CN102675358A - Preparation method of methylphenyl-cyclosiloxane - Google Patents
Preparation method of methylphenyl-cyclosiloxane Download PDFInfo
- Publication number
- CN102675358A CN102675358A CN2012101602841A CN201210160284A CN102675358A CN 102675358 A CN102675358 A CN 102675358A CN 2012101602841 A CN2012101602841 A CN 2012101602841A CN 201210160284 A CN201210160284 A CN 201210160284A CN 102675358 A CN102675358 A CN 102675358A
- Authority
- CN
- China
- Prior art keywords
- phenyl ring
- methyl phenyl
- ring siloxane
- preparation
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Landscapes
- Silicon Polymers (AREA)
Abstract
The invention relates to a preparation method of methylphenyl-cyclosiloxane, which comprises the following steps: hydrolyzing methylphenyl-dialkoxysilane under normal pressure, and distilling to continuously remove the hydrolysate alcohol compound; and when the density of distillate is approximate to that of water, stopping distillation and refluxing for some time, carrying out oil/water-phase separation, heating the oil phase under reduced pressure to remove water and low-boiling substances, continuing raising the temperature, enhancing the vacuum degree to carry out vacuum distillation, and collecting the methylphenyl-cyclosiloxane fraction. The method provided by the invention does not use any catalyst or neutralizer in the reaction process, and does not need filtering and water washing. The methylphenyl-cyclosiloxane prepared by the method has the advantages of high yield, high purity and good quality.
Description
Technical field
The present invention relates to a kind of method for preparing methyl phenyl ring siloxane, belong to the organic cpds preparing technical field.
Background technology
Be uniform-distribution with phenyl group in the methyl phenyl ring siloxane, can stop the low temperature crystallization of dimethyl-chain link, make that the high-and low-temperature resistance performance of material is largely increased (70 ℃ ~ 350 ℃).Compare with traditional silicon materials; The radiation resistance, fire-retardant fireproof performance, the damping shock absorption performance that contain phenyl chain link silicon materials are excellent more; Therefore be widely used in numerous sophisticated technologies fields such as aerospace industry, nuclear industry, new forms of energy, become indispensable important new and high technology material.
The method for preparing methyl phenyl ring siloxane mainly comprises big type, the one, and through the method acquisition of hydrolysis, a kind of in addition is to obtain through the cracked method.
Hydrolysis prepares methyl phenyl ring siloxane: the working method that General Electric (U.S.A.) in 1998 discloses a kind of octaphenyl cyclotetrasiloxane is (referring to USP 5739370; CN1197073), the basic catalyst hydrolysis dimethoxydiphenylsilane acquisition octaphenyl cyclotetrasiloxane that in the mixed solvent of acetone and water, adds trace.The inventor thinks does not influence the basic catalyst that contains trace in the product fusing point of product, and claims that this method can be used for A
4Preparation.The Japan crowd horse Masafumi Unno of university discloses a kind of method (Masafumi Unno Bull.Chem.Soc.Jpn., 2005,78 that prepare methyl phenyl ring siloxane; 1105 – 1109): potassium hydroxide solution is splashed in the tetrahydrofuran solution of dichloromethyl phenylsilane, reaction removes THF after finishing, through extracted with diethyl ether; Repeatedly washing; Drying concentrates, and obtains A after the rectifying
3, A
4And A
5The deficiency of above method is that the preparation process produces the oil-containing sour water; Need washing, neutralization, drying.
CN 101503421A discloses a kind of preparation method of methyl phenyl ring siloxane, dichloromethyl phenylsilane hydrolysis in heterogeneous solvent can be obtained the aminomethyl phenyl ring body and the partial line body of 80% above yield.This method need be used a large amount of, multiple organic solvent, needs washing, and is unfavorable to environmental protection.
Cracking prepares methyl phenyl ring siloxane: USP 3484469 disclosed a kind of method for preparing the tetramethyl tetraphenyl cyclotetrasiloxane in 1969; With the dichloromethyl phenylsilane hydrolysis, washing, yellow soda ash neutralization; The SODIUM SULPHATE ANHYDROUS 99PCT suction; Filter, obtain viscosity 700CS (20 ℃), the hydrolyzate of refractive index 1.5482 (20 ℃).Add yellow soda ash (potassium, lithium) cracking then, flask is heated to 250 ℃-290 ℃ (3mmHg), collects water and benzene in the deep cooling bottle, collects thick product refractive index 1.544 (20 ℃).Rectifying A then
3150-200 ℃ (0.35mmHg), A
4200-203 ℃ (0.35mmHg), refractive index 1.5448.Wherein the A4 yield 63%.USPs 3558681 in 1971 disclose a kind of method of methyl phenyl ring siloxane; At first be with the dichloromethyl phenylsilane hydrolysis, washing, calcium chloride is dry; Add Lithium Hydroxide MonoHydrate then or the silanol lithium carries out cracking; Rectifying obtains product, the highlyest can obtain 88.6% yield, and can change each other between A3 and the A4.Chinese patent CN102134259 disclosed a kind of method for preparing methyl phenyl ring siloxane in 2011, changed the cracked catalyzer into organic acid lithium salts or organic acid sodium salt, think can so that scission reaction steadily carry out.The deficiency of above method is that the preparation process produces the oil-containing sour water; Need washing, neutralization, drying; Need the basic catalyst cracking.
USP 3989733 disclosed one piece of method (USP 3989733) for preparing methyl phenyl ring siloxane in 1976; The hydrolyzate successive of dichloromethyl phenylsilane is joined the rectifying tower middle part; Rectifying tower upper part charge, lower part is equipped with the Lithium Hydroxide MonoHydrate particle.Thereby be implemented in successive cracking rectifying in the rectifying tower.CN101125860A disclosed a kind of method for preparing methyl phenyl ring siloxane in 2007.With the methyl phenyl silicone that contains phenyl silica trifunctional chain link be raw material under base catalysis, at first remove the low-boiling-point substance that the trifunctional chain link forms, obtain methyl phenyl ring siloxane then.CN101503422 disclosed a kind of method for preparing methyl phenyl ring siloxane in 2009.The aminomethyl phenyl diethoxy silane that generates with prepared by sodium condensation method is raw material hydrolysis under alkaline condition, then hydrolyzate is obtained ring body with the Lithium Hydroxide MonoHydrate cracking.
Summary of the invention
To the deficiency of prior art, the present invention provides a kind of preparation method of methyl phenyl ring siloxane.
Terminological interpretation:
Methyl phenyl ring siloxane typically refers to 1,3,5-trimethylammonium-1,3,5 triphenyl cyclotrisiloxane (A
3), 1,3,5,7-tetramethyl--1,3,5,7 tetraphenyl cyclotetrasiloxane (A
4), 1,3,5,7,9-pentamethyl--1,3,5,7,9 pentapheneyl D5 (A
5) mixture.A wherein
3, A
4, A
5All exist multiple not isomorphic map, exist 2 kinds of conformations to see Fig. 1 (a) (b) like A3, and its content ratio is about 1:3, A
4Exist 4 kinds of conformations see Fig. 1 (c) (d) (e) (f) and its content ratio be about 1:4:2:1, A
5Also have 4 kinds of conformations, and its content ratio is about 1:5:5:5.
It is A that the present invention makes the methyl phenyl ring siloxane product
3, A
4, A
5Mixture, various conformation has performance, A on gas chromatogram
32 peaks, A
44 peaks, A
54 peaks.
Technical scheme of the present invention is following:
A kind of preparation method of methyl phenyl ring siloxane is a hydrolyzing methyl phenyl dialkoxy silicane under condition of normal pressure, constantly removes the hydrolysate alcohol compound through distilling.When the density of overhead product during near the density of water, stop distillation and reflux for some time again, water oil content phase then, oil phase intensification decompression dehydration and low-boiling-point substance continue to improve temperature then, and the methyl phenyl ring siloxane cut is collected in the gas clean-up underpressure distillation.
More detailed, a kind of preparation method of methyl phenyl ring siloxane comprises that step is following:
(1) aminomethyl phenyl dialkoxy silicane and pure water are added the reaction that is hydrolyzed in the reaction vessel by 1:0.1～1 mass ratio; 60 ℃～200 ℃ of hydrolysis temperatures stir, and constantly steam the mixed solution of the first alcohol and water of reaction generation; When steaming fluid density when reaching 0.9～1g/ml; Stop distillation, the 0.5～4h that refluxes tells lower floor's oil phase hydrolyzate.
(2) the oil phase hydrolyzate that step (1) is obtained moves into reaction kettle and carries out decompression dehydration, deviates from low-boiling-point substance, and pressure range is-0.05MPa～-0.098MPa, TR is 80 ℃～200 ℃, the time is 0.5h～8h.
(3) after dewatering, deviating from low-boiling-point substance, continue to heat up, the underpressure distillation methyl phenyl ring siloxane, TR is 200 ℃～400 ℃, pressure range is-0.098MPa～-0.0999MPa.Collect the methyl phenyl ring siloxane cut.
Residual hydrolyzate is transparent dark brown behind the above-mentioned underpressure distillation methyl phenyl ring siloxane, can be used as the anti-irradiation phenyl silicone oil of preparation, perhaps continues to add cracking catalyst and prepares methyl phenyl ring siloxane.
Raw material aminomethyl phenyl dialkoxy silicane of the present invention, wherein alkoxyl group comprises methoxyl group, oxyethyl group, isopropoxy.Described aminomethyl phenyl dialkoxy silicane is one of aminomethyl phenyl dimethoxy silane, aminomethyl phenyl diethoxy silane, aminomethyl phenyl diisopropoxy silane or combination.
According to the present invention, preferred:
The aminomethyl phenyl dialkoxy silicane is 1:0.5～1 with the quality of water than scope in the described hydrolysis reaction.
Described hydrolysis temperature is 80 ℃～120 ℃.Described return time scope is 0.5h～3h.
The dehydration of described oil phase, the TR of deviating from low-boiling-point substance are 100 ℃～200 ℃, pressure range is-and 0.08MPa～-0.098MPa, the time is 2h～6h.
The TR of described distillation methyl phenyl ring siloxane is 200 ℃～300 ℃, pressure range is-and 0.0990MPa～-0.0999MPa.
It is A that the present invention makes the methyl phenyl ring siloxane product
3, A
4, A
5Mixture, A
3, A
4, A
5Between ratio basically at A3:A4:A5=2:5:1.
Method of the present invention is through the hydrolyzing methyl phenyl dialkoxy silicane, and obtaining with the methyl phenyl ring siloxane composition is master's hydrolyzate, obtains the aminomethyl phenyl ring body through underpressure distillation then.Do not use acidity or basic catalyst and neutralizing agent in the whole process, need not wash and filter, reaction is easy to control, and product purity is higher than 99.0%.
Beneficial effect of the present invention is following:
1, do not use catalyzer and neutralizing agent in the reaction process, need not filter and wash.
2, the ring body yield is high, and purity is high, and quality is good.
3, owing at high temperature do not have an alkaline katalysis, thus ruined few to the silicon phenyl, avoid producing a large amount of by product benzene.
Description of drawings
Fig. 1 is methyl phenyl ring siloxane A
3And A
4Not isomorphic map formula.
Fig. 2 is the MWD color atlas of embodiment 1 hydrolyzate.
Fig. 3 is the MWD color atlas of the product methyl phenyl ring siloxane of embodiment 1 preparation.
Fig. 4 is the gas chromatogram of the product methyl phenyl ring siloxane of embodiment 1 preparation.
Fig. 5 is the MWD color atlas of contrast experiment's 2 alkaline hydrolysis gained hydrolyzates.
Embodiment
Through embodiment the present invention is done below and further describe.
The analytical results of gc obtains on Agilent 7890A gas chromatograph among the embodiment, sample size 1ul; Splitting ratio 100:1; 250 ℃ of injector temperatures; Carrier gas is a helium; Hydrogen flameionization detects, 300 ℃ of detector temperatures; Chromatographic column Hp-5; Molecular weight distribution data is the data that more than waters 1515 gel chromatographies, obtain; 20 ℃ of refractive index numerical value obtains on last Nereid section Abbe refractometer; 25 ℃ viscosity numerical value obtains on the permanent flat NDJ-5S rotational viscosimeter in Shanghai.
Embodiment 1: the preparation method of methyl phenyl ring siloxane, and step is following:
(1) gets aminomethyl phenyl dimethoxy silane (GC purity 99.742%, refractive index (20 ℃) 1.4794) 1200g and add in the 3L four-hole round-bottomed flask, the long Webster separation column of 40cm is housed on the four-hole boiling flask; Add the 1200g pure water then, open and stir, slowly be heated to 80 ℃; Constantly steam the mixing solutions of the first alcohol and water of generation; And constantly improve temperature to 100 ℃, and record behind the 10h and steam fluid density and reach 0.996g/ml, tell lower floor's oil phase hydrolyzate behind the 0.5h that refluxes then; The MWD color atlas of hydrolyzate is seen Fig. 2, and analytical results is seen table 1.
Table 1 hydrolyzate MWD analytical results
| RT | Peak molecular weight | Area percentage (%) | The MWD coefficient |
| 27.033 | 3687 | ?1.81 | 1.28 |
| 30.210 | 453 | ?98.19 | 1.10 |
Can find out that from Fig. 2 and table 1 product of small molecular weight surpasses 98%, accounts for absolute majority.And high-molecular weight product content is few.
(2) get hydrolyzate that step (1) obtains and get 332g and join in the 1L round-bottomed flask, slowly reduce pressure-0.095MPa, slowly be warmed up to 200 ℃ simultaneously, observing constantly has water and low-boiling-point substance in cold-trap, to be collected.Gas clean-up (approximately-0.0996MPa), and slowly is warmed up to 280 ℃, has observed cut and produced to the 3mmHg post behind the 4h.Distillation finishes back cooling weighing, analysis.Remaining hydrolyzate 77.9g accounts for 22% of total input amount in the flask.Wherein remaining hydrolyzate is transparent dark brown, viscosity (25 ℃) 9520mpas, test refractive index (20 ℃) 1.5520.The aminomethyl phenyl ring body cut refractive index of collecting (20 ℃) 1.5449, purity 99.343%.In cold-trap, detect micro-benzene and water is miscible.The MWD color atlas of methyl phenyl ring siloxane product is seen Fig. 3, and analytical results is seen table 2, and gas chromatogram is seen Fig. 4, and analytical results is seen table 3.
Table 2 molecular weight of product distributional analysis result
| RT (min) | Peak molecular weight | Area percentage (%) | The MWD coefficient |
| 30.192 | ?458 | ?100.00 | 1.10 |
Table 3 product gas chromatographic analysis result
| RT (min) | The peak name | Area percentage (%) |
| 15.152 | ?A 3 | ?6.578 |
| 16.587 | ?A 3 | ?16.725 |
| 23.318 | ?A 4 | ?8.928 |
| 24.648 | ?A 4 | ?32.222 |
| 24.916 | ?A 4 | ?15.249 |
| 25.217 | ?A 4 | ?8.148 |
| 30.708 | ?A 5 | ?0.806 |
| 31.966 | ?A 5 | ?3.664 |
| 32.357 | ?A 5 | ?3.508 |
| 32.932 | ?A 5 | ?3.515 |
By the molecular weight distribution data of the molecular weight distribution data of Fig. 3 and table 2 product and Fig. 2 and table 1 relatively, through RT, peak molecular weight, distribution coefficient information, can judge that what account for absolute majority in the hydrolyzate is methyl phenyl ring siloxane.
The gas chromatographic analysis data of Fig. 4 and table 3 product can be known A
3, A
4, A
5The aminomethyl phenyl ring body of totally 10 kinds of conformations all occurs, and proportionlity is identical basically.
The contrast experiment 1:
(1) the 500g dichloromethyl phenylsilane slowly is added drop-wise in the 750g water, 70 ℃ are reacted 0.5h then, and the hydrolyzate that obtains reaches neutral through 5 washings after layering.
(2) getting the hydrolyzate 200g that step (1) obtains joins in the four-hole boiling flask; Adding 3.0g Lithium Hydroxide MonoHydrate is heated to 250～300 ℃ and carries out scission reaction; Negative pressure reaches-0.0998MPa, and fractionation obtains aminomethyl phenyl ring body purity 99.64%, refractive index (20 ℃) 1.5447.Residual hydrolyzate at the bottom of the still (account for input amount 20%) and Lithium Hydroxide MonoHydrate particle are bundled together, and the transparency is poor, and viscosity is very high, is difficult to clear up.In cold-trap, collect 0.7g benzene.
The contrast experiment 2:
The sodium hydroxide solution of 576g aminomethyl phenyl dimethoxy silane and 576g 1% joins respectively in the four-hole round-bottomed flask of 2L; The long Webster separation column of 20cm is housed on the four-hole boiling flask; Open and stir, be heated to 80 ℃, constantly have the mixing solutions of methanol-water to be distillated; Distillate density reaches 0.96g/ml behind the 10h, continues backflow 2h.Wash 5 posthydrolysis things and be neutral, vacuum is deviate from moisture and low-boiling-point substance wherein.Tested viscosity (25 ℃) 2060mpas, specific refractory power (20 ℃) 1.5510, fugitive constituent (150 ℃ * 3h) 0.10%.The MWD color atlas is seen Fig. 5.
Can know that through the contrast of Fig. 5 and Fig. 2 the high-molecular weight PSI accounts for absolute majority among Fig. 5, the content of methyl phenyl ring siloxane is then less, and this result with Fig. 2 is significantly different.
Embodiment 2: the preparation method of methyl phenyl ring siloxane, and step is following:
(1) gets aminomethyl phenyl diethoxy silane 500g and add in the 1L four-hole round-bottomed flask, the long Webster separation column of 40cm is housed on the four-hole boiling flask, open and stir; Be heated to 80 ℃; Slowly drip the 200g pure water then, constantly slowly heat up in the dropping process, make the mixing solutions of second alcohol and water constantly steamed; Record behind the 5h and steam fluid density and reach 0.92g/ml, tell lower floor's oil phase hydrolyzate behind the 4h that refluxes then.
(2) get hydrolyzate that step (1) obtains and get 180g and join in the 500mL round-bottomed flask, slowly reduce pressure-0.08MPa, slowly be warmed up to 100 ℃ simultaneously, observing constantly has water and low-boiling-point substance in cold-trap, to be collected.Gas clean-up (approximately-0.0997MPa), and slowly is warmed up to 260 ℃, has observed cut and produced to the 2mmHg post behind the 4h.Distillation finishes back cooling weighing, analysis.The aminomethyl phenyl ring body cut refractive index of collecting (20 ℃) 1.5447, purity 99.53%.In cold-trap, detect micro-benzene and water is miscible.
Embodiment 3: the preparation method of methyl phenyl ring siloxane, and step is following:
(1) the 200g pure water adds in the 2L four-hole round-bottomed flask; The long Webster separation column of 40cm is housed on the four-hole boiling flask; Open stirring and be heated to 100 ℃, slowly drip 1200g aminomethyl phenyl dimethoxy silane then, constantly have the mixing solutions of first alcohol and water to be steamed in the dropping process; Record behind the 9h and steam fluid density and reach 0.93g/ml, tell lower floor's oil phase hydrolyzate behind the 2h that refluxes then.
(2) get the hydrolyzate 260g that step (1) obtains and join in the 500mL round-bottomed flask, slowly reduce pressure-0.095MPa, slowly be warmed up to 150 ℃ simultaneously, observing constantly has water and low-boiling-point substance in cold-trap, to be collected.Gas clean-up (approximately-0.0997MPa), and slowly is warmed up to 260 ℃, has observed cut and produced to the 2mmHg post behind the 4h.Distillation finishes back cooling weighing, analysis.The aminomethyl phenyl ring body cut refractive index of collecting (20 ℃) 1.5445, purity 99.61%, cracking yield 85%.
Claims (8)
1. the preparation method of a methyl phenyl ring siloxane comprises that step is following:
(1) aminomethyl phenyl dialkoxy silicane and pure water are added the reaction that is hydrolyzed in the reaction vessel by 1:0.1～1 mass ratio; 60 ℃～200 ℃ of hydrolysis temperatures stir, and constantly steam the mixed solution of the first alcohol and water of reaction generation; When steaming fluid density when reaching 0.9～1g/ml; Stop distillation, the 0.5～4h that refluxes tells lower floor's oil phase hydrolyzate;
(2) the oil phase hydrolyzate that step (1) is obtained moves into reaction kettle and carries out decompression dehydration, deviates from low-boiling-point substance, and pressure range is-0.05MPa～-0.098MPa, TR is 80 ℃～200 ℃, the time is 0.5h～8h;
(3) after dewatering, deviating from low-boiling-point substance, continue to heat up, the underpressure distillation methyl phenyl ring siloxane, TR is 200 ℃～400 ℃, pressure range is-0.098MPa～-0.0999MPa; Collect the methyl phenyl ring siloxane cut.
2. the preparation method of methyl phenyl ring siloxane as claimed in claim 1 is characterized in that raw material aminomethyl phenyl dialkoxy silicane is one of aminomethyl phenyl dimethoxy silane, aminomethyl phenyl diethoxy silane, aminomethyl phenyl diisopropoxy silane or combination.
3. the preparation method of methyl phenyl ring siloxane as claimed in claim 1 is characterized in that the quality of aminomethyl phenyl dialkoxy silicane and water is 1:0.5～1 than scope in the described hydrolysis reaction.
4. the preparation method of methyl phenyl ring siloxane as claimed in claim 1 is characterized in that described hydrolysis temperature is 80 ℃～120 ℃.
5. the preparation method of methyl phenyl ring siloxane as claimed in claim 1 is characterized in that the described return time scope of step (1) is 0.5h～3h.
6. the preparation method of methyl phenyl ring siloxane as claimed in claim 1; The TR of it is characterized in that the dehydration of the described oil phase of step (2), deviating from low-boiling-point substance is 100 ℃～200 ℃; Pressure range is-0.08MPa～-0.098MPa, the time is 2h～6h.
7. the preparation method of methyl phenyl ring siloxane as claimed in claim 1, the TR that it is characterized in that the described distillation methyl phenyl ring siloxane of step (3) is 200 ℃～300 ℃, pressure range is-0.0990MPa～-0.0999MPa.
8. the preparation method of methyl phenyl ring siloxane as claimed in claim 1; It is characterized in that residual hydrolyzate behind step (3) the underpressure distillation methyl phenyl ring siloxane, be used to prepare anti-irradiation phenyl silicone oil or continue to add cracking catalyst and prepare methyl phenyl ring siloxane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210160284.1A CN102675358B (en) | 2012-05-22 | 2012-05-22 | Preparation method of methylphenyl-cyclosiloxane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210160284.1A CN102675358B (en) | 2012-05-22 | 2012-05-22 | Preparation method of methylphenyl-cyclosiloxane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102675358A true CN102675358A (en) | 2012-09-19 |
| CN102675358B CN102675358B (en) | 2014-10-22 |
Family
ID=46807966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210160284.1A Active CN102675358B (en) | 2012-05-22 | 2012-05-22 | Preparation method of methylphenyl-cyclosiloxane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102675358B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105622663A (en) * | 2016-02-29 | 2016-06-01 | 山东东岳有机硅材料有限公司 | Preparation method of methylphenylcyclosiloxane |
| CN111072715A (en) * | 2019-12-31 | 2020-04-28 | 仙桃市格瑞化学工业有限公司 | Preparation method of bis (phenylcyclosiloxane) |
| CN115124824A (en) * | 2022-08-01 | 2022-09-30 | 太仓市华鼎塑料有限公司 | High-shading PC modified material and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3558681A (en) * | 1968-12-18 | 1971-01-26 | Alexandra Grigorievna Kuznetso | Method for the production of methylphenylcyclotri-and tetrasiloxanes |
| CN1788038A (en) * | 2003-05-13 | 2006-06-14 | 德古萨公司 | Organofunctional siloxane mixtures |
| CN101074284A (en) * | 2007-05-22 | 2007-11-21 | 杭州师范大学 | Production of polymethylphenylsilixane containing trifunctional phenyl-silox-chain |
| CN101343285A (en) * | 2008-08-28 | 2009-01-14 | 杭州师范大学 | Methyl-phenyl hybrid ring siloxane preparing method |
-
2012
- 2012-05-22 CN CN201210160284.1A patent/CN102675358B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3558681A (en) * | 1968-12-18 | 1971-01-26 | Alexandra Grigorievna Kuznetso | Method for the production of methylphenylcyclotri-and tetrasiloxanes |
| CN1788038A (en) * | 2003-05-13 | 2006-06-14 | 德古萨公司 | Organofunctional siloxane mixtures |
| CN101074284A (en) * | 2007-05-22 | 2007-11-21 | 杭州师范大学 | Production of polymethylphenylsilixane containing trifunctional phenyl-silox-chain |
| CN101343285A (en) * | 2008-08-28 | 2009-01-14 | 杭州师范大学 | Methyl-phenyl hybrid ring siloxane preparing method |
Non-Patent Citations (2)
| Title |
|---|
| H. W. AHN等: "Synthesis and Characterization of Cis- and Trans-Trimethyltriphenylcyclotrisiloxane", 《JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS》 * |
| 栾文卉等: "甲基苯基环硅氧烷制备工艺的研究:", 《化学反应工程与工艺》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105622663A (en) * | 2016-02-29 | 2016-06-01 | 山东东岳有机硅材料有限公司 | Preparation method of methylphenylcyclosiloxane |
| CN111072715A (en) * | 2019-12-31 | 2020-04-28 | 仙桃市格瑞化学工业有限公司 | Preparation method of bis (phenylcyclosiloxane) |
| CN115124824A (en) * | 2022-08-01 | 2022-09-30 | 太仓市华鼎塑料有限公司 | High-shading PC modified material and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102675358B (en) | 2014-10-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1997635A (en) | Dihydrobenzofuranyl alkanamine derivatives as 5HT2C agonists | |
| CN102675358A (en) | Preparation method of methylphenyl-cyclosiloxane | |
| EP2285763A1 (en) | Process for olefin etherification | |
| Barton et al. | Mechanism of the decomposition of silacyclobutane to silylene and propene | |
| CN106925351B (en) | N heterocycle carbine ruthenium catalysts containing imidazolium ionic liquid group and preparation method thereof | |
| CN110818735B (en) | Method for preparing 1,1,3, 3-tetramethyldisiloxane | |
| CN106986890B (en) | A kind of environment-friendly preparation method of 2- vinyl -2,4,4,6,6- pentamethyl cyclotrisiloxane | |
| CN102167707B (en) | Retardant plasticizer methyl silicate ester compound and preparation method thereof | |
| CN101648967B (en) | Preparation method of 3-(methacryloxypropyl) propyl-triethoxysilicane | |
| CN101648966B (en) | Method capable of increasing content and yield of gamma-chloropropyltriethoxysilane simultaneously | |
| CN102134320B (en) | Preparation method of organic silicon methoxy/ethoxy high boiling silicone oil | |
| CN106046041A (en) | Piperazinemethylmethyldialkoxysilane compound and preparation and application thereof | |
| CN108690198A (en) | A kind of method that three (pentafluorophenyl group) borine catalysis prepare methyl phenyl silicone oil | |
| CN102134258B (en) | Method for preparing neutral ethyoxyl high-boiling-point silicone oil by using organosilicon high-boiling-point material as raw material | |
| CN105531266A (en) | Improved process for manufacture of tetrahydrofuran | |
| Salvini et al. | Sustainable formation of fatty acid alkyl esters by transesterification of triglycerides with chlorotrimethylsilane | |
| CN108409775A (en) | A kind of preparation method of 1- vinyl -1,1,3,3,3- pentamethyl disiloxanes | |
| CN105669740A (en) | Preparation method of methylphenylcyclosiloxane | |
| CN111302919A (en) | Method for synthesizing high-content dihydrojasmone spice | |
| CN103848726B (en) | A kind of high-purity dihydroxy dibutyl ethers and preparation method thereof | |
| CN105732692B (en) | The synthetic method of aminomethyl phenyl dimethoxysilane | |
| TWI498420B (en) | Manufacture process of oxygenated fuel | |
| CN114011461B (en) | Heterogeneous catalyst based on eutectic solvent and application thereof | |
| CN109678812B (en) | Preparation method of 5-vinyl-2-thiooxazolidine | |
| CN104736515B (en) | The manufacture method of the sour amide of N, N-dialkyl group supreme people's court |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 256401 Tangshan, Shandong, Huantai Town, Zibo Patentee after: Shandong Dongyue organosilicon material Limited by Share Ltd Address before: 256401 Tangshan, Shandong, Huantai Town, Zibo Patentee before: Shandong Dongyue Silicon Material co., Ltd. |
|
| CP01 | Change in the name or title of a patent holder |