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WO2001051447A2 - Coproduction d'acides carboxyliques et/ou de leurs esters - Google Patents

Coproduction d'acides carboxyliques et/ou de leurs esters Download PDF

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Publication number
WO2001051447A2
WO2001051447A2 PCT/GB2000/004944 GB0004944W WO0151447A2 WO 2001051447 A2 WO2001051447 A2 WO 2001051447A2 GB 0004944 W GB0004944 W GB 0004944W WO 0151447 A2 WO0151447 A2 WO 0151447A2
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WO
WIPO (PCT)
Prior art keywords
liquid reaction
reaction composition
group
range
process according
Prior art date
Application number
PCT/GB2000/004944
Other languages
English (en)
Other versions
WO2001051447A3 (fr
Inventor
John Glenn Sunley
Original Assignee
Bp Chemicals Limited
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
Priority claimed from GB0000935A external-priority patent/GB0000935D0/en
Priority claimed from GB0000936A external-priority patent/GB0000936D0/en
Priority claimed from GB0000933A external-priority patent/GB0000933D0/en
Priority claimed from GB0000934A external-priority patent/GB0000934D0/en
Application filed by Bp Chemicals Limited filed Critical Bp Chemicals Limited
Priority to AU2001220161A priority Critical patent/AU2001220161A1/en
Publication of WO2001051447A2 publication Critical patent/WO2001051447A2/fr
Publication of WO2001051447A3 publication Critical patent/WO2001051447A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
    • C07C51/12—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on an oxygen-containing group in organic compounds, e.g. alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
    • C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
    • C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Definitions

  • the present invention relates in general to a carbonylation process and in particular to a co-carbonylation process in which methanol and an olefinically unsaturated carbonylatable reactant having at least two carbon atoms are carbonylated to produce a mixture of acetic acid and a carboxylic acid having three or more carbon atoms and/or esters thereof.
  • Carbonylation processes in the presence of cobalt, iron or manganese are also known and are described for example in US 4132734.
  • US 4132734 is silent with regard to the co-carbonylation of methanol and an olefinically unsaturated carbonylatable reactant having at least two carbon atoms to produce a mixture of acetic acid and a carboxylic acid having three or more carbon atoms and/or esters thereof.
  • US 5817869 relates to the production of acetic acid without the use of alkali metal halides by contacting methanol or methyl acetate with carbon monoxide in the presence of about 200 to about 1200 ppm rhodium-containing component and a liquid reaction medium comprising from about 20 to about 80 weight % acetic acid, from about 0.6 to about 36 weight % methyl iodide from about 0.5 to about 10 weight % methyl acetate, said contacting being in the presence of at least one pentavalent
  • Group VA oxide of the formula R 3 M O at a concentration of oxide : rhodium of greater than about 60 : 1, and water being added in an amount from about 4 to about 12 weight %.
  • EP-A-0114703 relates to a process for preparation of carboxylic acids and/or esters by reaction of an alcohol with carbon monoxide in the presence of a rhodium compound, an iodide and/or bromide source and a phosphorus, arsenic or antimony- containing promoter.
  • British patent GB 1406672 relates to the production of carboxylic acids from ethylenically unsaturated hydrocarbons having 2 to 30 carbon atoms by reaction with carbon monoxide in the presence of a catalyst comprising iridium or rhodium and as stabiliser a trialkylphosphine oxide, a triaryphosphine oxide, a trialkylarsine oxide, a triarylarsine oxide, a trialkylamine oxide or a trialkylstibine oxide.
  • a catalyst comprising iridium or rhodium and as stabiliser a trialkylphosphine oxide, a triaryphosphine oxide, a trialkylarsine oxide, a triarylarsine oxide, a trialkylamine oxide or a trialkylstibine oxide.
  • Research Disclosure 12820 of 1974 relates to co-production of acetic and propionic acids by introducing ethylene and water into a reactor where methanol and carbon monoxide are being reacted in the presence of rhodium.
  • US patent number US 4111982 relates to a continuous process for the production of acetic acid and propionic acids by simultaneous carbonylation of methanol and ethylene respectively, in a single reactor.
  • the catalyst system is said to consist essentially of a rhodium compound and a halogen component which is bromide, iodide a bromide or an iodide.
  • the problem to be solved by the present invention is the provision of a promoter for a rhodium carbonylation catalyst in a co-carbonylation process.
  • a solution to the problem is the use of a promoter selected from the group consisting of phosphine oxides and iodide salts such as alkali metal iodides and in particular lithium iodide, and mixtures thereof.
  • the present invention provides a process for the co-carbonylation of methanol and an olefinically unsaturated carbonylatable reactant having at least two carbon atoms, and/or reactive derivatives thereof to produce a mixture of acetic acid and a carboxylic acid having at least three carbon atoms, and/or an ester of either or both carboxylic acids, which process comprises contacting at elevated temperature and pressure (i) carbon monoxide, (ii) methanol and/or a reactive derivative thereof, (iii) an olefinically unsaturated carbonylatable reactant having at least two carbon atoms and/or a reactive derivative thereof and (iv) water in a liquid reaction composition in a carbonylation reactor, the liquid reaction composition comprising (a) a finite concentration of water, (b) a hydrocarbyl halide, (c) a rhodium catalyst and (d) a promoter selected from the group consisting of phosphine oxides, iodide
  • Reactant (ii) is methanol and/or a reactive derivative thereof.
  • Reactive derivatives of methanol include methyl acetate, dimethyl ether and methyl iodide.
  • reactant (ii) is methanol and/or methyl acetate.
  • Reactant (iii) is an olefinically unsaturated carbonylatable reactant having at least two carbon atoms and/or a reactive derivative thereof.
  • Reactive derivatives thereof include halides and esters, for example ethyl iodide and ethyl acetate.
  • Suitable olefinically unsaturated carbonylatable reactants having at least two carbon atoms include monofunctional olefins and dienes.
  • the monofunctional olefin is a C2 to Cg monofunctional olefin, more preferably a C2 to C4 monofunctional olefin such as ethylene and propylene, most preferably ethylene.
  • the diene is a C4 to Cg diene, more preferably butadiene.
  • a mixture of olefinically unsaturated carbonylatable reactants may be used in the process of the present invention.
  • Water is consumed as a reactant in addition to carbon monoxide in the carbonylation of the olefinically unsaturated reactant.
  • methanol and/or methyl acetate and water is fed to the reactor as well as ethylene, carbon monoxide and water to co-produce acetic acid and propionic acid.
  • the methanol and/or reactive derivative thereof and the olefinically unsaturated carbonylatable reactant having at least two carbon atoms and/or a reactive derivative thereof will be converted to and hence present as ester in the liquid reaction composition by reaction with carboxylic acid product and/or carboxylic acid solvent.
  • the methanol, olefinically unsaturated carbonylatable reactant, reactive derivatives thereof and esters thereof may comprise from 0.1 to 50 % by weight, preferably up to about 35 % by weight of the liquid reaction composition.
  • the concentration of methanol, methyl acetate, methyl propionate, ethyl acetate and ethyl propionate may be from 0.1 to 35 % by weight of the liquid reaction composition.
  • Component (a) in the liquid reaction composition is a finite concentration of water.
  • the concentration of water in the liquid reaction composition is in the range from 0.1 to 15%, preferably from 1 to 15%, more preferably from 1 to 10% by weight based on the weight of the liquid reaction composition.
  • the water may be formed in situ by, for example the esterification reaction between reactant components (ii) and/or (iii) and carboxylic acid product.
  • water may be introduced to the carbonylation reactor together with or separately from other components of the liquid reaction composition. Water may be separated from other components of the reaction composition withdrawn from the reactor and may be recycled in controlled amounts to maintain the concentration of water in the liquid reaction composition-;
  • Component (b) of the liquid reaction composition is a hydrocarbyl halide.
  • the hydrocarbyl moiety of the hydrocarbyl halide is an alkyl group, suitably a C ⁇ to C 4 alkyl group, preferably a methyl group.
  • the halide moiety of the hydrocarbyl halide is iodide or bromide, preferably iodide.
  • a preferred hydrocarbyl halide is methyl iodide.
  • the concentration of hydrocarbyl halide in the liquid reaction composition is in the range from 1 to 30%, preferably from 1 to 20%, more preferably from 5 to 20% by weight based on the weight of the liquid reaction composition.
  • Component (c) of the liquid reaction composition is a rhodium catalyst.
  • the rhodium catalyst in the liquid reaction composition may comprise any rhodium containing compound which is soluble in the liquid reaction composition.
  • the rhodium catalyst may be added to the liquid reaction composition in any suitable form which dissolves in the liquid reaction composition or is convertible to a soluble form.
  • RhCl(CO)(PPh 3 ) 2 RhCl(CO)(PPh 3 ) 2 .
  • the rhodium catalyst concentration in the liquid reaction composition is in the range 50 to 5000 ppm by weight of rhodium, preferably 100 to 1500 ppm.
  • Component (d) of the liquid reaction composition a promoter selected from the group consisting of phosphine oxides, iodide salts and mixtures thereof.
  • the monodentate phosphine oxide compound may be represented by the formula : R 1 X
  • R , R , R are independently an unsubstituted or substituted Ci to Cio alkyl group or an unsubstituted or substituted C 6 to C 15 aryl group.
  • the Ci to C 10 alkyl group may be straight or branched.
  • suitable Ci- C 10 alkyl groups include methyl, ethyl, n-butyl and n-octyl.
  • the .Cio alkyl group may be substituted by one or more substituents e.g. 1-4 substituents. Suitable substituents include to Cio alkyl groups and C 5 to C 15 aryl groups.
  • the C 6 -C 15 aryl group may be e.g. phenyl, alpha-naphthyl and beta-naphthyl, preferably phenyl.
  • the C 6 -C 15 group may be substituted with substituents selected from the group consisting of -NO 3 , -OH, -CN, -SO 3 H, -OCH 3 and -CO 2 H.
  • a preferred monodentate phosphine oxide compound of formula I is triphenylphosphine oxide.
  • the concentration of phosphine oxide in the liquid reaction composition is preferably greater than about 60 : 1 with respect to the rhodium concentration on a weight basis and more preferably from greater than about 60 : 1 to about 500 : 1.
  • the concentration of the phosphine oxide in the liquid reaction composition is from about 0,2 to about 3 gmol/1, more preferably from about 0.4 to about 1.5 gmol/1.
  • any metal iodide salt may be used in the process of the invention.
  • iodide salts of inorganic or organic cations may be used.
  • Suitable iodide salts of organic cations include for example, quaternary salts of organic cations.
  • Suitable salts of inorganic cations include iodide salts of a member of Group la or Group 2a of the Periodic Table as set forth in the "Handbook of Chemistry and Physics" published by CRC Press, Cleveland Ohio 1975-9176 (56 th Edition).
  • iodide salts of alkali metal iodides such as lithium iodide are preferred.
  • the iodide salt promoter may be present in the liquid composition at any effective amount up to the limit of its solubility in the reaction composition and/or any reaction system recycle process streams.
  • a mixture of phosphine oxides and/or a mixture of iodide salts may be used in the process of the present invention.
  • the carbon monoxide reactant may be essentially pure or may contain inert impurities, such as carbon dioxide, methane, nitrogen, noble gases, water and Ci to C 4 paraffinic hydrocarbons.
  • the partial pressure of carbon monoxide is in the range from 1 to 70 bar, preferably from 1 to 35 bar, more preferably from 1 to 15 bar.
  • the molar ratio of carbon monoxide : ethylene introduced to the carbonylation reactor is suitably in the range from greater than 1 : 1 to 100 : 1, preferably from 2 : 1 to 20 : 1.
  • a carboxylic acid preferably a carboxylic acid product of the co- carbonylation process, may be employed as solvent.
  • the co-carbonylation process of the present invention is operated at elevated temperature and pressure.
  • the elevated pressure is in the range from 10 to 200 barg, preferably 10 to 100 barg, more preferably from 15 to 50 barg.
  • the elevated temperature is in the range from 100 to 300°C, preferably, from 150 to 220°C.
  • the co-carbonylation process of the present invention may be operated as a batch or continuous process, preferably as a continuous process. Suitable forms of carbonylation reactor will be well-known to those skilled in the art.
  • the carboxylic acid products may be removed from the reactor by withdrawing liquid reaction composition and separating the carboxylic acid products by one or more flash and/or fractional distillation stages from the other components of the liquid reaction composition such as rhodium catalyst, promoter, halide, water and unconsumed reactants which may be recycled to the reactor to maintain their concentrations in the liquid reaction composition.
  • the carboxylic acid products may also be removed as a vapour from the reactor.
  • the present invention provides a process for the co- production of acetic acid and propionic acid which process comprises contacting continuously at a temperature in the range from 150 to 220°C and a pressure in the range from 10 to 100 barg, carbon monoxide at a partial pressure in the range from 1 to 35 bar, ethylene, methanol and/or methyl acetate and water in a liquid reaction composition in a carbonylation reactor, the liquid reaction composition comprising, (A) water at a concentration in the range from 1 to 15% by weight based on the weight of the liquid reaction composition, (B) methyl iodide at a concentration in the range from 1 to 20%) by weight based on the weight of the liquid reaction composition, (C) rhodium as catalyst and (D) a promoter selected from the group consisting of phosphine oxides, iodide salts and mixtures thereof.
  • the liquid reaction composition may further comprise acetic acid and propionic acid as solvent and carbonylation products together with methyl acetate and methyl propionate and lesser amounts of ethyl acetate and minor amounts of ethyl iodide and ethyl propionate.
  • the experiments were performed using a 300 ml zirconium autoclave equipped with a stirrer with gas dispersion impeller system, catalyst solution injection facility and cooling coils.
  • a gas supply to the autoclave was provided from a ballast vessel, feed gas being provided to maintain the autoclave at a constant pressure.
  • Carbon monoxide and ethylene were added in known amounts and allowed to mix before being fed to the autoclave.
  • the rate of gas uptake at a certain point in a reaction run was used to calculate the total carbonylation rate, as number of moles of reactant consumed per litre of cold degassed reactor composition per hour ⁇ mol dm " h " ⁇ , at a particular reactor composition (reactor composition based on a cold degassed volume).
  • methyl acetate concentration was calculated during the course of the reaction from the starting composition, assuming that three moles of methyl acetate are consumed for every four moles of carbon monoxide that are consumed from the ballast vessel (for a 4:1 mixture of carbon monoxide : ethylene). No allowance was made for organic components in the autoclave headspace.
  • the catalyst dissolved in a portion of the acetic acid liquid reactor charge, was charged to the liquid injection facility.
  • the reactor was then pressure tested with nitrogen, vented via a gas sampling system, and flushed with carbon monoxide/ethylene gas mixture several times (3 x 3-10 barG). If a promoter or additive was used this was placed in the autoclave and covered with a portion of the acetic acid charge (ca. lOg) prior to the pressure test.
  • the remaining liquid components of the reaction composition were charged to the autoclave via a liquid addition port.
  • the autoclave was then pressurised with the carbon monoxide/ethylene mixture (typically 8 barG) and heated with stirring (1500 rpm) to reaction temperature, 190°C.
  • the total pressure was then raised to approximately 3 barG below the desired operating pressure by feeding forward carbon monoxide/ethylene gas mixture from the ballast vessel. Once stable at temperature (about 15 minutes) the catalyst was injected using an over pressure of carbon monoxide. The catalyst injection facility has an efficiency of > 90%.
  • the reactor pressure was maintained at a constant value ( ⁇ 0.5 barG) by feeding gas from the ballast vessel throughout the experiment. Gas uptake from the ballast vessel was measured using data logging facilities throughout the course of the experiment.
  • reaction temperature was maintained within ⁇ 1°C of the desired reaction temperature by means of a heating mantle connected to a Eurotherm (Trade Mark) control system.
  • Eurotherm Trade Mark
  • excess heat of reaction was removed by means of cooling coils.
  • the acetic acid was obtained from carbonylation of a mixed methanol/methyl acetate feedstock.
  • Triphenylphosphine oxide, lithium iodide, methyl acetate, water, and methyl iodide were supplied by Aldrich.
  • Rh acetate was supplied by Johnson Matthey.
  • Carbon monoxide (> 99.9%) was supplied by Linde.
  • Ethylene (technical grade) was supplied by Air Products.
  • Ph 3 PO triphenylphosphine oxide
  • Rh acetate - rhodium acetate Ph 3 PO - triphenylphosphine oxide
  • Comparison Test A The above described experimental procedure was employed using the charge composition shown in Table 1. The rate data obtained and the final liquid composition are given in Tables 2 and 3 respectively.
  • Examples 3 and 4 show an increase in the amount of propionic acid with increased ethylene : carbon monoxide ratio, additonal water having been added with the additional ethylene.
  • Table 1 Charge compositions for carbonylation reactions:
  • Example 1 15.3 ⁇ 0.2 ⁇ 10 765 63.2 7.0
  • Example 2 12.4 ⁇ 0.2 60 940 62.9 6.4
  • Example 3 12.1 0.2 1070 14000 57.6 15.9

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Selon l'invention, un processus de co-carbonylation de méthanol et d'un réactif insaturé par oléfines pouvant être carbonylé, qui possède au moins deux atomes de carbone, et/ou de ses dérivés réactifs, permet de produire un mélange d'acide acétique et d'un acide carboxylique possédant au moins trois atomes de carbone et/ou un ester d'un ou de deux acides carboxyliques. Le procédé consiste à mettre en contact, à des températures et à une pression élevées (i) du monoxyde de carbone, (ii) du méthanol et/ou son dérivé réactif, (iii) un réactif insaturé par oléfines pouvant être carbonylé, qui possède au moins deux atomes de carbone, et/ou son dérivé réactif ainsi que (iv) de l'eau dans une composition de réaction liquide à l'intérieur d'un réacteur de carbonylation. La composition de réaction liquide comprend (a) une concentration finie d'eau, (b) un halogénure d'hydrocarbyle, (c) un catalyseur à rhodium et (d) un promoteur sélectionné dans le groupe constitué d'oxydes de phosphine, de sels de iodure et de leurs mélanges.
PCT/GB2000/004944 2000-01-14 2000-12-21 Coproduction d'acides carboxyliques et/ou de leurs esters WO2001051447A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001220161A AU2001220161A1 (en) 2000-01-14 2000-12-21 Co-production of carboxylic acids and/or their esters

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
GB0000934.0 2000-01-14
GB0000933.2 2000-01-14
GB0000936.5 2000-01-14
GB0000935.7 2000-01-14
GB0000935A GB0000935D0 (en) 2000-01-14 2000-01-14 Process
GB0000936A GB0000936D0 (en) 2000-01-14 2000-01-14 Process
GB0000933A GB0000933D0 (en) 2000-01-14 2000-01-14 Process
GB0000934A GB0000934D0 (en) 2000-01-14 2000-01-14 Process

Publications (2)

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WO2001051447A2 true WO2001051447A2 (fr) 2001-07-19
WO2001051447A3 WO2001051447A3 (fr) 2002-03-14

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Family Applications (4)

Application Number Title Priority Date Filing Date
PCT/GB2000/004933 WO2001051445A2 (fr) 2000-01-14 2000-12-21 Coproduction d'acides carboxyliques et/ou de leurs esters
PCT/GB2000/004944 WO2001051447A2 (fr) 2000-01-14 2000-12-21 Coproduction d'acides carboxyliques et/ou de leurs esters
PCT/GB2000/004924 WO2001051444A2 (fr) 2000-01-14 2000-12-21 Coproduction d'acides carboxyliques et/ou de leurs esters
PCT/GB2000/004943 WO2001051446A2 (fr) 2000-01-14 2000-12-21 Coproduction d'acides carboxyliques et/ou de leurs esters

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Application Number Title Priority Date Filing Date
PCT/GB2000/004933 WO2001051445A2 (fr) 2000-01-14 2000-12-21 Coproduction d'acides carboxyliques et/ou de leurs esters

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Application Number Title Priority Date Filing Date
PCT/GB2000/004924 WO2001051444A2 (fr) 2000-01-14 2000-12-21 Coproduction d'acides carboxyliques et/ou de leurs esters
PCT/GB2000/004943 WO2001051446A2 (fr) 2000-01-14 2000-12-21 Coproduction d'acides carboxyliques et/ou de leurs esters

Country Status (2)

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AU (4) AU2001220161A1 (fr)
WO (4) WO2001051445A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022031436A1 (fr) * 2020-08-04 2022-02-10 Eastman Chemical Company Traitement d'acide propionique

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7053241B1 (en) * 2005-02-24 2006-05-30 Celanese International Corporation Acetic acid production methods incorporating at least one metal salt as a catalyst stabilizer
CN108003022B (zh) * 2016-11-02 2020-01-07 中国科学院大连化学物理研究所 一种制备酯类化合物的方法
CN108003023B (zh) * 2016-11-02 2019-10-18 中国科学院大连化学物理研究所 一种制备丙酸甲酯的方法
CN108003024B (zh) * 2016-11-02 2019-10-18 中国科学院大连化学物理研究所 一种丙酸甲酯的制备方法

Citations (4)

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Publication number Priority date Publication date Assignee Title
EP0096974A1 (fr) * 1982-05-22 1983-12-28 BP Chemicals Limited Procédé de préparation d'un ou de plusieurs anhydrides d'acides carboxyliques
US4658053A (en) * 1984-03-08 1987-04-14 Bp Chemicals Limited Production of esters
US5001259A (en) * 1984-05-03 1991-03-19 Hoechst Celanese Corporation Methanol carbonylation process
US5817869A (en) * 1995-10-03 1998-10-06 Quantum Chemical Corporation Use of pentavalent Group VA oxides in acetic acid processing

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US4132734A (en) * 1976-05-03 1979-01-02 Monsanto Company Synthesis of carboxylic acids
US4111982A (en) * 1976-07-26 1978-09-05 Monsanto Company Coproduction of acetic and propionic acids
US4681707A (en) * 1982-09-30 1987-07-21 The British Petroleum Company P.L.C. Process for the production of carboxylic acid esters and/or carboxylic acids
FR2703351A1 (fr) * 1993-03-31 1994-10-07 Rhone Poulenc Chimie Procédé de préparation d'acides carboxyliques ou des esters correspondants en présence d'un catalyseur à base de rhodium et d'iridium.
GB9503382D0 (en) * 1995-02-21 1995-04-12 Bp Chem Int Ltd Process
GB9503383D0 (en) * 1995-02-21 1995-04-12 Bp Chem Int Ltd Process
GB9504708D0 (en) * 1995-03-08 1995-04-26 Bp Chem Int Ltd Process
GB9715402D0 (en) * 1997-07-22 1997-09-24 Bp Chem Int Ltd Process
EP1085004A1 (fr) * 1999-09-20 2001-03-21 Dsm N.V. Procédé de carbonylation de butadiène et/ou de dérivés de butadiène

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0096974A1 (fr) * 1982-05-22 1983-12-28 BP Chemicals Limited Procédé de préparation d'un ou de plusieurs anhydrides d'acides carboxyliques
US4658053A (en) * 1984-03-08 1987-04-14 Bp Chemicals Limited Production of esters
US5001259A (en) * 1984-05-03 1991-03-19 Hoechst Celanese Corporation Methanol carbonylation process
US5817869A (en) * 1995-10-03 1998-10-06 Quantum Chemical Corporation Use of pentavalent Group VA oxides in acetic acid processing

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022031436A1 (fr) * 2020-08-04 2022-02-10 Eastman Chemical Company Traitement d'acide propionique

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WO2001051444A3 (fr) 2002-02-28
AU2001220161A1 (en) 2001-07-24
WO2001051445A2 (fr) 2001-07-19
AU2001223818A1 (en) 2001-07-24
WO2001051444A2 (fr) 2001-07-19
WO2001051446A2 (fr) 2001-07-19
AU2001222071A1 (en) 2001-07-24
WO2001051445A3 (fr) 2002-05-10
WO2001051446A3 (fr) 2002-03-14
WO2001051447A3 (fr) 2002-03-14
AU2001222065A1 (en) 2001-07-24

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