JPS6121478B2 - - Google Patents
Info
- Publication number
- JPS6121478B2 JPS6121478B2 JP14634478A JP14634478A JPS6121478B2 JP S6121478 B2 JPS6121478 B2 JP S6121478B2 JP 14634478 A JP14634478 A JP 14634478A JP 14634478 A JP14634478 A JP 14634478A JP S6121478 B2 JPS6121478 B2 JP S6121478B2
- Authority
- JP
- Japan
- Prior art keywords
- trimethoxysilane
- reaction mixture
- methyl alcohol
- phosphorus compound
- organic phosphorus
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 claims description 32
- 239000011541 reaction mixture Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 12
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 229910052802 copper Inorganic materials 0.000 claims description 9
- 239000010949 copper Substances 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- 230000000087 stabilizing effect Effects 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 238000004821 distillation Methods 0.000 description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 11
- -1 didodezylbenzene Chemical compound 0.000 description 10
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- FTPPZZQMHSLCST-UHFFFAOYSA-N 1,2,3-tripropylnaphthalene Chemical compound C1=CC=C2C(CCC)=C(CCC)C(CCC)=CC2=C1 FTPPZZQMHSLCST-UHFFFAOYSA-N 0.000 description 1
- WSSNQXJVTQOUMV-UHFFFAOYSA-N 1,2-dibenzyl-3,4-dimethylbenzene Chemical group C=1C=CC=CC=1CC1=C(C)C(C)=CC=C1CC1=CC=CC=C1 WSSNQXJVTQOUMV-UHFFFAOYSA-N 0.000 description 1
- PKQYSCBUFZOAPE-UHFFFAOYSA-N 1,2-dibenzyl-3-methylbenzene Chemical compound C=1C=CC=CC=1CC=1C(C)=CC=CC=1CC1=CC=CC=C1 PKQYSCBUFZOAPE-UHFFFAOYSA-N 0.000 description 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical compound C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- KXTWDIPAGFPHCA-UHFFFAOYSA-N 1,2-dipropylnaphthalene Chemical compound C1=CC=CC2=C(CCC)C(CCC)=CC=C21 KXTWDIPAGFPHCA-UHFFFAOYSA-N 0.000 description 1
- HMPKHOSFFRHDAG-UHFFFAOYSA-N 1-diphenoxyphosphanylethyl(diphenoxy)phosphane Chemical compound O(C1=CC=CC=C1)P(OC1=CC=CC=C1)C(C)P(OC1=CC=CC=C1)OC1=CC=CC=C1 HMPKHOSFFRHDAG-UHFFFAOYSA-N 0.000 description 1
- UAXNXOMKCGKNCI-UHFFFAOYSA-N 1-diphenylphosphanylethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 UAXNXOMKCGKNCI-UHFFFAOYSA-N 0.000 description 1
- HMAMGXMFMCAOPV-UHFFFAOYSA-N 1-propylnaphthalene Chemical compound C1=CC=C2C(CCC)=CC=CC2=C1 HMAMGXMFMCAOPV-UHFFFAOYSA-N 0.000 description 1
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000013522 chelant Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- ZKXWKVVCCTZOLD-UHFFFAOYSA-N copper;4-hydroxypent-3-en-2-one Chemical compound [Cu].CC(O)=CC(C)=O.CC(O)=CC(C)=O ZKXWKVVCCTZOLD-UHFFFAOYSA-N 0.000 description 1
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 229940076286 cupric acetate Drugs 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- 229940112669 cuprous oxide Drugs 0.000 description 1
- 229930007927 cymene Natural products 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- LVTCZSBUROAWTE-UHFFFAOYSA-N diethyl(phenyl)phosphane Chemical compound CCP(CC)C1=CC=CC=C1 LVTCZSBUROAWTE-UHFFFAOYSA-N 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002366 halogen compounds Chemical class 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14634478A JPS5572198A (en) | 1978-11-27 | 1978-11-27 | Stabilization of trimethoxysilane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14634478A JPS5572198A (en) | 1978-11-27 | 1978-11-27 | Stabilization of trimethoxysilane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5572198A JPS5572198A (en) | 1980-05-30 |
| JPS6121478B2 true JPS6121478B2 (https=) | 1986-05-27 |
Family
ID=15405572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14634478A Granted JPS5572198A (en) | 1978-11-27 | 1978-11-27 | Stabilization of trimethoxysilane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5572198A (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4727173A (en) * | 1987-03-31 | 1988-02-23 | Union Carbide Corporation | Process for producing trialkoxysilanes from the reaction of silicon metal and alcohol |
| US4761492A (en) * | 1987-09-28 | 1988-08-02 | Union Carbide Corporation | Process for recovering trimethoxysilane from a trimethoxysilane and methanol mixture |
| JP4397647B2 (ja) | 2003-07-30 | 2010-01-13 | 東レ・ダウコーニング株式会社 | ヒドロアルコキシシランの安定化剤、安定化方法および安定化されたヒドロアルコキシシラン |
| US7652164B2 (en) * | 2005-09-13 | 2010-01-26 | Momentive Performance Materials Inc. | Process for the direct synthesis of trialkoxysilane |
-
1978
- 1978-11-27 JP JP14634478A patent/JPS5572198A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5572198A (en) | 1980-05-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7684409B2 (ja) | 有機スズ化合物を調製する方法 | |
| CN116897158A (zh) | 制备有机锡化合物的方法 | |
| CA2223677A1 (en) | Metal complex source reagents for chemical vapor deposition | |
| JP2014511380A (ja) | Ｎ−アミノアミジナート配位子を有する金属錯体 | |
| US11028108B2 (en) | Method for producing dialkylaminosilane | |
| CN101909443B (zh) | 饱和咪唑啉鎓盐及相关化合物的制备 | |
| EP0527661A1 (en) | Metal beta-diketonates | |
| JPS6121478B2 (https=) | ||
| US4467105A (en) | Method of preparing glycol esters of organosilanes | |
| US8680289B2 (en) | Complexes of imidazole ligands | |
| JPS6145632B2 (https=) | ||
| JP4560484B2 (ja) | メタロセン化合物製造方法 | |
| JPS633869B2 (https=) | ||
| JPH1149780A (ja) | 無機フィルムコーティング及び粉末用オルガノ金属性単一ソースプリカーサー | |
| CN110691785B (zh) | 在羧酸盐存在下的三烷基铟化合物的生产 | |
| JP5529591B2 (ja) | 多座β−ケトイミネートの金属錯体の調製方法 | |
| JPS6139955B2 (https=) | ||
| JPS6121477B2 (https=) | ||
| JP2019048744A (ja) | ジフルオロリン酸リチウムの製造方法 | |
| KR102080218B1 (ko) | 이중치환 사이클로펜타디엔 화합물, 유기금속 화합물 및 그 제조방법 | |
| CN115698028B (zh) | 用于生产特定α,β-不饱和羧酸酯的改进方法 | |
| JP7767333B2 (ja) | リン化合物の精製方法および再利用方法 | |
| JPH0137397B2 (https=) | ||
| US3317571A (en) | Tris(n, n-dimethylformamide)molybdenum tricarbonyl and process for preparing same | |
| JPH0613536B2 (ja) | 降下した氷点を有するチタニウムエステル組成物とその製法 |