synthetic method according to claim 3, it is characterized in that described raw material thing dimethyl dichlorosilane (DMCS): chlorobenzene: the mol ratio of alkyl imidazole is 1: 1: 1.
7, synthetic method according to claim 5, it is characterized in that described raw material thing dimethyl dichlorosilane (DMCS): chlorobenzene: the mol ratio of alkyl imidazole is 1: 1: 1.
8, synthetic method according to claim 1 and 2 is characterized in that in described alkyl imidazole hydrochloride and the alkali and the recovery alkyl imidazole.
9, synthetic method according to claim 3 is characterized in that in described alkyl imidazole hydrochloride and the alkali and the recovery alkyl imidazole.
10, synthetic method according to claim 4 is characterized in that in described alkyl imidazole hydrochloride and the alkali and the recovery alkyl imidazole.
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| CNB2005100612668A CN100357299C (en) | 2005-10-26 | 2005-10-26 | Methylphenyldichlor disilane synthesis method |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102584882A (en) * | 2012-02-17 | 2012-07-18 | 嘉兴学院 | Method for preparing methyl phenyl dichlorosilane |
| CN108690198A (en) * | 2018-05-15 | 2018-10-23 | 杭州师范大学 | A kind of method that three (pentafluorophenyl group) borine catalysis prepare methyl phenyl silicone oil |
| CN114181244A (en) * | 2021-12-28 | 2022-03-15 | 宁夏中星显示材料有限公司 | Preparation method of alkyl siloxy halogenated benzene |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU530883A1 (en) * | 1975-03-19 | 1976-10-05 | Предприятие П/Я Г-4236 | Method for preparing phenylchlorosilanes |
| RU2079501C1 (en) * | 1995-07-03 | 1997-05-20 | Акционерное общество открытого типа "Химпром" | Method for production of methyl phenyl dichlorosilane |
-
2005
- 2005-10-26 CN CNB2005100612668A patent/CN100357299C/en active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102584882A (en) * | 2012-02-17 | 2012-07-18 | 嘉兴学院 | Method for preparing methyl phenyl dichlorosilane |
| CN102584882B (en) * | 2012-02-17 | 2014-07-09 | 嘉兴学院 | Method for preparing methyl phenyl dichlorosilane |
| CN108690198A (en) * | 2018-05-15 | 2018-10-23 | 杭州师范大学 | A kind of method that three (pentafluorophenyl group) borine catalysis prepare methyl phenyl silicone oil |
| CN108690198B (en) * | 2018-05-15 | 2021-01-15 | 杭州师范大学 | Method for preparing methyl phenyl silicone oil by catalyzing tris (pentafluorophenyl) borane |
| CN114181244A (en) * | 2021-12-28 | 2022-03-15 | 宁夏中星显示材料有限公司 | Preparation method of alkyl siloxy halogenated benzene |
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| Publication number | Publication date |
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