GB1121265A - Production of hydroxymethylsiloxanes - Google Patents
Production of hydroxymethylsiloxanesInfo
- Publication number
- GB1121265A GB1121265A GB31278/66A GB3127866A GB1121265A GB 1121265 A GB1121265 A GB 1121265A GB 31278/66 A GB31278/66 A GB 31278/66A GB 3127866 A GB3127866 A GB 3127866A GB 1121265 A GB1121265 A GB 1121265A
- Authority
- GB
- United Kingdom
- Prior art keywords
- silane
- water
- units
- formula
- siloxane
- 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.)
- Expired
Links
- -1 hydroxymethylsiloxanes Chemical class 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- 229910000077 silane Inorganic materials 0.000 abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 238000006136 alcoholysis reaction Methods 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000000706 filtrate Substances 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- SVZSOVXXWFZQHH-UHFFFAOYSA-N [[hydroxymethyl(dimethyl)silyl]oxy-dimethylsilyl]methanol Chemical compound OC[Si](C)(C)O[Si](C)(C)CO SVZSOVXXWFZQHH-UHFFFAOYSA-N 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 125000005375 organosiloxane group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 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
- C07F7/0872—Preparation and treatment thereof
- C07F7/0874—Reactions involving a bond of the Si-O-Si linkage
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
- Catalysts (AREA)
Abstract
An organosiloxane which contains at least one unit of the formula <FORM:1121265/C3/1> in which m is 1 or 2 and optionally further units of the formula <FORM:1121265/C3/2> in which n is 1, 2 or 3 and R is an alkyl or aryl radical is prepared by heating an acyloxymethyl-silicon compound which is either a silane of the formula <FORM:1121265/C3/3> in which R1 is H or CH3 and R11 is -OCH3, -OC2H5, -OC3H7 or -O.OC.R1, or a siloxane which contains at least one unit of the formula <FORM:1121265/C3/4> and optionally further units of the formula <FORM:1121265/C3/5> with 5 to 20 mols. methanol or ethanol per mol. R1 and a catalytic amount of an aromatic sulphonic acid at a temperature below 100 DEG C. while simultaneously distilling off the resultant esters of the formulae R1C(O)OCH3 or R1C(O)OC2H5 and causing to be present during the reaction the amount of water required for complete hydrolysis and siloxane condensation, neutralizing the catalyst with an excess of alcoholic alkaline solution, filtering off the precipitated salt, freeing the filtrate from volatile components and refiltering to clarify. Suitable catalysts are benzene sulphonic, p-chlorobenzene sulphonic and p-toluene sulphonic acids and alcoholic potassium hydroxide is used to neutralize the catalyst. The filtrate is freed from volatile components by evaporation under reduced pressure, in a current of carbon dioxide, at 20-30 DEG C. Examples of R are methyl and phenyl. The reaction may be carried out such that water is obtained in situ, for example by reacting an acyloxy-silane R1-COOCH2-Si(CH3)2-OOC-R1 and an alkoxy-silane R1-COOCH2-Si(CH3)2-OC2H5 with methanol the first reactant producing water on alcoholysis and the second requiring water for alcoholysis; or water may be added to the reaction mixture. When the acyloxymethyl silicon compound is a silane, the heating may be carried out in the presence of a condensable silane R4- mSi(OH)m or siloxane consisting of units R2Si(OH)O 1/2 and optionally units <FORM:1121265/C3/6> or in the presence of a hydrolysable silane R4- mSi(OR111)m or siloxane consisting of units R2Si(OR111) 1/2 and optionally units <FORM:1121265/C3/7> and water. In the examples, 1,3-di-(hydroxymethyl) - tetramethyl - disiloxane and a linear methylpolysiloxane which is hydroxymethyl substituted in the lateral position are obtained.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF46679A DE1236505B (en) | 1965-07-22 | 1965-07-22 | Process for the production of hydroxymethyl-siloxanes |
| DEF0047467 | 1965-10-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1121265A true GB1121265A (en) | 1968-07-24 |
Family
ID=25976883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31278/66A Expired GB1121265A (en) | 1965-07-22 | 1966-07-12 | Production of hydroxymethylsiloxanes |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE684452A (en) |
| DE (2) | DE1236505B (en) |
| GB (1) | GB1121265A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5099058A (en) * | 1988-07-16 | 1992-03-24 | Josef Sanders | N, N-disubstituted oligourethanes and polyurethanes, a process for their preparation, and their use in the production of plastics |
| US8822621B2 (en) | 2009-10-30 | 2014-09-02 | Wacker Chemie Ag | Method for producing (hydroxymethyl)polysiloxanes |
| US8907039B2 (en) | 2011-08-12 | 2014-12-09 | Wacker Chemie Ag | Method for preparing (hydroxymethyl)polysiloxanes |
| US9096621B2 (en) | 2011-08-12 | 2015-08-04 | Wacker Chemie Ag | Method for preparing poly(hydroxymethyl)-functional siloxanes and silica gels |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4163830A (en) | 1975-12-24 | 1979-08-07 | Bayer Aktiengesellschaft | Process for the production of new polysiloxane-polyoxyalkylene copolymers with reduced burning properties |
-
0
- DE DENDAT1251320D patent/DE1251320B/en active Pending
-
1965
- 1965-07-22 DE DEF46679A patent/DE1236505B/en active Pending
-
1966
- 1966-07-12 GB GB31278/66A patent/GB1121265A/en not_active Expired
- 1966-07-22 BE BE684452D patent/BE684452A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5099058A (en) * | 1988-07-16 | 1992-03-24 | Josef Sanders | N, N-disubstituted oligourethanes and polyurethanes, a process for their preparation, and their use in the production of plastics |
| US8822621B2 (en) | 2009-10-30 | 2014-09-02 | Wacker Chemie Ag | Method for producing (hydroxymethyl)polysiloxanes |
| US8907039B2 (en) | 2011-08-12 | 2014-12-09 | Wacker Chemie Ag | Method for preparing (hydroxymethyl)polysiloxanes |
| US9096621B2 (en) | 2011-08-12 | 2015-08-04 | Wacker Chemie Ag | Method for preparing poly(hydroxymethyl)-functional siloxanes and silica gels |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1251320B (en) | 1967-10-05 |
| BE684452A (en) | 1967-01-03 |
| DE1236505B (en) | 1967-03-16 |
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