CA1048520A - Continuous process for producing polysiloxane oils utilizing a carbon black catalyst - Google Patents
Continuous process for producing polysiloxane oils utilizing a carbon black catalystInfo
- Publication number
- CA1048520A CA1048520A CA74211070A CA211070A CA1048520A CA 1048520 A CA1048520 A CA 1048520A CA 74211070 A CA74211070 A CA 74211070A CA 211070 A CA211070 A CA 211070A CA 1048520 A CA1048520 A CA 1048520A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst bed
- acid
- product stream
- water
- carbon black
- 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
- 239000003054 catalyst Substances 0.000 title claims abstract description 179
- 239000006229 carbon black Substances 0.000 title claims abstract description 46
- -1 polysiloxane Polymers 0.000 title claims abstract description 46
- 239000003921 oil Substances 0.000 title claims abstract description 29
- 238000010924 continuous production Methods 0.000 title claims abstract description 18
- 229920001296 polysiloxane Polymers 0.000 title claims description 14
- 239000000203 mixture Substances 0.000 claims abstract description 130
- 239000002253 acid Substances 0.000 claims abstract description 109
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 100
- 238000000034 method Methods 0.000 claims abstract description 89
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 66
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 62
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 claims abstract description 61
- 238000009835 boiling Methods 0.000 claims abstract description 31
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 16
- 239000012530 fluid Substances 0.000 claims abstract description 5
- 239000000047 product Substances 0.000 claims description 85
- 238000004821 distillation Methods 0.000 claims description 26
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000012467 final product Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 235000011149 sulphuric acid Nutrition 0.000 claims 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 abstract description 14
- 229910052753 mercury Inorganic materials 0.000 abstract description 14
- 241000872198 Serjania polyphylla Species 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 235000019241 carbon black Nutrition 0.000 description 57
- 238000006243 chemical reaction Methods 0.000 description 25
- 238000011067 equilibration Methods 0.000 description 22
- 230000007062 hydrolysis Effects 0.000 description 14
- 238000006460 hydrolysis reaction Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 8
- 239000003456 ion exchange resin Substances 0.000 description 8
- 229920003303 ion-exchange polymer Polymers 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 125000005372 silanol group Chemical group 0.000 description 7
- 238000010923 batch production Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000001282 organosilanes Chemical class 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 229940023913 cation exchange resins Drugs 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- FYBYQXQHBHTWLP-UHFFFAOYSA-N bis(silyloxysilyloxy)silane Chemical class [SiH3]O[SiH2]O[SiH2]O[SiH2]O[SiH3] FYBYQXQHBHTWLP-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- ACXIAEKDVUJRSK-UHFFFAOYSA-N methyl(silyloxy)silane Chemical compound C[SiH2]O[SiH3] ACXIAEKDVUJRSK-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000005386 organosiloxy group Chemical group 0.000 description 1
- LMAZKPOSWVOFGY-FBAUPLQOSA-N orine Natural products CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C)[C@H]4C[C@@H](OC(=O)C=Cc5ccccc5)[C@]6(C)[C@@](O)(CC[C@]6(O)[C@]4(O)CC=C3C2)[C@H](C)OC(=O)C=Cc7ccccc7)O[C@H](C)[C@H]1O LMAZKPOSWVOFGY-FBAUPLQOSA-N 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
Classifications
-
- 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
- C08G77/06—Preparatory processes
- C08G77/10—Equilibration processes
-
- 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
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00433095A US3853933A (en) | 1974-01-14 | 1974-01-14 | Continuous process for producing polysiloxane oils utilizing a carbon black catalyst |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1048520A true CA1048520A (en) | 1979-02-13 |
Family
ID=23718836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA74211070A Expired CA1048520A (en) | 1974-01-14 | 1974-10-09 | Continuous process for producing polysiloxane oils utilizing a carbon black catalyst |
Country Status (6)
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2357184A1 (de) * | 1973-11-16 | 1975-05-22 | Merck Patent Gmbh | Verfahren zur herstellung von organisch modifizierten siliciumdioxiden |
| DE2705563C2 (de) * | 1977-02-10 | 1982-10-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen Herstellung von hochviskosen Polydiorganosiloxanen |
| US4222952A (en) * | 1979-06-25 | 1980-09-16 | Union Carbide Corporation | Siloxane bond rearrangement effected by solid perfluorinated polymers containing pendant sulfonic acid groups |
| JPS6030713B2 (ja) * | 1981-07-27 | 1985-07-18 | 東芝シリコ−ン株式会社 | 被覆用組成物および被覆方法 |
| JPS6025062B2 (ja) * | 1981-07-27 | 1985-06-15 | 東芝シリコ−ン株式会社 | 成形方法 |
| US4683277A (en) * | 1986-07-02 | 1987-07-28 | Dow Corning Corporation | Method for preparing vinyl terminated fluorine-containing polydiorganosiloxane |
| US4831174A (en) * | 1987-12-31 | 1989-05-16 | Dow Corning Corporation | Production of polydiorganosiloxane fluids with low silanol content |
| DE3914912A1 (de) * | 1989-05-05 | 1990-11-08 | Wacker Chemie Gmbh | Verfahren zur kontinuierlichen herstellung von hochmolekularen organosiliciumverbindungen |
| US5408025A (en) * | 1993-07-15 | 1995-04-18 | General Electric Company | Synthesis of low silanol content, triorgano-stopped silicone fluids |
| US6316655B1 (en) * | 2001-02-20 | 2001-11-13 | Dow Corning Corporation | Method of making hydroxy end-terminated linear siloxanes |
| CZ2004904A3 (cs) * | 2002-02-25 | 2004-12-15 | Diffusion Pharmaceuticals Llc | Bipolární trans karotenoidní soli a jejich použití |
| US7759506B2 (en) * | 2002-02-25 | 2010-07-20 | Diffusion Pharmaceuticals Llc | Bipolar trans carotenoid salts and their uses |
| US7459103B2 (en) * | 2002-05-23 | 2008-12-02 | Columbian Chemicals Company | Conducting polymer-grafted carbon material for fuel cell applications |
| US7175930B2 (en) | 2002-05-23 | 2007-02-13 | Columbian Chemicals Company | Conducting polymer-grafted carbon material for fuel cell applications |
| ES2282630T3 (es) * | 2002-05-23 | 2007-10-16 | Columbian Chemicals Company | Material de carbono con polimero conductor sulfonado injertado para aplicaciones de pila de combustible. |
| US7390441B2 (en) * | 2002-05-23 | 2008-06-24 | Columbian Chemicals Company | Sulfonated conducting polymer-grafted carbon material for fuel cell applications |
| US7241334B2 (en) | 2002-05-23 | 2007-07-10 | Columbian Chemicals Company | Sulfonated carbonaceous materials |
| US7195834B2 (en) * | 2002-05-23 | 2007-03-27 | Columbian Chemicals Company | Metallized conducting polymer-grafted carbon material and method for making |
| US6958308B2 (en) | 2004-03-16 | 2005-10-25 | Columbian Chemicals Company | Deposition of dispersed metal particles onto substrates using supercritical fluids |
| US20060068987A1 (en) * | 2004-09-24 | 2006-03-30 | Srinivas Bollepalli | Carbon supported catalyst having reduced water retention |
| US7479566B2 (en) * | 2005-01-13 | 2009-01-20 | Dow Corning Corporation | Method for preparation of alkoxysilanes having reduced halide |
| JP2008531582A (ja) * | 2005-02-24 | 2008-08-14 | ディフュージョン・ファーマシューティカルズ・エルエルシー | トランスカロテノイド、それらの合成、配合、および使用 |
| US7696293B2 (en) * | 2005-05-23 | 2010-04-13 | Dow Corning Corporation | Method of neutralizing polysiloxanes containing acidic residuals |
| DE102007036069A1 (de) * | 2007-08-01 | 2009-02-05 | Wacker Chemie Ag | Mehrstufiges Verfahren zur Herstellung von Aminoalkylgruppen aufweisenden Organopolysiloxanen |
| JP5787884B2 (ja) | 2009-06-22 | 2015-09-30 | ディフュージョン・ファーマシューティカルズ・エルエルシー | 拡散増強化合物、及びその単独使用又は血栓溶解剤との併用 |
| CA2801292C (en) | 2010-06-02 | 2019-01-22 | Diffusion Pharmaceuticals Llc | Oral formulations of bipolar trans carotenoids |
| CN105384936B (zh) * | 2015-12-21 | 2019-03-05 | 山东东岳有机硅材料股份有限公司 | 一种多乙烯基硅油的制备方法 |
| CN115089569A (zh) | 2016-03-24 | 2022-09-23 | 扩散药品有限公司 | 双极性反式类胡萝卜素连同化疗和放射治疗在治疗癌症中的用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE756725A (fr) * | 1969-09-29 | 1971-03-29 | Dow Corning | Procede de preparation de 3,3,3-trifluoropropylmethylpolysiloxanes |
| US3714213A (en) * | 1971-01-06 | 1973-01-30 | Gen Electric | Method of making cyclopolysiloxanes containing silanic hydrogen |
| BE789272A (fr) * | 1971-09-29 | 1973-03-26 | Wacker Chemie Gmbh | Procede de preparation d'organosiloxanes |
-
1974
- 1974-01-14 US US00433095A patent/US3853933A/en not_active Expired - Lifetime
- 1974-10-09 CA CA74211070A patent/CA1048520A/en not_active Expired
- 1974-12-23 GB GB55513/74A patent/GB1488370A/en not_active Expired
-
1975
- 1975-01-11 DE DE19752500929 patent/DE2500929A1/de not_active Withdrawn
- 1975-01-14 FR FR7501016A patent/FR2257631B1/fr not_active Expired
- 1975-01-14 JP JP598775A patent/JPS5737606B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2500929A1 (de) | 1975-07-17 |
| FR2257631B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-02-26 |
| GB1488370A (en) | 1977-10-12 |
| JPS5737606B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-08-11 |
| US3853933A (en) | 1974-12-10 |
| FR2257631A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-08-08 |
| JPS50107099A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-08-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1048520A (en) | Continuous process for producing polysiloxane oils utilizing a carbon black catalyst | |
| CA1175185A (en) | Devolatilized rubber composition including a diorganosilanol chain stopped linear diorganopolysiloxane and a siloxane plasticizing fluid | |
| US4395563A (en) | Hydrolysis of alkoxysilanes | |
| CA1044246A (en) | Continuous process for producing polysiloxane oils | |
| US5384383A (en) | Pristine phenylpropylalkylsiloxanes | |
| US3903047A (en) | Process for the production of silanol-stopped diorgano-polysiloxanes | |
| US5420221A (en) | Process for the production of linear organosiloxane polymers by disproportionation | |
| US4111973A (en) | Process for producing a cyclotrisiloxane in a cracking reaction | |
| US4267298A (en) | Process for preparing M-stopped silicone fluids from silanol fluids | |
| CA1039735A (en) | Process for producing octaphenyltetracyclosiloxane | |
| CA1048521A (en) | Process for producing low and high molecular weight diorganopolysiloxanes for use in heat vulcanizable silicone rubber compositions | |
| US5075479A (en) | Anhydrous hydrogen chloride evolving one-step process for producing siloxanes | |
| US2983745A (en) | Silpropoxanes | |
| CA2030048A1 (en) | Nonaqueous method for making silicone oligomers | |
| GB2279960A (en) | Synthesis of low silanol content triorgano-stopped silicone fluids | |
| US3435001A (en) | Method for hydrolyzing organochlorosilanes | |
| KR100247162B1 (ko) | 폴리유기실록산으로부터 유기알콕시실란을 회수하는방법 | |
| US5488125A (en) | Method for manufacturing organosilanes having silanol groups | |
| US2863897A (en) | Method of preparing hydroxyl endblocked organopolysiloxane fluids | |
| US3135777A (en) | Process for preparing organosilicon copolymers | |
| GB2036770A (en) | Process for producing fluorosilicone polymers | |
| CA1285689C (en) | Process for chain stabilization of organopolysiloxanes | |
| US4272624A (en) | Process for producing high molecular weight diorganopolysiloxanes for use in heat vulcanizable silicone rubber compositions | |
| US5233070A (en) | Process for converting chlorine end-terminated polyorganosiloxanes to polyorganocyclosiloxanes | |
| US4238402A (en) | Reactions of chlorosilanes and methoxysilanes with chlorosiloxanes, methoxysiloxanes and siloxanes |