CH619203A5 - Process for the concentration of haloanthraquinones - Google Patents
Process for the concentration of haloanthraquinones Download PDFInfo
- Publication number
- CH619203A5 CH619203A5 CH1557875A CH1557875A CH619203A5 CH 619203 A5 CH619203 A5 CH 619203A5 CH 1557875 A CH1557875 A CH 1557875A CH 1557875 A CH1557875 A CH 1557875A CH 619203 A5 CH619203 A5 CH 619203A5
- Authority
- CH
- Switzerland
- Prior art keywords
- mixtures
- halogenanthraquinone
- mixture
- column
- dichloroanthraquinone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 34
- 239000000203 mixture Substances 0.000 claims description 100
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 claims description 60
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 claims description 23
- 238000010992 reflux Methods 0.000 claims description 22
- 239000012535 impurity Substances 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 238000002844 melting Methods 0.000 claims description 14
- 230000008018 melting Effects 0.000 claims description 14
- DCKYBPULWXTYJB-UHFFFAOYSA-N 1,2,3-trichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(Cl)C(Cl)=C2Cl DCKYBPULWXTYJB-UHFFFAOYSA-N 0.000 claims description 12
- 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 11
- 238000004821 distillation Methods 0.000 claims description 11
- 239000000155 melt Substances 0.000 claims description 10
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 claims description 8
- 239000002351 wastewater Substances 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000005292 vacuum distillation Methods 0.000 claims description 3
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 claims description 2
- 229940005991 chloric acid Drugs 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000004508 fractional distillation Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 53
- 238000009835 boiling Methods 0.000 description 41
- 239000010409 thin film Substances 0.000 description 29
- VBQNYYXVDQUKIU-UHFFFAOYSA-N 1,8-dichloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(Cl)=C2C(=O)C2=C1C=CC=C2Cl VBQNYYXVDQUKIU-UHFFFAOYSA-N 0.000 description 28
- 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 25
- 150000004056 anthraquinones Chemical class 0.000 description 24
- PLUFITIFLBGFPN-UHFFFAOYSA-N 1,2-dichloroanthracene-9,10-dione Chemical class C1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3C(=O)C2=C1 PLUFITIFLBGFPN-UHFFFAOYSA-N 0.000 description 14
- 238000010438 heat treatment Methods 0.000 description 13
- ASMKLYHDMPMGHC-UHFFFAOYSA-N 1,7-dichloroanthracene-9,10-dione Chemical compound C1=CC(Cl)=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 ASMKLYHDMPMGHC-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000012546 transfer Methods 0.000 description 11
- 239000012065 filter cake Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 9
- MQIUMARJCOGCIM-UHFFFAOYSA-N 1,5-dichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2Cl MQIUMARJCOGCIM-UHFFFAOYSA-N 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- ISPZGSLKFNLVQT-UHFFFAOYSA-N 1,4,5-trichloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC(Cl)=C2C(=O)C2=C1C=CC=C2Cl ISPZGSLKFNLVQT-UHFFFAOYSA-N 0.000 description 4
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 210000003298 dental enamel Anatomy 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- DOBUSJIVSSJEDA-UHFFFAOYSA-L 1,3-dioxa-2$l^{6}-thia-4-mercuracyclobutane 2,2-dioxide Chemical compound [Hg+2].[O-]S([O-])(=O)=O DOBUSJIVSSJEDA-UHFFFAOYSA-L 0.000 description 3
- GCDPTNVMLMOCEH-UHFFFAOYSA-N 1,4,6-trichloroanthracene-9,10-dione Chemical compound C1=CC(Cl)=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1Cl GCDPTNVMLMOCEH-UHFFFAOYSA-N 0.000 description 3
- MBIJFIUDKPXMAV-UHFFFAOYSA-N 1,8-dinitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC([N+]([O-])=O)=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] MBIJFIUDKPXMAV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 3
- 238000006887 Ullmann reaction Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000011552 falling film Substances 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 229910000370 mercury sulfate Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000012856 packing Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- -1 Halogen anthraquinones Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- KJGPMAHVCDFRBN-UHFFFAOYSA-N 2,6-dichloroanthracene-9,10-dione Chemical compound ClC1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 KJGPMAHVCDFRBN-UHFFFAOYSA-N 0.000 description 1
- HQUNBWGQFXPVES-UHFFFAOYSA-N 2,7-dichloroanthracene-9,10-dione Chemical compound C1=C(Cl)C=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 HQUNBWGQFXPVES-UHFFFAOYSA-N 0.000 description 1
- OZTBHAGJSKTDGM-UHFFFAOYSA-N 9,10-dioxoanthracene-1,5-disulfonic acid Chemical compound O=C1C=2C(S(=O)(=O)O)=CC=CC=2C(=O)C2=C1C=CC=C2S(O)(=O)=O OZTBHAGJSKTDGM-UHFFFAOYSA-N 0.000 description 1
- MMNWSHJJPDXKCH-UHFFFAOYSA-N 9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 MMNWSHJJPDXKCH-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- UEQDQOLEMQBKOM-UHFFFAOYSA-N ClC1=CC=2C(C3=CC=CC=C3C(C2C=C1)=O)=O.ClC1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O Chemical compound ClC1=CC=2C(C3=CC=CC=C3C(C2C=C1)=O)=O.ClC1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O UEQDQOLEMQBKOM-UHFFFAOYSA-N 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004338 hydroxy anthraquinones Chemical class 0.000 description 1
- 239000010842 industrial wastewater Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 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 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
- B01D3/148—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step in combination with at least one evaporator
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742458022 DE2458022C3 (de) | 1974-12-07 | 1974-12-07 | Verfahren zur Gewinnung von reinen Chloranthrachinonen |
| DE19752531929 DE2531929A1 (de) | 1975-07-17 | 1975-07-17 | Verfahren zur anreicherung von halogenanthrachinonen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH619203A5 true CH619203A5 (en) | 1980-09-15 |
Family
ID=25768077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1557875A CH619203A5 (en) | 1974-12-07 | 1975-12-01 | Process for the concentration of haloanthraquinones |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS591248B2 (en, 2012) |
| AT (1) | AT340402B (en, 2012) |
| BR (1) | BR7508056A (en, 2012) |
| CA (1) | CA1068234A (en, 2012) |
| CH (1) | CH619203A5 (en, 2012) |
| DD (1) | DD124114A5 (en, 2012) |
| DK (1) | DK551575A (en, 2012) |
| ES (1) | ES443239A1 (en, 2012) |
| FR (1) | FR2293412A1 (en, 2012) |
| GB (1) | GB1492137A (en, 2012) |
| IT (1) | IT1052516B (en, 2012) |
| LU (1) | LU73943A1 (en, 2012) |
| NL (1) | NL7514239A (en, 2012) |
| SU (1) | SU598555A3 (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2637689C3 (de) * | 1976-08-21 | 1980-09-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur Reinigungsc^nlellender organischer Produkte |
| CH628607A5 (en) * | 1976-12-02 | 1982-03-15 | Bayer Ag | Process for preparing chloroanthraquinones |
| US4206130A (en) * | 1977-05-10 | 1980-06-03 | Bayer Aktiengesellschaft | Process for the preparation of 1,5-dichloroanthraquinone |
| CH653666A5 (de) * | 1983-06-23 | 1986-01-15 | Ciba Geigy Ag | Verfahren zur herstellung von bromanthrachinonen. |
-
1975
- 1975-10-24 GB GB4382075A patent/GB1492137A/en not_active Expired
- 1975-12-01 CH CH1557875A patent/CH619203A5/de not_active IP Right Cessation
- 1975-12-04 BR BR7508056A patent/BR7508056A/pt unknown
- 1975-12-04 SU SU752194657A patent/SU598555A3/ru active
- 1975-12-05 FR FR7537336A patent/FR2293412A1/fr active Granted
- 1975-12-05 LU LU73943A patent/LU73943A1/xx unknown
- 1975-12-05 ES ES443239A patent/ES443239A1/es not_active Expired
- 1975-12-05 CA CA241,187A patent/CA1068234A/en not_active Expired
- 1975-12-05 NL NL7514239A patent/NL7514239A/xx unknown
- 1975-12-05 JP JP14404675A patent/JPS591248B2/ja not_active Expired
- 1975-12-05 IT IT5254875A patent/IT1052516B/it active
- 1975-12-05 AT AT927075A patent/AT340402B/de not_active IP Right Cessation
- 1975-12-05 DD DD18992475A patent/DD124114A5/xx unknown
- 1975-12-05 DK DK551575A patent/DK551575A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK551575A (da) | 1976-06-08 |
| ES443239A1 (es) | 1977-09-16 |
| DD124114A5 (en, 2012) | 1977-02-02 |
| FR2293412B1 (en, 2012) | 1979-06-01 |
| BR7508056A (pt) | 1976-08-24 |
| CA1068234A (en) | 1979-12-18 |
| LU73943A1 (en, 2012) | 1976-11-11 |
| ATA927075A (de) | 1977-04-15 |
| NL7514239A (nl) | 1976-06-09 |
| IT1052516B (it) | 1981-07-20 |
| SU598555A3 (ru) | 1978-03-15 |
| FR2293412A1 (fr) | 1976-07-02 |
| JPS5182250A (ja) | 1976-07-19 |
| AT340402B (de) | 1977-12-12 |
| JPS591248B2 (ja) | 1984-01-11 |
| GB1492137A (en) | 1977-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |