GB781905A - Improvements in the production of organic tin compounds - Google Patents
Improvements in the production of organic tin compoundsInfo
- Publication number
- GB781905A GB781905A GB35357/54A GB3535754A GB781905A GB 781905 A GB781905 A GB 781905A GB 35357/54 A GB35357/54 A GB 35357/54A GB 3535754 A GB3535754 A GB 3535754A GB 781905 A GB781905 A GB 781905A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- mercapto
- alcohol
- compounds
- residue
- 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
- 150000003606 tin compounds Chemical class 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 12
- 150000001875 compounds Chemical class 0.000 abstract 12
- -1 organo tin compounds Chemical class 0.000 abstract 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 7
- 125000003396 thiol group Chemical group [H]S* 0.000 abstract 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 5
- 229920006395 saturated elastomer Polymers 0.000 abstract 5
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229940049964 oleate Drugs 0.000 abstract 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 abstract 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- HPFVPXZIJUQEHT-UHFFFAOYSA-M dibutyltin(1+);dodecane-1-thiolate Chemical compound CCCC[Sn+]CCCC.CCCCCCCCCCCC[S-] HPFVPXZIJUQEHT-UHFFFAOYSA-M 0.000 abstract 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 abstract 1
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 abstract 1
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 abstract 1
- PCPYTNCQOSFKGG-UHFFFAOYSA-N 1-chlorobuta-1,3-diene Chemical compound ClC=CC=C PCPYTNCQOSFKGG-UHFFFAOYSA-N 0.000 abstract 1
- WZRCUJWDESFXFX-UHFFFAOYSA-N 2,3-dichlorobutane-1,4-dithiol Chemical compound SCC(Cl)C(Cl)CS WZRCUJWDESFXFX-UHFFFAOYSA-N 0.000 abstract 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 abstract 1
- JNODDICFTDYODH-UHFFFAOYSA-N 2-hydroxytetrahydrofuran Chemical compound OC1CCCO1 JNODDICFTDYODH-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- FWBDGLGQHIFQQG-UHFFFAOYSA-M C(C=C/C(=O)O)(=O)OC.C(CCCCCCCCCCC)[Sn](CCCC)(CCCC)S Chemical compound C(C=C/C(=O)O)(=O)OC.C(CCCCCCCCCCC)[Sn](CCCC)(CCCC)S FWBDGLGQHIFQQG-UHFFFAOYSA-M 0.000 abstract 1
- BLXBLQPGZOUYKL-UHFFFAOYSA-L C(C=C/C(=O)[O-])(=O)OC.C(CCCCCCCCCCC)S[Sn+](CCCC)CCCC Chemical compound C(C=C/C(=O)[O-])(=O)OC.C(CCCCCCCCCCC)S[Sn+](CCCC)CCCC BLXBLQPGZOUYKL-UHFFFAOYSA-L 0.000 abstract 1
- NRMBGXXXCHBJMA-UHFFFAOYSA-M C(CCCCCCCCCCC)(=O)O.C(CCCCCCCCCCC)[Sn](CCCC)(CCCC)S Chemical compound C(CCCCCCCCCCC)(=O)O.C(CCCCCCCCCCC)[Sn](CCCC)(CCCC)S NRMBGXXXCHBJMA-UHFFFAOYSA-M 0.000 abstract 1
- WVDYBOADDMMFIY-UHFFFAOYSA-N Cyclopentanethiol Chemical class SC1CCCC1 WVDYBOADDMMFIY-UHFFFAOYSA-N 0.000 abstract 1
- 239000005639 Lauric acid Substances 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 230000032683 aging Effects 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001339 alkali metal compounds Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- SMTOKHQOVJRXLK-UHFFFAOYSA-N butane-1,4-dithiol Chemical compound SCCCCS SMTOKHQOVJRXLK-UHFFFAOYSA-N 0.000 abstract 1
- BPOPGHPHBCLJOK-UHFFFAOYSA-N butanedithioic acid Chemical compound CCCC(S)=S BPOPGHPHBCLJOK-UHFFFAOYSA-N 0.000 abstract 1
- DGAODIKUWGRDBO-UHFFFAOYSA-N butanethioic s-acid Chemical compound CCCC(O)=S DGAODIKUWGRDBO-UHFFFAOYSA-N 0.000 abstract 1
- SQMPYEMNVGAWNJ-UHFFFAOYSA-L butyl-dichloro-ethylstannane Chemical compound C(C)[Sn](CCCC)(Cl)Cl SQMPYEMNVGAWNJ-UHFFFAOYSA-L 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003610 charcoal Substances 0.000 abstract 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 abstract 1
- LGNFUMOLHPFGBW-UHFFFAOYSA-M dibutyl(dodecyl)stannanylium sulfanide Chemical compound C(CCC)[Sn](S)(CCCCCCCCCCCC)CCCC LGNFUMOLHPFGBW-UHFFFAOYSA-M 0.000 abstract 1
- YRKILJAUUWNCOC-UHFFFAOYSA-L dibutyl(dodecylsulfanyl)stannanylium;dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCS[Sn+](CCCC)CCCC YRKILJAUUWNCOC-UHFFFAOYSA-L 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 abstract 1
- ICTIVTCHZRVVQR-UHFFFAOYSA-N hexanebis(thioic s-acid) Chemical compound SC(=O)CCCCC(S)=O ICTIVTCHZRVVQR-UHFFFAOYSA-N 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 abstract 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 abstract 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- WRIQZMMFAMFZSM-UHFFFAOYSA-N prop-2-enethioic s-acid Chemical compound SC(=O)C=C WRIQZMMFAMFZSM-UHFFFAOYSA-N 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 abstract 1
- IJANHNQMUKHUKW-UHFFFAOYSA-N propanebis(thioic s-acid) Chemical compound SC(=O)CC(S)=O IJANHNQMUKHUKW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000005060 rubber Substances 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 229920003051 synthetic elastomer Polymers 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- 239000005061 synthetic rubber Substances 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C08K5/57—Organo-tin compounds
- C08K5/58—Organo-tin compounds containing sulfur
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Synthetic resins (e.g. halogen-containing polyvinyl compounds and their copolymers) and halogenated synthetic rubbers (e.g. from condensed chlorbutadiene) may be stabilized against ageing by addition of an organotin compound of formula <FORM:0781905/IV (a)/1> where X1 and X2 are alkyl groups, Y is the residue of an alcohol or a carboxylic acid and Z is the residue of a saturated or unsaturated aliphatic or cycloaliphatic compound containing one or more mercapto groups. Compounds specified include dodecyl mercapto dibutyl tin laurate, dodecyl mercapto dibutyl tin oleate, dodecyl mercapto dibutyl tin methyl maleate: <FORM:0781905/IV (a)/2> and many others.ALSO:The invention comprises organo tin compounds of formula <FORM:0781905/IV (a)/1> where X1 and X2 are identical or different alkyl groups, Y is the residue of an alcohol or carboxylic acid and Z is the residue of a saturated or unsaturated aliphatic or cycloaliphatic compound containing one or more mercapto groups. They may be prepared by reacting a dialkyl tin dihalide of formula X1X2SnHal2 simultaneously or in any sequence with such amounts of an alkali metal compound of an alcohol or carboxylic acid and a saturated or unsaturated aliphatic or cycloaliphatic compound containing one or more mercapto groups that the resultant product contains equivalent amounts of the alcohol or carboxylic acid and the mercapto compound. Specified dialkyl tin dihalides include dimethyl, diethyl, dipropyl, dibutyl, diamyl, dihexyl, dioctyl, diallyl, methylethyl, methylbutyl, ethylbutyl tin dichloride, dibromide and di-iodide. Suitable alcohols specified include methanol, ethanol, propanol, butanol, hexanol, octanol, ethylhexanol, dodecanol, allyl alcohol, cyclohexanol, benzyl alcohol, tetrahydrofuryl alcohol and the ether or thioether alcohols derived therefrom. Acetic, propionic, butyric, valeric, caproic, ethylhexanoic, pelargonic, palmitic, acrylic, crotonic, linoleic, lauric, oleic, ricinoleic, benzoic, cinamic, and phenylacetic acids are specified as carboxylic acids. There may also be used the half esters of dicarboxylic acids, e.g. maleic, succinic, adipic and phthalic acid. Compounds containing mercapto groups (used as their metal, especially alkali-metal derivatives) include methyl, ethyl, propyl, n-butyl, iso-butyl, ethylhexyl, octyl, decyl, dodecyl, octadecyl, allyl, cyclohexyl, methylcyclohexyl and cyclopentyl thiols. The hydrocarbon chains or rings may be interrupted by oxygen or sulphur atoms, sulphoxy, sulphonyl or imido groups or also contain carbonyl or epoxidic oxygen, e.g. mercapto dibutyl ether, 4,41-dimercapto dibutyl ether, and the corresponding thioethers. These compounds may also contain halogen or further mercapto groups, e.g. 1,2-dimercapto ethane, 1,3-dimercaptopropane, 1,4-dimercaptobutane, 1,4-dimercapto-2,3-dichlorbutane. Saturated or unsaturated monobasic or dibasic thiolic acids, e.g. acetothiolic acid, dithioacetic and, thiobutyric acid, dithiobutyric acid, dithiomalonic acid, dithioadipic acid, thioacrylic acid and thiocrotonic acid may also be used. The reaction may be carried out between - 10 DEG C. and 150 DEG C., preferably in inert solvents such as benzene, toluene or xylene. The alcoholic starting material may be used in excess as diluent. In an example dodecyl mercaptan dissolved in benzene is added to a solution of sodium methylate in methanol. To the mixture lauric acid in benzene is added, and the whole stirred for half an hour. Dibutyl tin dichloride in benzene is then added and the mixture refluxed. Sodium chloride precipitates on cooling and is filtered off. The solvent is distilled from the filtrate under reduced pressure and the tin compound purified by solution in toluene, addition of animal charcoal, filtration and removal of the toluene. Among other compounds prepared are dodecylmercapto dibutyl tin oleate and dodecylmercapto dibutyl tin methyl maleate: <FORM:0781905/IV (a)/2> Specifications 692,556, 719,733 and 781,906, [Group IV (a)], are referred to.ALSO:Organotin compounds of formula: <FORM:0781905/V/1> where X1 and X2 are alkyl groups, Y is the residue of an alcohol or a carboxylic acid and Z is the residue of a saturated or unsaturated aliphatic or cycloaliphatic compound containing one or more mercapto groups may be used as rubber antioxidants. Compounds specified include dodecylmercapto dibutyltin laurate, dodecylmercapto dibutyl tin oleate, dodecylmercapto dibutylt in methyl maleate: <FORM:0781905/V/2> and many others.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE781905X | 1954-07-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB781905A true GB781905A (en) | 1957-08-28 |
Family
ID=6692701
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB35357/54A Expired GB781905A (en) | 1954-07-17 | 1954-12-07 | Improvements in the production of organic tin compounds |
Country Status (2)
Country | Link |
---|---|
GB (1) | GB781905A (en) |
NL (1) | NL95061C (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3029267A (en) * | 1958-01-21 | 1962-04-10 | Thiokol Chemical Corp | Dibutyltin dithioacylates |
US3088956A (en) * | 1961-03-20 | 1963-05-07 | Union Carbide Corp | Acyloxymetallosulfophthalates |
-
1954
- 1954-11-30 NL NL192799A patent/NL95061C/xx active
- 1954-12-07 GB GB35357/54A patent/GB781905A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3029267A (en) * | 1958-01-21 | 1962-04-10 | Thiokol Chemical Corp | Dibutyltin dithioacylates |
US3088956A (en) * | 1961-03-20 | 1963-05-07 | Union Carbide Corp | Acyloxymetallosulfophthalates |
Also Published As
Publication number | Publication date |
---|---|
NL95061C (en) | 1960-08-15 |
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