CA1124740A - Catalyzed redistribution of alkyltin halides - Google Patents
Catalyzed redistribution of alkyltin halidesInfo
- Publication number
- CA1124740A CA1124740A CA211,734A CA211734A CA1124740A CA 1124740 A CA1124740 A CA 1124740A CA 211734 A CA211734 A CA 211734A CA 1124740 A CA1124740 A CA 1124740A
- Authority
- CA
- Canada
- Prior art keywords
- process according
- alkyl
- tin
- chloride
- iodide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000004820 halides Chemical class 0.000 title abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical compound C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 4
- YFRLQYJXUZRYDN-UHFFFAOYSA-K trichloro(methyl)stannane Chemical compound C[Sn](Cl)(Cl)Cl YFRLQYJXUZRYDN-UHFFFAOYSA-K 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 229910052785 arsenic Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 150000003606 tin compounds Chemical class 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- -1 alkyl tin halides Chemical class 0.000 abstract description 8
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract description 6
- 238000007323 disproportionation reaction Methods 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 4
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- 230000000875 corresponding effect Effects 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- VTHGHWCUKLJZBL-UHFFFAOYSA-N (4-methylphenyl)tin Chemical compound CC1=CC=C([Sn])C=C1 VTHGHWCUKLJZBL-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229910008046 SnC14 Inorganic materials 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- ZWPQDDCPESTSTK-UHFFFAOYSA-K 2-ethylhexyl(triiodo)stannane Chemical compound CCCCC(CC)C[Sn](I)(I)I ZWPQDDCPESTSTK-UHFFFAOYSA-K 0.000 description 2
- 229910008066 SnC12 Inorganic materials 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 229940107816 ammonium iodide Drugs 0.000 description 2
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical class [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 description 2
- 229940040544 bromides Drugs 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- GTVGGZBELVUNIL-UHFFFAOYSA-K butyltin(3+);triiodide Chemical compound CCCC[Sn](I)(I)I GTVGGZBELVUNIL-UHFFFAOYSA-K 0.000 description 2
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- VDEKURXOWJYWCG-UHFFFAOYSA-N dodecyltin Chemical compound CCCCCCCCCCCC[Sn] VDEKURXOWJYWCG-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 150000004010 onium ions Chemical class 0.000 description 2
- LSMAIBOZUPTNBR-UHFFFAOYSA-N phosphanium;iodide Chemical class [PH4+].[I-] LSMAIBOZUPTNBR-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- SBCUXVQZGCKZET-UHFFFAOYSA-N tetrabenzylphosphanium Chemical compound C=1C=CC=CC=1C[P+](CC=1C=CC=CC=1)(CC=1C=CC=CC=1)CC1=CC=CC=C1 SBCUXVQZGCKZET-UHFFFAOYSA-N 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- NZTXPNNZHAACBT-UHFFFAOYSA-N tetramethylarsanium Chemical compound C[As+](C)(C)C NZTXPNNZHAACBT-UHFFFAOYSA-N 0.000 description 2
- TVVPMLFGPYQGTG-UHFFFAOYSA-M tetramethylphosphanium;iodide Chemical compound [I-].C[P+](C)(C)C TVVPMLFGPYQGTG-UHFFFAOYSA-M 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- QPBYLOWPSRZOFX-UHFFFAOYSA-J tin(iv) iodide Chemical compound I[Sn](I)(I)I QPBYLOWPSRZOFX-UHFFFAOYSA-J 0.000 description 2
- VEKOBSVHVWMWRA-UHFFFAOYSA-K tribromo(2-ethylhexyl)stannane Chemical compound CCCCC(CC)C[Sn](Br)(Br)Br VEKOBSVHVWMWRA-UHFFFAOYSA-K 0.000 description 2
- DJLHUBJAECUMLX-UHFFFAOYSA-K tribromo(6-methylheptyl)stannane Chemical compound CC(C)CCCCC[Sn](Br)(Br)Br DJLHUBJAECUMLX-UHFFFAOYSA-K 0.000 description 2
- BMRKNRNFWARTTN-UHFFFAOYSA-K tribromo(octyl)stannane Chemical compound CCCCCCCC[Sn](Br)(Br)Br BMRKNRNFWARTTN-UHFFFAOYSA-K 0.000 description 2
- OWWHESVNCQAYQR-UHFFFAOYSA-K trichloro(2-ethylhexyl)stannane Chemical compound CCCCC(CC)C[Sn](Cl)(Cl)Cl OWWHESVNCQAYQR-UHFFFAOYSA-K 0.000 description 2
- LRKFZOQBINVWHG-UHFFFAOYSA-K trichloro(6-methylheptyl)stannane Chemical compound CC(C)CCCCC[Sn](Cl)(Cl)Cl LRKFZOQBINVWHG-UHFFFAOYSA-K 0.000 description 2
- YAKWASWAUWOPAQ-UHFFFAOYSA-K triiodo(6-methylheptyl)stannane Chemical compound CC(C)CCCCC[Sn](I)(I)I YAKWASWAUWOPAQ-UHFFFAOYSA-K 0.000 description 2
- RXWKFHGICDWKDN-UHFFFAOYSA-K triiodo(octyl)stannane Chemical compound CCCCCCCC[Sn](I)(I)I RXWKFHGICDWKDN-UHFFFAOYSA-K 0.000 description 2
- HHIQCKSDOMLQMO-UHFFFAOYSA-K triiodo(propyl)stannane Chemical compound CCC[Sn](I)(I)I HHIQCKSDOMLQMO-UHFFFAOYSA-K 0.000 description 2
- KUCWUAFNGCMZDB-UHFFFAOYSA-N 2-amino-3-nitrophenol Chemical compound NC1=C(O)C=CC=C1[N+]([O-])=O KUCWUAFNGCMZDB-UHFFFAOYSA-N 0.000 description 1
- ADIGPKFQNVDTHO-UHFFFAOYSA-N 4-methylaniline;hydroiodide Chemical compound [I-].CC1=CC=C([NH3+])C=C1 ADIGPKFQNVDTHO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FWGUGVZBOVCIPE-UHFFFAOYSA-N CC(C)CCCCC[Sn] Chemical compound CC(C)CCCCC[Sn] FWGUGVZBOVCIPE-UHFFFAOYSA-N 0.000 description 1
- VLTIIWDDWCBHEO-UHFFFAOYSA-N CCCCC(CC)C[Sn] Chemical compound CCCCC(CC)C[Sn] VLTIIWDDWCBHEO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 1
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- SHWIIIVDPZCDHE-UHFFFAOYSA-K benzyl(triiodo)stannane Chemical compound I[Sn](I)(I)CC1=CC=CC=C1 SHWIIIVDPZCDHE-UHFFFAOYSA-K 0.000 description 1
- MUIUMBKGZPBYCW-UHFFFAOYSA-K benzyltin(3+);tribromide Chemical compound Br[Sn](Br)(Br)CC1=CC=CC=C1 MUIUMBKGZPBYCW-UHFFFAOYSA-K 0.000 description 1
- ZPLRQSPYSZDKCM-UHFFFAOYSA-K benzyltin(3+);trichloride Chemical compound Cl[Sn](Cl)(Cl)CC1=CC=CC=C1 ZPLRQSPYSZDKCM-UHFFFAOYSA-K 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- PCZGZQPGIPQNDK-UHFFFAOYSA-N bromo(tetramethyl)-lambda5-arsane Chemical compound C[As](C)(C)(C)Br PCZGZQPGIPQNDK-UHFFFAOYSA-N 0.000 description 1
- FAMUPMBATZGWOV-UHFFFAOYSA-M bromo(triphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Br)C1=CC=CC=C1 FAMUPMBATZGWOV-UHFFFAOYSA-M 0.000 description 1
- XEPOQNSTZCBBQN-UHFFFAOYSA-N bromoarsenic Chemical compound [As]Br XEPOQNSTZCBBQN-UHFFFAOYSA-N 0.000 description 1
- LUZSPGQEISANPO-UHFFFAOYSA-N butyltin Chemical compound CCCC[Sn] LUZSPGQEISANPO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- PIMYDFDXAUVLON-UHFFFAOYSA-M chloro(triethyl)stannane Chemical compound CC[Sn](Cl)(CC)CC PIMYDFDXAUVLON-UHFFFAOYSA-M 0.000 description 1
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 1
- MCNGJXAXOJDJKO-UHFFFAOYSA-M chloro(trioctyl)stannane Chemical compound CCCCCCCC[Sn](Cl)(CCCCCCCC)CCCCCCCC MCNGJXAXOJDJKO-UHFFFAOYSA-M 0.000 description 1
- HDINKIBQOCEUKW-UHFFFAOYSA-N chloroarsenic Chemical compound [As]Cl HDINKIBQOCEUKW-UHFFFAOYSA-N 0.000 description 1
- BESRBWLUVPELTD-UHFFFAOYSA-K cyclohexyltin(3+);trichloride Chemical compound Cl[Sn](Cl)(Cl)C1CCCCC1 BESRBWLUVPELTD-UHFFFAOYSA-K 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- OUQICVAWQYLFTL-UHFFFAOYSA-L di(butan-2-yl)tin(2+);dichloride Chemical compound CCC(C)[Sn](Cl)(Cl)C(C)CC OUQICVAWQYLFTL-UHFFFAOYSA-L 0.000 description 1
- PLOWAKQTEHQOFB-UHFFFAOYSA-L di(propan-2-yl)tin(2+);dichloride Chemical compound CC(C)[Sn](Cl)(Cl)C(C)C PLOWAKQTEHQOFB-UHFFFAOYSA-L 0.000 description 1
- VKHDSOXSTURPAJ-UHFFFAOYSA-L dibenzyl(dibromo)stannane Chemical compound C=1C=CC=CC=1C[Sn](Br)(Br)CC1=CC=CC=C1 VKHDSOXSTURPAJ-UHFFFAOYSA-L 0.000 description 1
