DE2541663A1 - Verfahren zur herstellung von aminoanthrachinonen - Google Patents
Verfahren zur herstellung von aminoanthrachinonenInfo
- Publication number
- DE2541663A1 DE2541663A1 DE19752541663 DE2541663A DE2541663A1 DE 2541663 A1 DE2541663 A1 DE 2541663A1 DE 19752541663 DE19752541663 DE 19752541663 DE 2541663 A DE2541663 A DE 2541663A DE 2541663 A1 DE2541663 A1 DE 2541663A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- sulfone
- sulfones
- parts
- tetramethylene sulfone
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 18
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 9
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 claims description 8
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 7
- -1 alkylene sulfones Chemical class 0.000 claims description 6
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical class C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000003457 sulfones Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 238000007098 aminolysis reaction Methods 0.000 description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 4
- ATIYVSUEHXWMKF-UHFFFAOYSA-N 1-(propan-2-ylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(C)C ATIYVSUEHXWMKF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- VDPDRYUUTXEEIE-UHFFFAOYSA-N bis(methylsulfonyl)methane Chemical compound CS(=O)(=O)CS(C)(=O)=O VDPDRYUUTXEEIE-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- SVTDYSXXLJYUTM-UHFFFAOYSA-N disperse red 9 Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC SVTDYSXXLJYUTM-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- UMFJAHHVKNCGLG-UHFFFAOYSA-N n-Nitrosodimethylamine Chemical compound CN(C)N=O UMFJAHHVKNCGLG-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 1
- XVMVHWDCRFNPQR-UHFFFAOYSA-N 1,5-dinitroanthracene-9,10-dione Chemical compound O=C1C=2C([N+](=O)[O-])=CC=CC=2C(=O)C2=C1C=CC=C2[N+]([O-])=O XVMVHWDCRFNPQR-UHFFFAOYSA-N 0.000 description 1
- ZNUGRMBAZNMDEK-UHFFFAOYSA-N 1-(2-methylpropylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NCC(C)C ZNUGRMBAZNMDEK-UHFFFAOYSA-N 0.000 description 1
- ZCVSDPUSEUOUHQ-UHFFFAOYSA-N 1-(benzenesulfonyl)-2,4-dimethylbenzene Chemical compound CC1=CC(C)=CC=C1S(=O)(=O)C1=CC=CC=C1 ZCVSDPUSEUOUHQ-UHFFFAOYSA-N 0.000 description 1
- ZWIBACOXZKQWIP-UHFFFAOYSA-N 1-(dicyclohexylamino)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1N(C1CCCCC1)C1CCCCC1 ZWIBACOXZKQWIP-UHFFFAOYSA-N 0.000 description 1
- QAXHKRXSWCEOMO-UHFFFAOYSA-N 1-(diethylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N(CC)CC QAXHKRXSWCEOMO-UHFFFAOYSA-N 0.000 description 1
- BRPOLULJMDJSOG-UHFFFAOYSA-N 1-(ethylsulfonylmethylsulfonyl)ethane Chemical compound CCS(=O)(=O)CS(=O)(=O)CC BRPOLULJMDJSOG-UHFFFAOYSA-N 0.000 description 1
- NJAKRNRJVHIIDT-UHFFFAOYSA-N 1-ethylsulfonyl-2-methylpropane Chemical compound CCS(=O)(=O)CC(C)C NJAKRNRJVHIIDT-UHFFFAOYSA-N 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- QRXUXNUNFHPWLQ-UHFFFAOYSA-N 1-methylsulfonylbutane Chemical compound CCCCS(C)(=O)=O QRXUXNUNFHPWLQ-UHFFFAOYSA-N 0.000 description 1
- YBJCDTIWNDBNTM-UHFFFAOYSA-N 1-methylsulfonylethane Chemical compound CCS(C)(=O)=O YBJCDTIWNDBNTM-UHFFFAOYSA-N 0.000 description 1
- QAPSIUMUNHNUPW-UHFFFAOYSA-N 1-methylsulfonylpropane Chemical compound CCCS(C)(=O)=O QAPSIUMUNHNUPW-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
- UVGFYTMWSGOJRW-UHFFFAOYSA-N 2-methoxy-1-nitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C(OC)=CC=C3C(=O)C2=C1 UVGFYTMWSGOJRW-UHFFFAOYSA-N 0.000 description 1
- ILJDSLLXQSVCFV-UHFFFAOYSA-N 2-methylsulfonylpentane Chemical compound CCCC(C)S(C)(=O)=O ILJDSLLXQSVCFV-UHFFFAOYSA-N 0.000 description 1
- VTWYQAQIXXAXOR-UHFFFAOYSA-N 2-methylsulfonylpropane Chemical compound CC(C)S(C)(=O)=O VTWYQAQIXXAXOR-UHFFFAOYSA-N 0.000 description 1
- ZDULHUHNYHJYKA-UHFFFAOYSA-N 2-propan-2-ylsulfonylpropane Chemical compound CC(C)S(=O)(=O)C(C)C ZDULHUHNYHJYKA-UHFFFAOYSA-N 0.000 description 1
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 1
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 1
- CAOPOEWNJFGVEK-UHFFFAOYSA-N 5-nitro-9,10-dioxoanthracene-2-sulfonic acid Chemical compound O=C1C2=CC(S(=O)(=O)O)=CC=C2C(=O)C2=C1C=CC=C2[N+]([O-])=O CAOPOEWNJFGVEK-UHFFFAOYSA-N 0.000 description 1
- LDAXDTROVOYFJX-UHFFFAOYSA-N 9,10-dioxo-8-(propan-2-ylamino)anthracene-2-sulfonic acid Chemical compound O=C1C2=CC=C(S(O)(=O)=O)C=C2C(=O)C2=C1C=CC=C2NC(C)C LDAXDTROVOYFJX-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- OFZCIYFFPZCNJE-UHFFFAOYSA-N carisoprodol Chemical compound NC(=O)OCC(C)(CCC)COC(=O)NC(C)C OFZCIYFFPZCNJE-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- CESKLHVYGRFMFP-UHFFFAOYSA-N sulfonmethane Chemical compound CCS(=O)(=O)C(C)(C)S(=O)(=O)CC CESKLHVYGRFMFP-UHFFFAOYSA-N 0.000 description 1
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 1
- CFRVORMUGQWQNZ-UHFFFAOYSA-N thiepane 1,1-dioxide Chemical compound O=S1(=O)CCCCCC1 CFRVORMUGQWQNZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
- C09B1/30—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated
- C09B1/303—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated only sulfonated in the anthracene nucleus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1279374A CH592716A5 (en, 2012) | 1974-09-20 | 1974-09-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2541663A1 true DE2541663A1 (de) | 1976-04-08 |
Family
ID=4386459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752541663 Withdrawn DE2541663A1 (de) | 1974-09-20 | 1975-09-18 | Verfahren zur herstellung von aminoanthrachinonen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4076735A (en, 2012) |
| BE (1) | BE833605A (en, 2012) |
| CH (1) | CH592716A5 (en, 2012) |
| DE (1) | DE2541663A1 (en, 2012) |
| GB (1) | GB1512577A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0859032A1 (de) * | 1997-02-13 | 1998-08-19 | Bayer Ag | Verbrückte Anthrachinone |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2730342C3 (de) * | 1976-07-07 | 1980-12-18 | Ciba-Geigy Ag, Basel (Schweiz) | Verfahren zur Herstellung von Anthrachinonverbindungen |
| US4195012A (en) * | 1978-03-29 | 1980-03-25 | American Cyanamid Company | Process for preparing 2-chloro-1-methylaminoanthraquinone and plastics containing the same |
| EP0005206B1 (de) * | 1978-04-28 | 1981-04-01 | Ciba-Geigy Ag | Verfahren zur Herstellung von 1,4-Diaminoanthrachinon-2-carbonsäure |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE126542C (en, 2012) * | ||||
| US2273966A (en) * | 1939-10-26 | 1942-02-24 | Du Pont | Process for preparing 1-amino-5-nitro-anthraquinone |
| US2738354A (en) * | 1951-01-24 | 1956-03-13 | Ciba Ltd | Process of making amino-anthraquinones |
| US3417090A (en) * | 1965-09-15 | 1968-12-17 | Bayer Ag | Reduction of nitro compounds to amines |
| CH573464A5 (en, 2012) * | 1972-10-05 | 1976-03-15 | Ciba Geigy Ag | |
| DE2300592A1 (de) * | 1973-01-08 | 1974-07-11 | Bayer Ag | Nitroanthrachinone |
| BE812616A (fr) * | 1973-03-22 | 1974-09-23 | Procede de production de la 1-amino-anthraquinone | |
| DE2409542A1 (de) * | 1974-02-28 | 1975-09-11 | Bayer Ag | Verfahren zur herstellung von aminoanthrachinonen |
| DD126542A1 (en, 2012) | 1975-12-23 | 1977-07-20 |
-
1974
- 1974-09-20 CH CH1279374A patent/CH592716A5/xx not_active IP Right Cessation
-
1975
- 1975-09-12 US US05/612,811 patent/US4076735A/en not_active Expired - Lifetime
- 1975-09-18 DE DE19752541663 patent/DE2541663A1/de not_active Withdrawn
- 1975-09-19 BE BE160190A patent/BE833605A/xx unknown
- 1975-09-19 GB GB38609/75A patent/GB1512577A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0859032A1 (de) * | 1997-02-13 | 1998-08-19 | Bayer Ag | Verbrückte Anthrachinone |
Also Published As
| Publication number | Publication date |
|---|---|
| BE833605A (fr) | 1976-03-19 |
| US4076735A (en) | 1978-02-28 |
| GB1512577A (en) | 1978-06-01 |
| CH592716A5 (en, 2012) | 1977-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |