CN107814818A - One kind four（Trimethylsiloxy group）The synthesis technique of silane - Google Patents
One kind four（Trimethylsiloxy group）The synthesis technique of silane Download PDFInfo
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- CN107814818A CN107814818A CN201711420045.4A CN201711420045A CN107814818A CN 107814818 A CN107814818 A CN 107814818A CN 201711420045 A CN201711420045 A CN 201711420045A CN 107814818 A CN107814818 A CN 107814818A
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- Prior art keywords
- reaction
- silane
- trimethylsiloxy group
- hmdo
- synthesis technique
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims abstract description 22
- -1 Trimethylsiloxy Chemical group 0.000 title claims abstract description 21
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 21
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 15
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims abstract description 20
- VXEGSRKPIUDPQT-UHFFFAOYSA-N 4-[4-(4-methoxyphenyl)piperazin-1-yl]aniline Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2C=CC(N)=CC=2)CC1 VXEGSRKPIUDPQT-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000005049 silicon tetrachloride Substances 0.000 claims abstract description 15
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 238000013517 stratification Methods 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 238000013019 agitation Methods 0.000 claims description 10
- 238000004448 titration Methods 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 239000005457 ice water Substances 0.000 claims description 6
- 239000012452 mother liquor Substances 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims 1
- 229940073561 hexamethyldisiloxane Drugs 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 22
- 239000000126 substance Substances 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000003377 acid catalyst Substances 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000006467 substitution reaction Methods 0.000 abstract description 2
- 230000003292 diminished effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002537 cosmetic Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 206010054949 Metaplasia Diseases 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 230000015689 metaplastic ossification Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0874—Reactions involving a bond of the Si-O-Si linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
The present invention relates to one kind four（Trimethylsiloxy group）The synthesis technique of silane, belong to organosilicon synthesis chemical field.The present invention is using silicon tetrachloride, HMDO as raw material, under conditions of acid catalyst, reaction generation four（Trimethylsiloxy group）Silane.Reaction is filtered under diminished pressure after terminating, and stratification simultaneously collects upper solution, and trim,ethylchlorosilane is distilled out under normal pressure, is then being evaporated under reduced pressure out excessive HMDO raw material and four（Trimethylsiloxy group）Silane product.The present invention has simple in production process operation, and production cost is low, easily separated, high income, quality better, and product content reaches more than 99.0%, and three substitution by-products contents are less than 0.1%, and molar yield reaches more than 96.8%.
Description
Technical field
The present invention relates to one kind four（Trimethylsiloxy group）The synthesis technique of silane, belong to organosilicon synthesis chemical field.
Background technology
Four（Trimethylsiloxy group）Silane is a kind of important silicone intermediate, belongs to silanes, is widely used in all
The synthesis of more cosmetics, it is related to skin care item, hair products, ultraviolet protection product, perfume, face cream, emulsion, sun-screening agent, facial mask, palpus
Water, makeup cosmetic etc. afterwards.The silane structure is symmetrical structure, i.e., by four chlorine atoms in silicon tetrachloride all by trimethyl
The product of siloxy substitution, is a kind of oiliness organo-silicon compound, and product chemical property is highly stable, nontoxic, and for human body
Skin does not have an excitant, and use is very safe.
On four（Trimethylsiloxy group）The synthesis document of silane is less, only a small amount of patent literature.Patent EP
The synthesis technique of 1607081A1 reports is fairly simple, is directly urged using tetramethoxy-silicane with HMDO in acidity
Under agent, react to obtain with water.But there is following four in the technique：（1）Relative to silicon tetrachloride, tetramethoxy-silicane
Alkane it is active relatively low, when being reacted with HMDO, four methoxy groups are difficult to thoroughly be substituted on molecule, there is 2 ~ 5%
The accessory substance of content（Three substituted compounds）Generation；（2）The boiling point of three substituent boiling points and product is very close, in production process
In, energy consumption of rectification is big, and is still difficult to obtain the product of high content；（3）A large amount of methanol containing sour water are produced in this method course of reaction,
Water easily produces azeotropic, bad separation, it is difficult to recycling, cause high expensive with methanol.
