CA2214017A1 - Procede de synthese de 2-ethyl-anthraquinone - Google Patents
Procede de synthese de 2-ethyl-anthraquinone Download PDFInfo
- Publication number
- CA2214017A1 CA2214017A1 CA002214017A CA2214017A CA2214017A1 CA 2214017 A1 CA2214017 A1 CA 2214017A1 CA 002214017 A CA002214017 A CA 002214017A CA 2214017 A CA2214017 A CA 2214017A CA 2214017 A1 CA2214017 A1 CA 2214017A1
- Authority
- CA
- Canada
- Prior art keywords
- ebb
- acid
- temperature
- oleum
- solid
- 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.)
- Abandoned
Links
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000007787 solid Substances 0.000 claims abstract description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 21
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 17
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 15
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 12
- 235000011149 sulphuric acid Nutrition 0.000 claims abstract description 4
- JZFDKGFWNSQAHU-UHFFFAOYSA-N 2-(4-ethylbenzoyl)benzoic acid Chemical compound C1=CC(CC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JZFDKGFWNSQAHU-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 20
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002244 precipitate Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 12
- 238000007363 ring formation reaction Methods 0.000 claims description 12
- 239000012429 reaction media Substances 0.000 claims description 7
- 239000003637 basic solution Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 239000008139 complexing agent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 150000002978 peroxides Chemical class 0.000 claims 1
- 239000003039 volatile agent Substances 0.000 claims 1
- 238000000859 sublimation Methods 0.000 abstract description 5
- 230000008022 sublimation Effects 0.000 abstract description 3
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 4
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229940116269 uric acid Drugs 0.000 description 4
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- FDSYTWVNUJTPMA-UHFFFAOYSA-N 2-[3,9-bis(carboxymethyl)-3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-yl]acetic acid Chemical compound C1N(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC2=CC=CC1=N2 FDSYTWVNUJTPMA-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 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 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/675—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having three rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR95/02988 | 1995-03-15 | ||
| FR9502988A FR2731705B1 (fr) | 1995-03-15 | 1995-03-15 | Procede de synthese de 2-ethyl-anthraquinone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2214017A1 true CA2214017A1 (fr) | 1996-09-19 |
Family
ID=9477040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002214017A Abandoned CA2214017A1 (fr) | 1995-03-15 | 1996-03-12 | Procede de synthese de 2-ethyl-anthraquinone |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0815069A1 (cs) |
| JP (1) | JPH11501650A (cs) |
| KR (1) | KR980700950A (cs) |
| AU (1) | AU5008396A (cs) |
| BR (1) | BR9607208A (cs) |
| CA (1) | CA2214017A1 (cs) |
| CZ (1) | CZ269997A3 (cs) |
| FR (1) | FR2731705B1 (cs) |
| HU (1) | HUP9801205A2 (cs) |
| NO (1) | NO973604L (cs) |
| PL (1) | PL322204A1 (cs) |
| WO (1) | WO1996028410A1 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN119368119B (zh) * | 2024-12-27 | 2025-04-18 | 山东门捷新材料股份有限公司 | 一种2-乙基蒽醌合成产线 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2496097A1 (fr) * | 1980-12-16 | 1982-06-18 | Ugine Kuhlmann | Procede pour la preparation de l'anthraquinone et de ses derives substitues |
| US4404140A (en) * | 1981-10-26 | 1983-09-13 | E. I. Du Pont De Nemours And Company | Manufacture of alkylanthraquinones |
| FR2532303A1 (fr) * | 1982-09-01 | 1984-03-02 | Ugine Kuhlmann | Procede de decomposition d'un complexe d'acide ortho-benzoyl-benzoique, de fluorure d'hydrogene et de trifluorure de bore |
| FR2543544B1 (fr) * | 1983-03-30 | 1986-01-17 | Ugine Kuhlmann | Procede de decomposition d'un complexe d'acide orthobenzoyl-benzoique, de fluorure d'hydrogene et de trifluorure de bore |
-
1995
- 1995-03-15 FR FR9502988A patent/FR2731705B1/fr not_active Expired - Fee Related
-
1996
- 1996-03-12 HU HU9801205A patent/HUP9801205A2/hu unknown
- 1996-03-12 EP EP96906818A patent/EP0815069A1/fr not_active Withdrawn
- 1996-03-12 CZ CZ972699A patent/CZ269997A3/cs unknown
- 1996-03-12 WO PCT/FR1996/000383 patent/WO1996028410A1/fr not_active Ceased
- 1996-03-12 CA CA002214017A patent/CA2214017A1/fr not_active Abandoned
- 1996-03-12 AU AU50083/96A patent/AU5008396A/en not_active Abandoned
- 1996-03-12 JP JP8527334A patent/JPH11501650A/ja active Pending
- 1996-03-12 KR KR1019970704539A patent/KR980700950A/ko not_active Withdrawn
- 1996-03-12 BR BR9607208A patent/BR9607208A/pt not_active Application Discontinuation
- 1996-03-12 PL PL96322204A patent/PL322204A1/xx unknown
-
1997
- 1997-08-05 NO NO973604A patent/NO973604L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9801205A2 (hu) | 1998-08-28 |
| WO1996028410A1 (fr) | 1996-09-19 |
| KR980700950A (ko) | 1998-04-30 |
| FR2731705B1 (fr) | 1997-04-30 |
| BR9607208A (pt) | 1997-11-11 |
| CZ269997A3 (cs) | 1998-02-18 |
| FR2731705A1 (fr) | 1996-09-20 |
| MX9706937A (es) | 1997-11-29 |
| NO973604D0 (no) | 1997-08-05 |
| AU5008396A (en) | 1996-10-02 |
| PL322204A1 (en) | 1998-01-19 |
| NO973604L (no) | 1997-08-05 |
| JPH11501650A (ja) | 1999-02-09 |
| EP0815069A1 (fr) | 1998-01-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |