CN102898459A - Preparation method of diethyldimethoxysilane - Google Patents

Preparation method of diethyldimethoxysilane Download PDF

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CN102898459A
CN102898459A CN2012102220702A CN201210222070A CN102898459A CN 102898459 A CN102898459 A CN 102898459A CN 2012102220702 A CN2012102220702 A CN 2012102220702A CN 201210222070 A CN201210222070 A CN 201210222070A CN 102898459 A CN102898459 A CN 102898459A
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preparation
sodium
dimethoxy silane
monobromethane
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CN102898459B (en
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伍川
武侠
董红
蒋剑雄
曹健
程大海
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Shandong Baolongda New Materials Co ltd
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Hangzhou Normal University
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Abstract

The invention relates to the field of organic chemistry and provides a preparation method of diethyldimethoxysilane. The preparation method solves the problem that alcoholysis method-based synthesis of diethyldimethoxysilane has defects in safety and cost. The preparation method comprises that the diethyldimethoxysilane is synthesized from ethyltrimethoxysilane and bromoethane as raw materials by a sodium condensation method. The preparation method improves reaction controllability, allows mild reaction conditions, has simple processes, realizes good selectivity of diethyldimethoxysilane in a synthesized mixture, has a high yield and is suitable for large-scale industrial production.

Description

A kind of preparation method of diethyl dimethoxy silane
Technical field
The present invention relates to organic chemistry filed, specifically a kind of synthetic method that contains the compound diethyl dimethoxy silane of element silicon.
Background technology
Diethyl dimethoxy silane is a kind of important synthon, its character is more active, be used for synthesizing organo-silicon intermediate and high molecular polymer, also can be used as the constitution controller of silicon rubber, can be used as in addition good external electron donor in synthetic polypropylene (PP) catalyst system, in activity and the stereoselective while of improving catalyzer, improve the over-all properties of PP.
Field, people (Field, the Leslie D. such as Leslie D; Messerle, Barbara A.; Rehr, Manuela; Soler, Linnea P.; Hambley, Trevor W. Cationic Iridium (I) Complexes as Catalysts for the Alcoholysis of Silanes. Organometallics, 2003,22 (12): 2387-2395) with diethylsilane (Et 2SiH 2) and methyl alcohol as raw material, [Ir (BPM) is (CO) 2] +(BPh 4) -As catalyzer, tetrahydrofuran (THF) (THF) is as solvent, carries out alcoholysis reaction air atmosphere and 40 ℃, obtains diethyl dimethoxy silane (Et 2Si (OMe) 2) content is 80% synthetic product.People (Nagai, the Yoichiro such as Nagai Yoichiro; Ojima, Iwao; Kogure, Tetsuo. Jpn. Kokai Tokkyo Koho, JP 1974-42615 A, 19740422) with Et 2SiH 2With methyl alcohol be raw material, (Ph 3P) 3RhCl is catalyzer, reacts in ice-water bath, obtains Et 2Si (OMe) 2Content is 99% synthetic product.But adopt alcoholysis reaction technique to prepare Et 2Si (OMe) 2The time, not only use inflammable Et 2SiH 2As raw material, and also need use expensive Ir or Rh metal complex as catalyzer in the reaction process, reaction process exists potential safety hazard and cost higher.
Except alcoholysis reaction, prepared by sodium condensation method (Wurtz reaction) also can be used for preparing Et 2Si (OMe) 2, it is take ethyl trimethoxy silane and monobromethane as raw material, by generate diethyl dimethoxy silane under the sodium Metal 99.5 condensation.With the raw materials used Et of alcoholysis method 2SiH 2Compare, ethyl trimethoxy silane is more stable and safer; On the other hand, sodium mediated condensated reaction does not use the metal such as expensive Ir or Rh and complex compound thereof as catalyzer, has the advantage on the cost.But in the sodium mediated condensated reaction process, if reaction process control is improper, also may generate triethyl methoxy silane by product.The atmospheric boiling point of diethyl dimethoxy silane is 130 ℃, and (P1592-1594), the atmospheric boiling point of triethyl methoxy silane is 141 ℃ of (Mironov, I. V. for Emeleus, H. J. Journal of the Chemical Society 1947; Zhurnal Obshchei Khimii 1981, V51 (12), P2700-2704), both boiling points are more approaching, when adopting rectificating method to carry out separating-purifying, have certain difficulty.
Summary of the invention
For solving the safety that faces in the synthetic diethyl dimethoxy silane of alcoholysis method and the problem of cost aspect, the present invention proposes a kind of preparation method of diethyl dimethoxy silane, and present method has improved the controllability of reaction, and reaction conditions is gentle, and technique is simple; The content of diethyl dimethoxy silane is higher in the synthetic mixture, is suitable for large-scale commercial production.
The present invention is achieved by the following technical solutions: a kind of preparation method of diethyl dimethoxy silane, described diethyl dimethoxy silane is take ethyl trimethoxy silane and monobromethane as raw material, make by prepared by sodium condensation method, the structural formula of diethyl dimethoxy silane is:
Figure 905758DEST_PATH_IMAGE001
Reaction equation of the present invention is shown below:
Figure 31715DEST_PATH_IMAGE002
A kind of preparation method of diethyl dimethoxy silane, described preparation method carries out as follows:
1) ethyl trimethoxy silane and toluene are joined in the container, stir and to be warming up to 90 ~ 115 ℃, as preferably, temperature is 103 ~ 115 ℃; Continuing to add the sodium sheet under the agitation condition, and the sodium sheet is being broken into sodium sand, as preferably, the sodium sheet of newly cutting is being broken into sodium sand under mechanical agitation;
2) monobromethane is joined in the reaction system by bottom insert canal, hierarchy of control temperature is between 101 ~ 115 ℃, the monobromethane feed time is 1.0 ~ 6.0h, dropwises rear maintenance reaction mixture refluxed, continues reaction 0.1 ~ 6.0h after dropwising under reflux state; As preferably, the feed time of monobromethane is 1.5 ~ 3.5h, and the continuation reaction times is 1 ~ 5h; Monobromethane is vaporized under temperature of reaction after entering reaction system by bottom insert canal, carries out gas liquid reaction with ethyl trimethoxy silane in the liquid phase; If do not adopt the dropping mode monobromethane to be added drop-wise in the reaction system of heat by bottom insert canal, monobromethane one touches the material of heat and namely vaporizes, reaction is to carry out on the ethyl trimethoxy silane surface, causing most of monobromethane just not yet to react vaporizes, leave reaction system with vapor form, target product diethyl dimethoxy silane yield is low, and the monobromethane waste is serious, so monobromethane must adopt bottom insert canal reinforced.
3) with step 2) reaction product that obtains is cooled to 0 ~ 50 ℃, and as preferably, temperature is 15 ~ 40 ℃, drips ethanol under this temperature; The consumption that adds the ratio-dependent ethanol of 0.1 ~ 0.2 mol ethanol according to every mole metal sodium; Drip again dimethyldichlorosilane(DMCS), the consumption that adds the ratio-dependent dimethyldichlorosilane(DMCS) of 0.1 ~ 0.3 mol dimethyldichlorosilane(DMCS) according to every mole metal sodium, the time for adding of dimethyldichlorosilane(DMCS) is 0.5 ~ 4h, after dimethyldichlorosilane(DMCS) dropwises, reacts the 1 ~ 8h that holds time; As preferably, the time for adding of dimethyldichlorosilane(DMCS) is 1.5 ~ 3.5h; It is 1 ~ 6h that reaction is held time.Then adopt the decompress filter mode to remove solid impurity in the reaction mixture, collect simultaneously filtrate, filtrate being comprises the mixing solutions of target product diethyl dimethoxy silane of the present invention, adopt the known rectifying of chemical field or rectification under vacuum etc. to separate method of purification, to obtaining diethyl dimethoxy silane behind the further separating-purifying of filtrate.The ethanol that drips some amount is for the excessive sodium Metal 99.5 that neutralizes, keep the reaction certain hour after, dripping a certain amount of methyl chlorosilane is the sodium alkoxide that generates in order to neutralize again; As preferably, ethanol is selected from dehydrated alcohol.
Described toluene consumption is 0 ~ 0.6:1 with the ratio of the amount of substance of ethyl trimethoxy silane consumption; Described ethyl trimethoxy silane consumption is 1.0 ~ 6.0:1 with the ratio of the amount of substance of monobromethane consumption, and the consumption of sodium is 1.5 ~ 2.5:1 with the ratio of the amount of substance of monobromethane consumption; As preferably, the molar ratio of the consumption of described ethyl trimethoxy silane and monobromethane consumption is 2.9 ~ 5.0:1; The consumption of sodium is 1.9 ~ 2.3:1 with the ratio of the amount of substance of monobromethane consumption; The ratio of amount of substance of the present invention is mol ratio.
The present invention prepares a kind of diethyl dimethoxy silane take ethyl trimethoxy silane and monobromethane as raw material by prepared by sodium condensation method, and by feed change proportioning, feed time, temperature of reaction, the parameters such as solvent load further improve target product yield.In the synthetic diethyl dimethoxy silane of prepared by sodium condensation method, with toluene as solvent, with ethyl trimethoxy silane as reaction raw materials, sodium Metal 99.5 is dispersed in the ethyl trimethoxy silane, form sodium sand, then with monobromethane generation condensation reaction, obtain containing the synthetic crude product of diethyl dimethoxy silane, synthetic crude product is collected filtrate through known solid-liquid separating method, and filtrate is the separable diethyl dimethoxy silane that obtains through liquid liquid separating methods such as known rectifying again.
Compared with prior art, the invention has the beneficial effects as follows:
(1) reaction conditions is gentle, and technique is simple;
(2) the present invention has overcome the low shortcoming of generation one substitution product selectivity in the conventional sodium mediated condensated reaction, by adjusting feed way and the feed rate of proportioning raw materials, monobromethane, suppress the generation of two substitution products, the synthetic product that is not contained the triethyl methoxy silane has improved the controllability of reaction.
(3) selectivity of diethyl dimethoxy silane is good in the synthetic mixture, and yield is higher, is very suitable for large-scale commercial production.
Embodiment
Below in conjunction with embodiment the present invention is described in further detail, but embodiment not limiting the scope of the invention that used raw material is commercial product among the embodiment.
Embodiment 1
In the dry 250mL four-hole boiling flask of reflux condensing tube, mechanical stirrer and Pt-100 RTD is housed, add 20g(0.2171 mol) toluene, 119.8g(0.7973 mol) ethyl trimethoxy silane, under agitation add 12.7g(0.5524 mol) the sodium sheet newly cut, be warming up to 109 ℃, the sodium sheet is broken into sodium sand; In 3.5h, with 29.5g(0.2707 mol) monobromethane adds in the reaction system by bottom insert canal, the control temperature of reaction is between 107 ~ 111 ℃, under reflux state, continue reaction 3.5h after dropwising, to be cooled after 18.4 ℃, slowly add 5.0mL(0.0857 mol) in the ethanol and excessive sodium Metal 99.5; Then with 8.7g(0.0674 mol) dimethyldichlorosilane(DMCS) is added drop-wise in 1.5h in the mixture, the sodium alkoxide that generates with neutralization; After dropwising, under this temperature, continue again reaction 3h.Then with the reaction mixture decompress filter, obtain containing mixture 98.8 g that dimethyldiethoxysilane, diethyl dimethoxy silane, ethyl trimethoxy silane and a small amount of polycondensation product and toluene form.Filtrate adopts GC-MS to analyze (area normalization method), and diethyl dimethoxy silane massfraction is 19.31%, and triethyl methoxy silane mark is 0%, and selectivity is 100%, and diethyl dimethoxy silane yield is 47.53%.。
Embodiment 2
In the dry 500mL four-hole boiling flask of reflux condensing tube, mechanical stirrer and Pt-100 RTD is housed, add 20g(0.2171 mol) toluene, 159.8g(1.0636 mol) ethyl trimethoxy silane, under agitation add 12.0g(0.5220 mol) the sodium sheet newly cut, be warming up to 103 ℃, the sodium sheet is broken into sodium sand; In 2.5h, with 29.8g(0.2734mol) monobromethane adds in the reaction system by bottom insert canal, the control temperature of reaction is between 101 ~ 105 ℃, under reflux state, continue reaction 2.5h after dropwising, to be cooled after 38 ℃, slowly add 4.0mL(0.0685 mol) in the ethanol and excessive sodium Metal 99.5; Then with 7.8g(0.0604 mol) dimethyldichlorosilane(DMCS) is added drop-wise in 2.5h in the mixture, the sodium alkoxide that generates with neutralization; After dropwising, under this temperature, continue again reaction 2h.Then with the reaction mixture decompress filter, obtain containing the mixture 107.3g that dimethyldiethoxysilane, diethyl dimethoxy silane, ethyl trimethoxy silane, toluene and a small amount of polycondensation product form.Filtrate adopts GC-MS to analyze (area normalization method), and diethyl dimethoxy-methyl silane massfraction is 18.71%, and triethyl methoxy silane 0%, selectivity are 100%, and diethyl dimethoxy silane yield is 49.50%.。
Embodiment 3
In the dry 500mL four-hole boiling flask of reflux condensing tube, mechanical stirrer and Pt-100 RTD is housed, add 199.6g(1.3285 mol) ethyl trimethoxy silane, under agitation add 12.4g(0.5394 mol) the sodium sheet newly cut, be warming up to 103 ℃, the sodium sheet is broken into sodium sand; In 2.5h, with 29.1g(0.2671 mol) monobromethane adds in the reaction system by bottom insert canal, the control temperature of reaction is between 107 ~ 111 ℃, under reflux state, continue reaction 5 h after dropwising, to be cooled after 40 ℃, slowly add 6.0mL(0.1028 mol) in the ethanol and excessive sodium Metal 99.5; Then with 20.0g(0.1550 mol) dimethyldichlorosilane(DMCS) is added drop-wise in 3.5h in the mixture, the sodium alkoxide that generates with neutralization; After dropwising, under this temperature, continue again reaction 1h.Then with the reaction mixture decompress filter, obtain containing the mixture 118.9g that dimethyldiethoxysilane, diethyl dimethoxy silane, ethyl trimethoxy silane, toluene and a small amount of polycondensation product form.Filtrate adopts GC-MS to analyze (area normalization method), and diethyl dimethoxy silane massfraction is 20.71%, and triethyl methoxy silane massfraction is 0%, and selectivity is 100%, and diethyl dimethoxy silane yield is 62.17%.。
Embodiment 4
In the dry 500mL four-hole boiling flask of reflux condensing tube, mechanical stirrer and Pt-100 RTD is housed, add 40g(0.4341 mol) toluene, 159.8g(1.0636 mol) ethyl trimethoxy silane, under agitation add 13.0g(0.5655 mol) the sodium sheet newly cut, be warming up to 109 ℃, the sodium sheet is broken into sodium sand; In 1.5h, with 29.1g(0.2671 mol) monobromethane adds in the reaction system by bottom insert canal, the control temperature of reaction is between 107 ~ 111 ℃, under reflux state, continue reaction 1.5 h after dropwising, to be cooled after 32.6 ℃, slowly add 5mL(0.0857 mol) in the ethanol and excessive sodium Metal 99.5; Then with 15.1g(0.1170 mol) dimethyldichlorosilane(DMCS) is added drop-wise in 3.0h in the mixture, the sodium alkoxide that generates with neutralization; After dropwising, under this temperature, continue again reaction 4h.Then with the reaction mixture decompress filter, obtain containing dimethyldiethoxysilane, diethyl dimethoxy silane, ethyl trimethoxy silane and toluene, the mixture 120.9g that a small amount of polycondensation product forms.Filtrate adopts GC-MS to analyze (area normalization method), and diethyl dimethoxy silane massfraction is 17.23%, and the massfraction of triethyl methoxy silane is 0%, and selectivity is 100%, and diethyl dimethoxy silane yield is 52.60%.。
Embodiment 5
In the dry 250mL four-hole boiling flask of reflux condensing tube, mechanical stirrer and Pt-100 RTD is housed, add 40.1g(0.4352 mol) toluene, 119.7g(0.7967 mol) ethyl trimethoxy silane, under agitation add 13.5g(0.5872 mol) the sodium sheet newly cut, be warming up to 115 ℃, the sodium sheet is broken into sodium sand; In 2.5h, with 29.0g(0.2661 mol) monobromethane adds in the reaction system by bottom insert canal, the control temperature of reaction is between 113 ~ 115 ℃, under reflux state, continue reaction 2 h after dropwising, to be cooled after 35.8 ℃, slowly add 6.0mL(0.1028 mol) in the ethanol and excessive sodium Metal 99.5; Then with 7.9g(0.0612 mol) dimethyldichlorosilane(DMCS) is added drop-wise in 1.5h in the mixture, the sodium alkoxide that generates with neutralization; After dropwising, under this temperature, continue again reaction 6h.Then with the reaction mixture decompress filter, obtain containing dimethyldiethoxysilane, diethyl dimethoxy silane, ethyl trimethoxy silane and toluene, the mixture 112.3g that a small amount of polycondensation product forms.Filtrate adopts GC-MS to analyze (area normalization method), and diethyl dimethoxy silane massfraction is 20.26%, and triethyl methoxy silane massfraction is 0%, and selectivity is that 100% diethyl dimethoxy silane yield is 57.66%.

Claims (8)

1. the preparation method of a diethyl dimethoxy silane is characterized in that: described diethyl dimethoxy silane is made by prepared by sodium condensation method take ethyl trimethoxy silane and monobromethane as raw material, and the structural formula of diethyl dimethoxy silane is:
Figure 2012102220702100001DEST_PATH_IMAGE002
2. the preparation method of a kind of diethyl dimethoxy silane according to claim 1 is characterized in that, described preparation method carries out as follows:
1) ethyl trimethoxy silane and toluene are joined in the container, stir and be warming up to 90 ~ 115 ℃, under lasting agitation condition, add the sodium sheet and the sodium sheet is broken into sodium sand;
2) monobromethane is added in the reaction system by bottom insert canal, hierarchy of control temperature is between 101 ~ 115 ℃, and the feed time 1.0 ~ 6.0h of monobromethane continues reaction 0.1 ~ 6.0h under reflux state after dropwising;
3) with step 2) reaction product that obtains is cooled to 0 ~ 50 ℃, drip ethanol under this temperature, and then drip dimethyldichlorosilane(DMCS), the time for adding of dimethyldichlorosilane(DMCS) is 0.5 ~ 4.0h, after dimethyldichlorosilane(DMCS) dropwises, react the 1.0 ~ 8.0h that holds time; Then adopt the decompress filter mode to remove solid impurity in the reaction mixture, collect simultaneously filtrate, filtrate being comprises the mixing solutions of target product diethyl dimethoxy silane of the present invention;
Described toluene consumption is 0 ~ 0.6:1 with the ratio of the amount of substance of ethyl trimethoxy silane consumption; Described ethyl trimethoxy silane consumption is 1.0 ~ 6.0:1 with the ratio of the amount of substance of monobromethane consumption; The consumption of sodium is 1.5 ~ 2.5:1 with the ratio of the amount of substance of monobromethane consumption, add the consumption of the ratio-dependent ethanol of 0.1 ~ 0.2mol ethanol according to every mole metal sodium, add the consumption of the ratio-dependent dimethyldichlorosilane(DMCS) of 0.1 ~ 0.3mol chlorine atom according to every mole metal sodium.
3. the preparation method of diethyl dimethoxy silane according to claim 1 and 2, it is characterized in that: described ethyl trimethoxy silane consumption is 2.9 ~ 5.0:1 with the ratio of the amount of substance of monobromethane consumption; The consumption of sodium is 1.9 ~ 2.3:1 with the ratio of the amount of substance of monobromethane consumption.
4. the preparation method of diethyl dimethoxy silane according to claim 2 is characterized in that: stir in the step 1) and be warming up to 103 ~ 115 ℃.
5. the preparation method of diethyl dimethoxy silane according to claim 2 is characterized in that: step 2) described in the time for adding of monobromethane be 1.5 ~ 3.5h, keeping the reaction times is 1.0 ~ 5.0h.
6. the preparation method of diethyl dimethoxy silane according to claim 2 is characterized in that: drip ethanol in the step 3) under 15 ~ 45 ℃ of temperature.
7. according to claim 2 or the preparation method of 6 described diethyl dimethoxy silane, it is characterized in that: ethanol is selected from dehydrated alcohol.
8. the preparation method of diethyl dimethoxy silane according to claim 2, it is characterized in that: the time for adding of methyl chlorosilane is 1.5 ~ 3.5h; It is 1 ~ 6h that reaction is held time.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4500725A (en) * 1981-07-30 1985-02-19 Chisso Corporation Silane derivative and fragrant article
CN1532200A (en) * 2003-03-18 2004-09-29 武汉化工学院研究设计院 One-step synthesizing cyclohexyl methyl dimethoxy silane without solvent
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Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4500725A (en) * 1981-07-30 1985-02-19 Chisso Corporation Silane derivative and fragrant article
CN1532200A (en) * 2003-03-18 2004-09-29 武汉化工学院研究设计院 One-step synthesizing cyclohexyl methyl dimethoxy silane without solvent
CN102351894A (en) * 2011-09-22 2012-02-15 中蓝晨光化工研究设计院有限公司 Preparation method of methylphenyldialkoxysilane

Non-Patent Citations (3)

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Title
LESLIE D. FIELD等: "《Cationic Iridium(I) Complexes as Catalysts for the Alcoholysis of Silanes》", 《ORGANOMETALLICS》, vol. 22, no. 12, 7 May 2003 (2003-05-07), pages 2387 - 2395 *
张卫红等: "《格氏法合成甲基环己基二甲氧基硅烷的研究》", 《江苏石油化工学院学报》, vol. 14, no. 1, 25 March 2002 (2002-03-25), pages 1 - 3 *
钟桂云等: "《甲基二烯丙基乙氧基硅烷的合成》", 《化工新型材料》, vol. 34, no. 7, 30 July 2006 (2006-07-30) *

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