CN1312160C - Preparation method of allyl silane - Google Patents
Preparation method of allyl silane Download PDFInfo
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- CN1312160C CN1312160C CNB2005100401455A CN200510040145A CN1312160C CN 1312160 C CN1312160 C CN 1312160C CN B2005100401455 A CNB2005100401455 A CN B2005100401455A CN 200510040145 A CN200510040145 A CN 200510040145A CN 1312160 C CN1312160 C CN 1312160C
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- allyl
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- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- DNAJDTIOMGISDS-UHFFFAOYSA-N prop-2-enylsilane Chemical compound [SiH3]CC=C DNAJDTIOMGISDS-UHFFFAOYSA-N 0.000 title abstract 2
- -1 allyl halohydrocarbon Chemical class 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 150000002170 ethers Chemical class 0.000 claims abstract description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000007818 Grignard reagent Substances 0.000 claims abstract description 11
- 150000004795 grignard reagents Chemical class 0.000 claims abstract description 11
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 11
- 239000012046 mixed solvent Substances 0.000 claims abstract description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000007788 liquid Substances 0.000 claims abstract description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- 150000004756 silanes Chemical class 0.000 claims description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 239000005049 silicon tetrachloride Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- CRXNJSWBRJXDTE-UHFFFAOYSA-N Cl[SiH2]Cl.CC=C Chemical compound Cl[SiH2]Cl.CC=C CRXNJSWBRJXDTE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 claims description 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 8
- 238000003747 Grignard reaction Methods 0.000 abstract description 4
- 238000001035 drying Methods 0.000 abstract description 2
- 239000012044 organic layer Substances 0.000 abstract description 2
- 239000011259 mixed solution Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 4
- 229910018540 Si C Inorganic materials 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 229910010271 silicon carbide Inorganic materials 0.000 description 3
- 229910003902 SiCl 4 Inorganic materials 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical group BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- 229920000736 dendritic polymer Polymers 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- IKXDEFIEGAVNOZ-UHFFFAOYSA-N [SiH4].[C] Chemical compound [SiH4].[C] IKXDEFIEGAVNOZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 229920001558 organosilicon polymer Polymers 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention relates to a preparation method of allyl silane, which comprises the steps of dissolving allyl halohydrocarbon in mixed solvent of ethers and hydrocarbons, reacting with magnesium powder in a dropwise manner, adding mixed solution of ethers and hydrocarbons of the halosilane in a dropwise manner after the reaction starts, adding saturated ammonium chloride solution after the reaction is finished, adjusting the feed liquid to be neutral, separating out an organic layer, drying, and distilling under reduced pressure to obtain the product. The invention can continuously complete the preparation of the Grignard reagent and the Grignard reaction in one step, simplifies the operation process, adopts the mixed solvent of hydrocarbons and ethers, reduces the ether dosage, not only reduces the cost, but also ensures that the reaction process is safer.
Description
Technical field
The present invention relates to the preparation method of allyl silicane.
Background technology
Allyl silicane is a kind of special organosilane monomer, its Si-C bond rupture can be 306kj/mol, and is close with the energy-to-break 345kj/mol of C-C key, and the Si-C bond polarity is very low, therefore the kinetics of carbon silane and thermodynamic property are stable, are the raw materials of industrial preparation silicone rubber.In addition, the two keys of end group can be modified by addition reaction of silicon with hydrogen, prepare a series of different organosilicon polymers.Along with the development of dendritic polymer, stable Si-C makes its core element that becomes silicon class dendritic polymer, has also obtained a large amount of application.
The general preparation process of allyl silicane comprises two-step reaction, promptly at first prepare the intermediate Grignard reagent, and then make product, complex process with the chlorine-containing silane reaction, and preparation Grignard reagent solvent commonly used is ether or tetrahydrofuran (THF), the two is ether solvent, and toxicity is big, and boiling point is low, inflammable, price is more expensive, has buried hidden danger not only for the industrial applications of Grignard reagent, has also limited the scale operation of allyl silicane.Though the report that adopts ethers and hydro carbons mixed solvent to prepare Grignard reagent is also arranged, but A.Tuulmets etc. in " J.Organometal.Chem.1996; (523): 133-138 ", point out allyl halide for hydrocarbon because military kind coupled reaction easily takes place, can not in this mixed solvent, carry out the preparation of this type of Grignard reagent.
Summary of the invention
The purpose of this invention is to provide a kind of preparation method who contains a plurality of allyl silicanes, reduce the consumption of ether solvent, reduce cost, make whole process of preparation more simple and safe.
The allyl silicane that the present invention relates to contains following general formula:
Preparation process comprises following reaction formula:
In the formula: R is methyl, phenyl or vinyl,
N is 0～2,
X is Br or Cl;
As follows:
1. MAGNESIUM METAL and toluene or dimethylbenzene are mixed into suspension;
2. the allyl group halohydrocarbon is dissolved in ethers and the hydro carbons mixed solvent, is mixed with solution; The mol ratio of ethers and varsol is 0.05～4: 1;
3. halogenated silanes RnSiX4-n is dissolved in ethers and the varsol wiring solution-forming;
4. the allyl group halohydrocarbon solution of 2. step being prepared adds in the step magnesium suspension 1. in the mode that drips, and reacts under stirring and the backflow;
5. treat step 4. react begin to cause after, continue to drip the allyl group halohydrocarbon solution, and in feed liquid, add step halogenated silanes solution 3. in the mode that drips simultaneously, the continuation back flow reaction, temperature of reaction is 25 ℃～70 ℃;
6. after step reaction 5. finishes, stop to drip, feed liquid backflow 24h～70h is chilled to room temperature;
7. add the unreacted Grignard reagent of saturated ammonium chloride solution hydrolysis, isolate organic layer, dry back underpressure distillation gets allyl silicane.
Said ethers is ether or tetrahydrofuran (THF), and first-selection is a tetrahydrofuran (THF), and said hydro carbons is toluene or dimethylbenzene;
Constantly remove reaction by ice-water bath in the above-mentioned reaction process and generate heat, in the reaction process with inert nitrogen gas, argon gas or helium as protection gas.
Said allyl group halohydrocarbon is (1～1.5) * (4-n) with the mol ratio that contains halo silane RnSiX4-n: 1.
Selectable halogenated silanes has silicon tetrachloride, methyl trichlorosilicane, dimethyldichlorosilane(DMCS), phenylmethyldichloroislane, vinyl trichlorosilicane, methyl ethylene dichlorosilane.
In sum, timely and the halogenated silanes monomer reaction of the Grignard reagent that the present invention adopts the dropping mode that reaction is generated, reduce its concentration in solvent, reduce the chance of Wustz-reaction to greatest extent, impel reaction to carry out to the direction that generates final product, thereby reach the purpose of finishing with grignard reaction process continuous one-step of making that makes Grignard reagent, simplified operating process.The present invention adopts and to cause the method that grignard reaction drips chlorosilane more simultaneously earlier when improving the varsol consumption greatly, has avoided when hydro carbons and ethers ratio are excessive, and reaction process is difficult to the shortcoming that causes usually.The present invention adopts hydro carbons and ethers mixed solvent, has reduced the ethers consumption, makes reaction process safer, and has improved the productive rate that carries out grignard reaction in the mixed solvent.The allyl silicane that makes has a plurality of terminal double links, and very strong reactive behavior is arranged, and has purposes widely in fields such as silicon rubber, catalysis.
The invention will be further described below by example, but do not limit protection scope of the present invention.
Specific implementation method
Embodiment
Reaction unit is the four-hole boiling flask of 500mL, configuration constant pressure funnel and spherical condensation tube, drying nitrogen purge and protection under, an amount of magnesium powder of packing into, stir ten surplus minute, use a small amount of iodo activation.200mL toluene and an amount of tetrahydrofuran (THF) are mixed, again the 3-bromopropylene is mixed with it; To be dissolved with 9.3g SiCl
4The 10mL tetrahydrofuran (THF) add in the constant pressure funnel.The reaction beginning drips a small amount of 3-bromopropylene solution earlier, and the water-bath cooling causes the Grignard reagent preparation feedback down, drips silicon tetrachloride SiCl
4Solution keeps certain rate of addition to make reaction solution keep refluxing.Insulation was 50 ℃ after reaction finished, and refluxed 60 hours.After the question response thing is chilled to room temperature, in condition of ice bath downhill reaction bottle, drips an amount of saturated ammonium chloride solution and regulate pH till the neutrality.Add an amount of varsol to reactant, collect upper strata oily matter, dry back underpressure distillation, steaming desolventizes, and collects 71-72 ℃/4mmHg cut, gets the tetrapropylene base silane liquid that water white transparency has off-odor.
The structure detection data of products therefrom are as follows:
1H?NMR(CDCl
3，400MHz)：
δ＝1.59(8H，CH
2-)，4.86(8H，＝CH
2)，5.75(4H，-CH＝)；MS：
m/e(％)＝192(M，192)；
IR (liquid-film method):
Absorption peak is CH
2=CH-CH
2-(3150cm
-1, 2980cm
-1, 2880cm
-1, 1650cm
-1, 1450cm
-1, 960cm
-1) characteristic frequency.
Claims (5)
1. the preparation method of allyl silicane, said allyl silicane structural formula is:
, R wherein: methyl, phenyl or vinyl, n:0～2,
It is characterized in that as follows:
Code name X in each step is: Br or Cl;
1. metal magnesium powder and toluene or dimethylbenzene are mixed into suspension;
2. with the allyl group halohydrocarbon
Be dissolved in ethers and the hydro carbons mixed solvent, be mixed with solution; The mol ratio of ethers and varsol is 0.05～4: 1;
3. with halogenated silanes R
nSiX4-n is dissolved in ethers and the varsol, wiring solution-forming;
4. the allyl group halohydrocarbon of 2. step being prepared
Solution adds in the step magnesium suspension 1. in the mode that drips, and reacts under stirring and the backflow;
5. treat step 4. react begin to cause after, continue to drip the allyl group halohydrocarbon
Solution, and in feed liquid, add step halogenated silanes solution 3. in the mode that drips simultaneously, continuing back flow reaction, temperature of reaction is 25 ℃～70 ℃;
6. after step reaction 5. finishes, stop to drip, feed liquid backflow 24h～70h is chilled to room temperature;
7. add the unreacted Grignard reagent of saturated ammonium chloride solution hydrolysis, isolate oil reservoir, add siccative in the oil reservoir and remove moisture, remove by filter siccative, underpressure distillation gets the product allyl silicane after steaming and desolventizing;
Said ethers is ether or tetrahydrofuran (THF), and said hydro carbons is toluene or dimethylbenzene.
2. the preparation method of allyl silicane according to claim 1 is characterized in that regulating the allyl group halohydrocarbon
The rate of addition of solution and halogenated silanes RnSiX4-n solution is (1～1.5) * (4-n) with the mol ratio that reaches allyl group halohydrocarbon and RnSiX4-n: 1 proportionlity.
3. the preparation method of allyl silicane according to claim 2 is characterized in that in the reaction process with inert nitrogen gas, argon gas or helium as protection gas.
4. the preparation method of allyl silicane according to claim 3 is characterized in that adding in the 1. said magnesium powder of step a small amount of iodine and activates.
5. the preparation method of allyl silicane as claimed in claim 1 is characterized in that said halogenated silanes has silicon tetrachloride, methyl trichlorosilicane, dimethyldichlorosilane(DMCS), phenylmethyldichloroislane, vinyl trichlorosilicane, methyl ethylene dichlorosilane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100401455A CN1312160C (en) | 2005-05-23 | 2005-05-23 | Preparation method of allyl silane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100401455A CN1312160C (en) | 2005-05-23 | 2005-05-23 | Preparation method of allyl silane |
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| CN1702072A CN1702072A (en) | 2005-11-30 |
| CN1312160C true CN1312160C (en) | 2007-04-25 |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100366661C (en) * | 2006-02-17 | 2008-02-06 | 浙江大学 | Synthesis method of silicane coupling agent having long chain polyether chain section |
| CN103588805B (en) * | 2013-11-13 | 2016-04-06 | 大连九信生物化工科技有限公司 | A kind of synthetic method of diisopropyl chlorosilane |
| JP7007555B2 (en) * | 2016-09-27 | 2022-02-10 | セントラル硝子株式会社 | Purification method and production method of unsaturated bond-containing silane compound |
| JP6988772B2 (en) * | 2018-11-14 | 2022-01-05 | 信越化学工業株式会社 | Method for producing tetraalkenylsilane |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5596120A (en) * | 1995-10-23 | 1997-01-21 | Dow Corning Corporation | Process for preparation of organosilanes |
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- 2005-05-23 CN CNB2005100401455A patent/CN1312160C/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5596120A (en) * | 1995-10-23 | 1997-01-21 | Dow Corning Corporation | Process for preparation of organosilanes |
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