WO2001051445A2 - 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
WO2001051445A2
WO2001051445A2 PCT/GB2000/004933 GB0004933W WO0151445A2 WO 2001051445 A2 WO2001051445 A2 WO 2001051445A2 GB 0004933 W GB0004933 W GB 0004933W WO 0151445 A2 WO0151445 A2 WO 0151445A2
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WO
WIPO (PCT)
Prior art keywords
liquid reaction
reaction composition
range
iridium
rhodium
Prior art date
Application number
PCT/GB2000/004933
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English (en)
Other versions
WO2001051445A3 (fr
Inventor
Stephen David Cook
Lesley Ann Key
John Glenn Sunley
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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 GB0000934A external-priority patent/GB0000934D0/en
Priority claimed from GB0000933A external-priority patent/GB0000933D0/en
Priority claimed from GB0000936A external-priority patent/GB0000936D0/en
Priority claimed from GB0000935A external-priority patent/GB0000935D0/en
Application filed by Bp Chemicals Limited filed Critical Bp Chemicals Limited
Priority to AU2001222065A priority Critical patent/AU2001222065A1/en
Publication of WO2001051445A2 publication Critical patent/WO2001051445A2/fr
Publication of WO2001051445A3 publication Critical patent/WO2001051445A3/fr

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    • 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 are known and are described, for example, Howard et al Catalysis Today, 18(1993) 325-354.
  • EP-A-0728727 discloses a process for the carbonylation of a C ⁇ to C 4 alkyl alcohol and/or a reactive derivative thereof which process comprises contacting a d to C alkyl alcohol and/or a reactive derivative thereof which carbon monoxide in a liquid reaction composition in a carbonylation reactor characterised in that the liquid reaction composition comprises: (a) a rhodium catalyst, (b) an alkyl halide, and (c) as promoter, at least one of ruthenium and osmium.
  • the carbonylation product is the corresponding carboxylic acid or alkyl ester thereof under aqueous conditions and the corresponding carboxylic acid anhydride under substantially anhydrous conditions.
  • EP-A-0728727 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 4132734 discloses a process for converting an ethylenically unsaturated compound having 2 to 30 carbon atoms by reaction with carbon monoxide and water in contact with a catalyst system consisting essentially of a rhodium or iridium oxide, salt or carbonyl consisting only of the metal and carbonyl moieties and a halogen component selected from the group consisting of bromine, iodine, alkyl bromide, alkyl iodide, hydrogen iodide and hydrogen bromide in which process there is included as ' accelerator a metal compound selected from the group consisting of the salt, oxides and hydroxides of cobalt, iron and manganese, the concentration of said metal compound being in the range from about 0.005 to about 0.1 molar and in which the water concentration is maintained at less than 6 molar.
  • a catalyst system consisting essentially of a rhodium or iridium oxide, salt or carbonyl consisting only of the metal and carbony
  • 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 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.
  • US 4111982 is silent on the use of iridium as a carbonylation catalyst.
  • GB-A-2298648 discloses a process for the carbonylation of a carbonylatable reactant having a carbonylatable moiety having at least two carbon atoms and/or a reactive derivative thereof which process comprises contacting said carbonylatable reactant and/or a reactive derivative thereof with carbon monoxide in a liquid reaction composition in a carbonylation reactor characterised in that the liquid reaction composition comprises: (a) an iridium catalyst, (b) a halide, (c) at least a finite concentration of water, (d) a carbonylatable reactant having a carbonylatable moiety having at least two carbon atoms and/or a reactive derivative thereof and (c) as promoter, at least one of ruthenium and osmium.
  • the aforesaid carbonylatable reactant may be co-fed to the reactor with methanol and/or a reactive derivative thereof such as methyl acetate, in which case acetic acid and/or methyl acetate will be a co-product of the carbonylation reaction.
  • a particularly preferred embodiment is said to be co-feeding methanol (and/or methyl acetate and water) with (ethylene and water) to co-produce acetic acid and propionic acid.
  • GB-A-2327420 describes a process for the production of at least one carboxylic acid which process comprises contacting at elevated temperature carbon monoxide in a carbonylation reactor with a liquid reaction composition comprising (a) (i) at least one olefinically unsaturated compound and, optionally (ii) at least one alcohol and/or a reactive derivative thereof, (b) an iridium catalyst, (c) a halide co-catalyst, (d) at least a finite concentration of water, and (e) as promoter, at least one of (i) cadmium, (ii) mercury, (in) zinc, (iv) gallium, (v) indium, (vi) tungsten, and (vii) rhenium provided that in the absence of an alcohol and/or a reactive derivative thereof (A) in the presence of promoters (i) to (vi) water is present in an amount less than 3% by weight based on the weight of the liquid reaction composition, and (B) in the presence of promoter
  • European patent publication EP-A-0618183 relates to a process for the preparation of carboxylic acids having n +1 carbon atoms or the corresponding esters, by reacting a carbonylatable reactant having n carbon atoms with carbon monoxide in the presence of a homogeneous catalyst based on rhodium and iridium.
  • the carbonylatable reactant is said to be at least one of R(OH) m , RX, ROR' and ROCOR'.
  • EP-A-0618183 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.
  • GB-2298200-A 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.
  • the problem to be solved by the present invention is the provision of an improved co-carbonylation process.
  • a solution to the problem is the use of both rhodium and iridium carbonylation catalysts.
  • 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 and (c) rhodium and iridium as catalyst.
  • 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 olef ⁇ n is a C2 to C ⁇ monofunctional olefin, more preferably a C2 to C4 monofunctional olefin such as ethylene and propylene, most preferably ethylene.
  • the diene is a C4 to C ⁇ 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 Ci to C 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 mixture of rhodium and iridium 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.
  • suitable rhodium-containing compounds which may be added to the liquid reaction composition include [Rh(CO) Cl]2, [Rh(CO) 2 I]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.
  • the iridium carbonylation catalyst is suitably present in the liquid reaction composition at a concentration in the range 400 to 5000 ppm measured as iridium, preferably in the range 500 to 3000 ppm measured as iridium, more preferably in the range 700 to 3000 ppm measured as iridium.
  • the rate of the carbonylation reaction increases as the concentration of iridium is increased.
  • the iridium catalyst in the liquid reaction composition may comprise any iridium-containing compound which is soluble in the liquid reaction composition.
  • the iridium catalyst may be added to the liquid reaction composition for the carbonylation reaction in any suitable form which dissolves in the liquid reaction composition or is convertible to a soluble form.
  • suitable iridium-containing compounds which may be added to the liquid reaction composition include IrCl3, M3, IrBr3,
  • green iridium acetate which may be used in an acetic acid or aqueous acetic acid solution.
  • the mol ratio of rhodium : iridium is in the range from 0.1 : 1 to 20 : 1, preferably, 1 : 1 to 20 : 1.
  • co-promoter selected from the group consisting of osmium, ruthenium and mixtures thereof.
  • the ruthenium and/or osmium co-promoter may comprise any ruthenium and/or osmium containing compound which is soluble in the liquid reaction composition.
  • the co- promoter may be added to the liquid reaction composition in any suitable form which dissolves in the liquid reaction composition or is convertible to soluble form. Examples of suitable ruthenium-containing compounds and suitable osmium-containing compounds are described in GB-22980200-A.
  • the molar ratio of each co-promoter to the combined iridium and rhodium components is suitably in the range 0.1 : 1 to 15 : 1, preferably 0.5 : 1 to 10 : 1.
  • 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 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 and iridium catalysts, 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 and (C) rhodium and iridium as catalyst.
  • 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 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 "3 h "1 ⁇ , at a particular reactor composition (reactor composition based on a cold degassed volume).
  • the 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.
  • 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.
  • the 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.
  • excess heat of reaction was removed by means of cooling coils. Each run was conducted until the gas uptake had ceased (i.e. until the gas uptake from the ballast vessel achieved a rate of less than 0.1 bar min "1 )
  • the ballast vessel was then isolated and the reactor crash cooled by use of the cooling coils.
  • the acetic acid was obtained from carbonylation of a mixed methanol/methyl acetate feedstock.
  • [Rh(CO) 2 Cl] 2 Methyl acetate, water, and methyl iodide were supplied by Aldrich.
  • H 2 IrCl 6 is supplied as an aqueous solution by Johnson Matthey.
  • Carbon monoxide (> 99.9%) was supplied by Linde.
  • Ethylene (technical grade) was supplied by Air Products. Comparison Tests A and B. The above described experimental procedure was employed using the charge compositions shown in Table 1.
  • the rate data obtained and the final liquid composition are given in Tables 2 and 3 respectively.
  • Example 4 shows that a higher amount of propionic acid is formed when the amount ratio of ethylene relative to carbon monoxide is increased.
  • Example 1 CO C 2 H 4 510 875 11.5 7.0 23 16.0 4:1
  • Example 3 CO C 2 K 500 90 11.4 7.0 23 9.5 4:1
  • Example 4 CO C 2 H 4 480 820 10.9 6.9 23 23.1 2:1

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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

L'invention concerne un procédé de co-carbonylation de méthanol et d'un réactif insaturé en oléfine, se prêtant à la carbonylation et comprenant au moins deux atomes de carbone, et/ou de dérivés réactifs de ceux-ci, afin de produire un mélange d'acide acétique et d'un acide carboxylique comprenant au moins trois atomes de carbone, et/ou un ester d'un ou des deux acides carboxyliques. Ce procédé consiste à faire entrer en contact à une pression et à une température élevées (i) du monoxyde de carbone, (ii) du méthanol et/ou un dérivé réactif de celui-ci, (iii) un réactif insaturé en oléfine se prêtant à la carbonylation et comprenant au moins deux atomes de carbone et/ou un dérivé réactif de celui-ci, et (iv) de l'eau, dans une composition réactionnelle liquide à l'intérieur d'un réacteur de carbonylation. La composition réactionnelle liquide comprend (a) une concentration finie en eau, (b) un halogénure d'hydrocarbyle, (c) un catalyseur à base de rhodium et (d) du ruthénium et/ou de l'osmium en tant que promoteurs.
PCT/GB2000/004933 2000-01-14 2000-12-21 Coproduction d'acides carboxyliques et/ou de leurs esters WO2001051445A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001222065A AU2001222065A1 (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
GB0000934A GB0000934D0 (en) 2000-01-14 2000-01-14 Process
GB0000933.2 2000-01-14
GB0000936.5 2000-01-14
GB0000933A GB0000933D0 (en) 2000-01-14 2000-01-14 Process
GB0000936A GB0000936D0 (en) 2000-01-14 2000-01-14 Process
GB0000935.7 2000-01-14
GB0000935A GB0000935D0 (en) 2000-01-14 2000-01-14 Process
GB0000934.0 2000-01-14

Related Child Applications (1)

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US10/178,667 Continuation US6770643B2 (en) 1999-12-24 2002-06-24 Azaindoles

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WO2001051445A2 true WO2001051445A2 (fr) 2001-07-19
WO2001051445A3 WO2001051445A3 (fr) 2002-05-10

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

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PCT/GB2000/004943 WO2001051446A2 (fr) 2000-01-14 2000-12-21 Coproduction d'acides carboxyliques et/ou de leurs esters

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Families Citing this family (5)

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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
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
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
US20240002324A1 (en) * 2020-08-04 2024-01-04 Eastman Chemical Company Propionic acid process

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GB2298200A (en) * 1995-02-21 1996-08-28 Bp Chem Int Ltd Catalyst system comprising iridium and rhodium catalyst, alkyl halide and at least one ruthenium, osmium or rhenium promoter for use in alcohol carbonylation
GB2327420A (en) * 1997-07-22 1999-01-27 Bp Chem Int Ltd Production of oxygenated compounds
EP1085004A1 (fr) * 1999-09-20 2001-03-21 Dsm N.V. Procédé de carbonylation de butadiène et/ou de dérivés de butadiène

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ZA833528B (en) * 1982-05-22 1984-12-24 Bp Chem Int Ltd Process for the production of one or more carboxylic acid anhydrides
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GB9503382D0 (en) * 1995-02-21 1995-04-12 Bp Chem Int Ltd Process
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EP0618183A1 (fr) * 1993-03-31 1994-10-05 Pardies Acetiques Procédé de préparation d'acides carboxyliques ou des esters correspondants en présence d'un catalyseur à base de rhodium et d'iridium
GB2298200A (en) * 1995-02-21 1996-08-28 Bp Chem Int Ltd Catalyst system comprising iridium and rhodium catalyst, alkyl halide and at least one ruthenium, osmium or rhenium promoter for use in alcohol carbonylation
GB2327420A (en) * 1997-07-22 1999-01-27 Bp Chem Int Ltd Production of oxygenated compounds
EP1085004A1 (fr) * 1999-09-20 2001-03-21 Dsm N.V. Procédé de carbonylation de butadiène et/ou de dérivés de butadiène

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AU2001222071A1 (en) 2001-07-24
WO2001051446A3 (fr) 2002-03-14
WO2001051444A3 (fr) 2002-02-28
WO2001051447A2 (fr) 2001-07-19
AU2001223818A1 (en) 2001-07-24
WO2001051447A3 (fr) 2002-03-14
WO2001051446A2 (fr) 2001-07-19
WO2001051444A2 (fr) 2001-07-19
AU2001220161A1 (en) 2001-07-24
WO2001051445A3 (fr) 2002-05-10
AU2001222065A1 (en) 2001-07-24

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