WO2007135072A1 - Verfahren zur vermeidung von fumarsäureablagerungen bei der herstellung von maleinsäureanhydrid - Google Patents
Verfahren zur vermeidung von fumarsäureablagerungen bei der herstellung von maleinsäureanhydrid Download PDFInfo
- Publication number
- WO2007135072A1 WO2007135072A1 PCT/EP2007/054788 EP2007054788W WO2007135072A1 WO 2007135072 A1 WO2007135072 A1 WO 2007135072A1 EP 2007054788 W EP2007054788 W EP 2007054788W WO 2007135072 A1 WO2007135072 A1 WO 2007135072A1
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- WO
- WIPO (PCT)
- Prior art keywords
- absorbent
- phthalate
- hydrogenation
- maleic anhydride
- reactors
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/573—Separation; Purification; Stabilisation; Use of additives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
Definitions
- the present invention relates to methods of preventing fumaric acid deposits in the production of maleic anhydride (MSA) by absorbing MSA from a crude product mixture into an organic solvent or water as an absorbent, then separating MSA from the absorbent and recovering the absorbent or partial stream so recovered the same catalytically hydrogenated and wholly or partly recycled to the absorption stage (a).
- MSA maleic anhydride
- the inventive method is used to improve the industrial production of maleic anhydride.
- Maleic anhydride is a valuable starting material, a basic material for polymers or is used for the hydrogenation of MSA via the intermediate succinic anhydride (BSA) to produce gamma-butyrolactone (GBL), butanediol (BDO) and tetrahydrofuran (THF).
- BSA succinic anhydride
- GBL gamma-butyrolactone
- BDO butanediol
- THF tetrahydrofuran
- Maleic anhydride can be obtained by partial oxidation of hydrocarbons such as butane or benzene. From the maleic anhydride-containing exhaust gas of the partial oxidation, the desired product is usually absorbed in a solvent. In addition to MSA, other components contained in the oxidation exhaust gas are absorbed, such as water. Water reacts with maleic anhydride to form maleic acid, which in turn isomerizes to fumaric acid. Fumaric acid is a very poorly soluble in water or organic solvents diacid, which forms deposits and thereby clogging plant parts such as columns, heat exchangers, pumps, pipes and the like.
- WO 96/29323 describes washing the fumaric acid-containing absorbent with an aqueous extractant so as to avoid deposits.
- a disadvantage of this method is the high cost, which is necessary to mix the wash water in a large-scale plant for the production of C4-dicarboxylic acids or their derivatives and to separate the phases again.
- the inevitable loss of valuable product and solvent makes the process uneconomical.
- the addition of water to the process further enhances fumaric acid formation.
- the object of the present invention was to prevent fumaric acid deposits on plant parts and thereby causing to avoid clogging, removal and cleaning work and shutdowns in the process for the production of C4-dicarboxylic acids and / or their derivatives.
- the thus recovered absorbent completely or partially catalytically hydrogenated and wholly or partially recycled to the absorption stage (a).
- a partial stream is hydrogenated and completely recycled to the absorption stage (a).
- the process according to the invention avoids the abovementioned disadvantages by hydrogenating fumaric acid present in the absorbent on a hydrogenation catalyst with hydrogen to succinic acid.
- a hydrogenation catalyst with hydrogen to succinic acid.
- high selectivities are achieved at low pressures and small amounts of catalyst to be used.
- fumaric acid deposits already formed in pipelines or other parts of the plant will be replaced again.
- the hydrogenation process of the invention may comprise an upstream step comprising producing MSA by partial oxidation of a suitable hydrocarbon.
- suitable hydrocarbon streams are benzene, C4 olefins (eg n-butenes, C4 raffinate streams) or n-butane. Particular preference is given to the use of n-butane, since it represents a low-cost, economical starting material. Processes for the partial oxidation of n-butane are described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 6 th Edition, Electronic Release, Maleic and Fumaric Acids-Maleic Anhydrides.
- the reaction product thus obtained, the crude product mixture, is then taken up in water or preferably in a suitable organic solvent as an absorbent or a mixture thereof, wherein the organic solvent at atmospheric pressure preferably has a boiling point higher than MSA by at least 30 ° C.
- the maleic anhydride-containing gas stream from the partial oxidation can be brought into contact in many ways at pressures (absolute) of 0.8 to 10 bar and temperatures of 50 - 300 ° C in one or more absorption stages with the solvent (absorbent): (i) Introducing the gas stream into the solvent (eg, via gas inlet nozzles or gassing rings), (ii) spraying the solvent into the gas stream, and (iii) countercurrent contact between the upwardly flowing gas stream and the downwardly flowing solvent in a bottom or packing column.
- the apparatus known to those skilled in the gas absorption can be used.
- Suitable absorbents are: tricresyl phosphate, dibutyl maleate, butyl maleate, high molecular weight waxes, aromatic hydrocarbons having a molecular weight between 150 and 400 and a boiling point above 140 ° C, such as dibenzylbenzene; Alkyl phthalates and dialkyl phthalates having C 1 -C 6 -alkyl groups, for example dimethyl phthalate, diethyl phthalate, dibutyl phthalate, di-n-propyl and diisopropyl phthalate, undecyl phthalate, diundecyl phthalate, methyl phthalate, ethyl phthalate, butyl phthalate, n-propyl or iso - Propyl phthalate; Di-C 1 -C 4 -alkyl
- the resulting solution after treatment with the absorbent generally has an MSA content of about 5 to 400 grams per liter.
- the waste gas stream remaining after the treatment with the absorption medium contains, in addition to water, mainly the by-products of the preceding partial oxidation, such as carbon monoxide, carbon dioxide, unreacted butanes, acetic and acrylic acid.
- the exhaust stream is virtually free of MSA.
- the dissolved MSA is expelled or separated from the absorbent.
- This can be done with hydrogen at or at most 10% above the pressure of a subsequent hydrogenation of MSA to THF, BDO, or GBL preferably at 100 to 250 ° C and pressures (absolute) from 0.8 to 30 bar.
- a temperature profile is observed which results from the boiling points of MSA at the top and the almost MSA-free absorbent at the bottom of the column at the respective column pressure and the dilution with carrier gas (in the first case with hydrogen).
- rectification installations may be located above the feed of the crude MSA stream.
- the MSA dissolved in the absorbent may be separated in a distillation unit at pressures generally from 0.01 to 5 bar and temperatures from 65 to 300 ° C.
- the distillation can in this case in one stage or more stages, for example in separation apparatuses with one stage or multiple stages, such as columns with multiple separation stages, for example rectification columns, packed columns, bubble capped columns or packed columns.
- the recovered, withdrawn from the bottom of the distillation unit or the stripping, almost MSA-free absorbent is now fed to the hydrogenation of the invention and preferably at temperatures between 20 and 300 ° C, more preferably 60 to 270 ° C and particularly preferably 100 to 250 ° C and at pressures (absolute values) of preferably 0.1 to 300 bar, more preferably at 0.5 to 50 bar, particularly preferably at 0.8 to 20 bar, hydrogenated on a hydrogenation catalyst.
- the content of fumaric acid recovered in step b) (total amount of homogeneously dissolved and suspended fumaric acid present) prior to the hydrogenation step according to the invention usually 0.01 to 5 wt .-%.
- the recovered absorbent has a content of between 0.02 and 2% by weight of fumaric acid.
- the molar amount of hydrogen for the hydrogenation step according to the invention is generally chosen so that at least one mole of hydrogen per mole of fumaric acid is present. However, an excess of hydrogen is not critical. In this case, the hydrogen may be dissolved, in addition, gaseous hydrogen may be present.
- the fumaric acid content is generally below 0.1% by weight, preferably below 0.05% by weight. The fumaric acid content should only be so high that at a given temperature there is a homogeneous solution.
- the process according to the invention can be carried out batchwise, semi-continuously or continuously. Continuous performance is preferred.
- the hydrogenation is carried out in the liquid phase on heterogeneous catalysts, which may be fixed or suspended, with fixed catalysts (fixed bed catalysts) are preferred.
- the usable catalysts contain at least one metal from the 7th, the 8th, the 9th, the 10th or the 1st 1st group of the Periodic Table of the Elements or their compounds such as oxides.
- the catalysts which can be used according to the invention more preferably contain at least one element selected from the group consisting of Re, Fe, Ru, Co, Rh, Ir, Ni, Pd, Pt, Cu and Au.
- the catalysts which can be used according to the invention comprise at least one element selected from the group consisting of Ni, Pd, Pt, Ru and Cu.
- the catalysts which can be used according to the invention furthermore preferably contain Pd, Pt, Ru or Ni.
- At least one heterogeneous catalyst is suitable, wherein at least one of the abovementioned metals (active metals) can be used as metal as such, as Raney catalyst and / or applied to a conventional support. If two or more active metals are used, they may be present separately or as an alloy. In this case, it is possible to use at least one metal as such and at least one other metal as Raney catalyst or at least one metal as such and at least one other metal applied to at least one support, or at least one metal as Raney catalyst and at least one other metal applied to at least one support, or at least one metal as such and at least one metal other than Raney's catalyst and at least one other metal applied to at least one support.
- active metals active metals
- the catalysts used may, for example, also be so-called precipitation catalysts.
- Such catalysts can be prepared by reacting their catalytically active components from their salt solutions, in particular from the solutions of their nitrates and / or acetates, for example by adding solutions of alkali metal and / or alkaline earth metal hydroxide and / or carbonate solutions, For example, poorly soluble hydroxides, oxide hydrates, basic salts or carbonates precipitates, the resulting precipitates then dried and then calcination at generally 300 to 700 ° C, in particular 400 to 600 ° C in the corresponding oxides, mixed oxides and / or mixed valentigen oxides converted by a treatment with hydrogen or hydrogen-containing gases in the range of generally 50 to 700 ° C, in particular 100 to 400 ° C to the respective metals and / or oxidic compounds lower oxidation state reduced and in the actual catalytically active Form are transferred.
- the precipitation of the catalytically active components can be carried out in the presence of the relevant support material.
- the catalytically active components can advantageously be precipitated from the relevant salt solutions simultaneously with the support material.
- Hydrogenation catalysts are preferably used which contain the hydrogenation-catalyzing metals or metal compounds deposited on a support material.
- such carrier materials are generally suitable for the process according to the invention, in which the catalytically hydrating component has been applied to a carrier material, for example by impregnation.
- the manner of applying the catalytically active metal to the support is generally not critical and can be accomplished in a variety of ways.
- the catalytically active metals can be applied to these support materials, for example, by impregnation with solutions or suspensions of the salts or oxides of the elements concerned, drying and subsequent reduction of the metal compounds to the respective metals or compounds of lower oxidation state by means of a reducing agent, preferably with hydrogen or complex hydrides ,
- a reducing agent preferably with hydrogen or complex hydrides
- Another possibility for applying the catalytically active metals to these supports is to impregnate the supports with solutions of easily decomposable salts, for example nitrates or thermally easily decomposable complex compounds, for example carbonyl or hydrido complexes of the catalytically active metals, and to heat the thus impregnated support for thermal decomposition of the adsorbed metal compounds to temperatures in the range of 300 to 600 ° C.
- This thermal decomposition is preferably carried out under a protective gas atmosphere.
- Suitable shielding gases are, for example, nitrogen, carbon dioxide, hydrogen or the noble gases.
- the catalytically active metals can be deposited on the catalyst support by vapor deposition or by flame spraying.
- the content of these supported catalysts on the catalytically active metals is in principle not critical to the success of the process according to the invention. In general, higher levels of catalytically active metals of these supported catalysts result in higher space-time conversions than lower levels.
- supported catalysts are used whose content of catalytically active metals in the range of 0.01 to 90 wt .-%, preferably in the range of 0.1 to 40 wt .-% based on the total weight of the catalyst.
- these content data refer to the entire catalyst including carrier material, but the different carrier materials have very different specific weights and specific surface areas, it is also conceivable that these specifications can be exceeded or exceeded, without adversely affecting the result of the process according to the invention.
- the catalytically active metals may be applied to the respective carrier material.
- the catalytically active metals can be applied to the carrier, for example, by the process of DE-A 25 19 817, EP-A 1 477 219 or EP-A 0 285 420.
- the catalytically active metals are present as alloys which are produced by thermal treatment and / or reduction of, for example, by impregnation of the support material with a salt or complex of the abovementioned metals.
- chromium-containing catalysts Due to the toxicity of chromium-containing catalysts, preference is given to using chromium-free catalysts.
- chromium-free catalysts are also suitable for use in the process according to the invention, which, however, does not give rise to the desired advantages, which are particularly of environmental and operational nature.
- Both the activation of the precipitation catalysts and of the supported catalysts can also be carried out in situ at the beginning of the reaction by the hydrogen present. Preferably, these catalysts are activated separately before use.
- the oxides of aluminum and titanium, zirconium dioxide, silica, clays such as montmorillonites, bentonites, silicates such as magnesium or aluminum silicates, zeolites such as the structural types ZSM-5 or ZSM-10, or Activated carbon can be used.
- Preferred support materials are aluminum oxides, titanium dioxides, silicon dioxide, zirconium dioxide and activated carbon.
- mixtures of different carrier materials can also serve as carriers for catalysts which can be used in the process according to the invention.
- metallic supports on which the hydrogenation-active metal has been deposited for example Cu on the e.g. Pd, Pt or Ru was separated from the corresponding metal salts dissolved in water.
- catalysts according to the invention are supported catalysts which contain Ni, Pt and / or Pd, particular preferred supports being activated carbon, aluminum oxide, titanium dioxide and / or silicon dioxide or mixtures thereof.
- An inventively employable heterogeneous catalyst can be used as a suspension catalyst and / or as a fixed bed catalyst in the process according to the invention.
- the hydrogenation step according to the invention is preferably carried out in one or more separate reactors.
- the separate hydrogenation reactor for the hydrogenation stage of the process according to the invention is fed with exhaust gas hydrogen from the MSA hydrogenation to BSA, GBL, THF and / or BDO.
- the hydrogenation according to the invention can also take place within the stripping column for separating the MSA from the absorbent.
- the stripping column preferably in the lower part, where the MSA concentration is already below 1% by weight, has a fixed bed catalyst, e.g. as a catalytic packing, on.
- the hydrogenation stage is carried out with at least one suspension catalyst
- hydrogenation is preferably carried out in at least one stirred reactor, at least one bubble column and / or a packed bubble column or in a combination of two or more identical or different reactors.
- the term "different reactors” denotes both different reactor types and reactors of the same type, which differ, for example, by their geometry, for example their volume and / or their cross-section and / or by the hydrogenation conditions in the reactors.
- the hydrogenation is carried out with at least one fixed-bed catalyst, preferably at least one tubular reactor such as at least one shaft reactor and / or at least one tube bundle reactor is used, wherein a single reactor can be operated in a bottom or trickle mode. If two or more reactors are used, at least one can be operated in a sump mode and at least one in a trickle mode.
- a heterogeneous catalyst is used as the suspension catalyst as the catalyst in the hydrogenation stage of the process according to the invention, it is preferably separated off after the hydrogenation by at least one filtration step. The thus separated catalyst can be recycled to the hydrogenation stage.
- the liberated during the hydrogenation heat is usually not dissipated. However, should this be necessary, it can be removed internally, for example via cooling coils and / or externally, for example via at least one heat exchanger in the reactor used in the invention.
- the residence time is generally in the range of 0.01 to 10 h, for example in the
- Range of 0.5 to 5 hours preferably in the range of 0.5 to 2 hours and more preferably in the range of 0.1 to 1 h. It is irrelevant whether according to the invention a main reactor and a post-reactor or in addition further reactors are used. For all of these embodiments, the total residence time is in the above ranges.
- the catalyst loading (kg feed / liter of catalyst xh) is generally in the range from 0.05 to 1000, preferably in the range from 0.1 to 500 and particularly preferably in the range from 0.5 to 100. It is irrelevant whether, according to the invention, a main reactor and a postreactor or, in addition, further reactors are used. For all of these embodiments, the total load is in the above ranges.
- feed is meant the fumaric acid-containing recovered absorbent. Other components present in the feed are, above all, those which are likewise absorbed by the solvent in the absorption stage.
- maleic acid MSA
- alkyl-substituted maleic acid derivatives such as acylacrylic acid, methacrylic acid and acetic acid.
- hydride products of the process according to the invention such as succinic acid and succinic anhydride, are present.
- succinic acid and succinic anhydride are present.
- phthalates are used, in addition to phthalic anhydride and its monoesters, the esters of the abovementioned acids are also possible.
- a partial stream of the recovered absorbent may be subjected to distillation after the hydrogenation step and prior to recycling to the absorption step a).
- succinic acid formed as a result of the hydrogenation according to the invention as such or as succinic anhydride from the absorbent can be removed by measures known to the person skilled in the art, for example by partial condensation, condensation, distillation and stripping analogously to the abovementioned MSA stripping.
- a circulating stream of 3 l / h of dibutyl phthalate was warmed to 200 ° C. at 1.2 bar in front of the distillation column and, after pressurization, was driven into the distillation column. At a column pressure of 0.2 bar absolute, the bottom temperature was 230 ° C.
- After cooling the recirculated stream taken off via a bottom outlet to 90 ° C. about 0.3 kg of MSA / h in the form of a melt and about 15 g of water / h were metered into the circuit. MSA and most of the water were distilled off via the top of the column at a reflux ratio of 1 (distillate).
- the distillate consisted mainly of MSA and small amounts of water and maleic acid.
- the apparatus was continued for a period of 4 days. On a daily sampling, a visual sample and a gas chromatographic analysis revealed that suspended solid had formed in the plant as fumaric acid. After 4 days, the pressure retention clogged and the system turned off. After emptying the circuit, fumaric acid deposits were found in the piping and heat exchangers.
- the apparatus 2a) used differs from the experimental apparatus 1 a) from Comparative Example 1 by a built after the bottom outlet of the column and before the column downstream heat exchanger 10 ml oil-heated or cooled tubular reactor with 3 mm strands of a catalyst consisting of Wt .-% palladium on activated carbon is filled and was flowed through in trickle mode.
- Example 2 according to the invention was repeated, with 0.15% by weight of palladium on alumina, in Example 4 10% by weight of Ni on activated carbon and in Example 5 of 0.15% by weight of platinum in Example 3 instead of Pd on activated carbon Alumina was used. In all examples, the same effect as in Example 2 according to the invention was obtained.
- Example 2 according to the invention was repeated, but for the first 3 days no hydrogen was fed into the reactor. Samples from the cycle had a solids content of fumaric acid after 2 days. After the third day 2 hydrogen was metered as in the inventive example in an amount of about 0.5 liter / h. On re-sampling the next day, fumaric acid could no longer be detected by visual inspection or gas chromatographic analysis. This example shows that under the conditions of the invention, once formed fumaric acid, which has already been deposited, can also be hydrogenated.
- the pressure equipment used consists of a feed for the MSA melt and a water supply before a circulation pump and a hydrogen-operated stripping column (stripper) for separating the MSA between two heat exchangers and a pressure maintenance.
- the temperature in all parts of the system was at least 70 ° C due to heat tracing.
- a circulating stream of 1, 51 / h dibutyl phthalate was introduced into the stripper at 200 ° C via a pressure maintenance (about 10 bar absolute). Hydrogen was injected at a temperature of about 150 ° C. into the bottom of the stripper filled with 5 mm silica rings at 9 bar (absolute) 1.5 Nm 3 / h. After cooling the recirculation stream taken from the stripper to 90 ° C. via a bottom outlet, 0.1 kg of MSA / h in the form of a melt and about 5 g of water / h were metered into the circuit.
- the top product of the stripper (hydrogen, MSA and small amounts of dibutyl phthalate) were hydrogenated to THF on a Cu / alumina catalyst at 230-260 ° C. and 9 bar in a tubular reactor in a manner known per se.
- the pressure apparatus 8a) used differs from the experimental apparatus 7a) of Comparative Example 7 in that the riser rings in the lower area of the stripper were replaced by 50 ml of 0.15% by weight of palladium on aluminum oxide.
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- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP07729236A EP2029565A1 (de) | 2006-05-24 | 2007-05-16 | Verfahren zur vermeidung von fumarsäureablagerungen bei der herstellung von maleinsäureanhydrid |
JP2009511478A JP2009537592A (ja) | 2006-05-24 | 2007-05-16 | 無水マレイン酸の製造の際にフマル酸堆積を回避するための方法 |
CN2007800187745A CN101448808B (zh) | 2006-05-24 | 2007-05-16 | 防止富马酸在马来酸酐生产中沉积的方法 |
CA002647083A CA2647083A1 (en) | 2006-05-24 | 2007-05-16 | Method for preventing fumaric acid deposits in the production of maleic acid anhydride |
US12/300,571 US20090143601A1 (en) | 2006-05-24 | 2007-05-16 | Method for preventing fumaric acid deposits in the production of maleic acid anhydride |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102006024903A DE102006024903A1 (de) | 2006-05-24 | 2006-05-24 | Verfahren zur Vermeidung von Fumarsäureablagerungen bei der Herstellung von Maleinsäureanhydrid |
DE102006024903.8 | 2006-05-24 |
Publications (1)
Publication Number | Publication Date |
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WO2007135072A1 true WO2007135072A1 (de) | 2007-11-29 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/EP2007/054788 WO2007135072A1 (de) | 2006-05-24 | 2007-05-16 | Verfahren zur vermeidung von fumarsäureablagerungen bei der herstellung von maleinsäureanhydrid |
Country Status (9)
Country | Link |
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US (1) | US20090143601A1 (de) |
EP (1) | EP2029565A1 (de) |
JP (1) | JP2009537592A (de) |
KR (1) | KR20090034817A (de) |
CN (1) | CN101448808B (de) |
CA (1) | CA2647083A1 (de) |
DE (1) | DE102006024903A1 (de) |
RU (1) | RU2458057C2 (de) |
WO (1) | WO2007135072A1 (de) |
Families Citing this family (3)
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CN101981018B (zh) | 2008-04-01 | 2013-07-24 | 巴斯夫欧洲公司 | 在马来酸酐的生产期间分离出富马酸和其它次要组分的方法 |
EP2595974B1 (de) | 2010-12-13 | 2016-03-09 | Conser S.P.A. | Verbessertes verfahren zur rückgewinnung von maleinsäureanhydrid mit einem organischen lösungsmittel |
RU2603777C1 (ru) * | 2015-11-11 | 2016-11-27 | Федеральное государственное бюджетное учреждение науки Институт катализа им. Г.К. Борескова Сибирского отделения Российской академии наук | Палладиевый катализатор, способ его приготовления и способ получения янтарной кислоты |
Citations (3)
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WO1996029323A1 (en) * | 1995-03-20 | 1996-09-26 | Huntsman Petrochemical Corporation | Process and apparatus for the preparation and recovery of maleic anhydride |
EP0897905A2 (de) * | 1997-07-22 | 1999-02-24 | Mitsubishi Chemical Corporation | Verfahren zur Herstellung von Maleinsäureanhydrid |
WO2002085834A1 (de) * | 2001-04-23 | 2002-10-31 | Basf Aktiengesellschaft | Verfahren zur reinigung eines organischen lösungsmittels zur absorption von maleinsäureanhydrid |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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SU537995A1 (ru) * | 1974-01-16 | 1976-12-05 | Предприятие П/Я А-7850 | Способ получени малеинового ангидрида |
DE19806038A1 (de) * | 1998-02-13 | 1999-08-19 | Basf Ag | Verfahren zur Abtrennung von Maleinsäureanhydrid aus maleinsäureanhydridhaltigen Gemischen durch Strippung |
MY139259A (en) * | 1999-10-12 | 2009-09-30 | Kvaerner Process Tech Ltd | Process |
BR0208992A (pt) * | 2001-04-20 | 2004-04-27 | Pfizer Prod Inc | Processo para a preparação de indenos 1,3-substituìdos e compostos azapolicìclicos fundidos com arila |
-
2006
- 2006-05-24 DE DE102006024903A patent/DE102006024903A1/de not_active Withdrawn
-
2007
- 2007-05-16 JP JP2009511478A patent/JP2009537592A/ja not_active Withdrawn
- 2007-05-16 KR KR1020087031268A patent/KR20090034817A/ko not_active Application Discontinuation
- 2007-05-16 RU RU2008150806/04A patent/RU2458057C2/ru not_active IP Right Cessation
- 2007-05-16 CA CA002647083A patent/CA2647083A1/en not_active Abandoned
- 2007-05-16 US US12/300,571 patent/US20090143601A1/en not_active Abandoned
- 2007-05-16 WO PCT/EP2007/054788 patent/WO2007135072A1/de active Application Filing
- 2007-05-16 EP EP07729236A patent/EP2029565A1/de not_active Withdrawn
- 2007-05-16 CN CN2007800187745A patent/CN101448808B/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996029323A1 (en) * | 1995-03-20 | 1996-09-26 | Huntsman Petrochemical Corporation | Process and apparatus for the preparation and recovery of maleic anhydride |
EP0897905A2 (de) * | 1997-07-22 | 1999-02-24 | Mitsubishi Chemical Corporation | Verfahren zur Herstellung von Maleinsäureanhydrid |
WO2002085834A1 (de) * | 2001-04-23 | 2002-10-31 | Basf Aktiengesellschaft | Verfahren zur reinigung eines organischen lösungsmittels zur absorption von maleinsäureanhydrid |
Also Published As
Publication number | Publication date |
---|---|
CA2647083A1 (en) | 2007-11-29 |
CN101448808A (zh) | 2009-06-03 |
US20090143601A1 (en) | 2009-06-04 |
JP2009537592A (ja) | 2009-10-29 |
RU2458057C2 (ru) | 2012-08-10 |
DE102006024903A1 (de) | 2007-11-29 |
CN101448808B (zh) | 2012-07-25 |
KR20090034817A (ko) | 2009-04-08 |
EP2029565A1 (de) | 2009-03-04 |
RU2008150806A (ru) | 2010-06-27 |
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