CN118420464A - Preparation method of chloroacetate compound - Google Patents
Preparation method of chloroacetate compound Download PDFInfo
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- CN118420464A CN118420464A CN202410675043.3A CN202410675043A CN118420464A CN 118420464 A CN118420464 A CN 118420464A CN 202410675043 A CN202410675043 A CN 202410675043A CN 118420464 A CN118420464 A CN 118420464A
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- acid
- chloroacetate
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- ester
- catalyst
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- -1 chloroacetate compound Chemical class 0.000 title claims abstract description 31
- 229940089960 chloroacetate Drugs 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 21
- 229940106681 chloroacetic acid Drugs 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 239000003377 acid catalyst Substances 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000006555 catalytic reaction Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical group 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 239000011964 heteropoly acid Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000000704 physical effect Effects 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 15
- 150000002148 esters Chemical class 0.000 abstract description 11
- 239000000126 substance Substances 0.000 abstract description 7
- 125000002252 acyl group Chemical group 0.000 abstract description 4
- 238000007086 side reaction Methods 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000011084 recovery Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 8
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- HIIBHBNRMVLLKH-UHFFFAOYSA-N 2-(2-chloroacetyl)oxyethyl 2-chloroacetate Chemical compound ClCC(=O)OCCOC(=O)CCl HIIBHBNRMVLLKH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000010587 phase diagram Methods 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of a chloroacetate compound, and belongs to the technical field of chloroacetate compound preparation. Aiming at the problems of complex process, high energy consumption and cost and difficult recovery and utilization of alcohol substances in the synthesis process of chloroacetic acid esters, the invention directly carries out acyl exchange on chloroacetic acid and esters to obtain the chloroacetic acid esters. The method has the advantages of no water production in the reaction process, less side reaction in the reaction process, and simple post-treatment operation.
Description
Technical Field
The invention belongs to the technical field of chloroacetate compound preparation, and particularly relates to a preparation method of a chloroacetate compound.
Background
The chloroacetate compound is a widely applied chemical intermediate and solvent, and can be used as raw materials of dyes, medicines and fragrances. The industrial production of chloroacetic acid ester compounds is mainly obtained by esterification of chloroacetic acid and ester substances under the catalysis of sulfuric acid.
The problems with this process are: firstly, a large amount of water is generated in the reaction process, and in order to promote the forward movement of balance, water-carrying agents such as cyclohexane, benzene and the like are required to be added to form an azeotrope with the water, so that the process cost is increased; second, the post-reaction treatment operation is complicated. For example, in a method for preparing ethyl chloroacetate, in patent CN116870808, a mixture of esterified ethyl chloroacetate and water flows into an azeotropic tower, cyclohexane with water agent is added into the azeotropic tower, the water agent, water and ethanol form a ternary azeotrope, the azeotrope is divided into a water phase and a water agent phase in a layering tank under the action of a condenser, the water agent flows back into the azeotropic tower along a return pipe to continuously take out water, the water phase is discharged from a drain pipe, and the ethanol in the water phase is distilled out again through a rectifying tower and then is recycled. The whole separation process increases the energy consumption and cost of the process, and the ethanol in the water phase is not easy to separate from the water, so that if the ethanol is directly returned to the reaction device, the water can further inhibit the reaction. In the aftertreatment of the patent CN 113004143A, the obtained crude ethyl chloroacetate is subjected to oil-water separation to obtain crude ester, the crude ester is rectified to obtain chloroacetic acid, ethyl ester and ethanol liquid, and the ethanol liquid is recycled into an esterification reaction kettle. The separation process has the defects of high energy consumption, high cost, difficult recovery and utilization of alcohol substances and the like.
Disclosure of Invention
Aiming at the problems in the synthesis process of chloroacetic acid esters, the method directly carries out acyl exchange on chloroacetic acid and esters to obtain the chloroacetic acid esters. The method has the advantages of no water production in the reaction process, less side reaction in the reaction process, and simple post-treatment operation.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
The chloroacetic acid, the ester compound and the catalyst are fully mixed to prepare a catalytic reaction system for reaction, and reaction products are separated after the reaction is completed to obtain the chloroacetic acid ester compound.
Further, the ester compound refers to a carboxylic acid ester containing one or more ester groups.
Further, the groups connected at two ends of the ester group in the ester compound are alkyl, cycloalkyl, heteroaryl, naphthyl, alkenyl, alkynyl or phenyl.
Further, the alkyl group comprises methyl, ethyl, propyl, isopropyl, butyl; the cycloalkyl comprises cyclopropyl, 2-methylcyclopropyl, cyclobutyl and cyclopentyl; the heteroaryl group includes furyl and thienyl; the alkenyl group comprises ethenyl, propenyl and butenyl; the alkynyl group includes ethynyl, propynyl and butynyl. These groups may in turn be attached to one or more of fluorine, chlorine, bromine, alkyl, alkoxy, nitro, trifluoromethyl or cyano groups, the attached fluorine, chlorine, bromine, alkyl, alkoxy, nitro, trifluoromethyl or cyano groups having substantially no effect on the reaction but may affect the activity of the esters.
Further, the catalyst is an organic acid catalyst or an inorganic acid catalyst. The reaction may be catalyzed by essentially any acid catalyst.
Further, the organic acid catalyst is one or a mixture of more of methane sulfonic acid, benzene sulfonic acid, trifluoromethane sulfonic acid, p-toluene sulfonic acid, dodecylbenzene sulfonic acid and acid resin; the inorganic acid catalyst is one or a mixture of more of sulfuric acid, phosphoric acid, hydrochloric acid, zinc chloride, aluminum sulfate, an acidic molecular sieve and heteropolyacid.
Further, the molar ratio of the chloroacetic acid to the ester compound is 1-10: 1, if the ratio is lower than the range, the reaction of the ester substance is incomplete, and if the ratio is higher than the range, the chloroacetic acid raw material is wasted; the mass ratio of the catalyst to the ester compound is 0.01-1: 1. if the catalyst amount is too small, the conversion rate of the ester is low, and if the catalyst amount is too large, the cost is increased.
Further, the reaction temperature of the prepared catalytic reaction system is 80-200 ℃ and the reaction time is 1-10 hours. The chloroacetic acid and the ester substances do not react at the reaction temperature which is too low, and side reactions are easy to generate; the reaction time is too short, the ester substance can not be completely reacted, the reaction time is too long, and the reaction economy is poor.
Further, separating the reaction product after the reaction is completed means that the reaction system is distilled, extracted or recrystallized according to the physical properties of the reaction product.
Compared with the prior art, the invention has the following advantages:
1. Firstly, chloroacetic acid and esters undergo an acyl exchange reaction to obtain chloroacetate compounds and carboxylic acid by a one-step method, and byproducts are few.
2. The chloroacetate compound can be obtained without using a complicated dehydration process.
3. The method has the advantages of high efficiency, green, economy and the like, and the molar yield of chloroacetate is more than 80%.
Drawings
FIG. 1 is a gas chromatogram of example 1 (peaks from left to right for reactant ethyl acetate, product acetic acid, internal standard 1, 4-dioxane, solvent toluene, target product ethyl chloroacetate, and reactant chloroacetic acid).
FIG. 2 is 1 H NMR spectrum of ethyl chloroacetate of example 1.
FIG. 3 is a 13 C NMR spectrum of ethyl chloroacetate of example 1.
FIG. 4 is a 1 H NMR spectrum of ethylene glycol dichloroacetate in example 2.
FIG. 5 is a 13 C NMR spectrum of ethylene glycol dichloroacetate in example 2.
Detailed Description
For an appreciation of the invention, we will describe it in full detail. However, the present invention has a variety of implementations and is not limited to the specific examples listed herein. These examples are presented in order to enhance a thorough understanding of the present disclosure.
Example 1
Mixing 1.0g of ethyl acetate, 3.2g of chloroacetic acid and 0.2g of methane sulfonic acid, reacting for 1h at 100 ℃, distilling the liquid after the reaction is completed, collecting a first section of fraction to obtain acetic acid, collecting a second section of fraction to obtain ethyl chloroacetate, and obtaining the rest of the bottom of the flask, namely the catalyst and the chloroacetic acid, wherein the conversion rate of the ethyl acetate is 99% and the molar yield of the ethyl chloroacetate is 98% through gas phase analysis.
Example 2
1.0G of ethylene glycol diacetate, 3.8g of chloroacetic acid and 0.3g of potassium bisulfate are mixed, reacted in a reaction kettle at 190 ℃ for 6.5 hours, after the reaction is completed, the liquid is poured into a flask from the kettle, water is added into the liquid, the water phase is chloroacetic acid, acetic acid and potassium bisulfate, the organic phase is a small amount of unreacted ethylene glycol diacetate and ethylene glycol diacetate, ethanol is used for recrystallization, and the ethylene glycol diacetate is obtained, and through gas phase analysis, the conversion rate of the ethylene glycol diacetate is 88%, and the molar yield of the ethylene glycol diacetate is 80%.
The following examples are similar to the procedure of example 1 or example 2, and the different materials or conditions involved are presented in tabular data format.
The gas phase diagram after the ethyl chloroacetate reaction in the example 1 is completed is shown in fig. 1, the nuclear magnetic resonance hydrogen spectrum of the ethyl chloroacetate product is shown in fig. 2, and the nuclear magnetic resonance carbon spectrum is shown in fig. 3; the nuclear magnetic resonance hydrogen spectrum of ethylene glycol dichloroacetate product in example 2 is shown in fig. 4, and the nuclear magnetic resonance carbon spectrum is shown in fig. 5.
In summary, it can be seen from examples 14 and 15 that the results obtained are poor when the temperature is outside the range of 80 to 200 ℃. At a temperature of 70 ℃, the acyl exchange reaction hardly occurs; at a temperature of 210 ℃, side reactions occur, resulting in reduced yields of chloroacetate.
What is not described in detail in the present specification belongs to the prior art known to those skilled in the art. While the foregoing describes illustrative embodiments of the present invention to facilitate an understanding of the present invention by those skilled in the art, it should be understood that the present invention is not limited to the scope of the embodiments, but is to be construed as protected by the accompanying claims insofar as various changes are within the spirit and scope of the present invention as defined and defined by the appended claims.
Claims (9)
1. A preparation method of chloroacetate compounds is characterized in that: and fully mixing chloroacetic acid, an ester compound and a catalyst to prepare a catalytic reaction system for reaction, and separating a reaction product after the reaction is finished to obtain the chloroacetic acid ester compound.
2. The method for preparing a chloroacetate compound according to claim 1, wherein: the ester compound refers to a carboxylic acid ester containing one or more ester groups.
3. The method for preparing a chloroacetate compound according to claim 1, wherein:
The groups connected at the two ends of the ester group in the ester compound are alkyl, cycloalkyl, heteroaryl, naphthyl, alkenyl, alkynyl or phenyl.
4. The method for producing a chloroacetate compound according to claim 3, wherein: the alkyl group comprises methyl, ethyl, propyl, isopropyl and butyl; the cycloalkyl comprises cyclopropyl, 2-methylcyclopropyl, cyclobutyl and cyclopentyl; the heteroaryl group includes furyl and thienyl; the alkenyl group comprises ethenyl, propenyl and butenyl; the alkynyl group includes ethynyl, propynyl and butynyl.
5. The method for preparing a chloroacetate compound according to claim 1, wherein: the catalyst is an organic acid catalyst or an inorganic acid catalyst.
6. The method for preparing chloroacetate compound according to claim 5, wherein: the organic acid catalyst is one or a mixture of more of methane sulfonic acid, benzenesulfonic acid, trifluoromethane sulfonic acid, p-toluenesulfonic acid, dodecylbenzene sulfonic acid and acid resin; the inorganic acid catalyst is one or a mixture of more of sulfuric acid, phosphoric acid, hydrochloric acid, zinc chloride, aluminum sulfate, an acidic molecular sieve and heteropolyacid.
7. The method for preparing a chloroacetate compound according to claim 1, wherein: the molar ratio of the chloroacetic acid to the ester compound is 1-10: 1, the mass ratio of the catalyst to the ester compound is 0.01-1: 1.
8. The method for preparing a chloroacetate compound according to claim 1, wherein: the reaction temperature of the prepared catalytic reaction system is 80-200 ℃ and the reaction time is 1-10 hours.
9. The method for preparing a chloroacetate compound according to claim 1, wherein: separating the reaction product after the reaction is finished refers to distilling, extracting or recrystallizing the reaction system according to the physical property of the reaction product.
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| CN202410675043.3A CN118420464A (en) | 2024-05-29 | 2024-05-29 | Preparation method of chloroacetate compound |
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| CN202410675043.3A CN118420464A (en) | 2024-05-29 | 2024-05-29 | Preparation method of chloroacetate compound |
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| CN202410675043.3A Pending CN118420464A (en) | 2024-05-29 | 2024-05-29 | Preparation method of chloroacetate compound |
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- 2024-05-29 CN CN202410675043.3A patent/CN118420464A/en active Pending
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