CN104151344A - Preparation method of high-purity triisopropyl silyl acrylate - Google Patents
Preparation method of high-purity triisopropyl silyl acrylate Download PDFInfo
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- CN104151344A CN104151344A CN201410339622.7A CN201410339622A CN104151344A CN 104151344 A CN104151344 A CN 104151344A CN 201410339622 A CN201410339622 A CN 201410339622A CN 104151344 A CN104151344 A CN 104151344A
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- silanol
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Abstract
The invention discloses a preparation method of high-purity triisopropyl silyl acrylate. The method comprises the following steps: mixing triisopropyl silanol, a solvent and an acid-binding agent according to the ratio of 1mol to (350-450mol) to (1.1-1.4mol); adding phenothiazine or copper acetate, wherein the mass of phenothiazine or copper acetate is 0.02-0.04% that of triisopropyl silanol; dropwise adding acryloyl chloride at the temperature of 0-80 DEG C, wherein the ratio of acryloyl chloride to triisopropyl silanol is 1mol to (1-1.2mol); continuing to react for 2 hours after dropwise adding is ended; filtering, and rectifying the liquid phase, so as to obtain a product. The high-purity triisopropyl silyl acrylate is mainly applied to a specific antifouling paint in shipping industry as a novel composite functional material monomer at present. A toxic antifouling paint containing tin is slowly replaced by high-purity triisopropyl silyl acrylate which has low toxicity and small pollution. In addition, the product has good strength and excellent tenacity after being subjected to crosslinking molding, is used for manufacturing bulletproof supplies such as helmets in the military field, also can be used as an important medical intermediate, and is wide in application prospect.
Description
Technical field
The present invention relates to a kind of preparation method of high purity triisopropylsilyl acrylate.
Background technology
The extraordinary antifouling paint of the shipping industry of present stage is all stanniferous, and toxicity is higher, contaminate environment, and in addition, the toughness of above-mentioned antifouling paint and intensity are all poor, are unfavorable for life-time service.
Summary of the invention
For solving the problems of the technologies described above, the object of this invention is to provide the preparation method of a kind of triisopropylsilyl acrylate that technique is succinct, safe, yield is high, quality product is high.
For achieving the above object, technical scheme of the present invention is as follows:
A preparation method for high purity triisopropylsilyl acrylate, comprising:
A preparation method for high purity triisopropylsilyl acrylate, is characterized in that, comprises the following steps:
The first step: choose triisopropyl silanol, solvent and acid binding agent, proportionally 1mol: 350～450ml: 1.1～1.4mol mixes;
Second step: add thiodiphenylamine or neutralized verdigris, the quality of thiodiphenylamine or neutralized verdigris is the 0.02-0.04% of triisopropyl silanol quality;
The 3rd step: under temperature 10-80 degree, drip acrylate chloride, the ratio of acrylate chloride and triisopropyl silanol is 1mol: 1～1.2mol;
The 4th step: drip and finish, continue reaction after 2 hours, filter, liquid phase is carried out to rectifying.Preferably, described solvent is one or more in toluene, normal hexane, dimethylbenzene, hexanaphthene, methylcyclohexane.
Preferably, described is easily toluene.
Preferably, described acid binding agent is one or more in triethylamine, DMA, pyridine.
Preferably, described acid binding agent is triethylamine.
Preferably, the ratio of described solvent is 400ml.
Preferably, the quality of described thiodiphenylamine or neutralized verdigris is 0.03% of sec.-propyl silanol quality.
Preferably, described temperature of reaction is 45 degree.
Preferably, the ratio of acrylate chloride and triisopropyl silanol is 1mol: 1.1mol.
In the present embodiment, described stopper refers to one or more in thiodiphenylamine, neutralized verdigris, Resorcinol, MEHQ, BHT, ZJ-705, ZJ-701, and ZJ-705, ZJ-701 are respectively MEHQ and piperidine alcohols oxide compound.
The present invention is as a kind of NEW TYPE OF COMPOSITE functional material monomer, mainly be used at present the extraordinary antifouling paint of shipping industry, because its toxicity is low, pollute littlely, slowly replaced stanniferous virose antifouling paint, in addition, product has good intensity and fabulous toughness after cross moulding, entered at present military industry field and made the shellproof articles for use such as the helmet, it can also serve as a kind of important medicine intermediate, has a extensive future.
Embodiment
Embodiment 1: stir at the band of 1000ml, in the there-necked flask device of nitrogen mouth and drain, under nitrogen protection, choose triisopropyl silanol, toluene and triethylamine, proportionally 1mol: 400ml: 1.2mol mixes, heating under temperature 45 degree, reacts 3 hours; Add thiodiphenylamine, the quality of thiodiphenylamine is 0.03% of triisopropyl silanol quality; Add acrylate chloride, the ratio of acrylate chloride and triisopropyl silanol is 1mol: 1.2mol; React 2 as a child rectifying and draw product, after measured, the rate of recovery of product is 97%, and purity is greater than 99.7%.
Its chemical equation is as follows:
Embodiment 2: stir at the band of 1000ml, in the there-necked flask device of nitrogen mouth and drain, under nitrogen protection, choose triisopropyl silanol, toluene and triethylamine, proportionally 1mol: 350ml: 1.2mol mixes, heating under temperature 5 degree, reacts 3 hours; Add thiodiphenylamine, the quality of thiodiphenylamine is 0.02% of triisopropyl silanol quality; Then add acrylate chloride, the ratio of acrylate chloride and triisopropyl silanol is 1mol: 1.1mol; React 2 as a child rectifying and draw product, after measured, the rate of recovery of product is 93%, and purity is greater than 99.5%.
Its chemical equation is as follows:
Embodiment 3: stir at the band of 1000ml, in the there-necked flask device of nitrogen mouth and drain, under nitrogen protection, choose triisopropyl silanol, toluene and triethylamine, proportionally 1mol: 450ml: 1.2mol mixes, heating under temperature 5 degree, reacts 3 hours; Add thiodiphenylamine, the quality of thiodiphenylamine is 0.01% of triisopropyl silanol quality; Add acrylate chloride, the ratio of acrylate chloride and triisopropyl silanol is 1mol: 1.1mol; React 2 as a child rectifying and draw product, after measured, the rate of recovery of product is 93%, and purity is greater than 99.5%.Reaction formula is the same.
Embodiment 4: stir at the band of 1000ml, in the there-necked flask device of nitrogen mouth and drain, under nitrogen protection, choose triisopropyl silanol, normal hexane benzene and triethylamine, proportionally 1mol: 400ml: 1.3mol mixes, heating under temperature 45 degree, reacts 3 hours; Add thiodiphenylamine, the quality of thiodiphenylamine is 0.03% of triisopropyl silanol quality; Add acrylate chloride, the ratio of acrylate chloride and triisopropyl silanol is 1mol: 1.1mol; React 2 as a child rectifying and draw product, after measured, the rate of recovery of product is 96%, and purity is greater than 99.7%.Reaction formula is the same.
Embodiment 5: stir at the band of 1000ml, in the there-necked flask device of nitrogen mouth and drain, under nitrogen protection, choose triisopropyl silanol, dimethylbenzene and triethylamine, proportionally 1mol: 400ml: 1.3mol mixes, heating under temperature 45 degree, reacts 3 hours; Add thiodiphenylamine, the quality of thiodiphenylamine is 0.03% of triisopropyl silanol quality; Add acrylate chloride, the ratio of acrylate chloride and triisopropyl silanol is 1mol: 1.1mol; React 2 as a child rectifying and draw product, after measured, the rate of recovery of product is 96%, and purity is greater than 99.7%.Reaction formula is the same.
Embodiment 6: stir at the band of 1000ml, in the there-necked flask device of nitrogen mouth and drain, under nitrogen protection, choose triisopropyl silanol, normal hexane benzene and pyridine, proportionally 1mol: 400ml: 1.3mol mixes, heating under temperature 45 degree, reacts 3 hours; Add neutralized verdigris, the quality of neutralized verdigris is 0.03% of triisopropyl silanol quality; Add acrylate chloride, the ratio of acrylate chloride and triisopropyl silanol is 1mol: 1.1mol; React 2 as a child rectifying and draw product, after measured, the rate of recovery of product is 96%, and purity is greater than 99.7%.Reaction formula is the same.
Embodiment 7: stir at the band of 1000ml, in the there-necked flask device of nitrogen mouth and drain, under nitrogen protection, choose triisopropyl silanol, normal hexane benzene and pyridine, proportionally 1mol: 400ml: 1.3mol mixes, heating under temperature 80 degree, reacts 3 hours; Add neutralized verdigris, the quality of neutralized verdigris is 0.03% of triisopropyl silanol quality; Add acrylate chloride, the ratio of acrylate chloride and triisopropyl silanol is 1mol: 1.1mol; React 2 as a child rectifying and draw product, after measured, the rate of recovery of product is 95%, and purity is greater than 99.5%.Reaction formula is the same.
The present invention is as a kind of NEW TYPE OF COMPOSITE functional material monomer, mainly be used at present the extraordinary antifouling paint of shipping industry, because its toxicity is low, pollute littlely, slowly replaced stanniferous virose antifouling paint, in addition, product has good intensity and fabulous toughness after cross moulding, entered at present military industry field and made the shellproof articles for use such as the helmet, it can also serve as a kind of important medicine intermediate, has a extensive future.
To be apparent for those skilled in the art to the multiple amendment of these embodiment, general your principle as defined herein can, in the situation that not departing from the spirit or scope of the present invention, realize in other embodiments.
Claims (9)
1. a preparation method for high purity triisopropylsilyl acrylate, is characterized in that, comprises the following steps:
The first step: choose triisopropyl silanol, solvent and acid binding agent, proportionally 1mol: 350～450ml: 1.1～1.4mol mixes;
Second step: add thiodiphenylamine or neutralized verdigris, the quality of thiodiphenylamine or neutralized verdigris is the 0.02-0.04% of triisopropyl silanol quality;
The 3rd step: under temperature 10-80 degree, drip acrylate chloride, the ratio of acrylate chloride and triisopropyl silanol is 1mol:1 ~ 1.2mol;
The 4th step: drip and finish, continue reaction after 2 hours, filter, liquid phase is carried out to rectifying.
2. the preparation method of high purity triisopropylsilyl acrylate according to claim 1, is characterized in that, described solvent is one or more in toluene, normal hexane, dimethylbenzene, hexanaphthene, methylcyclohexane.
3. the preparation method of high purity triisopropylsilyl acrylate according to claim 2, is characterized in that, described solvent is toluene.
4. the preparation method of high purity triisopropylsilyl acrylate according to claim 1, is characterized in that, described acid binding agent is one or more in triethylamine, DMA, pyridine.
5. the preparation method of high purity triisopropylsilyl acrylate according to claim 4, is characterized in that, described acid binding agent is triethylamine.
6. the preparation method of high purity triisopropylsilyl acrylate according to claim 1, is characterized in that, the ratio of described solvent is 400ml.
7. the preparation method of high purity triisopropylsilyl acrylate according to claim 1, is characterized in that, the quality of described thiodiphenylamine or neutralized verdigris is 0.03% of sec.-propyl silanol quality.
8. the preparation method of high purity triisopropylsilyl acrylate according to claim 1, is characterized in that, described temperature of reaction is 45 degree.
9. the preparation method of high purity triisopropylsilyl acrylate according to claim 1, is characterized in that, the ratio of acrylate chloride and triisopropyl silanol is 1mol:1.1mol.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201410339622.7A CN104151344A (en) | 2014-07-17 | 2014-07-17 | Preparation method of high-purity triisopropyl silyl acrylate |
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| CN201410339622.7A CN104151344A (en) | 2014-07-17 | 2014-07-17 | Preparation method of high-purity triisopropyl silyl acrylate |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447844A (en) * | 2014-10-23 | 2015-03-25 | 扬州三友合成化工有限公司 | Preparation method of high purity triisopropylsilyl methacrylate |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003027124A1 (en) * | 2001-09-21 | 2003-04-03 | Sigma Coatings B.V. | Process for the preparation of organosilylated carboxylate monomers, and their use in antifouling coatings |
| JP2004067582A (en) * | 2002-08-06 | 2004-03-04 | Hokko Chem Ind Co Ltd | Method for producing triorganosilyl unsaturated carboxylate |
| JP2006199638A (en) * | 2005-01-21 | 2006-08-03 | Kemikurea:Kk | Method for producing polymerizable triorganosilyl unsaturated carboxylate |
| US20060252953A1 (en) * | 2002-12-20 | 2006-11-09 | Sigma Coatings B.V. | Process for the production of silyl carboxylate monomers |
| CN103709190A (en) * | 2014-01-08 | 2014-04-09 | 浙江胡涂硅有限公司 | Method for preparing triisopropyl silicon acrylate |
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2014
- 2014-07-17 CN CN201410339622.7A patent/CN104151344A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003027124A1 (en) * | 2001-09-21 | 2003-04-03 | Sigma Coatings B.V. | Process for the preparation of organosilylated carboxylate monomers, and their use in antifouling coatings |
| JP2004067582A (en) * | 2002-08-06 | 2004-03-04 | Hokko Chem Ind Co Ltd | Method for producing triorganosilyl unsaturated carboxylate |
| US20060252953A1 (en) * | 2002-12-20 | 2006-11-09 | Sigma Coatings B.V. | Process for the production of silyl carboxylate monomers |
| JP2006199638A (en) * | 2005-01-21 | 2006-08-03 | Kemikurea:Kk | Method for producing polymerizable triorganosilyl unsaturated carboxylate |
| CN103709190A (en) * | 2014-01-08 | 2014-04-09 | 浙江胡涂硅有限公司 | Method for preparing triisopropyl silicon acrylate |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447844A (en) * | 2014-10-23 | 2015-03-25 | 扬州三友合成化工有限公司 | Preparation method of high purity triisopropylsilyl methacrylate |
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Application publication date: 20141119 |