CN100469747C - Production and separation of alkyl aromatic aldehyde - Google Patents
Production and separation of alkyl aromatic aldehyde Download PDFInfo
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- CN100469747C CN100469747C CNB2005101321566A CN200510132156A CN100469747C CN 100469747 C CN100469747 C CN 100469747C CN B2005101321566 A CNB2005101321566 A CN B2005101321566A CN 200510132156 A CN200510132156 A CN 200510132156A CN 100469747 C CN100469747 C CN 100469747C
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- organohalogen compounds
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Abstract
Separation of alkyl-aromatic aldehyde is carried out by adding organic halide into reactant mixture as de-complex agent and separating free alkyl-aromatic aldehyde from complex alkyl-aromatic aldehyde reactant mixture. The reactant mixture consists of alkyl-aromatic aldehyde and acid ion liquid, which contains metal halide and organic halide. It's easy and convenient.
Description
Technical field
The invention relates to the preparation and the separation method of alkyl aromatic aldehyde, more specifically about the separation method of the alkyl aromatic aldehyde mixture of reaction products of carbonyl process preparation, and the preparation method who uses the alkyl aromatic aldehyde of this separation method.
Background technology
Aromatic aldehyde, especially p-tolyl aldehyde (PTAL) is the important organism of synthetic many fine chemicals, as can be used for compound perfume and food flavor(ing)s such as synthetic cloves, lily, the oxide compound terephthalic acid (PTA) of p-tolyl aldehyde is an important monomer of producing polyester (PET).
The production method of alkyl aromatic aldehyde is divided into two kinds at present: high-temperature oxidation and carbonyl process.High-temperature oxidation is under hot conditions the alkyl of Alkylaromatics (the alkyl number on the phenyl ring is more than or equal to 2) to be oxidized to aldehyde radical, obtains alkyl aromatic aldehyde.Carbonyl process is that carbonylation reaction generation alkyl aromatic aldehyde is taken place under catalyst action for Alkylaromatics and carbon monoxide.There is the low problem of Alkylaromatics utilization ratio in high-temperature oxidation; In carbonyl process, therefore Alkylaromatics, carbon monoxide aboundresources and relatively inexpensive, and Alkylaromatics utilization ratio height more and more cause people's attention.
For example, US6320083 discloses a kind of method of using ionic liquid to be prepared alkyl aromatic aldehyde by carbonyl process, this method is included under the pressure of 0-100 ℃ temperature and 1.47-19.6 MPa, in the presence of acidic ion liquid, with Alkylaromatics and reaction of carbon monoxide, form the alkyl aromatic aldehyde mixture of reaction products.Wherein, Alkylaromatics comprises toluene, dimethylbenzene, 1 and 1,2,5-Three methyl Benzene.Described acidic ion liquid is made up of Organohalogen compounds and metal halide, and the mol ratio of metal halide and Organohalogen compounds is 1-3, is preferably 1.5-3, more preferably 2-3.The various isomerss that in the alkyl aromatic aldehyde mixture of reaction products that obtains, contain acidic ion liquid and alkyl aromatic aldehyde.Wherein, alkyl aromatic aldehyde is in complex status, is not unbound state, and catalyzer is that acidic ion liquid also participates in forming complex compound.In order to separate from the alkyl aromatic aldehyde mixture of reaction products, US6320083 proposes to use selectivity volatilization method and liquid-liquid extraction method.Wherein, liquid-liquid extraction method comprises insoluble solvent is joined in the described mixture of reaction products, this insoluble solvent and acidic ion liquid layering, the alkyl aromatic aldehyde reaction product is transferred in this insoluble solvent, and then adopts conventional method that the alkyl aromatic aldehyde reaction product is separated from insoluble solvent.Described insoluble solvent comprises benzene and toluene.The selectivity volatilization method is meant aldehyde product is changed into gaseous form, and ionic liquid is not converted to gaseous form, thereby the two is separated.The temperature that the selectivity volatilization method is carried out is at least 90 ℃, is preferably 100-350 ℃, and preferably carries out under decompression or vacuum condition.
Because in the alkyl aromatic aldehyde mixture of reaction products that obtains, there is very strong complexing action power between the alkyl aromatic aldehyde reaction product and between catalyzer and the alkyl aromatic aldehyde reaction product, when therefore using the selectivity volatilization method to separate, need the more energy of loss, and solution causes the polymerization of aldehyde; Percentage extraction is not high when using liquid-liquid extraction method to separate, and needs to use a large amount of organic solvents, so the existing method for preparing alkyl aromatic aldehyde by carbonyl process exists aldehyde product and catalyzer to be difficult to isolating problem.
Summary of the invention
The objective of the invention is to overcome and existingly prepare aldehyde product and the catalyzer that the method for alkyl aromatic aldehyde exists by carbonyl process and be difficult to isolating problem, a kind of separation method of alkyl aromatic aldehyde is provided, uses this separation method easily the alkyl aromatic aldehyde reaction product to be separated from the alkyl aromatic aldehyde mixture of reaction products.
Another object of the present invention provides the preparation method of the alkyl aromatic aldehyde that uses this separation method.
The invention provides a kind of separation method of alkyl aromatic aldehyde, this method comprises from the complex state alkyl aromatic aldehyde mixture of reaction products of carbonyl process preparation isolates the free state alkyl aromatic aldehyde, this mixture of reaction products contains alkyl aromatic aldehyde and acidic ion liquid, described acidic ion liquid contains metal halide and Organohalogen compounds, wherein, this method also is included in separates before the alkyl aromatic aldehyde from the alkyl aromatic aldehyde mixture of reaction products of carbonyl process preparation, in mixture of reaction products, add Organohalogen compounds again, make the mol ratio of Organohalogen compounds and metal halide in the described mixture of reaction products greater than 1.
The present invention also provides a kind of preparation method of aromatic aldehyde, and this method is included in acidic ion liquid and exists down, with alkyl aromatic compound and carbon monoxide contact reacts, obtains mixture of reaction products; Isolate alkyl aromatic aldehyde, described acidic ion liquid contains metal halide and Organohalogen compounds, wherein, isolating method is included in the alkyl aromatic aldehyde mixture of reaction products of carbonyl process preparation and adds Organohalogen compounds, isolates alkyl aromatic aldehyde then from mixture of reaction products.
In alkyl aromatic aldehyde separation method provided by the invention, owing in described mixture of reaction products, added Organohalogen compounds as the decomplexing agent, help making the aldehyde product of complex status to be transformed into unbound state, therefore make the easy and catalyst separating of alkyl aromatic aldehyde reaction product.
Embodiment
The separation method of alkyl aromatic aldehyde provided by the invention comprises from the complex state alkyl aromatic aldehyde mixture of reaction products of carbonyl process preparation isolates the free state alkyl aromatic aldehyde, this mixture of reaction products contains alkyl aromatic aldehyde and acidic ion liquid, described acidic ion liquid contains metal halide and Organohalogen compounds, wherein, this method also is included in separates before the alkyl aromatic aldehyde from the alkyl aromatic aldehyde mixture of reaction products of carbonyl process preparation, in mixture of reaction products, add Organohalogen compounds again, make the mol ratio of Organohalogen compounds and metal halide in the described mixture of reaction products greater than 1.
According to separation method provided by the invention, described mixture of reaction products contains alkyl aromatic aldehyde and acidic ion liquid.
Alkyl aromatic aldehyde can be in tolyl aldehyde, dimethylbenzaldehyde and the trimethylbenzaldehyde one or more.Alkyl aromatic aldehyde is preferably p-tolyl aldehyde, o-methyl-benzene formaldehyde and a tolyl aldehyde.