- ZGXKKMOMGSNTMD-UHFFFAOYSA-L dibenzyl(diiodo)stannane Chemical compound C=1C=CC=CC=1C[Sn](I)(I)CC1=CC=CC=C1 ZGXKKMOMGSNTMD-UHFFFAOYSA-L 0.000 description 1
- MKANCOHERYHKAT-UHFFFAOYSA-L dibenzyltin(2+);dichloride Chemical compound C=1C=CC=CC=1C[Sn](Cl)(Cl)CC1=CC=CC=C1 MKANCOHERYHKAT-UHFFFAOYSA-L 0.000 description 1
- QSGGLKRQVLBHKX-UHFFFAOYSA-L dibromo(diethyl)stannane Chemical compound CC[Sn](Br)(Br)CC QSGGLKRQVLBHKX-UHFFFAOYSA-L 0.000 description 1
- GNMVEKSYLLXJKX-UHFFFAOYSA-L dibromo(dioctyl)stannane Chemical compound CCCCCCCC[Sn](Br)(Br)CCCCCCCC GNMVEKSYLLXJKX-UHFFFAOYSA-L 0.000 description 1
- QAHAIHQMIYXJNS-UHFFFAOYSA-L dibromo-di(butan-2-yl)stannane Chemical compound CCC(C)[Sn](Br)(Br)C(C)CC QAHAIHQMIYXJNS-UHFFFAOYSA-L 0.000 description 1
- QSHZUFRQHSINTB-UHFFFAOYSA-L dibutyltin(2+);dibromide Chemical compound CCCC[Sn](Br)(Br)CCCC QSHZUFRQHSINTB-UHFFFAOYSA-L 0.000 description 1
- HLATYLIVBMECMN-UHFFFAOYSA-L dibutyltin(2+);diiodide Chemical compound CCCC[Sn](I)(I)CCCC HLATYLIVBMECMN-UHFFFAOYSA-L 0.000 description 1
- YFAXVVMIXZAKSR-UHFFFAOYSA-L dichloro(diethyl)stannane Chemical compound CC[Sn](Cl)(Cl)CC YFAXVVMIXZAKSR-UHFFFAOYSA-L 0.000 description 1
- DGUPLUPXYGDCQP-UHFFFAOYSA-L dichloro(dipentyl)stannane Chemical compound CCCCC[Sn](Cl)(Cl)CCCCC DGUPLUPXYGDCQP-UHFFFAOYSA-L 0.000 description 1
- ISXUHJXWYNONDI-UHFFFAOYSA-L dichloro(diphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](Cl)(Cl)C1=CC=CC=C1 ISXUHJXWYNONDI-UHFFFAOYSA-L 0.000 description 1
- GXWLHTAAGCHDAV-UHFFFAOYSA-L dichloro-bis(2-methylpropyl)stannane Chemical compound CC(C)C[Sn](Cl)(Cl)CC(C)C GXWLHTAAGCHDAV-UHFFFAOYSA-L 0.000 description 1
- RHFTTZVNBAHQBF-UHFFFAOYSA-L dicyclohexyltin(2+);dibromide Chemical compound C1CCCCC1[Sn](Br)(Br)C1CCCCC1 RHFTTZVNBAHQBF-UHFFFAOYSA-L 0.000 description 1
- NXLNBJXGFFFGIT-UHFFFAOYSA-L dicyclohexyltin(2+);dichloride Chemical compound C1CCCCC1[Sn](Cl)(Cl)C1CCCCC1 NXLNBJXGFFFGIT-UHFFFAOYSA-L 0.000 description 1
- MATIRGPIRARBGK-UHFFFAOYSA-L diethyl(diiodo)stannane Chemical compound CC[Sn](I)(I)CC MATIRGPIRARBGK-UHFFFAOYSA-L 0.000 description 1
- MLGFKQNIGKTEEV-UHFFFAOYSA-M diethyl(dimethyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(C)CC MLGFKQNIGKTEEV-UHFFFAOYSA-M 0.000 description 1
- AXQSJCWCXATTNE-UHFFFAOYSA-L dihexyltin(2+);dichloride Chemical compound CCCCCC[Sn](Cl)(Cl)CCCCCC AXQSJCWCXATTNE-UHFFFAOYSA-L 0.000 description 1
- UQCWKRIUDXVWRV-UHFFFAOYSA-L diiodo(dioctyl)stannane Chemical compound CCCCCCCC[Sn](I)(I)CCCCCCCC UQCWKRIUDXVWRV-UHFFFAOYSA-L 0.000 description 1
- VPBOTFQLPJZQSU-UHFFFAOYSA-L diiodo(dipropyl)stannane Chemical compound CCC[Sn](I)(I)CCC VPBOTFQLPJZQSU-UHFFFAOYSA-L 0.000 description 1
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 1
- DOHQOGRRQASQAR-UHFFFAOYSA-L dimethyltin(2+);dibromide Chemical compound C[Sn](C)(Br)Br DOHQOGRRQASQAR-UHFFFAOYSA-L 0.000 description 1
- VVYDVQWJZWRVPE-UHFFFAOYSA-L dimethyltin(2+);diiodide Chemical compound C[Sn](C)(I)I VVYDVQWJZWRVPE-UHFFFAOYSA-L 0.000 description 1
- SBOSGIJGEHWBKV-UHFFFAOYSA-L dioctyltin(2+);dichloride Chemical compound CCCCCCCC[Sn](Cl)(Cl)CCCCCCCC SBOSGIJGEHWBKV-UHFFFAOYSA-L 0.000 description 1
- ALOQGPVOAWHHLG-UHFFFAOYSA-L diphenyltin(2+);dibromide Chemical compound C=1C=CC=CC=1[Sn](Br)(Br)C1=CC=CC=C1 ALOQGPVOAWHHLG-UHFFFAOYSA-L 0.000 description 1
- FPXDFNHYWPHJOJ-UHFFFAOYSA-L diphenyltin(2+);diiodide Chemical compound C=1C=CC=CC=1[Sn](I)(I)C1=CC=CC=C1 FPXDFNHYWPHJOJ-UHFFFAOYSA-L 0.000 description 1
- FOPKRSSYSAUFNZ-UHFFFAOYSA-N dipropyltin Chemical compound CCC[Sn]CCC FOPKRSSYSAUFNZ-UHFFFAOYSA-N 0.000 description 1
- CTRHCENQKGMZLE-UHFFFAOYSA-L dipropyltin(2+);dichloride Chemical compound CCC[Sn](Cl)(Cl)CCC CTRHCENQKGMZLE-UHFFFAOYSA-L 0.000 description 1
