DE1955463C3 - Verfahren zur Herstellung von Tricyclohexylzinnchlorid - Google Patents
Verfahren zur Herstellung von TricyclohexylzinnchloridInfo
- Publication number
- DE1955463C3 DE1955463C3 DE1955463A DE1955463A DE1955463C3 DE 1955463 C3 DE1955463 C3 DE 1955463C3 DE 1955463 A DE1955463 A DE 1955463A DE 1955463 A DE1955463 A DE 1955463A DE 1955463 C3 DE1955463 C3 DE 1955463C3
- Authority
- DE
- Germany
- Prior art keywords
- chloride
- tricyclohexyltin
- mol
- separated
- reaction
- 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 13
- YICRPERKKBDRSP-UHFFFAOYSA-N methyl 3-amino-4-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(C)C=1N YICRPERKKBDRSP-UHFFFAOYSA-N 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- -1 tricyclohexyltin halide Chemical class 0.000 description 6
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 2
- UBOGEXSQACVGEC-UHFFFAOYSA-K phenyltin(3+);trichloride Chemical compound Cl[Sn](Cl)(Cl)C1=CC=CC=C1 UBOGEXSQACVGEC-UHFFFAOYSA-K 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 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
- LRLNMPJWOOOYNO-UHFFFAOYSA-N tricyclohexyl(phenyl)stannane Chemical compound C1CCCCC1[Sn](C=1C=CC=CC=1)(C1CCCCC1)C1CCCCC1 LRLNMPJWOOOYNO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001481828 Glyptocephalus cynoglossus Species 0.000 description 1
- 229910008433 SnCU Inorganic materials 0.000 description 1
- WMJMABVHDMRMJA-UHFFFAOYSA-M [Cl-].[Mg+]C1CCCCC1 Chemical compound [Cl-].[Mg+]C1CCCCC1 WMJMABVHDMRMJA-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- VKAAGRLEXPKJAI-UHFFFAOYSA-N cyclohexyltin Chemical compound [Sn]C1CCCCC1 VKAAGRLEXPKJAI-UHFFFAOYSA-N 0.000 description 1
- NXLNBJXGFFFGIT-UHFFFAOYSA-L dicyclohexyltin(2+);dichloride Chemical compound C1CCCCC1[Sn](Cl)(Cl)C1CCCCC1 NXLNBJXGFFFGIT-UHFFFAOYSA-L 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ODOPKAJVFRHHGM-UHFFFAOYSA-N phenyltin Chemical compound [Sn]C1=CC=CC=C1 ODOPKAJVFRHHGM-UHFFFAOYSA-N 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
- KHOIFEACBCQMRX-UHFFFAOYSA-N tricyclohexyl(methyl)stannane Chemical compound C1CCCCC1[Sn](C1CCCCC1)(C)C1CCCCC1 KHOIFEACBCQMRX-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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 |
|---|---|---|---|
| US77333168A | 1968-11-04 | 1968-11-04 | |
| US81678369A | 1969-04-16 | 1969-04-16 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1955463A1 DE1955463A1 (de) | 1970-05-06 |
| DE1955463B2 DE1955463B2 (de) | 1978-11-16 |
| DE1955463C3 true DE1955463C3 (de) | 1979-07-12 |
Family
ID=27118739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1955463A Expired DE1955463C3 (de) | 1968-11-04 | 1969-11-04 | Verfahren zur Herstellung von Tricyclohexylzinnchlorid |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT293437B (enExample) |
| BE (1) | BE741260A (enExample) |
| BR (1) | BR6913863D0 (enExample) |
| CH (1) | CH539655A (enExample) |
| DE (1) | DE1955463C3 (enExample) |
| DK (1) | DK130300B (enExample) |
| ES (1) | ES373121A1 (enExample) |
| FR (1) | FR2022521A1 (enExample) |
| GB (1) | GB1262986A (enExample) |
| IL (1) | IL33291A (enExample) |
| NL (1) | NL166946C (enExample) |
| NO (1) | NO131934C (enExample) |
| SE (2) | SE361481B (enExample) |
-
1969
- 1969-11-03 DK DK579769AA patent/DK130300B/da not_active IP Right Cessation
- 1969-11-03 FR FR6937720A patent/FR2022521A1/fr active Pending
- 1969-11-03 SE SE15018/69A patent/SE361481B/xx unknown
- 1969-11-03 BR BR213863/69A patent/BR6913863D0/pt unknown
- 1969-11-03 ES ES373121A patent/ES373121A1/es not_active Expired
- 1969-11-03 SE SE7216419A patent/SE393382B/xx unknown
- 1969-11-03 NO NO4341/69A patent/NO131934C/no unknown
- 1969-11-03 IL IL33291A patent/IL33291A/xx unknown
- 1969-11-04 DE DE1955463A patent/DE1955463C3/de not_active Expired
- 1969-11-04 GB GB54060/69A patent/GB1262986A/en not_active Expired
- 1969-11-04 BE BE741260D patent/BE741260A/xx unknown
- 1969-11-04 AT AT1036469A patent/AT293437B/de not_active IP Right Cessation
- 1969-11-04 NL NL6916581.A patent/NL166946C/xx not_active IP Right Cessation
- 1969-11-04 CH CH1644669A patent/CH539655A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO131934C (enExample) | 1975-08-27 |
| ES373121A1 (es) | 1971-12-16 |
| NO131934B (enExample) | 1975-05-20 |
| DK130300B (da) | 1975-02-03 |
| SE393382B (sv) | 1977-05-09 |
| GB1262986A (en) | 1972-02-09 |
| DK130300C (enExample) | 1975-06-30 |
| DE1955463A1 (de) | 1970-05-06 |
| DE1955463B2 (de) | 1978-11-16 |
| IL33291A0 (en) | 1970-01-29 |
| IL33291A (en) | 1972-12-29 |
| CH539655A (fr) | 1973-07-31 |
| BR6913863D0 (pt) | 1973-04-05 |
| NL6916581A (enExample) | 1970-05-08 |
| SE361481B (enExample) | 1973-11-05 |
| AT293437B (de) | 1971-10-11 |
| FR2022521A1 (enExample) | 1970-07-31 |
| NL166946C (nl) | 1981-10-15 |
| NL166946B (nl) | 1981-05-15 |
| BE741260A (enExample) | 1970-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OI | Miscellaneous see part 1 | ||
| OI | Miscellaneous see part 1 | ||
| C3 | Grant after two publication steps (3rd publication) |