CH619961A5 - Process for the preparation of organotin mercaptides. - Google Patents
Process for the preparation of organotin mercaptides. Download PDFInfo
- Publication number
- CH619961A5 CH619961A5 CH110775A CH110775A CH619961A5 CH 619961 A5 CH619961 A5 CH 619961A5 CH 110775 A CH110775 A CH 110775A CH 110775 A CH110775 A CH 110775A CH 619961 A5 CH619961 A5 CH 619961A5
- Authority
- CH
- Switzerland
- Prior art keywords
- carbon atoms
- sulfide
- general formula
- compound
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 37
- 238000002360 preparation method Methods 0.000 title claims description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000000460 chlorine Substances 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000000010 aprotic solvent Substances 0.000 claims description 8
- 239000002002 slurry Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- KRZTYSCUOUIFHR-BDAKNGLRSA-N 2-[(1r,3s)-2,2-dimethyl-3-(2-oxopropyl)cyclopropyl]acetonitrile Chemical compound CC(=O)C[C@H]1[C@@H](CC#N)C1(C)C KRZTYSCUOUIFHR-BDAKNGLRSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 25
- -1 Äthylchloracetat Chemical compound 0.000 description 24
- QQOSUPHSTQYAOH-UHFFFAOYSA-N 6-methylheptyl 2-chloroacetate Chemical compound CC(C)CCCCCOC(=O)CCl QQOSUPHSTQYAOH-UHFFFAOYSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 229910052979 sodium sulfide Inorganic materials 0.000 description 18
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- 239000003921 oil Substances 0.000 description 15
- 150000003568 thioethers Chemical class 0.000 description 14
- 239000003381 stabilizer Substances 0.000 description 13
- ISHZHUBSDUTOAN-UHFFFAOYSA-N methyl(sulfanylidene)tin Chemical compound C[Sn]=S ISHZHUBSDUTOAN-UHFFFAOYSA-N 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 229920000915 polyvinyl chloride Polymers 0.000 description 11
- 239000004800 polyvinyl chloride Substances 0.000 description 11
- IUNVCWLKOOCPIT-UHFFFAOYSA-N 6-methylheptylsulfanyl 2-hydroxyacetate Chemical compound CC(C)CCCCCSOC(=O)CO IUNVCWLKOOCPIT-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical compound C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 description 8
- YFRLQYJXUZRYDN-UHFFFAOYSA-K trichloro(methyl)stannane Chemical compound C[Sn](Cl)(Cl)Cl YFRLQYJXUZRYDN-UHFFFAOYSA-K 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- BHWWTWCFLZECFZ-UHFFFAOYSA-N 2-sulfanylethyl octanoate Chemical compound CCCCCCCC(=O)OCCS BHWWTWCFLZECFZ-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- FAXZWVLVYZJMPC-UHFFFAOYSA-N butyl(sulfanylidene)tin Chemical compound CCCC[Sn]=S FAXZWVLVYZJMPC-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- IZRRIUZHPNJUCU-UHFFFAOYSA-N trimethyl(trimethylstannylsulfanyl)stannane Chemical compound C[Sn](C)(C)S[Sn](C)(C)C IZRRIUZHPNJUCU-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- JJPZOIJCDNHCJP-UHFFFAOYSA-N dibutyl(sulfanylidene)tin Chemical compound CCCC[Sn](=S)CCCC JJPZOIJCDNHCJP-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- BDIWFCKBPZPBQT-UHFFFAOYSA-N tributyl(tributylstannylsulfanyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)S[Sn](CCCC)(CCCC)CCCC BDIWFCKBPZPBQT-UHFFFAOYSA-N 0.000 description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- SOGXBRHOWDEKQB-UHFFFAOYSA-N benzyl 2-chloroacetate Chemical compound ClCC(=O)OCC1=CC=CC=C1 SOGXBRHOWDEKQB-UHFFFAOYSA-N 0.000 description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 4
- 229940073608 benzyl chloride Drugs 0.000 description 4
- 229940089960 chloroacetate Drugs 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- VEFKNRVOMTXTSC-KTKRTIGZSA-N 2-chloroethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCl VEFKNRVOMTXTSC-KTKRTIGZSA-N 0.000 description 3
- GPOGMJLHWQHEGF-UHFFFAOYSA-N 2-chloroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCl GPOGMJLHWQHEGF-UHFFFAOYSA-N 0.000 description 3
- QLBIYHGOHHPBCC-UHFFFAOYSA-N 2-chloroethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCl QLBIYHGOHHPBCC-UHFFFAOYSA-N 0.000 description 3
- PTHHPBYJSGIOMH-UHFFFAOYSA-N 6-methylheptyl 2-bromoacetate Chemical compound CC(C)CCCCCOC(=O)CBr PTHHPBYJSGIOMH-UHFFFAOYSA-N 0.000 description 3
- KKDGZGXVTXSTLK-UHFFFAOYSA-N 6-methylheptyl 3-chloropropanoate Chemical compound CC(C)CCCCCOC(=O)CCCl KKDGZGXVTXSTLK-UHFFFAOYSA-N 0.000 description 3
- VBCZQAZDKKLLQJ-UHFFFAOYSA-N 8-methylnonyl 2-chloroacetate Chemical compound CC(C)CCCCCCCOC(=O)CCl VBCZQAZDKKLLQJ-UHFFFAOYSA-N 0.000 description 3
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VNMJPBIKMFZOQP-UHFFFAOYSA-N benzyl(sulfanylidene)tin Chemical compound S=[Sn]CC1=CC=CC=C1 VNMJPBIKMFZOQP-UHFFFAOYSA-N 0.000 description 3
- YJRGMUWRPCPLNH-UHFFFAOYSA-N butyl 2-chloroacetate Chemical compound CCCCOC(=O)CCl YJRGMUWRPCPLNH-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- IBFHBLOKQVCABG-UHFFFAOYSA-N cyclohexyl 2-chloroacetate Chemical compound ClCC(=O)OC1CCCCC1 IBFHBLOKQVCABG-UHFFFAOYSA-N 0.000 description 3
- PMISWFLCGNYKSG-UHFFFAOYSA-N cyclohexyl(sulfanylidene)tin Chemical compound S=[Sn]C1CCCCC1 PMISWFLCGNYKSG-UHFFFAOYSA-N 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 3
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 3
- QXOMWNGIGKRLJC-UHFFFAOYSA-N octadecyl(sulfanylidene)tin Chemical compound CCCCCCCCCCCCCCCCCC[Sn]=S QXOMWNGIGKRLJC-UHFFFAOYSA-N 0.000 description 3
- RFHIHPWSONFOHR-UHFFFAOYSA-N octyl(sulfanylidene)tin Chemical compound CCCCCCCC[Sn]=S RFHIHPWSONFOHR-UHFFFAOYSA-N 0.000 description 3
- ABHWWAKMQXWYLD-UHFFFAOYSA-N phenyl(sulfanylidene)tin Chemical compound S=[Sn]C1=CC=CC=C1 ABHWWAKMQXWYLD-UHFFFAOYSA-N 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- AOUSBQVEVZBMNI-UHFFFAOYSA-N 2-bromoethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCBr AOUSBQVEVZBMNI-UHFFFAOYSA-N 0.000 description 2
- SIUTWYZMSNPSIO-UHFFFAOYSA-N 2-chloroethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCCl SIUTWYZMSNPSIO-UHFFFAOYSA-N 0.000 description 2
- VIRWKAJWTKAIMA-UHFFFAOYSA-N 2-chloroethyl acetate Chemical compound CC(=O)OCCCl VIRWKAJWTKAIMA-UHFFFAOYSA-N 0.000 description 2
- JYPRYSVZABJWGS-UHFFFAOYSA-N 2-chloroethyl butanoate Chemical compound CCCC(=O)OCCCl JYPRYSVZABJWGS-UHFFFAOYSA-N 0.000 description 2
- CPFFARIYTPCNJA-UHFFFAOYSA-N 2-chloroethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCCl CPFFARIYTPCNJA-UHFFFAOYSA-N 0.000 description 2
- XAARWHAYKZHMOM-UHFFFAOYSA-N 2-chloroethyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OCCCl XAARWHAYKZHMOM-UHFFFAOYSA-N 0.000 description 2
- XBVCXCNGNQZCES-UHFFFAOYSA-N 2-chloroethyl octanoate Chemical compound CCCCCCCC(=O)OCCCl XBVCXCNGNQZCES-UHFFFAOYSA-N 0.000 description 2
- WHBAYNMEIXUTJV-UHFFFAOYSA-N 2-chloroethyl prop-2-enoate Chemical compound ClCCOC(=O)C=C WHBAYNMEIXUTJV-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 description 2
- ICVOMKVHGRDKFL-UHFFFAOYSA-N 6-methylheptyl 3-bromopropanoate Chemical compound CC(C)CCCCCOC(=O)CCBr ICVOMKVHGRDKFL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229910017974 NH40H Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- DAZHHCXYQAQGOM-UHFFFAOYSA-N bis(4-methylphenyl)-sulfanylidenetin Chemical compound C1=CC(C)=CC=C1[Sn](=S)C1=CC=C(C)C=C1 DAZHHCXYQAQGOM-UHFFFAOYSA-N 0.000 description 2
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 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
- HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 2
- JTYINBWQGXHZLX-UHFFFAOYSA-N cyclohexyl 2-bromoacetate Chemical compound BrCC(=O)OC1CCCCC1 JTYINBWQGXHZLX-UHFFFAOYSA-N 0.000 description 2
- WLAYVQKPZABXSY-UHFFFAOYSA-N decyl 2-chloroacetate Chemical compound CCCCCCCCCCOC(=O)CCl WLAYVQKPZABXSY-UHFFFAOYSA-N 0.000 description 2
- IKNDNAVUDFNJGP-UHFFFAOYSA-N dibenzyl(sulfanylidene)tin Chemical compound C=1C=CC=CC=1C[Sn](=S)CC1=CC=CC=C1 IKNDNAVUDFNJGP-UHFFFAOYSA-N 0.000 description 2
- OAHCTWDXJQEECF-UHFFFAOYSA-N dicyclohexyl(sulfanylidene)tin Chemical compound C1CCCCC1[Sn](=S)C1CCCCC1 OAHCTWDXJQEECF-UHFFFAOYSA-N 0.000 description 2
- IRFPIPNMASANJY-UHFFFAOYSA-L dimethyltin(2+);2-(6-methylheptoxy)-2-oxoethanethiolate Chemical compound CC(C)CCCCCOC(=O)CS[Sn](C)(C)SCC(=O)OCCCCCC(C)C IRFPIPNMASANJY-UHFFFAOYSA-L 0.000 description 2
- RFAIKXASDCRKEP-UHFFFAOYSA-N dioctyl(sulfanylidene)tin Chemical compound CCCCCCCC[Sn](=S)CCCCCCCC RFAIKXASDCRKEP-UHFFFAOYSA-N 0.000 description 2
- NCUROSDPAOGNHW-UHFFFAOYSA-N dodecyl 3-chloropropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCCl NCUROSDPAOGNHW-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- OJGRZJILAIHWIY-UHFFFAOYSA-N hexyl 2-chloroacetate Chemical compound CCCCCCOC(=O)CCl OJGRZJILAIHWIY-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000005394 methallyl group Chemical group 0.000 description 2
- CSHCPECZJIEGJF-UHFFFAOYSA-N methyltin Chemical compound [Sn]C CSHCPECZJIEGJF-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229940049964 oleate Drugs 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- ISYUCUGTDNJIHV-UHFFFAOYSA-N propyl 2-bromoacetate Chemical compound CCCOC(=O)CBr ISYUCUGTDNJIHV-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- AFNRRBXCCXDRPS-UHFFFAOYSA-N tin(ii) sulfide Chemical compound [Sn]=S AFNRRBXCCXDRPS-UHFFFAOYSA-N 0.000 description 2
- XMHKTINRBAKEDS-UHFFFAOYSA-N trioctyltin Chemical compound CCCCCCCC[Sn](CCCCCCCC)CCCCCCCC XMHKTINRBAKEDS-UHFFFAOYSA-N 0.000 description 2
- NTCQOKPUDSWFJF-UHFFFAOYSA-N triphenyl(triphenylstannylsulfanyl)stannane Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)S[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NTCQOKPUDSWFJF-UHFFFAOYSA-N 0.000 description 2
- AGAJPZSVOINNHN-UHFFFAOYSA-N (4-butylphenyl)-sulfanylidenetin Chemical compound CCCCC1=CC=C([Sn]=S)C=C1 AGAJPZSVOINNHN-UHFFFAOYSA-N 0.000 description 1
- DYDLBLLDYJSEIU-UHFFFAOYSA-N (4-methylphenyl)-sulfanylidenetin Chemical compound CC1=CC=C([Sn]=S)C=C1 DYDLBLLDYJSEIU-UHFFFAOYSA-N 0.000 description 1
- TXECTBGVEUDNSL-UHFFFAOYSA-N 1-acetyloxyprop-2-enyl acetate Chemical compound CC(=O)OC(C=C)OC(C)=O TXECTBGVEUDNSL-UHFFFAOYSA-N 0.000 description 1
- FPBWSPZHCJXUBL-UHFFFAOYSA-N 1-chloro-1-fluoroethene Chemical group FC(Cl)=C FPBWSPZHCJXUBL-UHFFFAOYSA-N 0.000 description 1
- KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 description 1
- KPERNTILGCKGAA-UHFFFAOYSA-L 2,8-dimethyl-2-(6-methylheptyl)nonanethioate dimethyltin(2+) Chemical compound C(CCCCC(C)C)C(C(=S)[O-])(C)CCCCCC(C)C.C[Sn+2]C.C(CCCCC(C)C)C(C(=S)[O-])(C)CCCCCC(C)C KPERNTILGCKGAA-UHFFFAOYSA-L 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- MXJCRIAXILAHFT-UHFFFAOYSA-N 2-bromoethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCBr MXJCRIAXILAHFT-UHFFFAOYSA-N 0.000 description 1
- RGHQKFQZGLKBCF-UHFFFAOYSA-N 2-bromoethyl acetate Chemical compound CC(=O)OCCBr RGHQKFQZGLKBCF-UHFFFAOYSA-N 0.000 description 1
- KXBZGFSUCDSJKC-UHFFFAOYSA-N 2-bromoethyl butanoate Chemical compound CCCC(=O)OCCBr KXBZGFSUCDSJKC-UHFFFAOYSA-N 0.000 description 1
- FORDMBWONWFLHF-UHFFFAOYSA-N 2-bromoethyl decanoate Chemical compound CCCCCCCCCC(=O)OCCBr FORDMBWONWFLHF-UHFFFAOYSA-N 0.000 description 1
- OJTJEBDBHVSJBW-UHFFFAOYSA-N 2-bromoethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCBr OJTJEBDBHVSJBW-UHFFFAOYSA-N 0.000 description 1
- PJLSBYYRTNXSCE-UHFFFAOYSA-N 2-bromoethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCBr PJLSBYYRTNXSCE-UHFFFAOYSA-N 0.000 description 1
- TUTKMABCZPJQRW-UHFFFAOYSA-N 2-bromoethyl icosanoate Chemical compound BrCCOC(CCCCCCCCCCCCCCCCCCC)=O TUTKMABCZPJQRW-UHFFFAOYSA-N 0.000 description 1
- MXXJTDHLUDXSAS-UHFFFAOYSA-N 2-bromoethyl nonanoate Chemical compound CCCCCCCCC(=O)OCCBr MXXJTDHLUDXSAS-UHFFFAOYSA-N 0.000 description 1
- MYNLFGHAZLGJGP-UHFFFAOYSA-N 2-bromoethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCBr MYNLFGHAZLGJGP-UHFFFAOYSA-N 0.000 description 1
- WJGIYNCROZEFBS-UHFFFAOYSA-N 2-bromoethyl pentanoate Chemical compound CCCCC(=O)OCCBr WJGIYNCROZEFBS-UHFFFAOYSA-N 0.000 description 1
- CDZAAIHWZYWBSS-UHFFFAOYSA-N 2-bromoethyl prop-2-enoate Chemical compound BrCCOC(=O)C=C CDZAAIHWZYWBSS-UHFFFAOYSA-N 0.000 description 1
- FBSPHFKZJKWNEC-UHFFFAOYSA-N 2-bromoethyl propanoate Chemical compound CCC(=O)OCCBr FBSPHFKZJKWNEC-UHFFFAOYSA-N 0.000 description 1
- JFNBJTDMUIDJBU-HZJYTTRNSA-N 2-chloroethyl (9z,12z)-octadeca-9,12-dienoate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCCCl JFNBJTDMUIDJBU-HZJYTTRNSA-N 0.000 description 1
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- HDNSRULOUMXYKG-UHFFFAOYSA-N octadecyl 2-chloroacetate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCl HDNSRULOUMXYKG-UHFFFAOYSA-N 0.000 description 1
- YQCZLISEEYFBDQ-UHFFFAOYSA-N octadecyl 2-chloropropanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)Cl YQCZLISEEYFBDQ-UHFFFAOYSA-N 0.000 description 1
- DJEOKDIGZNAGNM-UHFFFAOYSA-N octadecyl 3-bromopropanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCBr DJEOKDIGZNAGNM-UHFFFAOYSA-N 0.000 description 1
- IWNDNJGFFCNPKN-UHFFFAOYSA-N octadecyl 3-chloropropanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCl IWNDNJGFFCNPKN-UHFFFAOYSA-N 0.000 description 1
- BOCFEZOZUMAGFA-UHFFFAOYSA-N octyl 2-bromopropanoate Chemical compound CCCCCCCCOC(=O)C(C)Br BOCFEZOZUMAGFA-UHFFFAOYSA-N 0.000 description 1
- BGMYDZVCAOVIPM-UHFFFAOYSA-N octyl 2-chloropropanoate Chemical compound CCCCCCCCOC(=O)C(C)Cl BGMYDZVCAOVIPM-UHFFFAOYSA-N 0.000 description 1
- RTGDICWSTDGLNC-UHFFFAOYSA-N octyl 3-bromopropanoate Chemical compound CCCCCCCCOC(=O)CCBr RTGDICWSTDGLNC-UHFFFAOYSA-N 0.000 description 1
- APSFWUHAPFXKHS-UHFFFAOYSA-N octyl 3-chloropropanoate Chemical compound CCCCCCCCOC(=O)CCCl APSFWUHAPFXKHS-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- FDCTVCOKDZZPRP-UHFFFAOYSA-N prop-2-enyl 2-chloropropanoate Chemical compound CC(Cl)C(=O)OCC=C FDCTVCOKDZZPRP-UHFFFAOYSA-N 0.000 description 1
- CTPKUPQTROHREC-UHFFFAOYSA-N prop-2-enyl 3-chloropropanoate Chemical compound ClCCC(=O)OCC=C CTPKUPQTROHREC-UHFFFAOYSA-N 0.000 description 1
- VODRWDBLLGYRJT-UHFFFAOYSA-N propan-2-yl 2-chloroacetate Chemical compound CC(C)OC(=O)CCl VODRWDBLLGYRJT-UHFFFAOYSA-N 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- QJZNRCWAXUGABH-UHFFFAOYSA-N propyl 2-chloroacetate Chemical compound CCCOC(=O)CCl QJZNRCWAXUGABH-UHFFFAOYSA-N 0.000 description 1
- XVDQGLUGZORASO-UHFFFAOYSA-N propyl 2-chloropropanoate Chemical compound CCCOC(=O)C(C)Cl XVDQGLUGZORASO-UHFFFAOYSA-N 0.000 description 1
- DXFHVUUGWSXHQY-UHFFFAOYSA-N propyl 3-bromopropanoate Chemical compound CCCOC(=O)CCBr DXFHVUUGWSXHQY-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- KUZUNHDCZIJWAO-UHFFFAOYSA-N tetradecyl 3-chloropropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCl KUZUNHDCZIJWAO-UHFFFAOYSA-N 0.000 description 1
- RLKWXZLMMDRNDU-UHFFFAOYSA-N tribenzyl(tribenzylstannylsulfanyl)stannane Chemical compound C=1C=CC=CC=1C[Sn](S[Sn](CC=1C=CC=CC=1)(CC=1C=CC=CC=1)CC=1C=CC=CC=1)(CC=1C=CC=CC=1)CC1=CC=CC=C1 RLKWXZLMMDRNDU-UHFFFAOYSA-N 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
- NBTHYJWPOYZDHL-UHFFFAOYSA-N tricyclohexyl(tricyclohexylstannylsulfanyl)stannane Chemical compound C1CCCCC1[Sn](C1CCCCC1)(C1CCCCC1)S[Sn](C1CCCCC1)(C1CCCCC1)C1CCCCC1 NBTHYJWPOYZDHL-UHFFFAOYSA-N 0.000 description 1
- CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical compound CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
- IGVWFLOSJOIPES-UHFFFAOYSA-N tris(4-methylphenyl)tin Chemical compound C1=CC(C)=CC=C1[Sn](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 IGVWFLOSJOIPES-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- C07F7/226—Compounds with one or more Sn-S 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
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/449,435 US3970678A (en) | 1974-03-08 | 1974-03-08 | Organotin mercaptide process |
| US479142A US3931263A (en) | 1974-06-13 | 1974-06-13 | Organotin mercaptide process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH619961A5 true CH619961A5 (en) | 1980-10-31 |
Family
ID=27035694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH110775A CH619961A5 (en) | 1974-03-08 | 1975-01-30 | Process for the preparation of organotin mercaptides. |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS50121232A (fr) |
| AT (1) | AT336635B (fr) |
| BR (1) | BR7501284A (fr) |
| CA (1) | CA1052804A (fr) |
| CH (1) | CH619961A5 (fr) |
| DE (3) | DE2559446C3 (fr) |
| ES (1) | ES433740A1 (fr) |
| FR (1) | FR2263248B1 (fr) |
| GB (1) | GB1443684A (fr) |
| IN (1) | IN142694B (fr) |
| IT (1) | IT1026869B (fr) |
| NL (1) | NL7501031A (fr) |
| PH (1) | PH13175A (fr) |
| SE (3) | SE7502024L (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3970678A (en) * | 1974-03-08 | 1976-07-20 | Cincinnati Milacron Chemicals, Inc. | Organotin mercaptide process |
| US4118371A (en) * | 1977-04-29 | 1978-10-03 | Cincinnati Milacron Chemicals Inc. | Organotin mercaptoalkanol ester sulfide stabilizers for PVC resins |
| DE2928679A1 (de) * | 1978-07-20 | 1980-02-07 | M & T Chemicals Inc | Verfahren zur herstellung von organozinnverbindungen |
| US4254017A (en) * | 1978-11-13 | 1981-03-03 | M&T Chemicals Inc. | Organotin mercaptoalkanol esters and alkoxides containing sulfide groups |
| GB2139625B (en) * | 1983-05-03 | 1987-05-13 | Ciba Geigy Ag | Novel organo-tin pvc stabilisers |
-
1974
- 1974-12-04 CA CA215,250A patent/CA1052804A/fr not_active Expired
- 1974-12-09 IT IT30298/74A patent/IT1026869B/it active
-
1975
- 1975-01-08 PH PH16689A patent/PH13175A/en unknown
- 1975-01-11 ES ES433740A patent/ES433740A1/es not_active Expired
- 1975-01-13 GB GB132375A patent/GB1443684A/en not_active Expired
- 1975-01-16 IN IN92/CAL/75A patent/IN142694B/en unknown
- 1975-01-29 DE DE2559446A patent/DE2559446C3/de not_active Expired
- 1975-01-29 DE DE2559531A patent/DE2559531C3/de not_active Expired
- 1975-01-29 NL NL7501031A patent/NL7501031A/xx not_active Application Discontinuation
- 1975-01-29 DE DE2503554A patent/DE2503554C3/de not_active Expired
- 1975-01-30 CH CH110775A patent/CH619961A5/de not_active IP Right Cessation
- 1975-02-12 JP JP50016991A patent/JPS50121232A/ja active Pending
- 1975-02-14 AT AT111775A patent/AT336635B/de not_active IP Right Cessation
- 1975-02-24 SE SE7502024A patent/SE7502024L/xx unknown
- 1975-03-05 BR BR1284/75A patent/BR7501284A/pt unknown
- 1975-03-07 FR FR7507142A patent/FR2263248B1/fr not_active Expired
-
1978
- 1978-05-03 SE SE7805103A patent/SE7805103L/xx unknown
- 1978-05-03 SE SE7805089A patent/SE7805089L/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU7739075A (en) | 1976-07-22 |
| DE2503554C3 (de) | 1978-03-30 |
| IN142694B (fr) | 1977-08-13 |
| IT1026869B (it) | 1978-10-20 |
| DE2559446A1 (de) | 1976-12-09 |
| BR7501284A (pt) | 1975-12-02 |
| PH13175A (en) | 1980-01-08 |
| DE2559446C3 (de) | 1979-08-09 |
| JPS50121232A (fr) | 1975-09-23 |
| FR2263248B1 (fr) | 1978-12-29 |
| FR2263248A1 (fr) | 1975-10-03 |
| ES433740A1 (es) | 1977-02-16 |
| DE2559446B2 (de) | 1978-11-16 |
| GB1443684A (en) | 1976-07-21 |
| DE2559531A1 (de) | 1977-03-03 |
| ATA111775A (de) | 1976-09-15 |
| SE7805089L (sv) | 1978-05-03 |
| DE2559531B2 (de) | 1980-05-14 |
| AT336635B (de) | 1977-05-10 |
| SE7502024L (fr) | 1975-09-09 |
| NL7501031A (nl) | 1975-09-10 |
| CA1052804A (fr) | 1979-04-17 |
| SE7805103L (sv) | 1978-05-03 |
| DE2559531C3 (de) | 1982-03-04 |
| DE2503554A1 (de) | 1975-09-11 |
| DE2503554B2 (de) | 1977-08-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |