DE2628725C2 - Verfahren zur Herstellung von 2-tert.-alkylsubstituierten Anthrachinonen - Google Patents
Verfahren zur Herstellung von 2-tert.-alkylsubstituierten AnthrachinonenInfo
- Publication number
- DE2628725C2 DE2628725C2 DE2628725A DE2628725A DE2628725C2 DE 2628725 C2 DE2628725 C2 DE 2628725C2 DE 2628725 A DE2628725 A DE 2628725A DE 2628725 A DE2628725 A DE 2628725A DE 2628725 C2 DE2628725 C2 DE 2628725C2
- Authority
- DE
- Germany
- Prior art keywords
- tert
- catalyst
- mol
- yield
- alkyl
- 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 35
- 150000004056 anthraquinones Chemical class 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000003054 catalyst Substances 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 claims description 9
- -1 diphenylmethane compound Chemical class 0.000 claims description 9
- 229910001935 vanadium oxide Inorganic materials 0.000 claims description 9
- 239000012808 vapor phase Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 30
- 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 description 15
- 239000000203 mixture Substances 0.000 description 15
- 238000007254 oxidation reaction Methods 0.000 description 13
- 230000003647 oxidation Effects 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- 230000003197 catalytic effect Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- PQTAUFTUHHRKSS-UHFFFAOYSA-N 1-benzyl-2-methylbenzene Chemical compound CC1=CC=CC=C1CC1=CC=CC=C1 PQTAUFTUHHRKSS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- WUKWGUZTPMOXOW-UHFFFAOYSA-N 2-(2-methylbutan-2-yl)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)CC)=CC=C3C(=O)C2=C1 WUKWGUZTPMOXOW-UHFFFAOYSA-N 0.000 description 5
- IJVJGNLTJANDLJ-UHFFFAOYSA-N 2-benzyl-1-methyl-4-(2-methylbutan-2-yl)benzene Chemical compound CCC(C)(C)C1=CC=C(C)C(CC=2C=CC=CC=2)=C1 IJVJGNLTJANDLJ-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 150000001555 benzenes Chemical class 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000002736 metal compounds Chemical class 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 4
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 4
- KQHWOQVALZANKQ-UHFFFAOYSA-N 1-benzyl-2-methyl-4-(2-methylbutan-2-yl)benzene Chemical compound CC1=CC(C(C)(C)CC)=CC=C1CC1=CC=CC=C1 KQHWOQVALZANKQ-UHFFFAOYSA-N 0.000 description 3
- ISTKBJBIDSJWAT-UHFFFAOYSA-N 1-tert-butyl-4-(3-phenylpropyl)benzene Chemical compound C1=CC(C(C)(C)C)=CC=C1CCCC1=CC=CC=C1 ISTKBJBIDSJWAT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- DAWXHFHHIIWPCU-UHFFFAOYSA-N 1-benzyl-4-tert-butyl-2-methylbenzene Chemical compound CC1=CC(C(C)(C)C)=CC=C1CC1=CC=CC=C1 DAWXHFHHIIWPCU-UHFFFAOYSA-N 0.000 description 2
- KAGHIKANRQOZDX-UHFFFAOYSA-N 2-benzyl-4-tert-butylbenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C(CC=2C=CC=CC=2)=C1 KAGHIKANRQOZDX-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229910010413 TiO 2 Inorganic materials 0.000 description 2
- COQLPRJCUIATTQ-UHFFFAOYSA-N Uranyl acetate Chemical compound O.O.O=[U]=O.CC(O)=O.CC(O)=O COQLPRJCUIATTQ-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- AIYUHDOJVYHVIT-UHFFFAOYSA-M caesium chloride Chemical compound [Cl-].[Cs+] AIYUHDOJVYHVIT-UHFFFAOYSA-M 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 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
- 239000002699 waste material Substances 0.000 description 2
- KPTQJZTWCJLSBB-UHFFFAOYSA-N 1-(2-methylbutan-2-yl)-3-(3-phenylpropyl)benzene Chemical compound CCC(C)(C)C1=CC=CC(CCCC=2C=CC=CC=2)=C1 KPTQJZTWCJLSBB-UHFFFAOYSA-N 0.000 description 1
- USOGEHKPOBWTBL-UHFFFAOYSA-N 1-(2-methylbutan-2-yl)-4-(3-phenylpropyl)benzene Chemical compound C1=CC(C(C)(C)CC)=CC=C1CCCC1=CC=CC=C1 USOGEHKPOBWTBL-UHFFFAOYSA-N 0.000 description 1
- LUMWLXHMQVOIPO-UHFFFAOYSA-N 1-methyl-2-[[4-(2-methylbutan-2-yl)phenyl]methyl]benzene Chemical compound C1=CC(C(C)(C)CC)=CC=C1CC1=CC=CC=C1C LUMWLXHMQVOIPO-UHFFFAOYSA-N 0.000 description 1
- WPFPGNBLDSASGF-UHFFFAOYSA-N 1-tert-butyl-3-(3-phenylpropyl)benzene Chemical compound CC(C)(C)C1=CC=CC(CCCC=2C=CC=CC=2)=C1 WPFPGNBLDSASGF-UHFFFAOYSA-N 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- PVHUGSHJCGXHNU-UHFFFAOYSA-N 2-[(4-pentylphenyl)methyl]benzaldehyde Chemical compound C1=CC(CCCCC)=CC=C1CC1=CC=CC=C1C=O PVHUGSHJCGXHNU-UHFFFAOYSA-N 0.000 description 1
- LJBGURBFHJJQQU-UHFFFAOYSA-N 2-benzyl-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(CC=2C=CC=CC=2)=C1 LJBGURBFHJJQQU-UHFFFAOYSA-N 0.000 description 1
- YARZNRAVRMLTKF-UHFFFAOYSA-N 2-benzyl-4-tert-butyl-1-methylbenzene Chemical compound CC1=CC=C(C(C)(C)C)C=C1CC1=CC=CC=C1 YARZNRAVRMLTKF-UHFFFAOYSA-N 0.000 description 1
- DHARILAASAAGJJ-UHFFFAOYSA-N 4-benzylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1CC1=CC=CC=C1 DHARILAASAAGJJ-UHFFFAOYSA-N 0.000 description 1
- OTXINXDGSUFPNU-UHFFFAOYSA-N 4-tert-butylbenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C=C1 OTXINXDGSUFPNU-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- RTXUQSXTAPNBER-UHFFFAOYSA-N [O-2].[U+6].[O-2].[V+5] Chemical compound [O-2].[U+6].[O-2].[V+5] RTXUQSXTAPNBER-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000006840 diphenylmethane group Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002468 indanes Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CRNIHJHMEQZAAS-UHFFFAOYSA-N tert-amyl chloride Chemical compound CCC(C)(C)Cl CRNIHJHMEQZAAS-UHFFFAOYSA-N 0.000 description 1
- 150000003476 thallium compounds Chemical class 0.000 description 1
- 229910003438 thallium oxide Inorganic materials 0.000 description 1
- HQOJMTATBXYHNR-UHFFFAOYSA-M thallium(I) acetate Chemical compound [Tl+].CC([O-])=O HQOJMTATBXYHNR-UHFFFAOYSA-M 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 150000003671 uranium compounds Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50079281A JPS523047A (en) | 1975-06-25 | 1975-06-25 | Preparation of di-(t-alkyl) anthraquinones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2628725A1 DE2628725A1 (de) | 1976-12-30 |
| DE2628725C2 true DE2628725C2 (de) | 1986-06-12 |
Family
ID=13685469
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2628725A Expired DE2628725C2 (de) | 1975-06-25 | 1976-06-25 | Verfahren zur Herstellung von 2-tert.-alkylsubstituierten Anthrachinonen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4036861A (OSRAM) |
| JP (1) | JPS523047A (OSRAM) |
| DE (1) | DE2628725C2 (OSRAM) |
| FR (1) | FR2317267A1 (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2804417C2 (de) * | 1978-02-02 | 1986-07-24 | Bergwerksverband Gmbh, 4300 Essen | Verfahren zur Herstellung von Anthrachinon |
| JPS5823859B2 (ja) * | 1979-03-08 | 1983-05-18 | 三菱瓦斯化学株式会社 | ２↓−タ↓−シヤリ↓−アルキル置換アンスラキノンの製造方法 |
| US4215063A (en) * | 1979-05-03 | 1980-07-29 | American Cyanamid Company | Oxidation catalyst and use in the production of anthraquinone |
| US4405523A (en) * | 1982-03-24 | 1983-09-20 | Standard Oil Company (Indiana) | Process for preparation of benzophenone, anthraquinone and O-dibenzoylbenzene |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2050798C3 (de) * | 1970-10-16 | 1975-07-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Anthrachinon |
| CH560664A5 (OSRAM) * | 1970-06-10 | 1975-04-15 | Basf Ag |
-
1975
- 1975-06-25 JP JP50079281A patent/JPS523047A/ja active Granted
-
1976
- 1976-06-17 US US05/696,835 patent/US4036861A/en not_active Expired - Lifetime
- 1976-06-24 FR FR7619264A patent/FR2317267A1/fr active Granted
- 1976-06-25 DE DE2628725A patent/DE2628725C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2317267A1 (fr) | 1977-02-04 |
| DE2628725A1 (de) | 1976-12-30 |
| JPS523047A (en) | 1977-01-11 |
| FR2317267B1 (OSRAM) | 1980-08-01 |
| US4036861A (en) | 1977-07-19 |
| JPS5516494B2 (OSRAM) | 1980-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: HENKEL, G., DR.PHIL. KERN, R., DIPL.-ING. FEILER, |
|
| 8128 | New person/name/address of the agent |
Representative=s name: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT. HAENZ |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |