DE2247347C3 - Verfahren zur herstellung von reiner 1-amino-4-nitroanthrachinon- 2-carbonsaeure - Google Patents
Verfahren zur herstellung von reiner 1-amino-4-nitroanthrachinon- 2-carbonsaeureInfo
- Publication number
- DE2247347C3 DE2247347C3 DE19722247347 DE2247347A DE2247347C3 DE 2247347 C3 DE2247347 C3 DE 2247347C3 DE 19722247347 DE19722247347 DE 19722247347 DE 2247347 A DE2247347 A DE 2247347A DE 2247347 C3 DE2247347 C3 DE 2247347C3
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acid
- amino
- parts
- nitroanthraquinone
- acid
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 17
- SSLUBNFUCQBYTP-UHFFFAOYSA-N 1-amino-4-nitro-9,10-dioxoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C([N+]([O-])=O)=CC(C(O)=O)=C2N SSLUBNFUCQBYTP-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 238000001556 precipitation Methods 0.000 claims description 10
- 239000002244 precipitate Substances 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 7
- 229910017604 nitric acid Inorganic materials 0.000 claims description 7
- 239000012670 alkaline solution Substances 0.000 claims description 6
- 238000006396 nitration reaction Methods 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
- 230000020477 pH reduction Effects 0.000 claims description 2
- ASDLSKCKYGVMAI-UHFFFAOYSA-N 9,10-dioxoanthracene-2-carboxylic acid Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)O)=CC=C3C(=O)C2=C1 ASDLSKCKYGVMAI-UHFFFAOYSA-N 0.000 claims 2
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims 1
- 150000001844 chromium Chemical class 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 230000001066 destructive effect Effects 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- 239000010865 sewage Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 6
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 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 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- -1 m-nitrobenzenesulfonate peroxydisulfate Chemical compound 0.000 description 3
- 230000000802 nitrating effect Effects 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ONMOULMPIIOVTQ-UHFFFAOYSA-N 98-47-5 Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 235000019395 ammonium persulphate Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940079826 hydrogen sulfite Drugs 0.000 description 1
- MCUDGYVHPADJBD-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium sulfuric acid Chemical compound OS(O)(=O)=O.O[Cr](=O)(=O)O[Cr](O)(=O)=O MCUDGYVHPADJBD-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005406 washing Methods 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)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722247347 DE2247347C3 (de) | 1972-09-27 | 1972-09-27 | Verfahren zur herstellung von reiner 1-amino-4-nitroanthrachinon- 2-carbonsaeure |
| US399174A US3886188A (en) | 1972-09-27 | 1973-09-20 | Production of pure 1-amino-4-nitroanthraquinone-2-carboxylic acid |
| CH1364073A CH580060A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-09-27 | 1973-09-24 | |
| FR7334360A FR2200248B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-09-27 | 1973-09-25 | |
| GB4507773A GB1435823A (en) | 1972-09-27 | 1973-09-26 | Production of pure 1-amino-4-nitroanthraquinone-2-carboxylic acid |
| IT52770/73A IT997591B (it) | 1972-09-27 | 1973-09-26 | Procedimento per la produzione di acido i ammino 4 nitroantrachi non 2 carbossilico puro |
| JP10805573A JPS533389B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-09-27 | 1973-09-27 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722247347 DE2247347C3 (de) | 1972-09-27 | 1972-09-27 | Verfahren zur herstellung von reiner 1-amino-4-nitroanthrachinon- 2-carbonsaeure |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2247347A1 DE2247347A1 (de) | 1974-03-28 |
| DE2247347B2 DE2247347B2 (de) | 1976-07-15 |
| DE2247347C3 true DE2247347C3 (de) | 1977-02-17 |
Family
ID=5857510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722247347 Expired DE2247347C3 (de) | 1972-09-27 | 1972-09-27 | Verfahren zur herstellung von reiner 1-amino-4-nitroanthrachinon- 2-carbonsaeure |
Country Status (7)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114105791A (zh) * | 2021-12-16 | 2022-03-01 | 烟台丰鲁精细化工有限责任公司 | 一种1，4-二氨基蒽醌-2-羧酸十氢-2-萘酯的新型合成方法 |
| FR3131779B1 (fr) | 2022-01-13 | 2023-12-29 | Psa Automobiles Sa | Surveillance de l’isolement électrique d’une ligne de recharge d’une batterie principale d’un véhicule |
-
1972
- 1972-09-27 DE DE19722247347 patent/DE2247347C3/de not_active Expired
-
1973
- 1973-09-20 US US399174A patent/US3886188A/en not_active Expired - Lifetime
- 1973-09-24 CH CH1364073A patent/CH580060A5/xx not_active IP Right Cessation
- 1973-09-25 FR FR7334360A patent/FR2200248B1/fr not_active Expired
- 1973-09-26 IT IT52770/73A patent/IT997591B/it active
- 1973-09-26 GB GB4507773A patent/GB1435823A/en not_active Expired
- 1973-09-27 JP JP10805573A patent/JPS533389B2/ja not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| Nichts Ermittelt. * |
Also Published As
| Publication number | Publication date |
|---|---|
| IT997591B (it) | 1975-12-30 |
| GB1435823A (en) | 1976-05-19 |
| FR2200248A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-04-19 |
| FR2200248B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-11-10 |
| JPS4969651A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-07-05 |
| US3886188A (en) | 1975-05-27 |
| DE2247347A1 (de) | 1974-03-28 |
| DE2247347B2 (de) | 1976-07-15 |
| CH580060A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-30 |
| JPS533389B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-02-06 |
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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 | ||
| 8339 | Ceased/non-payment of the annual fee |