The content of the invention
It is an object of the invention to：There is provided that a kind of technique is simple, and cost is low, product content is high, and the substituent of accessory substance three contains
Measure low four（Trimethylsiloxy group）The synthesis technique of silane.
The technical scheme is that：
One kind four（Trimethylsiloxy group）The synthesis technique of silane, it is characterised in that it comprises the following steps：
1）, with mechanical agitation, constant pressure titration funnel and condenser reactor in put into a certain amount of silica of hexamethyl two
Alkane, reaction system is cooled using ice-water bath mode, and after system temperature reaches 1 ~ 5 DEG C, catalyst, machine are added into reaction system
0.5 ~ 3h of the lower reaction of tool stirring.
2）, keep temperature of reaction system be 1 ~ 5 DEG C, weigh a certain amount of silicon tetrachloride be added to constant pressure titration funnel, open
Beginning dropwise reaction, the time for adding of silicon tetrachloride is 0.5 ~ 3h, after dripping, continues 1 ~ 5h of reaction；Kept back in course of reaction
It is -10 ~ -5 DEG C to flow device condensation temperature；
3）, after reaction terminates, reaction mother liquor is transferred in separatory funnel, stratification 1h, upper strata is organic layer, and lower floor is urges
Agent（It is repeatable to utilize）.
4）, collect upper strata after, distill out trim,ethylchlorosilane at ambient pressure, distill obtained trim,ethylchlorosilane quantitative
Water in the presence of, reaction is hydrolyzed and obtains HMDO, can reuse；Then it is evaporated under reduced pressure out excessive six
Tetramethyldisiloxane raw material, obtains four（Trimethylsiloxy group）Silane product；
The chemical equation of the present invention is as follows：
Described catalyst is the concentrated sulfuric acid.The addition of catalyst is the 0.1 ~ 2% of HMDO quality.
Described silicon tetrachloride and HMDO mol ratio are 1：4.1.
The advantage of the invention is that：
1）, synthesis technique provided by the invention, it is necessary to distillation equipment it is relatively easy, and distillation efficiency is higher, is more suitable for industry
Metaplasia is produced.
2）, relative to tetramethoxy-silicane, use the silicon tetrachloride of high activity under the conditions of anhydrous, to pass through for raw material
Acid catalyst synthesizes to obtain four（Trimethylsiloxy group）Silane product, cost is low, easily separated, high income, quality better, three in product
By-products content is substituted to be less than 0.1%, product content reaches more than 99.0%, and molar yield reaches more than 96.8%.
3）, generation trim,ethylchlorosilane, easily recovery, can be re-used for synthesize HMDO.Meanwhile urge
The agent concentrated sulfuric acid can reuse, both economically and environmentally beneficial.
4）, four（Trimethylsiloxy group）Silane product is widely used in a variety of cosmetics, has huge development space with before
Scape.
Embodiment
Embodiment 1
665.8g is added in tetra- mouthfuls of reaction flasks of 2000ml with mechanical agitation, constant pressure titration funnel and condenser
（4.1mol）HMDO, reaction system is cooled using ice-water bath mode, after system temperature reaches 0 ~ 5 DEG C, to anti-
The addition 13.0g catalyst concentrated sulfuric acids in system are answered, react 1h under mechanical agitation.
Then 169.9g tetrachloro silicanes are weighed（1mol）It is added in constant pressure funnel, starts dropwise reaction, during dropwise addition
Between be 1h, maintain the reflux for -10~-5 DEG C of device condensation temperature during this.After silicon tetrachloride drips, continue at this temperature
React 3h.After reaction terminates, reaction mother liquor is transferred in separatory funnel, stratification 1h, upper strata is organic layer, and lower floor is to urge
The agent concentrated sulfuric acid（It is repeatable to utilize）.After collecting upper strata, trim,ethylchlorosilane is distilled out at ambient pressure, was then evaporated under reduced pressure out
The HMDO raw material of amount, finally obtains four（Trimethylsiloxy group）Silane product 376.4g, content are 99.0% production
Product, molar yield 96.8%（Calculated with silicon tetrachloride）.
Embodiment 2
665.8g is added in tetra- mouthfuls of reaction flasks of 2000ml with mechanical agitation, constant pressure titration funnel and condenser
（4.1mol）HMDO, reaction system is cooled using ice-water bath mode, after system temperature reaches 0 ~ 5 DEG C, to anti-
The addition 10.0g catalyst concentrated sulfuric acids in system are answered, react 1h under mechanical agitation.
Then 169.9g tetrachloro silicanes are weighed（1mol）It is added in constant pressure funnel, starts dropwise reaction, during dropwise addition
Between be 1.5h, maintain the reflux for -10~-5 DEG C of device condensation temperature during this.After silicon tetrachloride drips, continue in this temperature
Lower reaction 2.5h.After reaction terminates, reaction mother liquor is transferred in separatory funnel, stratification 1h, upper strata is organic layer, lower floor
For the catalyst concentrated sulfuric acid（It is repeatable to utilize）.After collecting upper strata, trim,ethylchlorosilane is distilled out at ambient pressure, is then evaporated under reduced pressure
Go out excessive HMDO raw material, finally obtain four（Trimethylsiloxy group）Silane product 377.1g, content 99.1%
Product, molar yield 97.1%.
Embodiment 3
665.8g is added in tetra- mouthfuls of reaction flasks of 2000ml with mechanical agitation, constant pressure titration funnel and condenser
（4.1mol）HMDO, reaction system is cooled using ice-water bath mode, after system temperature reaches 0 ~ 5 DEG C, to anti-
The addition 8.0g catalyst concentrated sulfuric acids in system are answered, react 1h under mechanical agitation.
Then 169.9g tetrachloro silicanes are weighed（1mol）It is added in constant pressure funnel, starts dropwise reaction, during dropwise addition
Between be 2h, maintain the reflux for -10~-5 DEG C of device condensation temperature during this.After silicon tetrachloride drips, continue at this temperature
React 2.5h.After reaction terminates, reaction mother liquor is transferred in separatory funnel, stratification 1h, upper strata is organic layer, and lower floor is
The catalyst concentrated sulfuric acid（It is repeatable to utilize）.After collecting upper strata, trim,ethylchlorosilane is distilled out at ambient pressure, is then evaporated under reduced pressure out
Excessive HMDO raw material, finally obtains four（Trimethylsiloxy group）Silane product 379.4g, content are 99.3%
Product, molar yield 97.8%.
Embodiment 4
665.8g is added in tetra- mouthfuls of reaction flasks of 2000ml with mechanical agitation, constant pressure titration funnel and condenser
（4.1mol）HMDO, reaction system is cooled using ice-water bath mode, after system temperature reaches 0 ~ 5 DEG C, to anti-
The addition 6.0g catalyst concentrated sulfuric acids in system are answered, react 1h under mechanical agitation.
Then 169.9g tetrachloro silicanes are weighed（1mol）It is added in constant pressure funnel, starts dropwise reaction, during dropwise addition
Between be 2.5h, maintain the reflux for -10~-5 DEG C of device condensation temperature during this.After silicon tetrachloride drips, continue in this temperature
Lower reaction 1.5h.After reaction terminates, reaction mother liquor is transferred in separatory funnel, stratification 1h, upper strata is organic layer, lower floor
For the catalyst concentrated sulfuric acid（It is repeatable to utilize）.After collecting upper strata, trim,ethylchlorosilane is distilled out at ambient pressure, is then evaporated under reduced pressure
Go out excessive HMDO raw material, finally obtain four（Trimethylsiloxy group）Silane product 381.0g, content 99.2%
Product, molar yield 98.2%.
Claims (3)
1. one kind four（Trimethylsiloxy group）The synthesis technique of silane, it is characterised in that：It comprises the following steps：
1）, with mechanical agitation, constant pressure titration funnel and condenser reactor in put into a certain amount of silica of hexamethyl two
Alkane, reaction system is cooled using ice-water bath mode, and after system temperature reaches 1 ~ 5 DEG C, catalyst, machine are added into reaction system
0.5 ~ 3h of the lower reaction of tool stirring；
2）, keep temperature of reaction system be 1 ~ 5 DEG C, weigh a certain amount of silicon tetrachloride be added to constant pressure titration funnel, start to drip
Add reaction, the time for adding of silicon tetrachloride is 0.5 ~ 3h, after dripping, continues 1 ~ 5h of reaction；Maintain the reflux for filling in course of reaction
Condensation temperature is put as -10 ~ -5 DEG C；
3）, after reaction terminates, reaction mother liquor is transferred in separatory funnel, stratification 1h, upper strata is organic layer, and lower floor is urges
The agent concentrated sulfuric acid；
4）, collect upper strata after, distill out trim,ethylchlorosilane at ambient pressure, the trim,ethylchlorosilane for distilling to obtain is in quantitative water
In the presence of, reaction is hydrolyzed and obtains HMDO, can reuse；Then it is evaporated under reduced pressure out excessive hexamethyl
Disiloxane raw material, obtains four（Trimethylsiloxy group）Silane product.
2. according to claim 1 a kind of four（Trimethylsiloxy group）The synthesis technique of silane, it is characterised in that：Described
Catalyst is the concentrated sulfuric acid；The addition of catalyst is the 0.3 ~ 2% of HMDO quality.
3. according to claim 1 a kind of four（Trimethylsiloxy group）The synthesis technique of silane, it is characterised in that：Described
Silicon tetrachloride and HMDO mol ratio are 1：4.1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711420045.4A CN107814818A (en) | 2017-12-25 | 2017-12-25 | One kind four（Trimethylsiloxy group）The synthesis technique of silane |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711420045.4A CN107814818A (en) | 2017-12-25 | 2017-12-25 | One kind four（Trimethylsiloxy group）The synthesis technique of silane |
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| CN201711420045.4A Pending CN107814818A (en) | 2017-12-25 | 2017-12-25 | One kind four（Trimethylsiloxy group）The synthesis technique of silane |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109320638A (en) * | 2018-09-29 | 2019-02-12 | 四川锦成化学催化剂有限公司 | Internal electron donor, catalytic component and the catalyst of ethylene polymerization Ziegler-Natta catalyst |
| WO2020025144A1 (en) * | 2018-08-03 | 2020-02-06 | Wacker Chemie Ag | Process for producing organosiloxanes comprising triorganosilyloxy groups |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1761449A (en) * | 2003-03-19 | 2006-04-19 | 株式会社钟纺化妆品 | Cosmetic preparation |
-
2017
- 2017-12-25 CN CN201711420045.4A patent/CN107814818A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1761449A (en) * | 2003-03-19 | 2006-04-19 | 株式会社钟纺化妆品 | Cosmetic preparation |
Non-Patent Citations (1)
| Title |
|---|
| VORONKOV, M. G.等: "Cleavage of the silicon-oxygen-silicon group by tetrachlorosilane and organylchlorosilanes", 《DOKLADY AKADEMII NAUK SSSR》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020025144A1 (en) * | 2018-08-03 | 2020-02-06 | Wacker Chemie Ag | Process for producing organosiloxanes comprising triorganosilyloxy groups |
| CN109320638A (en) * | 2018-09-29 | 2019-02-12 | 四川锦成化学催化剂有限公司 | Internal electron donor, catalytic component and the catalyst of ethylene polymerization Ziegler-Natta catalyst |
| CN109320638B (en) * | 2018-09-29 | 2021-03-26 | 四川锦成化学催化剂有限公司 | Ziegler-Natta catalyst component and catalyst for ethylene polymerization |
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Application publication date: 20180320 |