DE2041547A1 - Verfahren zur Herstellung von Anthrachinon-alpha-sulfonsaeuren - Google Patents
Verfahren zur Herstellung von Anthrachinon-alpha-sulfonsaeurenInfo
- Publication number
- DE2041547A1 DE2041547A1 DE19702041547 DE2041547A DE2041547A1 DE 2041547 A1 DE2041547 A1 DE 2041547A1 DE 19702041547 DE19702041547 DE 19702041547 DE 2041547 A DE2041547 A DE 2041547A DE 2041547 A1 DE2041547 A1 DE 2041547A1
- Authority
- DE
- Germany
- Prior art keywords
- anthraquinone
- approx
- acid
- sulfonic acid
- disulfonic
- 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 11
- 150000004056 anthraquinones Chemical class 0.000 claims description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 15
- 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 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 238000006277 sulfonation reaction Methods 0.000 claims description 9
- 150000002739 metals Chemical class 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 7
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- 101150003085 Pdcl gene Proteins 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 150000002941 palladium compounds Chemical class 0.000 claims 1
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 10
- -1 B. as Co (OH) Chemical compound 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- MMNWSHJJPDXKCH-UHFFFAOYSA-N 9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MMNWSHJJPDXKCH-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- PTKWYSNDTXDBIZ-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2-disulfonic acid Chemical class C1=CC=C2C(=O)C3=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C3C(=O)C2=C1 PTKWYSNDTXDBIZ-UHFFFAOYSA-N 0.000 description 4
- IJNPIHLZSZCGOC-UHFFFAOYSA-N 9,10-dioxoanthracene-1,8-disulfonic acid Chemical compound O=C1C2=CC=CC(S(O)(=O)=O)=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O IJNPIHLZSZCGOC-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- OZTBHAGJSKTDGM-UHFFFAOYSA-N 9,10-dioxoanthracene-1,5-disulfonic acid Chemical compound O=C1C=2C(S(=O)(=O)O)=CC=CC=2C(=O)C2=C1C=CC=C2S(O)(=O)=O OZTBHAGJSKTDGM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- SROYVYGZVXMVOA-UHFFFAOYSA-N 9,10-dioxoanthracene-1,6-disulfonic acid Chemical compound O=C1C2=CC(S(=O)(=O)O)=CC=C2C(=O)C2=C1C=CC=C2S(O)(=O)=O SROYVYGZVXMVOA-UHFFFAOYSA-N 0.000 description 1
- VNIFUVUQZVMDER-UHFFFAOYSA-N 9,10-dioxoanthracene-1,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 VNIFUVUQZVMDER-UHFFFAOYSA-N 0.000 description 1
- 229910003771 Gold(I) chloride Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- MSSUFHMGCXOVBZ-UHFFFAOYSA-N anthraquinone-2,6-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MSSUFHMGCXOVBZ-UHFFFAOYSA-N 0.000 description 1
- QZPSXPBJTPJTSZ-UHFFFAOYSA-N aqua regia Chemical compound Cl.O[N+]([O-])=O QZPSXPBJTPJTSZ-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- XWVKTOHUMPLABF-UHFFFAOYSA-N thallium(3+) Chemical class [Tl+3] XWVKTOHUMPLABF-UHFFFAOYSA-N 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/33—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of six-membered aromatic rings being part of condensed ring systems
- C07C309/38—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of six-membered aromatic rings being part of condensed ring systems formed by at least three rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702041547 DE2041547A1 (de) | 1970-08-21 | 1970-08-21 | Verfahren zur Herstellung von Anthrachinon-alpha-sulfonsaeuren |
| NL7111395A NL7111395A (https=) | 1970-08-21 | 1971-08-18 | |
| IT27645/71A IT941698B (it) | 1970-08-21 | 1971-08-19 | Processo per la produzione di acidi antrachinon alfa solfonici |
| FR7130407A FR2104592A5 (https=) | 1970-08-21 | 1971-08-20 | |
| BE771579A BE771579A (fr) | 1970-08-21 | 1971-08-20 | Procede de production d'acides anthraquinone-alpha-sulfoniques |
| GB3919571A GB1314120A (en) | 1970-08-21 | 1971-08-20 | Process for the production of anthraquinone-alpha-sulphonic acid |
| US00173658A US3763191A (en) | 1970-08-21 | 1971-08-20 | Process for the production of anthraquinone-alpha-sulphonic acids |
| ES394402A ES394402A1 (es) | 1970-08-21 | 1971-08-20 | Procedimiento para la produccion de acidos antraquinona - alfa - sulfonicos. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702041547 DE2041547A1 (de) | 1970-08-21 | 1970-08-21 | Verfahren zur Herstellung von Anthrachinon-alpha-sulfonsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2041547A1 true DE2041547A1 (de) | 1972-02-24 |
Family
ID=5780355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702041547 Pending DE2041547A1 (de) | 1970-08-21 | 1970-08-21 | Verfahren zur Herstellung von Anthrachinon-alpha-sulfonsaeuren |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3763191A (https=) |
| BE (1) | BE771579A (https=) |
| DE (1) | DE2041547A1 (https=) |
| ES (1) | ES394402A1 (https=) |
| FR (1) | FR2104592A5 (https=) |
| GB (1) | GB1314120A (https=) |
| IT (1) | IT941698B (https=) |
| NL (1) | NL7111395A (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4711743A (en) * | 1987-01-21 | 1987-12-08 | 501 China Technical Consultants, Inc. | Process for producing anthraquinone-1-sulphonic acid by sulphonation with palladium catalyst |
| US4942251A (en) * | 1988-01-15 | 1990-07-17 | China Technical Consultants, Inc. | Process for producing α-anthraquinonesulfonic acids and recovering the catalyst used therein |
-
1970
- 1970-08-21 DE DE19702041547 patent/DE2041547A1/de active Pending
-
1971
- 1971-08-18 NL NL7111395A patent/NL7111395A/xx unknown
- 1971-08-19 IT IT27645/71A patent/IT941698B/it active
- 1971-08-20 GB GB3919571A patent/GB1314120A/en not_active Expired
- 1971-08-20 BE BE771579A patent/BE771579A/xx unknown
- 1971-08-20 FR FR7130407A patent/FR2104592A5/fr not_active Expired
- 1971-08-20 US US00173658A patent/US3763191A/en not_active Expired - Lifetime
- 1971-08-20 ES ES394402A patent/ES394402A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES394402A1 (es) | 1974-01-01 |
| US3763191A (en) | 1973-10-02 |
| NL7111395A (https=) | 1972-02-23 |
| GB1314120A (en) | 1973-04-18 |
| FR2104592A5 (https=) | 1972-04-14 |
| IT941698B (it) | 1973-03-10 |
| BE771579A (fr) | 1971-12-31 |
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