GB730379A - Method of preparing organic silicon compounds - Google Patents
Method of preparing organic silicon compoundsInfo
- Publication number
- GB730379A GB730379A GB24652/51A GB2465251A GB730379A GB 730379 A GB730379 A GB 730379A GB 24652/51 A GB24652/51 A GB 24652/51A GB 2465251 A GB2465251 A GB 2465251A GB 730379 A GB730379 A GB 730379A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- silicon
- ethylene
- reacted
- compound
- 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
- 238000000034 method Methods 0.000 title abstract 5
- 150000003377 silicon compounds Chemical class 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 16
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 11
- 239000005977 Ethylene Substances 0.000 abstract 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 6
- 229930195733 hydrocarbon Natural products 0.000 abstract 6
- 229910000077 silane Inorganic materials 0.000 abstract 6
- 229910052710 silicon Inorganic materials 0.000 abstract 6
- XMIJDTGORVPYLW-UHFFFAOYSA-N [SiH2] Chemical compound [SiH2] XMIJDTGORVPYLW-UHFFFAOYSA-N 0.000 abstract 5
- 239000007859 condensation product Substances 0.000 abstract 5
- 150000002430 hydrocarbons Chemical class 0.000 abstract 5
- 239000000376 reactant Substances 0.000 abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 239000001301 oxygen Substances 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 4
- 239000010703 silicon Substances 0.000 abstract 4
- -1 siloxanes Chemical class 0.000 abstract 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 3
- XLXGCFTYXICXJF-UHFFFAOYSA-N ethylsilicon Chemical compound CC[Si] XLXGCFTYXICXJF-UHFFFAOYSA-N 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 abstract 3
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 abstract 2
- 241000219289 Silene Species 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 2
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 238000009835 boiling Methods 0.000 abstract 2
- 150000001805 chlorine compounds Chemical class 0.000 abstract 2
- KZZFGAYUBYCTNX-UHFFFAOYSA-N diethylsilicon Chemical compound CC[Si]CC KZZFGAYUBYCTNX-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002170 ethers Chemical class 0.000 abstract 2
- 150000002366 halogen compounds Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 150000002894 organic compounds Chemical class 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910008051 Si-OH Inorganic materials 0.000 abstract 1
- 229910002808 Si–O–Si Inorganic materials 0.000 abstract 1
- 229910006358 Si—OH Inorganic materials 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- JZZIHCLFHIXETF-UHFFFAOYSA-N dimethylsilicon Chemical compound C[Si]C JZZIHCLFHIXETF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000007717 exclusion Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229920001296 polysiloxane Polymers 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 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
- C07F7/04—Esters of silicic acids
-
- 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
- C07F7/0896—Compounds with a Si-H 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
- C07F7/025—Silicon compounds without C-silicon linkages
-
- 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
- C07F7/0801—General processes
-
- 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
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/0827—Syntheses with formation of a Si-C bond
-
- 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
- C07F7/12—Organo silicon halides
-
- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Silicon Polymers (AREA)
Abstract
Resinous condensation products are obtained by reacting at least one hydrocarbon comprising a saturated, unsaturated, open chain and/or ring compound with a halogen free silicon compound having at least one Si-H bond at a temperature between 150 DEG and 160 DEG C., preferably about 450 DEG C., and under a subatmospheric pressure. The hydrocarbons may be substituted and contain halogen, oxygen, nitrogen or sulphur. Suitable silicon reactants are silane and its homologues, silenes, siloxanes, siloxene and its derivatives, and polymeric silicon dihydride. The organic reactant may have single or multiple bonds, e.g. pentane, cyclohexane and ethylene and their homologues may be used. Suitable substituted organic compounds for use in the above process are ethers, esters, aldehydes, ketones and organic oxides and halogen compounds especially chlorides such as methyl ethyl, propyl, vinyl and allyl chloride. Oily condensation products obtained by the above process may be thickened by heating with the exclusion of oxygen, or may be allowed to harden by exposure to the air, e.g. to form a coating on a surface. In addition to the resinous condensation products obtained by the above process, organic silicon compounds having 1 to 3 hydrogen atoms attached to a silicon atom may be prepared and may be subjected to oxidation or hydrolysis to form silicones having similar uses to the oily condensation products referred to above. In the examples resinous condensation products are obtained by reacting silane with each of the following reactants:-ethylene, ethylene oxide, ether and acetone. A polymeric oil having the composition (SiClR)x, where R represents CH3, C2H5 and C3H7, and a solid polymeric substance having the empirical formula (Si2ClR)x, where R represents butyl, are obtained by reacting silane and vinyl chloride. A solid polymer of the formula (CH3Si)x is isolated from the product obtained by reacting ethylene and silane.ALSO:Organic-silicon compounds which contain in the molecule one silicon atom or a plurality of silicon atoms either directly bound to each other or through one or more carbon atoms by reacting at least one hydrocarbon comprising a saturated, unsaturated, open-chain and/or ring compound with a halogen-free silicon compound having at least one Si-H bond at a temperature between 150 DEG and 600 DEG C., preferably about 450 DEG C., and under a sub-atmospheric pressure. The hydrocarbons may be substituted and contain halogen, oxygen, nitrogen or sulphur. Suitable silicon reactants are silane and its homologues, silenes, siloxanes, siloxene and its derivatives and polymeric silicon dihydride. The organic reactant may have single or multiple bonds such as pentane, ethylene and cyclohexane and their homologues. Substituted organic compounds which may be used are ethers, esters, aldehydes, ketones and organic oxides, and halogen compounds especially chlorides such as methyl, ethyl, propyl and allyl chloride. The reaction between silane and the oxygen containing hydrocarbons such as diethyl ether, acetone or ethylene oxide produces primarily alkoxy silanes of the type ROSiH3. In the case of diethyl ether high-boiling substances containing Si-H bonds are obtained, e.g., a compound of the type (H5C2O)2HSiOSiH(OC2H5)2. Othe types of compounds which are prepared may contain one hydrocarbon radical attached to silicon as in CH3SiH3 or C2H5SiH3, or may be of the formula R2SiH2 as exemplified by (CH3) (C2H5)SiH2, (CH3) (C3H7)SiH2 or (C2H5)2SiH2, or compounds of the type R3SiH and R4Si, in which one or more hydrogen atoms may also be substituted by silicon-hydrocarbon radicals to form, for instance, a compound of the formula (C2H5)2CH3SiCH2SiCH3(C2 H5)2. Products containing hydrogen attached to silicon may be subjected to oxidation or hydrolysis to form compounds having Si-OH or Si-O-Si bonds. In the examples: (1) monosilane and ethylene are reacted in accordance with the above process to produce the compounds CH3SiH3, C2H5SiH3, (CH3)3 Si H, (CH3)4 Si, (C3 H7 CH3 Si H2, (C2H5) CH3 Si H2, (C2H5)2\t Si H2, (C2H5)3 Si H, Si2 (CH3) (C2 H5)4 H, Si2 (CH3)3 (C2 H5)3 and Si2 (C2 H5)3 (C3 H7) H2; (2) monosilane and ethylene oxide are reacted to form the compounds C2H5OSiH3 and C3H7OSiH3 (3) monosilane and diethyl ether are reacted to form the compound C2H5OSiH3 together with a high-boiling fraction containing the compound (H5C2O)2HSiOSiH(OC2H5)2; (4) monosilane and acetone are reacted to form the compound C3H7OSiH3; (5) monosilane and vinyl chloride are reacted to form a volatile portion containing compounds of the type R2SiHCl, RSiH2Cl and R3SiCl, where R represents CH3, C2H5 and C3H7; (6) monosilane and ethylene are reacted as in (1) and the compounds (C3H7)C2H5SiH2, Si2C9H24 and Si(C4H10)4 are additional compounds prepared; (7), (8) siloxene is reacted with pentane and with cyclohexane to form the compounds CH3SiH3, C2H5SiH3, (CH3)2SiH2 and (C2H5)2SiH2; (9) polymeric silicon dihydride and ethylene are reacted to form the products specified in (7). The following additional products are referred to: (C3H7)CH3Si (OC2H5)2, (C2H5)3(CH3)5Si3, (C2H5)6(CH3)4Si4, C3H7OSi(OC2H5)3 and C3H7OSi(OCH3)3.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE730379X | 1950-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB730379A true GB730379A (en) | 1955-05-25 |
Family
ID=6636588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24652/51A Expired GB730379A (en) | 1950-10-23 | 1951-10-22 | Method of preparing organic silicon compounds |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1054055A (en) |
| GB (1) | GB730379A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2909552A (en) * | 1956-07-13 | 1959-10-20 | Rhone Poulenc Sa | Process for the preparation of alkoxy and aralkoxy-methylpolysiloxanes |
| US3069451A (en) * | 1956-09-06 | 1962-12-18 | Fritz Gerhard | Preparation of organic silicon compounds |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2831011A (en) * | 1954-12-22 | 1958-04-15 | Dow Corning | Method of reacting silanes with ethers |
-
1951
- 1951-10-22 GB GB24652/51A patent/GB730379A/en not_active Expired
- 1951-10-23 FR FR1054055D patent/FR1054055A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2909552A (en) * | 1956-07-13 | 1959-10-20 | Rhone Poulenc Sa | Process for the preparation of alkoxy and aralkoxy-methylpolysiloxanes |
| US3069451A (en) * | 1956-09-06 | 1962-12-18 | Fritz Gerhard | Preparation of organic silicon compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1054055A (en) | 1954-02-08 |
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