TWI540138B - 有機胺基矽烷及其製造方法 - Google Patents
有機胺基矽烷及其製造方法 Download PDFInfo
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- TWI540138B TWI540138B TW104105880A TW104105880A TWI540138B TW I540138 B TWI540138 B TW I540138B TW 104105880 A TW104105880 A TW 104105880A TW 104105880 A TW104105880 A TW 104105880A TW I540138 B TWI540138 B TW I540138B
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- Prior art keywords
- group
- organic amine
- alkyl
- dioxane
- linear
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- 238000000034 method Methods 0.000 title claims description 61
- 150000001412 amines Chemical class 0.000 claims description 82
- -1 C 3-10 cyclic alkyl Chemical group 0.000 claims description 74
- 150000002466 imines Chemical class 0.000 claims description 63
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 54
- 239000003054 catalyst Substances 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000003277 amino group Chemical group 0.000 claims description 41
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 20
- 150000004820 halides Chemical class 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 13
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 12
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 10
- IXTNDEVVXTYVHI-UHFFFAOYSA-N 1,4-dioxan-2-amine Chemical compound NC1COCCO1 IXTNDEVVXTYVHI-UHFFFAOYSA-N 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 7
- PQLXPSPUHFTNJD-UHFFFAOYSA-N CC(C)N(C(C)C)C1COCCO1 Chemical compound CC(C)N(C(C)C)C1COCCO1 PQLXPSPUHFTNJD-UHFFFAOYSA-N 0.000 claims description 5
- KKBBWXXPTRIVMP-UHFFFAOYSA-N CCCCCCCCCC.[C] Chemical compound CCCCCCCCCC.[C] KKBBWXXPTRIVMP-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004967 formylalkyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 4
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- 125000003800 germyl group Chemical group [H][Ge]([H])([H])[*] 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000007848 Bronsted acid Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- HMDDXIMCDZRSNE-UHFFFAOYSA-N [C].[Si] Chemical compound [C].[Si] HMDDXIMCDZRSNE-UHFFFAOYSA-N 0.000 claims description 2
- CGERRFWFPVRKGJ-UHFFFAOYSA-N C(C)(C)N(C1CCCCC1)C1OCCOC1 Chemical compound C(C)(C)N(C1CCCCC1)C1OCCOC1 CGERRFWFPVRKGJ-UHFFFAOYSA-N 0.000 claims 2
- HQZKIRGIEUIZRQ-UHFFFAOYSA-N C(C)N(C1CCCCC1)C1OCCOC1 Chemical compound C(C)N(C1CCCCC1)C1OCCOC1 HQZKIRGIEUIZRQ-UHFFFAOYSA-N 0.000 claims 2
- WTDZZNGKSXCWQM-UHFFFAOYSA-N CC(C)N(C1CCCC1)C2COCCO2 Chemical compound CC(C)N(C1CCCC1)C2COCCO2 WTDZZNGKSXCWQM-UHFFFAOYSA-N 0.000 claims 2
- KZPGTQAIIREOHO-UHFFFAOYSA-N CCCCCCCCCC(C)N(C(C)C)C(C)C Chemical compound CCCCCCCCCC(C)N(C(C)C)C(C)C KZPGTQAIIREOHO-UHFFFAOYSA-N 0.000 claims 2
- QCNONTNBINMOSU-UHFFFAOYSA-N CCCCCCCCCC(C)N(CCC)C(C)C Chemical compound CCCCCCCCCC(C)N(CCC)C(C)C QCNONTNBINMOSU-UHFFFAOYSA-N 0.000 claims 2
- QYSYRZGBYNVFAF-UHFFFAOYSA-N CCCCCCCCCC(C1=CC=CC=C1)N(CC)CC Chemical compound CCCCCCCCCC(C1=CC=CC=C1)N(CC)CC QYSYRZGBYNVFAF-UHFFFAOYSA-N 0.000 claims 2
- OIYFYXWLADIRCQ-UHFFFAOYSA-N CCCN(C1CCCC1)C2COCCO2 Chemical compound CCCN(C1CCCC1)C2COCCO2 OIYFYXWLADIRCQ-UHFFFAOYSA-N 0.000 claims 2
- SMFIBVAANHXYLL-UHFFFAOYSA-N CN(C1CCCCC1)C1OCCOC1 Chemical compound CN(C1CCCCC1)C1OCCOC1 SMFIBVAANHXYLL-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- ITWKOSPCIDASSJ-UHFFFAOYSA-N 2-butyl-1,4-dioxan-2-amine Chemical compound CCCCC1(COCCO1)N ITWKOSPCIDASSJ-UHFFFAOYSA-N 0.000 claims 1
- WLFHGUQGFOANGU-UHFFFAOYSA-N CCCCC1(COCCO1)NC(C)C Chemical compound CCCCC1(COCCO1)NC(C)C WLFHGUQGFOANGU-UHFFFAOYSA-N 0.000 claims 1
- CVSCZSRLSPHCKC-UHFFFAOYSA-N CCCCC1(NC2CCCC2)OCCOC1 Chemical compound CCCCC1(NC2CCCC2)OCCOC1 CVSCZSRLSPHCKC-UHFFFAOYSA-N 0.000 claims 1
- YRZWCSCIVHULKQ-UHFFFAOYSA-N CCCCCCCCCC(C)N(C1CCCCC1)C(C)C Chemical compound CCCCCCCCCC(C)N(C1CCCCC1)C(C)C YRZWCSCIVHULKQ-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 claims 1
- 125000002704 decyl 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])* 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 description 34
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 229910052707 ruthenium Inorganic materials 0.000 description 17
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 150000003335 secondary amines Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 239000012467 final product Substances 0.000 description 8
- 239000010936 titanium Substances 0.000 description 8
- 229910000420 cerium oxide Inorganic materials 0.000 description 7
- 108700039708 galantide Proteins 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 238000006459 hydrosilylation reaction Methods 0.000 description 6
- 229910052747 lanthanoid Inorganic materials 0.000 description 6
- 150000002602 lanthanoids Chemical class 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 150000002012 dioxanes Chemical class 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 229910052987 metal hydride Inorganic materials 0.000 description 5
- 150000004681 metal hydrides Chemical class 0.000 description 5
- RDNMOYZEMHOLIF-UHFFFAOYSA-N n,n-di(propan-2-yl)decan-1-amine Chemical compound CCCCCCCCCCN(C(C)C)C(C)C RDNMOYZEMHOLIF-UHFFFAOYSA-N 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 150000003624 transition metals Chemical class 0.000 description 5
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 4
- XGCDBGRZEKYHNV-UHFFFAOYSA-N 1,1-bis(diphenylphosphino)methane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CP(C=1C=CC=CC=1)C1=CC=CC=C1 XGCDBGRZEKYHNV-UHFFFAOYSA-N 0.000 description 4
- RPDFRSKJKOQCIT-UHFFFAOYSA-N 3-ethyldodecane Chemical compound CCCCCCCCCC(CC)CC RPDFRSKJKOQCIT-UHFFFAOYSA-N 0.000 description 4
- UWXGNVIWGYPJIB-UHFFFAOYSA-N CCCCCCCCCC(CC)(CC)N(CCC)CCC Chemical compound CCCCCCCCCC(CC)(CC)N(CCC)CCC UWXGNVIWGYPJIB-UHFFFAOYSA-N 0.000 description 4
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 230000005588 protonation Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 4
- RMFRFTSSEHRKKW-UHFFFAOYSA-N 1,2-bis(diisopropylphosphino)ethane Chemical compound CC(C)P(C(C)C)CCP(C(C)C)C(C)C RMFRFTSSEHRKKW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052777 Praseodymium Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- UCJOAMOXKLJGST-UHFFFAOYSA-N n-propan-2-ylpropan-2-imine Chemical compound CC(C)N=C(C)C UCJOAMOXKLJGST-UHFFFAOYSA-N 0.000 description 3
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- PFCIJALLGNUKRS-UHFFFAOYSA-N (3-diphenylphosphanyloxyphenoxy)-diphenylphosphane Chemical compound C=1C=CC(OP(C=2C=CC=CC=2)C=2C=CC=CC=2)=CC=1OP(C=1C=CC=CC=1)C1=CC=CC=C1 PFCIJALLGNUKRS-UHFFFAOYSA-N 0.000 description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
