CN105585485A - Production method for low-carbon acetate - Google Patents
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Abstract
The invention relates to a production method for low-carbon acetate. In the method, a catalyst based on an ionic liquid is employed to catalyze low-carbon olefin and acetic acid to be directly subjected to an additive polymerization reaction to produce the low-carbon acetate, wherein the cation in the ionic liquid is represented as the following structure formula, and the anions include: HSO4<->, CF3SO3<->, NTf2<->, H2PO4<->, PW12O40<3->, p-CH3-(C6H4)SO3<->, PMo12O40<3->, H2PW12O40<->, X<->, PF6<-> or SbF6<->. The ionic liquid catalyst can convert mixed butene into sec-butyl acetate at high selectivity. The catalyst is stable in structure and is easy to separate. The production method is simple in follow-up operations, is less in side products, is low in corrosion and is low in environment pollution.
Description
Technical field
The present invention relates to a kind of production method of acetic acid low-carbon ester, relate in particular to a kind of ionic liquid-catalyzed acid-alkene direct esterification and produceThe method of acetic acid low-carbon ester.
Background technology
Acetic acid low-carbon ester is a kind of widely used Organic Ingredients, has special meaning in industrial production. For example ethyl acetateOne of synthetic perfume of large usage quantity in flavoring essence, in a large number for allocating the odor type foods such as banana, pears, peach, pineapple, grapeWith essence; Also be the low-toxic solvent of industrial use, as celluloid, ethyl cellulose, cellulose acetate and neopreneThe quick-drying solvent of rubber etc., the cleaning agent of textile industry and the extractant of natural perfume material. Sec-butyl acetate is because having dissolubilityCan be strong, evaporation rate is moderate, toxicity is little and the residual advantage such as few, can dissolve various kinds of resin and organic matter, as a kind of greenEnvironment-friendly type solvent, is widely used in the industries such as coating, ink, medicine, agricultural chemicals, production of resins diluent.
The production technology of acetic acid low-carbon ester mainly comprises sour-ol dehydration esterification process and acid-alkene addition esterification process. Acid alcohol dehydration esterification processMainly refer to that low-carbon alcohols and acetic acid or acid anhydrides react, thereby take off the reaction of a hydrone formation ester. Acid-alkene addition esterificationMethod mainly refers to that the two ends of low-carbon alkene unsaturated double-bond respectively add respectively one-CH3COO and-thereby H generates the reaction of ester. Acid-Dehydration of alcohols esterification process mature production technology, but exist many drawbacks that are difficult to overcome,, pollution high such as cost weighs, equipmentThe water of production equivalent accessory substance in the low and course of reaction of seriously corroded, productive rate, separation of products difficulty etc. By contrast, acid-Alkene addition esterification reaction process no coupling product generates, and Atom economy is good, has that adaptability to raw material is strong, cost is low, environment is friendlyThe advantages such as good, product is easily separated.
The catalyst that is usually used in acid-alkene addition esterification mainly comprises two kinds of solid acid and liquid acid. Solid acid catalyst mainly wrapsDraw together cationic ion-exchange resin (Amberlyst-15 and chloride group modified DLC-116 heatproof cationic ion-exchange resin), assorted manyAcid and zeolite etc. In general corrosivity is low for solid acid catalyst, environmental friendliness but often exist selectively not high, inactivationThe shortcoming such as fast. Liquid acid catalyst mainly comprises the concentrated sulfuric acid, phosphoric acid, BF3Deng. Common liq acid catalyst is because existing equipmentThe serial negative effects such as seriously corroded, environmental pollution are large, operational hazards are abandoned gradually. Novel acid ionic liquid synthetic andApplication is the acid catalyzed representative studies direction of current liquid.
Ionic liquid is that a class forms emerging eco-friendly fluent material by zwitterion completely, has unique structure and propertyMatter. The appearance of ionic liquid has greatly changed the cognition of region of chemistry, provides new thinking and opportunity for starting clean new technology,And highlighted advantage in various fields, become one of chief motivation of chemical, process change. Wherein acid fromSub-liquid is an important branch of ionic liquid research.
Compared with traditional acid catalyst, ionic liquid has unique advantage during as catalyst: compared with liquid acid, from
Sub-liquid does not have volatility; With solid acid ratio, acidic ion liquid has again better mobility, more peracidity position is closeDegree and the acid strength more uniformly that distributes; The zwitterion structure modifiability harmonizing yinyang that the most important thing is acidic ion liquid fromSub-concertedness, that is to say that can and modify zwitterion by modulation forms the property that changes its dissolubility, density, viscosity, acidMatter and sour intensity etc., and then improve the performance that recycles of the activity of catalyst, selective and catalyst system and catalyzing. Acid in recent yearsIn property ionic liquid inoic acid catalytic reaction, as alkylated reaction, acyl group, ester exchange, Manny alkene reaction etc., representGood catalytic effect, and represented its huge industrial prospect and development potentiality.
At present, the acidic ion liquid of bibliographical information is also having a lot of application aspect sour-ol esterification. For example Davis in 2002Deng having synthesized the acidic ion liquid (J.Am.Chem.Soc.2002,124,5962) of cation containing sulfonic acid group, its structure asShown in table 1 (a), for catalysis acid-ol esterification and obtained good catalytic effect; The same year, Dubreuil etc. was syntheticAnion is containing acid ionic liquid (as CatalysisCommunications, 2002,3,185), and its structure is as table 1 (b) instituteShow, can be used as catalyst esterification; 2009 Nian Wang armies etc. have synthesized zwitterion all containing acid heteropoly acid ionic liquidBody (Angew.Chem., 2009,121,174), its structure, as shown in table 1 (c), can be used for catalysis acid-ol esterification etc.Deng. But the report of acidic ion liquid aspect acid-alkene addition esterification is also fewer.
The kind of table 1 ionic liquid
2004 Deng (JournalofMolecularCatalysisA, Chemical, 2004,212,71) etc. will contain cloudy fromSon is that sulfonic acid functional group's ionic liquid is the addition esterification of catalyst acid-alkene, under certain temperature, pressure condition,Can obtain higher olefin conversion and primary product selective. CN1600773A discloses one and has closed from alkene and organic acidBecome the method for ester, adopt end bonding to have sulfonic group (SO3H) alkyl pyridine or 1,3-dialkylimidazolium cation and anion structureThe ionic liquid that is liquefaction under the room temperature becoming is reaction medium and catalyst, under 0.1 to 2.0MPa, and at 50 to 150 DEG C,React and produce carboxylate in 1 to 8 hour, it selectively can reach 100%, and acetic acid conversion ratio is 89%.
But, use other acidic ion liquids to carry out the research of catalysis acid-alkene addition esterification, but rarely have report. The present inventionRelated catalyst utilizes the presence of acidic ionic liquid catalyst synthesis of acetic acid low-carbon ester of other structures, not only has catalyst structure steadyDetermine the advantages such as easily separated, subsequent operation is simple, accessory substance is few, corrosivity is low, environmental pollution is little, and the warp of synthetic catalystJi cost is low, by being expected to develop a kind of production aspect of novel acetic acid low-carbon ester, promotes its process of industrialization.
Summary of the invention
Based on current present Research, the object of the present invention is to provide a kind of production method of acetic acid low-carbon ester, its principle isTaking acidic ion liquid as catalyst, the direct addition esterification of catalysis low-carbon alkene synthesis of acetic acid low-carbon ester. Related ionic liquidCatalyst can be converted into sec-butyl acetate by high selectivity catalytic mixing butylene, and catalyst structure is stablized easily separated, subsequent operationSimply, accessory substance is few, corrosivity is low, environmental pollution is little.
For reaching this object, the present invention by the following technical solutions:
A production method for acetic acid low-carbon ester, adopts the catalyst based on ionic liquid, and catalysis low-carbon alkene and acetic acid directly addBecome esterification, the cation of described ionic liquid has
Structure, wherein Rf＝-CnH2n+1、(CF2)nCF3；nBeing 0 to 8 integer, for example, is 1,2,3,4,5,6,7,8, is preferably 0 to 5 integer; Anion is HSO4 -、CF3SO3 -、NTf2 -、H2PO4 -、PW12O40 3-、p-CH3-(C6H4)SO3 -、PMo12O40 3-、H2PW12O40 -、X-、PF6 -Or SbF6 -. For example ionic liquid can be
Deng.
Production method of the present invention, the described catalyst based on ionic liquid can be only ionic liquid, can be also ionLiquid with there is the inorganic salts compound use of lewis acidity, not only etching apparatus not of compound use, environmentally friendly, also haveThan the higher selectivity of product of pure ionic-liquid catalyst and product yield and separating property.
Catalyst of the present invention is acidic ion liquid, by ionic liquid zwitterion structure, introduce acidic-group orIn ionic liquid, add the low-carbon alkene addition esterification catalyst that the metal organic salt with Lewis acidity is prepared suitable acidity. ThisIonic-liquid catalyst in invention can be effectively by mixed butene (comprising 1-butylene, (just, anti-)-2-butylene and isobutene)Highly selective is converted into sec-butyl acetate.
Alkene esterification refers to that under the effect of acidic catalyst, two keys of alkene are opened taking alkene and carboxylic acid as raw material,In-COOH-H and-thereby the two ends that COO-is added in respectively the two keys of fracture form the structure (reaction mechanism is as follows) of ester.Compared with traditional production technology, the scheme taking alkene as raw material has better Atom economy, has avoided the life of water byproductBecome, this just can impel molecular balance to move right, and improves reaction-ure conversion-age, and reaction finish after without consideration waste waterRecycling problem; In addition, can adopt new catalyst, not only can improve the selective and separating property of product, simultaneouslyAvoid again the corrosion to consersion unit.
Preferably, described inorganic salts be Bismuth triflate, Ytterbiumtriflate, TFMS scandium, TFMS zirconium,One kind or two or more mixture in stannic chloride and zinc chloride, and be not limited to this.
Preferably, the addition of inorganic salts is 1wt%～30wt% described in the total amount based on catalyst, be for example 3wt%, 5wt%,8wt%, 12wt%, 16wt%, 20wt%, 25wt%, 18wt% etc.
As optimal technical scheme, production method of the present invention, described alkene is containing 1 in the alkene of 2-5 carbon atomPlant or mixture of more than two kinds, be preferably the mixture of butylene.
As optimal technical scheme, production method of the present invention, the mol ratio of described acetic acid and ionic liquid is 1:1-1:4,Be for example 1:1.5,1:2.2,1:3.1,1:3.7 etc., be preferably 1:2.
As optimal technical scheme, production method of the present invention, the condition of catalytic reaction is: reaction pressure is0.5～5.0MPa, for example, be 0.7MPa, 1.2MPa, 2.0MPa, 2.5MPa, 4MPa, 4.6MPa etc., reaction temperature50～200 DEG C is for example 60 DEG C, 75 DEG C, 90 DEG C, 120 DEG C, 160 DEG C, 185 DEG C etc., more than reaction time 30min, and exampleAs be 50min, 1.5h, 3h, 12h, 20h, 45h, 60h, 80h etc.
Preferably, the condition of catalytic reaction is: reaction pressure 1.0～3.0MPa, and 80～150 DEG C of reaction temperatures, the reaction time is1-50h, is preferably 3-10h.
As preferably, V in catalytic reactionAcetic acid：VContaining olefin feedstock gas=1:1-5 (volume ratio), is preferably 1:3, wherein containing olefin feedstockOlefin(e) centent in gas more than 5wt%, preferably 5-60wt%, further preferred 10-35wt%.
Ionic-liquid catalyst provided by the invention can be converted into sec-butyl acetate by mixed butene highly selective, has as followsBenefit: (1) catalyst structure is stable and easily separated, and subsequent operation is simple, and ionic liquid after separating is also reusableAnd keep greater activity; (2) accessory substance of catalytic reaction is few, environmental pollution is little, little to equipment corrosion, be conducive to promote secondAdvance and the competitiveness of the low ester production method of acid.
It is the catalyst of low-carbon alkene direct esterification that the present invention adopts acidic ion liquid, compares with concentrated sulfuric acid catalyst, can obtainHigher butene conversion and sec-butyl acetate selective, acidic ion liquid environmental friendliness does not have corrosivity to equipment simultaneously,Advance and the competitiveness of production method of the present invention are improved.
The present invention is described in more detail below. But following example is only simple and easy example of the present invention, does not represent or limitsThe scope of the present invention processed, protection scope of the present invention is as the criterion with claims.
Detailed description of the invention
Further illustrate technical scheme of the present invention below by detailed description of the invention. For the present invention is described better, be convenient to reasonSeparate technical scheme of the present invention, typical but non-limiting embodiment of the present invention is as follows.
The inorganic salts with lewis acidity described in the present invention are commercially available prod. For example Bismuth triflate, fluoroform sulphurAcid ytterbium; There are lark waffle learn a skill peculiar your Science and Technology Ltd. of Co., Ltd, Shenyang, Shanghai in TFMS scandium sales companySi Ying Chemical Industry Science Co., Ltd etc. The supplier such as stannic chloride, zinc chloride has Chemical Reagent Co., Ltd., Sinopharm Group, Beijing largeTian Feng opens up chemical technology Co., Ltd, Beijing Heng Yezhongyuan Chemical Co., Ltd. etc.
The present invention's ionic liquid used synthetic, employing be technology known in those skilled in the art, this present invention is not doneDescribe in detail.
Low-carbon alkene and acetic acid are at ionic-liquid catalyst or ionic liquid and have the compound effect of the inorganic salts of lewis acidityUnder, low-carbon alkene and acetic acid carry out addition reaction and generate acetic acid low-carbon ester in mechanically stirred reactor. The operating pressure of reaction is50～200 DEG C of 0.5～5.0MPa, reaction temperatures, sour alkene mol ratio 0.4～20, more than reaction 30min. Preferred processing condition is:80～150 DEG C of reaction pressure 1.0～3MPa, reaction temperatures, VAcetic acid：VContaining olefin feedstock gas=1:1-5. React complete, product and catalystAutomatically divide and be separated or use organic solvent simple extraction, can realize separating of ionic-liquid catalyst and product. This reaction canIntermittently and continuously to move. Described low-carbon alkene is containing any one or several mixtures in 2-5 carbon atom alkene,The preferably mixture of butylene.
Comparative example
Adopt the concentrated sulfuric acid as catalyst, catalytic mixing butylene-acetic acid addition esterification. In reactor, add appropriate catalysisAgent, acetic acid 5ml, tightens kettle cover, forms confined space. Start agitator, rotating speed 1000r/min. Open unstripped gas sampling pump,It is 500ml/h that sample rate is set, and adds the liquefied gas 18ml containing alkene 28.6wt%. It is 90 DEG C that recycle oil bath temperature is set,When question response still thermometer registration reaches set temperature, start timing, reaction time 4h. Reaction time arrives after 4h, stopsStir and heating, question response still continues to leave standstill 15 minutes after naturally cooling to room temperature. Then collect tail gas with airbag, ensure instituteThere is gas collection in an airbag. Liquid part is the cyclic washing of process clear water, ether, clear water successively, finally by ether phaseSealing is preserved. Conversion ratio, total olefin conversion ratio and the sec-butyl acetate of each alkene composition selectively as shown in table 2.
Table 2
As can be seen from the above table, when taking the concentrated sulfuric acid as catalyst, various conversion of olefines rates and total olefin conversion ratio all compareHeight, but sec-butyl acetate is selectively poor.
Embodiment 1
With acidic ion liquid [BSN222][H2PW12O40] be the catalyst of acetic acid-butylene addition esterification. Wherein BSN222Be threeEthyl-butyl sulfonic acid ammonium salt. In reactor, add [the BSN of 0.5g222][H2PW12O40], acetic acid 5ml, tightens kettle cover, shapeBecome confined space. Start agitator, rotating speed 1000r/min. Open unstripped gas sampling pump, it is 500ml/h that sample rate is set,Add the liquefied gas 15ml containing alkene 28.6wt%. It is 90 DEG C that recycle oil bath temperature is set, and question response still thermometer registration reaches establishesWhile putting temperature, start timing, reaction time 4h. Reaction time arrives after 4h, stops stirring and heating question response still natureAfter being cooled to room temperature, continue to leave standstill 15 minutes. Then collect tail gas with airbag, ensure that all gas is collected in an airbag.Liquid part successively, through the cyclic washing of clear water, ether, clear water, finally seals preservation by ether mutually. Turning of each alkene compositionRate, total olefin conversion ratio and sec-butyl acetate selectively as shown in table 3.
Table 3
As can be seen from Table 3, use [BSN222][H2PW12O40] catalyst, sec-butyl acetate selectively can reach 93.2%Selective while making catalyst higher than the concentrated sulfuric acid far away.
Embodiment 2
With acidic ion liquid [Ph3PSO3H][HSO4] be the catalyst of acetic acid-butylene addition esterification. The amount of catalyst is 3.62G. Reactions steps is as embodiment 1. Conversion ratio, total olefin conversion ratio and the sec-butyl acetate of each alkene composition selective asShown in table 4.
Table 4
Embodiment 3
With acidic ion liquid [BSN222]3[PW12O40] be the catalyst of acetic acid-butylene addition esterification. The amount of catalyst is[BSN222]3[PW12O40] 0.5g. Reactions steps is as embodiment 1. The conversion ratio of each alkene composition, total olefin conversion ratio andSec-butyl acetate selectively as shown in table 5.
Table 5
Embodiment 4
With combination of acidic ionic liquid [Bmim] [HSO4]+Bi(CF3SO3)3For the catalyst of acetic acid-butylene addition esterification, whereinBmim is 1-butyl-3-methylimidazole cation. In reactor, add [Bmim] [HSO of 10g4] and 0.3gBi(CF3SO3)3, after stirring, add acetic acid 5ml, tighten kettle cover, form confined space. Start agitator, rotating speed1000r/min. Open unstripped gas sampling pump, it is 500ml/h that sample rate is set, and adds the liquefied gas 15ml containing alkene 28.6wt%.It is 90 DEG C that recycle oil bath temperature is set, and when question response still thermometer registration reaches set temperature, starts timing, reaction time 4h.Reaction time arrives after 4h, stops stirring and heating, and question response still continues to leave standstill 15 minutes after naturally cooling to room temperature. ThenCollect tail gas with airbag, ensure that all gas is collected in an airbag. Liquid part is successively through clear water, ether, clear waterCyclic washing, finally seals preservation mutually by ether. Conversion ratio, total olefin conversion ratio and the sec-butyl acetate of each alkene compositionSelectively as shown in table 6.
Table 6
Embodiment 5
With combination of acidic ionic liquid [Bmim] [HSO4]+Yb(CF3SO3)3For the catalyst of acetic acid-butylene addition esterification.The amount of catalyst is [Bmim] [HSO4] 10g and Bi (CF3SO3)30.3g. Reactions steps is as embodiment tri-. Each alkene becomesPoint conversion ratio, total olefin conversion ratio and sec-butyl acetate selectively as shown in table 7.
Table 7
Embodiment 6
With combination of acidic ionic liquid [Bmim] [PF6]+Yb(CF3SO3)3For the catalyst of acetic acid-butylene addition esterification. CatalystAmount be [Bmim] [PF6] 11g and Yb (CF3SO3)30.4g. Reactions steps is as embodiment tri-. The conversion ratio of each alkene composition,Total olefin conversion ratio and sec-butyl acetate selectively as shown in table 8.
Table 8
Embodiment 7
With combination of acidic ionic liquid [Bmim] [SbF6]+Yb(CF3SO3)3For the catalyst of acetic acid-butylene addition esterification. CatalysisThe amount of agent is [Bmim] [SbF6] 15g and Yb (CF3SO3)30.3g. Reactions steps is as embodiment tri-. The conversion of each alkene compositionRate, total olefin conversion ratio and sec-butyl acetate selectively as shown in table 9.
Table 9
Can find out ionic liquid and the direct addition esterification of inorganic salts compound use catalysis low-carbon alkene production second from table 6 to table 9The reaction of acid low-carbon ester has very high selective, can be up to 100%.
Embodiment 8: the repeat performance of ionic liquid
To catalyst [Ph3PSO3H][HSO4] carry out cycle performance test, found that [Ph3PSO3H][HSO4] catalyst useAfter 8 times, its catalytic conversion does not decline substantially, and the catalyst that visible the present invention makes can repeatedly recycle, its serviceabilityAs catalytic conversion remains unchanged substantially. The cycle performance of this catalyst is as shown in table 10.
Table 10
Selective and conversion ratio computational methods are as follows:
(1) calculating of conversion ratio
Occurring when esterification, to only have alkene to react in unstripped gas, and gas iso-butane in unstripped gas and normal butane are alsoDo not change, before and after reaction, the gross mass of iso-butane does not change, therefore can be taking normal butane as the various alkene of criterion calculationThe conversion ratio of hydrocarbon. Olefin conversion formula is:
Wherein, β1---olefin(e) centent in unstripped gas before reaction, wt%;
β2---olefin(e) centent in gas after reaction, wt%;
α1---iso-butane content in unstripped gas before reaction, wt%;
α2---iso-butane content in gas after reaction, wt%;
The gross mass of m---the unstripped gas that adds before reaction, g;
---conversion ratio, %.