- JBSAUTFGQMWDTM-UHFFFAOYSA-K dodecyl(triiodo)stannane Chemical compound CCCCCCCCCCCC[Sn](I)(I)I JBSAUTFGQMWDTM-UHFFFAOYSA-K 0.000 description 1
- HJANVHHFNOMJSM-UHFFFAOYSA-M dodecyl(triphenyl)azanium;iodide Chemical compound [I-].C=1C=CC=CC=1[N+](C=1C=CC=CC=1)(CCCCCCCCCCCC)C1=CC=CC=C1 HJANVHHFNOMJSM-UHFFFAOYSA-M 0.000 description 1
- ILXYOJNSZDHABS-UHFFFAOYSA-M dodecyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCCCCCC)C1=CC=CC=C1 ILXYOJNSZDHABS-UHFFFAOYSA-M 0.000 description 1
- XQQOCKKQAMSPIA-UHFFFAOYSA-N ethyl 5-(4-bromophenyl)-1,2-oxazole-3-carboxylate Chemical compound O1N=C(C(=O)OCC)C=C1C1=CC=C(Br)C=C1 XQQOCKKQAMSPIA-UHFFFAOYSA-N 0.000 description 1
- CYRHQOOURDSWBR-UHFFFAOYSA-K ethyl(triiodo)stannane Chemical compound CC[Sn](I)(I)I CYRHQOOURDSWBR-UHFFFAOYSA-K 0.000 description 1
- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- KJSACGHPPNXZFT-UHFFFAOYSA-M iodo(triphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(I)C1=CC=CC=C1 KJSACGHPPNXZFT-UHFFFAOYSA-M 0.000 description 1
- MTAUFTAICGOFHS-UHFFFAOYSA-N iodoarsenic Chemical compound I[As] MTAUFTAICGOFHS-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- YICRPERKKBDRSP-UHFFFAOYSA-N methyl 3-amino-4-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(C)C=1N YICRPERKKBDRSP-UHFFFAOYSA-N 0.000 description 1
- KZKQGUVWZYKJBN-UHFFFAOYSA-N methyl 5-methylsulfonylpyridine-3-carboxylate Chemical compound COC(=O)C1=CN=CC(S(C)(=O)=O)=C1 KZKQGUVWZYKJBN-UHFFFAOYSA-N 0.000 description 1
- OGGXBSGFTTXROS-UHFFFAOYSA-M methyl(triphenyl)azanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[N+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 OGGXBSGFTTXROS-UHFFFAOYSA-M 0.000 description 1
- GGSHUYPVVIISTD-UHFFFAOYSA-M methyl(triphenyl)azanium;iodide Chemical compound [I-].C=1C=CC=CC=1[N+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 GGSHUYPVVIISTD-UHFFFAOYSA-M 0.000 description 1
- JNMIXMFEVJHFNY-UHFFFAOYSA-M methyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 JNMIXMFEVJHFNY-UHFFFAOYSA-M 0.000 description 1
- MSMWWVPVYSKCIM-UHFFFAOYSA-N n-(2-methoxyphenyl)-2,5-dimethylaniline Chemical compound COC1=CC=CC=C1NC1=CC(C)=CC=C1C MSMWWVPVYSKCIM-UHFFFAOYSA-N 0.000 description 1
- CZXLZUSALDPCQX-UHFFFAOYSA-M octyl(triphenyl)azanium;iodide Chemical compound [I-].C=1C=CC=CC=1[N+](C=1C=CC=CC=1)(CCCCCCCC)C1=CC=CC=C1 CZXLZUSALDPCQX-UHFFFAOYSA-M 0.000 description 1
- PJTHHSVHLAQUQM-UHFFFAOYSA-M octyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCC)C1=CC=CC=C1 PJTHHSVHLAQUQM-UHFFFAOYSA-M 0.000 description 1
- VMLNPPLWYBCFAV-UHFFFAOYSA-K phenyltin(3+);tribromide Chemical compound Br[Sn](Br)(Br)C1=CC=CC=C1 VMLNPPLWYBCFAV-UHFFFAOYSA-K 0.000 description 1
- UBOGEXSQACVGEC-UHFFFAOYSA-K phenyltin(3+);trichloride Chemical compound Cl[Sn](Cl)(Cl)C1=CC=CC=C1 UBOGEXSQACVGEC-UHFFFAOYSA-K 0.000 description 1
- KPCRDICFNYEBMJ-UHFFFAOYSA-K phenyltin(3+);triiodide Chemical compound I[Sn](I)(I)C1=CC=CC=C1 KPCRDICFNYEBMJ-UHFFFAOYSA-K 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical class P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- NJASUIDIZMMYED-UHFFFAOYSA-N tetra(propan-2-yl)stannane Chemical compound CC(C)[Sn](C(C)C)(C(C)C)C(C)C NJASUIDIZMMYED-UHFFFAOYSA-N 0.000 description 1
- CCBCJOPAGXYIQL-UHFFFAOYSA-M tetrabenzylazanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C[N+](CC=1C=CC=CC=1)(CC=1C=CC=CC=1)CC1=CC=CC=C1 CCBCJOPAGXYIQL-UHFFFAOYSA-M 0.000 description 1
- LQRZLXMIDINKPN-UHFFFAOYSA-M tetrabenzylazanium;iodide Chemical compound [I-].C=1C=CC=CC=1C[N+](CC=1C=CC=CC=1)(CC=1C=CC=CC=1)CC1=CC=CC=C1 LQRZLXMIDINKPN-UHFFFAOYSA-M 0.000 description 1
- WBVCLUDHJDTUAU-UHFFFAOYSA-N tetrabenzylstannane Chemical compound C=1C=CC=CC=1C[Sn](CC=1C=CC=CC=1)(CC=1C=CC=CC=1)CC1=CC=CC=C1 WBVCLUDHJDTUAU-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- IOCDDXSGYRQOIG-UHFFFAOYSA-N tetrabutylarsanium Chemical compound CCCC[As+](CCCC)(CCCC)CCCC IOCDDXSGYRQOIG-UHFFFAOYSA-N 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- ZXUCBXRTRRIBSO-UHFFFAOYSA-L tetrabutylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC ZXUCBXRTRRIBSO-UHFFFAOYSA-L 0.000 description 1
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 1
- AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
- OBMLOTDECOTAGU-UHFFFAOYSA-M tetradodecylazanium;iodide Chemical compound [I-].CCCCCCCCCCCC[N+](CCCCCCCCCCCC)(CCCCCCCCCCCC)CCCCCCCCCCCC OBMLOTDECOTAGU-UHFFFAOYSA-M 0.000 description 1
- WHMUXLZVFLICJM-UHFFFAOYSA-M tetradodecylphosphanium;iodide Chemical compound [I-].CCCCCCCCCCCC[P+](CCCCCCCCCCCC)(CCCCCCCCCCCC)CCCCCCCCCCCC WHMUXLZVFLICJM-UHFFFAOYSA-M 0.000 description 1
- FDNSKZMGQQDYQB-UHFFFAOYSA-N tetradodecylstannane Chemical compound CCCCCCCCCCCC[Sn](CCCCCCCCCCCC)(CCCCCCCCCCCC)CCCCCCCCCCCC FDNSKZMGQQDYQB-UHFFFAOYSA-N 0.000 description 1
- UQFSVBXCNGCBBW-UHFFFAOYSA-M tetraethylammonium iodide Chemical compound [I-].CC[N+](CC)(CC)CC UQFSVBXCNGCBBW-UHFFFAOYSA-M 0.000 description 1
- WKSYTZHMRBAPAO-UHFFFAOYSA-M tetraethylphosphanium;iodide Chemical compound [I-].CC[P+](CC)(CC)CC WKSYTZHMRBAPAO-UHFFFAOYSA-M 0.000 description 1
- RWWNQEOPUOCKGR-UHFFFAOYSA-N tetraethyltin Chemical compound CC[Sn](CC)(CC)CC RWWNQEOPUOCKGR-UHFFFAOYSA-N 0.000 description 1
- IYTDOHOTDDKRRS-UHFFFAOYSA-N tetrakis(4-methylphenyl)stannane Chemical compound C1=CC(C)=CC=C1[Sn](C=1C=CC(C)=CC=1)(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 IYTDOHOTDDKRRS-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- KEFJVVFCFZNVQM-UHFFFAOYSA-M tetramethylarsanium;iodide Chemical compound [I-].C[As+](C)(C)C KEFJVVFCFZNVQM-UHFFFAOYSA-M 0.000 description 1
- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- IWISVGQUKNSOCC-UHFFFAOYSA-K tetramethylazanium;phosphate Chemical compound C[N+](C)(C)C.C[N+](C)(C)C.C[N+](C)(C)C.[O-]P([O-])([O-])=O IWISVGQUKNSOCC-UHFFFAOYSA-K 0.000 description 1
- ZTXFOCMYRCGSMU-UHFFFAOYSA-M tetramethylphosphanium;bromide Chemical compound [Br-].C[P+](C)(C)C ZTXFOCMYRCGSMU-UHFFFAOYSA-M 0.000 description 1
- NJFUXFRJVIXVSG-UHFFFAOYSA-M tetramethylphosphanium;chloride Chemical compound [Cl-].C[P+](C)(C)C NJFUXFRJVIXVSG-UHFFFAOYSA-M 0.000 description 1
- XQFUVNYJLRTMDN-UHFFFAOYSA-L tetramethylphosphanium;sulfate Chemical compound C[P+](C)(C)C.C[P+](C)(C)C.[O-]S([O-])(=O)=O XQFUVNYJLRTMDN-UHFFFAOYSA-L 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- NWOKSKQOENPYPP-UHFFFAOYSA-M tetraoctadecylazanium;iodide Chemical compound [I-].CCCCCCCCCCCCCCCCCC[N+](CCCCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC NWOKSKQOENPYPP-UHFFFAOYSA-M 0.000 description 1
- QXKLJZBPOOQCOK-UHFFFAOYSA-M tetraoctadecylphosphanium;iodide Chemical compound [I-].CCCCCCCCCCCCCCCCCC[P+](CCCCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC QXKLJZBPOOQCOK-UHFFFAOYSA-M 0.000 description 1
- QBVXKDJEZKEASM-UHFFFAOYSA-M tetraoctylammonium bromide Chemical compound [Br-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC QBVXKDJEZKEASM-UHFFFAOYSA-M 0.000 description 1
- UGQWDFALGKAXTL-UHFFFAOYSA-M tetraoctylazanium;acetate Chemical compound CC([O-])=O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC UGQWDFALGKAXTL-UHFFFAOYSA-M 0.000 description 1
- SNNIPOQLGBPXPS-UHFFFAOYSA-M tetraoctylazanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC SNNIPOQLGBPXPS-UHFFFAOYSA-M 0.000 description 1
- WFIYFFUAOQKJJS-UHFFFAOYSA-N tetraoctylphosphanium Chemical compound CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCCCCCCC WFIYFFUAOQKJJS-UHFFFAOYSA-N 0.000 description 1
- AXTXARBFPWQUQA-UHFFFAOYSA-M tetraoctylphosphanium;chloride Chemical compound [Cl-].CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCCCCCCC AXTXARBFPWQUQA-UHFFFAOYSA-M 0.000 description 1
- JTGNPNLBCGBCMP-UHFFFAOYSA-N tetraoctylstannane Chemical compound CCCCCCCC[Sn](CCCCCCCC)(CCCCCCCC)CCCCCCCC JTGNPNLBCGBCMP-UHFFFAOYSA-N 0.000 description 1
- JEHHMOWXLBXVHN-UHFFFAOYSA-N tetrapentylstannane Chemical compound CCCCC[Sn](CCCCC)(CCCCC)CCCCC JEHHMOWXLBXVHN-UHFFFAOYSA-N 0.000 description 1
- NRZGVGVFPHPXEO-UHFFFAOYSA-M tetraphenylarsanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[As+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NRZGVGVFPHPXEO-UHFFFAOYSA-M 0.000 description 1
- NTIVEBOPRSMRSY-UHFFFAOYSA-M tetraphenylarsanium;iodide Chemical compound [I-].C1=CC=CC=C1[As+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NTIVEBOPRSMRSY-UHFFFAOYSA-M 0.000 description 1
- CZMILNXHOAKSBR-UHFFFAOYSA-N tetraphenylazanium Chemical compound C1=CC=CC=C1[N+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CZMILNXHOAKSBR-UHFFFAOYSA-N 0.000 description 1
- BALCYVFFDOBQPW-UHFFFAOYSA-M tetraphenylazanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[N+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BALCYVFFDOBQPW-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- DMAAYBXYFNPVEY-UHFFFAOYSA-L tetraphenylphosphanium;sulfate Chemical compound [O-]S([O-])(=O)=O.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DMAAYBXYFNPVEY-UHFFFAOYSA-L 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
- CISYLVSCEPBMLO-UHFFFAOYSA-M tetrapropylphosphanium;iodide Chemical compound [I-].CCC[P+](CCC)(CCC)CCC CISYLVSCEPBMLO-UHFFFAOYSA-M 0.000 description 1
- OIQCWAIEHVRCCG-UHFFFAOYSA-N tetrapropylstannane Chemical compound CCC[Sn](CCC)(CCC)CCC OIQCWAIEHVRCCG-UHFFFAOYSA-N 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- WUFKBYTWBJFBOC-UHFFFAOYSA-M tribenzyl(iodo)stannane Chemical compound C=1C=CC=CC=1C[Sn](CC=1C=CC=CC=1)(I)CC1=CC=CC=C1 WUFKBYTWBJFBOC-UHFFFAOYSA-M 0.000 description 1
- JNZRDLWZFWFSBK-UHFFFAOYSA-N tribenzyltin Chemical compound C=1C=CC=CC=1C[Sn](CC=1C=CC=CC=1)CC1=CC=CC=C1 JNZRDLWZFWFSBK-UHFFFAOYSA-N 0.000 description 1
- BYQWEYFCJKJRHO-UHFFFAOYSA-K tribromo(butyl)stannane Chemical compound CCCC[Sn](Br)(Br)Br BYQWEYFCJKJRHO-UHFFFAOYSA-K 0.000 description 1
- NZXDHJANKOMEDR-UHFFFAOYSA-K tribromo(dodecyl)stannane Chemical compound CCCCCCCCCCCC[Sn](Br)(Br)Br NZXDHJANKOMEDR-UHFFFAOYSA-K 0.000 description 1
- GOWIXKGLTIIPQR-UHFFFAOYSA-K tribromo(ethyl)stannane Chemical compound CC[Sn](Br)(Br)Br GOWIXKGLTIIPQR-UHFFFAOYSA-K 0.000 description 1
- SSGLIJVXYPSIEZ-UHFFFAOYSA-K tribromo(methyl)stannane Chemical compound C[Sn](Br)(Br)Br SSGLIJVXYPSIEZ-UHFFFAOYSA-K 0.000 description 1
- BYXWWBJMFOBEHX-UHFFFAOYSA-K tribromo(propyl)stannane Chemical compound CCC[Sn](Br)(Br)Br BYXWWBJMFOBEHX-UHFFFAOYSA-K 0.000 description 1
- YHHVXVNXTMIXOL-UHFFFAOYSA-M tributyl(iodo)stannane Chemical compound CCCC[Sn](I)(CCCC)CCCC YHHVXVNXTMIXOL-UHFFFAOYSA-M 0.000 description 1
- FVRKTAOFDKFAMI-UHFFFAOYSA-M tributylstannanylium;bromide Chemical compound [Br-].CCCC[Sn+](CCCC)CCCC FVRKTAOFDKFAMI-UHFFFAOYSA-M 0.000 description 1
- PDFNMVKYZSDSLJ-UHFFFAOYSA-K trichloro(2-methylpropyl)stannane Chemical compound CC(C)C[Sn](Cl)(Cl)Cl PDFNMVKYZSDSLJ-UHFFFAOYSA-K 0.000 description 1
- MEBRQLCKPRKBOH-UHFFFAOYSA-K trichloro(ethyl)stannane Chemical compound CC[Sn](Cl)(Cl)Cl MEBRQLCKPRKBOH-UHFFFAOYSA-K 0.000 description 1
- COAUSWURBARPGM-UHFFFAOYSA-K trichloro(heptyl)stannane Chemical compound CCCCCCC[Sn](Cl)(Cl)Cl COAUSWURBARPGM-UHFFFAOYSA-K 0.000 description 1
- RIRXGFHMQATDCF-UHFFFAOYSA-K trichloro(hexyl)stannane Chemical compound CCCCCC[Sn](Cl)(Cl)Cl RIRXGFHMQATDCF-UHFFFAOYSA-K 0.000 description 1
- INTLMJZQCBRQAT-UHFFFAOYSA-K trichloro(octyl)stannane Chemical compound CCCCCCCC[Sn](Cl)(Cl)Cl INTLMJZQCBRQAT-UHFFFAOYSA-K 0.000 description 1
- IMNIKXMHMHIKDX-UHFFFAOYSA-K trichloro(propan-2-yl)stannane Chemical compound CC(C)[Sn](Cl)(Cl)Cl IMNIKXMHMHIKDX-UHFFFAOYSA-K 0.000 description 1
- NFJGHYXSHMSYFA-UHFFFAOYSA-K trichloro(propyl)stannane Chemical compound CCC[Sn](Cl)(Cl)Cl NFJGHYXSHMSYFA-UHFFFAOYSA-K 0.000 description 1
- QMUWWEYTBMDCKJ-UHFFFAOYSA-M tridodecylstannanylium;chloride Chemical compound CCCCCCCCCCCC[Sn](Cl)(CCCCCCCCCCCC)CCCCCCCCCCCC QMUWWEYTBMDCKJ-UHFFFAOYSA-M 0.000 description 1
- MWKCRAHNOBACDT-UHFFFAOYSA-M tridodecylstannanylium;iodide Chemical compound CCCCCCCCCCCC[Sn](I)(CCCCCCCCCCCC)CCCCCCCCCCCC MWKCRAHNOBACDT-UHFFFAOYSA-M 0.000 description 1
- KQPIFPBKXYBDGV-UHFFFAOYSA-M triethylstannanylium;bromide Chemical compound CC[Sn](Br)(CC)CC KQPIFPBKXYBDGV-UHFFFAOYSA-M 0.000 description 1
- PRFPAWZEYOPUKM-UHFFFAOYSA-M triethylstannanylium;iodide Chemical compound CC[Sn](I)(CC)CC PRFPAWZEYOPUKM-UHFFFAOYSA-M 0.000 description 1
- SBNYZUTZEUZATG-UHFFFAOYSA-K triiodo(methyl)stannane Chemical compound C[Sn](I)(I)I SBNYZUTZEUZATG-UHFFFAOYSA-K 0.000 description 1
- MZGUIAFRJWSYJJ-UHFFFAOYSA-M trimethylstannanylium;bromide Chemical compound C[Sn](C)(C)Br MZGUIAFRJWSYJJ-UHFFFAOYSA-M 0.000 description 1
- XGRPNCOKLIMKBN-UHFFFAOYSA-M trimethylstannanylium;iodide Chemical compound C[Sn](C)(C)I XGRPNCOKLIMKBN-UHFFFAOYSA-M 0.000 description 1
- GQBRIYIRPORZOM-UHFFFAOYSA-M tripropylstannanylium;bromide Chemical compound CCC[Sn](Br)(CCC)CCC GQBRIYIRPORZOM-UHFFFAOYSA-M 0.000 description 1
- YQQBSHJWYVTQTA-UHFFFAOYSA-M tris(2-methylpropyl)stannanylium;bromide Chemical compound CC(C)C[Sn](Br)(CC(C)C)CC(C)C YQQBSHJWYVTQTA-UHFFFAOYSA-M 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
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US432396A US3862198A (en) | 1974-01-10 | 1974-01-10 | Catalyzed redistribution of alkyltin halides |
| US432396 | 1974-01-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1124740A true CA1124740A (en) | 1982-06-01 |
Family
ID=23715985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA211,734A Expired CA1124740A (en) | 1974-01-10 | 1974-10-18 | Catalyzed redistribution of alkyltin halides |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3862198A (en, 2012) |
| JP (1) | JPS6012359B2 (en, 2012) |
| AR (1) | AR218208A1 (en, 2012) |
| AT (1) | AT336633B (en, 2012) |
| BE (1) | BE824246A (en, 2012) |
| BR (1) | BR7500145A (en, 2012) |
| CA (1) | CA1124740A (en, 2012) |
| CH (1) | CH611309A5 (en, 2012) |
| DE (1) | DE2450709C3 (en, 2012) |
| FR (1) | FR2257596B1 (en, 2012) |
| GB (1) | GB1429918A (en, 2012) |
| IN (1) | IN140893B (en, 2012) |
| IT (1) | IT1022937B (en, 2012) |
| NL (1) | NL153205C (en, 2012) |
| ZA (1) | ZA746405B (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH581143A5 (en, 2012) * | 1973-08-16 | 1976-10-29 | Ciba Geigy Ag | |
| GB1541503A (en) * | 1976-01-23 | 1979-03-07 | Akzo Nv | Process for the preparation of organotin compounds |
| US4148814A (en) * | 1977-08-29 | 1979-04-10 | Pennwalt Corporation | Process for preparing monohydrocarbyltin trihalides |
| US4301085A (en) * | 1979-04-19 | 1981-11-17 | Ciba-Geigy Corporation | Process for the production of methyl-alkyl tin dichlorides |
| US4269782A (en) * | 1979-07-19 | 1981-05-26 | Argus Chemical Corporation | Preparation of mixtures of methyltin trichloride and dimethyltin dichloride from stannic chloride and dimethyltin dichloride |
| US4462935A (en) * | 1982-07-12 | 1984-07-31 | Gulf Research & Development Company | Quaternary phosphonium thiostannates |
| JPS61111679A (ja) * | 1984-11-05 | 1986-05-29 | Kayuu Shinpan Kk | 飲用酸味液の製造法 |
| JPS62159844U (en, 2012) * | 1986-03-28 | 1987-10-12 | ||
| EP1225177A1 (en) * | 2001-01-19 | 2002-07-24 | Atofina Vlissingen B.V. | Process for the production of monoalkyltin trihalides |
| US20050101716A1 (en) * | 2003-11-12 | 2005-05-12 | Ilze Bacaloglu | Liquid microemulsion stabilizer composition for halogen-containing polymers |
| US8633330B2 (en) * | 2010-07-01 | 2014-01-21 | Pmc Organometallix, Inc. | Process for preparing monoalkyltin trihalides and dialkyltin dihalides |
| WO2014204217A1 (ko) | 2013-06-19 | 2014-12-24 | 주식회사 엘지화학 | 점착제 조성물 |
| ES2701870T3 (es) | 2015-12-22 | 2019-02-26 | Arkema B V | Proceso para fabricar trihaluros de alquilestaño y su uso |
| EP4074717A1 (en) | 2021-04-13 | 2022-10-19 | BNT Chemicals GmbH | Method for cleaving alkyl tin halides |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL131496C (en, 2012) * | 1962-12-18 | 1900-01-01 | ||
| US3297732A (en) * | 1963-07-25 | 1967-01-10 | M & T Chemicals Inc | Process for preparing organotin halides |
| US3340283A (en) * | 1964-05-20 | 1967-09-05 | M & T Chemicals Inc | Preparation of organotin-trihalides |
| GB1064178A (en) * | 1964-08-27 | 1967-04-05 | Pure Chem Ltd | Improvements in the preparation of alkyl tin compounds |
| GB1115646A (en) * | 1964-09-18 | 1968-05-29 | Albright & Wilson Mfg Ltd | Improvements in the production of organotin compounds |
| US3519665A (en) * | 1968-01-25 | 1970-07-07 | Carlisle Chemical Works | Direct synthesis of dialkyltin dichloride |
| US3519667A (en) * | 1968-03-29 | 1970-07-07 | Carlisle Chemical Works | Process for preparing mono-methyl or ethyltin trichloride |
| NL7006926A (en, 2012) * | 1969-05-20 | 1970-11-24 |
-
1974
- 1974-01-10 US US432396A patent/US3862198A/en not_active Expired - Lifetime
- 1974-10-08 ZA ZA00746405A patent/ZA746405B/xx unknown
- 1974-10-16 IT IT28504/74A patent/IT1022937B/it active
- 1974-10-18 CA CA211,734A patent/CA1124740A/en not_active Expired
- 1974-10-21 NL NLAANVRAGE7413761,A patent/NL153205C/xx not_active IP Right Cessation
- 1974-10-23 JP JP49121555A patent/JPS6012359B2/ja not_active Expired
- 1974-10-24 GB GB4604374A patent/GB1429918A/en not_active Expired
- 1974-10-25 DE DE2450709A patent/DE2450709C3/de not_active Expired
- 1974-10-30 CH CH1452174A patent/CH611309A5/xx not_active IP Right Cessation
- 1974-10-31 AT AT876474A patent/AT336633B/de not_active IP Right Cessation
- 1974-11-18 IN IN2541/CAL/74A patent/IN140893B/en unknown
- 1974-11-25 AR AR256664A patent/AR218208A1/es active
-
1975
- 1975-01-08 FR FR7500397A patent/FR2257596B1/fr not_active Expired
- 1975-01-09 BR BR145/75A patent/BR7500145A/pt unknown
- 1975-01-09 BE BE152260A patent/BE824246A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2450709B2 (de) | 1977-03-03 |
| ZA746405B (en) | 1975-10-29 |
| DE2450709C3 (de) | 1982-06-24 |
| NL7413761A (nl) | 1975-07-14 |
| FR2257596A1 (en, 2012) | 1975-08-08 |
| BR7500145A (pt) | 1975-11-04 |
| NL153205B (nl) | 1977-05-16 |
| CH611309A5 (en, 2012) | 1979-05-31 |
| IT1022937B (it) | 1978-04-20 |
| JPS6012359B2 (ja) | 1985-04-01 |
| US3862198A (en) | 1975-01-21 |
| JPS50100026A (en, 2012) | 1975-08-08 |
| BE824246A (fr) | 1975-05-02 |
| IN140893B (en, 2012) | 1977-01-01 |
| NL153205C (nl) | 1983-04-18 |
| GB1429918A (en) | 1976-03-31 |
| AT336633B (de) | 1977-05-10 |
| DE2450709A1 (de) | 1975-07-17 |
| FR2257596B1 (en, 2012) | 1979-09-28 |
| AR218208A1 (es) | 1980-05-30 |
| ATA876474A (de) | 1976-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |