DE2218211C2 - Verfahren zur Herstellung von asymmetrischen Triorganozinnhalogeniden - Google Patents
Verfahren zur Herstellung von asymmetrischen TriorganozinnhalogenidenInfo
- Publication number
- DE2218211C2 DE2218211C2 DE19722218211 DE2218211A DE2218211C2 DE 2218211 C2 DE2218211 C2 DE 2218211C2 DE 19722218211 DE19722218211 DE 19722218211 DE 2218211 A DE2218211 A DE 2218211A DE 2218211 C2 DE2218211 C2 DE 2218211C2
- Authority
- DE
- Germany
- Prior art keywords
- chloride
- solution
- tin
- pentane
- product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000004820 halides Chemical class 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000000460 chlorine Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 239000006227 byproduct Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910008433 SnCU Inorganic materials 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 16
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 150000004795 grignard reagents Chemical class 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 239000007818 Grignard reagent Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- -1 tin (IV) halide Chemical class 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 125000000962 organic group Chemical group 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WMJMABVHDMRMJA-UHFFFAOYSA-M [Cl-].[Mg+]C1CCCCC1 Chemical compound [Cl-].[Mg+]C1CCCCC1 WMJMABVHDMRMJA-UHFFFAOYSA-M 0.000 description 3
- ZFYPNTXTIAXFDS-UHFFFAOYSA-M chloro-cyclohexyl-dimethylstannane Chemical compound C[Sn](C)(Cl)C1CCCCC1 ZFYPNTXTIAXFDS-UHFFFAOYSA-M 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- YTUOPHMUDGXBFN-UHFFFAOYSA-M butyl-chloro-dimethylstannane Chemical compound CCCC[Sn](C)(C)Cl YTUOPHMUDGXBFN-UHFFFAOYSA-M 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- SXLXYDPVHCAULH-UHFFFAOYSA-M dibutyl(cyclohexyl)stannanylium;chloride Chemical compound CCCC[Sn](Cl)(CCCC)C1CCCCC1 SXLXYDPVHCAULH-UHFFFAOYSA-M 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- HQDAZWQQKSJCTM-UHFFFAOYSA-M magnesium;octane;chloride Chemical compound [Mg+2].[Cl-].CCCCCCC[CH2-] HQDAZWQQKSJCTM-UHFFFAOYSA-M 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 2
- UHUMQRAGTZNULC-UHFFFAOYSA-N octyl(tripropyl)stannane Chemical compound CCCCCCCC[Sn](CCC)(CCC)CCC UHUMQRAGTZNULC-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N Methylcyclohexane Natural products CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229940095564 anhydrous calcium sulfate Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- ISGCVUHZDITLMD-UHFFFAOYSA-N butyl(trimethyl)stannane Chemical compound CCCC[Sn](C)(C)C ISGCVUHZDITLMD-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- FVFLIQMADUVDSP-UHFFFAOYSA-M chloro(tripropyl)stannane Chemical compound CCC[Sn](Cl)(CCC)CCC FVFLIQMADUVDSP-UHFFFAOYSA-M 0.000 description 1
- PAQPGBHOOPWVDJ-UHFFFAOYSA-M chloro-cyclohexyl-dipropylstannane Chemical compound CCC[Sn](Cl)(CCC)C1CCCCC1 PAQPGBHOOPWVDJ-UHFFFAOYSA-M 0.000 description 1
- WQFHNEQTOKSESB-UHFFFAOYSA-M chloro-dicyclohexyl-methylstannane Chemical compound C[Sn](C1CCCCC1)(C1CCCCC1)Cl WQFHNEQTOKSESB-UHFFFAOYSA-M 0.000 description 1
- VTBLJXCIHGQANZ-UHFFFAOYSA-M chloro-dimethyl-octylstannane Chemical compound CCCCCCCC[Sn](C)(C)Cl VTBLJXCIHGQANZ-UHFFFAOYSA-M 0.000 description 1
- HIYNUHJUUDOWAP-UHFFFAOYSA-M chloro-methyl-dioctylstannane Chemical compound C[Sn](CCCCCCCC)(CCCCCCCC)Cl HIYNUHJUUDOWAP-UHFFFAOYSA-M 0.000 description 1
- YCXXIKKCDAQPEA-UHFFFAOYSA-M chloro-octyl-dipropylstannane Chemical compound CCCCCCCC[Sn](Cl)(CCC)CCC YCXXIKKCDAQPEA-UHFFFAOYSA-M 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- FEWVPXQAXJQHKL-UHFFFAOYSA-N cyclohexyl(trimethyl)stannane Chemical compound C[Sn](C)(C)C1CCCCC1 FEWVPXQAXJQHKL-UHFFFAOYSA-N 0.000 description 1
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 1
- ZKYMKDMFYHHSOG-UHFFFAOYSA-N dibutyl(dicyclohexyl)stannane Chemical compound C1CCCCC1[Sn](CCCC)(CCCC)C1CCCCC1 ZKYMKDMFYHHSOG-UHFFFAOYSA-N 0.000 description 1
- LSTLNNOJHFUVLF-UHFFFAOYSA-N dibutyl(dimethyl)stannane Chemical compound CCCC[Sn](C)(C)CCCC LSTLNNOJHFUVLF-UHFFFAOYSA-N 0.000 description 1
- JZJOCMWUGCDJEZ-UHFFFAOYSA-N dicyclohexyl(dihexyl)stannane Chemical compound C1CCCCC1[Sn](CCCCCC)(CCCCCC)C1CCCCC1 JZJOCMWUGCDJEZ-UHFFFAOYSA-N 0.000 description 1
- PZHCWZLMGTUERE-UHFFFAOYSA-N dicyclohexyl(dipropyl)stannane Chemical compound C1CCCCC1[Sn](CCC)(CCC)C1CCCCC1 PZHCWZLMGTUERE-UHFFFAOYSA-N 0.000 description 1
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 1
- SBOSGIJGEHWBKV-UHFFFAOYSA-L dioctyltin(2+);dichloride Chemical compound CCCCCCCC[Sn](Cl)(Cl)CCCCCCCC SBOSGIJGEHWBKV-UHFFFAOYSA-L 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- PODWXQQNRWNDGD-UHFFFAOYSA-L sodium thiosulfate pentahydrate Chemical compound O.O.O.O.O.[Na+].[Na+].[O-]S([S-])(=O)=O PODWXQQNRWNDGD-UHFFFAOYSA-L 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
- RBAZHXLAXQMWPM-UHFFFAOYSA-N tributyl(cyclohexyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1CCCCC1 RBAZHXLAXQMWPM-UHFFFAOYSA-N 0.000 description 1
- LWHNFNZUCSZFGX-UHFFFAOYSA-K trichloro(4,4-dicyclohexylbutyl)stannane Chemical compound C1CCCCC1C(CCC[Sn](Cl)(Cl)Cl)C1CCCCC1 LWHNFNZUCSZFGX-UHFFFAOYSA-K 0.000 description 1
- YFRLQYJXUZRYDN-UHFFFAOYSA-K trichloro(methyl)stannane Chemical compound C[Sn](Cl)(Cl)Cl YFRLQYJXUZRYDN-UHFFFAOYSA-K 0.000 description 1
- VWZWXVXARBLHQI-UHFFFAOYSA-N trimethyl(octyl)stannane Chemical compound CCCCCCCC[Sn](C)(C)C VWZWXVXARBLHQI-UHFFFAOYSA-N 0.000 description 1
- 238000007514 turning 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
-
- 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13404571A | 1971-04-14 | 1971-04-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2218211A1 DE2218211A1 (de) | 1972-11-09 |
| DE2218211C2 true DE2218211C2 (de) | 1982-09-16 |
Family
ID=22461508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722218211 Expired DE2218211C2 (de) | 1971-04-14 | 1972-04-14 | Verfahren zur Herstellung von asymmetrischen Triorganozinnhalogeniden |
Country Status (12)
| Country | Link |
|---|---|
| AT (2) | AT313917B (no) |
| BE (1) | BE782029A (no) |
| CA (1) | CA966145A (no) |
| CH (1) | CH579093A5 (no) |
| DE (1) | DE2218211C2 (no) |
| DK (1) | DK133108C (no) |
| ES (1) | ES401712A1 (no) |
| GB (1) | GB1340167A (no) |
| IT (1) | IT954235B (no) |
| NL (1) | NL177830C (no) |
| NO (1) | NO136098C (no) |
| SE (1) | SE383349B (no) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3475473A (en) * | 1966-10-11 | 1969-10-28 | Nitto Kasei Co Ltd | Process for preparing triorganotin halides and bis(triorganotin) oxides |
| US3471539A (en) * | 1967-08-23 | 1969-10-07 | Nitto Kasei Co Ltd | Method for preparing triorganotin halides and bis(triorganotin) oxides |
| US3475472A (en) * | 1967-09-21 | 1969-10-28 | Nitto Kasei Co Ltd | Method for preparing triorganotin halides and bis(triorganotin) oxides |
| GB1232691A (no) * | 1968-04-25 | 1971-05-19 |
-
1972
- 1972-04-07 NL NL7204713A patent/NL177830C/xx not_active IP Right Cessation
- 1972-04-10 NO NO121272A patent/NO136098C/no unknown
- 1972-04-12 SE SE471572A patent/SE383349B/xx unknown
- 1972-04-12 GB GB1689472A patent/GB1340167A/en not_active Expired
- 1972-04-13 ES ES401712A patent/ES401712A1/es not_active Expired
- 1972-04-13 DK DK180872A patent/DK133108C/da not_active IP Right Cessation
- 1972-04-13 BE BE782029A patent/BE782029A/xx not_active IP Right Cessation
- 1972-04-13 CA CA139,595A patent/CA966145A/en not_active Expired
- 1972-04-13 IT IT943872A patent/IT954235B/it active
- 1972-04-14 AT AT331672A patent/AT313917B/de not_active IP Right Cessation
- 1972-04-14 DE DE19722218211 patent/DE2218211C2/de not_active Expired
- 1972-04-14 AT AT64973A patent/AT319663B/de not_active IP Right Cessation
- 1972-04-14 CH CH551872A patent/CH579093A5/xx not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| ES401712A1 (es) | 1975-03-16 |
| DK133108C (da) | 1976-08-23 |
| IT954235B (it) | 1973-08-30 |
| DE2218211A1 (de) | 1972-11-09 |
| SE383349B (sv) | 1976-03-08 |
| CA966145A (en) | 1975-04-15 |
| NO136098B (no) | 1977-04-12 |
| NO136098C (no) | 1977-07-20 |
| AT319663B (de) | 1975-01-10 |
| BE782029A (fr) | 1972-07-31 |
| CH579093A5 (no) | 1976-08-31 |
| AT313917B (de) | 1974-03-11 |
| NL7204713A (no) | 1972-10-17 |
| NL177830C (nl) | 1985-12-02 |
| NL177830B (nl) | 1985-07-01 |
| GB1340167A (en) | 1973-12-12 |
| DK133108B (da) | 1976-03-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OD | Request for examination | ||
| 8172 | Supplementary division/partition in: |
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| D2 | Grant after examination | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: M & T CHEMICALS, INC., WOODBRIDGE, N.J., US |
|
| 8339 | Ceased/non-payment of the annual fee |