CA1064947A - Process for the manufacture of thianthrene based products - Google Patents
Process for the manufacture of thianthrene based productsInfo
- Publication number
- CA1064947A CA1064947A CA289,590A CA289590A CA1064947A CA 1064947 A CA1064947 A CA 1064947A CA 289590 A CA289590 A CA 289590A CA 1064947 A CA1064947 A CA 1064947A
- Authority
- CA
- Canada
- Prior art keywords
- thianthrene
- compound
- complex
- aluminum chloride
- process according
- 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
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 50
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 37
- -1 benzene compound Chemical class 0.000 claims abstract description 37
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 35
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 17
- 150000005029 thianthrenes Chemical class 0.000 claims abstract description 14
- 239000002879 Lewis base Substances 0.000 claims abstract description 13
- 150000007527 lewis bases Chemical class 0.000 claims abstract description 13
- 239000002002 slurry Substances 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims description 13
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical group CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 claims description 7
- LQCSUVWASPTLDK-UHFFFAOYSA-N 1,2-dichloro-3,4-dimethylthianthrene Chemical compound S1C2=CC=CC=C2SC2=C1C(C)=C(C)C(Cl)=C2Cl LQCSUVWASPTLDK-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000012035 limiting reagent Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XIGHKTWDPDTMFO-UHFFFAOYSA-N 1,2,3,4-tetramethylthianthrene Chemical class C1=CC=C2SC3=C(C)C(C)=C(C)C(C)=C3SC2=C1 XIGHKTWDPDTMFO-UHFFFAOYSA-N 0.000 description 1
- DGHKQBYAUUIYTD-UHFFFAOYSA-N 1-chloro-2,3-dimethylthianthrene Chemical compound S1C2=CC=CC=C2SC2=C1C=C(C)C(C)=C2Cl DGHKQBYAUUIYTD-UHFFFAOYSA-N 0.000 description 1
- OSOUNOBYRMOXQQ-UHFFFAOYSA-N 1-chloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000631130 Chrysophyllum argenteum Species 0.000 description 1
- ILXDAXZQNSOSAE-UHFFFAOYSA-N [AlH3].[Cl] Chemical compound [AlH3].[Cl] ILXDAXZQNSOSAE-UHFFFAOYSA-N 0.000 description 1
- HYJODZUSLXOFNC-UHFFFAOYSA-N [S].[Cl] Chemical compound [S].[Cl] HYJODZUSLXOFNC-UHFFFAOYSA-N 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B49/00—Sulfur dyes
- C09B49/12—Sulfur dyes from other compounds, e.g. other heterocyclic compounds
- C09B49/124—Sulfur dyes from other compounds, e.g. other heterocyclic compounds from polycarbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/737,320 US4091031A (en) | 1974-11-05 | 1976-11-01 | Process for the manufacture of substituted thianthrene based products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1064947A true CA1064947A (en) | 1979-10-23 |
Family
ID=24963442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA289,590A Expired CA1064947A (en) | 1976-11-01 | 1977-10-26 | Process for the manufacture of thianthrene based products |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5356673A (enrdf_load_stackoverflow) |
| BE (1) | BE860090A (enrdf_load_stackoverflow) |
| BR (1) | BR7705620A (enrdf_load_stackoverflow) |
| CA (1) | CA1064947A (enrdf_load_stackoverflow) |
| DE (1) | DE2739217A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2369277A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1575853A (enrdf_load_stackoverflow) |
| IT (1) | IT1087969B (enrdf_load_stackoverflow) |
| NL (1) | NL7710640A (enrdf_load_stackoverflow) |
-
1977
- 1977-08-16 JP JP9861977A patent/JPS5356673A/ja active Pending
- 1977-08-23 BR BR7705620A patent/BR7705620A/pt unknown
- 1977-08-23 GB GB3531077A patent/GB1575853A/en not_active Expired
- 1977-08-31 DE DE19772739217 patent/DE2739217A1/de not_active Withdrawn
- 1977-09-29 NL NL7710640A patent/NL7710640A/xx not_active Application Discontinuation
- 1977-10-25 BE BE182042A patent/BE860090A/xx not_active IP Right Cessation
- 1977-10-26 CA CA289,590A patent/CA1064947A/en not_active Expired
- 1977-10-26 IT IT2900177A patent/IT1087969B/it active
- 1977-10-27 FR FR7732457A patent/FR2369277A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT1087969B (it) | 1985-06-04 |
| NL7710640A (nl) | 1978-05-03 |
| DE2739217A1 (de) | 1978-05-11 |
| BE860090A (fr) | 1978-04-25 |
| BR7705620A (pt) | 1978-06-06 |
| FR2369277A1 (fr) | 1978-05-26 |
| FR2369277B1 (enrdf_load_stackoverflow) | 1982-09-10 |
| GB1575853A (en) | 1980-10-01 |
| JPS5356673A (en) | 1978-05-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| George et al. | A direct one-step preparation of bis (dinitrogen) complexes of molybdenum (0) from molybdenum (V) chloride | |
| US4683316A (en) | Method of preparation of dithiocarbamate complexes of molybdenum (VI) | |
| US4010214A (en) | Process for the preparation of 2,5-dichloro-p-xylene | |
| US2730526A (en) | Preparation of 2-benzothiazolyl sulfene morpholide | |
| CA1064947A (en) | Process for the manufacture of thianthrene based products | |
| US4091031A (en) | Process for the manufacture of substituted thianthrene based products | |
| US4504665A (en) | Process for producing chloronicotinic acid compounds | |
| US2623037A (en) | Sulfating polyvinyl alcohol | |
| US4225534A (en) | Process for the production of 2-chlorobenzonitrile derivatives | |
| US2845458A (en) | C-chloro-n, n, n'-trimethylformamidine hydrochloride | |
| KR100539326B1 (ko) | 구리 프탈로시아닌 또는 그 유도체 제조 방법 | |
| US4185053A (en) | Process for manufacturing substantially pure dialkyl phosphorochloridothionate | |
| US4221746A (en) | Preparation of hexanitrostilbene | |
| US4675447A (en) | Method for preparation of alkylsulfonyl alkylchlorobenzenes | |
| US3101365A (en) | Preparation of tetracyanoethylene by reacting cyanocarbon sulfides with metal cyanides, followed by oxidation | |
| US4144265A (en) | Process for the manufacture of m-trifluoromethyl benzyl nitrile | |
| US3989715A (en) | Process for manufacturing chlorothianthrenes | |
| HU183434B (en) | Process for preparing thio-bis/carbamates/ | |
| US3163667A (en) | Preparation of beta-sulfato-ethane sulfonamides and amine salts thereof | |
| US3947457A (en) | Method for preparing 2,5-dihalo- and 2,5,6-trihalopyridines | |
| US2715127A (en) | Process for the preparation of n, n'-diphenyl perylene diimid and the chlorinated dervatives thereof | |
| EP0334188A2 (en) | Process for producing aromatic nitrile | |
| CA1238329A (en) | 5-mercapto-1,2,3-thiadiazoles composition and process for preparing the same | |
| CN114644592B (zh) | 二氯嘧啶的制备方法 | |
| US3839394A (en) | Process for the preparation of substituted dinitrophenyl chloroformates |