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)
| Country | Link |
|---|---|
| US (1) | US3853933A (enExample) |
| JP (1) | JPS5737606B2 (enExample) |
| CA (1) | CA1048520A (enExample) |
| DE (1) | DE2500929A1 (enExample) |
| FR (1) | FR2257631B1 (enExample) |
| GB (1) | GB1488370A (enExample) |
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 |
| AU2003215396B2 (en) * | 2002-02-25 | 2010-04-08 | Diffusion Pharmaceuticals Llc | Bipolar trans carotenoid salts and their uses |
| US7759506B2 (en) * | 2002-02-25 | 2010-07-20 | Diffusion Pharmaceuticals Llc | Bipolar trans carotenoid salts and their uses |
| US7390441B2 (en) * | 2002-05-23 | 2008-06-24 | Columbian Chemicals Company | Sulfonated conducting polymer-grafted carbon material for fuel cell applications |
| US7459103B2 (en) * | 2002-05-23 | 2008-12-02 | Columbian Chemicals Company | Conducting polymer-grafted carbon material for fuel cell applications |
| EA009404B1 (ru) | 2002-05-23 | 2007-12-28 | Коламбиан Кемикалз Компани | Углеродный материал с привитым проводящим полимером для применения в топливных элементах |
| US7241334B2 (en) | 2002-05-23 | 2007-07-10 | Columbian Chemicals Company | Sulfonated carbonaceous materials |
| DE60311985T2 (de) * | 2002-05-23 | 2007-10-25 | Columbian Chemicals Company | Sulfoniertes leitungs-graftpolymerkohlenstoffmaterial für brennstoffzellenanwendungen |
| 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 |
| EP1848757B1 (en) * | 2005-01-13 | 2008-08-13 | Dow Corning Corporation | Method of neutralizing polysiloxane hydrolyzates |
| 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 |
| KR101875843B1 (ko) | 2009-06-22 | 2018-07-06 | 디퓨젼 파마슈티컬즈 엘엘씨 | 확산 촉진 화합물 및 그 화합물 단독 또는 혈전 용해제와 합쳐진 화합물의 용도 |
| EP2575487B1 (en) | 2010-06-02 | 2017-10-18 | 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 |
| JP7032320B2 (ja) | 2016-03-24 | 2022-03-08 | 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 | 癌を処置するための、化学療法及び放射線療法を伴う二極性トランスカロテノイドの使用 |
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 |
|---|---|
| JPS50107099A (enExample) | 1975-08-23 |
| JPS5737606B2 (enExample) | 1982-08-11 |
| GB1488370A (en) | 1977-10-12 |
| FR2257631B1 (enExample) | 1982-02-26 |
| DE2500929A1 (de) | 1975-07-17 |
| US3853933A (en) | 1974-12-10 |
| FR2257631A1 (enExample) | 1975-08-08 |
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 | |
| US3937684A (en) | Process for producing high molecular weight diorganopolysiloxanes for use in heat vulcanizable silicone rubber compositions | |
| US4267298A (en) | Process for preparing M-stopped silicone fluids from silanol fluids | |
| CA1039735A (en) | Process for producing octaphenyltetracyclosiloxane | |
| US4111973A (en) | Process for producing a cyclotrisiloxane in a cracking reaction | |
| EP0515082B1 (en) | Anhydrous hydrogen chloride evolving one-step process for producing siloxanes | |
| 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 | |
| JP3513540B2 (ja) | ポリオルガノシロキサンからオルガノアルコキシシランを回収する方法 | |
| US5488125A (en) | Method for manufacturing organosilanes having silanol groups | |
| 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 | |
| US4281146A (en) | Method of neutralizing a halogen silicone compound | |
| US3813425A (en) | Process for producing polysiloxane useful as brake fluids | |
| US5194553A (en) | Process for preparation of organofunctional siloxanes | |
| US3398117A (en) | Process for the preparation of organopolysiloxanes |