CN102898454A - M-methylphenyldiethoxymethylsilane and preparation method thereof - Google Patents
M-methylphenyldiethoxymethylsilane and preparation method thereof Download PDFInfo
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- CN102898454A CN102898454A CN2012100751961A CN201210075196A CN102898454A CN 102898454 A CN102898454 A CN 102898454A CN 2012100751961 A CN2012100751961 A CN 2012100751961A CN 201210075196 A CN201210075196 A CN 201210075196A CN 102898454 A CN102898454 A CN 102898454A
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Abstract
The invention relates to the field of organic silicon chemistry and discloses an m-methylphenyldiethoxymethylsilane and a preparation method thereof. The preparation method solves the problem that in the existing sodium condensation method-based synthesis of m-methylphenyldiethoxymethylsilane, a large amount of a solvent is used and thus environmental pollution is caused and solvent recycle is difficult. The m-methylphenyldiethoxymethylsilane is synthesized from methyltriethoxysilane and m-chlorotoluene as raw materials by a sodium condensation method. The preparation method does not use a toluene solvent, allows mild reaction conditions, has simple processes and is suitable for large-scale industrial production.
Description
Technical field
The present invention relates to the organosilicon chemical field, specifically aminomethyl phenyl diethoxymethyl silane and synthetic method thereof between a kind of compound that contains element silicon.
Background technology
Between the aminomethyl phenyl diethoxymethyl silane (an aminomethyl phenyl diethoxymethyl silane) that replaces of position be a kind of important synthon, its character is more active, can be used to the macromolecular compounds such as synthesizing organo-silicon intermediate and silicone oil, silicon rubber, because it has higher Lorentz-Lorenz molar refraction, can be used for improving the specific refractory power of organosilicon material, have important use in fields such as LED encapsulation, fiber waveguide device, light interconnect devices and optical lenses.
Utilize at present sodium contracting method synthetic between the research of the aminomethyl phenyl diethoxymethyl silane that replaces of position also be in the starting stage.Sodium contracting method is a kind of classical way that is built with at present organic silicon compound, namely utilize prepared by sodium condensation method the functional group of the high refractive index such as phenyl can be introduced in the organosilicon molecule, improve the specific refractory power of silicoorganic compound and derivative polymkeric substance thereof, improve the optical property of organosilicon product.But the prepared by sodium condensation method reaction process is a solid-liquid reaction process, must use a large amount of solvents (toluene etc.), could fully react with medium so that solid is dispersed in the reaction medium, and the solid content in the simultaneously reduction system can normally move so that stir.But, use in a large number toluene solvant can face the problem of environmental pollution and recycled solvent.
Summary of the invention
For solution utilize sodium contracting method synthetic between the position replace aminomethyl phenyl diethoxymethyl silane the time use a large amount of solvents can face the problem of environmental pollution and recycled solvent, the present invention proposes a kind of aminomethyl phenyl diethoxymethyl silane and synthetic method thereof, present method is not used the toluene equal solvent, reaction conditions is gentle, and technique is simple; Be very suitable for large-scale commercial production.