Note: this formula is all suitable for every kind of alkene and alkene total amount.
(2) optionally calculate
Taking sec-butyl acetate as example, calculate that it is selective,
Wherein, fm,i---i component relative correction factor; Ai---the peak area of i component;
fm,j---j component relative correction factor; Aj---the peak area of j component;
ωi---the content of i component in mixture
Applicant's statement, above embodiment is only unrestricted in order to technical scheme of the present invention to be described, although with reference to better enforcementExample has been described in detail the present invention, those skilled in the art will appreciate that and can enter technical scheme of the present inventionRow is revised or is equal to replacement, and does not depart from the spirit and scope of technical solution of the present invention, and it all should be encompassed in power of the present inventionIn profit claimed range.
More than describe the preferred embodiment of the present invention in detail, still, the present invention is not limited to concrete in above-mentioned embodimentDetails, within the scope of technical conceive of the present invention, can carry out multiple simple variant to technical scheme of the present invention, and these are simpleModification all belongs to protection scope of the present invention.
It should be noted that in addition, each the concrete technical characterictic described in above-mentioned detailed description of the invention, in reconcilable feelingsUnder condition, can combine by any suitable mode, for fear of unnecessary repetition, the present invention is to various possible groupsClose mode explanation no longer separately.
In addition, between various embodiment of the present invention, also can be combined, as long as it is without prejudice to of the present inventionThought, it should be considered as content disclosed in this invention equally.
Claims (9)
1. a production method for acetic acid low-carbon ester, adopts the catalyst based on ionic liquid, catalysis low-carbon alkene and acetic acidDirectly addition esterification, is characterized in that, the cation of described ionic liquid has
Structure, wherein Rf＝-CnH2n+1、(CF2)nCF3；nIt is 0 to 8 integer; Anion is HSO4 -、CF3SO3 -、NTf2 -、H2PO4 -、PW12O40 3-、p-CH3-(C6H4)SO3 -、PMo12O40 3-、H2PW12O40 -、X-、PF6 -Or SbF6 -。
2. production method as claimed in claim 1, is characterized in that, the described catalyst based on ionic liquid is only ionLiquid or be ionic liquid and inorganic salts compound with lewis acidity.
3. production method as claimed in claim 2, is characterized in that, described inorganic salts are Bismuth triflate, fluoroformOne kind or two or more mixture in sulfonic acid ytterbium, TFMS scandium, TFMS zirconium, stannic chloride and zinc chloride.
4. production method as claimed in claim 2 or claim 3, is characterized in that, inorganic salts described in the total amount based on catalystAddition is 1～30wt%.
5. the production method as described in claim 1-3 any one, is characterized in that, described low-carbon alkene is for former containing 2-5 carbonOne kind or two or more mixture in the alkene of son.
6. the production method as described in claim 1-3 any one, is characterized in that, described acetic acid and ionic liquid moleThan being 1:1-1:4.
7. production method as claimed in claim 6, is characterized in that, the mol ratio of described acetic acid and ionic liquid is 1:2.
8. the production method as described in any one in claim 1-3 or 7, is characterized in that, catalytic reaction pressure is0.1～5.0MPa, 50～200 DEG C of reaction temperatures, more than reaction time 30min.
9. production method as claimed in claim 8, is characterized in that, catalytic reaction pressure 1.0～3.0MPa, reaction temperature80～150 DEG C, the reaction time is 1-50h.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109438290A (en) * | 2018-12-05 | 2019-03-08 | 辽宁科技学院 | The method of the preparation and its catalytic synthesis of chloroacetic acid ester of novel temperature-sensitive ionic liquid |
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| CN1600773A (en) * | 2003-09-25 | 2005-03-30 | 中国科学院兰州化学物理研究所 | Method for esterifying olefin and organic acid |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109438290A (en) * | 2018-12-05 | 2019-03-08 | 辽宁科技学院 | The method of the preparation and its catalytic synthesis of chloroacetic acid ester of novel temperature-sensitive ionic liquid |
| CN109438290B (en) * | 2018-12-05 | 2021-06-11 | 辽宁科技学院 | Preparation of novel temperature-sensitive ionic liquid and method for catalytically synthesizing chloroacetate by using same |
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Application publication date: 20160518 |