CA1064946A - Process for the manufacture of thianthrene - Google Patents
Process for the manufacture of thianthreneInfo
- Publication number
- CA1064946A CA1064946A CA238,297A CA238297A CA1064946A CA 1064946 A CA1064946 A CA 1064946A CA 238297 A CA238297 A CA 238297A CA 1064946 A CA1064946 A CA 1064946A
- Authority
- CA
- Canada
- Prior art keywords
- thianthrene
- benzene
- 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 54
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 105
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 34
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 21
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000002002 slurry Substances 0.000 claims abstract description 10
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 239000002879 Lewis base Substances 0.000 claims abstract description 4
- 150000007527 lewis bases Chemical class 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract 2
- 239000000047 product Substances 0.000 claims description 11
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 6
- 239000012535 impurity Substances 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 13
- 239000011593 sulfur Substances 0.000 description 12
- 229960005349 sulfur Drugs 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- 235000001508 sulfur Nutrition 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000007789 gas Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000012035 limiting reagent Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
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 |
|---|---|---|---|
| US05/521,108 US3997560A (en) | 1974-11-05 | 1974-11-05 | Process for the manufacture of thianthrene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1064946A true CA1064946A (en) | 1979-10-23 |
Family
ID=24075395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA238,297A Expired CA1064946A (en) | 1974-11-05 | 1975-10-24 | Process for the manufacture of thianthrene |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US3997560A (enExample) |
| JP (1) | JPS5169521A (enExample) |
| BR (1) | BR7507102A (enExample) |
| CA (1) | CA1064946A (enExample) |
| CH (1) | CH602704A5 (enExample) |
| DE (1) | DE2549435A1 (enExample) |
| FR (1) | FR2290436A1 (enExample) |
| GB (1) | GB1456950A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3997560A (en) * | 1974-11-05 | 1976-12-14 | Hooker Chemicals & Plastics Corporation | Process for the manufacture of thianthrene |
| US4139516A (en) * | 1977-08-05 | 1979-02-13 | Hooker Chemicals & Plastics Corp. | Process for the preparation of thianthrene compounds |
| RU2165418C1 (ru) * | 2000-01-26 | 2001-04-20 | Ярославский государственный технический университет | 2,3,7,8-тиантрентетракарбонитрил |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3997560A (en) * | 1974-11-05 | 1976-12-14 | Hooker Chemicals & Plastics Corporation | Process for the manufacture of thianthrene |
-
1974
- 1974-11-05 US US05/521,108 patent/US3997560A/en not_active Expired - Lifetime
-
1975
- 1975-10-24 CA CA238,297A patent/CA1064946A/en not_active Expired
- 1975-10-29 BR BR7507102*A patent/BR7507102A/pt unknown
- 1975-10-30 GB GB4498675A patent/GB1456950A/en not_active Expired
- 1975-10-31 FR FR7533469A patent/FR2290436A1/fr active Granted
- 1975-10-31 CH CH1412175A patent/CH602704A5/xx not_active IP Right Cessation
- 1975-11-04 DE DE19752549435 patent/DE2549435A1/de not_active Ceased
- 1975-11-04 JP JP50132410A patent/JPS5169521A/ja active Pending
-
1976
- 1976-11-01 US US05/737,320 patent/US4091031A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BR7507102A (pt) | 1976-08-10 |
| CH602704A5 (enExample) | 1978-07-31 |
| US3997560A (en) | 1976-12-14 |
| JPS5169521A (enExample) | 1976-06-16 |
| FR2290436A1 (fr) | 1976-06-04 |
| DE2549435A1 (de) | 1976-05-13 |
| FR2290436B1 (enExample) | 1978-05-12 |
| US4091031A (en) | 1978-05-23 |
| GB1456950A (en) | 1976-12-01 |
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