WO2002004116A1 - Procede de preparation d'un catalyseur d'epoxydation - Google Patents
Procede de preparation d'un catalyseur d'epoxydation Download PDFInfo
- Publication number
- WO2002004116A1 WO2002004116A1 PCT/EP2001/008008 EP0108008W WO0204116A1 WO 2002004116 A1 WO2002004116 A1 WO 2002004116A1 EP 0108008 W EP0108008 W EP 0108008W WO 0204116 A1 WO0204116 A1 WO 0204116A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- catalyst
- catalyst system
- salt
- solvent
- organic solvent
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract 21
- 238000006735 epoxidation reaction Methods 0.000 title claims abstract 4
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract 13
- 239000003381 stabilizer Substances 0.000 claims abstract 10
- 150000003839 salts Chemical class 0.000 claims abstract 9
- 229910052751 metal Inorganic materials 0.000 claims abstract 7
- 239000002184 metal Substances 0.000 claims abstract 7
- 239000003960 organic solvent Substances 0.000 claims abstract 6
- 239000002904 solvent Substances 0.000 claims abstract 6
- 150000001336 alkenes Chemical class 0.000 claims abstract 4
- 230000002209 hydrophobic effect Effects 0.000 claims abstract 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims abstract 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract 2
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract 2
- 150000004706 metal oxides Chemical class 0.000 claims abstract 2
- 230000003647 oxidation Effects 0.000 claims abstract 2
- 238000007254 oxidation reaction Methods 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000002245 particle Substances 0.000 claims 2
- 230000001681 protective effect Effects 0.000 claims 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 claims 1
- CGYGETOMCSJHJU-UHFFFAOYSA-N 2-chloronaphthalene Chemical compound C1=CC=CC2=CC(Cl)=CC=C21 CGYGETOMCSJHJU-UHFFFAOYSA-N 0.000 claims 1
- 101710134784 Agnoprotein Proteins 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 239000005639 Lauric acid Substances 0.000 claims 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims 1
- 229920002873 Polyethylenimine Polymers 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 150000004996 alkyl benzenes Chemical class 0.000 claims 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000002790 naphthalenes Chemical class 0.000 claims 1
- 229940078552 o-xylene Drugs 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical group [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 1
- -1 glycol monoalkylethers Chemical class 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 238000010518 undesired secondary reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
- C07D301/10—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase with catalysts containing silver or gold
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/48—Silver or gold
- B01J23/50—Silver
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/20—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state
- B01J35/23—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state in a colloidal state
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Epoxy Compounds (AREA)
- Catalysts (AREA)
Abstract
La présente invention concerne un procédé de préparation d'un système de catalyse stabilisé. Selon ledit procédé, dans un solvant organique sensiblement anhydre, stable à l'oxydation, est réduit un sel d'un métal du premier, deuxième ou huitième sous-groupe, soluble dans ledit solvant, en présence d'un stabilisant au moyen d'un agent de réduction, pour donner un métal colloïdal. De manière alternative, le sel de métal peut être hydrolysé en présence d'un stabilisant avec de l'eau pour donner un oxyde métallique colloïdal. Le solvant est choisi parmi les hydrocarbures aliphatiques, aromatiques, aliphatiques nitrés et aromatiques nitrés, aliphatiques halogénés et aromatiques halogénés, et en tant que stabilisant est utilisé un stabilisant hydrophobe soluble dans ledit solvant. La sélection du solvant permet d'éviter dans une large mesure les réactions secondaires non désirées telles que la formation de sous-produits tels que les glycols et les glycol monoalkyl éthers. Le système de catalyse ainsi obtenu, ou le catalyseur pouvant être isolé à partir de ce système, peuvent être utilisés pour l'époxydation d'alcènes en solution. Dans un mode de réalisation particulièrement préféré de l'invention, un système de catalyse contenant de l'argent colloïdal est utilisé pour l'époxydation d'éthylène.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2001285830A AU2001285830A1 (en) | 2000-07-11 | 2001-07-11 | Method for producing an epoxidation catalyst |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10033572A DE10033572A1 (de) | 2000-07-11 | 2000-07-11 | Verfahren zur Herstellung eines Epoxidierungskatalysators |
| DE10033572.1 | 2000-07-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2002004116A1 true WO2002004116A1 (fr) | 2002-01-17 |
Family
ID=7648481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2001/008008 WO2002004116A1 (fr) | 2000-07-11 | 2001-07-11 | Procede de preparation d'un catalyseur d'epoxydation |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU2001285830A1 (fr) |
| DE (1) | DE10033572A1 (fr) |
| WO (1) | WO2002004116A1 (fr) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5147841A (en) * | 1990-11-23 | 1992-09-15 | The United States Of America As Represented By The United States Department Of Energy | Method for the preparation of metal colloids in inverse micelles and product preferred by the method |
| EP0916403A2 (fr) * | 1997-11-05 | 1999-05-19 | Director-General Of The Agency Of Industrial Science And Technology | Catalyseur pour l'oxydation partielle d'un hydrocarbure et procédé de préparation d'un composé organique contenant de l'oxygène |
| CN1217328A (zh) * | 1997-11-13 | 1999-05-26 | 中国石油化工总公司 | 加压三相系环氧乙烷合成工艺 |
| JPH11253802A (ja) * | 1998-03-13 | 1999-09-21 | Nippon Shokubai Co Ltd | 液相用エチレン酸化触媒および液相でのエチレンオキシドの製造方法 |
| EP1005907A1 (fr) * | 1998-02-24 | 2000-06-07 | Japan as represented by Director-General, Agency of Industrial Science and Technology | Catalyseur d'oxydation partielle d'hydrocarbure insature |
-
2000
- 2000-07-11 DE DE10033572A patent/DE10033572A1/de not_active Withdrawn
-
2001
- 2001-07-11 WO PCT/EP2001/008008 patent/WO2002004116A1/fr active Application Filing
- 2001-07-11 AU AU2001285830A patent/AU2001285830A1/en not_active Abandoned
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5147841A (en) * | 1990-11-23 | 1992-09-15 | The United States Of America As Represented By The United States Department Of Energy | Method for the preparation of metal colloids in inverse micelles and product preferred by the method |
| EP0916403A2 (fr) * | 1997-11-05 | 1999-05-19 | Director-General Of The Agency Of Industrial Science And Technology | Catalyseur pour l'oxydation partielle d'un hydrocarbure et procédé de préparation d'un composé organique contenant de l'oxygène |
| CN1217328A (zh) * | 1997-11-13 | 1999-05-26 | 中国石油化工总公司 | 加压三相系环氧乙烷合成工艺 |
| EP1005907A1 (fr) * | 1998-02-24 | 2000-06-07 | Japan as represented by Director-General, Agency of Industrial Science and Technology | Catalyseur d'oxydation partielle d'hydrocarbure insature |
| JPH11253802A (ja) * | 1998-03-13 | 1999-09-21 | Nippon Shokubai Co Ltd | 液相用エチレン酸化触媒および液相でのエチレンオキシドの製造方法 |
Non-Patent Citations (2)
| Title |
|---|
| DATABASE WPI Derwent World Patents Index; AN 1999-459238, XP002182599, "Pressure triphase series ethylene oxide process adopt fine particle catalyst three phase bed reactor" * |
| PATENT ABSTRACTS OF JAPAN vol. 1999, no. 14 22 December 1999 (1999-12-22) * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE10033572A1 (de) | 2002-01-24 |
| AU2001285830A1 (en) | 2002-01-21 |
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