- GFAJOMHUNNCCJQ-UHFFFAOYSA-N 1,3-dioxetane Chemical compound C1OCO1 GFAJOMHUNNCCJQ-UHFFFAOYSA-N 0.000 description 2
- XUJAWKUTXXAZHE-UHFFFAOYSA-N 2-n,4-n-bis[2,6-di(propan-2-yl)phenyl]pentane-2,4-diamine Chemical compound CC(C)C=1C=CC=C(C(C)C)C=1NC(C)CC(C)NC1=C(C(C)C)C=CC=C1C(C)C XUJAWKUTXXAZHE-UHFFFAOYSA-N 0.000 description 2
- ADKIPZOCWDDVCY-UHFFFAOYSA-N C(C)(C)N(C(C)C)C(CCCCCCCCC)C1=CC=CC=C1 Chemical compound C(C)(C)N(C(C)C)C(CCCCCCCCC)C1=CC=CC=C1 ADKIPZOCWDDVCY-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- 229910052692 Dysprosium Inorganic materials 0.000 description 2
- 229910052691 Erbium Inorganic materials 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 229910052689 Holmium Inorganic materials 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910052779 Neodymium Inorganic materials 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052772 Samarium Inorganic materials 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910052771 Terbium Inorganic materials 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910052775 Thulium Inorganic materials 0.000 description 2
- 229910052770 Uranium Inorganic materials 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- UOFFEDRAIFYOBS-UHFFFAOYSA-N butan-1-imine Chemical compound CCCC=N UOFFEDRAIFYOBS-UHFFFAOYSA-N 0.000 description 2
- DBVOFADAKBQYJA-UHFFFAOYSA-N butane 1,4-dioxane Chemical compound O1CCOCC1.CCCC DBVOFADAKBQYJA-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- UZILCZKGXMQEQR-UHFFFAOYSA-N decyl-Benzene Chemical compound CCCCCCCCCCC1=CC=CC=C1 UZILCZKGXMQEQR-UHFFFAOYSA-N 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- KZZFGAYUBYCTNX-UHFFFAOYSA-N diethylsilicon Chemical compound CC[Si]CC KZZFGAYUBYCTNX-UHFFFAOYSA-N 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052746 lanthanum Inorganic materials 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- AIYYMMQIMJOTBM-UHFFFAOYSA-L nickel(ii) acetate Chemical compound [Ni+2].CC([O-])=O.CC([O-])=O AIYYMMQIMJOTBM-UHFFFAOYSA-L 0.000 description 2
- 229910052758 niobium Inorganic materials 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910052702 rhenium Inorganic materials 0.000 description 2
- 229910052706 scandium Inorganic materials 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
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- FRCFWPVMFJMNDP-UHFFFAOYSA-N n-propan-2-ylaniline Chemical group CC(C)NC1=CC=CC=C1 FRCFWPVMFJMNDP-UHFFFAOYSA-N 0.000 description 1
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- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 1
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- RJQWVEJVXWLMRE-UHFFFAOYSA-N platinum;tritert-butylphosphane Chemical compound [Pt].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C RJQWVEJVXWLMRE-UHFFFAOYSA-N 0.000 description 1
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- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 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
- C07F7/025—Silicon compounds without C-silicon linkages
-
- 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
- C07F7/0801—General processes
-
- 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
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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
- C07F7/12—Organo silicon halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| US201461946164P | 2014-02-28 | 2014-02-28 | |
| US14/625,158 US9233990B2 (en) | 2014-02-28 | 2015-02-18 | Organoaminosilanes and methods for making same |
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| TW201533051A TW201533051A (zh) | 2015-09-01 |
| TWI540138B true TWI540138B (zh) | 2016-07-01 |
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| TW104105880A TWI540138B (zh) | 2014-02-28 | 2015-02-24 | 有機胺基矽烷及其製造方法 |
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| EP (2) | EP2913334B1 (cg-RX-API-DMAC7.html) |
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| CN (1) | CN104876957B (cg-RX-API-DMAC7.html) |
| TW (1) | TWI540138B (cg-RX-API-DMAC7.html) |
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| US10453675B2 (en) * | 2013-09-20 | 2019-10-22 | Versum Materials Us, Llc | Organoaminosilane precursors and methods for depositing films comprising same |
| CN105849221B (zh) | 2013-09-27 | 2019-06-18 | 乔治洛德方法研究和开发液化空气有限公司 | 胺取代的三甲硅烷基胺和三-二甲硅烷基胺化合物 |
| US9233990B2 (en) * | 2014-02-28 | 2016-01-12 | Air Products And Chemicals, Inc. | Organoaminosilanes and methods for making same |
| US9969756B2 (en) | 2014-09-23 | 2018-05-15 | L'Air Liquide, Société Anonyme pour l'Etude et l'Exploitation des Procédés George Claude | Carbosilane substituted amine precursors for deposition of Si-containing films and methods thereof |
| US10354860B2 (en) * | 2015-01-29 | 2019-07-16 | Versum Materials Us, Llc | Method and precursors for manufacturing 3D devices |
| US9777025B2 (en) | 2015-03-30 | 2017-10-03 | L'Air Liquide, Société pour l'Etude et l'Exploitation des Procédés Georges Claude | Si-containing film forming precursors and methods of using the same |
| TWI716333B (zh) * | 2015-03-30 | 2021-01-11 | 法商液態空氣喬治斯克勞帝方法研究開發股份有限公司 | 碳矽烷與氨、胺類及脒類之觸媒去氫耦合 |
| WO2016205196A2 (en) * | 2015-06-16 | 2016-12-22 | Air Products And Chemicals, Inc. | Halidosilane compounds and compositions and processes for depositing silicon-containing films using same |
| US11111256B2 (en) * | 2015-12-18 | 2021-09-07 | Jiangsu Nata Opto-Electronic Materials Co. Ltd. | High purity trisilylamine, methods of making, and use |
| US9701695B1 (en) * | 2015-12-30 | 2017-07-11 | American Air Liquide, Inc. | Synthesis methods for amino(halo)silanes |
| US10053775B2 (en) | 2015-12-30 | 2018-08-21 | L'air Liquide, Societé Anonyme Pour L'etude Et L'exploitation Des Procédés Georges Claude | Methods of using amino(bromo)silane precursors for ALD/CVD silicon-containing film applications |
| TWI724141B (zh) | 2016-03-23 | 2021-04-11 | 法商液態空氣喬治斯克勞帝方法硏究開發股份有限公司 | 形成含矽膜之組成物及其製法與用途 |
| US10464953B2 (en) * | 2016-10-14 | 2019-11-05 | Versum Materials Us, Llc | Carbon bridged aminosilane compounds for high growth rate silicon-containing films |
| US11735413B2 (en) * | 2016-11-01 | 2023-08-22 | Versum Materials Us, Llc | Precursors and flowable CVD methods for making low-k films to fill surface features |
| JP7100036B2 (ja) * | 2016-12-27 | 2022-07-12 | ナタ セミコンダクター マテリアルズ カンパニー リミテッド | アミンとシランとの間の脱水素カップリング反応の触媒作用 |
| TWI784022B (zh) * | 2017-07-31 | 2022-11-21 | 中國大陸商南大光電半導體材料有限公司 | 1,1,1-參(二甲胺基)二矽烷及其製備方法 |
| EP3682041B1 (en) * | 2017-09-14 | 2022-04-20 | Versum Materials US, LLC | Methods for depositing silicon-containing films |
| JP6788650B2 (ja) * | 2017-12-08 | 2020-11-25 | ダウ シリコーンズ コーポレーション | ヒドロカルビルオキシジシラン |
| CN108084219B (zh) * | 2017-12-26 | 2020-09-15 | 浙江博瑞电子科技有限公司 | 一种二（二乙基氨基）硅烷合成方法 |
| US11702432B2 (en) * | 2018-05-23 | 2023-07-18 | Dow Silicones Corporation | Method of making an organoaminosilane |
| JP7553454B2 (ja) * | 2019-02-05 | 2024-09-18 | バーサム マテリアルズ ユーエス，リミティド ライアビリティ カンパニー | 炭素ドープされた酸化ケイ素の堆積 |
| US11649560B2 (en) | 2019-06-20 | 2023-05-16 | Applied Materials, Inc. | Method for forming silicon-phosphorous materials |
| US11466037B2 (en) * | 2019-10-31 | 2022-10-11 | Nata Semiconductor Materials Co., Ltd. | Catalysis of dehydrocoupling reactions between amines and silanes |
| EP4110968A4 (en) * | 2020-04-02 | 2023-09-13 | Versum Materials US, LLC | ORGANOAMINO-FUNCTIONAL CYCLIC OLIGOSILOXANES FOR DEPOSITION OF SILICON-CONTAINING FILMS |
| TWI797640B (zh) | 2020-06-18 | 2023-04-01 | 法商液態空氣喬治斯克勞帝方法研究開發股份有限公司 | 基於矽之自組裝單層組成物及使用該組成物之表面製備 |
| CN112210769B (zh) * | 2020-09-29 | 2023-04-25 | 合肥安德科铭半导体科技有限公司 | 一种低温高生长速率氧化硅薄膜的原子层沉积方法 |
| CN115260223B (zh) * | 2022-09-26 | 2022-12-23 | 江苏南大光电材料股份有限公司 | 无氯催化剂于制备二异丙胺硅烷中的用途 |
| KR102858392B1 (ko) | 2023-07-18 | 2025-09-11 | 주식회사 한솔케미칼 | 2종의 실리콘 전구체 화합물을 이용하여 박막을 형성하는 방법 |
| KR20250085041A (ko) | 2023-12-04 | 2025-06-12 | (주)원익머트리얼즈 | 디알킬아미노디실란의 제조방법 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5736424Y2 (cg-RX-API-DMAC7.html) | 1973-01-17 | 1982-08-11 | ||
| JPS49110673A (cg-RX-API-DMAC7.html) | 1973-03-07 | 1974-10-22 | ||
| JPS519738B2 (cg-RX-API-DMAC7.html) * | 1973-03-07 | 1976-03-30 | ||
| US4965367A (en) * | 1989-10-16 | 1990-10-23 | Dow Corning Corporation | Process for preparation of silacyclobutanes |
| FR2739283B1 (fr) | 1995-09-29 | 1997-11-07 | Oreal | Composition topique contenant un polymere a greffons silicones et un polymere amphiphile a chaine grasse |
| US6072085A (en) | 1997-09-30 | 2000-06-06 | Massachusetts Institute Of Technology | Imine hydrosilylation, uses and reagents related thereto |
| FR2833944A1 (fr) * | 2001-12-20 | 2003-06-27 | Rhodia Chimie Sa | Procede de preparation d'amines par reduction d'imines |
| AU2003286709B8 (en) | 2002-10-28 | 2009-11-19 | Insight Equity A.P.X., Lp | Oxygen-containing heterocyclic fused naphthopyrans |
| US7875556B2 (en) | 2005-05-16 | 2011-01-25 | Air Products And Chemicals, Inc. | Precursors for CVD silicon carbo-nitride and silicon nitride films |
| US8530361B2 (en) | 2006-05-23 | 2013-09-10 | Air Products And Chemicals, Inc. | Process for producing silicon and oxide films from organoaminosilane precursors |
| KR101040325B1 (ko) | 2009-08-25 | 2011-06-10 | (주)디엔에프 | 알킬아미노실란의 제조방법 |
| US20120277457A1 (en) | 2010-10-12 | 2012-11-01 | Air Products And Chemicals, Inc. | Aminosilanes and methods for making same |
| US10453675B2 (en) * | 2013-09-20 | 2019-10-22 | Versum Materials Us, Llc | Organoaminosilane precursors and methods for depositing films comprising same |
| US9233990B2 (en) * | 2014-02-28 | 2016-01-12 | Air Products And Chemicals, Inc. | Organoaminosilanes and methods for making same |
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| KR20180079259A (ko) | 2018-07-10 |
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| US20160168169A1 (en) | 2016-06-16 |
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