JPS58174390A - Ｎ−アリ−ルアミノアルキルアルコキシシランの製造方法 - Google Patents
Ｎ−アリ−ルアミノアルキルアルコキシシランの製造方法Info
- Publication number
- JPS58174390A JPS58174390A JP5762682A JP5762682A JPS58174390A JP S58174390 A JPS58174390 A JP S58174390A JP 5762682 A JP5762682 A JP 5762682A JP 5762682 A JP5762682 A JP 5762682A JP S58174390 A JPS58174390 A JP S58174390A
- Authority
- JP
- Japan
- Prior art keywords
- reaction product
- integer
- formula
- group
- less
- 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
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 16
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004508 fractional distillation Methods 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 abstract description 5
- 239000006087 Silane Coupling Agent Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 3
- 229920002554 vinyl polymer Polymers 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000007788 liquid Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 239000012433 hydrogen halide Substances 0.000 description 7
- 229910000039 hydrogen halide Inorganic materials 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- ARBWSQWFKWFAIW-UHFFFAOYSA-N (3-chloro-2-methylpropyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)CC(C)CCl ARBWSQWFKWFAIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012045 crude solution Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- -1 〇-toluidine Chemical compound 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- CASYTJWXPQRCFF-UHFFFAOYSA-N 2-chloroethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCl CASYTJWXPQRCFF-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 description 1
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 1
- KNTKCYKJRSMRMZ-UHFFFAOYSA-N 3-chloropropyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)CCCCl KNTKCYKJRSMRMZ-UHFFFAOYSA-N 0.000 description 1
- IFSSSYDVRQSDSG-UHFFFAOYSA-N 3-ethenylaniline Chemical compound NC1=CC=CC(C=C)=C1 IFSSSYDVRQSDSG-UHFFFAOYSA-N 0.000 description 1
- LBSXSAXOLABXMF-UHFFFAOYSA-N 4-Vinylaniline Chemical compound NC1=CC=C(C=C)C=C1 LBSXSAXOLABXMF-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- ZKQZJMVQJMMAFG-UHFFFAOYSA-N methanolate thorium(4+) Chemical compound [Th+4].C[O-].C[O-].C[O-].C[O-] ZKQZJMVQJMMAFG-UHFFFAOYSA-N 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
- 239000003607 modifier Substances 0.000 description 1
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 1
- HYQBDFDRGVBLHS-UHFFFAOYSA-N n-(2-methyl-3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CC(C)CNC1=CC=CC=C1 HYQBDFDRGVBLHS-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- CDZOGLJOFWFVOZ-UHFFFAOYSA-N n-propylaniline Chemical compound CCCNC1=CC=CC=C1 CDZOGLJOFWFVOZ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5762682A JPS58174390A (ja) | 1982-04-07 | 1982-04-07 | Ｎ−アリ−ルアミノアルキルアルコキシシランの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5762682A JPS58174390A (ja) | 1982-04-07 | 1982-04-07 | Ｎ−アリ−ルアミノアルキルアルコキシシランの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58174390A true JPS58174390A (ja) | 1983-10-13 |
| JPS6253516B2 JPS6253516B2 (enrdf_load_stackoverflow) | 1987-11-10 |
Family
ID=13061089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5762682A Granted JPS58174390A (ja) | 1982-04-07 | 1982-04-07 | Ｎ−アリ−ルアミノアルキルアルコキシシランの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58174390A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6429385A (en) * | 1987-07-27 | 1989-01-31 | Bridgestone Corp | Silane coupling agent |
| JPH0344394A (ja) * | 1989-07-12 | 1991-02-26 | Toray Dow Corning Silicone Co Ltd | 有機珪素化合物およびその製造方法 |
| CN102775433A (zh) * | 2012-04-08 | 2012-11-14 | 荆州市江汉精细化工有限公司 | 一种3-(苯基氨基)丙基烷氧基硅烷的制备及副产物的回收利用工艺 |
-
1982
- 1982-04-07 JP JP5762682A patent/JPS58174390A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6429385A (en) * | 1987-07-27 | 1989-01-31 | Bridgestone Corp | Silane coupling agent |
| JPH0344394A (ja) * | 1989-07-12 | 1991-02-26 | Toray Dow Corning Silicone Co Ltd | 有機珪素化合物およびその製造方法 |
| CN102775433A (zh) * | 2012-04-08 | 2012-11-14 | 荆州市江汉精细化工有限公司 | 一种3-(苯基氨基)丙基烷氧基硅烷的制备及副产物的回收利用工艺 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6253516B2 (enrdf_load_stackoverflow) | 1987-11-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5698726A (en) | Process for preparing amino-functional organosilanes low in or free of chloro-functional organosilanes | |
| JPH05186478A (ja) | 抑制されたアクリルオキシシラン及びメタクリルオキシシラン | |
| JPS5912117B2 (ja) | −ＣＳｘＣ−結合を有する硫化物の製造方法 | |
| US4045460A (en) | Preparation of aminoalkylsilanes | |
| RU2360917C2 (ru) | Способ получения (меркаптоорганил)алкоксисиланов | |
| US4152346A (en) | Beta-aminoethylsilanes and a method of preparing same | |
| JP2004256544A (ja) | 不飽和基を有する有機ケイ素化合物の安定化法 | |
| US3660443A (en) | Process for the alkylation of halogenated silicon and tin compounds | |
| JPS61263986A (ja) | 有機けい素化合物 | |
| DE60224678T2 (de) | Hochsiedende inhibitoren für destillierbare polymerisierbare monomere | |
| US3898255A (en) | Organosilicon compounds | |
| JP2530391B2 (ja) | 立体的に遮蔽されたアミノヒドロカルビルシラン類および製造方法 | |
| JPS58174390A (ja) | Ｎ−アリ−ルアミノアルキルアルコキシシランの製造方法 | |
| EP2876111B1 (en) | Composition containing nitrogen-containing organoxysilane compound and method for making the same | |
| DE1158071B (de) | Verfahren zur Herstellung von ª†-Aminoisobutylgruppen enthaltenden siliciumorganischen Verbindungen | |
| DE69309584T2 (de) | Alkoxysilane mit Azasilacycloalkylgruppe und Tetrametyldisiloxane mit Azasilacycloalkylgruppe | |
| EP0392509B1 (en) | 3-(2-Oxo-1-pyrrolidinyl)-propyl-silanes and method for preparing the silane compounds | |
| US4876363A (en) | Epoxy-containing organic silicon compounds | |
| US3919276A (en) | Method of preparing amines and amides | |
| US6475347B1 (en) | High boiling inhibitors for distillable, polymerizable monomers | |
| DE1154477B (de) | Verfahren zur Herstellung von Nitro- oder Nitritogruppen enthaltenden Silanen | |
| EP0408012B1 (en) | Organosilicon compounds and method for their preparation | |
| US20210079027A1 (en) | Silanes comprising oxamido ester groups | |
| US20250206889A1 (en) | Silicone-soluble acylphosphine oxide photoinitiator | |
| JPH05247062A (ja) | 有機けい素化合物 |