CN102757344A - Method for preparing methyl succinate from ionic liquid catalyst - Google Patents
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Abstract
The invention provides a meethod for preparing methyl succinate from an ionic liquid catalyst. Particularly, the invention relates to a method for preparing methyl succinate through mono-methyl succinate and methanol esterification. In the method, mono-methyl succinate and methanol are taken as reactants, imidazole ionic liquid and pyridine ionic liquid are taken as catalysts, and under the nitrogen atmosphere, the reaction pressure is 0.1 to 3Mpa, the reaction temperature is 90 to 150 DEG C, the reaction time is 6 to 12 hours, and the mole ratio of ionic liquid to mono-methyl succinate to methanol: (0.1 to 2):1:(1 to 10). The catalyst used in the invention is simple in preparation process, the raw material is easily available, no by-product is generated during the preparation process, the reaction conversion rate is high, the selectivity is good, the required equipment is less, the cost is low, and methyl succinat is suitable for large-scale industrial production.
Description
Technical field
The present invention relates to a kind ofly prepare the method for methyl-succinate, belong to the technical field of organic chemical reactions method with ionic-liquid catalyst.
Background technology
Methyl-succinate is a kind of important chemical product, is mainly used in food, chemical industry, pharmaceutical industries.Traditional methyl-succinate is mainly made through esterification by Succinic Acid, cis-butenedioic anhydride and methyl alcohol.The traditional esterification method adopts mineral acids such as sulfuric acid, phosphoric acid to realize as catalyzer mostly, but the remaining spent acid in reaction back can cause environmental pollution.
Ionic liquid is the one type of environmentally friendly reagent that receives publicity day by day in recent years, has good stability, and is non-volatile, with advantage such as the organism solvability is adjustable.Ionic liquid is a kind of a kind of salt that at room temperature exists with liquid form; Have many special nature; Very low almost nil like its saturated vapor pressure; Can dissolve many inorganicss and organism, not have corrodibility, can prepare different ionic liquids through the kind and the quantity of allocating its zwitterion.Also get more and more about ion liquid kind and related field at present.
It is that catalyzer and reaction medium have been realized the alcoholic acid esterification reaction with aluminate ion liquid that bibliographical information is arranged, but this type ionic liquid is easy to hydrolysis; In recent years bibliographical information had been arranged the more stable imidazoles of water, pyridines protonic acid ionic liquid are widely used in acid-catalyzed esterification reaction, this type catalyzer has the active and repetition practicality of catalytic esterification preferably.Patent CN1405140 has reported that utilizing ionic liquid [Hmin]+BF4-is catalyzer and solvent, and the aliphatic or aromatic acid and the straight chain alcohol process of carrying out esterification stir heating; Leave standstill, gravity settling, separatory gets esterified prod; Transformation efficiency has reached 80-100%, and selectivity is 100%.Patent CN101172949A discloses a kind of method of sulfonic group functionalization morpholine hyamine ion liquid catalytic esterification; Characteristic is that the morpholine hyamine ion liquid with sulfonic functional is catalyzer, solvent and the dewatering agent of esterification; Add-on is total mole 0.5-100% of pure and mild acid; 10-140 ℃ of reaction 0.5-12 hour, the transformation efficiency of acid was 86.3%, and the selectivity of ester has reached 100%.
Summary of the invention
The invention provides a kind of with the ionic liquid-catalyzed method for preparing methyl-succinate; When this method has overcome prior art and has been catalyzer with the dilute sulphuric acid to the pollution of environment and to the corrosion on Equipment problem; And severe reaction conditions in the solid acid catalyst catalysis process, the problem that the esterification products yield is low.
The invention provides a kind of method that makes monomethyl succinate and methanol esterification prepare methyl-succinate, it is characterized in that, use monomethyl succinate and alcohol as reactant; As catalyzer, under nitrogen atmosphere, reaction pressure is 0.1-3Mpa with imidazoles, pyridines ionic liquid; Temperature of reaction is 90 ~ 150 ℃; Reaction times is 6-12h, and the mol ratio of ionic liquid, monomethyl succinate, alcohol is (0.1-2): 1: (1-10)
Wherein, described ionic-liquid catalyst is for to stablize, to be tart imidazoles, pyridines ionic liquid to water,
The cationic structure of said imidazoles is as follows:
Wherein, m is 0~15 integer, and n is 1~10 integer, and l is 0~15 integer; R
1Be C
1~C
10Alkyl or C
6~C
12Aryl, preferably, R
1Be C
1~C
6Alkyl or phenyl (Ph).
The cationic structure of said pyridines is as follows:
Wherein, m is 0~15 integer, and n is 1~10 integer, and l is 0~15 integer; R
1Be C
1~C
10Alkyl or C
6~C
12Aryl, preferred R
1Be C
1~C
6Alkyl or phenyl (Ph).
The anionicsite of said catalyzer is selected from CH
3PhSO
3 -, CF
3SO
3 -, HSO
4 -, SO
4 2-, HCOO
-, CH
3COO
-, CF
3COO
-, PO
4 3-, HPO
4 2-, H
2PO
4 -And N (CH
3SO
2)
2 -In.
Said preparation method of ionic liquid is following:
1) with imidazoles or pyridinium salt and equimolar acid: CH
3PhSO
3H, CF
3SO
3H, H
2SO
4, HCOOH, CH
3COOH, CF
3COOH, H
3PO
4, N (CH
3SO
2)
2H, HBF
4Or CF
3, stirred 12-24 hour at 50-120 ℃;
2) reaction finishes, and removes moisture 50-80 ℃ of underpressure distillation, obtains imidazoles or pyridinium salt ionic liquid.
3) ionic liquid is washed 1-4 time with ether.
4) 40-60 ℃ of underpressure distillation obtains high-purity imidazoles, pyridinium salt ionic liquid.
Beneficial effect of the present invention:
Have Bronsted acidity when 1) said ionic-liquid catalyst has the ionic liquid characteristic, stable to water, viscosity is low.Has catalysis, especially the acid catalyzed esterification function.
2) have ion liquid characteristic, as: but operating temperature range is wide, and steam forces down, and inorganics and organism are had good dissolving ability.
3) Preparation of catalysts technology is simple, and raw material is easy to get, no coupling product in the preparation process, and reaction conversion ratio is high, and selectivity is good, and required equipment is few, and cost is low, is applicable to large-scale industrial production.
Description of drawings
Fig. 1 is the mass spectrum of the methyl-succinate prepared according to the present invention.
Fig. 2 is the nuclear magnetic spectrogram of the methyl-succinate prepared according to the present invention.
Embodiment
Experimental raw:
In following examples; N-Methylimidazole, bromination ethane, tosic acid, acetone, ether, sodium tetrafluoroborate, sodium sulfate, yellow soda ash, 2-picoline and methyl alcohol are available from Chemical Reagent Co., Ltd., Sinopharm Group, and monomethyl succinate is available from Aladdin reagent ltd.
Further specify the inventive method and effect through embodiment below, but the invention is not restricted to following examples.
Embodiment 1: prepare methyl-succinate through tosic acid 1-ethyl-ionic liquid-catalyzed monomethyl succinate of 3-methylimidazole salt
In round-bottomed flask, add 5.21g (0.1mol) N-Methylimidazole and 10.9g (0.1mol) bromination ethane, Heating temperature to 80 ℃, reaction 24h; After question response stops fully; Be cooled to room temperature and separate out white crystal, put into loft drier, obtain white crystal 13.85g at 45 ℃ of dry 10h.White crystal is 1-ethyl-3 a Methylimidazole bromine salt.
With the 1-ethyl-3 Methylimidazole bromine salt 13.85g (0.098mol) of system, 16.88g (0.098mol) tosic acid and 40ml acetone join in the flask, and temperature of reaction is 75 ℃, condensing reflux.Reaction times 20h, reaction finishes, and removes moisture 70 ℃ of underpressure distillation, obtains tosic acid 1-ethyl-3-methylimidazole salt ionic liquid.With ether washing 4 times, 60 ℃ of underpressure distillation obtain high-purity tosic acid 1-ethyl-3-methylimidazole salt ionic liquid with ionic liquid.In vacuum drying oven,, obtain transparent ionic liquid 19.48g in 45 ℃ of dry 10h.
With the 2.1g ionic liquid, 13.2g monomethyl succinate and 12g methyl alcohol are put into autoclave, feed nitrogen and make the pressure in the reactor drum rise to 1Mpa; Stir, Heating temperature is 100 ℃, and the reaction times is 10h; After reaction solution was cooled to room temperature, extraction obtained methyl-succinate, and transformation efficiency is 84%; Selectivity to remove unreacted reactant, is reused ion liquid abstraction greater than 96%.
The mass spectrum of resulting methyl-succinate is as shown in Figure 1, and nuclear magnetic spectrogram is as shown in Figure 2.
Embodiment 2: prepare methyl-succinate through 1-ethyloic-3-ethyl imidazol(e) tetrafluoroborate ion liquid catalysis monomethyl succinate
In round-bottomed flask, add 5.21g (0.1mol) N-Methylimidazole and 10.9g (0.1mol) bromination ethane, Heating temperature to 80 ℃, reaction 24h; After question response stops fully; Be cooled to room temperature and separate out white crystal, put into loft drier, obtain white crystal 13.85g at 45 ℃ of dry 10h.White crystal is 1-ethyl-3 a Methylimidazole bromine salt.
With the 1-ethyl-3 Methylimidazole bromine salt 13.85g of system, 10.75g (0.098mol) sodium tetrafluoroborate and 40ml acetone join in the flask, and temperature of reaction is 80 ℃, condensing reflux.Reaction times 20h, reaction finishes, and removes moisture 70 ℃ of underpressure distillation, obtains 1-ethyloic-3-ethyl imidazol(e) tetrafluoroborate ion liquid.With ether washing 4 times, 60 ℃ of underpressure distillation obtain high-purity 1-ethyloic-3-ethyl imidazol(e) tetrafluoroborate ion liquid with ionic liquid.With 45 ℃, dry 10h obtains transparent ionic liquid 19.48g in vacuum drying oven.
With the 2.1g ionic liquid, 13.2g monomethyl succinate and 12g methyl alcohol are put into autoclave, feed nitrogen and make the pressure in the reactor drum rise to 1Mpa; Stir, Heating temperature is 100 ℃, and the reaction times is 12h; After reaction solution was cooled to room temperature, extraction obtained methyl-succinate, and transformation efficiency is 85%; Selectivity to remove unreacted reactant, is reused ion liquid abstraction greater than 95%.
The mass spectrum of resulting methyl-succinate is as shown in Figure 1, and nuclear magnetic spectrogram is as shown in Figure 2.
Embodiment 3: prepare methyl-succinate through 1-ethyloic-3-ethyl imidazol(e) sulfate ion liquid catalyst monomethyl succinate
In round-bottomed flask, add 5.21g (0.1mol) N-Methylimidazole and 10.9g (0.1mol) bromination ethane, Heating temperature to 80 ℃, reaction 24h; After question response stops fully; Be cooled to room temperature and separate out white crystal, put into loft drier, obtain white crystal 13.85g at 45 ℃ of dry 10h.White crystal is 1-ethyl-3 a Methylimidazole bromine salt.
With the 1-ethyl-3 Methylimidazole bromine salt 13.85g (0.098mol) of system, 13.92g (0.098mol) sodium sulfate and 40ml acetone join in the flask, and temperature of reaction is 75 ℃, condensing reflux.Reaction times 20h, reaction finishes, and removes moisture 60 ℃ of underpressure distillation, obtains 1-ethyloic-3-ethyl imidazol(e) sulfate ion liquid.With ether washing 4 times, 60 ℃ of underpressure distillation obtain high-purity 1-ethyloic-3-ethyl imidazol(e) sulfate ion liquid with ionic liquid.With 45 ℃, dry 10h obtains transparent ionic liquid 21.48g in vacuum drying oven.
With the 2.1g ionic liquid, 13.2g monomethyl succinate and 12g methyl alcohol are put into autoclave, feed nitrogen and make the pressure in the reactor drum rise to 0.1Mpa; Stir, Heating temperature is 120 ℃, and the reaction times is 10h; After reaction solution was cooled to room temperature, extraction obtained methyl-succinate, and transformation efficiency is 95%; Selectivity to remove unreacted reactant, is reused ion liquid abstraction greater than 99%.
The mass spectrum of resulting methyl-succinate is as shown in Figure 1, and nuclear magnetic spectrogram is as shown in Figure 2.
Embodiment 4: prepare methyl-succinate through 1-ethyloic-3-ethyl imidazol(e) carbonate ion liquid catalyst monomethyl succinate
In round-bottomed flask, add 5.21g (0.1mol) N-Methylimidazole and 10.9g (0.1mol) bromination ethane, Heating temperature to 80 ℃, reaction 24h; After question response stops fully; Be cooled to room temperature and separate out white crystal, put into loft drier, obtain white crystal 13.85g at 45 ℃ of dry 10h.White crystal is 1-ethyl-3 a Methylimidazole bromine salt.
With the 1-ethyl-3 Methylimidazole bromine salt 13.85g (0.098mol) of system, 10.39g (0.098mol) yellow soda ash and 40ml acetone join in the flask, and temperature of reaction is 75 ℃, condensing reflux.Reaction times 20h, reaction finishes, and removes moisture 50-80 ℃ of underpressure distillation, obtains 1-ethyloic-3-ethyl imidazol(e) carbonate ion liquid.With ether washing 4 times, 60 ℃ of underpressure distillation obtain high-purity 1-ethyloic-3-ethyl imidazol(e) carbonate ion liquid with ionic liquid.With 45 ℃, dry 10h obtains transparent ionic liquid 18.42g in vacuum drying oven.
With the 2.1g ionic liquid, 13.2g monomethyl succinate and 12g methyl alcohol are put into autoclave, feed nitrogen and make the pressure in the reactor drum rise to 1Mpa; Stir, Heating temperature is 120 ℃, and the reaction times is 9h; After reaction solution was cooled to room temperature, extraction obtained methyl-succinate, and transformation efficiency is 89%; Selectivity to remove unreacted reactant, is reused ion liquid abstraction greater than 97%.
The mass spectrum of resulting methyl-succinate is as shown in Figure 1, and nuclear magnetic spectrogram is as shown in Figure 2.
Embodiment 5: prepare methyl-succinate through tosic acid 1-ethyl-2-picoline salt ion liquid catalyst monomethyl succinate
In round-bottomed flask, add 9.31g (0.1mol) 2-picoline and 10.9g (0.1mol) bromination ethane, Heating temperature to 80 ℃, reaction 24h; After question response stops fully; Be cooled to room temperature and separate out white crystal, put into loft drier, obtain white crystal 19.19g at 45 ℃ of dry 10h.White crystal is 1-ethyl-2 a picoline bromine salt.
With the 1-ethyl-2 picoline bromine salt 19.19g of system, 16.88g tosic acid and 40ml acetone join in the flask, and temperature of reaction is 75 ℃, condensing reflux.Reaction times 20h, reaction finishes, and removes moisture 70 ℃ of underpressure distillation, obtains tosic acid 1-ethyl-2-picoline salt ion liquid.With ether washing 4 times, 60 ℃ of underpressure distillation obtain high-purity tosic acid 1-ethyl-2-picoline salt ion liquid with ionic liquid.With 45 ℃, dry 10h obtains transparent ionic liquid 20.12g in vacuum drying oven.
With the 2.1g ionic liquid, 13.2g monomethyl succinate and 12g methyl alcohol are put into autoclave, feed nitrogen and make the pressure in the reactor drum rise to 1Mpa; Stir, Heating temperature is 100 ℃, and the reaction times is 10h; After reaction solution was cooled to room temperature, extraction obtained methyl-succinate, and transformation efficiency is 90%; Selectivity to remove unreacted reactant, is reused ion liquid abstraction greater than 96%.
The mass spectrum of resulting methyl-succinate is as shown in Figure 1, and nuclear magnetic spectrogram is as shown in Figure 2.
Embodiment 6: prepare methyl-succinate through 1-methyl-2-ethylpyridine tetrafluoroborate ion liquid catalysis monomethyl succinate
In round-bottomed flask, add 9.31g (0.1mol) 2-picoline and 10.9g (0.1mol) bromination ethane, Heating temperature to 80 ℃, reaction 24h; After question response stops fully; Be cooled to room temperature and separate out white crystal, put into loft drier, obtain white crystal 19.19g at 45 ℃ of dry 10h.White crystal is 1-ethyl-2 a picoline bromine salt.
With the 1-ethyl-2 picoline bromine salt 19.19g of system, 10.75g sodium tetrafluoroborate and 40ml acetone join in the flask, and temperature of reaction is 80 ℃, condensing reflux.Reaction times 20h, reaction finishes, and removes moisture 70 ℃ of underpressure distillation, obtains 1-methyl-2-ethylpyridine tetrafluoroborate ion liquid.With ether washing 4 times, 60 ℃ of underpressure distillation obtain high-purity 1-methyl-2-ethylpyridine tetrafluoroborate ion liquid with ionic liquid.With 45 ℃, dry 10h obtains transparent ionic liquid 19.48g in vacuum drying oven.
With the 2.1g ionic liquid, 13.2g monomethyl succinate and 12g methyl alcohol are put into autoclave, feed nitrogen and make the pressure in the reactor drum rise to 1Mpa; Stir, Heating temperature is 100 ℃, and the reaction times is 12h; After reaction solution was cooled to room temperature, extraction obtained methyl-succinate, and transformation efficiency is 92%; Selectivity to remove unreacted reactant, is reused ion liquid abstraction greater than 97%.
The mass spectrum of resulting methyl-succinate is as shown in Figure 1, and nuclear magnetic spectrogram is as shown in Figure 2.
Embodiment 7: prepare methyl-succinate through 1-ethyloic-3-ethylpyridine sulfate ion liquid catalyst monomethyl succinate
In round-bottomed flask, add 9.31g (0.1mol) 2-picoline and 10.9g (0.1mol) bromination ethane, Heating temperature to 80 ℃, reaction 24h; After question response stops fully; Be cooled to room temperature and separate out white crystal, put into loft drier, obtain white crystal 19.19g at 45 ℃ of dry 10h.White crystal is 1-ethyl-2 a picoline bromine salt.
With the 1-ethyl-2 picoline bromine salt 19.15g of system, 13.92g sodium sulfate and 40ml acetone join in the flask, and temperature of reaction is 75 ℃, condensing reflux.Reaction times 20h, reaction finishes, and removes moisture 60 ℃ of underpressure distillation, obtains 1-ethyloic-2-ethylpyridine sulfate ion liquid.With ether washing 4 times, 60 ℃ of underpressure distillation obtain high-purity 1-ethyloic-2-ethylpyridine sulfate ion liquid with ionic liquid.With 45 ℃, dry 10h obtains transparent ionic liquid 21.48g in vacuum drying oven.
With the 2.1g ionic liquid, 13.2g monomethyl succinate and 12g methyl alcohol are put into autoclave, feed nitrogen and make the pressure in the reactor drum rise to 0.1Mpa; Stir, Heating temperature is 120 ℃, and the reaction times is 10h; After reaction solution was cooled to room temperature, extraction obtained methyl-succinate, and transformation efficiency is 95%; Selectivity to remove unreacted reactant, is reused ion liquid abstraction greater than 99%.
The mass spectrum of resulting methyl-succinate is as shown in Figure 1, and nuclear magnetic spectrogram is as shown in Figure 2.
Embodiment 8: prepare methyl-succinate through 1 ethyloic-3-ethylpyridine carbonate ion liquid catalyst monomethyl succinate
In round-bottomed flask, add 9.31g (0.1mol) 2-picoline and 10.9g (0.1mol) bromination ethane, Heating temperature to 80 ℃, reaction 24h; After question response stops fully; Be cooled to room temperature and separate out white crystal, put into loft drier, obtain white crystal 19.19g at 45 ℃ of dry 10h.White crystal is 1-ethyl-2 a Methylimidazole bromine salt.
With the 1-ethyl-2 picoline bromine salt 19.19g of system, 10.39g yellow soda ash and 40ml acetone join in the flask, and temperature of reaction is 75 ℃, condensing reflux.Reaction times 20h, reaction finishes, and removes moisture 70 ℃ of underpressure distillation, obtains 1-ethyloic-2-ethylpyridine carbonate ion liquid.With ether washing 4 times, 60 ℃ of underpressure distillation obtain high-purity 1-ethyloic-2-ethylpyridine carbonate ion liquid with ionic liquid.With 45 ℃, dry 10h obtains transparent ionic liquid 18.42g in vacuum drying oven.
With the 2.1g ionic liquid, 13.2g monomethyl succinate and 12g methyl alcohol are put into autoclave, feed nitrogen and make the pressure in the reactor drum rise to 1Mpa; Stir, Heating temperature is 120 ℃, and the reaction times is 9h; After reaction solution was cooled to room temperature, extraction obtained methyl-succinate, and transformation efficiency is 89%; Selectivity to remove unreacted reactant, is reused ion liquid abstraction greater than 95%.
The mass spectrum of resulting methyl-succinate is as shown in Figure 1, and nuclear magnetic spectrogram is as shown in Figure 2.
Claims (9)
1. a method that makes monomethyl succinate and methanol esterification prepare methyl-succinate is characterized in that, uses monomethyl succinate and alcohol as reactant; As catalyzer, under nitrogen atmosphere, reaction pressure is 0.1-3Mpa with imidazoles, pyridines ionic liquid; Temperature of reaction is 90 ~ 150 ℃; Reaction times is 6-12h, and the mol ratio of ionic liquid, monomethyl succinate, alcohol is (0.1-2): 1: (1-10)
Wherein, described ionic-liquid catalyst is for to stablize, to be tart imidazoles or pyridines ionic liquid to water,
The cationic structure of said imidazoles is as follows:
Wherein, m is 0~15 integer, and n is 1~10 integer, and l is 0~15 integer; R
1Be C
1~C
10Alkyl or C
6~C
12Aryl, preferably, R
1Be C
1~C
6Alkyl or phenyl (Ph);
The cationic structure of said pyridines is as follows:
Wherein, m is 0~15 integer, and n is 1~10 integer, and l is 0~15 integer; R
1Be C
1~C
10Alkyl or C
6~C
12Aryl, preferred R
1Be C
1~C
6Alkyl or phenyl (Ph);
The anionicsite of said catalyzer is selected from CH
3PhSO
3 -, CF
3SO
3 -, HSO
4 -, SO
4 2-, HCOO
-, CH
3COO
-, CF
3COO
-, PO
4 3-, HPO
4 2-, H
2PO
4 -And N (CH
3SO
2)
2 -In;
Said preparation method of ionic liquid is following:
1) with imidazoles or pyridinium salt and equimolar acid: CH
3PhSO
3H, CF
3SO
3H, H
2SO
4, HCOOH, CH
3COOH, CF
3COOH, H
3PO
4, N (CH
3SO
2)
2H, HBF
4Or CF
3, stirred 12-24 hour at 50-120 ℃;
2) reaction finishes, and removes moisture 50-80 ℃ of underpressure distillation, obtains imidazoles or pyridinium salt ionic liquid;
3) ionic liquid is washed 1-4 time with ether;
4) 40-60 ℃ of underpressure distillation obtains high-purity imidazoles, pyridinium salt ionic liquid.
2. method according to claim 1, wherein, said ionic-liquid catalyst is tosic acid 1-ethyl-3-methylimidazole salt ionic liquid, and said reaction pressure is 1Mpa, and temperature of reaction is 100 ℃, and the reaction times is 10h.
3. method according to claim 1, wherein, said ionic-liquid catalyst is 1-ethyloic-3-ethyl imidazol(e) tetrafluoroborate ion liquid, and said reaction pressure is 1Mpa, and temperature of reaction is 100 ℃, and the reaction times is 12h.
4. method according to claim 1, wherein, said ionic-liquid catalyst is 1-ethyloic-3-ethyl imidazol(e) sulfate ion liquid, and said reaction pressure is 0.1Mpa, and temperature of reaction is 120 ℃, and the reaction times is 10h.
5. method according to claim 1, wherein, said ionic-liquid catalyst is 1-ethyloic-3-ethyl imidazol(e) carbonate ion liquid, and said reaction pressure is 1Mpa, and temperature of reaction is 120 ℃, and the reaction times is 9h.
6. method according to claim 1, wherein, said ionic-liquid catalyst is tosic acid 1-ethyl-2-picoline salt ion liquid, and said reaction pressure is 1Mpa, and temperature of reaction is 100 ℃, and the reaction times is 10h.
7. method according to claim 1, wherein, said ionic-liquid catalyst is 1-methyl-2-ethylpyridine tetrafluoroborate ion liquid, and said reaction pressure is 1Mpa, and temperature of reaction is 100 ℃, and the reaction times is 12h.
8. method according to claim 1, wherein, said ionic-liquid catalyst is 1-ethyloic-3-ethylpyridine sulfate ion liquid, and said reaction pressure is 0.1Mpa, and temperature of reaction is 120 ℃, and the reaction times is 10h.
9. method according to claim 1, wherein, said ionic-liquid catalyst is 1 ethyloic-3-ethylpyridine carbonate ion liquid, and said reaction pressure is 1Mpa, and temperature of reaction is 120 ℃, and the reaction times is 9h.
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CN112174876A (en) * | 2020-10-14 | 2021-01-05 | 江苏高科石化股份有限公司 | Preparation method and application of pyridine ionic liquid acidic catalyst |
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