CA1052804A - Organotin mercaptide process - Google Patents
Organotin mercaptide processInfo
- Publication number
- CA1052804A CA1052804A CA215,250A CA215250A CA1052804A CA 1052804 A CA1052804 A CA 1052804A CA 215250 A CA215250 A CA 215250A CA 1052804 A CA1052804 A CA 1052804A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- process according
- alkyl
- sulfide
- alkenyl
- 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
- 238000000034 method Methods 0.000 title claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 239000000460 chlorine Substances 0.000 claims abstract description 33
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 20
- 229910001868 water Inorganic materials 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
- 239000000010 aprotic solvent Substances 0.000 claims abstract description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000005394 methallyl group Chemical group 0.000 claims abstract 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 30
- -1 R1 stands for Chemical group 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 18
- 239000002002 slurry Substances 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 4
- 150000003568 thioethers Chemical class 0.000 abstract description 13
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052794 bromium Chemical group 0.000 abstract description 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- QQOSUPHSTQYAOH-UHFFFAOYSA-N 6-methylheptyl 2-chloroacetate Chemical compound CC(C)CCCCCOC(=O)CCl QQOSUPHSTQYAOH-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 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 16
- 239000003921 oil Substances 0.000 description 16
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 229910052979 sodium sulfide Inorganic materials 0.000 description 13
- ISHZHUBSDUTOAN-UHFFFAOYSA-N methyl(sulfanylidene)tin Chemical compound C[Sn]=S ISHZHUBSDUTOAN-UHFFFAOYSA-N 0.000 description 12
- IUNVCWLKOOCPIT-UHFFFAOYSA-N 6-methylheptylsulfanyl 2-hydroxyacetate Chemical compound CC(C)CCCCCSOC(=O)CO IUNVCWLKOOCPIT-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 229960005419 nitrogen Drugs 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 239000003381 stabilizer Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 235000013350 formula milk Nutrition 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 229920002554 vinyl polymer Polymers 0.000 description 7
- BHWWTWCFLZECFZ-UHFFFAOYSA-N 2-sulfanylethyl octanoate Chemical compound CCCCCCCC(=O)OCCS BHWWTWCFLZECFZ-UHFFFAOYSA-N 0.000 description 6
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 6
- 229940089960 chloroacetate Drugs 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- FAXZWVLVYZJMPC-UHFFFAOYSA-N butyl(sulfanylidene)tin Chemical compound CCCC[Sn]=S FAXZWVLVYZJMPC-UHFFFAOYSA-N 0.000 description 5
- JJPZOIJCDNHCJP-UHFFFAOYSA-N dibutyl(sulfanylidene)tin Chemical compound CCCC[Sn](=S)CCCC JJPZOIJCDNHCJP-UHFFFAOYSA-N 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000006077 pvc stabilizer Substances 0.000 description 5
