WO1999028035A1 - Catalyseur a base de zeolite, son utilisation et procede d'epoxydation en presence de ce catalyseur - Google Patents
Catalyseur a base de zeolite, son utilisation et procede d'epoxydation en presence de ce catalyseur Download PDFInfo
- Publication number
- WO1999028035A1 WO1999028035A1 PCT/EP1998/007530 EP9807530W WO9928035A1 WO 1999028035 A1 WO1999028035 A1 WO 1999028035A1 EP 9807530 W EP9807530 W EP 9807530W WO 9928035 A1 WO9928035 A1 WO 9928035A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- zeolite
- catalyst
- equal
- support
- deposited
- Prior art date
Links
Classifications
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/024—Multiple impregnation or coating
- B01J37/0246—Coatings comprising a zeolite
-
- 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
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
Definitions
- Zeolite catalyst its use and epoxidation process in the presence of this catalyst
- the invention relates to a novel supported catalyst based on zeolite. It also relates to a method for producing such a catalyst and its use in chemical reactions in the liquid phase as the olefin epoxidation reaction under the action of hydrogen peroxide. It is known to use a zeolite as a catalyst in olefin epoxidation reactions.
- patent application EP 100119 discloses a process for the epoxidation of olefins by means of hydrogen peroxide in the presence of a synthetic zeolite containing titanium atoms. This synthetic zeolite containing titanium atoms is known under the name of titanium silicalite and abbreviated as TS-1.
- zeolites deactivate during use and that regeneration treatments must therefore be carried out regularly, generally by washing with solvents or by heating to restore their activity. It is important that the zeolite does not degrade under the conditions of regeneration. It is also known that the zeolites, and in particular the TS-1 obtained according to the process described in the patent application mentioned above, can consist of very fine particles which it is difficult to separate from the reaction mixture in order to effect them. regeneration. Furthermore, when the zeolites, and in particular the TS-1, consist of large grains, a significant decrease in the catalytic activity of this catalyst is observed on the one hand and poor resistance to attrition of the particles of somewhere else.
- the invention aims to remedy these drawbacks by providing a new catalyst of such shape that it is easy to separate from the reaction mixture to effect regeneration and which has good mechanical properties and high activity.
- the invention relates to a catalyst comprising a zeolite deposited on a support in the form of honeycombs.
- honeycomb shape is meant a shape made up of elements with a honeycomb structure, whatever the shape of the honeycombs.
- the catalyst according to the invention has a level of catalytic activity close to that of a fine powder and can be regenerated without significant loss of zeolite or of catalytic activity. In particular, it was -?
- the support in the form of honeycombs is made of an inert material, supporting the conditions of regeneration and on which it is possible to adhere the zeolite by means of a binder.
- silicas are well suited. It may for example be silicas combined with other magnesium, aluminum oxides and their mixtures.
- the support is preferably cordierite or mullite. Particular preference is shown for cordierite because it leads to better adhesion of the zeolite to the support.
- an oxidizing agent such as hydrogen peroxide
- mullite a preference is shown for mullite because it better resists such regeneration conditions which lead to acidification of the medium.
- cordierite can also be regenerated in the presence of an oxidizing agent provided that the pH is maintained, during regeneration, at a value of approximately 3 to 4.
- the honeycomb-shaped support is generally in the form of a cartridge comprising from 10 to 1200 cells per inch ⁇ (cpi ⁇ ).
- the number of cells is from 50 to 450 cpi ⁇ , for example from 70 to 400 cpi 2 .
- zeolite is meant a solid containing silica which has a microporous crystalline structure.
- the zeolite is advantageously free of aluminum.
- the zeolite may contain titanium.
- the zeolite according to the invention is a zeolite in which several silicon atoms have been replaced by titanium atoms.
- zeolites of the titanium silicalite type advantageously have a crystal structure of the ZSM-5, ZSM-11, MCM-41 or beta type. They preferably have an infrared absorption band at approximately 950-960 cm " ⁇ .
- Those corresponding to the formula xTi ⁇ 2 (lx) Si ⁇ 2 in which x is from 0.0001 to 0.5, preferably from 0.001 to 0.05 Materials of this type, known under the name of TS-1, have a microporous crystalline zeolitic structure analogous to that of zeolite ZSM-5. The properties and the main applications of these compounds are known (B.
- the zeolite content in the catalyst according to the invention expressed as a percentage by weight of zeolite in the catalyst is generally greater than or equal to 1% and less than or equal to 60%.
- the zeolite content is greater than or equal to 5% and less than or equal to 40%.
- the catalyst according to the invention withstands, during the catalyst conditioning or regeneration phases, dry heating (at 500 ° C. for example) or in the presence of solvent without significant loss of active elements.
- hydrogen peroxide used as an oxidizing reagent during synthesis or as a regenerating agent, does not cause significant damage to the catalyst either.
- the invention also relates to a method of manufacturing the catalyst described above.
- the zeolite is, in a first step, dispersed in a binder and the dispersion thus obtained is deposited by impregnation on a support in the form of honeycombs in a second step.
- the binder used is a silicon-based compound.
- colloidal silicas silica soles, silicates (for example tetraalkyl silicates) and silicone resins.
- colloidal silicas are preferred.
- qualities of colloidal silica may be suitable. They are characterized in particular by the size of the particles, by their specific surface, by their pH and by the nature of the counterion.
- the size of the colloidal silica particles is between 1 and 30 ⁇ m.
- the particle size is between 5 and 25 ⁇ m.
- a preference is marked for particles whose size is between 7 and 20 ⁇ m.
- the particle size is greater than or equal to 0.1 ⁇ m and less than or equal to 10 ⁇ m.
- the particle size is greater than or equal to 1 ⁇ m and less than or equal to 5 ⁇ m.
- Colloidal silicas can have an acidic or basic pH.
- the contr'ion is advantageously a chloride anion and / or the silica particles can be covered on the surface with a layer of alumina.
- the control is advantageously a sodium cation or a cation ammonium and / or superficial silicon atoms can be replaced by aluminum atoms.
- a dispersion of the zeolite in a binder is prepared, optionally with stirring.
- the weight ratio between the quantity of zeolite used and the quantity of binder can vary within a very large proportion. This ratio is generally less than or equal to 20 and greater than or equal to 0.1. Preferably, this ratio is less than or equal to 15 and greater than or equal to 0.5.
- a ratio close to 10 makes it possible to limit the amount of material to be deposited on the support in the form of honeycombs while fixing the desired amount of zeolite without however blocking the channels of the support.
- the amount of water in the dispersion is such that the dispersion contains at least 10 g of zeolite per 100 g of water.
- the amount of water is such that the dispersion contains at least 20 g of zeolite per 100 g of water. This concentration is generally less than or equal to 175 g of zeolite per 100 g of water.
- this concentration is less than 150 g of zeolite per 100 g of water. Particular preference is shown for a range of concentrations ranging from 50 to 90 g of zeolite per 100 g of water.
- the impregnation of the support in the form of honeycombs is generally done either by pouring the dispersion onto the support in the form of honeycombs, or by immersing the support in the dispersion. Generally, the impregnation step takes place at room temperature. After the impregnation step, the liquid adhering to the walls of the honeycombs can be expelled by a jet of compressed air to avoid clogging of the honeycomb channels. The operation can possibly be repeated.
- the honeycomb-shaped support can then be dried (for example in ambient air) for a period generally varying from a few minutes to a few hours, preferably during a period of between 30 minutes and 180 minutes.
- the impregnated support can then be dried (for example in a ventilated oven) at a temperature greater than or equal to 105 ° C and less than or equal to 300 ° C, preferably greater than or equal to 180 ° C and less than or equal to 250 ° vs.
- the drying time of the impregnated support is generally greater than or equal to 2 hours and less than or equal to 3 days. Preferably, this duration is greater than or equal to 12 hours and less than or equal to 2 days.
- the impregnation operation can be repeated several times, possibly with intermediate drying. Successive impregnations can be carried out 3 -
- the catalyst can be calcined (for example in a static oven) at a temperature greater than or equal to 200 ° C. and less than or equal to 800 ° C.
- this temperature is greater than or equal to 300 ° C and less than or equal to 600 ° C.
- this temperature is greater than or equal to 400 ° C. and less than or equal to 550 ° C.
- the calcination time is generally between a few hours and several days, preferably this drying time is greater than or equal to 6 hours and less than or equal to 12 hours.
- the amount of material deposited on the honeycomb support includes the amount of zeolite deposited as well as the amount of binder used.
- the amount of material deposited on the honeycomb-shaped support depends mainly on the size of the support. For example, for nests comprising 400 cells per inch 2 , the weight gain is generally greater than or equal to 10% and less than or equal to 80%. Preferably, the weight gain is greater than 20% and less than or equal to 70%.
- the weight gain is greater than or equal to 30% and less than or equal to 55%.
- the desired amount of catalyst is reached by depositing 3 to 5 layers of dispersion on the support in the form of honeycombs.
- the increase in the number of layers leads to better adhesion of the deposit to the support.
- the adhesion of the zeolite layer on the support in the form of honeycombs can be promoted by pre-impregnation of said support with the pure binder.
- the support can be pretreated in an acidic or basic medium depending on the nature of the support to obtain a greater deposit during the first impregnation step.
- a surfactant can also be added to the dispersion to increase the amount of material deposited during the first impregnation.
- the catalyst according to the invention can be regenerated after several reaction cycles generally by heat treatment, by washing or by treatment with using an oxidizing agent such as hydrogen peroxide and thus recover an activity level and a selectivity close to that of the fresh catalyst.
- the catalyst according to the invention can be used in chemical reactions in the liquid phase such as, for example, oxidation or epoxidation reactions. Consequently, the invention also relates to the use of a catalyst comprising a zeolite deposited on a support in the form of honeycombs in chemical reactions in the liquid phase.
- the catalyst according to the invention is particularly suitable for epoxidation reactions of olefins with a peroxide compound in the liquid phase.
- the products obtained are the corresponding epoxides (or oxirannes).
- the process of the present invention applies to all olefins, aliphatic or alicyclic, whatever the number of carbon atoms in the carbon chain, the position of the unsaturation and the presence of a chemical function in the chain .
- ethylene can be cited propylene, allyl chloride, 1-butene, 2-butene, octene-1, cyclohexene, cyclooctene and mesityl oxide.
- Allyl chloride and propylene are particularly suitable for the synthesis of epichlorohydrin or propylene oxide.
- the peroxide compound is preferably hydrogen peroxide.
- a reaction solvent is usually added to allow the olefin and hydrogen peroxide to come into contact. Among the possible solvents, methanol is preferred.
- the catalyst according to the present invention is generally used in a continuous or batch process.
- a continuous process is preferred.
- the reaction temperature is generally greater than or equal to 0 ° C and less than or equal to 100 ° C.
- this temperature is greater than or equal to 5 ° C and less than or equal to 50 ° C.
- this temperature is greater than or equal to 10 ° C and less than or equal to 40 ° C.
- the residence time is the ratio between the volume of the empty reactor and the feed rate.
- the residence time per reactor is generally greater than or equal to 1 minute and less than or equal to 100 minutes.
- the residence time is greater than or equal to 5 minutes and less than or equal to 80 minutes.
- the residence time is greater than or equal to 10 minutes and less than or equal to 50 minutes.
- the molar ratio between the quantity of olefin used and the quantity of hydrogen peroxide is generally greater than or equal to 1 and less than or equal to 20. Preferably, this ratio is greater than or equal to 1.5 and less than or equal to 10.
- the molar ratio between the quantity of olefin used and the quantity of solvent is generally greater than or equal to 2 and less than or equal to 50. Preferably, this ratio is greater than or equal to 5 and less than or equal to 10.
- TC 1 - (the number of moles of hydrogen peroxide found divided by the number of moles of hydrogen peroxide used); it is expressed in percent
- the selectivity is given by the ratio between the quantity of epoxide obtained divided by the sum of all the products formed
- the quantity of epoxide formed is the quantity formed after the time necessary for the conversion rate of hydrogen peroxide after putting into operation for one hour, to drop to 75% of this value.
- Example 1 The invention is more fully illustrated in the following nonlimiting examples.
- Example 1 The invention is more fully illustrated in the following nonlimiting examples.
- a catalyst was prepared comprising TS-1 deposited on a support in the form of a honeycomb.
- Example 1 The catalyst obtained in Example 1 was used in epoxidation reactions.
- the installation comprises two vertical tubular reactors, thermostatically controlled, arranged in cascade. Two catalyst cartridges are placed in each reactor. Each reactor is provided with a loop and a pump allowing the recirculation of the liquid on the catalyst. The temperature is controlled by a coil traversed by an oil regulated in temperature in each reactor.
- the mixture of reagents (olefin, hydrogen peroxide and methanol) is prepared just before its introduction at constant flow rate at the top of the first reactor.
- the linear speed of passage of the solution in recirculation in the reactor was adjusted to 0.94 m / min and the recirculation rate is of the order of 30 liters / hour.
- test duration was set based on a 25% decrease of the initial activity of the catalyst in the first reactor after a start-hour.
- Table II shows the conditions and the results of the tests carried out.
- propylene which is then introduced in gaseous form into the reactor, is transformed into propylene oxide.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Catalysts (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR9814722-6A BR9814722A (pt) | 1997-12-01 | 1998-11-23 | Catalisador, processo de fabricá-lo, utilização do mesmo, e, processo de fabricação de epóxidos, preferivelmente epicloridrina ou óxido de propileno. |
EP98963500A EP1051255B1 (fr) | 1997-12-01 | 1998-11-23 | Catalyseur a base de zeolite, son utilisation et procede d'epoxydation en presence de ce catalyseur |
AU18748/99A AU1874899A (en) | 1997-12-01 | 1998-11-23 | Catalyst based on zeolite, use and epoxidation method in the presence of said catalyst |
JP2000523006A JP4712189B2 (ja) | 1997-12-01 | 1998-11-23 | ゼオライトベース触媒、その使用及びこの触媒の存在下でのエポキシ化方法 |
DE69826524T DE69826524T2 (de) | 1997-12-01 | 1998-11-23 | Zeolithische katalysator, seine verwendung und epoxidierungsverfahren in gegenwart dieses katalysator |
US09/555,454 US6603027B1 (en) | 1997-12-01 | 1998-11-23 | Catalyst based on zelolite, use and epoxidation method in the presence of this catalyst |
AT98963500T ATE276827T1 (de) | 1997-12-01 | 1998-11-23 | Zeolithische katalysator, seine verwendung und epoxidierungsverfahren in gegenwart dieses katalysator |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE9700973A BE1011581A3 (fr) | 1997-12-01 | 1997-12-01 | Catalyseur a base de zeolite, son utilisation et procede d'epoxydation en presence de ce catalyseur. |
BE9700973 | 1997-12-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999028035A1 true WO1999028035A1 (fr) | 1999-06-10 |
Family
ID=3890872
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1998/007530 WO1999028035A1 (fr) | 1997-12-01 | 1998-11-23 | Catalyseur a base de zeolite, son utilisation et procede d'epoxydation en presence de ce catalyseur |
Country Status (13)
Country | Link |
---|---|
US (1) | US6603027B1 (fr) |
EP (1) | EP1051255B1 (fr) |
JP (1) | JP4712189B2 (fr) |
AR (1) | AR018021A1 (fr) |
AT (1) | ATE276827T1 (fr) |
AU (1) | AU1874899A (fr) |
BE (1) | BE1011581A3 (fr) |
BR (1) | BR9814722A (fr) |
DE (1) | DE69826524T2 (fr) |
ES (1) | ES2229556T3 (fr) |
SA (1) | SA99191013B1 (fr) |
WO (1) | WO1999028035A1 (fr) |
ZA (1) | ZA9810738B (fr) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001163866A (ja) * | 1999-12-07 | 2001-06-19 | Kuraray Co Ltd | 3−メチルテトラヒドロフランの製造方法 |
EP1340542A1 (fr) * | 2002-02-28 | 2003-09-03 | Corning Incorporated | Structure monolitique, revêtue de zeolite et son procédé de fabrication |
WO2012101175A1 (fr) | 2011-01-27 | 2012-08-02 | Solvay Sa | Procédé de production de 1,2-époxy-3-chloropropane |
WO2012101176A1 (fr) | 2011-01-27 | 2012-08-02 | Solvay Sa | Procédé de fabrication du 1,2-époxy-3-chloropropane |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1138387A1 (fr) * | 2000-03-29 | 2001-10-04 | Degussa AG | Procédé de préparation d'un corps moulé en titano-silicalite |
AU2004285019B9 (en) * | 2003-10-27 | 2011-11-24 | Vertex Pharmaceuticals Incorporated | HCV NS3-NS4A protease resistance mutants |
US7837977B2 (en) * | 2005-09-13 | 2010-11-23 | Chevron U.S.A. Inc. | Preparation of titanosilicate zeolite TS-1 |
CN102773048B (zh) * | 2011-05-09 | 2017-06-06 | 波利玛利欧洲股份公司 | 生产环己酮肟的氨肟化反应器 |
TW201332982A (zh) | 2011-11-04 | 2013-08-16 | Dow Global Technologies Llc | 用於製造環氧化物的方法及系統 |
Citations (5)
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EP0526896A1 (fr) * | 1991-08-07 | 1993-02-10 | Toyota Jidosha Kabushiki Kaisha | Catalyseur pour la purification des effluents gazeux |
EP0559021A2 (fr) * | 1992-03-04 | 1993-09-08 | Degussa Aktiengesellschaft | Réduction de NOx dans les gaz d'échappement pauvres de moteurs de véhicules |
DE4240693A1 (de) * | 1992-12-03 | 1994-06-09 | Leuna Werke Ag | Oxidationskatalysator |
DE4334981A1 (de) * | 1993-10-14 | 1995-04-20 | Daimler Benz Ag | Reaktor zur katalytischen Entfernung von CO in H¶2¶-reichem Gas |
DE4425672A1 (de) * | 1994-07-20 | 1996-01-25 | Basf Ag | Oxidationskatalysator, Verfahren zu seiner Herstellung und Oxidationsverfahren unter Verwendung des Oxidationskatalysators |
Family Cites Families (10)
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IT1152299B (it) | 1982-07-28 | 1986-12-31 | Anic Spa | Procedimento per l'espossidazione di composti olefinici |
CA1295598C (fr) * | 1986-07-29 | 1992-02-11 | Makoto Imanari | Procede d'elimination des oxydes d'azote dans les gaz d'echappement |
JP4135818B2 (ja) * | 1997-03-03 | 2008-08-20 | 株式会社日本触媒 | 炭化水素の部分酸化用触媒および炭化水素の部分酸化方法 |
WO1997034692A1 (fr) * | 1996-03-21 | 1997-09-25 | Japan As Represented By Director General Of Agency Of Industrial Science And Technology | Catalyseurs et procede pour l'oxydation partielle des hydrocarbures |
DE69708880T2 (de) * | 1996-07-01 | 2002-04-11 | Dow Chemical Co | Verfahren zur direkten oxidation von olefinen zu olefinoxiden |
DE19644348A1 (de) * | 1996-10-25 | 1998-04-30 | Degussa | Verfahren zur Herstellung von titanhaltigen Molekularsieben |
US6054112A (en) * | 1996-10-25 | 2000-04-25 | Degussa-Huls Ag | Process for the preparation of titanium containing molecular sieves |
US6042807A (en) * | 1997-04-02 | 2000-03-28 | Arco Chemical Technology, L.P. | Tellurium-containing molecular sieves |
JP4016461B2 (ja) * | 1997-09-04 | 2007-12-05 | ダイソー株式会社 | オレフィンの選択的エポキシ化法 |
BE1011852A3 (fr) * | 1998-03-24 | 2000-02-01 | Solvay | Procede de fabrication d'un oxiranne. |
-
1997
- 1997-12-01 BE BE9700973A patent/BE1011581A3/fr not_active IP Right Cessation
-
1998
- 1998-11-23 BR BR9814722-6A patent/BR9814722A/pt not_active Application Discontinuation
- 1998-11-23 DE DE69826524T patent/DE69826524T2/de not_active Expired - Lifetime
- 1998-11-23 AT AT98963500T patent/ATE276827T1/de not_active IP Right Cessation
- 1998-11-23 AU AU18748/99A patent/AU1874899A/en not_active Abandoned
- 1998-11-23 WO PCT/EP1998/007530 patent/WO1999028035A1/fr active IP Right Grant
- 1998-11-23 ES ES98963500T patent/ES2229556T3/es not_active Expired - Lifetime
- 1998-11-23 US US09/555,454 patent/US6603027B1/en not_active Expired - Lifetime
- 1998-11-23 JP JP2000523006A patent/JP4712189B2/ja not_active Expired - Lifetime
- 1998-11-23 EP EP98963500A patent/EP1051255B1/fr not_active Expired - Lifetime
- 1998-11-24 ZA ZA9810738A patent/ZA9810738B/xx unknown
- 1998-11-30 AR ARP980106068A patent/AR018021A1/es unknown
-
1999
- 1999-01-27 SA SA99191013A patent/SA99191013B1/ar unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0526896A1 (fr) * | 1991-08-07 | 1993-02-10 | Toyota Jidosha Kabushiki Kaisha | Catalyseur pour la purification des effluents gazeux |
EP0559021A2 (fr) * | 1992-03-04 | 1993-09-08 | Degussa Aktiengesellschaft | Réduction de NOx dans les gaz d'échappement pauvres de moteurs de véhicules |
DE4240693A1 (de) * | 1992-12-03 | 1994-06-09 | Leuna Werke Ag | Oxidationskatalysator |
DE4334981A1 (de) * | 1993-10-14 | 1995-04-20 | Daimler Benz Ag | Reaktor zur katalytischen Entfernung von CO in H¶2¶-reichem Gas |
DE4425672A1 (de) * | 1994-07-20 | 1996-01-25 | Basf Ag | Oxidationskatalysator, Verfahren zu seiner Herstellung und Oxidationsverfahren unter Verwendung des Oxidationskatalysators |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001163866A (ja) * | 1999-12-07 | 2001-06-19 | Kuraray Co Ltd | 3−メチルテトラヒドロフランの製造方法 |
JP4578602B2 (ja) * | 1999-12-07 | 2010-11-10 | 株式会社クラレ | 3−メチルテトラヒドロフランの製造方法 |
EP1340542A1 (fr) * | 2002-02-28 | 2003-09-03 | Corning Incorporated | Structure monolitique, revêtue de zeolite et son procédé de fabrication |
WO2012101175A1 (fr) | 2011-01-27 | 2012-08-02 | Solvay Sa | Procédé de production de 1,2-époxy-3-chloropropane |
WO2012101176A1 (fr) | 2011-01-27 | 2012-08-02 | Solvay Sa | Procédé de fabrication du 1,2-époxy-3-chloropropane |
US8735614B2 (en) | 2011-01-27 | 2014-05-27 | Solvay Sa | Process for the manufacture of 1,2-epoxy-3-chloropropane |
US8796478B2 (en) | 2011-01-27 | 2014-08-05 | Solvay Sa | Process for the manufacture of 1,2-epoxy-3-chloropropane |
Also Published As
Publication number | Publication date |
---|---|
AR018021A1 (es) | 2001-10-31 |
ZA9810738B (en) | 2000-05-24 |
JP2001524381A (ja) | 2001-12-04 |
ES2229556T3 (es) | 2005-04-16 |
DE69826524T2 (de) | 2006-02-23 |
BE1011581A3 (fr) | 1999-11-09 |
BR9814722A (pt) | 2000-10-03 |
EP1051255B1 (fr) | 2004-09-22 |
EP1051255A1 (fr) | 2000-11-15 |
AU1874899A (en) | 1999-06-16 |
DE69826524D1 (de) | 2004-10-28 |
SA99191013B1 (ar) | 2006-09-20 |
US6603027B1 (en) | 2003-08-05 |
JP4712189B2 (ja) | 2011-06-29 |
ATE276827T1 (de) | 2004-10-15 |
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