DE2050798C3 - Verfahren zur Herstellung von Anthrachinon - Google Patents
Verfahren zur Herstellung von AnthrachinonInfo
- Publication number
- DE2050798C3 DE2050798C3 DE19702050798 DE2050798A DE2050798C3 DE 2050798 C3 DE2050798 C3 DE 2050798C3 DE 19702050798 DE19702050798 DE 19702050798 DE 2050798 A DE2050798 A DE 2050798A DE 2050798 C3 DE2050798 C3 DE 2050798C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- radicals
- radical
- methyl
- oxo
- 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
- 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 9
- 150000004056 anthraquinones Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000002468 indanes Chemical class 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 description 41
- -1 aliphatic radical Chemical class 0.000 description 17
- 239000007858 starting material Substances 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 125000004043 oxo group Chemical group O=* 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229910052787 antimony Inorganic materials 0.000 description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 3
- CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 2
- PQTAUFTUHHRKSS-UHFFFAOYSA-N 1-benzyl-2-methylbenzene Chemical compound CC1=CC=CC=C1CC1=CC=CC=C1 PQTAUFTUHHRKSS-UHFFFAOYSA-N 0.000 description 2
- YSPDISPRPJFBCV-UHFFFAOYSA-N 1-phenyl-1,2,3,4-tetrahydronaphthalene Chemical compound C12=CC=CC=C2CCCC1C1=CC=CC=C1 YSPDISPRPJFBCV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 2
- 229910052716 thallium Inorganic materials 0.000 description 2
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical class [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- UCJJALAVFHJTAQ-UHFFFAOYSA-N 1-ethyl-2-methyl-4-phenyl-1,2,3,4-tetrahydronaphthalene Chemical compound C12=CC=CC=C2C(CC)C(C)CC1C1=CC=CC=C1 UCJJALAVFHJTAQ-UHFFFAOYSA-N 0.000 description 1
- JJUWUZOXEIZYON-UHFFFAOYSA-N 1-methyl-3-phenyl-1h-indene Chemical compound C12=CC=CC=C2C(C)C=C1C1=CC=CC=C1 JJUWUZOXEIZYON-UHFFFAOYSA-N 0.000 description 1
- VNAFWALXWOAPCK-UHFFFAOYSA-N 1-phenyl-2,3-dihydro-1h-indene Chemical compound C1CC2=CC=CC=C2C1C1=CC=CC=C1 VNAFWALXWOAPCK-UHFFFAOYSA-N 0.000 description 1
- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- KQECTNBWHRPLLP-UHFFFAOYSA-N 2-bromo-3-phenyl-2,3-dihydroinden-1-one Chemical compound C12=CC=CC=C2C(=O)C(Br)C1C1=CC=CC=C1 KQECTNBWHRPLLP-UHFFFAOYSA-N 0.000 description 1
- FCWYHPKEZUEUBA-UHFFFAOYSA-N 2-ethyl-3-phenyl-2,3-dihydroinden-1-one Chemical compound C12=CC=CC=C2C(=O)C(CC)C1C1=CC=CC=C1 FCWYHPKEZUEUBA-UHFFFAOYSA-N 0.000 description 1
- LKBQPEWBQILOBX-UHFFFAOYSA-N 2-methyl-3,3-diphenylprop-2-enoic acid Chemical compound C=1C=CC=CC=1C(=C(C(O)=O)C)C1=CC=CC=C1 LKBQPEWBQILOBX-UHFFFAOYSA-N 0.000 description 1
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940054021 anxiolytics diphenylmethane derivative Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000010285 flame spraying Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000007750 plasma spraying Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/20—Vanadium, niobium or tantalum
- B01J23/22—Vanadium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702050798 DE2050798C3 (de) | 1970-10-16 | 1970-10-16 | Verfahren zur Herstellung von Anthrachinon |
| CH534571A CH560664A5 (enrdf_load_stackoverflow) | 1970-06-10 | 1971-04-13 | |
| RO6681171A RO59478A (enrdf_load_stackoverflow) | 1970-06-10 | 1971-05-06 | |
| GB1715971A GB1346944A (en) | 1970-06-10 | 1971-05-26 | Production of anthraquinone |
| IT5072171A IT994017B (it) | 1970-06-10 | 1971-05-31 | Procedimento per la produzione di antrachinone |
| CA114591A CA932725A (en) | 1970-06-10 | 1971-06-01 | Production of anthraquinone |
| SU1670031A SU460616A3 (ru) | 1970-06-10 | 1971-06-08 | Способ получени антрахинона |
| HUBA002596 HU163476B (enrdf_load_stackoverflow) | 1970-06-10 | 1971-06-09 | |
| PL17422971A PL90620B1 (enrdf_load_stackoverflow) | 1970-10-16 | 1971-06-09 | |
| ES392097A ES392097A2 (es) | 1970-06-10 | 1971-06-09 | Procedimiento para la obtencion de antraquinona. |
| AT392572A AT315161B (de) | 1970-10-16 | 1971-06-09 | Verfahren zur Herstellung von Anthrachinon |
| NL7107911A NL7107911A (en) | 1969-06-16 | 1971-06-09 | Anthraquinone - by gas phase catalytic oxidation of indanes - or diphenyl methane dervs |
| FR7120877A FR2094160B2 (enrdf_load_stackoverflow) | 1970-06-10 | 1971-06-09 | |
| PL14869771A PL83415B3 (en) | 1970-06-10 | 1971-06-09 | Production of anthraquinone[gb1346944a] |
| CS550872A CS167317B4 (enrdf_load_stackoverflow) | 1970-10-16 | 1971-06-10 | |
| BE768344A BE768344R (fr) | 1970-06-10 | 1971-06-10 | Procede de preparation |
| CS425571A CS167316B4 (enrdf_load_stackoverflow) | 1970-06-10 | 1971-06-10 | |
| AU80393/75A AU8039375A (en) | 1970-06-10 | 1975-04-22 | Production of anthraquinone |
| JP5899878A JPS5436244A (en) | 1970-06-10 | 1978-05-19 | Production of anthraquinone |
| JP7707078A JPS5416461A (en) | 1970-06-10 | 1978-06-27 | Production of anthraquinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702050798 DE2050798C3 (de) | 1970-10-16 | 1970-10-16 | Verfahren zur Herstellung von Anthrachinon |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2050798A1 DE2050798A1 (de) | 1972-04-20 |
| DE2050798B2 DE2050798B2 (de) | 1974-06-27 |
| DE2050798C3 true DE2050798C3 (de) | 1975-07-03 |
Family
ID=5785272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702050798 Expired DE2050798C3 (de) | 1969-06-16 | 1970-10-16 | Verfahren zur Herstellung von Anthrachinon |
Country Status (4)
| Country | Link |
|---|---|
| AT (1) | AT315161B (enrdf_load_stackoverflow) |
| CS (1) | CS167317B4 (enrdf_load_stackoverflow) |
| DE (1) | DE2050798C3 (enrdf_load_stackoverflow) |
| PL (1) | PL90620B1 (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2442911C2 (de) * | 1974-09-07 | 1983-08-25 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Anthrachinon |
| JPS523047A (en) * | 1975-06-25 | 1977-01-11 | Mitsubishi Gas Chem Co Inc | Preparation of di-(t-alkyl) anthraquinones |
-
1970
- 1970-10-16 DE DE19702050798 patent/DE2050798C3/de not_active Expired
-
1971
- 1971-06-09 PL PL17422971A patent/PL90620B1/pl unknown
- 1971-06-09 AT AT392572A patent/AT315161B/de not_active IP Right Cessation
- 1971-06-10 CS CS550872A patent/CS167317B4/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT315161B (de) | 1974-05-10 |
| DE2050798B2 (de) | 1974-06-27 |
| DE2050798A1 (de) | 1972-04-20 |
| PL90620B1 (enrdf_load_stackoverflow) | 1977-01-31 |
| CS167317B4 (enrdf_load_stackoverflow) | 1976-04-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| AG | Has addition no. |
Ref document number: 2430567 Country of ref document: DE |
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| AG | Has addition no. |
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| 8330 | Complete disclaimer |