JP2009513548A - 環状有機水素シロキサンの調製方法 - Google Patents
環状有機水素シロキサンの調製方法 Download PDFInfo
- Publication number
- JP2009513548A JP2009513548A JP2006519871A JP2006519871A JP2009513548A JP 2009513548 A JP2009513548 A JP 2009513548A JP 2006519871 A JP2006519871 A JP 2006519871A JP 2006519871 A JP2006519871 A JP 2006519871A JP 2009513548 A JP2009513548 A JP 2009513548A
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- JP
- Japan
- Prior art keywords
- cyclic
- hydrolyzate
- organohydrogensiloxane
- linear
- diluent
- 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.)
- Granted
Links
- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 32
- 239000003054 catalyst Substances 0.000 claims abstract description 28
- 239000003085 diluting agent Substances 0.000 claims abstract description 27
- 230000008707 rearrangement Effects 0.000 claims abstract description 26
- 230000002378 acidificating effect Effects 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910001868 water Inorganic materials 0.000 claims abstract description 14
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910000077 silane Inorganic materials 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 9
- -1 alkyl radicals Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 239000003701 inert diluent Substances 0.000 claims abstract description 6
- 150000002894 organic compounds Chemical group 0.000 claims abstract description 4
- 229920001843 polymethylhydrosiloxane Polymers 0.000 claims description 17
- 238000000926 separation method Methods 0.000 claims description 8
- 238000010924 continuous production Methods 0.000 claims description 5
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 238000006462 rearrangement reaction Methods 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000001335 aliphatic alkanes Chemical group 0.000 description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000005046 Chlorosilane Substances 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000011949 solid catalyst Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000005048 methyldichlorosilane Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012043 crude product Substances 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
- 230000007423 decrease Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000000892 gravimetry Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012188 paraffin wax Substances 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
- 230000035484 reaction time Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000004447 silicone coating Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
Images
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Silicon Polymers (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
(B)不活性液体希釈剤の存在下で、該加水分解物を酸性転位触媒と接触させ、該加水分解物中の該直鎖有機水素シロキサンに対する該環状有機水素シロキサンの割合を上昇させること
を含み、該酸性転位触媒が強酸基を含む有機化合物であり、該不活性液体希釈剤に溶解することを特徴とする、環状有機水素シロキサンの調製方法。
(C)直鎖メチル水素シロキサンと前記希釈剤とからの分離によって、環状メチル水素シロキサンを回収するステップ;ならびに
(D)ステップ(C)からステップ(B)まで、該直鎖メチル水素シロキサンと溶解された前記酸性転位触媒とを含む該希釈剤をリサイクルさせるステップ
を含む連続法として実施される。該有機酸性転位触媒はこのようにして、該不活性希釈剤と共に、転位(B)および分離(C)ステップを経て、連続的にリサイクルされる。
メチルジクロロシランCH3SiCl2を、化学量論的に当量の水、すなわちケイ素と結合した塩素1モルあたり0.5モルの水と、蒸気加熱連続加水分解反応容器内で混合した。該加水分解反応容器を60psigに維持し、該反応容器の温度を、該反応容器を出る加水分解物が約33℃の温度にあるように制御した。該反応容器を出る加水分解物を、水素炎イオン化検出器(FID)を使うガスクロマトグラフィー(GC)によって分析し、約95重量パーセントの直鎖塩素末端メチル水素シロキサン種と約5重量パーセントの環状メチル水素シロキサン種とを含むことが見出された。該加水分解物を、0.1%のドデシルベンゼンスルホン酸触媒を含む炭化水素溶媒「Isopar P」中約20%まで希釈した。該加水分解反応からの余剰分のHClガスを、再利用するために集めた。
Claims (6)
- (A)式RHSiCl2のシランで、Rがアリール基と1〜12の炭素原子を有するアルキル基とから選択されるシランを水と接触させ、環状有機水素シロキサンと直鎖有機水素シロキサンとを含む加水分解物を形成させること;ならびに
(B)不活性液体希釈剤の存在下で、該加水分解物を酸性転位触媒と接触させ、該加水分解物中の該直鎖有機水素シロキサンに対する該環状有機水素シロキサンの割合を上昇させること
を含み、該酸性転位触媒が強酸基を含む有機化合物であり、該不活性稀釈剤に溶解することを特徴とする、環状有機水素シロキサンの調製方法。 - 前記酸性転位触媒がスルホン酸であることを特徴とする、請求項1に記載の方法。
- 前記スルホン酸がアルキルアリールスルホン酸であることを特徴とする、請求項2に記載の方法。
- 前記スルホン酸がドデシルベンゼンスルホン酸であることを特徴とする、請求項3に記載の方法。
- 前記方法が:
(C)直鎖メチル水素シロキサンと前記希釈剤とからの分離によって、環状メチル水素シロキサンを回収するステップ;ならびに
(D)ステップ(C)からステップ(B)まで、該直鎖メチル水素シロキサンと溶解された前記酸性転位触媒とを含む該希釈剤をリサイクルさせるステップ
を含む連続法であることを特徴とする、請求項1〜4のいずれか1項に記載の方法。 - 前記希釈剤中の前記酸性転位触媒の濃度が0.05〜5重量%の範囲内であることを特徴とする、請求項1〜5のいずれか1項に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0316268.2A GB0316268D0 (en) | 2003-07-11 | 2003-07-11 | Process for preparing cyclic organohydrogensiloxanes |
PCT/EP2004/007805 WO2005005441A2 (en) | 2003-07-11 | 2004-07-02 | Process for preparing cyclic organohydrogensiloxanes |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009513548A true JP2009513548A (ja) | 2009-04-02 |
JP4482560B2 JP4482560B2 (ja) | 2010-06-16 |
Family
ID=27742005
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006519871A Active JP4482560B2 (ja) | 2003-07-11 | 2004-07-02 | 環状有機水素シロキサンの調製方法 |
Country Status (9)
Country | Link |
---|---|
US (1) | US7307179B2 (ja) |
EP (1) | EP1648907B1 (ja) |
JP (1) | JP4482560B2 (ja) |
CN (1) | CN100455588C (ja) |
AT (1) | ATE345348T1 (ja) |
BR (1) | BRPI0412505A (ja) |
DE (1) | DE602004003257T2 (ja) |
GB (1) | GB0316268D0 (ja) |
WO (1) | WO2005005441A2 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2021522156A (ja) * | 2018-05-02 | 2021-08-30 | イシラブズ サス | 水素キャリア化合物 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108164556B (zh) * | 2018-01-05 | 2020-12-08 | 王谌树 | 一种有机硅水解油连续裂解工艺 |
CN109233285A (zh) * | 2018-08-27 | 2019-01-18 | 扬中市惠丰包装有限公司 | 一种硅橡胶废料裂解回收再利用方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US527116A (en) * | 1894-10-09 | Pruning-tool | ||
US5196559A (en) | 1992-01-23 | 1993-03-23 | Dow Corning Corporation | Equilibration of cyclic siloxanes with novel catalysts |
US5247116A (en) * | 1992-07-10 | 1993-09-21 | Temple University Of The Commonwealth System Of Higher Education | Acid-catalyzed process for the production of cyclosiloxanes |
US5395956A (en) | 1994-07-05 | 1995-03-07 | Dow Corning Corporation | Process for preparing cyclic organohydrogensiloxanes |
US6534614B2 (en) * | 2001-04-04 | 2003-03-18 | General Electric Company | Process for the production of linear organohydrogensiloxanes |
-
2003
- 2003-07-11 GB GBGB0316268.2A patent/GB0316268D0/en not_active Ceased
-
2004
- 2004-07-02 EP EP04763219A patent/EP1648907B1/en active Active
- 2004-07-02 AT AT04763219T patent/ATE345348T1/de not_active IP Right Cessation
- 2004-07-02 CN CNB2004800197141A patent/CN100455588C/zh active Active
- 2004-07-02 JP JP2006519871A patent/JP4482560B2/ja active Active
- 2004-07-02 BR BRPI0412505-3A patent/BRPI0412505A/pt not_active Application Discontinuation
- 2004-07-02 US US10/559,956 patent/US7307179B2/en active Active
- 2004-07-02 DE DE602004003257T patent/DE602004003257T2/de active Active
- 2004-07-02 WO PCT/EP2004/007805 patent/WO2005005441A2/en active IP Right Grant
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2021522156A (ja) * | 2018-05-02 | 2021-08-30 | イシラブズ サス | 水素キャリア化合物 |
JP2021522157A (ja) * | 2018-05-02 | 2021-08-30 | イシラブズ サス | 水素キャリア化合物を生成及び再生するための方法 |
JP7374993B2 (ja) | 2018-05-02 | 2023-11-07 | イシラブズ サス | 水素キャリア化合物の再生のための方法 |
JP7429685B2 (ja) | 2018-05-02 | 2024-02-08 | イシラブズ サス | 水素の生成のための方法 |
Also Published As
Publication number | Publication date |
---|---|
EP1648907A2 (en) | 2006-04-26 |
US20060173202A1 (en) | 2006-08-03 |
WO2005005441A3 (en) | 2005-04-07 |
DE602004003257D1 (de) | 2006-12-28 |
CN1820015A (zh) | 2006-08-16 |
US7307179B2 (en) | 2007-12-11 |
DE602004003257T2 (de) | 2007-05-31 |
EP1648907B1 (en) | 2006-11-15 |
CN100455588C (zh) | 2009-01-28 |
BRPI0412505A (pt) | 2006-09-19 |
ATE345348T1 (de) | 2006-12-15 |
JP4482560B2 (ja) | 2010-06-16 |
WO2005005441A2 (en) | 2005-01-20 |
GB0316268D0 (en) | 2003-08-13 |
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