The present invention is achieved by the following technical solutions: a kind of aminomethyl phenyl diethoxymethyl silane, and described aminomethyl phenyl diethoxymethyl silane is made by prepared by sodium condensation method take Union carbide A-162 and m-chlorotoluene as raw material, and its structural formula is:
Reaction equation of the present invention is shown below:
The preparation method of a kind of aminomethyl phenyl diethoxymethyl silane, described preparation method carries out as follows:
1) Union carbide A-162 is joined in the container, stir and to be warming up to 90 ~ 112 ℃, as preferably, temperature is 102 ~ 105 ℃; Continuing to add the sodium sheet under the stirring, 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) drip m-chlorotoluene, keep reaction mixture refluxed and control temperature of reaction being lower than 112 ℃, time for adding is 0.5 ~ 10h, keeps reaction 0.1 ~ 20h after dropwising; As preferably, the time for adding of m-chlorotoluene is 1 ~ 6h, and keeping the reaction times is 2 ~ 10h;
3) reaction mixture is cooled to 0 ~ 50 ℃, as preferably, temperature is 15 ~ 35 ℃, drip ethanol under this temperature, the time for adding of ethanol is 0.05 ~ 2h, and keeps reaction 0.1 ~ 4h, as preferably, the ethanol time for adding is 0.1 ~ 1h, and it is 0.5 ~ 2h that reaction is held time; Drip methyl chlorosilane again, add the consumption of the ratio-dependent methyl chlorosilane of 0.2 ~ 0.4mol chlorine atom according to every mole metal sodium, the time for adding of methyl chlorosilane is 0.1 ~ 4h, after methyl chlorosilane dropwises, reacts the 1 ~ 8h that holds time; As preferably, the time for adding of methyl chlorosilane is 0.5 ~ 2h; It is 2 ~ 6h that reaction is held time.Then adopt the decompress filter mode to remove solid impurity in the reaction mixture, collect simultaneously filtrate; The ethanol that drips some amount in the step (3) 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;
4) to obtaining an aminomethyl phenyl diethoxymethyl silane behind the further separating-purifying of filtrate, generally adopt the known rectifying of chemical field or rectification under vacuum etc. to separate method of purification;
Described Union carbide A-162 consumption is 1.0 ~ 6.0:1 with the ratio of the amount of substance of m-chlorotoluene consumption, and as preferably, the molar ratio of the consumption of described Union carbide A-162 and m-chlorotoluene consumption is 1.5 ~ 4:1; The consumption of sodium is 1.9 ~ 2.5:1 with the ratio of the amount of substance of m-chlorotoluene consumption; As preferably, the consumption of sodium is 2.0 ~ 2.15:1 with the ratio of the amount of substance of m-chlorotoluene consumption, and the ratio of amount of substance described above is the molar mass ratio.
Described methyl chlorosilane is selected from METHYL TRICHLORO SILANE or dimethyldichlorosilane(DMCS), and as preferably, methyl chlorosilane is selected from METHYL TRICHLORO SILANE; Take the amount of substance of employed sodium Metal 99.5 as benchmark, the consumption that adds the ratio-dependent methyl chlorosilane of 0.2 ~ 0.4mol chlorine atom according to every mole metal sodium, when namely using METHYL TRICHLORO SILANE, its consumption (mole number) is 0.0667 ~ 0.1333 times of sodium Metal 99.5 amount of substance, when using dimethyldichlorosilane(DMCS), its consumption (mole number) is 0.1 ~ 0.2 times of sodium Metal 99.5 amount of substance;
The present invention is take Union carbide A-162 and m-chlorotoluene as raw material, by prepared by sodium condensation method prepare a kind of novel, do not reported between the aminomethyl phenyl diethoxymethyl silane [m-MePhMeSi (OEt) that replaces of position
2], by parameters such as feed change proportioning, feed rate, temperature of reaction, further improve target product yield.In the aminomethyl phenyl diethoxymethyl silane that the position replaces between prepared by sodium condensation method is synthetic, do not use the toluene equal solvent, directly with the Union carbide A-162 of one of reaction raw materials as solvent and reaction raw materials, sodium Metal 99.5 is dispersed in the Union carbide A-162, form sodium sand, then with m-chlorotoluene generation condensation reaction, obtain an aminomethyl phenyl diethoxymethyl silane.
Compared with prior art, the invention has the beneficial effects as follows:
(1) in the reaction process except reaction raw materials m-chlorotoluene and Union carbide A-162, do not use other solvent, reaction conditions is gentle, technique is simple;
(2) the present invention has overcome the traditional sodium condensation method and has been prepared with environmental pollution and the recycled solvent problem of using toluene solvant to face in the organic compounds technique, has effectively improved the conversion unit utilization ratio, has improved the transformation efficiency of stock yard toluene(mono)chloride;
(3) aminomethyl phenyl diethoxymethyl silane contents is high in the middle of the synthetic mixture, and aminomethyl phenyl diethoxymethyl silane separating-purifying is simple between target product, can significantly save process cost, is very suitable for large-scale commercial production.
Embodiment
Below in conjunction with embodiment the present invention is described in further detail, but embodiment is not limiting the scope of the invention, 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 the 100g(0.561 mole) Union carbide A-162, under agitation add the 18g(0.783 mole) the sodium sheet newly cut, be warming up to 102 ℃, the sodium sheet is broken into sodium sand; In 4h, with the 47g(0.371 mole) m-chlorotoluene is added drop-wise in the reaction system by constant pressure funnel, the control temperature of reaction is between 108 ~ 110 ℃, dropwise rear continuation and react 2 h, to be cooled after 25 ℃, in 0.5h, slowly add the 1.5g(0.0326 mole) in the dehydrated alcohol and excessive sodium Metal 99.5, under 25 ℃, keep 1h again after dropwising; Then with the 10mL(0.083 mole) dimethyldichlorosilane(DMCS) is added drop-wise in 1h 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 the filtrate 102g that aminomethyl phenyl diethoxymethyl silane, two (aminomethyl phenyl) (ethoxymethyl) base silane, dimethyldiethoxysilane, residual Union carbide A-162 and a small amount of polycondensation product form.Filtrate adopts GC-MS to analyze (area normalization method), between aminomethyl phenyl diethoxymethyl silane massfraction be 32.04 %, two (aminomethyl phenyl) (ethoxymethyl) base silane massfraction is 15.45 %, and the m-chlorotoluene transformation efficiency is 89.38%, and selectivity is 55.56%.
Air distillation is carried out rectification under vacuum after reclaiming dimethyldiethoxysilane and Union carbide A-162 again, obtain purity and be 97.45% between aminomethyl phenyl diethoxymethyl silane 30.2 g.
Embodiment 2
In the dry 1000mL four-hole boiling flask of reflux condensing tube, mechanical stirrer and Pt-100 RTD is housed, add the 450g(2.524 mole) Union carbide A-162, under agitation add the 58.2g(2.530 mole) the sodium sheet newly cut, be warming up to 105 ℃, the sodium sheet is broken into sodium sand; In 2h, with the 160g(1.264 mole) m-chlorotoluene is added drop-wise in the reaction system by constant pressure funnel, the control temperature of reaction is between 102 ~ 105 ℃, dropwise rear continuation and react 4 h, to be cooled after 30 ℃, in 1.0h, slowly add the 5.1g(0.111 mole) in the dehydrated alcohol and excessive sodium Metal 99.5, under 30 ℃, keep 1.5h again after dropwising; Then with the 30mL(0.257 mole) METHYL TRICHLORO SILANE is added drop-wise in 2h 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 the filtrate 478g that aminomethyl phenyl diethoxymethyl silane, two (aminomethyl phenyl) (ethoxymethyl) base silane, Union carbide A-162 and a small amount of polycondensation product form.Filtrate adopts GC-MS to analyze (area normalization method), between aminomethyl phenyl diethoxymethyl silane massfraction be 36.19 %, two (aminomethyl phenyl) (ethoxymethyl) base silane massfraction is 12.02 %, and the m-chlorotoluene transformation efficiency is 94.61%, and selectivity is 64.47%.
Air distillation is carried out rectification under vacuum after reclaiming Union carbide A-162 again, obtain purity and be 98.12% between aminomethyl phenyl diethoxymethyl silane 162.2 g.
Embodiment 3
In the dry 500mL four-hole boiling flask of reflux condensing tube, mechanical stirrer and Pt-100 RTD is housed, add the 253g(1.419 mole) Union carbide A-162, under agitation add the 21.8g(0.948 mole) the sodium sheet newly cut, be warming up to 104 ℃, the sodium sheet is broken into sodium sand; In 6h, with the 60g(0.474 mole) m-chlorotoluene is added drop-wise in the reaction system by constant pressure funnel, the control temperature of reaction is between 105 ~ 108 ℃, dropwise rear continuation and react 5 h, to be cooled after 20 ℃, in 1.0h, slowly add the 2.0g(0.043 mole) in the dehydrated alcohol and excessive sodium Metal 99.5, under 20 ℃, keep 1.5h again after dropwising; Then with the 13mL(0.108 mole) 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 2h.Then with the reaction mixture decompress filter, obtain containing the filtrate 266g that aminomethyl phenyl diethoxymethyl silane, two (aminomethyl phenyl) (ethoxymethyl) base silane, dimethyldiethoxysilane, unconverted Union carbide A-162 and a small amount of polycondensation product form.Filtrate adopts GC-MS to analyze (area normalization method), between aminomethyl phenyl diethoxymethyl silane massfraction be 25.33 %, two (aminomethyl phenyl) (ethoxymethyl) base silane massfraction is 7.61 %, and the m-chlorotoluene transformation efficiency is 94.93%, and selectivity is 66.73%.
Air distillation is carried out rectification under vacuum after reclaiming dimethyldiethoxysilane and Union carbide A-162 again, obtain purity and be 98.32% between aminomethyl phenyl diethoxymethyl silane 60g.
Embodiment 4
In the dry 500mL four-hole boiling flask of reflux condensing tube, mechanical stirrer and Pt-100 RTD is housed, add the 337g(1.890 mole) Union carbide A-162, under agitation add the 21.8g(0.948 mole) the sodium sheet newly cut, be warming up to 105 ℃, the sodium sheet is broken into sodium sand; In 4h, with the 60g(0.474 mole) m-chlorotoluene is added drop-wise in the reaction system by constant pressure funnel, the control temperature of reaction is between 102 ~ 104 ℃, dropwise rear continuation and react 2 h, to be cooled after 20 ℃, in 1.0h, slowly add the 2.0g(0.043 mole) in the dehydrated alcohol and excessive sodium Metal 99.5, under 20 ℃, keep 1.5h again after dropwising; Then with the 13mL(0.111 mole) METHYL TRICHLORO SILANE is added drop-wise in 2h 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 the filtrate 349g that aminomethyl phenyl diethoxymethyl silane, two (aminomethyl phenyl) (ethoxymethyl) base silane, Union carbide A-162 and a small amount of polycondensation product form.Filtrate adopts GC-MS to analyze (area normalization method), between aminomethyl phenyl diethoxymethyl silane massfraction be 21.61 %, two (aminomethyl phenyl) (ethoxymethyl) base silane massfraction is 4.51 %, and the m-chlorotoluene transformation efficiency is 95.47%, and selectivity is 74.28%.
Air distillation is carried out rectification under vacuum after reclaiming Union carbide A-162 again, obtain purity and be 97.69% between aminomethyl phenyl diethoxymethyl silane 68.7 g.
Interpretation of result
Get aminomethyl phenyl diethoxymethyl silane 4g between embodiment 4 gained, through column chromatography for separation, fill column layer chromatography silicone rubber in the chromatography column, take sherwood oil: ethyl acetate as the mixed solution of 5:1 as elutriant, obtain highly purified aminomethyl phenyl diethoxymethyl silane, respectively it is carried out FT-IR, GC-MS and reach
1H NMR reaches
13C NMR analyzes, to determine and to verify the structure of target compound.
The Spectrum Analysis result is as follows:
IR(KBr)ν:?2973（CH
3），1104?,1165(Si-OEt)，1257?(Si-Me)?,1478，1577，3023?(C
6H
4),?702（
）cm
-1；
GC/MS?m/z?(%):224(M
+,17),?209（100),?179(8),?133（13）；
1H-NMR(CDCl
3,400MHz)δ:1.301-1.335(t,3H,OCH
2CH
3)，
2.429(s,3H,?C
6H
4-CH
3),3.885-3.902(t,2H,?OCH
2CH
3),7.273-7.535(m,?H，C
6H
4)。
13C-NMR(CDCl
3,400MHz)δ:137.1，134.7，134.6，131.1，130.8，127.8，58.5，21.5，-4.8。
Claims (7)
1. aminomethyl phenyl diethoxymethyl silane between one kind is characterized in that: described aminomethyl phenyl diethoxymethyl silane is made by prepared by sodium condensation method take Union carbide A-162 and m-chlorotoluene as raw material, and its structural formula is:
2. the preparation method of aminomethyl phenyl diethoxymethyl silane between a kind is characterized in that, described preparation method carries out as follows:
1) Union carbide A-162 is joined in the container, stir and be warming up to 90 ~ 112 ℃, under lasting the stirring, add the sodium sheet and the sodium sheet is broken into sodium sand;
2) drip m-chlorotoluene, keep reaction mixture refluxed and control temperature of reaction being lower than 112 ℃, time for adding is 0.5 ~ 10h, keeps reaction 0.1 ~ 20h after dropwising;
3) reaction mixture is cooled to 0 ~ 50 ℃, under this temperature, drip ethanol, the time for adding of ethanol is 0.05 ~ 2h, and keep and react 0.1 ~ 4h, drip methyl chlorosilane again, add the consumption of the ratio-dependent methyl chlorosilane of 0.2 ~ 0.4mol chlorine atom according to every mole metal sodium, the time for adding of methyl chlorosilane is 0.1 ~ 4h, after methyl chlorosilane dropwises, react the 1 ~ 8h that holds time; Then adopt the decompress filter mode to remove solid impurity in the reaction mixture, collect simultaneously filtrate;
4) to obtaining an aminomethyl phenyl diethoxymethyl silane behind the further separating-purifying of filtrate;
Described Union carbide A-162 consumption is 1.0 ~ 6.0:1 with the ratio of the amount of substance of m-chlorotoluene consumption; The consumption of sodium is 1.9 ~ 2.5:1 with the ratio of the amount of substance of m-chlorotoluene consumption;
Described methyl chlorosilane is selected from METHYL TRICHLORO SILANE or dimethyldichlorosilane(DMCS).
3. the preparation method of according to claim 2 aminomethyl phenyl diethoxymethyl silane, it is characterized in that: described Union carbide A-162 consumption is 1.5 ~ 4:1 with the ratio of the amount of substance of m-chlorotoluene consumption; The consumption of sodium is 2.0 ~ 2.15:1 with the ratio of the amount of substance of m-chlorotoluene consumption.
4. the preparation method of according to claim 2 aminomethyl phenyl diethoxymethyl silane is characterized in that: stir in the step 1) and be warming up to 102 ~ 105 ℃.
5. according to claim 2 or the preparation method of 3 described aminomethyl phenyl diethoxymethyl silane, it is characterized in that: step 2) described in the time for adding of m-chlorotoluene be 1 ~ 6h, keeping the reaction times is 2 ~ 10h.
6. the preparation method of according to claim 2 aminomethyl phenyl diethoxymethyl silane, it is characterized in that: drip ethanol in the step 3) under 15 ~ 35 ℃ of temperature, the time for adding of ethanol is 0.1 ~ 1h, and keeps reaction 0.1 ~ 4h.
7. the preparation method of according to claim 2 aminomethyl phenyl diethoxymethyl silane, it is characterized in that: the time for adding of methyl chlorosilane is 0.5 ~ 2h; It is 2 ~ 6h that reaction is held time.
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Cited By (3)
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| CN103613609A (en) * | 2013-12-17 | 2014-03-05 | 佛山市华联有机硅有限公司 | Method for preparing dimethyl phenyl ethoxy silane |
| CN104610340A (en) * | 2015-01-27 | 2015-05-13 | 荆州市江汉精细化工有限公司 | Preparation method for dimethoxymethylphenylsilane |
| CN107915755A (en) * | 2017-11-03 | 2018-04-17 | 山东宝龙达实业集团有限公司 | A kind of Methylethyl diethoxy silane synthetic method |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103613609A (en) * | 2013-12-17 | 2014-03-05 | 佛山市华联有机硅有限公司 | Method for preparing dimethyl phenyl ethoxy silane |
| CN104610340A (en) * | 2015-01-27 | 2015-05-13 | 荆州市江汉精细化工有限公司 | Preparation method for dimethoxymethylphenylsilane |
| CN104610340B (en) * | 2015-01-27 | 2017-10-10 | 荆州市江汉精细化工有限公司 | A kind of preparation method of aminomethyl phenyl dimethoxysilane |
| CN107915755A (en) * | 2017-11-03 | 2018-04-17 | 山东宝龙达实业集团有限公司 | A kind of Methylethyl diethoxy silane synthetic method |
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