DE2130699A1 - Verfahren zur Herstellung von Anthrachinonderivaten - Google Patents
Verfahren zur Herstellung von AnthrachinonderivatenInfo
- Publication number
- DE2130699A1 DE2130699A1 DE19712130699 DE2130699A DE2130699A1 DE 2130699 A1 DE2130699 A1 DE 2130699A1 DE 19712130699 DE19712130699 DE 19712130699 DE 2130699 A DE2130699 A DE 2130699A DE 2130699 A1 DE2130699 A1 DE 2130699A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- amino
- preparation
- carboxylic acid
- solution
- 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 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- 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 description 2
- 150000004056 anthraquinones Chemical class 0.000 title description 2
- 239000007800 oxidant agent Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- MMKNBFSDCOALQO-UHFFFAOYSA-N 1-amino-9,10-dioxoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(C(O)=O)=C2N MMKNBFSDCOALQO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000012286 potassium permanganate Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002152 aqueous-organic solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- HKUBCGKNVQMKBM-UHFFFAOYSA-N 1-amino-9,10-dioxo-2h-anthracene-1-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)(C(O)=O)CC=C2 HKUBCGKNVQMKBM-UHFFFAOYSA-N 0.000 description 1
- DVVGIUUJYPYENY-UHFFFAOYSA-N 1-methylpyridin-2-one Chemical compound CN1C=CC=CC1=O DVVGIUUJYPYENY-UHFFFAOYSA-N 0.000 description 1
- OQVYMXCRDHDTTH-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)-2-[4-(diethoxyphosphorylmethyl)pyridin-2-yl]pyridine Chemical compound CCOP(=O)(OCC)CC1=CC=NC(C=2N=CC=C(CP(=O)(OCC)OCC)C=2)=C1 OQVYMXCRDHDTTH-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- -1 dioxane Chemical class 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 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
- C09B1/22—Dyes with unsubstituted amino groups
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 |
|---|---|---|---|
| CH954670A CH532022A (de) | 1970-06-24 | 1970-06-24 | Verfahren zur Herstellung von Anthrachinonderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2130699A1 true DE2130699A1 (de) | 1971-12-30 |
Family
ID=4353113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712130699 Pending DE2130699A1 (de) | 1970-06-24 | 1971-06-21 | Verfahren zur Herstellung von Anthrachinonderivaten |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3836548A (enExample) |
| BE (1) | BE768918A (enExample) |
| CA (1) | CA948188A (enExample) |
| CH (1) | CH532022A (enExample) |
| DE (1) | DE2130699A1 (enExample) |
| FR (1) | FR2096085A5 (enExample) |
| GB (1) | GB1336921A (enExample) |
| NL (1) | NL7108676A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3925060A1 (de) * | 1989-07-28 | 1991-01-31 | Basf Ag | Verfahren zur herstellung von 1-amino-2-carboxyanthrachinonen |
-
1970
- 1970-06-24 CH CH954670A patent/CH532022A/de not_active IP Right Cessation
-
1971
- 1971-06-08 FR FR7120786A patent/FR2096085A5/fr not_active Expired
- 1971-06-16 CA CA115,772A patent/CA948188A/en not_active Expired
- 1971-06-16 GB GB2810271A patent/GB1336921A/en not_active Expired
- 1971-06-17 US US00154169A patent/US3836548A/en not_active Expired - Lifetime
- 1971-06-21 DE DE19712130699 patent/DE2130699A1/de active Pending
- 1971-06-23 BE BE768918A patent/BE768918A/xx unknown
- 1971-06-23 NL NL7108676A patent/NL7108676A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1336921A (en) | 1973-11-14 |
| CH532022A (de) | 1972-12-31 |
| NL7108676A (enExample) | 1971-12-28 |
| CA948188A (en) | 1974-05-28 |
| US3836548A (en) | 1974-09-17 |
| FR2096085A5 (enExample) | 1972-02-11 |
| BE768918A (fr) | 1971-12-23 |
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