WO2000007965A1 - Verfahren zur umsetzung einer organischen verbindung mit einem hydroperoxid - Google Patents

Verfahren zur umsetzung einer organischen verbindung mit einem hydroperoxid Download PDF

Info

Publication number
WO2000007965A1
WO2000007965A1 PCT/EP1999/005740 EP9905740W WO0007965A1 WO 2000007965 A1 WO2000007965 A1 WO 2000007965A1 EP 9905740 W EP9905740 W EP 9905740W WO 0007965 A1 WO0007965 A1 WO 0007965A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydroperoxide
organic compound
reaction
reactor
separation
Prior art date
Application number
PCT/EP1999/005740
Other languages
German (de)
English (en)
French (fr)
Inventor
Peter Bassler
Wolfgang Harder
Peter Resch
Norbert Rieber
Wilhelm Ruppel
Joaquim Henrique Teles
Andreas Walch
Anne Wenzel
Peter Zehner
Original Assignee
Basf Aktiengesellschaft
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=7876882&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2000007965(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Priority to AT99942819T priority Critical patent/ATE263744T1/de
Priority to EP99942819A priority patent/EP1102733B1/de
Priority to DE59909131T priority patent/DE59909131D1/de
Priority to AU56199/99A priority patent/AU5619999A/en
Priority to JP2000563600A priority patent/JP4555478B2/ja
Priority to CA002339710A priority patent/CA2339710A1/en
Priority to US09/762,290 priority patent/US6479680B1/en
Publication of WO2000007965A1 publication Critical patent/WO2000007965A1/de

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B41/00—Formation or introduction of functional groups containing oxygen
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B33/00—Oxidation in general

Definitions

  • the present invention relates to a process for reacting an organic compound with a hydroperoxide, hydroperoxide being separated off in the course of the process and reacted again with the organic compound.
  • the present invention also relates to a device for reacting an organic compound with a hydroperoxide.
  • Reactions of organic compounds with hydroperoxides i.e. with compounds of the general formula ROOH are usually carried out in one step in the customary processes of the prior art.
  • one-stage in this context refers to the hydroperoxide starting material and means that hydroperoxide is added to the organic compound to be reacted in only one step throughout the process.
  • US Pat. No. 5,262,550 describes a process for the epoxidation of alkenes in which alkene is reacted with hydrogen peroxide or a hydrogen peroxide precursor to give the corresponding alkene oxide in one step.
  • US-A-4,883,260 discloses a process in which alkene is reacted with hydrogen peroxide in one step in the steel autoclave or in the glass autoclave.
  • pages 5-1 to 5-21 disclose a process in which an approximately 40% by weight tert-butyl hydroperoxide solution is reacted with propene on a homogeneous Mo catalyst in one step, the alkene is epoxidized. 3.7 moles of propene are used per mole of hydroperoxide.
  • a disadvantage of these processes is that either a relatively large excess of the organic compound to be reacted or a very concentrated hydroperoxide has to be used in order to achieve optimal selectivities.
  • the present invention therefore relates to a process for reacting an organic compound with a hydroperoxide, which comprises at least the following steps (i) to (iii):
  • step (i) reacting the hydroperoxide with the organic compound to obtain a mixture comprising the reacted organic compound and unreacted hydroperoxide, (ii) separating the unreacted hydroperoxide from the mixture resulting from step (i), (iii) reacting the separated hydroperoxide from step (ii) with the organic compound.
  • the reaction of the organic compound with the hydroperoxide takes place in at least two stages (i) and (iii). It is also conceivable in the process according to the invention that the reaction of the organic compound with the hydroperoxide takes place in more than two stages. Depending on the number of stages in which the reaction takes place, it is of course also conceivable in the process according to the invention that more than one stage is run through in which the hydroperoxide used is separated off.
  • the present invention accordingly also relates to a process for reacting an organic compound with a hydroperoxide, which has the following steps (i) to (ix): (i) reacting the hydroperoxide with the organic compound to obtain a mixture M. (ii) separation of the hydroperoxide from the mixture resulting from step (i)
  • step (vii) reacting the separated hydroperoxide from step (vi) with the organic compound to obtain a mixture M, v , (viii) separating the hydroperoxide from that resulting from step (vii)
  • the separation of the hydroperoxide in the above-mentioned separation stages (ii), (iv), (vi) and (viii) can be carried out in the process according to the invention by all customary processes according to the prior art. Different separation methods can also be used in different separation stages.
  • the hydroperoxide is preferably removed by distillation in the removal stages. Depending on the requirements of the process, separation in one or more distillation columns is possible. Preferably in one Separation stage used to separate the hydroperoxide a distillation column.
  • separation stages it is also possible to carry out two or even more separation stages in a separation device in each case by means of a suitable reaction procedure. In general, it is accordingly possible to provide a total of m separation devices for n separation stages, 1 ⁇ m ⁇ n.
  • the converted organic compound in addition to the hydroperoxide, can also be separated from the mixture which results from a reaction stage in which the organic compound is reacted with the hydroperoxide.
  • the hydroperoxide after the hydroperoxide has been separated off, to transfer the remaining reaction material to a further separation device provided specifically for this purpose and to separate the converted organic compound from the reaction material there.
  • a further separation device provided specifically for this purpose and to separate the converted organic compound from the reaction material there.
  • the converted organic compound is preferably separated off in the respective separation device in addition to the hydroperoxide.
  • separation by distillation it is possible, for example, to remove the converted organic compound overhead from the mixture and to remove the hydroperoxide from the mixture in the side draw.
  • hydroperoxide and / or the converted organic compound are separated off in a distillation plant, it is possible in the process according to the invention to remove any high-boiling components of the mixture which are obtained as by-products from the reaction of the organic compound with the hydroperoxide via the bottom. It is also conceivable, for example, by adding preferably gaseous, low-boiling components, such as the organic compound, preferably propene itself, to lower the bottom temperature.
  • low-boiling components examples include Hydrocarbons with 1 to 4 carbon atoms such as methane, ethane, propane, butane, ethene or butenes. Nitrogen or argon, for example, can also be used.
  • the reaction of the organic compound with the hydroperoxide in stage (i) takes place in a suitable reactor R 1.
  • the starting materials for the reaction are the organic compound to be reacted, the hydroperoxide and, if necessary, one or more solvents which are suitable and / or required in the reaction.
  • the individual streams E, 1 are combined, preferably into a stream E, before they flow into the reactor R. It is also possible in principle to conduct the individual streams individually into the reactor R.
  • a stream E which consists of the combination of the streams E, 1 , E, 2 and E, 3, is preferably passed into the reactor R in the process according to the invention.
  • a stream is preferred in which the concentrations of the individual components of the stream are selected so that the stream is liquid and single-phase.
  • Hydroperoxide concentrations in E are preferably used which are in the range from 0.01 to 10, more preferably in the range from 0.1 to 9, more preferably in the range from 1 to 8% by weight and in particular in the range from 5 to 7% by weight.
  • the concentration of the organic compound to be reacted is chosen, for example, such that the molar ratio of organic compound to be reacted to hydroperoxide is in the range from 0.7 to 3.0, preferably in the range from 0.8 to 2.7, more particularly preferably in the range from 0.9 to 2.3 and in particular in the range from 1.0 to 2.0.
  • reaction conditions in reactor R in the process according to the invention are chosen so that the hydroperoxide conversion is generally in the range from 70 to 95%, preferably in the range from 80 to 94.5%, and particularly preferably in the range from 85 to 94%.
  • pressure p , temperature T, and residence time ⁇ t of the reaction mixture in the reactor R are preferably selected so that the mixture M ,, which results from the reaction, is liquid and single-phase.
  • Pressures p 1 are chosen which are generally in the range from autogenous pressure to 100 bar, preferably in the range from autogenous pressure to 40 bar and particularly preferably in the range from autogenous pressure to 30 bar.
  • the temperatures T are generally in the range from 0 to 120 ° C., preferably in the range from 10 to 100 ° C., more preferably in the range from 20 to 90 ° C. and particularly preferably in the range from 30 to 80 ° C.
  • the resulting mixture is fed as stream M, the separating device A. There, as described above, the hydroperoxide is separated from the mixture.
  • the distillation is generally carried out in such a way that M, at least 50%, preferably at least 60, more preferably at least 70%, particularly preferably at least 80% and particularly preferably at least 90 % of the converted organic compound are separated off.
  • the separation is preferably carried out in such a way that a liquid mixture containing the hydroperoxide is separated off.
  • This separated mixture is referred to below as M, 2 .
  • the separated mixture which contains the hydroperoxide contains, in addition to the hydroperoxide, for example small amounts of unreacted organic compound and / or unreacted organic compound.
  • the mixture M, 2 which contains the separated hydroperoxide, may contain any necessary solvent, which was added via stream E, 3 , or solvent, which was optionally contained in streams E, 1 and / or E [ 2 .
  • M a stream that flows in hereinafter referred to as M, 1 .
  • this contains, in addition to the reacted organic compound, the unreacted organic compound and / or small amounts of any necessary solvent which was added via stream E ⁇ or solvent which may be present in streams E, 1 and / or E. , 2 was included.
  • a stream M, 3 results from this separation.
  • Such high-boiling fractions can be, for example, by-products of the reaction in reactor R which are contained in stream M.
  • stage (iii) After passing through stages (i) and (ii), the hydroperoxide removed in stage (iii) is reacted again with the organic compound in the process according to the invention.
  • M, 2 can, for example, be conducted as a separate stream in R. Preheating of the current M, 2 is possible, as described above.
  • M, 2 it is also possible, for example, to supply M, 2 to stream E, 2 before the resulting stream E, 2 + M, 2 is passed into R. It is also possible for M, 2 to be the current E, which results from the combination of E, 1 to E, 3 , or a suitable, to mix as described above, which results from a suitable combination of any of the streams E, 1 to E, 3 .
  • the method preferably sets the concentrations of the components of the corresponding streams in such a way that the resulting stream remains liquid and single-phase.
  • stream M, 2 is passed into a second reactor R 1 .
  • the stream M, 2 thus, based on the reactor R ", represents the stream E" 2 in analogy to the streams flowing into the reactor R. Since in the reactor R ⁇ according to the invention, according to stage (iii), a If the separated hydroperoxide is reacted again with the organic compound to be reacted, at least one further stream E ⁇ 'is required with respect to the reactor R n . If necessary, a current E 3 may also be required, for example.
  • the streams E, 1 described above it is possible to pass the streams E, 1 individually or combined in suitable combinations into the reactor R 1 .
  • the current E 2 is preferably combined with a current E 1 or a current E 1 + E 3 and the resulting current is conducted into R M.
  • the concentrations of the components of the currents 1 and E ,, E "3 are preferably chosen so that the current E", which flows into the reactor R ", is liquid and single phase.
  • the concentration of the organic compound to be reacted is chosen such that the molar ratio of organic compound to hydroperoxide to be reacted is preferably in the range from 0.7 to 10.0, more preferably in the range from 0.8 to 8.0, particularly preferably in the range from 0.9 to 6.0 and in particular in the range from 1.0 to 4.0.
  • the reaction in the reactor R is carried out at a pressure p", a temperature T "and a residence time ⁇ t" of the reaction mixture, so that hydroperoxide conversions are achieved, which are generally in the range from> 90%, preferably in the range from > 92%, more preferably in the range> 95% and particularly preferably in the range from 95 to 99.5%.
  • Pressures p are selected which are generally in the range from autogenous pressure to 100 bar, preferably in the range from autogenous pressure to 40 bar and particularly preferably in the range from autogenous pressure to 30 bar.
  • the temperatures T are generally in the range from 0 to 120 ° C., preferably in the range from 10 to 100 ° C., more preferably in the range from 20 to 90 ° C. and particularly preferably in the range from 30 to 80 ° C.
  • the present invention relates to a process which is characterized in that reactions in steps (i) and (iii) are carried out in two separate reactors.
  • reactors which are most suitable for the respective reactions can of course be used as reactors.
  • a reactor is not restricted to a single container. Rather, it is also possible to use a stirred tank cascade as, for example, reactor R or, for example, reactor R.
  • Fixed bed reactors are preferably used as reactors in the process according to the invention. Accordingly, the present invention relates to a process as described above, which is characterized in that fixed-bed reactors are used as reactors for the reactions. Fixed-bed tube reactors are further preferably used as fixed-bed reactors.
  • reactor R 1 an isothermal fixed bed reactor and an adiabatic fixed bed reactor are used as reactor R 1.
  • the present invention therefore also relates to a device comprising an isothermal fixed bed reactor (I), a separating device (II) and an adiabatic fixed bed reactor (III).
  • the present invention also relates to the use of this device for reacting an organic compound with a hydroperoxide.
  • the present invention further relates to this use, the following steps (i) to (iii) being carried out in order to react the organic compound with the hydroperoxide: (i) reacting the hydroperoxide with the organic compound to obtain a mixture comprising the reacted organic compound and unreacted hydroperoxide,
  • hydroperoxides examples include, for example, tert-butyl hydroperoxide or ethylbenzene hydroperoxide, which are mentioned in the above-mentioned SRI report 2E “Propylene Oxide”.
  • the tert-butyl hydroperoxide is produced here starting from isobutane and oxygen.
  • the ethylbenzene hydroperoxide is produced starting from ethylbenzene and oxygen.
  • Hydrogen peroxide is preferably used as the hydroperoxide in the present process. Accordingly, the present invention also relates to a method as described above, which is characterized in that hydrogen peroxide is used as the hydroperoxide. An aqueous hydrogen peroxide solution is preferably used.
  • the anthraquinone process can be used to produce hydrogen peroxide, according to which practically the entire amount of hydrogen peroxide produced worldwide is produced.
  • This process is based on the catalytic hydrogenation of an anthraquinone compound to the corresponding anthrahydroquinone compound, subsequent reaction of the same with oxygen to form hydrogen peroxide and subsequent separation of the hydrogen peroxide formed by extraction.
  • the catalytic cycle is closed by renewed hydrogenation of the re-formed anthraquinone compound.
  • the present invention relates to a process as described above, which is characterized in that the organic compound is brought into contact with a heterogeneous catalyst during the reaction.
  • Catalysts are preferably used which comprise a porous oxidic material such as a zeolite.
  • Catalysts are preferably used which comprise a titanium, vanadium, chromium, niobium or zirconium-containing zeolite as the porous oxidic material.
  • Other titanium-containing zeolites are those with the structure of ZSM-48 or ZSM-12
  • Ti zeolites with an MFI, MEL or MFI / MEL mixed structure are to be regarded as particularly preferred for the process according to the invention.
  • the Ti-containing zeolite catalysts which are generally referred to as “TS-1”, “TS -2 ",” TS-3 "and Ti-zeolites with a ß-zeolite framework structure
  • a heterogeneous catalyst comprising the titanium-containing silicalite TS-1 is particularly preferably used in the process according to the invention.
  • porous oxidic material per se as the catalyst.
  • a shaped body as the catalyst which comprises the porous oxidic material. All processes according to the prior art can be used to produce the shaped body, starting from the porous oxidic material.
  • noble metals in the form of suitable noble metal components can be applied to the catalyst material.
  • This process is preferably used in order to include oxidation catalysts based on titanium or vanadium silicates
  • catalysts are available which have a content of 0.01 to 30% by weight of one or more noble metals from the group of ruthenium, rhodium, palladium, osmium, iridium, platinum, rhenium, gold and silver. Examples of such catalysts are described in DE-A 196 23 609 6, which is hereby fully incorporated by reference into the context of the present application with respect to the catalysts described therein
  • the molded body can be assembled. All kinds of comminution processes are conceivable, for example by splitting or breaking the molded body, as well as further chemical treatments, as described above, for example
  • a shaped body or more of it is used as a catalyst, this can be regenerated in the process according to the invention after deactivation by a process in which the regeneration is carried out by deliberately burning off the deposits responsible for the deactivation.
  • the process is preferably carried out in an inert gas atmosphere in precisely defined amounts contains oxygen-containing substances. This regeneration process is described in DE-A 197 23 949 8, which in this respect is fully incorporated into the context of the present application by reference
  • Hydroxylations such as the hydroxylation of mono-, bi- or polycyclic aromatics to mono-, di- or highly substituted hydroxyaromatics, for example the reaction of phenol and H 2 O 2 or of phenol and mixtures which deliver H 2 O 2 in situ, to hydroquinone, oxime formation from ketones in the presence of H 2 O 2 or mixtures which deliver H 2 O 2 in situ and ammonia (ammonoxation), for example the preparation of cyclohexanone oxime from cyclohexanone,
  • Organic compounds which have at least one C-C double bond are preferably reacted in the process according to the invention. Accordingly, the present invention relates to a process as described above, which is characterized in that the organic compound has at least one C-C double bond.
  • alkenes are mentioned as examples of such organic compounds with at least one C-C double bond:
  • Propene, propene oxide and methanol, M, 2 a stream resulting from the removal via side draw , which mainly comprises methanol and aqueous hydrogen peroxide solution and which is passed into the reactor R,
  • M a stream resulting from the reaction in reactor R ,, A, a distillation column for removal overhead and over the bottom
  • M, 1 a stream resulting from the removal overhead, which mainly comprises propene, propene oxide and methanol
  • M, 2 a current resulting from the enclosure via the bottom, mainly comprising hydrogen peroxide, water, methanol and high-boiling by-products and which is passed into the reactor R ", R and an adiabatic fixed-bed tube reactor,
  • M a stream from reactor R, which comprises propene, propene oxide and methanol.
  • the hydrogen peroxide conversion achieved was 85%.
  • the propene oxide selectivity with respect to hydrogen peroxide was 95%.
  • the discharge from the first reactor which contained methanol, water, propene oxide, by-products, unreacted propene and hydrogen peroxide, was depressurized in a column.
  • the column was operated at normal pressure and had about 15 theoretical stages.
  • the propene oxide was separated from the mixture down to ⁇ 1% by weight.
  • the bottom product was fed to a second tubular reactor.
  • the bottom product from the intermediate separation and a propene stream of about 9 g / h at 40 ° C. reaction temperature and 20 bar reaction pressure were passed through a second tubular reactor with a reaction volume of approx. 50 ml, filled with 28 g of extruded TS-1. After leaving the reactor, the reaction mixture was depressurized in a Sambay evaporator against atmospheric pressure. The separated low boilers were analyzed online in a gas chromatograph. The liquid The reaction product was collected, weighed and also analyzed by gas chromatography.
  • the hydrogen peroxide conversion achieved was 96%.
  • the propene oxide selectivity with respect to hydrogen peroxide was 96%.
  • reaction mixture was let down in a Sambay evaporator against atmospheric pressure.
  • the separated low boilers were analyzed online in a gas chromatograph.
  • the liquid reaction product was collected, weighed and also analyzed by gas chromatography.
  • the hydrogen peroxide conversion achieved was 98.4%.
  • the propene oxide selectivity with respect to hydrogen peroxide was 80.3%.
  • the propene oxide yield with respect to hydrogen peroxide was 79%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
PCT/EP1999/005740 1998-08-07 1999-08-09 Verfahren zur umsetzung einer organischen verbindung mit einem hydroperoxid WO2000007965A1 (de)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AT99942819T ATE263744T1 (de) 1998-08-07 1999-08-09 Verfahren zur umsetzung einer organischen verbindung mit einem hydroperoxid
EP99942819A EP1102733B1 (de) 1998-08-07 1999-08-09 Verfahren zur umsetzung einer organischen verbindung mit einem hydroperoxid
DE59909131T DE59909131D1 (de) 1998-08-07 1999-08-09 Verfahren zur umsetzung einer organischen verbindung mit einem hydroperoxid
AU56199/99A AU5619999A (en) 1998-08-07 1999-08-09 Method for reacting an organic compound with a hydroperoxide
JP2000563600A JP4555478B2 (ja) 1998-08-07 1999-08-09 有機化合物とヒドロペルオキシドとを反応させるための方法
CA002339710A CA2339710A1 (en) 1998-08-07 1999-08-09 Process for the reaction of an organic compound with a hydroperoxide
US09/762,290 US6479680B1 (en) 1998-08-07 1999-08-09 Method for reacting an organic compound with a hydroperoxide

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19835907A DE19835907A1 (de) 1998-08-07 1998-08-07 Verfahren zur Umsetzung einer organischen Verbindung mit einem Hydroperoxid
DE19835907.1 1998-08-07

Publications (1)

Publication Number Publication Date
WO2000007965A1 true WO2000007965A1 (de) 2000-02-17

Family

ID=7876882

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/005740 WO2000007965A1 (de) 1998-08-07 1999-08-09 Verfahren zur umsetzung einer organischen verbindung mit einem hydroperoxid

Country Status (15)

Country Link
US (1) US6479680B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EP (1) EP1102733B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
JP (1) JP4555478B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
KR (1) KR20010072320A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CN (1) CN1231432C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AT (1) ATE263744T1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AU (1) AU5619999A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CA (1) CA2339710A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (2) DE19835907A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ES (1) ES2220106T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ID (1) ID27449A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
IN (1) IN2001CH00173A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
MX (1) MX222918B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
WO (1) WO2000007965A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ZA (1) ZA200101003B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6596883B2 (en) 2001-08-23 2003-07-22 Degussa Ag Process for the epoxidation of olefins
US6608219B2 (en) 2001-06-13 2003-08-19 Degussa Ag Process for the epoxidation of olefins
WO2004009569A1 (de) * 2002-07-23 2004-01-29 Basf Attiengesellschaft Verfahren zur kontinuierlich betriebenen zwischenabtrennung des bei der koppelproduktfreien oxiransynthese entstehenden oxirans unter verwendung einer trennwandkolonne
WO2004009204A1 (de) * 2002-07-23 2004-01-29 Basf Aktiengesellschaft Verfahren zur kontinuierlich betriebenen reindestillation von oxiranen, speziell von propylenoxid
WO2004009566A1 (de) * 2002-07-23 2004-01-29 Basf Aktiengesellschaft Verfahren zur kontinuierlichen reindestillation des bei der propylenoxidsynthese verwendeten lösungsmittels methanol
WO2004009572A1 (de) * 2002-07-23 2004-01-29 Basf Aktiengesellschaft Verfahren zur kontinuierlich betriebenen destillation des bei der koppelproduktfreien oxiransynthese verwendenten lösungsmittels
WO2004009568A1 (de) * 2002-07-23 2004-01-29 Basf Aktiengesellschaft Verfahren zur kontinuierlichen herstellung von propylenglykolen
WO2004009567A1 (de) * 2002-07-23 2004-01-29 Basf Aktiengesellschaft Verfahren zur kontinuierlich betriebenen reindestillation des bei der koppelproduktfreien propylenoxidsynthese verwendeten lösungsmittels methanol unter gleichzeitiger abtrennung der methoxypropanole
WO2004013116A1 (de) * 2002-07-29 2004-02-12 Basf Aktiengesellschaft Verfahren zur herstellung von propenyloxid unter verwendung eines nachreaktors mit mehreren einspeise- und/oder ablaufstellen
WO2004092150A1 (de) * 2003-04-16 2004-10-28 Basf Aktiengesellschaft Verfahren zur herstellung von propylenoxid
WO2004092149A1 (de) * 2003-04-16 2004-10-28 Basf Aktiengesellschaft Verfahren zur herstellung eines alkenoxids
US7332634B2 (en) 2002-07-23 2008-02-19 Basf Aktiengesellschaft Method for the continuous purification by distillation of 1,2-propylene glycol that accumulates during the synthesis of propylene oxide without coupling products
US7408073B2 (en) 2002-10-23 2008-08-05 Basf Aktiengesellschaft Returning an olefin which is not reacted during the oxidation of olefins
US7518004B2 (en) 2003-05-08 2009-04-14 Basf Aktiengesellschaft Method for reacting an organic compound with a hydroperoxide
US7544818B2 (en) 2002-10-23 2009-06-09 Basf Aktiengesellschaft Continuous recirculation of the olefin which has not been reacted in the oxidation of olefins by hydroperoxides, by means of solvent scrubbing
WO2010018022A1 (de) * 2008-08-11 2010-02-18 Evonik Röhm Gmbh Verfahren und anlage zur herstellung von glycidyl(meth)acrylat
EP1740562B2 (en) † 2004-04-21 2019-09-25 Basf Se A method of separating an olefin from a gas stream

Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1122247A1 (de) 2000-02-07 2001-08-08 Degussa AG Verfahren zur Epoxidierung von Olefinen
EP1122248A1 (de) 2000-02-07 2001-08-08 Degussa AG Verfahren zur Epoxidierung von Olefinen
EP1122246A1 (de) 2000-02-07 2001-08-08 Degussa AG Verfahren zur Epoxidierung von Olefinen
FR2810982B1 (fr) 2000-06-28 2002-09-27 Solvay Procede de fabrication d'oxiranne comprenant la separation de l'oxiranne du milieu reactionnel
FR2810983B1 (fr) 2000-06-28 2004-05-21 Solvay Procede de fabrication d'oxiranne au moyen d'un compose peroxyde
DE10032884A1 (de) 2000-07-06 2002-01-24 Basf Ag Verfahren zur Herstellung von Propylenoxid
DE10105527A1 (de) 2001-02-07 2002-08-08 Basf Ag Verfahren zur Herstellung eines Epoxids
WO2002088148A1 (en) 2001-04-30 2002-11-07 The Regents Of The University Of Michigan Isoreticular metal-organic frameworks, process for forming the same, and systematic design of pore size and functionality therein,with application for gas storage
US6596881B2 (en) 2001-06-13 2003-07-22 Degussa Ag Process for the epoxidation of olefins
US6600055B2 (en) 2001-06-13 2003-07-29 Degussa Ag Process for the epoxidation of olefins
US6749668B2 (en) 2001-06-18 2004-06-15 Degussa Ag Process for the recovery of combustible components of a gas stream
US6610865B2 (en) 2001-08-15 2003-08-26 Degussa Ag Process for the epoxidation of olefins
EP1293505A1 (en) * 2001-08-22 2003-03-19 Degussa AG Process for the epoxidation of olefins
DE10143195A1 (de) * 2001-09-04 2003-03-20 Basf Ag Integriertes Verfahren zur Herstellung von Polyurethan-Schäumen
WO2003050100A1 (en) * 2001-12-05 2003-06-19 Dow Global Technologies Inc. Process of preparing an olefin oxide from olefin and organic hydroperoxide
DE10164348A1 (de) 2001-12-28 2003-07-17 Basf Ag Verfahren zur Herstellung von 1-Methoypropanol-2
US6720436B2 (en) 2002-03-18 2004-04-13 Degussa Ag Process for the epoxidation of olefins
US7141683B2 (en) 2002-05-02 2006-11-28 Degussa Ag Process for the epoxidation of olefins
DE10240129B4 (de) 2002-08-30 2004-11-11 Basf Ag Integriertes Verfahren zur Synthese von Propylenoxid
US7722847B2 (en) 2002-09-30 2010-05-25 Evonik Degussa Gmbh Aqueous hydrogen peroxide solutions and method of making same
US6838572B2 (en) 2002-09-30 2005-01-04 Degussa Ag Process for the epoxidation of olefins
US7169945B2 (en) 2002-11-26 2007-01-30 Degussa Ag Process for the epoxidation of olefins
DE10320635A1 (de) 2003-05-08 2004-11-18 Basf Ag Verfahren zur Herstellung von Propylenoxid
EP1633760B1 (en) 2003-05-09 2010-05-05 The Regents of The University of Michigan MOFs with a high surface area and methods for producing them
US20050004404A1 (en) 2003-07-03 2005-01-06 Basf Akiengesellschaft Process for the alkoxylation of monools in the presence of metallo-organic framework materials
CN1914219A (zh) * 2003-12-05 2007-02-14 密歇根大学董事会 金属有机多面体
US20060006054A1 (en) 2004-07-07 2006-01-12 Basf Aktiengesellshaft Separation of propylene oxide from a mixture comprising propylene oxide and methanol
WO2006047423A2 (en) 2004-10-22 2006-05-04 The Regents Of The University Of Michigan Covalently linked organic frameworks and polyhedra
ITMI20042169A1 (it) * 2004-11-12 2005-02-12 Polimeri Europa Spa Processo continuo per la preparazione di fenolo da benzene in reattore a letto fisso
CA2604084A1 (en) 2005-04-07 2006-10-19 The Regents Of The University Of Michigan High gas adsorption in a microporous metal-organic framework with open-metal sites
WO2007038508A2 (en) 2005-09-26 2007-04-05 The Regents Of The University Of Michigan Metal-organic frameworks with exceptionally high capacity for storage of carbon dioxide at room-temperature
CN101432070A (zh) 2006-02-28 2009-05-13 密歇根大学董事会 官能化沸石骨架的制备
CN101835733B (zh) * 2007-08-21 2014-06-25 巴斯夫欧洲公司 氧化有机化合物的方法和装置
US8575379B2 (en) 2007-08-21 2013-11-05 Basf Se Process and device for the oxidation of organic compounds
WO2011017402A1 (en) 2009-08-05 2011-02-10 Dow Global Technologies Inc. Process for producing propylene oxide
TWI523689B (zh) 2010-03-25 2016-03-01 陶氏全球科技公司 使用預處理環氧催化劑製備環氧丙烷之方法
RU2472786C1 (ru) * 2011-05-13 2013-01-20 Закрытое акционерное общество "Химтэк Инжиниринг" Способ получения оксида пропилена
FR2975393B1 (fr) * 2011-05-19 2013-05-10 Rhodia Operations Procede d'hydroxylation de phenols et d'ethers de phenols
JP2015533883A (ja) * 2012-09-07 2015-11-26 エルジー・ケム・リミテッド 光配向性重合体、これを含む配向膜および液晶位相差フィルム
CN105439986A (zh) * 2014-08-27 2016-03-30 中国石油化工股份有限公司 环氧化物的生产方法
EP3380448B1 (de) * 2015-11-25 2019-08-28 Evonik Degussa GmbH Verfahren zur herstellung von 1,2-propandiol aus propen und wasserstoffperoxid
CN107974319B (zh) * 2016-10-25 2020-05-12 中国石化工程建设有限公司 一种制备煤制替代天然气的耐硫甲烷化工艺

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0031537A1 (de) * 1979-12-29 1981-07-08 Bayer Ag Verfahren zur Herstellung von Oxiranen
US4977285A (en) * 1989-12-08 1990-12-11 Texaco Chemical Company Recovery of tertiary butyl hydroperoxide and tertiary butyl alcohol
EP0568336A2 (en) * 1992-04-30 1993-11-03 ARCO Chemical Technology, L.P. Epoxidation process using titanium-rich silicalite catalysts
US5274138A (en) * 1993-01-21 1993-12-28 Texaco Chemical Company Epoxidation process for manufacture of olefin oxide and alcohol
US5349072A (en) * 1993-07-06 1994-09-20 Texaco Chemical Company Staged epoxidation of propylene with recycle
US5374747A (en) * 1993-12-23 1994-12-20 Arco Chemical Technology, L.P. Epoxidation process and catalyst therefore
US5384418A (en) * 1994-01-25 1995-01-24 Arco Chemical Technology, L.P. Integrated process for epoxide production
EP0659473A1 (en) * 1993-12-20 1995-06-28 ARCO Chemical Technology, L.P. Catalytic converter and method for highly exothermic reactions
US5463090A (en) * 1994-10-27 1995-10-31 Arco Chemical Technology, L.P. Integrated process for epoxide production

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1152299B (it) 1982-07-28 1986-12-31 Anic Spa Procedimento per l'espossidazione di composti olefinici
US5646314A (en) * 1994-11-16 1997-07-08 Arco Chemical Technology, L.P. Process for titanium silicalite-catalyzed epoxidation

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0031537A1 (de) * 1979-12-29 1981-07-08 Bayer Ag Verfahren zur Herstellung von Oxiranen
US4977285A (en) * 1989-12-08 1990-12-11 Texaco Chemical Company Recovery of tertiary butyl hydroperoxide and tertiary butyl alcohol
EP0568336A2 (en) * 1992-04-30 1993-11-03 ARCO Chemical Technology, L.P. Epoxidation process using titanium-rich silicalite catalysts
US5274138A (en) * 1993-01-21 1993-12-28 Texaco Chemical Company Epoxidation process for manufacture of olefin oxide and alcohol
US5349072A (en) * 1993-07-06 1994-09-20 Texaco Chemical Company Staged epoxidation of propylene with recycle
EP0659473A1 (en) * 1993-12-20 1995-06-28 ARCO Chemical Technology, L.P. Catalytic converter and method for highly exothermic reactions
US5374747A (en) * 1993-12-23 1994-12-20 Arco Chemical Technology, L.P. Epoxidation process and catalyst therefore
US5384418A (en) * 1994-01-25 1995-01-24 Arco Chemical Technology, L.P. Integrated process for epoxide production
US5463090A (en) * 1994-10-27 1995-10-31 Arco Chemical Technology, L.P. Integrated process for epoxide production

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6608219B2 (en) 2001-06-13 2003-08-19 Degussa Ag Process for the epoxidation of olefins
US6596883B2 (en) 2001-08-23 2003-07-22 Degussa Ag Process for the epoxidation of olefins
CN1304384C (zh) * 2002-07-23 2007-03-14 巴斯福股份公司 丙二醇的连续制备
US7527712B2 (en) 2002-07-23 2009-05-05 Basf Aktiengesellschaft Method for the continuous purification by distillation of the solvent methanol, used in the synthesis of propylene oxide
WO2004009566A1 (de) * 2002-07-23 2004-01-29 Basf Aktiengesellschaft Verfahren zur kontinuierlichen reindestillation des bei der propylenoxidsynthese verwendeten lösungsmittels methanol
WO2004009572A1 (de) * 2002-07-23 2004-01-29 Basf Aktiengesellschaft Verfahren zur kontinuierlich betriebenen destillation des bei der koppelproduktfreien oxiransynthese verwendenten lösungsmittels
WO2004009568A1 (de) * 2002-07-23 2004-01-29 Basf Aktiengesellschaft Verfahren zur kontinuierlichen herstellung von propylenglykolen
WO2004009567A1 (de) * 2002-07-23 2004-01-29 Basf Aktiengesellschaft Verfahren zur kontinuierlich betriebenen reindestillation des bei der koppelproduktfreien propylenoxidsynthese verwendeten lösungsmittels methanol unter gleichzeitiger abtrennung der methoxypropanole
US7658893B2 (en) 2002-07-23 2010-02-09 Basf Aktiengesellschaft Method for the continuous production of propylene glycol
US7332634B2 (en) 2002-07-23 2008-02-19 Basf Aktiengesellschaft Method for the continuous purification by distillation of 1,2-propylene glycol that accumulates during the synthesis of propylene oxide without coupling products
US7550064B2 (en) 2002-07-23 2009-06-23 Basf Aktiengesellschaft Method for continuously operated pure distillation of oxiranes, especially propylene oxide
US7084310B2 (en) 2002-07-23 2006-08-01 Basf Aktiengesellschaft Method for the continuous production of propylene glycol
WO2004009569A1 (de) * 2002-07-23 2004-01-29 Basf Attiengesellschaft Verfahren zur kontinuierlich betriebenen zwischenabtrennung des bei der koppelproduktfreien oxiransynthese entstehenden oxirans unter verwendung einer trennwandkolonne
WO2004009204A1 (de) * 2002-07-23 2004-01-29 Basf Aktiengesellschaft Verfahren zur kontinuierlich betriebenen reindestillation von oxiranen, speziell von propylenoxid
WO2004013116A1 (de) * 2002-07-29 2004-02-12 Basf Aktiengesellschaft Verfahren zur herstellung von propenyloxid unter verwendung eines nachreaktors mit mehreren einspeise- und/oder ablaufstellen
US7408073B2 (en) 2002-10-23 2008-08-05 Basf Aktiengesellschaft Returning an olefin which is not reacted during the oxidation of olefins
US7544818B2 (en) 2002-10-23 2009-06-09 Basf Aktiengesellschaft Continuous recirculation of the olefin which has not been reacted in the oxidation of olefins by hydroperoxides, by means of solvent scrubbing
RU2324689C2 (ru) * 2003-04-16 2008-05-20 Басф Акциенгезельшафт Способ получения пропиленоксида
US7408074B2 (en) 2003-04-16 2008-08-05 Basf Aktiengesellschaft Method for producing an alkene oxide
US7378536B2 (en) 2003-04-16 2008-05-27 Basf Aktiengesellschaft Method for producing propylene oxide
CN100364983C (zh) * 2003-04-16 2008-01-30 巴斯福股份公司 环氧丙烷的制备方法
WO2004092150A1 (de) * 2003-04-16 2004-10-28 Basf Aktiengesellschaft Verfahren zur herstellung von propylenoxid
RU2339628C2 (ru) * 2003-04-16 2008-11-27 Басф Акциенгезельшафт Способ получения алкеноксида
WO2004092149A1 (de) * 2003-04-16 2004-10-28 Basf Aktiengesellschaft Verfahren zur herstellung eines alkenoxids
US7518004B2 (en) 2003-05-08 2009-04-14 Basf Aktiengesellschaft Method for reacting an organic compound with a hydroperoxide
EP1740562B2 (en) † 2004-04-21 2019-09-25 Basf Se A method of separating an olefin from a gas stream
WO2010018022A1 (de) * 2008-08-11 2010-02-18 Evonik Röhm Gmbh Verfahren und anlage zur herstellung von glycidyl(meth)acrylat

Also Published As

Publication number Publication date
JP2002522402A (ja) 2002-07-23
ZA200101003B (en) 2002-02-06
ES2220106T3 (es) 2004-12-01
MXPA01001248A (es) 2001-10-01
EP1102733B1 (de) 2004-04-07
AU5619999A (en) 2000-02-28
DE19835907A1 (de) 2000-02-17
DE59909131D1 (de) 2004-05-13
CN1231432C (zh) 2005-12-14
MX222918B (es) 2004-09-24
CA2339710A1 (en) 2000-02-17
JP4555478B2 (ja) 2010-09-29
KR20010072320A (ko) 2001-07-31
EP1102733A1 (de) 2001-05-30
IN2001CH00173A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 2006-10-06
ID27449A (id) 2001-04-12
US6479680B1 (en) 2002-11-12
ATE263744T1 (de) 2004-04-15
CN1322186A (zh) 2001-11-14

Similar Documents

Publication Publication Date Title
EP1102733B1 (de) Verfahren zur umsetzung einer organischen verbindung mit einem hydroperoxid
EP1268456B1 (de) Verfahren zur umsetzung einer organischen verbindung mit einem hydroperoxid
DE69521735T2 (de) Integriertes Verfahren zur Epoxidherstellung
EP1377562B1 (de) Verfahren zur herstellung eines epoxids
EP1526904B1 (de) Verfahren zur kontinuierlich betriebenen reindestillation von oxiranen, speziell von propylenoxid
EP1206459B1 (de) Verfahren zur umsetzung einer organischen verbindung mit einem hydroperoxid
DE69600245T2 (de) Integriertes Epoxydationsverfahren
DE69300720T2 (de) Epoxidationsverfahren mit titanreichen Silikatkatalysatoren.
DE60304169T2 (de) Verfahren zur epoxidierung von olefinen
EP2625158B1 (de) Verfahren zur herstellung von ketonen, insbesondere makrocyclischer ketone
DE69602302T2 (de) Integriertes Epoxidationsverfahren
EP2038245B1 (de) Verfahren zur reinigung von cyclischen ketonen
EP1558596B1 (de) Rückführung des bei der oxidation von olefinen nicht umgesetzten olefins
EP2041061B1 (de) Reinigung von Cyclododecanon durch thermisches Behandeln
EP1527059B1 (de) Verfahren zur herstellung von propenyloxid unter verwendung eines nachreaktors mit mehreren einspeise- und/oder ablaufstellen
DE69509339T2 (de) Verfahren zur Herstellung von Wasserstoffperoxyd, integrierter Prozess zur Epoxydierung und Alkylammoniumsalze von sulfonsäuresubstituiertem Anthrahydrochinon und Anthrachinon
DE10233381A1 (de) Verfahren zur kontinuierlich betriebenen Destillation des bei der koppel-produktfreien Oxiransynthese verwendeten Lösungsmittels
WO2004074268A1 (de) Verfahren zur herstellung eines epoxids
WO2004009569A1 (de) Verfahren zur kontinuierlich betriebenen zwischenabtrennung des bei der koppelproduktfreien oxiransynthese entstehenden oxirans unter verwendung einer trennwandkolonne

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 99811928.8

Country of ref document: CN

AK Designated states

Kind code of ref document: A1

Designated state(s): AL AU BG BR BY CA CN CZ GE HR HU ID IL IN JP KR KZ LT LV MK MX NO NZ PL RO RU SG SI SK TR UA US ZA

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
WWE Wipo information: entry into national phase

Ref document number: PA/a/2001/001248

Country of ref document: MX

ENP Entry into the national phase

Ref document number: 2339710

Country of ref document: CA

Ref document number: 2339710

Country of ref document: CA

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 2001/01003

Country of ref document: ZA

Ref document number: 200101003

Country of ref document: ZA

Ref document number: IN/PCT/2001/173/CHE

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 09762290

Country of ref document: US

Ref document number: 1020017001629

Country of ref document: KR

WWE Wipo information: entry into national phase

Ref document number: 1999942819

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1999942819

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1020017001629

Country of ref document: KR

WWG Wipo information: grant in national office

Ref document number: 1999942819

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1020017001629

Country of ref document: KR