BE846038A - Acides anthraquinone-disulfoniques mixtes - Google Patents
Acides anthraquinone-disulfoniques mixtesInfo
- Publication number
- BE846038A BE846038A BE170489A BE170489A BE846038A BE 846038 A BE846038 A BE 846038A BE 170489 A BE170489 A BE 170489A BE 170489 A BE170489 A BE 170489A BE 846038 A BE846038 A BE 846038A
- Authority
- BE
- Belgium
- Prior art keywords
- anthraquinone
- substitution
- emi
- acids
- methylanthraquinone
- Prior art date
Links
- 239000002253 acid Substances 0.000 title description 9
- 150000007513 acids Chemical class 0.000 title description 7
- 238000000034 method Methods 0.000 claims description 37
- 238000006467 substitution reaction Methods 0.000 claims description 20
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 claims description 18
- 150000004056 anthraquinones Chemical class 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- PTKWYSNDTXDBIZ-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2-disulfonic acid Chemical class C1=CC=C2C(=O)C3=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C3C(=O)C2=C1 PTKWYSNDTXDBIZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000006277 sulfonation reaction Methods 0.000 claims description 11
- 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 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 7
- WRGJTTAISWFMCK-UHFFFAOYSA-N 9,10-dioxo-2,3-disulfoanthracene-1-carboxylic acid Chemical class C1=CC=C2C(=O)C3=CC(S(O)(=O)=O)=C(S(O)(=O)=O)C(C(=O)O)=C3C(=O)C2=C1 WRGJTTAISWFMCK-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 5
- 239000012670 alkaline solution Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims 1
- 230000001172 regenerating effect Effects 0.000 claims 1
- 229910052720 vanadium Chemical class 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical class [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 241001664469 Tibicina haematodes Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- -1 disulfoanthraquinone-dicarboxylic acids Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- GNRPVZNNVOGXHD-UHFFFAOYSA-N 1,2-dimethylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(C)C(C)=CC=C3C(=O)C2=C1 GNRPVZNNVOGXHD-UHFFFAOYSA-N 0.000 description 2
- KIJPZYXCIHZVGP-UHFFFAOYSA-N 2,3-dimethylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(C)C(C)=C2 KIJPZYXCIHZVGP-UHFFFAOYSA-N 0.000 description 2
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 2
- OKONMFPEKSWGEU-UHFFFAOYSA-N 9,10-dioxoanthracene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 OKONMFPEKSWGEU-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000009102 absorption Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000003034 coal gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- 150000003681 vanadium Chemical class 0.000 description 2
- ISQFYHBWKRJRKI-UHFFFAOYSA-N 1,3,5,7-tetramethylanthracene-9,10-dione Chemical compound CC1=CC(C)=C2C(=O)C3=CC(C)=CC(C)=C3C(=O)C2=C1 ISQFYHBWKRJRKI-UHFFFAOYSA-N 0.000 description 1
- BMTSXXTYUZQGBX-UHFFFAOYSA-N 1,3,6,8-tetramethylanthracene-9,10-dione Chemical compound C1=C(C)C=C2C(=O)C3=CC(C)=CC(C)=C3C(=O)C2=C1C BMTSXXTYUZQGBX-UHFFFAOYSA-N 0.000 description 1
- NBGHRJGIRMJVQI-UHFFFAOYSA-N 1,3,6-trimethylanthracene-9,10-dione Chemical compound C1=C(C)C=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1C NBGHRJGIRMJVQI-UHFFFAOYSA-N 0.000 description 1
- ADHYTCPJVXOAJX-UHFFFAOYSA-N 1,3-dimethylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(C)=C3C(=O)C2=C1 ADHYTCPJVXOAJX-UHFFFAOYSA-N 0.000 description 1
- NPOQVIYWUNAVCX-UHFFFAOYSA-N 1,7-dioxoanthracene-2,3-disulfonic acid Chemical compound O=C1C=CC2=CC3=CC(S(=O)(=O)O)=C(S(O)(=O)=O)C(=O)C3=CC2=C1 NPOQVIYWUNAVCX-UHFFFAOYSA-N 0.000 description 1
- HGOCIIJWUIKMNF-UHFFFAOYSA-N 1-(tert-butylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(C)(C)C HGOCIIJWUIKMNF-UHFFFAOYSA-N 0.000 description 1
- NMFBXBSNLQNQKL-UHFFFAOYSA-N 1-chloro-2-methylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(C)=CC=C3C(=O)C2=C1 NMFBXBSNLQNQKL-UHFFFAOYSA-N 0.000 description 1
- BGJQNPIOBWKQAW-UHFFFAOYSA-N 1-tert-butylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)(C)C BGJQNPIOBWKQAW-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
- QDXLTKIWHQNESJ-UHFFFAOYSA-N 2-(2-methylpropyl)anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CC(C)C)=CC=C3C(=O)C2=C1 QDXLTKIWHQNESJ-UHFFFAOYSA-N 0.000 description 1
- MCYPCBFOVKMNDW-UHFFFAOYSA-N 2-butan-2-ylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)CC)=CC=C3C(=O)C2=C1 MCYPCBFOVKMNDW-UHFFFAOYSA-N 0.000 description 1
- YQZHOBBQNFBTJE-UHFFFAOYSA-N 2-chloro-3-methylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(C)C(Cl)=C2 YQZHOBBQNFBTJE-UHFFFAOYSA-N 0.000 description 1
- FYJQJHDVUZCYTG-UHFFFAOYSA-N 2-chloro-6-methylanthracene-9,10-dione Chemical compound ClC1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 FYJQJHDVUZCYTG-UHFFFAOYSA-N 0.000 description 1
- NPOIYFMFHGQKIC-UHFFFAOYSA-N 2-chloro-9,10-dioxoanthracene-1-carboxylic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(Cl)=C2C(=O)O NPOIYFMFHGQKIC-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- BQUNPXRABCSKJZ-UHFFFAOYSA-N 2-propan-2-ylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3C(=O)C2=C1 BQUNPXRABCSKJZ-UHFFFAOYSA-N 0.000 description 1
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 description 1
- CWRYEKZIZYCTQE-UHFFFAOYSA-N 9,10-dioxo-3,6-disulfoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC=C(S(O)(=O)=O)C=C2C(=O)C2=C1C=C(C(=O)O)C(S(O)(=O)=O)=C2 CWRYEKZIZYCTQE-UHFFFAOYSA-N 0.000 description 1
- XHVUSKHNNYICSX-UHFFFAOYSA-N 9,10-dioxo-3,7-disulfoanthracene-2-carboxylic acid Chemical compound O=C1C2=CC(S(O)(=O)=O)=CC=C2C(=O)C2=C1C=C(C(=O)O)C(S(O)(=O)=O)=C2 XHVUSKHNNYICSX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052936 alkali metal sulfate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B17/00—Sulfur; Compounds thereof
- C01B17/02—Preparation of sulfur; Purification
- C01B17/04—Preparation of sulfur; Purification from gaseous sulfur compounds including gaseous sulfides
- C01B17/05—Preparation of sulfur; Purification from gaseous sulfur compounds including gaseous sulfides by wet processes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61291775A | 1975-09-12 | 1975-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE846038A true BE846038A (fr) | 1976-12-31 |
Family
ID=24455127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE170489A BE846038A (fr) | 1975-09-12 | 1976-09-10 | Acides anthraquinone-disulfoniques mixtes |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE846038A (enExample) |
| IN (1) | IN144387B (enExample) |
| ZA (1) | ZA765146B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2426081A1 (fr) * | 1978-05-19 | 1979-12-14 | Mitsui Toatsu Chemicals | Reactif d'oxydo-reduction pour un procede de desulfuration par voie humide et procede pour sa preparation |
| US4251492A (en) | 1978-06-07 | 1981-02-17 | Ciba-Geigy Corporation | Purification process |
-
1976
- 1976-05-27 ZA ZA765146A patent/ZA765146B/xx unknown
- 1976-08-30 IN IN1593/CAL/76A patent/IN144387B/en unknown
- 1976-09-10 BE BE170489A patent/BE846038A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2426081A1 (fr) * | 1978-05-19 | 1979-12-14 | Mitsui Toatsu Chemicals | Reactif d'oxydo-reduction pour un procede de desulfuration par voie humide et procede pour sa preparation |
| US4251492A (en) | 1978-06-07 | 1981-02-17 | Ciba-Geigy Corporation | Purification process |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA765146B (en) | 1977-08-31 |
| IN144387B (enExample) | 1978-04-29 |
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