- 239000007858 starting material Substances 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- PMISWFLCGNYKSG-UHFFFAOYSA-N cyclohexyl(sulfanylidene)tin Chemical compound S=[Sn]C1CCCCC1 PMISWFLCGNYKSG-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- IZRRIUZHPNJUCU-UHFFFAOYSA-N trimethyl(trimethylstannylsulfanyl)stannane Chemical compound C[Sn](C)(C)S[Sn](C)(C)C IZRRIUZHPNJUCU-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 125000005999 2-bromoethyl group Chemical group 0.000 description 3
- VEFKNRVOMTXTSC-KTKRTIGZSA-N 2-chloroethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCl VEFKNRVOMTXTSC-KTKRTIGZSA-N 0.000 description 3
- QLBIYHGOHHPBCC-UHFFFAOYSA-N 2-chloroethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCl QLBIYHGOHHPBCC-UHFFFAOYSA-N 0.000 description 3
- XBVCXCNGNQZCES-UHFFFAOYSA-N 2-chloroethyl octanoate Chemical compound CCCCCCCC(=O)OCCCl XBVCXCNGNQZCES-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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 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
- 229920001577 copolymer Polymers 0.000 description 3
- IBFHBLOKQVCABG-UHFFFAOYSA-N cyclohexyl 2-chloroacetate Chemical compound ClCC(=O)OC1CCCCC1 IBFHBLOKQVCABG-UHFFFAOYSA-N 0.000 description 3
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 3
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 3
- CSHCPECZJIEGJF-UHFFFAOYSA-N methyltin Chemical compound [Sn]C CSHCPECZJIEGJF-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
- 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
- GPOGMJLHWQHEGF-UHFFFAOYSA-N 2-chloroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCl GPOGMJLHWQHEGF-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
- WHBAYNMEIXUTJV-UHFFFAOYSA-N 2-chloroethyl prop-2-enoate Chemical compound ClCCOC(=O)C=C WHBAYNMEIXUTJV-UHFFFAOYSA-N 0.000 description 2
- QZBQQHUYQKGPLQ-UHFFFAOYSA-N 2-ethylhexyl 2-chloroacetate Chemical compound CCCCC(CC)COC(=O)CCl QZBQQHUYQKGPLQ-UHFFFAOYSA-N 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
- PTHHPBYJSGIOMH-UHFFFAOYSA-N 6-methylheptyl 2-bromoacetate Chemical compound CC(C)CCCCCOC(=O)CBr PTHHPBYJSGIOMH-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
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 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
- 125000004429 atom Chemical group 0.000 description 2
- VNMJPBIKMFZOQP-UHFFFAOYSA-N benzyl(sulfanylidene)tin Chemical compound S=[Sn]CC1=CC=CC=C1 VNMJPBIKMFZOQP-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
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 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
- PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical compound C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 229940113088 dimethylacetamide Drugs 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
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 2
- OJGRZJILAIHWIY-UHFFFAOYSA-N hexyl 2-chloroacetate Chemical compound CCCCCCOC(=O)CCl OJGRZJILAIHWIY-UHFFFAOYSA-N 0.000 description 2
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- QXOMWNGIGKRLJC-UHFFFAOYSA-N octadecyl(sulfanylidene)tin Chemical compound CCCCCCCCCCCCCCCCCC[Sn]=S QXOMWNGIGKRLJC-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- ISYUCUGTDNJIHV-UHFFFAOYSA-N propyl 2-bromoacetate Chemical compound CCCOC(=O)CBr ISYUCUGTDNJIHV-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 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 2
- YFRLQYJXUZRYDN-UHFFFAOYSA-K trichloro(methyl)stannane Chemical compound C[Sn](Cl)(Cl)Cl YFRLQYJXUZRYDN-UHFFFAOYSA-K 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
- VTHGHWCUKLJZBL-UHFFFAOYSA-N (4-methylphenyl)tin Chemical compound CC1=CC=C([Sn])C=C1 VTHGHWCUKLJZBL-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
- SFGBOBMTMFHZJH-UHFFFAOYSA-N 1-chloro-6-methylheptane Chemical compound CC(C)CCCCCCl SFGBOBMTMFHZJH-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
- 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
- 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
- WRIOEJKKXQEEFB-UHFFFAOYSA-N 2-chloroethyl decanoate Chemical compound CCCCCCCCCC(=O)OCCCl WRIOEJKKXQEEFB-UHFFFAOYSA-N 0.000 description 1
- PPRUSMUBWUQYRY-UHFFFAOYSA-N 2-chloroethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCl PPRUSMUBWUQYRY-UHFFFAOYSA-N 0.000 description 1
- YTLCJSNLBLLPLD-UHFFFAOYSA-N 2-chloroethyl pentanoate Chemical compound CCCCC(=O)OCCCl YTLCJSNLBLLPLD-UHFFFAOYSA-N 0.000 description 1
- VKSJVMZEQNIBNA-UHFFFAOYSA-N 2-chloroethyl propanoate Chemical compound CCC(=O)OCCCl VKSJVMZEQNIBNA-UHFFFAOYSA-N 0.000 description 1
- MPNMNLLETRXDEX-UHFFFAOYSA-N 2-chloroethyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCCCl MPNMNLLETRXDEX-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 1
- MAHUQNLJZDBIQD-UHFFFAOYSA-N 2-ethylhexyl 2-bromoacetate Chemical compound CCCCC(CC)COC(=O)CBr MAHUQNLJZDBIQD-UHFFFAOYSA-N 0.000 description 1
- GARYLPJZODVGRE-UHFFFAOYSA-N 2-ethylhexyl 3-chloropropanoate Chemical compound CCCCC(CC)COC(=O)CCCl GARYLPJZODVGRE-UHFFFAOYSA-N 0.000 description 1
- NKGSELHTEZTNOO-UHFFFAOYSA-N 2-ethylhexyl(sulfanylidene)tin Chemical compound CCCCC(CC)C[Sn]=S NKGSELHTEZTNOO-UHFFFAOYSA-N 0.000 description 1
- GJBREVNFUCHEFU-UHFFFAOYSA-N 2-methylprop-2-enyl 2-chloroacetate Chemical compound CC(=C)COC(=O)CCl GJBREVNFUCHEFU-UHFFFAOYSA-N 0.000 description 1
- MVUXHXZFGGRGNC-UHFFFAOYSA-N 2-phenylethyl 2-chloroacetate Chemical compound ClCC(=O)OCCC1=CC=CC=C1 MVUXHXZFGGRGNC-UHFFFAOYSA-N 0.000 description 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
- KYTSZEXQGFZBPS-UHFFFAOYSA-N 3-bromopropyl octadecanoate Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)OCCCBr KYTSZEXQGFZBPS-UHFFFAOYSA-N 0.000 description 1
- UHBAWOXYQROEIH-UHFFFAOYSA-N 3-chloro-4-(2-chlorobut-3-enoxy)but-1-ene Chemical compound C=CC(Cl)COCC(Cl)C=C UHBAWOXYQROEIH-UHFFFAOYSA-N 0.000 description 1
- FNYLFWGITLMOHA-UHFFFAOYSA-N 4-chloro-6-methoxy-2-methylsulfanylpyrimidine Chemical compound COC1=CC(Cl)=NC(SC)=N1 FNYLFWGITLMOHA-UHFFFAOYSA-N 0.000 description 1
- WNXNUPJZWYOKMW-UHFFFAOYSA-M 5-bromopentanoate Chemical compound [O-]C(=O)CCCCBr WNXNUPJZWYOKMW-UHFFFAOYSA-M 0.000 description 1
- OAAGDVLVOKMRCQ-UHFFFAOYSA-N 5-piperidin-4-yl-3-pyridin-4-yl-1,2,4-oxadiazole Chemical compound C1CNCCC1C1=NC(C=2C=CN=CC=2)=NO1 OAAGDVLVOKMRCQ-UHFFFAOYSA-N 0.000 description 1
- QEEGKWZARMKHTC-UHFFFAOYSA-N 6-methylheptyl 2-bromopropanoate Chemical compound CC(C)CCCCCOC(=O)C(C)Br QEEGKWZARMKHTC-UHFFFAOYSA-N 0.000 description 1
- TYGVZAXOIFOTMN-UHFFFAOYSA-N 6-methylheptyl 2-chloropropanoate Chemical compound CC(C)CCCCCOC(=O)C(C)Cl TYGVZAXOIFOTMN-UHFFFAOYSA-N 0.000 description 1
- ZHUWXKIPGGZNJW-UHFFFAOYSA-N 6-methylheptyl 3-sulfanylpropanoate Chemical compound CC(C)CCCCCOC(=O)CCS ZHUWXKIPGGZNJW-UHFFFAOYSA-N 0.000 description 1
- UPUQMZPQGQLBPC-UHFFFAOYSA-K 8-methyl-2-(6-methylheptyl)-2-(6-methylheptylsulfanyl)nonanoate methyltin(3+) Chemical compound [Sn+3]C.CC(C)CCCCCSC(CCCCCC(C)C)(CCCCCC(C)C)C([O-])=O.CC(C)CCCCCSC(CCCCCC(C)C)(CCCCCC(C)C)C([O-])=O.CC(C)CCCCCSC(CCCCCC(C)C)(CCCCCC(C)C)C([O-])=O UPUQMZPQGQLBPC-UHFFFAOYSA-K 0.000 description 1
- IZKQAJZIRVQIDE-UHFFFAOYSA-N 8-methylnonyl 2-bromoacetate Chemical compound CC(C)CCCCCCCOC(=O)CBr IZKQAJZIRVQIDE-UHFFFAOYSA-N 0.000 description 1
- WUEZASWOJSPUOX-UHFFFAOYSA-N 8-methylnonyl 2-bromopropanoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)Br WUEZASWOJSPUOX-UHFFFAOYSA-N 0.000 description 1
- CXKPYMAASHCPKO-UHFFFAOYSA-N 8-methylnonyl 2-chloropropanoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)Cl CXKPYMAASHCPKO-UHFFFAOYSA-N 0.000 description 1
- AUPLHAIYTJCKEZ-UHFFFAOYSA-N 8-methylnonyl 3-chloropropanoate Chemical compound CC(C)CCCCCCCOC(=O)CCCl AUPLHAIYTJCKEZ-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OPMJTJRQQPPLPH-UHFFFAOYSA-N C(=C)[Sn]=S Chemical compound C(=C)[Sn]=S OPMJTJRQQPPLPH-UHFFFAOYSA-N 0.000 description 1
- BEBFQWIUDDKATE-UHFFFAOYSA-N C(CCCCCCCC=C/CCCCCCCC)[Sn]=S Chemical compound C(CCCCCCCC=C/CCCCCCCC)[Sn]=S BEBFQWIUDDKATE-UHFFFAOYSA-N 0.000 description 1
- CZJASHFZOAPREC-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)[Sn](CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC Chemical compound C(CCCCCCCCCCCCCCCCC)[Sn](CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC CZJASHFZOAPREC-UHFFFAOYSA-N 0.000 description 1
- LNRIDJWQXPOFOW-UHFFFAOYSA-N C1(CCCC1)[Sn] Chemical compound C1(CCCC1)[Sn] LNRIDJWQXPOFOW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical group CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 description 1
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241001072332 Monia Species 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JHVLLYQQQYIWKX-UHFFFAOYSA-N benzyl 2-bromoacetate Chemical compound BrCC(=O)OCC1=CC=CC=C1 JHVLLYQQQYIWKX-UHFFFAOYSA-N 0.000 description 1
- IZZIPPQWYVRGRS-UHFFFAOYSA-N benzyl 2-bromopropanoate Chemical compound CC(Br)C(=O)OCC1=CC=CC=C1 IZZIPPQWYVRGRS-UHFFFAOYSA-N 0.000 description 1
- JZYXQRUIIAOBOQ-UHFFFAOYSA-N benzyl 2-chloropropanoate Chemical compound CC(Cl)C(=O)OCC1=CC=CC=C1 JZYXQRUIIAOBOQ-UHFFFAOYSA-N 0.000 description 1
- OOQHRQQUQCZZHF-UHFFFAOYSA-N benzyl 3-chloropropanoate Chemical compound ClCCC(=O)OCC1=CC=CC=C1 OOQHRQQUQCZZHF-UHFFFAOYSA-N 0.000 description 1
- XCTMSCBHFJLFCT-UHFFFAOYSA-N benzyltin Chemical compound [Sn]CC1=CC=CC=C1 XCTMSCBHFJLFCT-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- NFBPZHAGQGTTOS-UHFFFAOYSA-N bis(ethenyl)-sulfanylidenetin Chemical compound C(=C)[Sn](C=C)=S NFBPZHAGQGTTOS-UHFFFAOYSA-N 0.000 description 1
- NMEGSGKCIWQRDB-UHFFFAOYSA-N butyl 2-bromoacetate Chemical compound CCCCOC(=O)CBr NMEGSGKCIWQRDB-UHFFFAOYSA-N 0.000 description 1
- INMAEXGIVZJYIJ-UHFFFAOYSA-N butyl 2-bromopropanoate Chemical compound CCCCOC(=O)C(C)Br INMAEXGIVZJYIJ-UHFFFAOYSA-N 0.000 description 1
- KRZKQEQBZXWCDJ-UHFFFAOYSA-N butyl 3-chloropropanoate Chemical compound CCCCOC(=O)CCCl KRZKQEQBZXWCDJ-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JUYWETIJJLDVBC-UHFFFAOYSA-N butyl-methyl-sulfanylidenetin Chemical compound CCCC[Sn](C)=S JUYWETIJJLDVBC-UHFFFAOYSA-N 0.000 description 1
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- SZOPAPBTRRMGMD-UHFFFAOYSA-N chloroethene;1,1,2-trichloroethene Chemical group ClC=C.ClC=C(Cl)Cl SZOPAPBTRRMGMD-UHFFFAOYSA-N 0.000 description 1
- DHZSIQDUYCWNSB-UHFFFAOYSA-N chloroethene;1,1-dichloroethene Chemical compound ClC=C.ClC(Cl)=C DHZSIQDUYCWNSB-UHFFFAOYSA-N 0.000 description 1
- BMZQPXKCLRADET-UHFFFAOYSA-N chloroethene;2-ethylhexyl prop-2-enoate Chemical compound ClC=C.CCCCC(CC)COC(=O)C=C BMZQPXKCLRADET-UHFFFAOYSA-N 0.000 description 1
- HLRNWZLPRFTCIO-IPZCTEOASA-N chloroethene;diethyl (e)-but-2-enedioate Chemical compound ClC=C.CCOC(=O)\C=C\C(=O)OCC HLRNWZLPRFTCIO-IPZCTEOASA-N 0.000 description 1
- OHRNNGVUQOZQNK-UHFFFAOYSA-N cyclohexyl 2-chloropropanoate Chemical compound CC(Cl)C(=O)OC1CCCCC1 OHRNNGVUQOZQNK-UHFFFAOYSA-N 0.000 description 1
- JFGPTUXMBWCYKV-UHFFFAOYSA-N cyclohexyl 3-bromopropanoate Chemical compound BrCCC(=O)OC1CCCCC1 JFGPTUXMBWCYKV-UHFFFAOYSA-N 0.000 description 1
- GPKFWQIRHJGZKV-UHFFFAOYSA-N cyclohexyl 3-chloropropanoate Chemical compound ClCCC(=O)OC1CCCCC1 GPKFWQIRHJGZKV-UHFFFAOYSA-N 0.000 description 1
- FTYGBOMHIFFZNC-UHFFFAOYSA-N cyclopentyl 2-chloroacetate Chemical compound ClCC(=O)OC1CCCC1 FTYGBOMHIFFZNC-UHFFFAOYSA-N 0.000 description 1
- OMRFZIDOMSMRSP-UHFFFAOYSA-N decyl 2-bromoacetate Chemical compound CCCCCCCCCCOC(=O)CBr OMRFZIDOMSMRSP-UHFFFAOYSA-N 0.000 description 1
- KZCNWHKYIZKOFU-UHFFFAOYSA-N decyl 3-bromopropanoate Chemical compound CCCCCCCCCCOC(=O)CCBr KZCNWHKYIZKOFU-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- OAHCTWDXJQEECF-UHFFFAOYSA-N dicyclohexyl(sulfanylidene)tin Chemical compound C1CCCCC1[Sn](=S)C1CCCCC1 OAHCTWDXJQEECF-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- LAXMHCDABZOPQT-UHFFFAOYSA-N diethyl(sulfanylidene)tin Chemical compound CC[Sn](=S)CC LAXMHCDABZOPQT-UHFFFAOYSA-N 0.000 description 1
- HRFMZHBXTDWTJD-UHFFFAOYSA-N dihexyltin Chemical compound CCCCCC[Sn]CCCCCC HRFMZHBXTDWTJD-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- CYXRBVIJBDYNQU-UHFFFAOYSA-N diphenyl(sulfanylidene)tin Chemical compound C=1C=CC=CC=1[Sn](=S)C1=CC=CC=C1 CYXRBVIJBDYNQU-UHFFFAOYSA-N 0.000 description 1
- CXSQZHYAZWXVNI-UHFFFAOYSA-N dipropyl(sulfanylidene)tin Chemical compound CCC[Sn](=S)CCC CXSQZHYAZWXVNI-UHFFFAOYSA-N 0.000 description 1
- QIPFGFYXERNTNP-UHFFFAOYSA-N dodecyl 2-bromoacetate Chemical compound CCCCCCCCCCCCOC(=O)CBr QIPFGFYXERNTNP-UHFFFAOYSA-N 0.000 description 1
- JPPYCWJDINILKY-UHFFFAOYSA-N dodecyl 2-chloroacetate Chemical compound CCCCCCCCCCCCOC(=O)CCl JPPYCWJDINILKY-UHFFFAOYSA-N 0.000 description 1
- ZWBOULTZYRWSPZ-UHFFFAOYSA-N dodecyl 2-chloropropanoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)Cl ZWBOULTZYRWSPZ-UHFFFAOYSA-N 0.000 description 1
- HTOMOEJIHHORQT-UHFFFAOYSA-N dodecyl(sulfanylidene)tin Chemical compound CCCCCCCCCCCC[Sn]=S HTOMOEJIHHORQT-UHFFFAOYSA-N 0.000 description 1
- VDEKURXOWJYWCG-UHFFFAOYSA-N dodecyltin Chemical compound CCCCCCCCCCCC[Sn] VDEKURXOWJYWCG-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 1
- DFEHSFZILGOAJK-UHFFFAOYSA-N ethenyl 2-bromoacetate Chemical compound BrCC(=O)OC=C DFEHSFZILGOAJK-UHFFFAOYSA-N 0.000 description 1
- XJELOQYISYPGDX-UHFFFAOYSA-N ethenyl 2-chloroacetate Chemical compound ClCC(=O)OC=C XJELOQYISYPGDX-UHFFFAOYSA-N 0.000 description 1
- BTOIAAYVFNXNPA-UHFFFAOYSA-N ethenyl 2-chloropropanoate Chemical compound CC(Cl)C(=O)OC=C BTOIAAYVFNXNPA-UHFFFAOYSA-N 0.000 description 1
- XLTLBMFCWKSJSD-UHFFFAOYSA-N ethenyl 3-bromopropanoate Chemical compound BrCCC(=O)OC=C XLTLBMFCWKSJSD-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- FQTIYMRSUOADDK-UHFFFAOYSA-N ethyl 3-bromopropanoate Chemical compound CCOC(=O)CCBr FQTIYMRSUOADDK-UHFFFAOYSA-N 0.000 description 1
- ZCLGVXACCAZJOX-UHFFFAOYSA-N ethyl 3-chloropropanoate Chemical compound CCOC(=O)CCCl ZCLGVXACCAZJOX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GWPSCSIMTIVYIH-UHFFFAOYSA-N ethyl(sulfanylidene)tin Chemical compound CC[Sn]=S GWPSCSIMTIVYIH-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- BTHNTCJTOYZMCB-UHFFFAOYSA-N hexadecyl 2-bromoacetate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CBr BTHNTCJTOYZMCB-UHFFFAOYSA-N 0.000 description 1
- XQHTWCIWGQDGOI-UHFFFAOYSA-N hexadecyl 2-chloroacetate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCl XQHTWCIWGQDGOI-UHFFFAOYSA-N 0.000 description 1
- UHVQFSUSOVXCEO-UHFFFAOYSA-N hexadecyl 2-chloropropanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(C)Cl UHVQFSUSOVXCEO-UHFFFAOYSA-N 0.000 description 1
- HKMCSNOMIKTPRU-UHFFFAOYSA-N hexadecyl 3-chloropropanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCl HKMCSNOMIKTPRU-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- NNPJKFMGVZNJHG-UHFFFAOYSA-N hexyl 2-bromoacetate Chemical compound CCCCCCOC(=O)CBr NNPJKFMGVZNJHG-UHFFFAOYSA-N 0.000 description 1
- PYOAHWWMEFRKLM-UHFFFAOYSA-N hexyl 3-chloropropanoate Chemical compound CCCCCCOC(=O)CCCl PYOAHWWMEFRKLM-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
- AWJZTPWDQYFQPQ-UHFFFAOYSA-N methyl 2-chloroprop-2-enoate Chemical compound COC(=O)C(Cl)=C AWJZTPWDQYFQPQ-UHFFFAOYSA-N 0.000 description 1
- JLEJCNOTNLZCHQ-UHFFFAOYSA-N methyl 2-chloropropanoate Chemical compound COC(=O)C(C)Cl JLEJCNOTNLZCHQ-UHFFFAOYSA-N 0.000 description 1
- KQEVIFKPZOGBMZ-UHFFFAOYSA-N methyl 3-bromopropanoate Chemical compound COC(=O)CCBr KQEVIFKPZOGBMZ-UHFFFAOYSA-N 0.000 description 1
- GZGJIACHBCQSPC-UHFFFAOYSA-N methyl 3-chloropropanoate Chemical compound COC(=O)CCCl GZGJIACHBCQSPC-UHFFFAOYSA-N 0.000 description 1
- IJWZBPYUPFWBMY-UHFFFAOYSA-N methyl-phenyl-sulfanylidenetin Chemical compound C[Sn](=S)C1=CC=CC=C1 IJWZBPYUPFWBMY-UHFFFAOYSA-N 0.000 description 1
- 229940102838 methylmethacrylate Drugs 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- ROZPNEGZBIUWBX-UHFFFAOYSA-N n-[bis(diethylamino)phosphoryl]-n-ethylethanamine Chemical compound CCN(CC)P(=O)(N(CC)CC)N(CC)CC ROZPNEGZBIUWBX-UHFFFAOYSA-N 0.000 description 1
- CTAPFXJABKRLIA-UHFFFAOYSA-N nonyl 2-bromoacetate Chemical compound CCCCCCCCCOC(=O)CBr CTAPFXJABKRLIA-UHFFFAOYSA-N 0.000 description 1
- LOBRVJLEFHWKDI-UHFFFAOYSA-N octadecyl 2-bromoacetate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CBr LOBRVJLEFHWKDI-UHFFFAOYSA-N 0.000 description 1
- 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
- AYOLAXLMNGHJRT-UHFFFAOYSA-N octadecyltin Chemical compound CCCCCCCCCCCCCCCCCC[Sn] AYOLAXLMNGHJRT-UHFFFAOYSA-N 0.000 description 1
- ZBNUZMDEFBLZIJ-UHFFFAOYSA-N octyl 2-bromoacetate Chemical compound CCCCCCCCOC(=O)CBr ZBNUZMDEFBLZIJ-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
- NNXMXUSTTDFBDE-UHFFFAOYSA-N octyl 2-chloroacetate Chemical compound CCCCCCCCOC(=O)CCl NNXMXUSTTDFBDE-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
- 229940049964 oleate Drugs 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012071 phase Substances 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- MUWVIMJPXKIXJK-UHFFFAOYSA-N prop-2-enyl 2-bromoacetate Chemical compound BrCC(=O)OCC=C MUWVIMJPXKIXJK-UHFFFAOYSA-N 0.000 description 1
- VMBJJCDVORDOCF-UHFFFAOYSA-N prop-2-enyl 2-chloroacetate Chemical compound ClCC(=O)OCC=C VMBJJCDVORDOCF-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
- 239000000376 reactant Substances 0.000 description 1
- 230000036647 reaction Effects 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
- 238000001228 spectrum Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- KUZUNHDCZIJWAO-UHFFFAOYSA-N tetradecyl 3-chloropropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCl KUZUNHDCZIJWAO-UHFFFAOYSA-N 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-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
- LYRCQNDYYRPFMF-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C LYRCQNDYYRPFMF-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
- 238000009827 uniform distribution Methods 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229940117958 vinyl acetate Drugs 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
- 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
- 230000003245 working effect Effects 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 |
|---|---|
| CA1052804A true CA1052804A (en) | 1979-04-17 |
Family
ID=27035694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA215,250A Expired CA1052804A (en) | 1974-03-08 | 1974-12-04 | Organotin mercaptide process |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS50121232A (zh) |
| AT (1) | AT336635B (zh) |
| BR (1) | BR7501284A (zh) |
| CA (1) | CA1052804A (zh) |
| CH (1) | CH619961A5 (zh) |
| DE (3) | DE2559531C3 (zh) |
| ES (1) | ES433740A1 (zh) |
| FR (1) | FR2263248B1 (zh) |
| GB (1) | GB1443684A (zh) |
| IN (1) | IN142694B (zh) |
| IT (1) | IT1026869B (zh) |
| NL (1) | NL7501031A (zh) |
| PH (1) | PH13175A (zh) |
| SE (3) | SE7502024L (zh) |
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/en 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 DE2559531A patent/DE2559531C3/de not_active Expired
- 1975-01-29 DE DE2503554A patent/DE2503554C3/de not_active Expired
- 1975-01-29 NL NL7501031A patent/NL7501031A/xx not_active Application Discontinuation
- 1975-01-29 DE DE2559446A patent/DE2559446C3/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 SE7805089A patent/SE7805089L/xx unknown
- 1978-05-03 SE SE7805103A patent/SE7805103L/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE7805103L (sv) | 1978-05-03 |
| DE2559446A1 (de) | 1976-12-09 |
| CH619961A5 (en) | 1980-10-31 |
| BR7501284A (pt) | 1975-12-02 |
| DE2559446C3 (de) | 1979-08-09 |
| DE2559446B2 (de) | 1978-11-16 |
| DE2559531A1 (de) | 1977-03-03 |
| JPS50121232A (zh) | 1975-09-23 |
| FR2263248A1 (zh) | 1975-10-03 |
| DE2503554C3 (de) | 1978-03-30 |
| DE2559531C3 (de) | 1982-03-04 |
| FR2263248B1 (zh) | 1978-12-29 |
| GB1443684A (en) | 1976-07-21 |
| AT336635B (de) | 1977-05-10 |
| ATA111775A (de) | 1976-09-15 |
| SE7805089L (sv) | 1978-05-03 |
| PH13175A (en) | 1980-01-08 |
| DE2503554A1 (de) | 1975-09-11 |
| IT1026869B (it) | 1978-10-20 |
| SE7502024L (zh) | 1975-09-09 |
| NL7501031A (nl) | 1975-09-10 |
| ES433740A1 (es) | 1977-02-16 |
| AU7739075A (en) | 1976-07-22 |
| IN142694B (zh) | 1977-08-13 |
| DE2503554B2 (de) | 1977-08-18 |
| DE2559531B2 (de) | 1980-05-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1055957A (en) | Sulfide containing tin stabilizers | |
| CA1126748A (en) | Organotin mercaptoalkanol esters and alkoxides containing sulfide groups | |
| CA2061821C (en) | Liquid organotinthioalkanol stabilizer compositions and vinyl halide resin compositions containing the same | |
| CA1052804A (en) | Organotin mercaptide process | |
| US3970678A (en) | Organotin mercaptide process | |
| US3115509A (en) | Chemical product and process | |
| US4104292A (en) | Method for preparing organotin compounds | |
| US3248411A (en) | Process for the conversion of highly alkylated tin compounds into lower alkylated tin halides | |
| DE1158069B (de) | Verfahren zur Herstellung von Silarylensilanolen und -siloxanen | |
| US3890277A (en) | Alkyltin polysulfide thioester stabilized composition | |
| CA1049545A (en) | Alkyltin polysulfide thioesters | |
| US3454610A (en) | Synthesis of organometallic halides by redistribution | |
| US2873287A (en) | Process for preparing vinyltin compounds | |
| US3665025A (en) | Organo(halo) disulfur tin derivatives and the process of preparing the same | |
| US3846459A (en) | Organotin mercaptocarboxylates | |
| JPS6017218B2 (ja) | ハロゲン化ビニル樹脂組成物用の安定剤系 | |
| US3387012A (en) | Production of dialiphatic tind dihalides | |
| US3069447A (en) | Organo-tin compounds and their preparation | |
| US2700675A (en) | Method of preparing monomeric organotin dialkoxides | |
| US3933680A (en) | Stabilizing compositions for polyvinylchloride | |
| US3758536A (en) | Process for preparing polymeric halo tin thiohydrocarbyl carboxylates | |
| US3607891A (en) | Process for preparing tricyclohexyltin halides | |
| US3772244A (en) | Bis(organotin)stabilizers for vinyl chloride polymers | |
| US4202830A (en) | Organotin halides | |
| US3507893A (en) | Process for preparing organotin mercaptides |