Described acidic ion liquid contains metal halide and Organohalogen compounds.Described metal halide can be selected from one or more in aluminum chloride, aluminum bromide, aluminum iodide and the iron trichloride, is preferably aluminum chloride.Molar content in ionic liquid is greater than 50% the time when metal halide such as aluminum chloride, and ionic liquid presents Lewis acidity, and the anionic form that exists is with AlCl
3The molar fraction difference can be AlCl
4 -, Al
2Cl
7 -, Al
3Cl
10 -Deng, acidic ion liquid plays catalyzer, because acidic ion liquid is in a liquid state, more helps lock out operation and recycles.
The Organohalogen compounds that acidic ion liquid contains are made up of organic cation and halide anion.The positively charged ion of Organohalogen compounds can be selected from by alkyl imidazole positively charged ion (C
3H
0-4N
2R
1-5 +, 1-5 alkyl substituent, wherein R of 1-5 position promptly can be arranged on the imidazole ring
1-5Can be the identical or different carbonatomss alkyl that is 1-16), alkyl pyridine positively charged ion (C
5H
5NR
+, wherein R is that carbonatoms is the alkyl of 1-16), quaternary ammonium salt cationic (R
1R
2R
3R
4N
+, R wherein
1, R
2, R
3, R
4Can be the identical or different carbonatomss alkyl that is 1-16), quaternary alkylphosphonium salt positively charged ion (R
1R
2R
3R
4P
+, R wherein
1, R
2, R
3, R
4Can be the identical or different carbonatomss alkyl that is 1-16) and above-mentioned cationic derivative or with the similar organic cation of above-mentioned cationic structural in one or more.The negatively charged ion of Organohalogen compounds can be selected from Cl
-, Br
-Or I
-, be preferably Cl
-
In acidic ion liquid, the mol ratio of metal halide and Organohalogen compounds is 1.2-2.5, is preferably 1.8-2.2.
The Organohalogen compounds that add in mixture of reaction products can be selected from the various Organohalogen compounds in the above-mentioned acidic ion liquid, and are preferably identical with the Organohalogen compounds that form described acidic ion liquid.
The Organohalogen compounds that add can destroy complexing action power stronger between alkyl aromatic aldehyde product and the catalyzer as the decomplexing agent, the alkyl aromatic aldehyde product is transformed to free state by complex status, thereby help from mixture of reaction products, isolating the free state product.The consumption of Organohalogen compounds makes the mol ratio of Organohalogen compounds and metal halide in the mixture of reaction products greater than 1, is preferably 1.2-2.5.
In mixture of reaction products, add after the Organohalogen compounds, can adopt existing various separation method from mixture of reaction products, to isolate the alkyl aromatic aldehyde product.For example, can adopt extraction process, freeze crystallization or distillation under vacuum from the alkyl aromatic aldehyde mixture of reaction products, to isolate alkyl aromatic aldehyde.
The kind of the employed extraction agent of extraction process and consumption, extraction temperature and extraction mode have been that those skilled in the art are in common knowledge.
Extraction agent can be various varsols, is preferably the aliphatic hydrocarbon that contains 4-16 carbon atom and in the aromatic hydrocarbon one or more, more preferably contains the aliphatic hydrocarbon of 6-10 carbon atom and in the toluene one or more.
The temperature of extraction is 10-100 ℃, preferred 20-40 ℃.
Described extraction can be carried out one or many, and repeatedly extraction can make more reaction product such as p-tolyl aldehyde, o-methyl-benzene formaldehyde, a tolyl aldehyde transfer in the extraction agent.
The volume ratio of described extraction agent and mixture of reaction products is 0.2-5.0, is preferably 0.5-4.5.
The temperature of freezing and crystallizing is preferably-6 ℃ to-100 ℃, more preferably-6 ℃ to-20 ℃.
The temperature of underpressure distillation is 40-150 ℃, is preferably 40-120 ℃; Pressure (absolute pressure) is the 0-0.08 MPa, is preferably the 0.001-0.04 MPa.
From described product mixtures, isolate after the alkyl aromatic aldehyde, can in remaining mixture, add a certain amount of metal halide, form acidic ion liquid again; The add-on of metal halide makes that the mol ratio of metal halide and Organohalogen compounds is 1.2-2.5 in the remaining mixture, is preferably 1.8-2.2.Can also heat remaining mixture, the part Organohalogen compounds are decomposed and from mixture, remove, form acidic ion liquid again; The temperature of heating is 50-200 ℃, is preferably 80-150 ℃, and the time of heating makes that the mol ratio of metal halide and Organohalogen compounds is 1.2-2.5 in the remaining mixture, is preferably 1.8-2.2.Again the acidic ion liquid of Xing Chenging can be reused, and prepares the catalyzer of alkyl aromatic aldehyde as carbonyl process.
The preparation method of alkyl aromatic aldehyde provided by the invention is included in acidic ion liquid and exists down, with alkyl aromatic compound and carbon monoxide contact reacts, obtains mixture of reaction products; Isolate alkyl aromatic aldehyde, described acidic ion liquid contains metal halide and Organohalogen compounds, and wherein, isolating method adopts separation method provided by the invention.
According to the preparation method of alkyl aromatic aldehyde provided by the invention, except isolating method adopted separation method provided by the invention, other step and condition can adopt step of the prior art and condition.
According to the preparation method of alkyl aromatic aldehyde provided by the invention, wherein, described acidic ion liquid contains metal halide and Organohalogen compounds.Described metal halide can be selected from one or more in aluminum chloride, aluminum bromide, aluminum iodide and the iron trichloride, is preferably aluminum chloride.Molar content in ionic liquid is greater than 50% the time when metal halide such as aluminum chloride, and ionic liquid presents Lewis acidity, and the anionic form that exists is with AlCl
3The molar fraction difference can be AlCl
4 -, Al
2Cl
7 -, Al
3Cl
10 -Deng, acidic ion liquid plays catalyzer, because acidic ion liquid is in a liquid state, more helps lock out operation and recycles.
Described Organohalogen compounds are made up of organic cation and halide anion.The positively charged ion of Organohalogen compounds can be selected from by alkyl imidazole positively charged ion (C
3H
0-4N
2R
1-5 +, 1-5 alkyl substituent, wherein R of 1-5 position promptly can be arranged on the imidazole ring
1-5Can be the identical or different carbonatomss alkyl that is 1-16), alkyl pyridine positively charged ion (C
5H
5NR
+, wherein R is that carbonatoms is the alkyl of 1-16), quaternary ammonium salt cationic (R
1R
2R
3R
4N
+, R wherein
1, R
2, R
3, R
4Can be the identical or different carbonatomss alkyl that is 1-16), quaternary alkylphosphonium salt positively charged ion (R
1R
2R
3R
4P
+, R wherein
1, R
2, R
3, R
4Can be the identical or different carbonatomss alkyl that is 1-16) and above-mentioned cationic derivative or with the similar organic cation of above-mentioned cationic structural in one or more.The negatively charged ion of Organohalogen compounds can be selected from Cl
-, Br
-Or I
-, be preferably Cl
-
In acidic ion liquid, the mol ratio of metal halide and Organohalogen compounds is 1.2-2.5, is preferably 1.8-2.2.
The Organohalogen compounds in the described acidic ion liquid and the mol ratio of alkyl aromatic compound are 1.2-5.0, are preferably 1.2-2.0.
Described alkyl aromatic compound can be selected from toluene, dimethylbenzene, 1 and 1,2, one or more in the 5-Three methyl Benzene.Dimethylbenzene comprises o-Xylol, m-xylene and p-Xylol.Described alkyl aromatic compound is preferably toluene.
The catalytic temperature of alkyl aromatic compound and carbon monoxide is 0-60 ℃, is preferably 20-40 ℃; Time is 0.5-8 hour, is preferably 2-4 hour.Wherein the dividing potential drop of carbon monoxide is the 1.0-8.0 MPa, is preferably the 2.5-4.0 MPa.
The present invention will be described in more detail below in conjunction with embodiment.
Preparation embodiment 1
This preparation embodiment is used to prepare the alkyl aromatic aldehyde mixture of reaction products.
In 300 milliliters of zirconium material autoclaves, add 100 gram [bmim] Cl-AlCl
3Ionic liquid ([bmim] Cl and AlCl
3Mol ratio be 1:2, [bmim] Cl represents chloro 1-butyl-3-Methylimidazole) and 12 milliliters of (0.1135 mole) toluene, with behind the air in the nitrogen replacement still dividing potential drop of carbon monoxide being risen to 3.0 MPas, low whipping speed is that 750 rev/mins, temperature are under 40 ℃ the condition, reacted 5.0 hours, and obtained mixture of reaction products.Gas chromatographic analysis shows that the transformation efficiency of toluene is 51.2%, and the selectivity of p-tolyl aldehyde is 86.3%, and the selectivity of o-methyl-benzene formaldehyde is 11.5%, and the selectivity of a tolyl aldehyde is 2.2%.
Embodiment 1
This embodiment is used to illustrate separation method provided by the invention.
In 100 milliliters triangular flask, add the mixture of reaction products that 5 milliliters of preparation embodiment 1 obtain, and add [bmim] Cl, make [bmim] Cl and AlCl in the mixture
3Mol ratio be 2:1.Add 20 milliliters of octanes then, mixed 5 minutes, static phase-splitting uses separating funnel two-layerly up and down to separate.Analyze octane solution with marker method, the result shows that the percentage extraction of tolyl aldehyde is 35.5%.
Comparative Examples 1
This Comparative Examples is used to illustrate the method for prior art separation alkyl aromatic aldehyde.
The mixture of reaction products that 5 milliliters of preparations of adding embodiment 1 obtain in 100 milliliters triangular flask adds 20 milliliters of octanes then, mixes 5 minutes, and static phase-splitting uses separating funnel two-layerly up and down to separate.Analyze octane solution with marker method, the result shows that the percentage extraction of tolyl aldehyde is 0%.
Embodiment 2
This embodiment is used to illustrate separation method provided by the invention.
In 100 milliliters triangular flask, add the mixture of reaction products that 5 milliliters of preparation embodiment 1 obtain, and add [bmim] Cl, make [bmim] Cl and AlCl in the mixture
3Mol ratio be 2:1.Add 20 milliliters of toluene then, mixed 5 minutes, static phase-splitting uses separating funnel two-layerly up and down to separate.Analyze toluene solution with marker method, the result shows that the percentage extraction of tolyl aldehyde is 58.3%.
Comparative Examples 2
This Comparative Examples is used to illustrate the method for prior art separation alkyl aromatic aldehyde.
The mixture of reaction products that 5 milliliters of preparations of adding embodiment 1 obtain in 100 milliliters triangular flask adds 20 milliliters of toluene then, mixes 5 minutes, and static phase-splitting uses separating funnel two-layerly up and down to separate.Analyze toluene solution with marker method, the result shows that the percentage extraction of tolyl aldehyde is 14.0%.
Embodiment 3
This embodiment is used to illustrate separation method provided by the invention.
According to embodiment 1 identical operations step, with n-hexane extraction three times, the consumption of normal hexane is 20.0 milliliters at every turn.The result shows that the percentage extraction of tolyl aldehyde is followed successively by 35.5%, 37.4%, 35.2%, and therefore through after three extractions, total percentage extraction of tolyl aldehyde is 73.8%.
Embodiment 4
This embodiment is used to illustrate separation method provided by the invention.
According to embodiment 1 identical operations step, with toluene extraction three times, the consumption of toluene is 20.0 milliliters at every turn.The result shows that the percentage extraction of tolyl aldehyde is followed successively by 58.3%, 61.8%, 70.2%, and therefore through after three extractions, total percentage extraction of tolyl aldehyde is 95.2%.
Embodiment 5
This embodiment is used to illustrate separation method provided by the invention.
In 100 milliliters triangular flask, add the mixture of reaction products that 50 milliliters of preparation embodiment 1 obtain, and add [bmim] Cl, make [bmim] Cl and AlCl in the mixture
3Mol ratio be 1.8:1.Under-6 ℃, carry out freezing and crystallizing then, obtain tolyl aldehyde between 1.24 gram p-tolyl aldehydes, 0.06 gram o-methyl-benzene formaldehyde and 0.03 gram respectively.
Comparative Examples 3
This embodiment is used to illustrate the separation method that does not add the decomplexing agent.
In 100 milliliters triangular flask, add the mixture of reaction products that 50 milliliters of preparation embodiment 1 obtain, under-6 ℃, carry out freezing and crystallizing, obtain tolyl aldehyde between 0.65 gram p-tolyl aldehyde, 0.04 gram o-methyl-benzene formaldehyde and 0.01 gram respectively.
Embodiment 6
This embodiment is used to illustrate separation method provided by the invention.
In 100 milliliters triangular flask, add the mixture of reaction products that 50 milliliters of preparation embodiment 1 obtain, and add [bmim] Cl, make [bmim] Cl and AlCl in the mixture
3Mol ratio be 1.8:1.Distillation 0.5 hour under 120 ℃, 0.02 MPa then, obtain respectively 1.5 gram p-tolyl aldehydes, 0.2 gram o-methyl-benzene formaldehyde and 0.03 can between tolyl aldehyde.
Comparative Examples 4
This embodiment is used to illustrate the separation method that does not add the decomplexing agent.
In 100 milliliters triangular flask, add the mixture of reaction products that 50 milliliters of preparation embodiment 1 obtain, distillation is 0.5 hour under 120 ℃, 0.02 MPa, obtains tolyl aldehyde between 0.1 gram p-tolyl aldehyde, 0.01 gram o-methyl-benzene formaldehyde and 0.002 gram respectively.
Embodiment 7
This embodiment is used for illustrating that preparation method's decomplexing agent of alkyl aromatic aldehyde provided by the invention can reuse.
In preparation embodiment 1 described mixture of reaction products, add [bmim] Cl, make [bmim] Cl and AlCl
3Mol ratio be 2:1, with 200.0 ml n-hexanes extraction five times.
(contain [bmim] Cl and AlCl toward extracting phase then
3Solution) in add AlCl
3, make ([bmim] Cl and AlCl
3Mol ratio return to 1:2, form new acidic ion liquid.Get 100 these acidic ion liquids of gram and make catalyzer, add 17 milliliters of toluene, carry out the carbonylation reaction 2 hours of above-mentioned toluene again.Gas chromatographic analysis shows that the transformation efficiency of toluene is 50.1%, and the selectivity of p-tolyl aldehyde is 88.1%, and the selectivity of o-methyl-benzene formaldehyde is 10.9%, and the selectivity of a tolyl aldehyde is 1.0%.
Claims (21)
1, a kind of separation method of alkyl aromatic aldehyde, this method comprises from the complex state alkyl aromatic aldehyde mixture of reaction products of carbonyl process preparation isolates the free state alkyl aromatic aldehyde, this mixture of reaction products contains alkyl aromatic aldehyde and acidic ion liquid, described acidic ion liquid is made up of metal halide and Organohalogen compounds, it is characterized in that, this method also is included in separates before the alkyl aromatic aldehyde from the alkyl aromatic aldehyde mixture of reaction products of carbonyl process preparation, in mixture of reaction products, add the Organohalogen compounds of forming by organic cation and halide anion again, make the mol ratio of Organohalogen compounds and metal halide in the described mixture of reaction products greater than 1.
2, method according to claim 1, wherein, the add-on of Organohalogen compounds makes that the mol ratio of Organohalogen compounds and metal halide is 1.2-2.5 in the mixture of reaction products.
3, method according to claim 1, wherein, the Organohalogen compounds in the acidic ion liquid are the Organohalogen compounds of being made up of organic cation and halide anion.
4, method according to claim 3, wherein, the positively charged ion of Organohalogen compounds is selected from a kind of in the quaternary ammonium salt cationic, quaternary alkylphosphonium salt positively charged ion; The negatively charged ion of Organohalogen compounds is Cl
-, Br
-Or I
-
5, method according to claim 4, wherein, quaternary ammonium salt cationic is alkyl imidazole positively charged ion or alkyl pyridine positively charged ion.
6, method according to claim 1, wherein, metal halide is selected from one or more in aluminum chloride, aluminum bromide, aluminum iodide and the iron trichloride.
7, method according to claim 1, wherein, alkyl aromatic aldehyde is one or more in tolyl aldehyde, dimethylbenzaldehyde and the trimethylbenzaldehyde.
8, method according to claim 7, wherein, alkyl aromatic aldehyde is p-tolyl aldehyde, o-methyl-benzene formaldehyde and a tolyl aldehyde.
9, method according to claim 1, wherein, the method for isolating alkyl aromatic aldehyde from the alkyl aromatic aldehyde mixture of reaction products of carbonyl process preparation is extraction, freezing and crystallizing or underpressure distillation.
10, method according to claim 9 wherein, extracts employed extraction agent and is selected from the aliphatic hydrocarbon that contains 4-16 carbon atom and in the aromatic hydrocarbon one or more; The volume ratio of extraction agent and mixture of reaction products is 0.2-5.0.
11, method according to claim 9, wherein, the temperature of freezing and crystallizing is-6 ℃ to-100 ℃.
12, method according to claim 9, wherein, the temperature of underpressure distillation is 40 ℃-150 ℃, pressure is the 0-0.08 MPa.
13, a kind of preparation method of alkyl aromatic aldehyde, this method are included in acidic ion liquid and exist down, with Alkylaromatics and carbon monoxide contact reacts, obtain mixture of reaction products; Isolate alkyl aromatic aldehyde, described acidic ion liquid is made up of metal halide and Organohalogen compounds, it is characterized in that, described isolating method is any described method among the claim 1-12.
14, method according to claim 13, wherein, described acidic ion liquid contains metal halide and Organohalogen compounds, and the mol ratio of metal halide and Organohalogen compounds is 1.2-2.5.
15, method according to claim 14, wherein, metal halide is selected from one or more in aluminum chloride, aluminum iodide, aluminum bromide and the iron trichloride.
16, method according to claim 14, wherein, described Organohalogen compounds are the Organohalogen compounds of being made up of organic cation and halide anion.
17, method according to claim 16, wherein, the positively charged ion of Organohalogen compounds is selected from a kind of in the quaternary ammonium salt cationic, quaternary alkylphosphonium salt positively charged ion; The negatively charged ion of Organohalogen compounds is Cl
-, Br
-Or I
-
18, method according to claim 17, wherein, quaternary ammonium salt cationic is alkyl imidazole positively charged ion or alkyl pyridine positively charged ion.
19, method according to claim 13, wherein, the Organohalogen compounds in the described acidic ion liquid and the mol ratio of Alkylaromatics are 1.2-5.0.
20, method according to claim 13, wherein, described Alkylaromatics is toluene, dimethylbenzene and 1,2, the 5-Three methyl Benzene.
21, method according to claim 13, wherein, the catalytic condition of described Alkylaromatics and carbon monoxide is that temperature is that 0-60 ℃, time are that 0.5-8 hour, the dividing potential drop of carbon monoxide are the 1.0-8.0 MPa.
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