WO2000001480A1 - Entaluminierter katalysatorträger, verfahren zur herstellung des katalysatorträgers und verfahren zur hydratisierung von c2- oder c3-olefinen mit wasser in gegenwart eines katalysators, der aus diesem mit säure getränkten katalysatorträger besteht - Google Patents
Entaluminierter katalysatorträger, verfahren zur herstellung des katalysatorträgers und verfahren zur hydratisierung von c2- oder c3-olefinen mit wasser in gegenwart eines katalysators, der aus diesem mit säure getränkten katalysatorträger besteht Download PDFInfo
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- WO2000001480A1 WO2000001480A1 PCT/DE1999/001898 DE9901898W WO0001480A1 WO 2000001480 A1 WO2000001480 A1 WO 2000001480A1 DE 9901898 W DE9901898 W DE 9901898W WO 0001480 A1 WO0001480 A1 WO 0001480A1
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- catalyst
- catalyst support
- acid
- water
- support according
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Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
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- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/16—Clays or other mineral silicates
-
- 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
- C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
- C07C29/05—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds with formation of absorption products in mineral acids and their hydrolysis
- C07C29/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds with formation of absorption products in mineral acids and their hydrolysis the acid being phosphoric acid
Definitions
- Dealuminated catalyst support process for the preparation of the catalyst support and process for hydrating C? - or C olefins with water in the presence of a catalyst consisting of this catalyst support soaked in acid
- Ethene and isopropanol from propene are prepared in the presence of acidic catalysts, an aluminosilicate or silicate material impregnated with phosphoric acid being generally used as catalyst support.
- the material of the catalyst support is either built up from pure silica, such as silica gel (US 2,579,601), or consists of silica with varying alumina contents (US 3,311,568) or from pure, for example montmorillonite-containing sheet silicates (DE 29 08 491)
- Aluminum-containing catalyst supports or those based only on alumina show a significantly higher long-term stability, but they have considerable Disadvantage that during the hydration reaction aluminum is released from the catalyst support by the action of phosphoric acid. The aluminum is found as a poorly soluble deposit in the form of aluminum phosphates in the downstream equipment. This will gradually block them.
- DE 1 156 772 presents a process for reducing the aluminum content of the layered silicates by the action of hydrochloric acid.
- the carrier material still has a residual aluminum content of about 1 to 2% by weight.
- the present invention is therefore based on the object of being economical
- a dealuminated catalyst support based on essentially aluminum-containing layered silicates with a montmorillonite structure, with an aluminum content of less than 0.3% by weight has high long-term stability, and that in a process for the hydration of C 2 - or C 3 - olefins with
- the present invention therefore relates to a dealuminated catalyst support based on essentially aluminum-containing sheet silicates with a montmorillonite structure and an aluminum content of less than 0.3% by weight.
- Preferred embodiments of the catalyst and the process are described in the subclaims
- the present invention also relates to a process for reducing the aluminum content of a catalyst support which essentially comprises layered silicates containing aluminum having a montmorillonite structure, characterized in that the catalyst support
- the present invention also relates to a process for hydristering C 2 or C 3 olefins with water in the presence of a catalyst which consists of an acid-impregnated catalyst support as claimed in at least one of claims 1 to 22
- hydration or hydration reactions means the reaction of water with a carbon-carbon double bond
- dealuminization or dealuminated catalyst supports is understood to mean a process for reducing the aluminum content or a catalyst support with a reduced aluminum content
- a catalyst support based on calcined and post-treated layered silicates can be produced which has a significantly lower aluminum content than a catalyst support not treated according to the invention. Despite the lower aluminum content, the catalyst retains its long-term stability by using the process according to the invention
- Catalyst carrier in the process according to the invention for the hydration of C 2 or C 3 olefins with water the proportion of aluminum washed out during the hydration reaction is significantly reduced. As a result, during the hydration reaction, aluminum compounds which are less difficult to dissolve are formed,
- the dealuminated catalyst support according to the invention with an aluminum content of less than 0.3% by weight essentially contains layered silicates containing aluminum.
- the dealuminated catalyst support according to the invention particularly preferably has one
- the layered silicates containing aluminum are preferably smectites and preferably have a montmorillonite structure on layer.
- Silicates, which essentially contain layered silicates with a montmorillonite structure are, for example, the bentonites.
- the bentonites can be used, B mica, illite,
- the starting material for the preparation of the catalyst support according to the invention are commercially available catalyst supports, for example based on calcined and post-treated layered silicates
- the dealuminated catalyst support according to the invention with an aluminum content of less than 0.3% by weight, preferably less than 0.03% by weight, based on essentially aluminum-rich layered silicates with a montmorillonite structure, can be drunk with phosphoric acid, preferably a 10 to 90% by drinking the catalyst support .-%
- Phosphoric acid particularly preferably a 50 to 60% by weight phosphoric acid, so that the catalyst support contains 5 to 60%, preferably 30 to 40% phosphoric acid, followed by hydrothermal treatment at a temperature of 160 to 300 ° C, preferably at a temperature of 220 to 260 ° C and a water vapor pressure from 4 to 80 bar abso ⁇ ut, preferably at a
- a catalyst support which essentially comprises layered silicates containing aluminum
- commercially available layered silicates such as, for example, montmorillonite or bentonite
- the catalyst supports preferably have the shape of spherical bodies, such as, for example,
- the spherical bodies preferably have an average diameter of 1 to 10 mm, particularly preferably one of 4 to 6 mm
- the catalyst support is soaked in acid, treated hydrothermally, then washed and finally washed.
- the catalyst support is soaked in acid, preferably phosphoric acid.
- acid preferably phosphoric acid.
- the catalyst support should have a phosphoric acid content of 5 to 60% by weight, preferably 30 to 40% by weight.
- the catalyst support is then treated hydrothermally
- Layered silicate materials such as montmorillonite, change into cristobalite-like structures under the hydrothermal conditions. The originally existing micropores disappear along with them. Pore structures
- the hydrothermal treatment of the layered silicate-containing catalyst support can be used
- the catalyst support is washed with a basic, acidic or neutral solution, preferably with an acidic or neutral solution, particularly preferably with hydrochloric acid, with water which contains 0 to 30 parts of concentrated hydrochloric acid or with a neutral aqueous solution.
- the washing of the catalyst support is carried out at a temperature of 20 to 100 ° C, preferably 70 to 90 ° C
- the catalyst support can be washed with water until the wash water is neutral.
- the catalyst supports have a total pore volume of 0.2 to 0.9 ml / g, particularly preferably between 0.6 and 0.7 ml / g.
- the compressive strength of the catalyst supports should be at least 10 N / mm, preferably at least 20 N / mm.
- the hydrothermal treatment of the catalyst support impregnated with acid which contains 5 to 60% by weight, preferably 30 to 40% by weight, of phosphoric acid, is carried out using
- Catalyst in a hydration reaction of C 2 - or C 3 - olefins A 10 to 90% by weight, particularly preferably a 50 to 60% by weight, phosphoric acid is preferably used to impregnate the catalyst support
- a molar ratio of 0.1 to 0.8, preferably 0.15 and 0.5 is reacted in a reactor filled with the catalyst, preferably a tubular reactor, olefin and water.
- the olefin and water used are fed into the reactor in gaseous or liquid form, preferably in gaseous form.
- gas hourly space velocity (GHSV ) should be between 10 and 100 l n / min / l cat .
- the hydration reaction of is carried out at a temperature of 160 to 300 ° C. and a pressure of 20 to 200 bar a b so iut
- the hydration of ethene to ethanol is preferably carried out at a temperature of 220 to 260 ° C and a pressure of 60 to 80 bar absolute
- the reactor outlet can preferably be connected to a cooler which condenses out a large part of the subcritical components and makes these further processing steps, for example a separation by distillation, accessible
- the analysis can be carried out, for example, by gas chromatography
- the acid can be introduced into the reactor, for example, by spraying.
- the amount of acid contained in the If the reactor is introduced it can be made dependent on the analysis result of the outlet stream.
- the analysis of the outlet stream and the determination of the resulting amount of acid that is added can be carried out automatically
- the catalyst support is reacted with a basic, acidic or neutral solution, preferably with an acidic or neutral solution, particularly preferably with hydrochloric acid, with water which concentrated 0 to 30 parts
- the catalyst support can be washed at a temperature of 20 to 100 ° C, preferably at a temperature of 70 to 90 ° C
- the catalyst support can be neutralized with water
- wash water to be washed In the case of catalyst supports which have been hydrothermally treated by use as a catalyst in a hydration reaction, it can be advantageous, after reducing the aluminum content in the catalyst support, to burn off any carbon-containing compounds which may be adhering at 300 to 1
- a treated catalyst support with a reduced aluminum content is obtained.
- the treated catalyst supports have an average diameter of 1 to 10 mm, preferably one of 4 to 6 mm.
- the total pore volume is from 0.27 to 0.9 ml / g, preferably from 0.6 to 0.7 ml / g.
- the compressive strength after the treatment of the catalyst support is at least 10 N / mm, preferably at least 20 N / mm.
- the aluminum content of the treated catalyst support is less than 0.3% by weight, preferably less than 0.03% by weight
- the catalyst supports with reduced aluminum content produced by the process according to the invention can be used for the production of catalysts
- the catalyst supports with reduced aluminum content produced by the process according to the invention can be used according to the invention for hydrating C 2 or C 3 olefins with water in the presence of a catalyst which consists of a catalyst support which has been impregnated with acid and treated according to the invention
- the catalyst support is preferably soaked with an acid, preferably phosphoric acid.
- the phosphoric acid content of the impregnated catalyst support should be between 5 and 60% by weight, preferably between 30 and 40% by weight, in order to achieve maximum catalyst activity.
- An aqueous solution of phosphoric acid with a Phosphoric acid content from 10 to 90% by weight, preferably from 50 to 60% by weight acid catalyst is placed in a reactor, preferably a tubular reactor.
- the reactor is operated isothermally or non-isothermally, preferably isothermally, and can be heated electrically or by means of heat carriers.
- the reactor is fed continuously or batchwise, preferably continuously, with the educts water and C 2 or C 3 olefin.
- the ratio of water to olefin with which the starting materials are fed into the reactor is set to a molar ratio of 0.1 to 0.8, preferably 0.15 to 0.5.
- the molar ratio can be set, for example, with the aid of mass flow controllers.
- Educts can be fed into the reactor in liquid or gaseous form, preferably in gaseous form.
- it can be advantageous to feed both reactants into the reactor via an evaporator and / or thermostatic section which are heated to the reaction temperature electrically or by means of heat transfer media.
- the temperature in the reactor and the temperature at which the starting materials flow into the reactor are 160 to 300 ° C. In the case of hydratistering ethene to ethanol, the temperature in the reactor and the temperature at which the starting materials flow into the reactor are preferably 220 to 260 ° C.
- the pressure in the reactor is ut in the range of 20 to 200 bar Abso i, preferably from 60 to 80 bar a b iut so adjusted.
- the reactor outlet is preferably connected to a cooler, which condenses out a large part of the subcritical components and feeds these further processing steps.
- the analysis can be carried out, for example, by gas chromatography
- the acid preferably phosphoric acid
- the acid can be introduced into the reactor, for example, by spraying.
- the amount of acid that is introduced into the reactor can be made dependent on the analysis result of the exit stream.
- the analysis of the exit stream and the determination of the resulting amount of acid that is added can be done automatically .
- Example 1 Ethanol synthesis with an untreated catalyst support
- the test was carried out in a pilot plant, the core of which is an isothermally operated tubular reactor with a length of 1,000 mm and a diameter of 48 mm.
- the educts water and ethene are fed to the reactor via an evaporator or thermostatic section, which is electrically heated to the reaction temperature.
- the water is metered in using a pump, while the ethene is taken from 130 bar steel bottles.
- the inflow of a 0.3: 1 mixture of ethene and water (molar basis) is adjusted using a mass flow controller.
- the reactor outlet is connected to a cooler in order to condense out the majority of the subcritical components - essentially ethanol, water and diethyl ether; the rest goes into the exhaust gas, whose volume flow can be determined with a gas meter.
- Part of the exhaust gas is fed to a gas chromatograph via a bypass flow.
- the liquid discharge is also analyzed by gas chromatography.
- the synthesis of ethanol was in the present example at 240 ° C and 70 bar abs. measured.
- the standard test conditions are summarized in Table 1.
- the carrier characteristics are summarized in Table 2.
- the Sales and selectivity values achieved at the start of the experiment are also shown in Table 2.
- Catalyst carrier (old carrier) used as catalyst carrier. Again, the standard test conditions given in Table 1 apply. The results of the test and the characteristics of the catalyst carrier are also shown in Table 2
- Been surface of the impregnated Katalysatortragers after single use as a catalyst also is the unique use as a catalyst the aluminum content to approximately l A of the original content of aluminum reduces the remaining V * of the original aluminum content of the untreated Neutragers are during washed out of hydration from the catalyst support This
- FIGS. 1 and 2 The deactivation behavior of a catalyst support without a reduced aluminum content and one with a reduced aluminum content is shown in FIGS. 1 and 2
- the aluminum content of the catalyst support has been reduced to below 0.03% by weight by treating the old support with the aid of the method according to the invention. This value represents the detection limit of the atomic emission spectrometer used.
- the compressive strength of the treated old carrier, at 30 N / mm, is still sufficient to guarantee good long-term stability of the catalyst carrier
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Abstract
Description
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Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU56165/99A AU746348B2 (en) | 1998-07-03 | 1999-07-01 | Dealuminized catalyst support, method for producing said catalyst support and method for hydrating C2- or C3-olefins with water in the presence of catalyst consisting of this catalyst support impregnated with acid |
SK2009-2000A SK284617B6 (sk) | 1998-07-03 | 1999-07-01 | Dealuminizovaný katalyzátorový nosič, spôsob jeho výroby, spôsob hydratácie olefínov s dvoma alebo tromi atómami uhlíka vodou v prítomnosti katalyzátora, ktorý pozostáva z nosiča nasýteného kyselinou |
EA200100086A EA004067B1 (ru) | 1998-07-03 | 1999-07-01 | Носитель катализатора, очищенный от алюминия, способ получения этого носителя катализатора и способ гидратации c2- или c3-олефинов водой в присутствии катализатора, представляющего собой этот носитель, пропитанный кислотой |
EP99942719.8A EP1098700B2 (de) | 1998-07-03 | 1999-07-01 | Verfahren zur herstellung eines entaluminierten katalysators/katalysatortragers |
JP2000557915A JP4489295B2 (ja) | 1998-07-03 | 1999-07-01 | 脱アルミニウム化触媒坦体、この触媒坦体の製造方法及び酸を含浸させたこの触媒坦体を含有する触媒の存在下での、水によるc2又はc3オレフィンの水和方法 |
SI9930128T SI1098700T2 (sl) | 1998-07-03 | 1999-07-01 | Postopek za izdelavo dealuminiziranega katalizatorja/katalizatorskega nosilca |
AT99942719T ATE226109T1 (de) | 1998-07-03 | 1999-07-01 | Entaluminierter katalysatorträger, verfahren zur herstellung des katalysatorträgers und verfahren zur hydratisierung von c2- oder c3-olefinen mit wasser in gegenwart eines katalysators, der aus diesem mit säure getränkten katalysatorträger besteht |
DE59903105T DE59903105D1 (de) | 1998-07-03 | 1999-07-01 | Entaluminierter katalysatorträger, verfahren zur herstellung des katalysatorträgers und verfahren zur hydratisierung von c2- oder c3-olefinen mit wasser in gegenwart eines katalysators, der aus diesem mit säure getränkten katalysatorträger besteht |
US09/701,054 US6881699B1 (en) | 1998-07-03 | 1999-07-01 | Method for producing a dealuminized catalyst support |
PL345333A PL201697B1 (pl) | 1998-07-03 | 1999-07-01 | Sposób wytwarzania nośnika katalizatora i sposób uwadniania olefin |
US10/973,759 US20050131259A1 (en) | 1998-07-03 | 2004-10-26 | Dealuminized catalyst support, method for producing said catalyst support and method for hydrating C2- or C3-olefins with water in the presence of a catalyst consisting of this catalyst support impregnated with acid |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19829747A DE19829747A1 (de) | 1998-07-03 | 1998-07-03 | Entaluminierter Katalysatorträger, Verfahren zur Herstellung des Katalysatorträgers und Verfahren zur Hydratisierung von C2- oder C3-Olefinen mit Wasser in Gegenwart eines Katalysators, der aus diesem mit Säure getränkten Katalysatorträger besteht |
DE19829747.5 | 1998-07-03 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/973,759 Continuation US20050131259A1 (en) | 1998-07-03 | 2004-10-26 | Dealuminized catalyst support, method for producing said catalyst support and method for hydrating C2- or C3-olefins with water in the presence of a catalyst consisting of this catalyst support impregnated with acid |
Publications (2)
Publication Number | Publication Date |
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WO2000001480A1 true WO2000001480A1 (de) | 2000-01-13 |
WO2000001480A9 WO2000001480A9 (de) | 2001-01-04 |
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Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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PCT/EP1999/004486 WO2000001481A1 (de) | 1998-07-03 | 1999-06-29 | Entaluminierter katalysatorträger, verfahren zur herstellung des katalysatorträgers und verfahren zur hydratisierung von c2- oder c3-olefinen mit wasser in gegenwart eines katalysators, der aus diesem mit säure getränktem katalysatorträger besteht |
PCT/DE1999/001898 WO2000001480A1 (de) | 1998-07-03 | 1999-07-01 | Entaluminierter katalysatorträger, verfahren zur herstellung des katalysatorträgers und verfahren zur hydratisierung von c2- oder c3-olefinen mit wasser in gegenwart eines katalysators, der aus diesem mit säure getränkten katalysatorträger besteht |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/EP1999/004486 WO2000001481A1 (de) | 1998-07-03 | 1999-06-29 | Entaluminierter katalysatorträger, verfahren zur herstellung des katalysatorträgers und verfahren zur hydratisierung von c2- oder c3-olefinen mit wasser in gegenwart eines katalysators, der aus diesem mit säure getränktem katalysatorträger besteht |
Country Status (15)
Country | Link |
---|---|
US (3) | US6881699B1 (de) |
EP (2) | EP1096997B1 (de) |
JP (2) | JP2002519190A (de) |
KR (1) | KR100706055B1 (de) |
CN (1) | CN1117614C (de) |
AT (1) | ATE226109T1 (de) |
AU (1) | AU746348B2 (de) |
CA (1) | CA2336316C (de) |
DE (3) | DE19829747A1 (de) |
EA (1) | EA004067B1 (de) |
PL (1) | PL201697B1 (de) |
SK (1) | SK284617B6 (de) |
TW (1) | TW490318B (de) |
WO (2) | WO2000001481A1 (de) |
ZA (1) | ZA200007651B (de) |
Families Citing this family (6)
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MXPA04000118A (es) * | 2001-07-06 | 2004-06-03 | 3M Innovative Properties Co | Sustratos de fibras inorganicas para sistemas de escape y metodos de fabricacion de los mismos. |
KR100515586B1 (ko) * | 2002-10-14 | 2005-09-16 | 주식회사 엘지화학 | 활성이 우수한 인산촉매를 이용한 이소프로필알코올의제조방법 |
DE102008060888A1 (de) | 2008-12-09 | 2010-06-10 | Evonik Stockhausen Gmbh | Verfahren zur Herstellung von Acrolein umfassend die Aufarbeitung einer Rohglycerin-Phase |
US8197779B2 (en) * | 2009-01-08 | 2012-06-12 | Lg Hausys, Ltd. | Catalyst for removing nitrogen oxides from exhaust gas, method for preparing the same and method for removing nitrogen oxides using the same from exhaust gas |
DE102011005608A1 (de) | 2011-03-16 | 2012-09-20 | Evonik Oxeno Gmbh | Mischoxidzusammensetzungen und Verfahren zur Herstellung von Isoolefinen |
EP2939995A1 (de) | 2014-04-30 | 2015-11-04 | Sasol Solvents Germany GmbH | Verbessertes Wassermanagement zur Herstellung von Isopropylalkohol durch Gasphasenpropylenhydrierung |
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JP2598679B2 (ja) * | 1988-05-31 | 1997-04-09 | 株式会社妙徳 | 固定装置 |
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US5080778A (en) * | 1988-12-27 | 1992-01-14 | Uop | Hydrocarbon conversion process using novel silica-substituted aluminas |
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US5366948A (en) | 1991-03-12 | 1994-11-22 | Mobil Oil Corp. | Catalyst and catalytic conversion therewith |
JP2606487B2 (ja) * | 1991-06-25 | 1997-05-07 | 日本電気株式会社 | 半導体装置 |
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1998
- 1998-07-03 DE DE19829747A patent/DE19829747A1/de not_active Ceased
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1999
- 1999-06-29 EP EP99931210A patent/EP1096997B1/de not_active Revoked
- 1999-06-29 WO PCT/EP1999/004486 patent/WO2000001481A1/de not_active Application Discontinuation
- 1999-06-29 DE DE59911373T patent/DE59911373D1/de not_active Expired - Fee Related
- 1999-06-29 CA CA002336316A patent/CA2336316C/en not_active Expired - Lifetime
- 1999-06-29 JP JP2000557916A patent/JP2002519190A/ja active Pending
- 1999-07-01 EP EP99942719.8A patent/EP1098700B2/de not_active Expired - Lifetime
- 1999-07-01 US US09/701,054 patent/US6881699B1/en not_active Expired - Lifetime
- 1999-07-01 KR KR1020017000048A patent/KR100706055B1/ko not_active IP Right Cessation
- 1999-07-01 WO PCT/DE1999/001898 patent/WO2000001480A1/de active IP Right Grant
- 1999-07-01 EA EA200100086A patent/EA004067B1/ru not_active IP Right Cessation
- 1999-07-01 CN CN99808573A patent/CN1117614C/zh not_active Expired - Lifetime
- 1999-07-01 DE DE59903105T patent/DE59903105D1/de not_active Expired - Lifetime
- 1999-07-01 AT AT99942719T patent/ATE226109T1/de not_active IP Right Cessation
- 1999-07-01 PL PL345333A patent/PL201697B1/pl unknown
- 1999-07-01 JP JP2000557915A patent/JP4489295B2/ja not_active Expired - Fee Related
- 1999-07-01 SK SK2009-2000A patent/SK284617B6/sk not_active IP Right Cessation
- 1999-07-01 AU AU56165/99A patent/AU746348B2/en not_active Expired
- 1999-07-02 TW TW088111294A patent/TW490318B/zh not_active IP Right Cessation
-
2000
- 2000-12-19 ZA ZA200007651A patent/ZA200007651B/xx unknown
-
2003
- 2003-08-06 US US10/634,879 patent/US6881700B2/en not_active Expired - Lifetime
-
2004
- 2004-10-26 US US10/973,759 patent/US20050131259A1/en not_active Abandoned
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