DE2018381C3 - Verfahren zur Herstellung von Thiophosgen - Google Patents
Verfahren zur Herstellung von ThiophosgenInfo
- Publication number
- DE2018381C3 DE2018381C3 DE2018381A DE2018381A DE2018381C3 DE 2018381 C3 DE2018381 C3 DE 2018381C3 DE 2018381 A DE2018381 A DE 2018381A DE 2018381 A DE2018381 A DE 2018381A DE 2018381 C3 DE2018381 C3 DE 2018381C3
- Authority
- DE
- Germany
- Prior art keywords
- thiophosgene
- reaction
- chloride
- silica gel
- hydrogen sulfide
- 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 34
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title description 8
- 238000006243 chemical reaction Methods 0.000 claims description 27
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 21
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 claims description 20
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000000741 silica gel Substances 0.000 claims description 9
- 229910002027 silica gel Inorganic materials 0.000 claims description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
- 239000008246 gaseous mixture Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
- USAIOOFEIMNEDN-UHFFFAOYSA-L disodium;carbonotrithioate Chemical compound [Na+].[Na+].[S-]C([S-])=S USAIOOFEIMNEDN-UHFFFAOYSA-L 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- -1 methylethyl Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 241000557876 Centaurea cineraria Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 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
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- MGFAJHVKMKDQIT-UHFFFAOYSA-N [C].[C].[C].[C].[C] Chemical compound [C].[C].[C].[C].[C] MGFAJHVKMKDQIT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N carbon tetrachloride Substances ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical class SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- XYWDPYKBIRQXQS-UHFFFAOYSA-N di-isopropyl sulphide Natural products CC(C)SC(C)C XYWDPYKBIRQXQS-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N dimethyl monosulfide Natural products CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical compound [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 1
- 239000012989 trithiocarbonate Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/70—Compounds containing carbon and sulfur, e.g. thiophosgene
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/80—Phosgene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Silicon Compounds (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2018381A DE2018381C3 (de) | 1970-04-17 | 1970-04-17 | Verfahren zur Herstellung von Thiophosgen |
| CA104936A CA930374A (en) | 1970-04-17 | 1971-02-09 | Process for the preparation of thiophosgene |
| IL36169A IL36169A (en) | 1970-04-17 | 1971-02-10 | The preparation of thiophosgene |
| BE763639A BE763639A (fr) | 1970-04-17 | 1971-03-02 | Procede pour la preparation de thiophosgene |
| SE02867/71A SE359283B (enExample) | 1970-04-17 | 1971-03-05 | |
| CH348771A CH538427A (de) | 1970-04-17 | 1971-03-10 | Verfahren zur Herstellung von Thiophosgen |
| CS1969A CS162743B2 (enExample) | 1970-04-17 | 1971-03-18 | |
| AT02336/71A AT312558B (de) | 1970-04-17 | 1971-03-18 | Verfahren zur herstellung von thiophosgen |
| RO66347A RO57594A (enExample) | 1970-04-17 | 1971-03-22 | |
| ES389471A ES389471A1 (es) | 1970-04-17 | 1971-03-23 | Procedimiento para la preparacion de tiofosgeno. |
| SU1643385A SU372809A1 (ru) | 1971-04-06 | Способ получения тиофосгена | |
| NL7104749A NL7104749A (enExample) | 1970-04-17 | 1971-04-08 | |
| HUGA1048A HU162409B (enExample) | 1970-04-17 | 1971-04-08 | |
| US134495A US3699161A (en) | 1970-04-17 | 1971-04-15 | Process for the production of thiophosgene |
| FR7113637A FR2089822A5 (enExample) | 1970-04-17 | 1971-04-16 | |
| GB1289060D GB1289060A (enExample) | 1970-04-17 | 1971-04-19 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2018381A DE2018381C3 (de) | 1970-04-17 | 1970-04-17 | Verfahren zur Herstellung von Thiophosgen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2018381A1 DE2018381A1 (de) | 1971-11-04 |
| DE2018381B2 DE2018381B2 (de) | 1973-10-04 |
| DE2018381C3 true DE2018381C3 (de) | 1974-05-16 |
Family
ID=5768290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2018381A Expired DE2018381C3 (de) | 1970-04-17 | 1970-04-17 | Verfahren zur Herstellung von Thiophosgen |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3699161A (enExample) |
| AT (1) | AT312558B (enExample) |
| BE (1) | BE763639A (enExample) |
| CA (1) | CA930374A (enExample) |
| CH (1) | CH538427A (enExample) |
| CS (1) | CS162743B2 (enExample) |
| DE (1) | DE2018381C3 (enExample) |
| ES (1) | ES389471A1 (enExample) |
| FR (1) | FR2089822A5 (enExample) |
| GB (1) | GB1289060A (enExample) |
| HU (1) | HU162409B (enExample) |
| IL (1) | IL36169A (enExample) |
| NL (1) | NL7104749A (enExample) |
| RO (1) | RO57594A (enExample) |
| SE (1) | SE359283B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2326396B2 (de) * | 1973-05-24 | 1976-09-30 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur herstellung von thiophosgen |
| US7000036B2 (en) * | 2003-05-12 | 2006-02-14 | International Business Machines Corporation | Extended input/output measurement facilities |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3150176A (en) * | 1961-05-29 | 1964-09-22 | Stauffer Chemical Co | Thiophosgene |
-
1970
- 1970-04-17 DE DE2018381A patent/DE2018381C3/de not_active Expired
-
1971
- 1971-02-09 CA CA104936A patent/CA930374A/en not_active Expired
- 1971-02-10 IL IL36169A patent/IL36169A/xx unknown
- 1971-03-02 BE BE763639A patent/BE763639A/xx unknown
- 1971-03-05 SE SE02867/71A patent/SE359283B/xx unknown
- 1971-03-10 CH CH348771A patent/CH538427A/de not_active IP Right Cessation
- 1971-03-18 CS CS1969A patent/CS162743B2/cs unknown
- 1971-03-18 AT AT02336/71A patent/AT312558B/de not_active IP Right Cessation
- 1971-03-22 RO RO66347A patent/RO57594A/ro unknown
- 1971-03-23 ES ES389471A patent/ES389471A1/es not_active Expired
- 1971-04-08 HU HUGA1048A patent/HU162409B/hu unknown
- 1971-04-08 NL NL7104749A patent/NL7104749A/xx unknown
- 1971-04-15 US US134495A patent/US3699161A/en not_active Expired - Lifetime
- 1971-04-16 FR FR7113637A patent/FR2089822A5/fr not_active Expired
- 1971-04-19 GB GB1289060D patent/GB1289060A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA930374A (en) | 1973-07-17 |
| SU372809A3 (enExample) | 1973-03-01 |
| CS162743B2 (enExample) | 1975-07-15 |
| ES389471A1 (es) | 1973-06-16 |
| AT312558B (de) | 1973-12-15 |
| CH538427A (de) | 1973-06-30 |
| DE2018381A1 (de) | 1971-11-04 |
| RO57594A (enExample) | 1975-01-15 |
| NL7104749A (enExample) | 1971-10-19 |
| US3699161A (en) | 1972-10-17 |
| FR2089822A5 (enExample) | 1972-01-07 |
| GB1289060A (enExample) | 1972-09-13 |
| DE2018381B2 (de) | 1973-10-04 |
| SE359283B (enExample) | 1973-08-27 |
| IL36169A (en) | 1974-03-14 |
| IL36169A0 (en) | 1971-04-28 |
| BE763639A (fr) | 1971-08-02 |
| HU162409B (enExample) | 1973-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |