DE2222857A1 - Verfahren zur herstellung von 1aminoanthrachinonen - Google Patents
Verfahren zur herstellung von 1aminoanthrachinonenInfo
- Publication number
- DE2222857A1 DE2222857A1 DE19722222857 DE2222857A DE2222857A1 DE 2222857 A1 DE2222857 A1 DE 2222857A1 DE 19722222857 DE19722222857 DE 19722222857 DE 2222857 A DE2222857 A DE 2222857A DE 2222857 A1 DE2222857 A1 DE 2222857A1
- Authority
- DE
- Germany
- Prior art keywords
- carboxamide
- parts
- reaction
- anthraquinone
- alkali
- 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 20
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 60
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 239000000243 solution Substances 0.000 claims description 38
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 30
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 22
- QNLRSUPDYDUZSS-UHFFFAOYSA-N 9,10-dioxoanthracene-1-carboxamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(=O)N QNLRSUPDYDUZSS-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Chemical group 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 claims description 8
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 150000003857 carboxamides Chemical class 0.000 claims description 7
- 230000015556 catabolic process Effects 0.000 claims description 7
- 238000006731 degradation reaction Methods 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 5
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 5
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- ORQYPOUSZINNCB-UHFFFAOYSA-N potassium;hypobromite Chemical compound [K+].Br[O-] ORQYPOUSZINNCB-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 125000005521 carbonamide group Chemical group 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 12
- 229920000768 polyamine Polymers 0.000 description 12
- -1 amino compound Chemical class 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- QQOBTPNGSQEDAS-UHFFFAOYSA-N 1-amino-2-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(Cl)=C2N QQOBTPNGSQEDAS-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CBZDQIZUPFQSGF-UHFFFAOYSA-N NC(C(C(C(C1=CC=CC=C11)=O)=C(C=C2)C1=O)=C2Cl)=O Chemical compound NC(C(C(C(C1=CC=CC=C11)=O)=C(C=C2)C1=O)=C2Cl)=O CBZDQIZUPFQSGF-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000000630 rising effect Effects 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- RBGUKBSLNOTVCD-UHFFFAOYSA-N 1-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C RBGUKBSLNOTVCD-UHFFFAOYSA-N 0.000 description 2
- POPBYCBXVLHSKO-UHFFFAOYSA-N 9,10-dioxoanthracene-1-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(=O)O POPBYCBXVLHSKO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000012063 pure reaction product Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CXTPIHZYOGDSLV-UHFFFAOYSA-N 1-bromoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Br CXTPIHZYOGDSLV-UHFFFAOYSA-N 0.000 description 1
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 description 1
- AXFMHJRIYPZHDA-UHFFFAOYSA-N 3-chloro-9,10-dioxoanthracene-1-carboxamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(Cl)C=C2C(=O)N AXFMHJRIYPZHDA-UHFFFAOYSA-N 0.000 description 1
- LLSVGXGSYBLMNY-UHFFFAOYSA-N 9,10-dioxoanthracene-1-carbonyl chloride Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(=O)Cl LLSVGXGSYBLMNY-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 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
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B64—AIRCRAFT; AVIATION; COSMONAUTICS
- B64C—AEROPLANES; HELICOPTERS
- B64C27/00—Rotorcraft; Rotors peculiar thereto
- B64C27/04—Helicopters
- B64C27/12—Rotor drives
- B64C27/16—Drive of rotors by means, e.g. propellers, mounted on rotor blades
- B64C27/18—Drive of rotors by means, e.g. propellers, mounted on rotor blades the means being jet-reaction apparatus
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Aviation & Aerospace Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722222857 DE2222857A1 (de) | 1972-05-10 | 1972-05-10 | Verfahren zur herstellung von 1aminoanthrachinonen |
| CH645973A CH579025A5 (enrdf_load_stackoverflow) | 1972-05-10 | 1973-05-07 | |
| GB2212673A GB1420366A (en) | 1972-05-10 | 1973-05-09 | Manufacture of 1-aminoanthraquinones |
| IT4986273A IT985040B (it) | 1972-05-10 | 1973-05-09 | Procedimento per la produzione di i amminoantrachinoni |
| JP5081473A JPS4961233A (enrdf_load_stackoverflow) | 1972-05-10 | 1973-05-09 | |
| FR7316948A FR2184078B1 (enrdf_load_stackoverflow) | 1972-05-10 | 1973-05-10 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722222857 DE2222857A1 (de) | 1972-05-10 | 1972-05-10 | Verfahren zur herstellung von 1aminoanthrachinonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2222857A1 true DE2222857A1 (de) | 1973-11-22 |
Family
ID=5844577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722222857 Pending DE2222857A1 (de) | 1972-05-10 | 1972-05-10 | Verfahren zur herstellung von 1aminoanthrachinonen |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4961233A (enrdf_load_stackoverflow) |
| CH (1) | CH579025A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2222857A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2184078B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1420366A (enrdf_load_stackoverflow) |
| IT (1) | IT985040B (enrdf_load_stackoverflow) |
-
1972
- 1972-05-10 DE DE19722222857 patent/DE2222857A1/de active Pending
-
1973
- 1973-05-07 CH CH645973A patent/CH579025A5/xx not_active IP Right Cessation
- 1973-05-09 IT IT4986273A patent/IT985040B/it active
- 1973-05-09 GB GB2212673A patent/GB1420366A/en not_active Expired
- 1973-05-09 JP JP5081473A patent/JPS4961233A/ja active Pending
- 1973-05-10 FR FR7316948A patent/FR2184078B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1420366A (en) | 1976-01-07 |
| IT985040B (it) | 1974-11-30 |
| FR2184078B1 (enrdf_load_stackoverflow) | 1978-06-30 |
| FR2184078A1 (enrdf_load_stackoverflow) | 1973-12-21 |
| CH579025A5 (enrdf_load_stackoverflow) | 1976-08-31 |
| JPS4961233A (enrdf_load_stackoverflow) | 1974-06-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHN | Withdrawal |