CN111848402A - Preparation method and application of carboxylic acid isooctyl alcohol ester - Google Patents
Preparation method and application of carboxylic acid isooctyl alcohol ester Download PDFInfo
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- CN111848402A CN111848402A CN202010736526.1A CN202010736526A CN111848402A CN 111848402 A CN111848402 A CN 111848402A CN 202010736526 A CN202010736526 A CN 202010736526A CN 111848402 A CN111848402 A CN 111848402A
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- 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
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- 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
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
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- 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
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
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- 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
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0285—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre also containing elements or functional groups covered by B01J31/0201 - B01J31/0274
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- 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
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/025—Sulfonic acids
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- Y02P20/00—Technologies relating to chemical industry
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Abstract
The invention relates to a preparation method and application of carboxylic acid isooctyl alcohol ester. The method comprises the following steps: and (2) in the presence of imidazole sulfonate ionic liquid, reacting carboxylic acid with isooctanol to obtain the carboxylic acid isooctanol ester. The method of the invention adopts the imidazole sulfonate ionic liquid as the catalyst for the reaction of carboxylic acid and isooctanol, can carry out esterification reaction under the condition of no solvent, and has short reaction time (3 hours) and high conversion rate (more than 90 percent). The finished product can be obtained by distillation, the material feeding amount of the single-kettle reaction material is large, and the ionic liquid can be recycled; and a large amount of solvents are not needed, and the product separation process is simple and environment-friendly. The carboxylic acid isooctyl ester obtained by the preparation method can be used for preparing modified organic silicon microspheres.
Description
Technical Field
The invention relates to a preparation method of isooctyl carboxylate.
Background
The industrial fatty acid ester has multiple applications, and is widely used for synthesizing high-grade surfactants, additives of high-grade lubricating oil and fuel, emulsifier products, solvents of spices and the like.
Fatty acid esters, in particular fatty acid esters of isooctanol, are a very important class of chemical raw materials, which are used in various fields. For example, 2-ethylhexyl palmitate (2-EHP) can be applied to the field of chemical products, and has good skin moistening effect, low chroma and no smell; the isooctyl stearate (2-EHS) can be used as an internal lubricant of PVC and has excellent lubricating effect; 55 percent (2-EHP-55) of the palmitic acid 2-ethylhexyl ester can be used in the field of textile lubrication and is an excellent spinning yarn lubricating auxiliary agent.
Currently, ester compounds can be prepared by direct esterification or transesterification of alcohols with acids (including ester-to-alcohol, ester-to-acid, or ester-to-ester interchange) reactions. These preparation methods are generally carried out in the presence of a catalyst using a solvent, thereby resulting in a complicated subsequent separation process, and the reaction efficiency is low due to the relatively limited input amount of reactants in the reaction vessel due to the presence of the solvent.
There remains a need in the art for a simple and efficient method for preparing isooctyl carboxylate.
In view of this need, the present invention provides a process for preparing isooctyl carboxylate.
Disclosure of Invention
The invention provides a method for preparing isooctyl carboxylate, which comprises the following steps:
in the presence of imidazole sulfonate ionic liquid, carboxylic acid reacts with isooctyl alcohol to obtain carboxylic acid isooctyl alcohol ester; the sulfonic acid imidazole ionic liquid is an organic soluble salt consisting of anions and cations.
In one embodiment, the method comprises performing under solvent-free conditions.
In one embodiment, the sulfonic acid imidazole ionic liquid has the following cationic groups:
in one embodiment, the anion of the sulfonic acid imidazole ionic liquid is selected from sulfate, p-toluenesulfonate, methylsulfonate, 4-hydroxybenzenesulfonate, sulfamate.
In one embodiment, the anion of the imidazolium sulfonate ionic liquid is selected from
In one embodiment, the amount of the imidazole sulfonate ionic liquid is 3 to 30 mol% of the amount of the carboxylic acid.
In one embodiment, the amount of the imidazole sulfonate ionic liquid is 5 to 10 mol% of the amount of the carboxylic acid.
In one embodiment, the sulfonic acid imidazole ionic liquid is recyclable.
In one embodiment, the temperature of the reaction is 95 to 110 ℃. .
In one embodiment, the carboxylic acid is selected from acetic acid, stearic acid, and palmitic acid.
In one embodiment, the molar ratio of the carboxylic acid to the isooctanol is from 5:1 to 1: 5.
In one embodiment, the molar ratio of the carboxylic acid to the isooctanol is from 2:1 to 1: 2.
In one embodiment, the method further comprises: separating the ionic liquid and the product isooctyl carboxylate from the reaction mixture; and using the separated ionic liquid as the ionic liquid.
The invention also provides an application of the carboxylic acid isooctyl alcohol ester, and the carboxylic acid isooctyl alcohol ester is used for preparing modified organic silicon microspheres and has the advantages of simple process, safety and environmental protection.
The invention has the beneficial effects that:
the method of the invention adopts the imidazole sulfonate ionic liquid as the catalyst for the reaction of carboxylic acid and isooctanol, can carry out esterification reaction under the condition of no solvent, has short reaction time, and can reach a conversion rate of more than 90 percent within 3 hours. The finished product can be obtained by distillation, the material feeding amount of the single-kettle reaction material is large, and the ionic liquid can be recycled; and a large amount of solvents are not needed, and the product separation process is simple and environment-friendly.
Detailed Description
The technical solution of the present invention is further explained below according to specific embodiments. The scope of protection of the invention is not limited to the following examples, which are set forth for illustrative purposes only and are not intended to limit the invention in any way.
The present application provides a process for preparing an isooctyl carboxylate comprising:
and (2) in the presence of imidazole sulfonate ionic liquid, reacting carboxylic acid with isooctanol to obtain the carboxylic acid isooctanol ester.
In one embodiment, the process of the invention comprises conducting under solvent-free conditions. The term "carried out in the absence of a solvent" means that a solvent is not intentionally added to the reaction system, but does not mean that each reaction raw material is required to be pure, and each reaction raw material itself may contain a small amount, for example, less than 10% by weight, of a substance that may function as a solvent.
The ionic liquid is an organic soluble salt composed of anions and cations, and has extremely low vapor pressure, low melting point, high polarity, incombustibility, strong acid resistance, high thermal stability, high conductivity and the like. Different ion species can be matched for different applications. Common applications include organic synthesis (alternative solvents; phase transfer reagents), co-catalysts (hydrogenation; esterification; oxidation), extraction applications, and electrochemical applications, among others. The invention uses the imidazole sulfonate ionic liquid as a catalyst for the reaction of carboxylic acid and isooctanol, can carry out esterification reaction under the condition of no solvent, has short reaction time, and can reach a conversion rate of more than 90 percent in 3 hours. The finished product can be obtained by distillation, the charging amount of the single-kettle reaction material is large, and the ionic liquid catalyst is separated from the reaction system by cooling and standing the crude product. By standing and layering, the ionic liquid layer can be easily recovered, and water can be removed by heating vacuum or solvent azeotropy, so that the ionic liquid can be reused.
The sulfonic acid imidazole ionic liquid has recoverability. Thus, in one embodiment, the method further comprises: separating the ionic liquid and the product isooctyl carboxylate from the reaction mixture; and using the separated ionic liquid as the ionic liquid.
In general, water is produced when a carboxylic acid reacts with an alcohol. When the sulfonic acid imidazole ionic liquid is used, the sulfonic acid imidazole ionic liquid plays a role of a catalyst, and can generate strong binding force with water, so that the water in a reaction kettle cannot perform reverse reaction. However, when a general acid such as a sulfonic acid catalyst is used, it plays only a catalytic role and does not prevent the water in the reaction tank from performing a reverse reaction. Therefore, the ionic liquid used in the invention has strong dehydration effect, so that the product conversion rate of the ionic liquid catalyst is higher than that of the catalyst using the non-ionic liquid.
In one embodiment, the sulfonic acid imidazole ionic liquid has the following cationic groups:
in one embodiment, the anion of the sulfonic acid imidazole ionic liquid can be selected from p-toluenesulfonate, methylsulfonate, 4-hydroxybenzenesulfonate and sulfamate.
In one embodiment, the anion of the imidazolium sulfonate ionic liquid is selected from
The ionic liquid can be prepared according to the following reaction formula:
compared with other types of ionic liquids, the sulfonic acid imidazole ionic liquid has the following advantages: strong dehydration effect, simple preparation and good water solubility.
In one embodiment, the dosage of the imidazole sulfonate ionic liquid is 5-10 mol%, preferably 10 mol%, of the carboxylic acid raw material, and after three hours of reaction, a conversion rate of 94% can be achieved.
In one embodiment, the temperature of the reaction is 95 to 110 ℃. The process of the invention may be carried out at atmospheric pressure, for example at a pressure of one atmosphere.
In one embodiment, carboxylic acids that may be used in the present invention include various types of carboxylic acids, such as saturated fatty acids, unsaturated fatty acids, aromatic carboxylic acids, and the like. In one embodiment, the carboxylic acid is selected from acetic acid, stearic acid, and palmitic acid. In one embodiment, the molar ratio of the carboxylic acid to the isooctanol is from 5:1 to 1: 5. Preferably, the molar ratio of the carboxylic acid to the isooctanol is from 2:1 to 1: 2.
Preparation example-preparation of imidazole sulfonate Ionic liquids
Cationic groups of the imidazole sulfonate ionic liquid used in the following examples are 1-methylimidazole derivatives, and anionic groups X are methylsulfonate.
The preparation method comprises the steps of stirring and mixing 1, 3-sultone (0.5mol,61 g) and 400 g of toluene in a one-liter reaction bottle, slowly dropwise adding 1-methylimidazole (0.5mol,41 g) into the bottle, heating to 80 ℃ after dropwise adding, reacting for three hours, adding anhydrous methanesulfonic acid (0.5mol, 48 g) after the temperature in the bottle is reduced to room temperature, stirring for one hour, transferring reactants into an extraction bottle, and collecting a lower ionic liquid layer.
Example 1
60g of acetic acid (1 equivalent), 130g of isooctanol (1 equivalent) and sulfonic acid imidazole ionic liquid (the dosage of which is 10mol percent of acetic acid and 30g) are fed into a reaction kettle and reacted for three hours at the temperature of 100 ℃ and the pressure of one atmosphere. And cooling and standing after the reaction is finished, layering the ionic liquid catalyst and the reaction system, separating out the ionic liquid at the lower layer, and obtaining 178g of a semi-finished product of isooctyl acetate (2EHA) as a product from the organic matter at the upper layer, wherein the conversion rate of analysis is 80%.
Example 2
120g of acetic acid (2 equivalents), 130g of isooctanol (1 equivalent) and sulfonic acid imidazole ionic liquid (the dosage of which is 10mol percent of the acetic acid and 60g) are fed into a reaction kettle and reacted for three hours at the temperature of 100 ℃ and the pressure of one atmosphere. And cooling and standing after the reaction is finished, layering the ionic liquid catalyst and the reaction system, separating out the ionic liquid at the lower layer, and obtaining 208g of a semi-finished product of isooctyl acetate (2EHA) as a product from an organic matter at the upper layer, wherein the conversion rate is 90% by analysis.
Example 3
120g of acetic acid (2 equivalents), 130g of isooctanol (1 equivalent) and sulfonic acid imidazole ionic liquid (the dosage of which is 5mol percent of acetic acid and 30g) are fed into a reaction kettle and reacted for three hours at the temperature of 100 ℃ and the pressure of one atmosphere. And cooling and standing after the reaction is finished, layering the ionic liquid catalyst and the reaction system, separating out the ionic liquid at the lower layer, and obtaining 218g of a semi-finished product of isooctyl acetate (2EHA) as a product from the organic matter at the upper layer, wherein the conversion rate is 90% by analysis.
Example 4
284g of stearic acid HA150(1 equivalent), 260g of isooctanol (2 equivalents) and sulfonic acid imidazole ionic liquid (the dosage of which is 10mol percent of stearic acid and 60g) are fed into a reaction kettle and reacted for three hours at the temperature of 100 ℃ and the pressure of one atmosphere. And cooling and standing after the reaction is finished, layering an ionic liquid catalyst and a reaction system, separating out lower-layer ionic liquid, and obtaining 535g of a semi-finished product of isooctyl stearate (2EHS), wherein the conversion rate of analysis is more than 95%.
Example 5
256g of palmitic acid (1 equivalent), 130g of isooctanol (1 equivalent) and sulfonic acid imidazole ionic liquid (the dosage of which is 10mol percent of the palmitic acid and is 30g) are fed into a reaction kettle and reacted for three hours at the temperature of 100 ℃ and the pressure of one atmosphere. And cooling and standing after the reaction is finished, layering an ionic liquid catalyst and a reaction system, separating ionic liquid at the lower layer to obtain 351g of a semi-finished product of isooctyl palmitate (2EHP), wherein the conversion rate of analysis is more than 85%.
Example 6
256g of palmitic acid (1 equivalent), 260g of isooctanol (2 equivalents) and sulfonic acid imidazole ionic liquid (10 mol% of palmitic acid, 30g) were charged into a reaction kettle and reacted at 100 ℃ and one atmosphere pressure for three hours. And cooling and standing after the reaction is finished, layering an ionic liquid catalyst and a reaction system, separating out ionic liquid at the lower layer to obtain 480g of a semi-finished product of isooctyl palmitate (2EHP), wherein the analyzed conversion rate is about 94%.
Comparative example
256g of palmitic acid (1 eq), 130g of isooctanol (1 eq) and p-toluenesulfonic acid (10 mol% of palmitic acid, 17g) were charged in a reaction vessel and reacted at 100 ℃ and one atmosphere pressure for three hours. And cooling and standing after the reaction is finished, layering an ionic liquid catalyst and a reaction system, separating ionic liquid at the lower layer to obtain 372g of a semi-finished product of isooctyl palmitate (2EHP), wherein the analyzed conversion rate is about 49%.
TABLE 1
Table 1 shows the results of examples 1-6 and comparative examples, which show that the method of the present invention can perform esterification reaction without solvent by using the imidazole sulfonate ionic liquid as the catalyst for the reaction of carboxylic acid and isooctanol, and has short reaction time (3 hours) and high conversion rate (more than 90%). The finished product can be obtained by distillation, the material feeding amount of the single-kettle reaction material is large, and the ionic liquid can be recycled; and a large amount of solvents are not needed, and the product separation process is simple and environment-friendly.
The results of example 5 and comparative example (using a sulfonic acid catalyst) at three hours of reaction showed that the comparative example had only 49% conversion and that even with increasing reaction time, the conversion did not increase further. The main reason is that the ionic liquid used in the examples can not perform the reverse reaction of water in the reaction kettle except for the role of the catalyst and can generate strong binding force with water, while the p-toluenesulfonic acid catalyst in the comparative example can only perform the catalytic role and cannot prevent the reverse reaction of water in the reaction kettle. Therefore, the ionic liquid used in the invention has strong dehydration effect, so that the product conversion rate of the ionic liquid catalyst is higher than that of the catalyst using the non-ionic liquid.
The method can help easily recover the ionic liquid layer by standing and layering the finished product and the ionic liquid after the reaction is finished, and can help repeatedly use the ionic liquid by removing water in a heating vacuum or solvent azeotropic mode. The final layer can be distilled to obtain a high-purity ester.
It should be noted by those skilled in the art that the described embodiments of the present invention are merely exemplary and that various other substitutions, alterations, and modifications may be made within the scope of the present invention. Accordingly, the present invention is not limited to the above-described embodiments, but is only limited by the claims.
Claims (10)
1. A process for preparing an isooctyl carboxylate comprising:
in the presence of imidazole sulfonate ionic liquid, carboxylic acid reacts with isooctyl alcohol to obtain carboxylic acid isooctyl alcohol ester; the sulfonic acid imidazole ionic liquid is an organic soluble salt consisting of anions and cations.
2. The process of claim 1, wherein the process comprises performing under solventless conditions.
3. A process according to claim 1, wherein the sulfonic acid imidazole-based ionic liquid has the following cationic groups:
4. the method according to claim 1, wherein the anion of the sulfonic acid imidazole ionic liquid is selected from sulfate, p-toluenesulfonate, methylsulfonate, 4-hydroxybenzenesulfonate and sulfamate.
5. A process according to claim 1, wherein the anion of the imidazolium sulfonate ionic liquid is selected from
6. A method according to claim 3, wherein the amount of the sulfonic acid imidazole ionic liquid is 3-30 mol%, preferably 5-10 mol% of the amount of the carboxylic acid.
7. A process according to any one of claims 1 to 6, wherein the imidazolium sulfonate ionic liquid is recyclable.
8. The method of claims 1-6, wherein the carboxylic acid is selected from the group consisting of acetic acid, stearic acid, and palmitic acid.
9. The process of claims 1-6 wherein the molar ratio of said carboxylic acid to said isooctanol is from 5:1 to 1: 5.
10. The method as recited in claims 1-6, wherein the method further comprises: separating the ionic liquid and the product isooctyl carboxylate from the reaction mixture; and using the separated ionic liquid as the ionic liquid.
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