CN113019460B - Iridium complex catalyst and preparation method thereof - Google Patents

Iridium complex catalyst and preparation method thereof Download PDF

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CN113019460B
CN113019460B CN202011491271.3A CN202011491271A CN113019460B CN 113019460 B CN113019460 B CN 113019460B CN 202011491271 A CN202011491271 A CN 202011491271A CN 113019460 B CN113019460 B CN 113019460B
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iridium
catalyst
vinylpyridine
ligand
copolymer
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CN113019460A (en
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张志炳
胡宗贵
张德谨
朱桂生
周政
胡兴邦
赵禄强
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JIANGSU SOPO CHEMICAL CO LTD
Nanjing Anlige Co ltd
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JIANGSU SOPO CHEMICAL CO LTD
Nanjing Institute of Microinterface Technology Co Ltd
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    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/1691—Coordination polymers, e.g. metal-organic frameworks [MOF]
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/827—Iridium

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Abstract

The invention provides an iridium complex catalyst and a preparation method thereof, wherein the iridium complex catalyst is obtained by taking a copolymer formed by 2-vinylpyridine and vinyl diphenylphosphine as a ligand and carrying out coordination reaction with an iridium compound. The catalyst takes a copolymer formed by 2-vinylpyridine and vinyl diphenylphosphine as a ligand, and the iridium-based catalyst for preparing the methanol carbonylation reaction has better applicability to the current mainstream production process and production device.

Description

Iridium complex catalyst and preparation method thereof
Technical Field
The invention relates to the field of catalyst preparation, and particularly relates to an iridium complex catalyst and a preparation method thereof.
Background
Acetic acid is a very important chemical product, and products derived from the acetic acid are hundreds of types, and are widely applied to medicines, pesticides, foods and other related industries. Currently, methanol carbonylation is the most widely used technical route for producing acetic acid in industry. The catalyst for preparing acetic acid by methanol carbonylation in industry has three stages of cobalt-based catalyst developed by BASF company, rhodium-based catalyst developed by Monsanto company and iridium-based catalyst developed by BP company, wherein the iridium-based catalyst has the characteristics of relatively low price, low water content, high catalytic activity and the like, and has become the mainstream catalyst for producing acetic acid by methanol carbonylation. However, the iridium-based catalyst still has the problems that the reaction system seriously corrodes equipment, and metallic iridium is easy to precipitate and deactivate.
In view of the above, the present invention is particularly proposed.
Disclosure of Invention
The first purpose of the invention is to provide an iridium complex catalyst, which is formed by using a copolymer formed by two types of 2-vinylpyridine with relatively strong electron donating capability and vinyl diphenylphosphine as a ligand, and has high activity and excellent catalytic performance.
The second purpose of the invention is to provide a preparation method of the iridium complex catalyst, the preparation method is simple in operation steps, and the prepared catalyst is excellent in catalytic effect.
In order to achieve the above purpose of the present invention, the following technical solutions are adopted:
the invention provides an iridium complex catalyst which is obtained by taking a copolymer formed by 2-vinylpyridine and vinyl diphenylphosphine as a ligand and carrying out coordination reaction with an iridium compound, wherein the addition amount of iridium is 5-12wt% of the mass of the copolymer.
The amount of iridium added is calculated based on the specific iridium element.
Related researches show that the methanol carbonylation catalyst using the copolymer as the ligand has the advantages of high activity, low equipment corrosion and high stability, and the higher the density of electron cloud on the metal of the catalyst, the higher the catalytic activity of the catalyst. In order to obtain a catalyst with higher activity, the invention designs and synthesizes a copolymer formed by two types of 2-vinylpyridine with stronger electron donating capability and vinyl diphenylphosphine as a ligand, and the coordination reaction is carried out on active metal iridium, N on the 2-vinylpyridine with stronger electron donating capability and P on the vinyl diphenylphosphine, so that the electron cloud density on the active metal iridium is increased, and the catalytic activity of the iridium-based catalyst is improved.
The reason why the ratio of iridium to copolymer needs to be controlled is that iridium is used as an active center of the whole catalytic system, and the addition amount is too small, which affects the catalytic activity, while the addition amount is too large, which may cause part of iridium not to be coordinated with the copolymer ligand, and the uncoordinated metallic iridium not only has low catalytic activity, but also is difficult to recover, and even may affect the selectivity of the reaction.
Preferably, in order to improve the catalytic activity of the catalyst, the molar ratio of the 2-vinylpyridine to the vinyldiphenylphosphine is (5-7): (3-5), the reason is that the monomer polymerization process is a polymerization reaction initiated by free radicals, so that two coordination units of N → Ir and P → Ir with different strengths exist in the catalyst structure, and N and P can be coordinated with Ir into a main coordination form simultaneously by regulating and controlling the polymerization conditions. Thus, on the one hand, the catalyst body can be in a stable state by utilizing the strong coordination effect between N and Ir, and on the other hand, the relatively weak P → Ir coordinate bond is easy to dissociate, so that the oxidative addition reaction of methyl iodide is facilitated, and the step is also a control step of the methanol carbonylation reaction process, so that the aim of controlling the polymerization reaction can be achieved only by controlling the ratio of the two monomers, which is also obtained after a large amount of practice.
Preferably, the catalyst also comprises a promoter ruthenium compound, wherein the molar ratio of the ruthenium element to the iridium element is (4-6): 1.
Preferably, the type of the promoter ruthenium compound is Ru (CO) 4 I 2 、RuCl 3 、[Ru(CO) 4 I 2 ] 2 Any one or a mixture of several of them;
preferably, the iridium compound is of the type IrCl 3 、[Ir(CO) 2 I] 2 、[Ir(CO) 2 Cl] 2 Or Ir (OAc) 3 Any one or a mixture of several of them.
The catalyst obtained by matching the iridium catalyst with the copolymer has better catalytic activity than the conventional iridium-based catalyst, and particularly can remarkably improve the conversion rate of raw materials and the yield of products in the production of acetic acid by methanol carbonylation reaction. In the prior art, the influence on the electron density of metal after coordination is relatively large in terms of a coordination mechanism, and the catalytic effect of the iridium metal is finally directly influenced, so that the inventors find that the catalytic effect of the catalyst can be remarkably improved by adopting the specific polymer of the invention after a plurality of practices.
The invention also provides a preparation method of the iridium complex catalyst, besides providing the formula of the catalyst, which comprises the following steps:
carrying out polymerization reaction on 2-vinylpyridine, vinyl diphenylphosphine, a solvent and an initiator to obtain a copolymer ligand;
and stirring and mixing the copolymer ligand, the ruthenium compound and the promoter.
Preferably, the polymerization temperature is 60-70 ℃ and the polymerization time is 8-12h.
Preferably, the addition amount of the initiator is 1-3wt% of the mass of the 2-vinylpyridine and the vinyl diphenylphosphine.
Preferably, the time for mixing with stirring is 30-60min.
Preferably, the solvent is one of benzene and toluene.
Preferably, the initiator is dibenzoyl peroxide.
By regulating and controlling each parameter in the preparation method within a proper range, the performance of the prepared catalyst can be obviously improved.
In a word, the catalyst obtained by the preparation method can be better applied to the process of producing acetic acid by methanol carbonylation catalytic reaction, and has better applicability to the existing mainstream production process and production devices.
In the reaction catalysis process, the addition of the iridium-based catalyst is 500-5000 ppm calculated by iridium, the mass fraction of water in the whole reaction system is 5%, the mass fraction of methyl iodide in the whole reaction system is 6%, the CO pressure is 1.5-2MPa, and the reaction temperature is 170-220 ℃.
Compared with the prior art, the invention has the beneficial effects that:
(1) The catalyst of the invention selects a copolymer formed by two 2-vinylpyridine with stronger electron donating capability and vinyl diphenylphosphine as a ligand, and an iridium complex catalytic system for preparing acetic acid by high-activity methanol carbonylation is formed by coordination of the novel ligand and metal iridium;
(2) The iridium catalyst preparation method provided by the invention is simple in operation steps, and the prepared catalyst is excellent in catalytic effect;
(3) The catalyst forms a metal complex with a stable structure after being coordinated with the metal iridium, and compared with a common methanol carbonylation reaction catalyst, a heterogeneous catalysis system formed by the catalyst has higher activity, so that the methanol carbonylation reaction can be carried out at relatively lower temperature and pressure. Meanwhile, the catalyst is heterogeneous, so that the catalyst is easier to recover.
Drawings
Various other advantages and benefits will become apparent to those of ordinary skill in the art upon reading the following detailed description of the preferred embodiments. The drawings are only for purposes of illustrating the preferred embodiments and are not to be construed as limiting the invention. Also, like reference numerals are used to refer to like parts throughout the drawings. In the drawings:
FIG. 1 is a gas chromatogram of the product provided in example 3 of the present invention.
Detailed Description
Embodiments of the present invention will be described in detail below with reference to examples, but it will be understood by those skilled in the art that the following examples are only illustrative of the present invention and should not be construed as limiting the scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
Example 1
The reaction process of catalyst preparation and methanol carbonylation to prepare acetic acid comprises the following steps:
(1) Accurately measuring 0.01mol of 2-vinylpyridine and 0.01mol of vinyl diphenylphosphine, adding 0.06g of dibenzoyl peroxide and 24mL of toluene solvent, and reacting at 65 ℃ for 12h to obtain a copolymer ligand. And then 0.5g of copolymer ligand is weighed and dissolved in methanol, iridium chloride accounting for 10wt% of the total mass of the 2-vinylpyridine and the vinyl diphenylphosphine is added into the solution, the solution is stirred for 30min at room temperature, and then the solution is precipitated by diethyl ether, washed and dried to obtain the iridium-based catalyst.
(2) Weighing 0.1g of iridium-based catalyst, placing the iridium-based catalyst into a high-pressure reaction kettle, adding 0.2g of ruthenium chloride hydrate into the reaction kettle, stirring for 5min to obtain an iridium complex catalyst, adding 10mL of methanol, 0.2mL of methyl iodide and 3mL of water, introducing CO to ensure that the pressure in a reaction system is 1.5MPa, and reacting for 12h at the temperature of 180 ℃, wherein the conversion rate of methanol is 97%.
Example 2
The reaction process of catalyst preparation and methanol carbonylation to prepare acetic acid comprises the following steps:
(1) Accurately measuring 0.015mol of 2-vinylpyridine and 0.01mol of vinyl diphenylphosphine, adding 0.07g of dibenzoyl peroxide and 28mL of toluene solvent, and reacting at 60 ℃ for 8h to obtain a copolymer ligand. And then weighing 0.5g of copolymer ligand, dissolving the copolymer ligand in methanol, adding iridium chloride accounting for 10wt% of the total mass of the 2-vinylpyridine and the vinyl diphenylphosphine, stirring at room temperature for 30min, precipitating with diethyl ether, washing, and drying to obtain the iridium-based catalyst.
(2) Weighing 0.1g of iridium-based catalyst, placing the iridium-based catalyst in a high-pressure reaction kettle, adding 0.2g of ruthenium chloride hydrate, stirring for 10min to obtain an iridium complex catalyst, adding 10mL of methanol, 0.2mL of methyl iodide and 3mL of water, introducing CO to ensure that the pressure in a reaction system is 1.5MPa, and reacting for 12h at the temperature of 180 ℃, wherein the conversion rate of methanol is 97%.
Example 3
The reaction process of catalyst preparation and methanol carbonylation to prepare acetic acid comprises the following steps:
(1) Accurately measuring 0.02mol of 2-vinylpyridine and 0.01mol of vinyl diphenylphosphine, adding 0.086g of dibenzoyl peroxide and 34mL of toluene solvent, and reacting at 70 ℃ for 10h to obtain a copolymer ligand. And then 0.5g of copolymer ligand is weighed and dissolved in methanol, iridium chloride accounting for 10wt% of the total mass of the 2-vinylpyridine and the vinyl diphenylphosphine is added into the solution, the solution is stirred for 30min at room temperature, and then the solution is precipitated by diethyl ether, washed and dried to obtain the iridium-based catalyst.
(2) Weighing 0.1g of iridium-based catalyst, placing the iridium-based catalyst in a high-pressure reaction kettle, adding 0.2g of ruthenium chloride hydrate into the reaction kettle, stirring the mixture for 30min to obtain an iridium complex catalyst, adding 10mL of methanol, 0.2mL of methyl iodide and 3mL of water, introducing CO to enable the pressure in a reaction system to be 1.5MPa, reacting the mixture for 12h at the temperature of 180 ℃, wherein the conversion rate of methanol is 98%, and specific results can be shown in a gas chromatogram of FIG. 1.
Example 4
0.1g of the intermediate catalyst obtained in example 3 was weighed and placed in an autoclave, 0.2g of ruthenium chloride hydrate was added thereto to obtain an iridium complex catalyst, 10mL of methanol, 0.2mL of methyl iodide and 3mL of water were added thereto, 2MPa of CO gas was introduced thereto, and the reaction was carried out at 180 ℃ for 24 hours with a methanol conversion of 99%.
Example 5
0.1g of the catalyst obtained in example 3 was weighed and placed in an autoclave, 0.2g of ruthenium chloride hydrate was added thereto to obtain an iridium complex catalyst, 10mL of methanol, 0.2mL of methyl iodide and 3mL of water were added thereto, and 2MPa of CO gas was introduced and reacted at 170 ℃ for 12 hours with a methanol conversion of 97%.
Example 6
0.1g of the catalyst obtained in example 3 was weighed and placed in an autoclave, 0.2g of ruthenium acetate was added thereto to obtain an iridium complex catalyst, 10mL of methanol, 0.2mL of methyl iodide and 3mL of water were added thereto, 2MPa of CO gas was introduced thereto, and the mixture was reacted at 180 ℃ for 24 hours with a methanol conversion of 99%.
Example 7
The other procedure was in accordance with example 3, except that the molar ratio of 2-vinylpyridine to vinyldiphenylphosphine was 5, and the conversion of methanol was determined to be 97%.
Example 8
The other operating procedures were in accordance with example 3, except that the molar ratio of 2-vinylpyridine to vinyldiphenylphosphine was 7.
Example 9
The other procedure was in accordance with example 3, except that the molar ratio of 2-vinylpyridine to vinyldiphenylphosphine was 8, and the conversion of methanol was determined to be 80%.
Example 10
The other operating steps were identical to those of example 3, except that the molar ratio of the ruthenium element in the hydrated ruthenium oxide to the iridium element in the iridium-based catalyst was 4.
Example 11
The other operating steps were identical to those of example 3, except that the molar ratio of ruthenium element in the hydrated ruthenium oxide to iridium element in the iridium-based catalyst was 6.
Example 12
The other operating steps were identical to those of example 3, except that the molar ratio of the ruthenium element in the hydrated ruthenium oxide to the iridium element in the iridium-based catalyst was 5.
Example 13
The further procedure was in accordance with example 3, the iridium chloride addition ratio being adjusted to 5% by weight, and the conversion of methanol being determined to be 97%.
Example 14
The other operating steps correspond to those of example 3, the iridium chloride addition ratio being adjusted to 12% by weight, and the methanol conversion being determined to be 98%.
Comparative example 1
The procedure is carried out as in example 4 of patent CN101693209A, with a methanol conversion of 94%.
Comparative example 2
The specific procedure is in accordance with example 3, except that vinyldiphenylphosphine is replaced by methyl acrylate and the final methanol conversion is determined to be 80%, probably because the conversion is reduced more because the pressure is too low, which has an effect on the catalytic activity of the catalyst.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and these modifications or substitutions do not depart from the spirit of the corresponding technical solutions of the embodiments of the present invention.

Claims (8)

1. An iridium complex catalyst is characterized by being obtained by taking a copolymer formed by 2-vinylpyridine and vinyl diphenylphosphine as a ligand and carrying out coordination reaction with an iridium compound, wherein the addition amount of iridium is 5-12wt% of the mass of the copolymer;
the molar ratio of the 2-vinylpyridine to the vinyldiphenylphosphine is (5-7): (3-5);
the catalyst also comprises a promoter ruthenium compound, wherein the molar ratio of ruthenium element to iridium element is (4-6): 1.
2. The iridium complex catalyst according to claim 1, wherein the type of the ruthenium compound as a promoter is Ru (CO) 4 I 2 、RuCl 3 、[Ru(CO) 4 I 2 ] 2 Any one or a mixture of several of them;
the iridium compound is IrCl 3 、[Ir(CO) 2 I] 2 、[Ir(CO) 2 Cl] 2 Or Ir (OAc) 3 Any one or a mixture of several of them.
3. The method for producing an iridium complex catalyst according to any one of claims 1 to 2, comprising the steps of:
carrying out polymerization reaction on 2-vinylpyridine, vinyl diphenylphosphine, a solvent and an initiator to obtain a copolymer ligand;
and stirring and mixing the copolymer ligand, the iridium compound and the accelerator.
4. The process according to claim 3, wherein the polymerization temperature is 60 to 70 ℃ and the polymerization time is 8 to 12 hours.
5. The process according to claim 3, wherein the initiator is added in an amount of 1 to 3wt% based on the total mass of the 2-vinylpyridine and the vinyldiphenylphosphine.
6. The method according to claim 3, wherein the time for mixing with stirring is 30 to 60min.
7. The method of claim 3, wherein the solvent is one of benzene and toluene.
8. The method of claim 3, wherein the initiator is dibenzoyl peroxide.
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US4358411A (en) * 1979-06-29 1982-11-09 The Halcon Sd Group, Inc. Preparation of carbonylation products
US4996178A (en) * 1987-02-05 1991-02-26 The Goodyear Tire & Rubber Co. Low temperature synthesis of condensation polymers
TW272949B (en) * 1994-07-22 1996-03-21 Taishal Kagaku Kogyo Kk
CN101693209A (en) * 2009-08-24 2010-04-14 江苏索普（集团）有限公司 Iridium picolinate complex catalyst for synthesizing acetic acid by methanol carbonylation
CN102489327B (en) * 2011-11-24 2013-09-11 重庆大学 Catalyst for acetic acid synthesis through methanol carbonylation and application method thereof

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Patentee after: Nanjing Anlige Co.,Ltd.

Country or region after: China

Patentee after: JIANGSU SOPO CHEMICAL Co.,Ltd.

Address before: No. 88, Tanqu South Road, Jiangbei New District, Nanjing City, Jiangsu Province

Patentee before: Nanjing Yanchang Reaction Technology Research Institute Co.,Ltd.

Country or region before: China

Patentee before: JIANGSU SOPO CHEMICAL Co.,Ltd.