CN101058585B - Safe separation method for increasing yield of methyl phenyl dialkoxy silicane - Google Patents
Safe separation method for increasing yield of methyl phenyl dialkoxy silicane Download PDFInfo
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- CN101058585B CN101058585B CN200710068594XA CN200710068594A CN101058585B CN 101058585 B CN101058585 B CN 101058585B CN 200710068594X A CN200710068594X A CN 200710068594XA CN 200710068594 A CN200710068594 A CN 200710068594A CN 101058585 B CN101058585 B CN 101058585B
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- aminomethyl phenyl
- dialkoxy silicane
- silicane
- methylbenzene
- phenyl dialkoxy
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Abstract
The invention discloses a receiving rate improving method of methylbenzene dialkoxy silicane and safe separating method of methylbenzene alkoxy silicane, which comprises the following steps: adopting methylbenzene dichloro-silicane as neutralizing agent; adding the methylbenzene dichloro-silicane into the transmitting material of methylbenzene alkoxy silicane slowly protected by dried air or nitrogen to neutralize under normal temperature or cooling bath; controlling the pH value of composite material to 2-9; filtering slag after reacting; rectifying the filtrate; separating to recycling the solvent and non-reacted raw material; separating the high-purity methylbenzene dialkoxy silicane under certain reflux rate; increasing the receiving rate of methylbenzene dialkoxy silicane in the transmitting material of methylbenzene alkoxy silicane greatly; fitting for preparing the product of national defence, space aviation, architecture and rubber widely.
Description
Technical field
The present invention relates to the organosilicon chemical field, specifically is that a kind of aminomethyl phenyl organoalkoxysilane that improves transforms the yield of aminomethyl phenyl dialkoxy silicane in the material and the method for safe separating aminomethyl phenyl organoalkoxysilane.
Background technology
The aminomethyl phenyl dialkoxy silicane is a kind of important extraordinary organosilane monomer, is widely used in fields such as national defence, space flight and aviation, building and rubber.By Ge Liyafa, prepared by sodium condensation method and redistribution procedure etc., it is higher and have an organoalkoxysilane that mixes alkyl further to make the hydrocarbylation degree by the aminomethyl phenyl dialkoxy silicane.The aminomethyl phenyl dialkoxy silicane also can reduce coating water absorbability, resistance to bond and electromagnetic property directly as the anti-time waterproof auxiliary agent of coating; The anti-linking agent that also can be used as organo-silicone rubber, snappiness, intensity and the ductility etc. of raising silicon rubber; Simultaneously, the aminomethyl phenyl dialkoxy silicane also can be used for preparing diffusion pump oil, methyl phenyl ring siloxane and PSI oligopolymer.The chemical structural formula of aminomethyl phenyl dialkoxy silicane is:
MePhSi(OR)
2
Me is a methyl in the formula, and Ph is a phenyl, and R is methyl or ethyl.
Aminomethyl phenyl dialkoxy silicane suitability for industrialized production adopts prepared by sodium condensation method technology usually, this technology makes sodium Metal 99.5 in toluene and chlorobenzene mixed solvent, generate sodium sand under certain temperature and high shear earlier, methyl trialkoxysilane and chlorobenzene carry out condensation reaction under the sodium sand effect, thereby obtain containing the mix products of aminomethyl phenyl dialkoxy silicane and methyldiphenyl base organoalkoxysilane, promptly so-called conversion material.Not only contain unreacted fluent meterials such as methyl trialkoxysilane, chlorobenzene, toluene solvant, the aminomethyl phenyl dialkoxy silicane that reacts generation and methyldiphenyl base organoalkoxysilane completely in the conversion material, but also contain a large amount of sodium alkoxide solid residues as reaction medium.Rectifying is the effective unit process that separates pure aminomethyl phenyl dialkoxy silicane from transform material, but transform a large amount of sodium alkoxide solid residues that exist in the material, not only have a strong impact on heat and mass transfer in the rectifying, reduce distillation operation efficient, and sodium alkoxide reduces the yield of target product also with the condensation and the rearrangement reaction of catalysis aminomethyl phenyl organoalkoxysilane under the high temperature; Even more serious is, later stage at distillation operation, along with steaming of liquid material in the rectifying tower still, the sodium alkoxide residue is assembled on tower still wall, have a strong impact on the heat and the mass transfer efficiency of tower still, cause tower still temperature distributing disproportionation even, cause sodium alkoxide at high temperature to be heated for a long time and very easily burn, explode, cause the heavy losses of personnel and property.Therefore, transforming material must just can send into rectifying tower and carry out the gas-liquid separation operation through after the separation operations such as neutralization, filter cleaner.
Be dissolved in sodium alkoxide and the sodium alkoxide residue that transforms in the material each component for removing, usually adopt METHYL TRICHLORO SILANE at present as neutralizing agent, utilize the chemical reaction between METHYL TRICHLORO SILANE and the sodium alkoxide, sodium alkoxide is converted into sodium-chlor, again after filtration the operation, remove the sodium-chlor residue after, filtrate is operated through rectifying separation, reclaim reaction solvent, unreacted raw material, and the aminomethyl phenyl dialkoxy silicane that generates.The methyl trialkoxysilane of following sodium-chlor to generate simultaneously in N-process is separated in above-mentioned rectifying, can be used as sodium contract method raw material and recycle.
Though adopt METHYL TRICHLORO SILANE as neutralizing agent can be effectively in and aminomethyl phenyl transform sodium alkoxide in expecting, improve the security of follow-up distillation operation, and the recycle of realization methyl trialkoxysilane, but for being the reaction system in silicon source with the methyltrimethoxy silane, because the boiling point (102 ℃) of methyltrimethoxy silane is comparatively approaching with the boiling point (110 ℃) of toluene solvant with reaction, increased the difficulty of methyltrimethoxy silane and toluene separation and purification; Equally, for being the reaction system in silicon source with the Union carbide A-162, also comparatively approaching with the boiling point (132.2 ℃) that transforms chlorobenzene remaining in the material because of Union carbide A-162 boiling point (143 ℃), increase Union carbide A-162 and separated the difficulty of purifying with chlorobenzene; On the other hand, N-process has just been removed sodium alkoxide and the undissolved sodium alkoxide solid residue that is dissolved in the various chemical substances, needs the security of distillation operation after having increased, but does not increase the yield of target product aminomethyl phenyl dialkoxy silicane; Meanwhile, separate segregational load and separation costs that a large amount of methyl trialkoxysilane that generate in the purification neutralization reaction have also increased rectifying tower, correspondingly reduced the throughput and the production efficiency of aminomethyl phenyl dialkoxy silicane.
A kind of method that the aminomethyl phenyl organoalkoxysilane transforms aminomethyl phenyl dialkoxy silicane yield in the material and safe separating aminomethyl phenyl dialkoxy silicane and methyldiphenyl base organoalkoxysilane that improves of the present invention by literature search, is not appeared in the newspapers.
Summary of the invention
The object of the present invention is to provide a kind of raising aminomethyl phenyl organoalkoxysilane to transform aminomethyl phenyl dialkoxy silicane yield in the material, the method of safety and high efficiency separation aminomethyl phenyl dialkoxy silicane, with solve in the available technology adopting METHYL TRICHLORO SILANE and the aminomethyl phenyl alkoxyl group transforms that the segregational load that dissolved sodium alkoxide and solid sodium ethanol residue exist in the material is heavy, separation costs is high and neutralization reaction product in the problem of each separating substances purification difficult, improve the yield of aminomethyl phenyl dialkoxy silicane simultaneously.
The present invention is achieved by following technical proposals:
A kind of method that improves aminomethyl phenyl dialkoxy silicane yield safe separating, with the dichloromethyl phenylsilane is neutralizing agent, under dry air or nitrogen protection, in normal temperature or cooling bath, slowly adding dichloromethyl phenylsilane to the aminomethyl phenyl organoalkoxysilane transforms in the material and carries out neutralization reaction, PH2～9.0 of control reaction mixture, under the normal temperature behind the filter cleaner, filtrate is operated through rectifying separation, Separation and Recovery reaction solvent and not behind the raw material of complete reaction, under certain reflux ratio, obtain highly purified aminomethyl phenyl dialkoxy silicane at last;
Neutralization reaction equation general formula is as follows:
Wherein R is methyl or ethyl, and when R was methyl, Compound I was an aminomethyl phenyl dimethoxy silane; When R was ethyl, Compound I was the aminomethyl phenyl diethoxy silane.
As preferably, above-mentioned a kind of method that improves aminomethyl phenyl dialkoxy silicane yield safe separating, the purity of dichloromethyl phenylsilane wherein is 70%～98.5%.
As more preferably, above-mentioned a kind of method that improves aminomethyl phenyl dialkoxy silicane yield safe separating, the purity of dichloromethyl phenylsilane wherein is 98.5%.
As preferably, above-mentioned a kind of method that improves aminomethyl phenyl dialkoxy silicane yield safe separating, when neutralization reaction wherein finished, the pH value of the mixture that titration end point obtains was 5.5～7.0.
As better choosing, above-mentioned a kind of method that improves aminomethyl phenyl dialkoxy silicane yield safe separating, when neutralization reaction wherein finished, the pH value of the mixture that titration end point obtains was 7.0.
As preferably, above-mentioned a kind of method that improves aminomethyl phenyl dialkoxy silicane yield safe separating, reflux ratio is 0.1～10: 1 in the aminomethyl phenyl dialkoxy silicane rectifying wherein.
As preferably, above-mentioned a kind of method that improves aminomethyl phenyl dialkoxy silicane yield safe separating, reflux ratio is 4: 1 in the aminomethyl phenyl dialkoxy silicane rectifying wherein.
Raising aminomethyl phenyl organoalkoxysilane of the present invention transforms aminomethyl phenyl dialkoxy silicane yield in the material; the method of safety and high efficiency separation aminomethyl phenyl organoalkoxysilane; with the dichloromethyl phenylsilane is neutralizing agent; under air or nitrogen protection; in normal temperature or cooling bath; dichloromethyl phenylsilane is added drop-wise to the aminomethyl phenyl organoalkoxysilane transforms in the material and carry out neutralization reaction, the gained neutralization reaction product is target product of the present invention-aminomethyl phenyl dialkoxy silicane MePhSi (OR)
2, when R was methyl, target product was an aminomethyl phenyl dimethoxy silane, its boiling point is 199 ℃/100KPa; When R was ethyl, target product was the aminomethyl phenyl diethoxy silane, and its boiling point is 117 ℃/4.133KPa.Since the boiling point of aminomethyl phenyl dimethoxy silane and aminomethyl phenyl diethoxy silane all with separation system in other each boiling point substance significant difference, be easy to adopt rectificating method to separate purification; After reaction is finished, filter cleaner, filtrate under certain reflux ratio, separates obtaining the aminomethyl phenyl dialkoxy silicane and significantly increasing its yield at last after the rectifying separation method reclaims solvent and unreacted raw material;
Neutralization reaction equation general formula is as follows:
Wherein R is methyl or ethyl, and when R was methyl, Compound I was an aminomethyl phenyl dimethoxy silane; When R was ethyl, Compound I was the aminomethyl phenyl diethoxy silane;
Beneficial effect: raising aminomethyl phenyl organoalkoxysilane of the present invention transforms aminomethyl phenyl dialkoxy silicane yield in the material, the method of safety and high efficiency separation aminomethyl phenyl organoalkoxysilane, advantage with the little and operational safety of aminomethyl phenyl dialkoxy silicane yield height, rectifying tower load is suitable for the large-scale commercial production of aminomethyl phenyl dialkoxy silicane.
Embodiment
The present invention can further specify by following embodiment, but embodiment is not a limiting the scope of the invention.
Embodiment 1
Constant voltage pressurization funnel will be housed; it is 10.4 ℃ cooling bath that the 1000mL there-necked flask of agitator and PH meter places temperature; under nitrogen protection; adding the 564.5g sodium method synthetic solid content that contracts in there-necked flask is 30%; aminomethyl phenyl diethoxy silane content is 13.54% aminomethyl phenyl Ethoxysilane conversion material; start and stir; in 0.5h be that 98.2% dichloromethyl phenylsilane is added drop-wise in the there-necked flask by the constant voltage feed hopper lentamente with 103.2g concentration; after dichloromethyl phenylsilane is added dropwise to complete; the mixing solutions temperature is 17.1 ℃ in the there-necked flask, and the mixing solutions pH value is 6.9.The mixture that titration is obtained obtains the 383.9g clear filtrate through filtration under diminished pressure, analyzes through GC, its quality group becomes toluene 40.92%, chlorobenzene 2.78%, aminomethyl phenyl diethoxy silane 36.80%, methyldiphenyl base oxethyl silane 18.40%, methyl triphenyl silane 1.10%.
Above-mentioned filtrate transferred to carry out reduced pressure distillation in the 500mL there-necked flask, reflux ratio with 4: 1 under 4.13KPa is collected 117～118 ℃ of cut 125.53g, analyze through GC, refractive index was 1.4690 when aminomethyl phenyl diethoxy silane content was 99.82%, 25 ℃.After further rectification under vacuum went out methyldiphenyl base oxethyl silane from the still raffinate, residue still raffinate was kept 5h under vacuum, 280 ℃ of temperature, and still raffinate viscosity changes little.
Embodiment 2
Constant voltage pressurization funnel will be housed, it is 8.6 ℃ cooling bath that the 1000mL there-necked flask of agitator and PH meter places temperature, under dry air atmosphere, adding the 560.6g sodium method synthetic solid content that contracts in there-necked flask is 30%, aminomethyl phenyl diethoxy silane content is 13.54% aminomethyl phenyl Ethoxysilane conversion material, start and stir, in 1h be that 90.7% dichloromethyl phenylsilane is added drop-wise in the there-necked flask by the constant voltage feed hopper lentamente with 101.9g concentration, after dichloromethyl phenylsilane is added dropwise to complete, the mixing solutions temperature is 18.7 ℃ in the there-necked flask, and the mixing solutions pH value is 6.6.The mixture that titration is obtained obtains the 289.7g clear filtrate through filtration under diminished pressure, analyzes through GC, its quality group becomes toluene 41.66%, chlorobenzene 2.84%, aminomethyl phenyl diethoxy silane 35.65%, methyldiphenyl base oxethyl silane 18.73%, methyl triphenyl silane 1.13%.
Above-mentioned filtrate transferred to carry out reduced pressure distillation in the 500mL there-necked flask, the reflux ratio with 2: 1 under 4.13KPa is collected 117～118 ℃ of cut 86.52g, analyzes through GC, and refractive index was 1.4688 when aminomethyl phenyl diethoxy silane content was 99.36%, 25 ℃.After further rectification under vacuum went out methyldiphenyl base oxethyl silane from the still raffinate, residue still raffinate was kept 5h under vacuum, 280 ℃ of temperature, and still raffinate viscosity changes little.
Embodiment 3
Constant voltage pressurization funnel will be housed, it is 6.4 ℃ cooling bath that the 1000mL there-necked flask of agitator and PH meter places temperature, under nitrogen atmosphere, adding the 570.2g sodium method synthetic solid content that contracts in there-necked flask is 32%, aminomethyl phenyl dimethoxy silane contents is 17.3% aminomethyl phenyl methoxy silane conversion material, start and stir, in 1.5h be that 95.3% dichloromethyl phenylsilane is added drop-wise in the there-necked flask by the constant voltage feed hopper lentamente with 108.0g concentration, after dichloromethyl phenylsilane is added dropwise to complete, the mixing solutions temperature is 18.9 ℃ in the there-necked flask, and the mixing solutions pH value is 7.0.The mixture that titration is obtained obtains the 303.5g clear filtrate through filtration under diminished pressure, analyzes through GC, its quality group becomes toluene 40.32%, chlorobenzene 2.76%, aminomethyl phenyl dimethoxy silane 39.14%, methyldiphenyl methoxylsilane 16.56%, methyl triphenyl silane 1.22%.
Above-mentioned filtrate transferred to carry out reduced pressure distillation in the 500mL there-necked flask, the reflux ratio with 3: 1 under 1.33KPa is collected 107～108 ℃ of cut 94.19g, analyzes through GC, and refractive index was 1.4693 when aminomethyl phenyl dimethoxy silane contents was 99.54%, 20 ℃.After further rectification under vacuum went out the methyldiphenyl methoxylsilane from the still raffinate, residue still raffinate was kept 4h under vacuum, 295 ℃ of temperature, and still raffinate viscosity changes little.
Claims (5)
1. method that improves aminomethyl phenyl dialkoxy silicane yield safe separating, it is characterized in that: be neutralizing agent with the dichloromethyl phenylsilane, under dry air or nitrogen protection, in normal temperature or cooling bath, slowly adding dichloromethyl phenylsilane to aminomethyl phenyl organoalkoxysilane that the technology that adopts prepared by sodium condensation method suitability for industrialized production aminomethyl phenyl dialkoxy silicane obtains transforms in the material and carries out neutralization reaction, the pH value 2～9.0 of control reaction mixture, under the normal temperature behind the filter cleaner, filtrate is operated through rectifying separation, Separation and Recovery reaction solvent and not behind the raw material of complete reaction, under certain reflux ratio, obtain highly purified aminomethyl phenyl dialkoxy silicane at last; The technology of described prepared by sodium condensation method suitability for industrialized production aminomethyl phenyl dialkoxy silicane is to make sodium Metal 99.5 in toluene and chlorobenzene mixed solvent, generate sodium sand under certain temperature and high shear earlier, methyl trialkoxysilane and chlorobenzene carry out condensation reaction under the sodium sand effect, thereby obtain containing the mix products of aminomethyl phenyl dialkoxy silicane and methyldiphenyl base organoalkoxysilane, promptly described aminomethyl phenyl organoalkoxysilane transforms material;
Neutralization reaction equation general formula is as follows:
Me represent methylidene wherein, Ph represents phenyl, and R is methyl or ethyl, and when R was methyl, Compound I was an aminomethyl phenyl dimethoxy silane; When R was ethyl, Compound I was the aminomethyl phenyl diethoxy silane.
2. according to the described a kind of method that improves aminomethyl phenyl dialkoxy silicane yield safe separating of claim 1, it is characterized in that: when neutralization reaction finished, the pH value of the mixture that titration end point obtains was 5.5～7.0.
3. according to claim 1 or 2 described a kind of methods that improve aminomethyl phenyl dialkoxy silicane yield safe separating, it is characterized in that: when neutralization reaction finished, the pH value of the mixture that titration end point obtains was 7.0.
4. according to the described a kind of method that improves aminomethyl phenyl dialkoxy silicane yield safe separating of claim 1, it is characterized in that: reflux ratio is 0.1～10: 1 in the aminomethyl phenyl dialkoxy silicane rectifying.
5. according to claim 1 or 4 described a kind of methods that improve aminomethyl phenyl dialkoxy silicane yield safe separating, it is characterized in that: reflux ratio is 4: 1 in the aminomethyl phenyl dialkoxy silicane rectifying.
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| CN102424691A (en) * | 2011-11-01 | 2012-04-25 | 上海爱默金山药业有限公司 | Purification method of electronic-grade methyl phenyl diethoxy silane |
| CN102898455B (en) * | 2012-03-21 | 2015-07-29 | 杭州师范大学 | A kind of p-methylphenyl diethoxymethylsilane and preparation method thereof |
| CN102898454B (en) * | 2012-03-21 | 2015-07-29 | 杭州师范大学 | Aminomethyl phenyl diethoxymethylsilane and preparation method thereof between one |
| CN102898456B (en) * | 2012-03-21 | 2015-06-17 | 杭州师范大学 | O-benzyldiethoxymethylsilane and preparation method thereof |
| CN102898457B (en) * | 2012-05-16 | 2015-06-17 | 杭州师范大学 | Ethylphenyldiethoxysilane and preparation method thereof |
| CN103896978B (en) * | 2012-12-27 | 2017-09-19 | 安徽祥源科技股份有限公司 | A kind of method for preparing high-purity methyl phenyidimethoxysilane |
| CN104230977B (en) * | 2014-06-16 | 2016-09-07 | 杭州师范大学 | A kind of ethylphenyl dimethoxysilane and preparation method thereof |
| CN115611938A (en) * | 2022-08-19 | 2023-01-17 | 浙江皇马科技股份有限公司 | Preparation method and application of silane coupling agent |
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| CN1807433A (en) * | 2005-10-31 | 2006-07-26 | 杭州师范学院 | Methylphenyldichlor disilane chemical purification method |
| CN1880320A (en) * | 2006-04-24 | 2006-12-20 | 杭州师范学院 | Chemical method for separating and purifying methylphenyldichlorsilane |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1807433A (en) * | 2005-10-31 | 2006-07-26 | 杭州师范学院 | Methylphenyldichlor disilane chemical purification method |
| CN1880320A (en) * | 2006-04-24 | 2006-12-20 | 杭州师范学院 | Chemical method for separating and purifying methylphenyldichlorsilane |
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Effective date of registration: 20210108 Address after: No.10 Xin'an Road, Huabu Town, Kaihua County, Quzhou City, Zhejiang Province Patentee after: ZHEJIANG KAIHUA SYNTHETIC MATERIAL Co.,Ltd. Address before: Hangzhou City, Zhejiang province 310012 Xiasha Higher Education Park forest Street No. 16 Patentee before: Hangzhou Normal University |