DE2244652C3 - Verfahren zur Herstellung von 2,3-Dicyan-1,4-dithiaanthrahydrochinon und -anthrachinon - Google Patents
Verfahren zur Herstellung von 2,3-Dicyan-1,4-dithiaanthrahydrochinon und -anthrachinonInfo
- Publication number
- DE2244652C3 DE2244652C3 DE2244652A DE2244652A DE2244652C3 DE 2244652 C3 DE2244652 C3 DE 2244652C3 DE 2244652 A DE2244652 A DE 2244652A DE 2244652 A DE2244652 A DE 2244652A DE 2244652 C3 DE2244652 C3 DE 2244652C3
- Authority
- DE
- Germany
- Prior art keywords
- dicyano
- dithiaanthrahydroquinone
- anthraquinone
- preparation
- acid
- 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 10
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims description 4
- 150000004056 anthraquinones Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 230000018044 dehydration Effects 0.000 claims description 5
- 238000006297 dehydration reaction Methods 0.000 claims description 5
- 229930192627 Naphthoquinone Natural products 0.000 claims description 3
- 150000002791 naphthoquinones Chemical class 0.000 claims description 3
- CCTJHVLTAJTPBV-UHFFFAOYSA-N 2-chloro-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(Cl)=CC(=O)C2=C1 CCTJHVLTAJTPBV-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 5
- 239000005764 Dithianon Substances 0.000 description 5
- PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 208000005156 Dehydration Diseases 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000012024 dehydrating agents Substances 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- DMDOIBWPFWJPQJ-UHFFFAOYSA-N 2,3-bis(sulfanyl)but-2-enedinitrile Chemical compound N#CC(S)=C(S)C#N DMDOIBWPFWJPQJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- -1 anthrahydroquinone compound Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- PCFMUWBCZZUMRX-UHFFFAOYSA-N 9,10-Dihydroxyanthracene Chemical compound C1=CC=C2C(O)=C(C=CC=C3)C3=C(O)C2=C1 PCFMUWBCZZUMRX-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- RLYTZHQLDITXLO-UHFFFAOYSA-N ethene-1,2-dithiol Chemical compound SC=CS RLYTZHQLDITXLO-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2244652A DE2244652C3 (de) | 1972-09-12 | 1972-09-12 | Verfahren zur Herstellung von 2,3-Dicyan-1,4-dithiaanthrahydrochinon und -anthrachinon |
| CH1292773A CH584708A5 (enExample) | 1972-09-12 | 1973-09-07 | |
| GB4259373A GB1432827A (en) | 1972-09-12 | 1973-09-11 | Process for the production of 2,3-dicyano-1,4-dithiaanthrahydro quinone and -anthraquinone |
| JP48102542A JPS4992076A (enExample) | 1972-09-12 | 1973-09-11 | |
| IL43200A IL43200A (en) | 1972-09-12 | 1973-09-11 | Preparation of 2,3-dicyano-1,4-dithia-anthrahydroquinone and-anthraquinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2244652A DE2244652C3 (de) | 1972-09-12 | 1972-09-12 | Verfahren zur Herstellung von 2,3-Dicyan-1,4-dithiaanthrahydrochinon und -anthrachinon |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2244652A1 DE2244652A1 (de) | 1974-03-21 |
| DE2244652B2 DE2244652B2 (de) | 1980-07-31 |
| DE2244652C3 true DE2244652C3 (de) | 1981-03-19 |
Family
ID=5856080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2244652A Expired DE2244652C3 (de) | 1972-09-12 | 1972-09-12 | Verfahren zur Herstellung von 2,3-Dicyan-1,4-dithiaanthrahydrochinon und -anthrachinon |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4992076A (enExample) |
| CH (1) | CH584708A5 (enExample) |
| DE (1) | DE2244652C3 (enExample) |
| GB (1) | GB1432827A (enExample) |
| IL (1) | IL43200A (enExample) |
-
1972
- 1972-09-12 DE DE2244652A patent/DE2244652C3/de not_active Expired
-
1973
- 1973-09-07 CH CH1292773A patent/CH584708A5/xx not_active IP Right Cessation
- 1973-09-11 GB GB4259373A patent/GB1432827A/en not_active Expired
- 1973-09-11 JP JP48102542A patent/JPS4992076A/ja active Pending
- 1973-09-11 IL IL43200A patent/IL43200A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1432827A (en) | 1976-04-22 |
| DE2244652A1 (de) | 1974-03-21 |
| CH584708A5 (enExample) | 1977-02-15 |
| DE2244652B2 (de) | 1980-07-31 |
| IL43200A0 (en) | 1973-11-28 |
| JPS4992076A (enExample) | 1974-09-03 |
| IL43200A (en) | 1976-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |