DE2340668A1 - Verfahren zur herstellung von organochlorstannanen - Google Patents
Verfahren zur herstellung von organochlorstannanenInfo
- Publication number
- DE2340668A1 DE2340668A1 DE19732340668 DE2340668A DE2340668A1 DE 2340668 A1 DE2340668 A1 DE 2340668A1 DE 19732340668 DE19732340668 DE 19732340668 DE 2340668 A DE2340668 A DE 2340668A DE 2340668 A1 DE2340668 A1 DE 2340668A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- radicals
- radical
- unsaturated
- formula
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title description 6
- -1 tin halide Chemical class 0.000 claims description 28
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- TXSMUPJUALCAEE-UHFFFAOYSA-M chlorostannane Chemical class [SnH3]Cl TXSMUPJUALCAEE-UHFFFAOYSA-M 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 8
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- UBOGEXSQACVGEC-UHFFFAOYSA-K phenyltin(3+);trichloride Chemical compound Cl[Sn](Cl)(Cl)C1=CC=CC=C1 UBOGEXSQACVGEC-UHFFFAOYSA-K 0.000 description 5
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- OZOLEDRGOKKUNW-UHFFFAOYSA-M chloro(phenyl)stannane Chemical class Cl[SnH2]C1=CC=CC=C1 OZOLEDRGOKKUNW-UHFFFAOYSA-M 0.000 description 4
- GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000005051 trimethylchlorosilane Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- URNVMBADOXXKOA-UHFFFAOYSA-K trichloro(ethenyl)stannane Chemical compound Cl[Sn](Cl)(Cl)C=C URNVMBADOXXKOA-UHFFFAOYSA-K 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 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
- 238000009835 boiling Methods 0.000 description 2
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 description 2
- LWHKXKZPLXYXRO-UHFFFAOYSA-L dichloro-bis(ethenyl)stannane Chemical compound C=C[Sn](Cl)(Cl)C=C LWHKXKZPLXYXRO-UHFFFAOYSA-L 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- KXFSUVJPEQYUGN-UHFFFAOYSA-N trimethyl(phenyl)silane Chemical compound C[Si](C)(C)C1=CC=CC=C1 KXFSUVJPEQYUGN-UHFFFAOYSA-N 0.000 description 2
- HVIVCUXDNAQEOT-UHFFFAOYSA-K (4-chlorophenyl)tin(3+);trichloride Chemical compound ClC1=CC=C([Sn](Cl)(Cl)Cl)C=C1 HVIVCUXDNAQEOT-UHFFFAOYSA-K 0.000 description 1
- GXSSZJREKCITAD-ARJAWSKDSA-N (z)-4-ethenoxy-4-oxobut-2-enoic acid Chemical class OC(=O)\C=C/C(=O)OC=C GXSSZJREKCITAD-ARJAWSKDSA-N 0.000 description 1
- LYQUFFJYBBIRNF-UHFFFAOYSA-N 2,2-diphenylethenyl(trimethyl)silane Chemical compound C=1C=CC=CC=1C(=C[Si](C)(C)C)C1=CC=CC=C1 LYQUFFJYBBIRNF-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- MTWOEQJNRBNTTK-UHFFFAOYSA-L C1(=CC=CC=C1)CCCC[Sn](Cl)Cl Chemical compound C1(=CC=CC=C1)CCCC[Sn](Cl)Cl MTWOEQJNRBNTTK-UHFFFAOYSA-L 0.000 description 1
- KMWZHJWFVZPLAA-UHFFFAOYSA-L C1(=CC=CC=C1)C[Sn](Cl)Cl Chemical compound C1(=CC=CC=C1)C[Sn](Cl)Cl KMWZHJWFVZPLAA-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XVFHFCQGUWMCKR-UHFFFAOYSA-M Cl[SnH2]C=C Chemical class Cl[SnH2]C=C XVFHFCQGUWMCKR-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- ZPLRQSPYSZDKCM-UHFFFAOYSA-K benzyltin(3+);trichloride Chemical compound Cl[Sn](Cl)(Cl)CC1=CC=CC=C1 ZPLRQSPYSZDKCM-UHFFFAOYSA-K 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- USLZGQULWGROKV-UHFFFAOYSA-M chloro(diphenyl)stannane Chemical compound C=1C=CC=CC=1[SnH](Cl)C1=CC=CC=C1 USLZGQULWGROKV-UHFFFAOYSA-M 0.000 description 1
- KWYZNESIGBQHJK-UHFFFAOYSA-N chloro-dimethyl-phenylsilane Chemical compound C[Si](C)(Cl)C1=CC=CC=C1 KWYZNESIGBQHJK-UHFFFAOYSA-N 0.000 description 1
- WCTXJBYIXVVFCF-UHFFFAOYSA-M chlorotin Chemical class [Sn]Cl WCTXJBYIXVVFCF-UHFFFAOYSA-M 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- BESRBWLUVPELTD-UHFFFAOYSA-K cyclohexyltin(3+);trichloride Chemical compound Cl[Sn](Cl)(Cl)C1CCCCC1 BESRBWLUVPELTD-UHFFFAOYSA-K 0.000 description 1
- ISXUHJXWYNONDI-UHFFFAOYSA-L dichloro(diphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](Cl)(Cl)C1=CC=CC=C1 ISXUHJXWYNONDI-UHFFFAOYSA-L 0.000 description 1
- UHJADNQOGQLVKG-UHFFFAOYSA-L dichloro-[(e)-2-phenylethenyl]tin Chemical compound Cl[Sn](Cl)\C=C\C1=CC=CC=C1 UHJADNQOGQLVKG-UHFFFAOYSA-L 0.000 description 1
- JRAHXNQYHZPMCW-UHFFFAOYSA-N dichloro-bis(4-methylphenyl)silane Chemical compound C1=CC(C)=CC=C1[Si](Cl)(Cl)C1=CC=C(C)C=C1 JRAHXNQYHZPMCW-UHFFFAOYSA-N 0.000 description 1
- VVZXUNKOJSPQCZ-UHFFFAOYSA-L dichloro-ethenyl-phenylstannane Chemical compound C=C[Sn](Cl)(Cl)C1=CC=CC=C1 VVZXUNKOJSPQCZ-UHFFFAOYSA-L 0.000 description 1
- MRUIMSDHOCZKQH-UHFFFAOYSA-N dichloro-methyl-(4-methylphenyl)silane Chemical compound CC1=CC=C([Si](C)(Cl)Cl)C=C1 MRUIMSDHOCZKQH-UHFFFAOYSA-N 0.000 description 1
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001511 metal iodide Inorganic materials 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 101150101567 pat-2 gene Proteins 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
- YFRLQYJXUZRYDN-UHFFFAOYSA-K trichloro(methyl)stannane Chemical compound C[Sn](Cl)(Cl)Cl YFRLQYJXUZRYDN-UHFFFAOYSA-K 0.000 description 1
- INTLMJZQCBRQAT-UHFFFAOYSA-K trichloro(octyl)stannane Chemical compound CCCCCCCC[Sn](Cl)(Cl)Cl INTLMJZQCBRQAT-UHFFFAOYSA-K 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- OWZKYDTXRDQKBH-UHFFFAOYSA-K trichloro(prop-1-enyl)stannane Chemical compound CC=C[Sn](Cl)(Cl)Cl OWZKYDTXRDQKBH-UHFFFAOYSA-K 0.000 description 1
- XLOVMEQXRGQGAI-UHFFFAOYSA-K trichloro-(2-methylphenyl)stannane Chemical compound CC1=CC=CC=C1[Sn](Cl)(Cl)Cl XLOVMEQXRGQGAI-UHFFFAOYSA-K 0.000 description 1
- ABADVTXFGWCNBV-UHFFFAOYSA-N trichloro-(4-chlorophenyl)silane Chemical compound ClC1=CC=C([Si](Cl)(Cl)Cl)C=C1 ABADVTXFGWCNBV-UHFFFAOYSA-N 0.000 description 1
- IIWSLXWOGWUDPL-UHFFFAOYSA-N trimethyl(prop-1-en-2-yl)silane Chemical compound CC(=C)[Si](C)(C)C IIWSLXWOGWUDPL-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7229099A FR2195633A1 (en) | 1972-08-11 | 1972-08-11 | Phenyl- and alkenyl- chlorostannanes prodn - by reaction of tin halides and aromatic or alkenyl- organosilicon cpds, intermediates for fungicides and plastics stabilisers |
| FR7229100A FR2195634A1 (en) | 1972-08-11 | 1972-08-11 | Phenyl- and alkenyl- chlorostannanes prodn - by reaction of tin halides and aromatic or alkenyl- organosilicon cpds, intermediates for fungicides and plastics stabilisers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2340668A1 true DE2340668A1 (de) | 1974-03-07 |
Family
ID=26217277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732340668 Pending DE2340668A1 (de) | 1972-08-11 | 1973-08-10 | Verfahren zur herstellung von organochlorstannanen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3839382A (enExample) |
| JP (1) | JPS49108025A (enExample) |
| CH (1) | CH591506A5 (enExample) |
| DE (1) | DE2340668A1 (enExample) |
| ES (1) | ES417802A1 (enExample) |
| GB (1) | GB1436719A (enExample) |
| IE (1) | IE38179B1 (enExample) |
| IT (1) | IT995180B (enExample) |
| NL (1) | NL7310786A (enExample) |
-
1973
- 1973-08-03 NL NL7310786A patent/NL7310786A/xx unknown
- 1973-08-09 JP JP48089634A patent/JPS49108025A/ja active Pending
- 1973-08-10 DE DE19732340668 patent/DE2340668A1/de active Pending
- 1973-08-10 IE IE1376/73A patent/IE38179B1/xx unknown
- 1973-08-10 IT IT27776/73A patent/IT995180B/it active
- 1973-08-10 CH CH1157573A patent/CH591506A5/xx not_active IP Right Cessation
- 1973-08-10 US US00387508A patent/US3839382A/en not_active Expired - Lifetime
- 1973-08-10 GB GB3808673A patent/GB1436719A/en not_active Expired
- 1973-08-11 ES ES417802A patent/ES417802A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH591506A5 (enExample) | 1977-09-30 |
| NL7310786A (enExample) | 1974-02-13 |
| IT995180B (it) | 1975-11-10 |
| GB1436719A (en) | 1976-05-26 |
| ES417802A1 (es) | 1976-06-16 |
| IE38179B1 (en) | 1978-01-18 |
| IE38179L (en) | 1974-02-11 |
| JPS49108025A (enExample) | 1974-10-14 |
| US3839382A (en) | 1974-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |