JP2013221001A - 環状シラザン化合物の製造方法 - Google Patents
環状シラザン化合物の製造方法 Download PDFInfo
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- JP2013221001A JP2013221001A JP2012092646A JP2012092646A JP2013221001A JP 2013221001 A JP2013221001 A JP 2013221001A JP 2012092646 A JP2012092646 A JP 2012092646A JP 2012092646 A JP2012092646 A JP 2012092646A JP 2013221001 A JP2013221001 A JP 2013221001A
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- JP
- Japan
- Prior art keywords
- disila
- cyclic silazane
- tetramethyl
- silazane compound
- formula
- 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
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 58
- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 46
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 17
- -1 sulfonic acid compound Chemical class 0.000 claims abstract description 29
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- IPKOJSMGLIKFLO-UHFFFAOYSA-N 2,2,5,5-tetramethyl-1,2,5-azadisilolidine Chemical compound C[Si]1(C)CC[Si](C)(C)N1 IPKOJSMGLIKFLO-UHFFFAOYSA-N 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 239000000654 additive Substances 0.000 abstract description 6
- 239000000853 adhesive Substances 0.000 abstract description 6
- 239000000835 fiber Substances 0.000 abstract description 6
- 239000003973 paint Substances 0.000 abstract description 6
- 230000000996 additive effect Effects 0.000 abstract description 5
- 230000001070 adhesive effect Effects 0.000 abstract description 5
- 239000012756 surface treatment agent Substances 0.000 abstract description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 19
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000005336 cracking Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229940098779 methanesulfonic acid Drugs 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VVNWHIYYCOBFMW-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1,2,6-azadisilinane Chemical compound C[Si]1(C)CCC[Si](C)(C)N1 VVNWHIYYCOBFMW-UHFFFAOYSA-N 0.000 description 2
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- VGQOKOYKFDUPPJ-UHFFFAOYSA-N chloro-[2-[chloro(dimethyl)silyl]ethyl]-dimethylsilane Chemical compound C[Si](C)(Cl)CC[Si](C)(C)Cl VGQOKOYKFDUPPJ-UHFFFAOYSA-N 0.000 description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 description 2
- 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 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- GKNWQHIXXANPTN-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)F GKNWQHIXXANPTN-UHFFFAOYSA-N 0.000 description 1
- KZWJWYFPLXRYIL-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)F KZWJWYFPLXRYIL-UHFFFAOYSA-N 0.000 description 1
- MDNDVKWCOGNEPB-UHFFFAOYSA-N 1,1,3,3-tetramethyl-2-phenyl-2,1,3-benzazadisilole Chemical compound C[Si]1(C)N(c2ccccc2)[Si](C)(C)c2ccccc12 MDNDVKWCOGNEPB-UHFFFAOYSA-N 0.000 description 1
- VPLHRZBRWMWQSX-UHFFFAOYSA-N 1,1,3,3-tetramethyl-2h-2,1,3-benzazadisilole Chemical compound C1=CC=C2[Si](C)(C)N[Si](C)(C)C2=C1 VPLHRZBRWMWQSX-UHFFFAOYSA-N 0.000 description 1
- BFFTXLUOWNVAKC-UHFFFAOYSA-N 1,2,2,3-tetramethyl-1,2,5-azadisilolidine Chemical compound CC1C[SiH2]N(C)[Si]1(C)C BFFTXLUOWNVAKC-UHFFFAOYSA-N 0.000 description 1
- FANRZBLWPQTCDE-UHFFFAOYSA-N 1,2,2,5,5-pentamethyl-1,2,5-azadisilolidine Chemical compound CN1[Si](C)(C)CC[Si]1(C)C FANRZBLWPQTCDE-UHFFFAOYSA-N 0.000 description 1
- XSFQDEKDQXXGQN-UHFFFAOYSA-N 1,2,2,6,6-pentamethyl-1,2,6-azadisilinane Chemical compound CN1[Si](C)(C)CCC[Si]1(C)C XSFQDEKDQXXGQN-UHFFFAOYSA-N 0.000 description 1
- HKQFREMPUZUZNA-UHFFFAOYSA-N 1,2,6-azadisilinane Chemical compound C1C[SiH2]N[SiH2]C1 HKQFREMPUZUZNA-UHFFFAOYSA-N 0.000 description 1
- ZWHJOKVPBMQCSF-UHFFFAOYSA-N 1-benzyl-2,2,5,5-tetramethyl-1,2,5-azadisilolidine Chemical compound C[Si]1(C)CC[Si](C)(C)N1CC1=CC=CC=C1 ZWHJOKVPBMQCSF-UHFFFAOYSA-N 0.000 description 1
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- GLEQQMWBRSFMLV-UHFFFAOYSA-N 1-cyclohexyl-2,2,5,5-tetramethyl-1,2,5-azadisilolidine Chemical compound C[Si]1(CC[Si](N1C2CCCCC2)(C)C)C GLEQQMWBRSFMLV-UHFFFAOYSA-N 0.000 description 1
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- QPLTZDQZGYKJSG-UHFFFAOYSA-N 1-methyl-1,2,5-azadisilolidine Chemical compound CN1[SiH2]CC[SiH2]1 QPLTZDQZGYKJSG-UHFFFAOYSA-N 0.000 description 1
- NRVSPQUHAYMAHM-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1-propyl-1,2,4-azadisiletidine Chemical compound CCCN1[Si](C)(C)C[Si]1(C)C NRVSPQUHAYMAHM-UHFFFAOYSA-N 0.000 description 1
- FYXCYHQXUWUWFN-UHFFFAOYSA-N 2,2,5,5,7,7,10,10-octamethyl-1,6,2,5,7,10-diazatetrasilecane Chemical compound C[Si]1(C)CC[Si](C)(C)N[Si](C)(C)CC[Si](C)(C)N1 FYXCYHQXUWUWFN-UHFFFAOYSA-N 0.000 description 1
- RCCDTZSYYZCSDT-UHFFFAOYSA-N 2,2,5,5-tetraethyl-1,2,5-azadisilolidine Chemical compound CC[Si]1(CC)CC[Si](CC)(CC)N1 RCCDTZSYYZCSDT-UHFFFAOYSA-N 0.000 description 1
- CNBFINHDTHWNJY-UHFFFAOYSA-N 2,2,5,5-tetramethyl-1-phenyl-1,2,5-azadisilolidine Chemical compound C[Si]1(C)CC[Si](C)(C)N1C1=CC=CC=C1 CNBFINHDTHWNJY-UHFFFAOYSA-N 0.000 description 1
- UHPDDKDFATYPJX-UHFFFAOYSA-N 2,2,5,5-tetramethyl-1-propyl-1,2,5-azadisilolidine Chemical compound CCCN1[Si](C)(C)CC[Si]1(C)C UHPDDKDFATYPJX-UHFFFAOYSA-N 0.000 description 1
- NGBGZUMHRZQTCJ-UHFFFAOYSA-N 2,2,6,6-tetraethyl-1,2,6-azadisilinane Chemical compound CC[Si]1(CC)CCC[Si](CC)(CC)N1 NGBGZUMHRZQTCJ-UHFFFAOYSA-N 0.000 description 1
- HKEZIKHMMUJDIJ-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-propyl-1,2,6-azadisilinane Chemical compound CCCN1[Si](C)(C)CCC[Si]1(C)C HKEZIKHMMUJDIJ-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-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
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- LFASKLONFHYHQA-UHFFFAOYSA-N CC[Si]1(CCC[Si](N1C2CCCCC2)(CC)CC)CC Chemical compound CC[Si]1(CCC[Si](N1C2CCCCC2)(CC)CC)CC LFASKLONFHYHQA-UHFFFAOYSA-N 0.000 description 1
- YYDSIRIGWAKVMK-UHFFFAOYSA-N CC[Si]1(CC[Si](N1C)(CC)CC)CC Chemical compound CC[Si]1(CC[Si](N1C)(CC)CC)CC YYDSIRIGWAKVMK-UHFFFAOYSA-N 0.000 description 1
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- YJBAFLFVUORIAC-UHFFFAOYSA-N CN1[Si](C2=CC=CC=C2[Si]1(C)C)(C)C Chemical compound CN1[Si](C2=CC=CC=C2[Si]1(C)C)(C)C YJBAFLFVUORIAC-UHFFFAOYSA-N 0.000 description 1
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
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- BSKSKJHGLWDKSC-UHFFFAOYSA-N I[Si](CC[Si](C)(C)I)(C)C Chemical compound I[Si](CC[Si](C)(C)I)(C)C BSKSKJHGLWDKSC-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-butylamine Natural products CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
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- 125000002252 acyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001204 arachidyl 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])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])[H] 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- GYEOTFVABVWJFG-UHFFFAOYSA-N bromo-[2-[bromo(diethyl)silyl]ethyl]-diethylsilane Chemical compound CC[Si](Br)(CC)CC[Si](Br)(CC)CC GYEOTFVABVWJFG-UHFFFAOYSA-N 0.000 description 1
- VKSREWXQBUQJCH-UHFFFAOYSA-N bromo-[2-[bromo(dimethyl)silyl]ethyl]-dimethylsilane Chemical compound C[Si](C)(Br)CC[Si](C)(C)Br VKSREWXQBUQJCH-UHFFFAOYSA-N 0.000 description 1
- ORLVVGRGNOFIBI-UHFFFAOYSA-N bromo-[2-[bromo(dimethyl)silyl]phenyl]-dimethylsilane Chemical compound C[Si](C)(Br)C1=CC=CC=C1[Si](C)(C)Br ORLVVGRGNOFIBI-UHFFFAOYSA-N 0.000 description 1
- CXRQDGATOVWLNB-UHFFFAOYSA-N bromo-[3-[bromo(diethyl)silyl]propyl]-diethylsilane Chemical compound CC[Si](Br)(CC)CCC[Si](Br)(CC)CC CXRQDGATOVWLNB-UHFFFAOYSA-N 0.000 description 1
- VBICSIJMCGIIGI-UHFFFAOYSA-N bromo-[4-[bromo(diethyl)silyl]phenyl]-diethylsilane Chemical compound CC[Si](Br)(CC)C1=CC=C([Si](Br)(CC)CC)C=C1 VBICSIJMCGIIGI-UHFFFAOYSA-N 0.000 description 1
- TUQOJLURZOLENN-UHFFFAOYSA-N bromo-[4-[bromo(dimethyl)silyl]phenyl]-dimethylsilane Chemical compound C[Si](C)(Br)C1=CC=C([Si](C)(C)Br)C=C1 TUQOJLURZOLENN-UHFFFAOYSA-N 0.000 description 1
- FMPDHFFHCUBCCM-UHFFFAOYSA-N bromo-[[bromo(diethyl)silyl]methyl]-diethylsilane Chemical compound CC[Si](Br)(CC)C[Si](Br)(CC)CC FMPDHFFHCUBCCM-UHFFFAOYSA-N 0.000 description 1
- WFSKWWDLRAWYDN-UHFFFAOYSA-N bromo-[[bromo(dimethyl)silyl]methyl]-dimethylsilane Chemical compound C[Si](C)(Br)C[Si](C)(C)Br WFSKWWDLRAWYDN-UHFFFAOYSA-N 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- DQQDXIZNXVNECP-UHFFFAOYSA-N chloro-[2-[chloro(diethyl)silyl]ethyl]-diethylsilane Chemical compound CC[Si](Cl)(CC)CC[Si](Cl)(CC)CC DQQDXIZNXVNECP-UHFFFAOYSA-N 0.000 description 1
- JYRGBPNCTYXWKG-UHFFFAOYSA-N chloro-[2-[chloro(diethyl)silyl]phenyl]-diethylsilane Chemical compound CC[Si](Cl)(CC)C1=CC=CC=C1[Si](Cl)(CC)CC JYRGBPNCTYXWKG-UHFFFAOYSA-N 0.000 description 1
- XQTKCMUQJKYHFM-UHFFFAOYSA-N chloro-[2-[chloro(dimethyl)silyl]phenyl]-dimethylsilane Chemical compound C[Si](C)(Cl)C1=CC=CC=C1[Si](C)(C)Cl XQTKCMUQJKYHFM-UHFFFAOYSA-N 0.000 description 1
- RTZLYROJRXLBPM-UHFFFAOYSA-N chloro-[3-[chloro(diethyl)silyl]propyl]-diethylsilane Chemical compound CC[Si](Cl)(CC)CCC[Si](Cl)(CC)CC RTZLYROJRXLBPM-UHFFFAOYSA-N 0.000 description 1
- XJYPEWPGZBASNR-UHFFFAOYSA-N chloro-[3-[chloro(dimethyl)silyl]propyl]-dimethylsilane Chemical compound C[Si](C)(Cl)CCC[Si](C)(C)Cl XJYPEWPGZBASNR-UHFFFAOYSA-N 0.000 description 1
- COFLYCFUVHLITN-UHFFFAOYSA-N chloro-[4-[chloro(dimethyl)silyl]phenyl]-dimethylsilane Chemical compound C[Si](C)(Cl)C1=CC=C([Si](C)(C)Cl)C=C1 COFLYCFUVHLITN-UHFFFAOYSA-N 0.000 description 1
- SPWZWKJYOOVSHH-UHFFFAOYSA-N chloro-[[chloro(diethyl)silyl]methyl]-diethylsilane Chemical compound CC[Si](Cl)(CC)C[Si](Cl)(CC)CC SPWZWKJYOOVSHH-UHFFFAOYSA-N 0.000 description 1
- VTDZAHJRMRMQNP-UHFFFAOYSA-N chloro-[[chloro(dimethyl)silyl]methyl]-dimethylsilane Chemical compound C[Si](C)(Cl)C[Si](C)(C)Cl VTDZAHJRMRMQNP-UHFFFAOYSA-N 0.000 description 1
- KWYZNESIGBQHJK-UHFFFAOYSA-N chloro-dimethyl-phenylsilane Chemical compound C[Si](C)(Cl)C1=CC=CC=C1 KWYZNESIGBQHJK-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 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 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
- 125000004185 ester group Chemical group 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 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
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([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
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-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
- 125000000913 palmityl 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])C([H])([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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940117803 phenethylamine Drugs 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
[1] 下記一般式(1)
で示される鎖状又は環状シラザン化合物を含有する混合物を、スルホン酸化合物又はその塩の存在下で加熱することを特徴とする下記一般式(2)
で示される環状シラザン化合物の製造方法。
[2] 上記一般式(1)で示される鎖状又は環状シラザン化合物を含有する混合物が、下記一般式(3)
で示されるビスハロシラン化合物と、下記一般式(4)
R6NH2 (4)
(式中、R6は水素原子又は炭素数1〜20の非置換もしくは置換の1価炭化水素基である。)
で示される含窒素化合物とを反応させて製造されたものである[1]記載の環状シラザン化合物の製造方法。
[3] 上記一般式(2)で示される環状シラザン化合物が、2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンである[1]又は[2]記載の環状シラザン化合物の製造方法。
で示される鎖状又は環状シラザン化合物を含有する混合物を、スルホン酸化合物又はその塩の存在下で加熱することにより、下記式(2)の環状シラザン化合物を得ることを特徴とするものである。
nは2以上の整数であり、具体的には2〜30、好ましくは2〜20である。
留去時の圧力は特に限定されないが、0.1〜200kPa、特に0.2〜102kPaが好ましい。
で示されるビスハロシラン化合物と下記一般式(4)
R6NH2 (4)
(式中、R6は水素原子又は炭素数1〜20の非置換もしくは置換の1価炭化水素基である。)
で示される含窒素化合物を反応させて製造する方法が挙げられる。
で示される化合物である。
ここで、R1、R2、R3、R4、R5は上述したものが例示される。
R6NH2 (4)
(式中、R6は水素原子又は炭素数1〜20の非置換もしくは置換の1価炭化水素基である。)
で示される化合物である。
R6は、上述したものが例示される。
撹拌機、還流器、ガス吹込管及び温度計を備えたフラスコに、1,2−ビス(クロロジメチルシリル)エタン107.7g(0.5モル)、テトラリン300mlを仕込み、25〜40℃でアンモニア25.5g(1.5モル)を3時間かけて吹き込み、その温度で1時間撹拌した。生成した塩化アンモニウムをろ過により除去し、2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンを含有する混合物を364g得た。混合物をガスクロマトグラフィーで分析したところ、混合物中の2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンの含有量は31.9gであった(ガスクロマトグラフィーによる内部標準収率40%)。
合成例1で得られた2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンを含む混合物を還流器、蒸留塔、留出管を備えたフラスコに仕込み、メタンスルホン酸0.5g(0.005モル)を添加し、5kPaに減圧した。フラスコを加熱し、2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンを塔頂温度52〜53℃、釜温96〜108℃の留分として65.6g得た。この留分をガスクロマトグラフィーで分析したところ、2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンの純度は98%であった。収率は81%であり、クラッキングにより2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンが生成していることが確認された。
メタンスルホン酸の代わりにトリフルオロメタンスルホン酸0.75g(0.005モル)を添加した以外は、実施例1と同様に実験を行った。2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンを塔頂温度52〜53℃、釜温94〜108℃の留分として49.9g得た。この留分をガスクロマトグラフィーで分析したところ、2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンの純度は98%であった。収率は61%であり、クラッキングにより2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンが生成していることが確認された。
メタンスルホン酸の代わりにドデシルベンゼンスルホン酸1.6g(0.005モル)を添加した以外は、実施例1と同様に実験を行った。2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンを塔頂温度52〜53℃、釜温95〜108℃の留分として60.6g得た。この留分をガスクロマトグラフィーで分析したところ、2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンの純度は98%であった。収率は75%であり、クラッキングにより2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンが生成していることが確認された。
メタンスルホン酸を添加しなかった以外は、実施例1と同様に実験を行った。2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンを塔頂温度52〜53℃、釜温100〜108℃の留分として27.1g得た。この留分をガスクロマトグラフィーで分析したところ、2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンの純度は97%であった。収率は33%であり、クラッキングにより2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンは生成していないことが確認された。
メタンスルホン酸の代わりに28質量%ナトリウムメトキシドのメタノール溶液1.0g(0.005モル)を添加した以外は実施例1と同様に実験を行った。2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンを塔頂温度52〜53℃、釜温99〜108℃の留分として27.9g得た。この留分をガスクロマトグラフィーで分析したところ、2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンの純度は97%であった。収率は34%であり、クラッキングにより2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンは生成していないことが確認された。
Claims (3)
- 上記一般式(2)で示される環状シラザン化合物が、2,2,5,5−テトラメチル−2,5−ジシラ−1−アザシクロペンタンである請求項1又は2記載の環状シラザン化合物の製造方法。
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