DE1274121C2 - Verfahren zur Herstellung von aromatischen Dithiocarbonsaeuren - Google Patents
Verfahren zur Herstellung von aromatischen DithiocarbonsaeurenInfo
- Publication number
- DE1274121C2 DE1274121C2 DE1967B0093036 DEB0093036A DE1274121C2 DE 1274121 C2 DE1274121 C2 DE 1274121C2 DE 1967B0093036 DE1967B0093036 DE 1967B0093036 DE B0093036 A DEB0093036 A DE B0093036A DE 1274121 C2 DE1274121 C2 DE 1274121C2
- Authority
- DE
- Germany
- Prior art keywords
- aromatic
- parts
- dithiocarboxylic acids
- production
- 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
- -1 aromatic dithiocarboxylic acids Chemical class 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- ZGRWZUDBZZBJQB-UHFFFAOYSA-N benzenecarbodithioic acid Chemical compound SC(=S)C1=CC=CC=C1 ZGRWZUDBZZBJQB-UHFFFAOYSA-N 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000004970 halomethyl group Chemical group 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- LBOBESSDSGODDD-UHFFFAOYSA-N 1,3-dichloro-2-(chloromethyl)benzene Chemical compound ClCC1=C(Cl)C=CC=C1Cl LBOBESSDSGODDD-UHFFFAOYSA-N 0.000 description 2
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 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
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- RFPLNXZSBSXEMD-UHFFFAOYSA-N 2,6-dichloro-N-cyclohexylbenzenecarbothioamide Chemical compound ClC1=CC=CC(Cl)=C1C(=S)NC1CCCCC1 RFPLNXZSBSXEMD-UHFFFAOYSA-N 0.000 description 1
- GUSBTHQFCZCHMJ-UHFFFAOYSA-N 2,6-dichlorobenzenecarbodithioic acid Chemical compound ClC1=C(C(=S)S)C(=CC=C1)Cl GUSBTHQFCZCHMJ-UHFFFAOYSA-N 0.000 description 1
- LHMUUYGTNILHKI-UHFFFAOYSA-N 3-chloropentan-3-ylbenzene Chemical class CCC(Cl)(CC)C1=CC=CC=C1 LHMUUYGTNILHKI-UHFFFAOYSA-N 0.000 description 1
- ZYXBMZWOPXQKMJ-UHFFFAOYSA-N 4-chlorobenzenecarbodithioic acid Chemical compound SC(=S)C1=CC=C(Cl)C=C1 ZYXBMZWOPXQKMJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- OJMURUCKSBBGML-UHFFFAOYSA-N [bromo(dichloro)methyl]benzene Chemical class ClC(Cl)(Br)C1=CC=CC=C1 OJMURUCKSBBGML-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- BQHKZJWYXFKFKS-UHFFFAOYSA-N anthracene;chloromethane Chemical class ClC.C1=CC=CC2=CC3=CC=CC=C3C=C21 BQHKZJWYXFKFKS-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 150000002023 dithiocarboxylic acids Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000006372 monohalo methyl group Chemical group 0.000 description 1
- WOBYQCDJHWATRG-UHFFFAOYSA-N n-cyclohexylbenzenecarbothioamide Chemical compound C=1C=CC=CC=1C(=S)NC1CCCCC1 WOBYQCDJHWATRG-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 description 1
- PGMZELUBYYZRQZ-UHFFFAOYSA-L potassium sodium diphenoxide Chemical class [Na+].[K+].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 PGMZELUBYYZRQZ-UHFFFAOYSA-L 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967B0093036 DE1274121C2 (de) | 1967-06-16 | 1967-06-16 | Verfahren zur Herstellung von aromatischen Dithiocarbonsaeuren |
| BE716384D BE716384A (cs) | 1967-06-16 | 1968-06-11 | |
| FR1576603D FR1576603A (cs) | 1967-06-16 | 1968-06-12 | |
| NL6808333A NL6808333A (cs) | 1967-06-16 | 1968-06-13 | |
| GB2842668A GB1219626A (en) | 1967-06-16 | 1968-06-14 | Production of aromatic dithiocarboxylic acids and salts thereof |
| CH883968A CH498101A (de) | 1967-06-16 | 1968-06-14 | Verfahren zur Herstellung von aromatischen Dithiocarbonsäuren oder Polydithiocarbonsäuren |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967B0093036 DE1274121C2 (de) | 1967-06-16 | 1967-06-16 | Verfahren zur Herstellung von aromatischen Dithiocarbonsaeuren |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1274121B DE1274121B (de) | 1968-08-01 |
| DE1274121C2 true DE1274121C2 (de) | 1969-03-20 |
Family
ID=6986729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967B0093036 Expired DE1274121C2 (de) | 1967-06-16 | 1967-06-16 | Verfahren zur Herstellung von aromatischen Dithiocarbonsaeuren |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE716384A (cs) |
| CH (1) | CH498101A (cs) |
| DE (1) | DE1274121C2 (cs) |
| FR (1) | FR1576603A (cs) |
| GB (1) | GB1219626A (cs) |
| NL (1) | NL6808333A (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4456509A (en) * | 1982-07-06 | 1984-06-26 | Exxon Research And Engineering Co. | Method of preparing metal dithiobenzoates (PNE-361) |
-
1967
- 1967-06-16 DE DE1967B0093036 patent/DE1274121C2/de not_active Expired
-
1968
- 1968-06-11 BE BE716384D patent/BE716384A/xx not_active IP Right Cessation
- 1968-06-12 FR FR1576603D patent/FR1576603A/fr not_active Expired
- 1968-06-13 NL NL6808333A patent/NL6808333A/xx unknown
- 1968-06-14 CH CH883968A patent/CH498101A/de not_active IP Right Cessation
- 1968-06-14 GB GB2842668A patent/GB1219626A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH498101A (de) | 1970-10-31 |
| DE1274121B (de) | 1968-08-01 |
| BE716384A (cs) | 1968-12-11 |
| NL6808333A (cs) | 1968-12-17 |
| GB1219626A (en) | 1971-01-20 |
| FR1576603A (cs) | 1969-08-01 |
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