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EP2297123A1 - Procédé de production d`oxyde d`éthylène - Google Patents

Procédé de production d`oxyde d`éthylène

Info

Publication number
EP2297123A1
EP2297123A1 EP09753625A EP09753625A EP2297123A1 EP 2297123 A1 EP2297123 A1 EP 2297123A1 EP 09753625 A EP09753625 A EP 09753625A EP 09753625 A EP09753625 A EP 09753625A EP 2297123 A1 EP2297123 A1 EP 2297123A1
Authority
EP
European Patent Office
Prior art keywords
reaction
zones
zone
reaction zone
reaction zones
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.)
Withdrawn
Application number
EP09753625A
Other languages
German (de)
English (en)
Inventor
Evin Hizaler Hoffmann
Leslaw Mleczko
Ralph Schellen
Stephan Schubert
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Intellectual Property GmbH
Original Assignee
Bayer Technology Services GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer Technology Services GmbH filed Critical Bayer Technology Services GmbH
Publication of EP2297123A1 publication Critical patent/EP2297123A1/fr
Withdrawn legal-status Critical Current

Links

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

Definitions

  • the present invention relates to a process for the production of ethylene oxide by catalytic gas phase oxidation of ethylene with oxygen, wherein the reaction is carried out in 5 to 50 successive reaction zones under adiabatic conditions, and a reactor system for carrying out the method.
  • Ethylene oxide is generally subject to catalytic influence of e.g. Silver catalysts prepared from gaseous ethylene and oxygen in an exothermic, catalytic reaction according to formula (I):
  • ethylene oxide produced by the reaction of formula (I) forms an essential starting material for many other syntheses in the chemical industry.
  • ethylene oxide is used in the production of polymers such as polyethylene glycols, but also as a substance for chemical sterilization of substances that are perishable and not accessible to heat treatment.
  • EP 0 821 678 B1 discloses a process for the production of ethylene oxide from gases comprising ethylene and oxygen, in which the conversion is carried out on a silver-based heterogeneous catalyst in a single reaction zone which is operated several times in parallel. It is further disclosed that in particular the controlled cooling of the reaction zone is a technical problem to be solved in the disclosure by means of a specific flow and temperature control of the cooling liquid.
  • the disclosed catalyst temperatures are in the range of 150 ° C to 350 0 C. It is disclosed no adiabatic operation.
  • the disclosed reactor inlet pressures range from 1 to 40 bar.
  • the disclosed process is disadvantageous because a high technical effort has to be made in one reaction zone in order to keep the exothermic reaction in temperature ranges which are advantageous for the conversion of ethylene with oxygen to ethylene oxide. Furthermore, it can be assumed that due to the high throughputs that are to be achieved and the associated large spatial expansion of the
  • Reaction zone a temperature profile sets in the same, which is at least in some areas, either below the optimum temperature to achieve a high selectivity of the conversion of ethylene to ethylene oxide or above thereof. Furthermore, the reaction enthalpy can not be used to increase the reaction rate.
  • US Pat. No. 6,172,244 B1 discloses an apparatus and a process for the heterogeneous catalytic conversion of ethylene with oxygen into ethylene oxide, wherein a plurality of parallel reaction zones are surrounded by these surrounding cooling walls.
  • gases besides ethylene and oxygen can be supplied to the process / apparatus.
  • gases may be, for example, nitrogen or methane.
  • side reaction to carbon dioxide and water is particularly exothermic and should therefore be avoided. Neither standard operating temperatures nor inlet temperatures of the process gases are disclosed.
  • a two-stage procedure is disclosed in US 6,717,001 B2, wherein in a first reaction zone, a fresh catalyst and in another reaction zone aged catalyst is used.
  • an increased proportion of ethylene in the process gas from 1.1 to 4 times the proportion in the first reaction zone is used in the further reaction zone.
  • the oxygen concentrations in the reaction zones should be kept within a range that no ignition of the process gases can take place.
  • the possible inlet pressures of the process are between 10 and 35 bar.
  • the proportion of ethylene in the process gases supplied to the process should be below 50 mol%. Cooling between the first reaction zone and the further reaction zone is not disclosed.
  • the disclosed process is disadvantageous because no means for cooling the process gases between the reaction zones are disclosed.
  • the method is technically disadvantageous because with a temperature increase in the reaction zones beyond the planned level, no means are available to prevent the process gases of the process from inflammation.
  • the possibility of controlling the temperatures of the process is not given in US Pat. No. 6,717,001 B2.
  • EP 1 251 951 (B1) discloses a device and the possibility of carrying out chemical reactions in the device, wherein the device is characterized by a cascade of reaction zones in contact with one another and heat exchanger devices which are arranged in a composite with one another. The method to be carried out here is thus characterized by the contact of the various reaction zones with a respective heat exchanger device in the form of a cascade. There is no disclosure as to the usability of the apparatus and method for the synthesis of ethylene oxide from gaseous oxygen and ethylene. Thus, it remains unclear how, starting from the disclosure of EP 1 251 951 (B1), such a reaction should be carried out by means of the device and the method carried out therein.
  • EP 1 251 951 (B1) is carried out in a device the same as or similar to the disclosure regarding the device.
  • a significant amount of heat takes place by heat conduction between the reaction zones and the adjacent heat exchange zones.
  • the Revelation regarding the oscillating temperature profile can therefore only be understood that the temperature peaks detected here would be stronger if this contact did not exist.
  • Another indication of this is the exponential increase in the disclosed temperature profiles between the individual temperature peaks. These indicate that there is some heat sink of appreciable but limited capacity in each reaction zone which can reduce the temperature rise in it.
  • EP 1 251 951 (B1) discloses multi-stage processes in cascades of reaction zones from which heat in an undefined amount is removed by heat conduction. Accordingly, the disclosed method is disadvantageous in that accurate temperature control of the process gases of the reaction is not possible.
  • Ethylene in the context of the present invention refers to a process gas which is introduced into the process of the invention and which comprises ethylene.
  • the proportion of ethylene in the process gases supplied to the process is usually between 15 and 50 mol%, preferably between 20 and 40 mol%.
  • Oxygen in the context of the present invention refers to a process gas which is introduced into the process according to the invention and which comprises oxygen.
  • the proportion of oxygen in the process gases supplied to the process is usually between 5 and 30 mol%, preferably between 15 and 25 mol%.
  • ethylene and oxygen may also include secondary components.
  • minor components that may be included in the process gases include argon, nitrogen, carbon dioxide, methane, and / or ethane.
  • process gases are understood as gas mixtures which comprise oxygen and / or ethylene and / or ethylene oxide and / or secondary components.
  • adiabat means that no heat supply or removal measures are taken.
  • a heat transfer can be reduced, for example, by insulation by means of generally known insulation means, such as polystyrene insulating materials, or by sufficiently large distances to heat sinks or heat sources, the insulation means being air.
  • An advantage of the adiabatic driving method according to the invention of the 5 to 50 reaction zones connected in series with respect to a non-adiabatic mode of operation is that no means for heat removal have to be provided in the reaction zones, which entails a considerable simplification of the construction. This results in particular simplifications in the manufacture of the reactor and in the scalability of the process and an increase in reaction conversions.
  • the heat generated in the course of the exothermic reaction progress can be utilized in the single reaction zone to increase the conversion in a controlled manner.
  • Another advantage of the method according to the invention is the possibility of very accurate temperature control, due to the close staggering of adiabatic reaction zones. It can thus be set and controlled in each reaction zone advantageous in the reaction progress temperature.
  • the catalysts used in the process according to the invention are usually catalysts which consist of a material which, in addition to its catalytic activity for the reaction of the formula (I), is characterized by sufficient chemical resistance under the conditions of the process and by a high specific surface area.
  • Catalyst materials characterized by such chemical resistance under the conditions of the process are, for example, catalysts comprising silver supported on alumina.
  • Specific surface area in the context of the present invention refers to the area of the catalyst material that can be reached by the process gases based on the mass of catalyst material used.
  • a high surface area is a specific surface area of at least 10 m 2 / g, preferably of at least 20 m 2 Ig.
  • the catalysts of the invention are each in the reaction zones and can be used in all known forms, e.g. Fixed bed, fluidized bed, fluidized bed present.
  • the fixed bed arrangement comprises a catalyst bed in the strict sense, ie loose, supported or unsupported catalyst in any form and in the form of suitable packs.
  • catalyst bed as used herein also encompasses contiguous areas of suitable packages on a support material or structured catalyst supports. These would be, for example, to be coated ceramic honeycomb carrier with comparatively high geometric surfaces or corrugated layers of metal wire mesh on which, for example, catalyst granules is immobilized.
  • a special form of packing in the context of the present invention, the presence of the catalyst in monolithic form is considered.
  • a monolithic catalyst comprising silver supported on alumina.
  • the monolithic catalyst is provided with channels through which the process gases flow.
  • the channels have a diameter of 0.1 to 3 mm, preferably a diameter of 0.2 to 2 mm, particularly preferably from 0.3 to 1 mm.
  • a monolithic catalyst with channels of the specified diameter is particularly advantageous, since this explosion protection can be ensured. This is done by absorbing the enthalpy through the wall of the monolith and thus suppressing further propagation of flames.
  • the catalyst is preferably present in loose beds of particles.
  • the conversion takes place in 7 to 40, more preferably 10 to 30 reaction zones connected in series.
  • a preferred further embodiment of the method is characterized in that the process gas emerging from at least one reaction zone is subsequently passed through at least one heat exchange zone downstream of said reaction zone.
  • each reaction zone is at least one, preferably exactly one heat exchange zone, through which the process gas leaving the reaction zone is passed.
  • the reaction zones can either be arranged in a reactor or arranged divided into several reactors. The arrangement of the reaction zones in a reactor leads to a reduction in the number of apparatuses used.
  • the individual reaction zones and heat exchange zones can also be arranged together in a reactor or in any combination of reaction zones with heat exchange zones in several reactors.
  • reaction zones and heat exchange zones are present in a reactor, then in an alternative embodiment of the invention there is a heat insulation zone between them, in order to be able to obtain the adiabatic operation of the reaction zone.
  • each of the series-connected reaction zones can be replaced or supplemented independently of one another by one or more reaction zones connected in parallel.
  • the use of reaction zones connected in parallel allows in particular their replacement or supplementation during ongoing continuous operation of the process.
  • Parallel and successive reaction zones may in particular also be combined with one another.
  • the process according to the invention particularly preferably has exclusively reaction zones connected in series.
  • the reactors preferably used in the process according to the invention can consist of simple containers with one or more reaction zones, as e.g. in Ulimann's Encyclopedia of Industrial Chemistry (Fifth, Completely Revised Edition, VoI B4, page 95-104, pages 210-216), wherein in each case between the individual reaction zones and / or heat exchange zones heat insulation zones can be additionally provided.
  • the catalysts or the fixed beds thereof are mounted in a manner known per se on or between gas-permeable walls comprising the reaction zone of the reactor. Particularly in the case of thin fixed beds, technical devices for uniform gas distribution can be provided in the flow direction in front of the catalyst beds become. These can be perforated plates, bubble-cap trays, valve trays or other internals which cause a uniform entry of the process gas into the fixed bed by producing a small but uniform pressure loss.
  • the inlet temperature of the process gas entering the first reaction zone is from 10 to 290 ° C., preferably from 50 to 270 ° C., particularly preferably from 100 to 250 ° C.
  • the absolute pressure at the inlet of the first reaction zone is between 3 and 30 bar, preferably between 5 and 25 bar, more preferably between 7 and 20 bar.
  • the residence time of the process gas in a reaction zone is between 1 and 60 s, preferably between 2 and 30 s, particularly preferably between 5 and 20 s.
  • the ethylene and the oxygen are preferably fed only before the first reaction zone.
  • This has the advantage that the entire process gas can be used for the absorption and removal of the heat of reaction in all reaction zones.
  • the space-time yield can be increased, or the necessary catalyst mass can be reduced.
  • the temperature of the conversion can be controlled via the supply of gas between the reaction zones.
  • the process gas is passed after exiting a reaction zone through one or more of the above-mentioned heat exchange zones located behind the respective reaction zones.
  • These can be embodied as heat exchange zones in the form of heat exchangers known to the person skilled in the art, such as, for example, tube bundle, plate, annular groove, spiral, finned tube, micro heat exchanger.
  • the heat exchangers are preferably microstructured heat exchangers.
  • microstructured means that the heat exchanger for the purpose of heat transfer comprises fluid-carrying channels, which are characterized in that they have a hydraulic diameter between 50 ⁇ m and 5 mm.
  • the hydraulic diameter is calculated as four times the flow cross-sectional area of the fluid-conducting channel divided by the circumference of the channel.
  • steam is generated during cooling of the process gas in the heat exchange zones by the heat exchanger.
  • the heat exchangers which include the heat exchange zones, to carry out evaporation on the side of the cooling medium, preferably partial evaporation.
  • Partial evaporation referred to in the context of the present invention, an evaporation in which a gas / liquid mixture of a substance is used as a cooling medium and in which there is still a gas / liquid mixture of a substance after heat transfer in the heat exchanger.
  • the export of evaporation is particularly advantageous, because in this way the achievable heat transfer coefficient from / to process gases on / from cooling / heating medium is particularly high and thus efficient cooling can be achieved.
  • Performing a partial evaporation is particularly advantageous because the absorption / release of heat by the cooling medium thereby no longer results in a temperature change of the cooling medium, but only the gas / liquid equilibrium is shifted. This has the consequence that over the entire heat exchange zone, the process gas is cooled to a constant temperature. This in turn safely prevents the occurrence of temperature profiles in the flow of process gases, thereby improving control over the reaction temperatures in the reaction zones In particular, the formation of local overheating by temperature profiles is prevented.
  • a mixing zone can also be provided upstream of the inlet of a reaction zone in order to standardize the temperature profiles in the flow of process gases which may arise during cooling by mixing transversely to the main flow direction.
  • the reaction zones connected in series are operated at an average temperature increasing or decreasing from reaction zone to reaction zone. This means that within a sequence of reaction zones, the temperature can be both increased and decreased from reaction zone to reaction zone. This can be adjusted, for example, via the control of the heat exchange zones connected between the reaction zone. Further options for setting the average temperature are described below.
  • the thickness of the flow-through reaction zones can be chosen to be the same or different and results according to laws generally known in the art from the residence time described above and the process gas quantities enforced in the process.
  • the mass flows of product gas (ethylene oxide) which can be carried out according to the invention by the process, and from which the amounts of process gas to be used, are usually between 0.01 and 45 t / h, preferably between 0.1 and 40 t / h, particularly preferably between 1 and 35 t / h.
  • the maximum outlet temperature of the process gas from the reaction zones is usually in a range from 260 ° C to 320 ° C, preferably from 270 ° C to 310 ° C, more preferably from 280 ° C to 300 ° C.
  • the control of the temperature in the reaction zones is preferably carried out by at least one of the following measures: dimensioning of the adiabatic reaction zone, control of heat dissipation between the reaction zones, addition of gas between the reaction zones, molar ratio of the reactants / excess of oxygen used, addition of inert gases, in particular Nitrogen or methane and / or argon, before and / or between the reaction zones.
  • the composition of the catalysts in the reaction zones according to the invention may be identical or different.
  • the same catalysts are used in each reaction zone.
  • a less active catalyst can be used and in the further reaction zones the activity of the catalyst can be increased from reaction zone to reaction zone.
  • the control of the catalyst activity can also be carried out by dilution with inert materials or carrier material.
  • a catalyst in the first and / or second reaction zone which is particularly stable against deactivation at the temperatures of the process in these reaction zones.
  • the inventive method is thus characterized by high space-time yields, combined with a reduction of the apparatus sizes and a simplification of the apparatus or reactors.
  • This surprisingly high space-time yield is made possible by the interaction of the inventive and preferred embodiments of the new method.
  • the interaction of staggered, adiabatic reaction zones with interposed heat exchange zones and the defined residence times allows precise control of the process and the resulting high space-time yields, as well as a reduction in the by-products formed, such as CO 2 and water is achieved.
  • Another object of the invention is a reactor system for the reaction of ethylene and oxygen to ethylene oxide, characterized in that there are leads (Z) for a
  • Process gas comprising ethylene and oxygen or for at least two process gases, of which at least one comprises ethylene and at least one oxygen and 5 to 50 successive reaction zones (R) in the form of fixed beds of a heterogeneous
  • Catalyst comprising, between the reaction zones heat insulation zones (I) in the form of insulating material and between these heat exchange zones (W) in the form of plate heat exchangers, with the reaction zones on and Derivatives for the process gases are connected and include the supply and discharge lines for a cooling medium.
  • the reactor system may also comprise 7 to 40, preferably 10 to 30 reaction zones in the form of fixed beds.
  • the insulating material of the heat insulating zones is preferably a material having a
  • FIG. 1 shows a schematic representation of an embodiment of the reactor system according to the invention, the following reference numerals being used in the figures:
  • T reactor temperature
  • U ethylene conversion
  • Y ethylene oxide selectivity
  • the process gas flows over a total of 18 fixed catalyst beds in the form of monoliths with channel diameters of the monoliths of 0.5 mm, which are coated with a catalyst containing silver on alumina, ie through 18 reaction zones.
  • Each after a reaction zone is a heat exchange zone in which the process gas was cooled before it enters the next reaction zone.
  • the process gas used at the beginning of the first reaction zone contains 31, 9 mol% ethylene, 21.1 mol% oxygen, 32.3 mol% methane, 2.2 mol% CO 2 , 10.1 mol% argon, 1 , 1 mol% ethane and 1.3 mol% nitrogen.
  • the absolute inlet pressure of the process gas directly in front of the first reaction zone is 10 bar.
  • the length of the fixed catalyst beds, ie the reaction zones is always 1 m.
  • the amount of catalyst coated on the monoliths is 20% by weight. There is no replenishment of gas before the individual catalyst stages.
  • the total residence time in the system is 14 seconds.
  • the results are shown in FIG.
  • the individual reaction zones are listed on the x-axis, so that a spatial course of developments in the process is visible.
  • the temperature of the process gas is indicated on the left y-axis.
  • the temperature profile across the individual reaction zones is shown as a thick, solid line.
  • On the right y-axis the total conversion of ethylene, as well as the selectivity of ethylene oxide is given.
  • the course of the conversion over the individual reaction zones is shown as a thick dashed line.
  • the course of selectivity as a thin solid line.
  • the inlet temperature of the process gas before the first reaction zone is about 289 ° C. Due to the exothermic reaction to ethylene oxide under adiabatic conditions, the temperature in the first reaction zone rises to about 300 0 C, before the process gas is cooled in the downstream heat exchange zone. The inlet temperature before the next reaction zone is again about 289 ° C. By exothermic adiabatic reaction, it rises again to about 300 0 C. The sequence of heating and cooling continues. The inlet temperatures of the process gas upstream of the individual reaction zones only change slightly in the course of the process to a value of about 291 ° C. Another feature of the operation of the reaction zones under adiabatic conditions is shown in FIG. Considering the shape of the temperature profile within the reaction zones and the shape of their temperature profile, it can be seen that the slope of the temperature rise over the reaction zone never increases. This shows the essential property of the process that no significant heat sink is present in the reaction zones.
  • a conversion of ethylene of 11.3 mol% is obtained.
  • the selectivity is obtained at 88.3 mol%.
  • the space-time yield obtained based on the mass of catalyst used is 0.43 kg Et hyien o ⁇ i d / kg ⁇ ath.
  • the process gas flows through a total of 12 reaction zones, ie over 12 fixed catalyst beds in the form of monoliths, these now having channel diameters of 0.8 mm, but otherwise equal to those of Example 1.
  • Each after a reaction zone is a heat exchange zone in which the process gas is cooled before it enters the next reaction zone.
  • the process gas used at the outset like the inlet pressure before the first reaction zone, is identical to that of Example 1.
  • the length of the reaction zones is constantly 1 m.
  • the amount of catalyst coated on the monoliths is 35% by weight. This is achieved after the first reaction zone oscillating, in a temperature window between 280 ° C and 300 ° C, on which settles the process. There is no replenishment of gas before the individual catalyst stages.
  • the residence time in the system is a total of 10 seconds.
  • the results are shown in FIG.
  • the individual reaction zones are listed on the x-axis, so that a spatial course of developments in the process is visible.
  • the temperature of the process gas is indicated on the left y-axis.
  • the temperature profile across the individual reaction zones is shown as a thick, solid line.
  • On the right y-axis the total conversion of ethylene, as well as the selectivity of ethylene oxide is given.
  • the course of the conversion over the individual reaction zones is shown as a thick dashed line.
  • the course of selectivity as a thin solid line.
  • the inlet temperature of the process gas before the first reaction zone is about 282 0 C.
  • the exothermic reaction to ethylene oxide under adiabatic Conditions increases the temperature in the first reaction zone to about 300 ° C, before the process gas is cooled in the downstream heat exchange zone.
  • the inlet temperature before the next reaction zone is about 283 ° C.
  • exothermic adiabatic reaction it rises again to about 300 ° C.
  • the sequence of heating and cooling continues.
  • the inlet temperatures of the process gas upstream of the individual reaction zones changes only slightly in the course of the process to a value of about 286 ° C. It is thus possible, using a higher proportion of catalyst or using a more active catalyst, to effect the process analogously to Example in less stages 1, without fear of overheating the process.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)

Abstract

La présente invention concerne un procédé de production d’oxyde d’éthylène par oxydation catalytique en phase gazeuse d’éthylène avec de l’oxygène, la réaction s’effectuant dans 5 à 50 zones de réaction situées les unes derrière les autres dans des conditions adiabatiques. L’invention concerne également un système de réacteur pour mettre en œuvre le procédé.
EP09753625A 2008-05-29 2009-05-16 Procédé de production d`oxyde d`éthylène Withdrawn EP2297123A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008025835A DE102008025835A1 (de) 2008-05-29 2008-05-29 Verfahren zur Herstellung von Ethylenoxid
PCT/EP2009/003496 WO2009143970A1 (fr) 2008-05-29 2009-05-16 Procédé de production d’oxyde d’éthylène

Publications (1)

Publication Number Publication Date
EP2297123A1 true EP2297123A1 (fr) 2011-03-23

Family

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Application Number Title Priority Date Filing Date
EP09753625A Withdrawn EP2297123A1 (fr) 2008-05-29 2009-05-16 Procédé de production d`oxyde d`éthylène

Country Status (4)

Country Link
US (1) US20110060149A1 (fr)
EP (1) EP2297123A1 (fr)
DE (1) DE102008025835A1 (fr)
WO (1) WO2009143970A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108067162B (zh) * 2016-11-17 2020-12-08 中国石油化工股份有限公司 一种加氢反应器及加氢工艺方法
US20210331136A1 (en) * 2017-01-24 2021-10-28 Basf Corporation Monolithic catalysts for epoxidation

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Publication number Priority date Publication date Assignee Title
US4994589A (en) * 1985-08-13 1991-02-19 Union Carbide Chemicals And Plastics Company Inc. Catalytic system for epoxidation of alkenes
WO1996033182A1 (fr) * 1995-04-18 1996-10-24 Shell Internationale Research Maatschappij B.V. Procede d'oxydation catalytique en phase vapeur de l'ethylene
DE19719375A1 (de) 1997-05-07 1998-11-12 Linde Ag Verfahren und Reaktor zur Herstellung von Ethylenoxid
GB9910468D0 (en) * 1999-05-07 1999-07-07 Brightwell Dispensers Ltd Dispensing device
JP5224627B2 (ja) * 2000-01-25 2013-07-03 メギット （ユーケー） リミテッド 熱交換器付き化学反応器
US6372925B1 (en) 2000-06-09 2002-04-16 Shell Oil Company Process for operating the epoxidation of ethylene
US6765101B1 (en) * 2001-05-01 2004-07-20 Union Carbide Chemicals & Plastics Technology Corporation Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes

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Publication number Publication date
WO2009143970A1 (fr) 2009-12-03
DE102008025835A1 (de) 2009-12-03
US20110060149A1 (en) 2011-03-10

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