WO2002048130A1 - Verfahren zur hydrierung von maleinsäureanhydrid und verwandten verbindungen in einem wirbelschichtreaktor - Google Patents
Verfahren zur hydrierung von maleinsäureanhydrid und verwandten verbindungen in einem wirbelschichtreaktor Download PDFInfo
- Publication number
- WO2002048130A1 WO2002048130A1 PCT/EP2001/014395 EP0114395W WO0248130A1 WO 2002048130 A1 WO2002048130 A1 WO 2002048130A1 EP 0114395 W EP0114395 W EP 0114395W WO 0248130 A1 WO0248130 A1 WO 0248130A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- catalyst
- hydrogenation
- hydrogen
- oxide
- starting material
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D307/08—Preparation of tetrahydrofuran
Definitions
- the present invention relates to a process for the preparation of optionally alkyl-substituted ⁇ -butyrolactone and tetrahydrofuran by catalytic hydrogenation in the gas phase of substrates which are selected from the group consisting of maleic acid and succinic acid and derivatives of these acids.
- substrates which are selected from the group consisting of maleic acid and succinic acid and derivatives of these acids.
- this includes esters and anhydrides, which, like the acids, can have one or more alkyl substituents.
- the reaction is carried out in a fluidized bed reactor.
- GBL and THF are maleic acid itself, succinic acid and its anhydride and the esters of these acids. If GBL and THF are to be prepared which have alkyl substituents, it is advisable to use the acids mentioned above , Esters and anhydrides to use the corresponding alkyl-substituted species.
- the catalysts used according to US 5,072,009 correspond to the general formula CuiZn b Al o M d O x , in which M is at least one element which is selected from the group consisting of groups IIA and III A, VA, VIII, Ag, Au , Groups IIIB to VIIB as well as lanthanides and actinides of the Periodic Table of the Elements; b is a number between 0.001 and 500, c a number between 0.001 and 500 and d a number from 0 to ⁇ 200 and x corresponds to the number of oxygen atoms that are necessary according to the valence criteria.
- EP-A 0 404 408 discloses a catalyst for the MSA hydrogenation, the catalytically active material of which essentially corresponds to the material disclosed in the above-cited US 5,072,009. It is used on a carrier and is used as a coated catalyst and not as a full catalyst.
- a two-stage catalyst system for the hydrogenation of MA is described in US Pat. No. 5,149,836.
- the catalyst for the first stage is chrome-free, the catalyst for the second stage is based on Cu-Zn-Cr oxides.
- chromium-containing catalysts Due to the acute toxicity, newer technologies are increasingly moving away from the use of chromium-containing catalysts. Examples of chromium-free catalyst systems can be found in the publications WO 99/35139 (Cu-Zn-oxide), WO 95/22539 (Cu-Zn-Zr) and US Pat. No. 5,122,495 (Cu-Zn-Al oxide).
- a catalyst composed exclusively of Cu and Al oxides for the MA gas phase hydrogenation to GBL is disclosed in WO 97/24346.
- the use of a similar catalyst with basically the same composition as in this patent application is also disclosed in JP 2 233 631.
- the aim of this invention is to carry out the hydrogenation of MA so that the main products are THF and 1,4-butanediol in addition to little or no amounts of GBL. This is then achieved by using the mixed Cu-Al oxides Rating catalysts and achieved by observing certain reaction conditions.
- WO 91/16132 discloses a chromium-free catalyst composed of CuO, ZnO, A1 2 0 3 and, if appropriate, a processing additive which reduces the amount of hydrogen before use in the hydrogenation of MA and then activated at temperatures of> 400 ° C. These catalysts should have a long service life and should not require the usual short regeneration intervals.
- Low hydrogen / educt ratios or high educt concentrations are desirable in order to minimize the amount of hydrogen circulated and to facilitate the condensation of the products obtained, in the case of the oxidation of MA and GBL and / or THF. This reduces the proportion of the product circulating in the hydrogenation circuit, which significantly reduces subsequent reactions.
- the object of the present invention is to provide a process for the hydrogenation of maleic acid and / or succinic acid and / or the above-mentioned derivatives, with which the lowest possible hydrogen / starting material ratios can be set, without premature deactivation and reduction the selectivity of the catalyst used occurs through decomposition products.
- This object is achieved by a process of hydrogenation in the gas phase of C 4 dicarboxylic acids and / or their derivatives, characterized in that the reaction is carried out in a fluidized bed reactor.
- the educt is fed into the fluidized bed in liquid form.
- C 4 -dicarboxylic acids and / or their derivatives are understood in relation to the present application to be maleic acid and succinic acid, which may have one or more C 1 -C 6 -alkyl substituents, and the anhydrides and esters of these optionally alkyl-substituted acids.
- An example of such an acid is citraconic acid.
- active catalyst compositions which are known for the hydrogenation of MA or a related compound are suitable as active compositions for the catalysts used in the process according to the invention.
- a prerequisite for suitability in the process according to the invention is sufficient mechanical abrasion resistance.
- Preferred catalysts are those based on copper oxide which contain at least one further metal from the group consisting of Al, Si, Zn, La, Ce, the elements of groups IIIA to VIIIA and groups IA and ILA. or a compound thereof, preferably an oxide.
- the group of the periodic table of the elements is designated according to the old IUPAC nomenclature. It is more preferred if the catalyst contains copper oxide and a further metal which is selected from the group consisting of Al, Si, Ti, Zn, Zr, La, Ce and or a compound thereof, preferably an oxide. In particular, the catalyst is a combination of copper oxide with A1 2 0 3; ZnO and / or Si0 2 .
- the amount of Cu or its compounds, especially the oxide is ⁇ 10% by weight, preferably ⁇ 25% by weight. All other components mentioned above are present in amounts ⁇ 90% by weight, preferably ⁇ 75% by weight.
- the catalysts made from the above-mentioned materials are brought into a form in a manner known per se which is suitable for use as a fluidized bed. These forms are known to the person skilled in the art, powders preferably being used. It is more preferred if the catalyst powder is used in the form of fine particles with an average particle diameter of 10 to 1000 ⁇ m, in particular 50 to 500 ⁇ m.
- the catalysts are prepared using methods known to those skilled in the art. Processes in which the copper oxide is finely divided and intimately mixed with the other constituents are preferred. This can preferably be achieved by precipitation reactions. Copper compounds dissolved in a solvent are precipitated with a precipitant in the presence of further metal compounds which are soluble or suspended in the solvent, filtered off, washed, dried and optionally calcined. For example, the corresponding metal carbonates and / or hydroxides can be precipitated in aqueous solution, filtered off, washed, dried and optionally calcined. The metal carbonates or hydroxides can be obtained, for example, by dissolving the corresponding metal salts in water and adding sodium carbonate solution.
- nitrates, sulfates, chlorides, acetates and / or oxalates are used as metal salts.
- the calcined catalyst is comminuted and sieved. However, it is also possible to sieve the dried catalyst precursor and then to calcine it.
- Another possibility for producing the catalyst is to coat a support which is already in powder form with copper oxide and possibly other constituents. Support materials known to the person skilled in the art such as, for example, silicon oxide, aluminum oxide, silicon carbide or titanium dioxide with an average particle diameter of between 10 and 100 ⁇ m are suitable for this purpose.
- the allocation of the carrier material with Copper oxide and optionally other components can be carried out by impregnating the support with a solution of the metal salts in, for example, water.
- the carrier is then dried and calcined to convert the metal salts to the oxides.
- nitrates, sulfates, chlorides, acetates and / or oxalates are used as metal salts.
- the starting material that is to say the corresponding C-dicarboxylic acid or the derivative thereof, preferably MA
- the hydrogen can be introduced in pure form or in a mixture with other gaseous components.
- additional components have a favorable effect on the selectivity, activity and / or long-term stability, depending on the implementation of Reaon.
- examples of other components are water vapor, hydrocarbons such as methane, ethane and n-butane, and carbon monoxide. In general, however, the use of pure hydrogen is preferred.
- the starting material to be hydrogenated is fed into the fluidized bed in liquid form.
- the starting material used which can be solid or liquid
- a previous melting is necessary, for example MA is used as the melt.
- MA is used as the melt.
- a number of certain advantages result from this reaction management. This is, for example, the possibility of setting high educt concentrations.
- no apparatus for evaporating the educt or for stripping the educt, in particular MA is necessary after its production.
- the ratio of hydrogen to the C -dicarboxylic acid used as starting material or its derivatives, preferably MA, can be adjusted to values of 10 to 200 using the fluidized bed catalyst used according to the invention.
- the ratio is preferably from 20 to 100.
- the concentration of starting material can be set to values from 0.5 to 10% by volume, preferably 1 to 8% by volume. It has been shown that even low hydrogen / starting material ratios of about 10 and starting material inlet concentration of 10% by volume, which are usually not chosen, can be used when using a fluidized bed catalyst.
- the catalyst which is in the form of a powder, is mixed with the input mixture which may be mixed with other components.
- the liquid educt ie a suitable C 4 - dicarboxylic acid or its derivative
- a two-component nozzle is preferably used for this purpose, with which the starting material is atomized with a hydrogen stream as a mist.
- MSA is preferably used as the starting material.
- the liquid educt evaporates, using the heat of the hydrogenation reaction.
- the maximum possible educt inlet concentration is not limited by the saturation limit of the vapor pressure.
- the hydrogenation can be carried out with hydrogen / starting material ratios of up to 10, ie starting material input concentrations of 10% by volume. If the initial concentration of the starting material is increased to values> 10% by volume or the hydrogen / starting material ratio is reduced to values which are significantly below 10, there is a risk that the catalyst will be wetted with liquid in the entire fluidized bed area and become higher there form boiling components.
- the process according to the invention can also be carried out at hydrogen / starting material ratios which are above the above-mentioned value of 200; however, such high hydrogen concentrations are generally not used because of the high gas quantities to be circulated and the associated costs.
- the hydrogenation process according to the invention is carried out at temperatures of 200 to 400 ° C., preferably 200 ° C. to 300 ° C.
- the pressures range from 1 to 100 bar, preferably 1 to 50 bar.
- WHSV Weight Hourly Space Velocity
- the WHSV will preferably be set to values of 0.01 to 1.0 kg of educt / hl of cat , in particular 0.05 to 0.5 kg of educt / hl of cat .
- the product mixture is separated using measures known to the person skilled in the art and the product obtained is worked up. Part of the unreacted hydrogen is preferably circulated and used again in the hydrogenation.
- the hydrogenation was carried out in a glass fluidized bed reactor heated with circulating oil.
- 65 to 130 ml of a powder ground catalyst consisting of 60% CuO and 40% A1 2 0 3 (sieve fraction between 0.1 and 0.2 mm) were introduced as the catalyst and, before the start of the reaction at 180 ° C. under normal pressure, with a N 2 / H 2 mixture reduced.
- the pressure was increased to 3 or 5 bar under pure hydrogen and the reaction temperature was set.
- Liquid MSA was fed directly into the fluidized bed, about 20 mm above the inflow floor. For better distribution of the educts, 20 Nl / h of hydrogen were fed into the fluidized bed through the annular gap.
- the main hydrogen flow of 80 to 160 Nl / h was fed in through the distributor plate.
- a melt of 10% by weight of maleic acid (MS) and 90% by weight of MSA was fed into the fluidized bed.
- the catalyst used in Examples 1 to 8 was used as the catalyst.
- the hydrogenation was carried out under identical conditions with pure MSA.
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20037007717A KR20030055344A (ko) | 2000-12-11 | 2001-12-07 | 유동층 반응기 내에서의 말레산 무수물 및 관련 화합물의수소화 방법 |
US10/450,114 US6958404B2 (en) | 2000-12-11 | 2001-12-07 | Method for the hydrogenation of maleic anhydride and related compounds in a fluid bed reactor |
EP01984810A EP1349845A1 (de) | 2000-12-11 | 2001-12-07 | Verfahren zur hydrierung von maleinsäureanhydrid und verwandten verbindungen in einem wirbelschichtreaktor |
JP2002549661A JP2004525093A (ja) | 2000-12-11 | 2001-12-07 | 流動床反応器中での無水マレイン酸及び関連化合物の水素化法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10061558A DE10061558A1 (de) | 2000-12-11 | 2000-12-11 | Verfahren zur Hydrierung von Maleinsäureanhydrid und verwandten Verbindungen in einem Wirbelschichtreaktor |
DE10061558.9 | 2000-12-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002048130A1 true WO2002048130A1 (de) | 2002-06-20 |
Family
ID=7666618
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2001/014395 WO2002048130A1 (de) | 2000-12-11 | 2001-12-07 | Verfahren zur hydrierung von maleinsäureanhydrid und verwandten verbindungen in einem wirbelschichtreaktor |
Country Status (8)
Country | Link |
---|---|
US (1) | US6958404B2 (de) |
EP (1) | EP1349845A1 (de) |
JP (1) | JP2004525093A (de) |
KR (1) | KR20030055344A (de) |
CN (1) | CN1237057C (de) |
DE (1) | DE10061558A1 (de) |
MY (1) | MY127165A (de) |
WO (1) | WO2002048130A1 (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003093256A1 (de) * | 2002-04-30 | 2003-11-13 | Basf Aktiengesellschaft | Verfahren zur herstellung von gamma-butyrolacton |
US9234220B2 (en) | 2008-01-16 | 2016-01-12 | Evonik Degussa Gmbh | Process for heterogeneously catalyzed preparation of carboxylic acid derivatives |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10357715A1 (de) * | 2003-12-09 | 2005-07-14 | Basf Ag | Verfahren zur Herstellung von definierten Gemischen aus THF, BDO und GBL durch Gasphasenhydierung |
DE10357717A1 (de) * | 2003-12-09 | 2005-07-14 | Basf Ag | Katalysatorextrudate auf Basis Kupferoxid und ihre Verwendung zur Hydrierung von Carbonylverbindungen |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4083809A (en) * | 1976-08-20 | 1978-04-11 | Gaf Corporation | Hydrogenation catalyst and method of producing same |
US4301077A (en) * | 1980-12-22 | 1981-11-17 | Standard Oil Company | Process for the manufacture of 1-4-butanediol and tetrahydrofuran |
EP0322140A1 (de) * | 1987-12-23 | 1989-06-28 | The Standard Oil Company | Dampfphasenhydrierung von Maleinsäureanhydrid zu Tetrahydrofuran und Gamma-Butyrolacton |
US5122495A (en) * | 1991-10-02 | 1992-06-16 | Isp Investments Inc. | Activated catalyst for the vapor phase hydrogenation of maleic anhydride to gamma-butyrolactone in high conversion and high selectivity |
US5149836A (en) * | 1991-07-25 | 1992-09-22 | Isp Investments Inc. | Process for the production of gamma butyrolactone THF in predetermined amounts |
US5326889A (en) * | 1989-12-07 | 1994-07-05 | Tonen Corporation | Process for producing 1,4-butanediol and tetrahydrofuran |
US5347021A (en) * | 1990-04-16 | 1994-09-13 | Isp Investments Inc. | Process of vapor phase catalytic hydrogenation of maleic anhydride to gamma-butyrolactone in high conversion and high selectivity using an activated catalyst |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
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US3065243A (en) | 1962-11-20 | Reduction of dicarboxylic acid esters | ||
DE1668348A1 (de) | 1966-12-29 | 1972-03-30 | Kao Corp | Verfahren zur Herstellung von gamma-Butyrolacton |
US4001282A (en) * | 1973-02-12 | 1977-01-04 | General Electric Company | Process for producing gamma-butyrolactone |
US4006165A (en) | 1973-08-03 | 1977-02-01 | Deutsche Texaco Aktiengesellschaft | Process for converting maleic anhydride to γ-butyrolactone |
US5072009A (en) | 1987-12-23 | 1991-12-10 | The Standard Oil Company | Vapor-phase hydrogenation of maleic anhydride to tetrahydrofuran and gamma-butyrolactone |
JP2639464B2 (ja) | 1989-03-08 | 1997-08-13 | 東燃株式会社 | 1,4―ブタンジオールおよびテトラヒドロフランの製法 |
US5055599A (en) | 1989-06-23 | 1991-10-08 | The Standard Oil Company | Process for the hydrogenation of maleic anhydride to tetrahydrofuran and gamma-butyrolactone |
US5142067A (en) * | 1989-12-21 | 1992-08-25 | Union Carbide Chemicals & Plastics Technology Corporation | Hydrogenation with Cu-Al-X catalysts |
US5041564A (en) * | 1990-04-16 | 1991-08-20 | Gaf Chemicals Corporation | Vapor phase process for production of gamma-butyrolactone |
US5536845A (en) | 1990-06-27 | 1996-07-16 | Atochem | Acrylates containing an alcohol, aldehyde and/or ether functional group, process for their manufacture and their application to the production of new polymers and copolymers |
DE4326692A1 (de) | 1993-08-10 | 1995-02-16 | Akzo Nobel Nv | Verfahren zur Herstellung von gamma-Butyrolacton |
IT1273320B (it) | 1994-02-22 | 1997-07-08 | Alusuisse Italia Spa | Procedimento per la produzione di gamma-butirrolattone |
TW341568B (en) | 1995-12-27 | 1998-10-01 | Akzo Nobel Nv | Process for manufacturing Gamma-butyrolactone and its use |
IT1298096B1 (it) | 1998-01-09 | 1999-12-20 | Lonza Spa | Procedimento per la produzione di gamma-butirrolattone |
IT1298535B1 (it) | 1998-02-02 | 2000-01-12 | Lonza Spa | Procedimento per la produzione di gamma-butirrolattone |
-
2000
- 2000-12-11 DE DE10061558A patent/DE10061558A1/de not_active Withdrawn
-
2001
- 2001-12-07 WO PCT/EP2001/014395 patent/WO2002048130A1/de active Application Filing
- 2001-12-07 JP JP2002549661A patent/JP2004525093A/ja active Pending
- 2001-12-07 KR KR20037007717A patent/KR20030055344A/ko not_active Application Discontinuation
- 2001-12-07 EP EP01984810A patent/EP1349845A1/de not_active Withdrawn
- 2001-12-07 US US10/450,114 patent/US6958404B2/en not_active Expired - Fee Related
- 2001-12-07 CN CNB018204295A patent/CN1237057C/zh not_active Expired - Fee Related
- 2001-12-10 MY MYPI20015603A patent/MY127165A/en unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4083809A (en) * | 1976-08-20 | 1978-04-11 | Gaf Corporation | Hydrogenation catalyst and method of producing same |
US4301077A (en) * | 1980-12-22 | 1981-11-17 | Standard Oil Company | Process for the manufacture of 1-4-butanediol and tetrahydrofuran |
EP0322140A1 (de) * | 1987-12-23 | 1989-06-28 | The Standard Oil Company | Dampfphasenhydrierung von Maleinsäureanhydrid zu Tetrahydrofuran und Gamma-Butyrolacton |
US5326889A (en) * | 1989-12-07 | 1994-07-05 | Tonen Corporation | Process for producing 1,4-butanediol and tetrahydrofuran |
US5347021A (en) * | 1990-04-16 | 1994-09-13 | Isp Investments Inc. | Process of vapor phase catalytic hydrogenation of maleic anhydride to gamma-butyrolactone in high conversion and high selectivity using an activated catalyst |
US5149836A (en) * | 1991-07-25 | 1992-09-22 | Isp Investments Inc. | Process for the production of gamma butyrolactone THF in predetermined amounts |
US5122495A (en) * | 1991-10-02 | 1992-06-16 | Isp Investments Inc. | Activated catalyst for the vapor phase hydrogenation of maleic anhydride to gamma-butyrolactone in high conversion and high selectivity |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003093256A1 (de) * | 2002-04-30 | 2003-11-13 | Basf Aktiengesellschaft | Verfahren zur herstellung von gamma-butyrolacton |
US9234220B2 (en) | 2008-01-16 | 2016-01-12 | Evonik Degussa Gmbh | Process for heterogeneously catalyzed preparation of carboxylic acid derivatives |
Also Published As
Publication number | Publication date |
---|---|
KR20030055344A (ko) | 2003-07-02 |
MY127165A (en) | 2006-11-30 |
CN1479733A (zh) | 2004-03-03 |
EP1349845A1 (de) | 2003-10-08 |
CN1237057C (zh) | 2006-01-18 |
US20040044230A1 (en) | 2004-03-04 |
US6958404B2 (en) | 2005-10-25 |
JP2004525093A (ja) | 2004-08-19 |
DE10061558A1 (de) | 2002-06-13 |
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