DE2116978A1 - Verfahren zur Herstellung von Thiophenolen - Google Patents
Verfahren zur Herstellung von ThiophenolenInfo
- Publication number
- DE2116978A1 DE2116978A1 DE19712116978 DE2116978A DE2116978A1 DE 2116978 A1 DE2116978 A1 DE 2116978A1 DE 19712116978 DE19712116978 DE 19712116978 DE 2116978 A DE2116978 A DE 2116978A DE 2116978 A1 DE2116978 A1 DE 2116978A1
- Authority
- DE
- Germany
- Prior art keywords
- thiophenols
- suitable solvent
- hydrazine
- acid
- stage
- 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
- 238000000034 method Methods 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000002019 disulfides Chemical class 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- OPZGHHMHHWXKAA-UHFFFAOYSA-N benzenesulfonic acid;hydrochloride Chemical compound Cl.OS(=O)(=O)C1=CC=CC=C1 OPZGHHMHHWXKAA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 1
- -1 hydroxy, amino Chemical group 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 5
- 238000003776 cleavage reaction Methods 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000006894 reductive elimination reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- BKVUMYOQSQOQMN-UHFFFAOYSA-N 1-chloro-4-chlorosulfonyloxybenzene Chemical compound ClC1=CC=C(OS(Cl)(=O)=O)C=C1 BKVUMYOQSQOQMN-UHFFFAOYSA-N 0.000 description 1
- MTOJDBAZGOYUOZ-UHFFFAOYSA-N 4-aminobenzenesulfonyl chloride Chemical compound NC1=CC=C(S(Cl)(=O)=O)C=C1 MTOJDBAZGOYUOZ-UHFFFAOYSA-N 0.000 description 1
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 1
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PUPSOTNKLABLTE-UHFFFAOYSA-N C(C)C1=CC(=C(C=C1)S(=O)(=O)Cl)NCCC Chemical compound C(C)C1=CC(=C(C=C1)S(=O)(=O)Cl)NCCC PUPSOTNKLABLTE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003960 organic solvent Substances 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712116978 DE2116978A1 (de) | 1971-04-07 | 1971-04-07 | Verfahren zur Herstellung von Thiophenolen |
| NL7204470A NL7204470A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-04-07 | 1972-04-04 | |
| IL7239136A IL39136A (en) | 1971-04-07 | 1972-04-04 | Process for the preparation of thiophenols |
| IT89536/72A IT967042B (it) | 1971-04-07 | 1972-04-05 | Procedimento per la preparazione di tiofenoli |
| CH499472A CH565759A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-04-07 | 1972-04-05 | |
| BE781737A BE781737A (fr) | 1971-04-07 | 1972-04-06 | Procede de preparation de thiophenols |
| GB1595472A GB1331404A (en) | 1971-04-07 | 1972-04-06 | Process for the preparation of thiophenols |
| FR7212327A FR2136268A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-04-07 | 1972-04-07 | |
| US05/466,312 US4006186A (en) | 1971-04-07 | 1974-05-02 | Process for the preparation of thiophenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712116978 DE2116978A1 (de) | 1971-04-07 | 1971-04-07 | Verfahren zur Herstellung von Thiophenolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2116978A1 true DE2116978A1 (de) | 1972-10-19 |
Family
ID=5804128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712116978 Pending DE2116978A1 (de) | 1971-04-07 | 1971-04-07 | Verfahren zur Herstellung von Thiophenolen |
Country Status (8)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110804743A (zh) * | 2019-10-17 | 2020-02-18 | 李旭 | 一种对羟基苯硫酚的脱羟还原方法 |
-
1971
- 1971-04-07 DE DE19712116978 patent/DE2116978A1/de active Pending
-
1972
- 1972-04-04 IL IL7239136A patent/IL39136A/xx unknown
- 1972-04-04 NL NL7204470A patent/NL7204470A/xx unknown
- 1972-04-05 CH CH499472A patent/CH565759A5/xx not_active IP Right Cessation
- 1972-04-05 IT IT89536/72A patent/IT967042B/it active
- 1972-04-06 GB GB1595472A patent/GB1331404A/en not_active Expired
- 1972-04-06 BE BE781737A patent/BE781737A/xx unknown
- 1972-04-07 FR FR7212327A patent/FR2136268A5/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110804743A (zh) * | 2019-10-17 | 2020-02-18 | 李旭 | 一种对羟基苯硫酚的脱羟还原方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7204470A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-10-10 |
| BE781737A (fr) | 1972-10-06 |
| FR2136268A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-12-22 |
| IL39136A0 (en) | 1972-06-28 |
| IL39136A (en) | 1974-12-31 |
| IT967042B (it) | 1974-02-28 |
| GB1331404A (en) | 1973-09-26 |
| CH565759A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-08-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |