JPS6112693A - N‐置換されたアミノアルキルシランの選択的製造方法 - Google Patents
N‐置換されたアミノアルキルシランの選択的製造方法Info
- Publication number
- JPS6112693A JPS6112693A JP60130928A JP13092885A JPS6112693A JP S6112693 A JPS6112693 A JP S6112693A JP 60130928 A JP60130928 A JP 60130928A JP 13092885 A JP13092885 A JP 13092885A JP S6112693 A JPS6112693 A JP S6112693A
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- catalyst
- psig
- substituted
- group
- 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
- -1 aminoalkyl silane Chemical class 0.000 title description 13
- 238000004519 manufacturing process Methods 0.000 title description 4
- 229910000077 silane Inorganic materials 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 58
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 55
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 43
- 239000003054 catalyst Substances 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 17
- 229910052697 platinum Inorganic materials 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 15
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052703 rhodium Inorganic materials 0.000 claims description 9
- 239000010948 rhodium Substances 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 25
- 239000000203 mixture Substances 0.000 description 24
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 20
- GBQYMXVQHATSCC-UHFFFAOYSA-N 3-triethoxysilylpropanenitrile Chemical compound CCO[Si](OCC)(OCC)CCC#N GBQYMXVQHATSCC-UHFFFAOYSA-N 0.000 description 19
- 238000001816 cooling Methods 0.000 description 19
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 18
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 16
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 9
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 8
- 150000003141 primary amines Chemical class 0.000 description 8
- 229910052759 nickel Inorganic materials 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 150000003335 secondary amines Chemical class 0.000 description 6
- KVUMYOWDFZAGPN-UHFFFAOYSA-N 3-trimethoxysilylpropanenitrile Chemical compound CO[Si](OC)(OC)CCC#N KVUMYOWDFZAGPN-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 150000001343 alkyl silanes Chemical class 0.000 description 5
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
- KHLWLJFRUQJJKQ-UHFFFAOYSA-N 3-trimethoxysilyl-n,n-bis(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCN(CCC[Si](OC)(OC)OC)CCC[Si](OC)(OC)OC KHLWLJFRUQJJKQ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical group NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical group NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- KFOZMMAXUUCIKU-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)butan-1-amine Chemical compound CCCCNCCC[Si](OCC)(OCC)OCC KFOZMMAXUUCIKU-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- ULRCHFVDUCOKTE-UHFFFAOYSA-N 3-[3-aminopropyl(diethoxy)silyl]oxybutan-1-amine Chemical compound NCCC[Si](OCC)(OCC)OC(C)CCN ULRCHFVDUCOKTE-UHFFFAOYSA-N 0.000 description 1
- ORCQSXBNGSJRCK-UHFFFAOYSA-N 3-[dibutoxy(ethyl)silyl]propanenitrile Chemical compound CCCCO[Si](CC)(CCC#N)OCCCC ORCQSXBNGSJRCK-UHFFFAOYSA-N 0.000 description 1
- DLVAOCLGJNRNQH-UHFFFAOYSA-N 3-[diheptoxy(methyl)silyl]propanenitrile Chemical compound CCCCCCCO[Si](C)(CCC#N)OCCCCCCC DLVAOCLGJNRNQH-UHFFFAOYSA-N 0.000 description 1
- CNWXYRUZMOWTCQ-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]-2-methylpropanenitrile Chemical compound CO[Si](C)(OC)CC(C)C#N CNWXYRUZMOWTCQ-UHFFFAOYSA-N 0.000 description 1
- QMVHDHTTYJSXSQ-UHFFFAOYSA-N 3-ethoxysilyl-N-(3-ethoxysilylpropyl)propan-1-amine Chemical compound CCO[SiH2]CCCNCCC[SiH2]OCC QMVHDHTTYJSXSQ-UHFFFAOYSA-N 0.000 description 1
- RLOOUDPAPLFWEJ-UHFFFAOYSA-N 3-methyl-4-triethoxysilylbutanenitrile Chemical compound CCO[Si](OCC)(OCC)CC(C)CC#N RLOOUDPAPLFWEJ-UHFFFAOYSA-N 0.000 description 1
- PFRLCKFENIXNMM-UHFFFAOYSA-N 3-trimethylsilylpropan-1-amine Chemical compound C[Si](C)(C)CCCN PFRLCKFENIXNMM-UHFFFAOYSA-N 0.000 description 1
- WJMGCQWMFIKKRK-UHFFFAOYSA-N 3-trioctoxysilylpropanenitrile Chemical compound CCCCCCCCO[Si](CCC#N)(OCCCCCCCC)OCCCCCCCC WJMGCQWMFIKKRK-UHFFFAOYSA-N 0.000 description 1
- YSEVGVGBHWFTIF-UHFFFAOYSA-N 4-[dimethoxy(methyl)silyl]butanenitrile Chemical compound CO[Si](C)(OC)CCCC#N YSEVGVGBHWFTIF-UHFFFAOYSA-N 0.000 description 1
- OGPMFEAJZWZWNX-UHFFFAOYSA-N 6-triethoxysilylhexanenitrile Chemical compound CCO[Si](OCC)(OCC)CCCCCC#N OGPMFEAJZWZWNX-UHFFFAOYSA-N 0.000 description 1
- PAUZTENZGRPWHA-UHFFFAOYSA-N C(#N)C=1C=C(C=CC1)CCOCO[SiH2]CC(C)C Chemical compound C(#N)C=1C=C(C=CC1)CCOCO[SiH2]CC(C)C PAUZTENZGRPWHA-UHFFFAOYSA-N 0.000 description 1
- 102100038590 Death-associated protein-like 1 Human genes 0.000 description 1
- 241000948268 Meda Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- OFLYIWITHZJFLS-UHFFFAOYSA-N [Si].[Au] Chemical compound [Si].[Au] OFLYIWITHZJFLS-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000009412 basement excavation Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 101150048696 dapL1 gene Proteins 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- IWCAQTQMDRGMPI-UHFFFAOYSA-N hexane-3,4-diamine Chemical compound CCC(N)C(N)CC IWCAQTQMDRGMPI-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- IKIPVSDFJVKSLQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)propane-1,3-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCCN IKIPVSDFJVKSLQ-UHFFFAOYSA-N 0.000 description 1
- ZOWYVOMEBLBBEB-UHFFFAOYSA-N n'-[3-[ethoxy(diethyl)silyl]propyl]ethane-1,2-diamine Chemical compound CCO[Si](CC)(CC)CCCNCCN ZOWYVOMEBLBBEB-UHFFFAOYSA-N 0.000 description 1
- QMIREOCYHAFOPK-UHFFFAOYSA-N n,n'-bis(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCNCCC[Si](OCC)(OCC)OCC QMIREOCYHAFOPK-UHFFFAOYSA-N 0.000 description 1
- YFBFAHMPVMWKIM-UHFFFAOYSA-N n-(3-triethoxysilylpropyl)cyclohexanamine Chemical compound CCO[Si](OCC)(OCC)CCCNC1CCCCC1 YFBFAHMPVMWKIM-UHFFFAOYSA-N 0.000 description 1
- CEZKFSFZWCXHHJ-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)octan-1-amine Chemical compound CCCCCCCCNCCC[Si](OC)(OC)OC CEZKFSFZWCXHHJ-UHFFFAOYSA-N 0.000 description 1
- QHCCDDQKNUYGNC-UHFFFAOYSA-N n-ethylbutan-1-amine Chemical compound CCCCNCC QHCCDDQKNUYGNC-UHFFFAOYSA-N 0.000 description 1
- XPVLBUSTQISKRM-UHFFFAOYSA-N n-methyl-n-(3-triethoxysilylpropyl)butan-1-amine Chemical compound CCCCN(C)CCC[Si](OCC)(OCC)OCC XPVLBUSTQISKRM-UHFFFAOYSA-N 0.000 description 1
- SEGJNMCIMOLEDM-UHFFFAOYSA-N n-methyloctan-1-amine Chemical compound CCCCCCCCNC SEGJNMCIMOLEDM-UHFFFAOYSA-N 0.000 description 1
- CLDVQCMGOSGNIW-UHFFFAOYSA-N nickel tin Chemical compound [Ni].[Sn] CLDVQCMGOSGNIW-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 108010088694 phosphoserine aminotransferase Proteins 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- CQERQNNEKFKVFU-UHFFFAOYSA-N triethoxy(3-piperazin-1-ylpropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN1CCNCC1 CQERQNNEKFKVFU-UHFFFAOYSA-N 0.000 description 1
- AOKNSKHTJMRBHF-UHFFFAOYSA-N triethoxy-[3-[4-(3-triethoxysilylpropyl)piperazin-1-yl]propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCN1CCN(CCC[Si](OCC)(OCC)OCC)CC1 AOKNSKHTJMRBHF-UHFFFAOYSA-N 0.000 description 1
- HXYMWKLNCJPAKW-UHFFFAOYSA-N trimethoxy(3-piperazin-1-ylpropyl)silane Chemical compound CO[Si](OC)(OC)CCCN1CCNCC1 HXYMWKLNCJPAKW-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US622176 | 1984-06-19 | ||
US06/622,176 US4526996A (en) | 1984-06-19 | 1984-06-19 | Process for the preparation of N-substituted aminoalkylsilanes |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6112693A true JPS6112693A (ja) | 1986-01-21 |
JPS6330313B2 JPS6330313B2 (US08088918-20120103-C00476.png) | 1988-06-17 |
Family
ID=24493203
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP60130928A Granted JPS6112693A (ja) | 1984-06-19 | 1985-06-18 | N‐置換されたアミノアルキルシランの選択的製造方法 |
Country Status (7)
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62185091A (ja) * | 1986-01-30 | 1987-08-13 | ダウ・コ−ニング・リミテツド | 第1級アミノシロシサンの製造方法 |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4618689A (en) * | 1985-07-18 | 1986-10-21 | General Electric Company | Novel aminofunctional silicone compositions |
US5075475A (en) * | 1989-06-14 | 1991-12-24 | Hughes Aircraft Company | Aromatic polyimide silanol compounds, precursors and polymers thereof |
JPH0314105U (US08088918-20120103-C00476.png) * | 1989-06-28 | 1991-02-13 | ||
US5329039A (en) * | 1990-11-01 | 1994-07-12 | Shin-Etsu Chemical Co., Ltd. | Organosilicon compound |
US5117024A (en) * | 1991-08-06 | 1992-05-26 | Dow Corning Corporation | Process for preparation of primary aminoorganosilanes |
US5101055A (en) * | 1991-09-09 | 1992-03-31 | Dow Corning Corporation | Process for preparation of bis- and tris(silylorgano)amines |
US5300641A (en) * | 1993-01-08 | 1994-04-05 | Dow Corning Corporation | Palladium black catalyzed process for preparation of (piperazinylorgano) silanes |
US6262216B1 (en) | 1998-10-13 | 2001-07-17 | Affymetrix, Inc. | Functionalized silicon compounds and methods for their synthesis and use |
US6228496B1 (en) | 1999-05-26 | 2001-05-08 | Ppg Industries Ohio, Inc. | Sizing composition for glass fibers |
CN1630744A (zh) * | 2001-09-07 | 2005-06-22 | 博登化学公司 | 使用粘合促进剂的涂覆光纤及其制备和使用方法 |
US6417381B1 (en) * | 2001-11-15 | 2002-07-09 | Crompton Corporation | Process for preparing bis(silylorgano)amines |
US7410691B2 (en) * | 2001-12-27 | 2008-08-12 | Ppg Industries Ohio, Inc. | Photochromic optical article |
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DE102008002183A1 (de) * | 2008-06-03 | 2009-12-10 | Evonik Degussa Gmbh | Verfahren zur Aufarbeitung salzhaltiger Rückstände aus der Herstellung von aminofunktionellen Organosilanen |
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DE102009002477A1 (de) | 2009-04-20 | 2010-10-21 | Evonik Degussa Gmbh | Quartäre-aminofunktionelle, siliciumorganische Verbindungen enthaltende Zusammensetzung sowie deren Herstellung und Verwendung |
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US3033815A (en) * | 1959-08-28 | 1962-05-08 | Union Carbide Corp | Organosilicon compounds and process for producing same |
US3046295A (en) * | 1960-06-21 | 1962-07-24 | Union Carbide Corp | Process for producing aminoalkylsilanes |
DE2521399A1 (de) * | 1975-05-14 | 1976-11-25 | Bayer Ag | Verfahren zur herstellung von aminoalkylsilanen |
GB2080285B (en) * | 1980-07-23 | 1984-08-15 | Ciba Geigy Ag | Process for the preparation of cyclopropylmethyl-n-propylamine |
-
1984
- 1984-06-19 US US06/622,176 patent/US4526996A/en not_active Expired - Lifetime
-
1985
- 1985-04-30 IN IN331/MAS/85A patent/IN164744B/en unknown
- 1985-05-01 CA CA000480554A patent/CA1235701A/en not_active Expired
- 1985-06-18 AT AT85107515T patent/ATE40372T1/de not_active IP Right Cessation
- 1985-06-18 EP EP85107515A patent/EP0167887B1/en not_active Expired
- 1985-06-18 JP JP60130928A patent/JPS6112693A/ja active Granted
- 1985-06-18 DE DE8585107515T patent/DE3567872D1/de not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62185091A (ja) * | 1986-01-30 | 1987-08-13 | ダウ・コ−ニング・リミテツド | 第1級アミノシロシサンの製造方法 |
Also Published As
Publication number | Publication date |
---|---|
EP0167887A1 (en) | 1986-01-15 |
EP0167887B1 (en) | 1989-01-25 |
CA1235701A (en) | 1988-04-26 |
ATE40372T1 (de) | 1989-02-15 |
JPS6330313B2 (US08088918-20120103-C00476.png) | 1988-06-17 |
IN164744B (US08088918-20120103-C00476.png) | 1989-05-20 |
US4526996A (en) | 1985-07-02 |
DE3567872D1 (en) | 1989-03-02 |
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