CN111039783A - Method for synthesizing ethyl laurate by taking eutectic solvent based on benzyltrimethylammonium chloride as catalyst - Google Patents
Method for synthesizing ethyl laurate by taking eutectic solvent based on benzyltrimethylammonium chloride as catalyst Download PDFInfo
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- CN111039783A CN111039783A CN201911331547.9A CN201911331547A CN111039783A CN 111039783 A CN111039783 A CN 111039783A CN 201911331547 A CN201911331547 A CN 201911331547A CN 111039783 A CN111039783 A CN 111039783A
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- catalyst
- bac
- des
- ammonium chloride
- trimethyl ammonium
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- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 239000003054 catalyst Substances 0.000 title claims abstract description 31
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 title claims abstract description 19
- 230000005496 eutectics Effects 0.000 title claims abstract description 14
- 239000002904 solvent Substances 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 11
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 35
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims abstract description 28
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000005639 Lauric acid Substances 0.000 claims abstract description 14
- 238000004821 distillation Methods 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims description 10
- 238000005303 weighing Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 8
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 7
- 235000019441 ethanol Nutrition 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 abstract description 4
- 230000003197 catalytic effect Effects 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000005191 phase separation Methods 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- -1 dodecyl ethyl Chemical group 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011964 heteropoly acid Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0239—Quaternary ammonium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/49—Esterification or transesterification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a method for synthesizing ethyl laurate by taking a eutectic solvent BAC-DES based on benzyl trimethyl ammonium chloride as a catalyst, wherein the catalyst BAC-DES is prepared by mixing and reacting benzyl trimethyl ammonium chloride and p-toluenesulfonic acid according to a molar ratio of 1: 3. The ethyl laurate is prepared by carrying out esterification reaction on lauric acid and excessive absolute ethyl alcohol at a certain temperature, and sequentially carrying out phase separation, atmospheric distillation, reduced pressure distillation and the like. The eutectic solvent BAC-DES disclosed by the invention is used as a catalyst for esterification reaction, has a series of advantages of high catalytic activity, easiness in separation from a reaction system, stable reusability, mild reaction conditions and the like, and greatly reduces the production cost of the ethyl laurate while meeting the requirements of a green synthesis process.
Description
Technical Field
The invention belongs to the field of organic chemical synthesis, relates to a preparation method of organic chemical ethyl laurate, and particularly relates to a method for synthesizing ethyl laurate by using a eutectic solvent.
Background
Ethyl laurate, also known as dodecyl ethyl ester, is a colorless or pale yellow oily liquid, has special fruity odor, is widely applied in many fields, is widely used as essence and spice in the fields of food and daily chemicals, and can be used as a lubricant, a plasticizer, a softening agent and an organic synthetic intermediate.
The traditional preparation process of the ethyl laurate usually uses concentrated sulfuric acid as a catalyst, but the preparation process has many side reactions, the subsequent products are not easy to separate, the environmental pollution is serious, and the preparation process does not meet the requirements of green environmental protection at present, so researchers are dedicated to research and development of the green environmental-protection high-efficiency ethyl laurate preparation process, and the heteropoly acid, solid super acid and the like are used as catalysts to prepare the ethyl laurate in the successive literature reports.
The eutectic solvent is a two-component or three-component eutectic mixture formed by combining a hydrogen bond acceptor (such as quaternary ammonium salt) and a hydrogen bond donor (such as amide, carboxylic acid, polyalcohol and other compounds) in a certain molar ratio, so that the acid strong-polarity eutectic solvent can be prepared by designing the composition, can be used as an esterification reaction catalyst, has a series of advantages of high catalytic activity, easiness in separation from a reaction system, high reusability and the like, and has great industrial application value and development potential.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and discloses a method for synthesizing ethyl laurate by using a eutectic solvent based on benzyl trimethyl ammonium chloride as a catalyst, and a target product is obtained at a lower cost by controlling reaction process conditions so as to meet the requirements of related fields.
The method of the invention comprises the following steps:
(1) weighing a proper amount of benzyl trimethyl ammonium chloride and p-toluenesulfonic acid respectively, enabling the molar ratio of the benzyl trimethyl ammonium chloride to be 1:3, respectively drying the benzyl trimethyl ammonium chloride and the p-toluenesulfonic acid in vacuum at 65 ℃ for 1 h, mixing the benzyl trimethyl ammonium chloride and the p-toluenesulfonic acid, stirring the mixture at 70 ℃ to react to obtain a clear and transparent solution, wherein a product obtained by the reaction is a benzyl trimethyl ammonium chloride-based eutectic solvent catalyst BAC-DES, and placing the BAC-DES in a silica gel dryer for later use.
(2) Weighing a proper amount of reactants, namely lauric acid and absolute ethyl alcohol respectively, so that the molar ratio of the lauric acid to the absolute ethyl alcohol is 1: 1.5-3, stirring and heating to 60-80 ℃, then adding a proper amount of catalyst BAC-DES into a three-neck flask and reacting at the temperature, wherein the mass of the added catalyst is 2-6% of the total mass of the reactants, the rotating speed is 500 rpm, and the reaction time is 2-5 h.
(3) After the reaction is finished, dividing the reaction system into a water phase and an oil phase by a separating funnel while the reaction system is hot, and carrying out vacuum drying on the water phase at 65 ℃ to recover a catalyst BAC-DES; and (3) carrying out normal pressure distillation on the oil phase to remove excessive ethanol, then carrying out reduced pressure distillation to collect fractions, wherein the distillation temperature is 90-105 ℃, the pressure is 150-300 Pa, and the obtained fractions are dried by anhydrous calcium chloride to obtain the product ethyl laurate.
The invention has the innovation point that the eutectic solvent BAC-DES is used as the catalyst for the esterification reaction, the catalyst has a series of advantages of high catalytic activity, easy separation from a reaction system, stable reusability, mild reaction conditions and the like, and the production cost of the ethyl laurate can be reduced while the requirement of a green synthesis process is met.
Detailed Description
Preparation of eutectic solvent catalyst BAC-DES
Respectively weighing 5.57g (0.03 mol) of benzyltrimethylammonium chloride and 15.50g (0.09 mol) of p-toluenesulfonic acid, respectively drying the benzyltrimethylammonium chloride and the p-toluenesulfonic acid under vacuum at 65 ℃ for 1 h, mixing the benzyltrimethylammonium chloride and the p-toluenesulfonic acid, stirring the mixture at 70 ℃ to react to obtain a clear and transparent solution, wherein a product obtained by the reaction is a eutectic solvent catalyst BAC-DES, and placing the BAC-DES in a silica gel dryer for later use.
Example 1
Respectively weighing 20.03g (0.1 mol) of lauric acid and 6.91g (0.15 mol) of absolute ethyl alcohol, adding the lauric acid and the absolute ethyl alcohol into a three-neck flask, stirring and heating to 70 ℃, then adding 1.08g of a catalyst BAC-DES into the three-neck flask, and reacting at the temperature, wherein the rotating speed is 500 rpm, and the reaction time is 5 hours; after the reaction, the reaction solution was separated into water and oil phases by a separatory funnel while it was hot, and the aqueous phase was vacuum-dried at 65 ℃ to recover the catalyst. And (3) distilling the oil phase at normal pressure to remove excessive ethanol, then distilling under reduced pressure (the temperature is 100-105 ℃, and the pressure is 250-300 Pa) to collect a fraction, drying the fraction by using anhydrous calcium chloride, and identifying the fraction as ethyl laurate by GC-MS, wherein the yield is 85.66%.
Example 2
Respectively weighing 20.03g (0.1 mol) of lauric acid and 9.21g (0.2 mol) of absolute ethyl alcohol, adding the lauric acid and the absolute ethyl alcohol into a three-neck flask, stirring and heating to 80 ℃, then adding 0.59g of a catalyst BAC-DES into the three-neck flask, and carrying out reaction at the temperature, wherein the rotating speed is 500 rpm, and the reaction time is 3.5 hours; after the reaction, the reaction solution was separated into water and oil phases by a separatory funnel while it was hot, and the aqueous phase was vacuum-dried at 65 ℃ to recover the catalyst. And (3) distilling the oil phase at normal pressure to remove excessive ethanol, then distilling under reduced pressure (the temperature is 95-100 ℃, and the pressure is 200-250 Pa) to collect a fraction, drying the fraction by using anhydrous calcium chloride, and identifying the fraction as ethyl laurate by GC-MS, wherein the yield is 86.73%.
Example 3
Respectively weighing 20.03g (0.1 mol) of lauric acid and 13.82g (0.3 mol) of absolute ethyl alcohol, adding the lauric acid and the absolute ethyl alcohol into a three-neck flask, stirring and heating to 60 ℃, then adding 1.35g of a catalyst BAC-DES into the three-neck flask, and reacting at the temperature, wherein the rotating speed is 500 rpm, and the reaction time is 5 hours; after the reaction, the reaction solution was separated into water and oil phases by a separatory funnel while it was hot, and the aqueous phase was vacuum-dried at 65 ℃ to recover the catalyst. And (3) distilling the oil phase at normal pressure to remove excessive ethanol, then distilling under reduced pressure (the temperature is 90-95 ℃, and the pressure is 150-200 Pa) to collect a fraction, drying the fraction by using anhydrous calcium chloride, and identifying the fraction as ethyl laurate by GC-MS, wherein the yield is 88.38%.
Example 4
Respectively weighing 20.03g (0.1 mol) of lauric acid and 9.21g (0.2 mol) of absolute ethyl alcohol, adding the lauric acid and the absolute ethyl alcohol into a three-neck flask, stirring and heating to 80 ℃, then adding 1.75g of a catalyst BAC-DES into the three-neck flask, and reacting at the temperature, wherein the rotating speed is 500 rpm, and the reaction time is 2 hours; after the reaction, the reaction solution was separated into water and oil phases by a separatory funnel while it was hot, and the aqueous phase was vacuum-dried at 65 ℃ to recover the catalyst. And (3) distilling the oil phase at normal pressure to remove excessive ethanol, then distilling under reduced pressure (the temperature is 100-105 ℃, and the pressure is 250-300 Pa) to collect a fraction, drying the fraction by using anhydrous calcium chloride, and identifying the fraction as ethyl laurate by GC-MS, wherein the yield is 91.26%.
Example 5
Respectively weighing 20.03g (0.1 mol) of lauric acid and 9.21g (0.2 mol) of absolute ethyl alcohol, adding the weighed materials into a three-neck flask, stirring and heating the materials to 75 ℃, then adding the catalyst BAC-DES recovered in example 1 into the three-neck flask, and carrying out reaction at the temperature, wherein the rotating speed is 500 rpm, and the reaction time is 5 hours; after the reaction, the reaction solution was separated into water and oil phases by a separatory funnel while it was hot, and the aqueous phase was vacuum-dried at 65 ℃ to recover the catalyst. And (3) distilling the oil phase at normal pressure to remove excessive ethanol, then distilling under reduced pressure (the temperature is 100-105 ℃, and the pressure is 250-300 Pa) to collect a fraction, drying the fraction by using anhydrous calcium chloride, and identifying the fraction as ethyl laurate by GC-MS, wherein the yield is 88.16%.
Claims (3)
1. A method for synthesizing ethyl laurate by using a eutectic solvent based on benzyl trimethyl ammonium chloride as a catalyst is characterized by comprising the following steps:
(1) weighing a proper amount of benzyl trimethyl ammonium chloride and p-toluenesulfonic acid respectively, enabling the molar ratio of the benzyl trimethyl ammonium chloride to be 1:3, respectively drying the benzyl trimethyl ammonium chloride and the p-toluenesulfonic acid in vacuum at 65 ℃ for 1 h, mixing the benzyl trimethyl ammonium chloride and the p-toluenesulfonic acid, stirring the mixture at 70 ℃ to react to obtain a clear and transparent solution, wherein a product obtained by the reaction is a benzyl trimethyl ammonium chloride-based eutectic solvent catalyst BAC-DES, and placing the BAC-DES in a silica gel dryer for later use;
(2) weighing a proper amount of reactant lauric acid and absolute ethyl alcohol respectively, stirring and heating to a specified temperature, then adding a proper amount of catalyst BAC-DES into a three-neck flask, and reacting at the temperature for 2-5 h;
(3) after the reaction is finished, dividing the reaction system into a water phase and an oil phase by a separating funnel while the reaction system is hot, and carrying out vacuum drying on the water phase at 65 ℃ to recover a catalyst BAC-DES; and (3) carrying out normal pressure distillation on the oil phase to remove excessive ethanol, then carrying out reduced pressure distillation to collect fractions, wherein the distillation temperature is 90-105 ℃, the pressure is 150-300 Pa, and the obtained fractions are dried by anhydrous calcium chloride to obtain the product ethyl laurate.
2. The method according to claim 1, wherein the molar ratio of lauric acid to absolute ethyl alcohol in the step (2) is 1: 1.5-3, and the mass of the catalyst is 2% -6% of the total mass of the reactants.
3. The method according to claim 1, wherein the reaction temperature in the step (2) is 60 ℃ to 80 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911331547.9A CN111039783A (en) | 2019-12-21 | 2019-12-21 | Method for synthesizing ethyl laurate by taking eutectic solvent based on benzyltrimethylammonium chloride as catalyst |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911331547.9A CN111039783A (en) | 2019-12-21 | 2019-12-21 | Method for synthesizing ethyl laurate by taking eutectic solvent based on benzyltrimethylammonium chloride as catalyst |
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| Publication Number | Publication Date |
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| CN111039783A true CN111039783A (en) | 2020-04-21 |
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| CN201911331547.9A Pending CN111039783A (en) | 2019-12-21 | 2019-12-21 | Method for synthesizing ethyl laurate by taking eutectic solvent based on benzyltrimethylammonium chloride as catalyst |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112899313A (en) * | 2021-03-23 | 2021-06-04 | 华南理工大学 | Acidic eutectic solvent, preparation and application thereof in pretreatment of straws to improve enzymolysis efficiency |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102336633A (en) * | 2011-07-27 | 2012-02-01 | 哈尔滨理工大学 | Preparation method of 2,4-dicumyl phenol |
| CN109400476A (en) * | 2018-12-06 | 2019-03-01 | 华东理工大学 | A kind of preparation method of long-chain ester |
-
2019
- 2019-12-21 CN CN201911331547.9A patent/CN111039783A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102336633A (en) * | 2011-07-27 | 2012-02-01 | 哈尔滨理工大学 | Preparation method of 2,4-dicumyl phenol |
| CN109400476A (en) * | 2018-12-06 | 2019-03-01 | 华东理工大学 | A kind of preparation method of long-chain ester |
Non-Patent Citations (1)
| Title |
|---|
| KUN LI 等: "Kinetic study on the reaction of lauric acid with ethanol catalyzed by deep eutectic solvent based on cetyl trimethyl ammonium bromide", INT. J. CHEM. KINET., vol. 51, 21 February 2019 (2019-02-21), pages 329 - 336, XP071658151, DOI: 10.1002/kin.21256 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112899313A (en) * | 2021-03-23 | 2021-06-04 | 华南理工大学 | Acidic eutectic solvent, preparation and application thereof in pretreatment of straws to improve enzymolysis efficiency |
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