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Eleostearic acid ester alkylated compound containing phenolic hydroxyl, and preparation method and application of eleostearic acid ester alkylated compound

A technology for the alkylation of oleic acid esters, which is applied in the field of alkylated compounds containing phenolic hydroxyl esters and their preparation

Active Publication Date: 2016-01-20
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The Chinese invention patent with publication number CN103601703A has invented a kind of method of epoxidized methyl chelate by tung oil, which uses tung oil as raw material, and obtains methyl trophate through transesterification reaction, and then under the effect of solid acid catalyst, Synthesis of epoxidized methyl chelate by epoxidation reaction; the Chinese invention patent with publication number CN103881341A has invented a kind of tung oil derivative modified unsaturated polyester resin composition, after adding initiator and accelerator, the composition , after heat reaction and solidification, a blended structure compound of tung oil derivative monomer and unsaturated polyester macromolecule is formed; the Chinese invention patent with the publication number CN102604015A has invented methylated tung oil modified water-based polyurethane emulsion, and polyisocyanate Synthesize pure polyurethane prepolymer with oligomer polyol, add carboxyl-containing hydrophilic chain extender to carry out graft chain extension reaction of hydrophilic group, and then introduce end-capping agent containing unsaturated double bond for end-capping treatment and Add methylated tung oil, then add a neutralizing agent to neutralize the carboxyl groups to obtain a polyurethane prepolymer with carboxyl groups, add deionized water under high-speed stirring, and finally add an initiator to carry out polymerization reaction to obtain a modified water-based Polyurethane emulsion; although the above several inventions all use tung oil as a raw material, they do not involve acidic ionic liquid or solid acid as a catalyst

Method used

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  • Eleostearic acid ester alkylated compound containing phenolic hydroxyl, and preparation method and application of eleostearic acid ester alkylated compound
  • Eleostearic acid ester alkylated compound containing phenolic hydroxyl, and preparation method and application of eleostearic acid ester alkylated compound
  • Eleostearic acid ester alkylated compound containing phenolic hydroxyl, and preparation method and application of eleostearic acid ester alkylated compound

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Experimental program
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Effect test

Embodiment 1

[0042] According to the following steps to prepare the alkylated compound containing phenolic hydroxyl oleic acid ester:

[0043] (1) Synthesis and separation and purification of methyl trophic acid: add 43.6 g tung oil (0.05 mol, tung oil is calculated as acid glycerol (872)) in a 250 mL three-necked flask, install a condensing reflux device, and heat the constant temperature water bath to 70 After ℃, add the prepared NaOH / methanol solution (0.436g / 9.6g), wherein methanol: tung oil=6:1 (mol / mol), methyl alcohol 0.3mol (9.6g); NaOH is 1% (0.436g) of tung oil quality g); turn on the magnetic stirring, and stop the reaction after reacting for about 1 hour; add an appropriate amount of phosphoric acid to neutralize, transfer the reaction solution to a separatory funnel while it is still hot, and separate the glycerin layer (lower layer); Wash 3 to 4 times, remove the water phase in the lower layer, distill off methanol and most of the water under reduced pressure, and dry with an...

Embodiment 2

[0056] According to the following steps to prepare the alkylated compound containing phenolic hydroxyl oleic acid ester:

[0057] (1) Synthesis and separation and purification of ethyl chertate:

[0058]In a 250mL three-necked flask, add 43.6g tung oil (0.05mol, tung oil is calculated as acid glyceryl tungate (872)), install a condensation reflux device, and after the constant temperature water bath is heated to 60°C, add the prepared KOH / ethanol solution, wherein Ethanol: tung oil=5:1 (mol / mol), ethanol 0.25mol; KOH is 2% of the quality of tung oil; turn on the magnetic stirring, and stop the reaction after reacting for about 80min; add an appropriate amount of phosphoric acid for neutralization, and transfer the reaction solution to Separate the funnel, let it stand, separate the glycerol layer (lower layer); wash the upper liquid with hot distilled water 3 to 4 times, remove the lower water phase, distill under reduced pressure to remove ethanol and most of the water, etc.,...

Embodiment 3

[0064] According to the following steps to prepare the alkylated compound containing phenolic hydroxyl oleic acid ester:

[0065] (1) Synthesis and separation and purification of n-propyl chertate:

[0066] Add 43.6g tung oil (0.05mol, tung oil is calculated as tung-glyceride 872) in a 250mL three-necked flask), install a condensation reflux device, and after the constant temperature water bath is heated to 80°C, add the prepared KOH / n-propanol solution, Among them, n-propanol: tung oil=8:1 (mol / mol), n-propanol 0.4mol; KOH is 2% of the quality of tung oil; turn on the magnetic stirring, after reacting for about 50min, stop the reaction; add an appropriate amount of phosphoric acid for neutralization, while hot Transfer the reaction solution to a separatory funnel, let it stand, and separate the glycerin layer (lower layer); wash the upper liquid with hot distilled water for 3 to 4 times, remove the lower water phase, and distill under reduced pressure to remove n-propanol and...

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Abstract

The invention belongs to the field of organic synthesis, and specifically discloses an eleostearic acid ester alkylated compound containing a phenolic hydroxyl, and a preparation method and the application of the eleostearic acid ester alkylated compound. The eleostearic acid ester alkylated compound containing the phenolic hydroxyl is of a structure showed in a formula (1) and a formula (2) which are as shown in the description; in the formula (1) and the formula (2), R1 and R3 are straight-chain or branched-chain alkyls ranging from C1 to C4, and R2 and R4 are one or several of H, Cl, CH3, -OH, -OCH and -C(CH3)3. According to the eleostearic acid ester alkylated compound containing the phenolic hydroxyl, disclosed by the invention, the region selectivity and the alkylation degree of an eleostearic acid ester alkylation reaction can be regulated and controlled through acidic ionic liquid and the like, so that a target product can be obtained, and the prepared eleostearic acid ester alkylated compound containing the phenolic hydroxyl can be applied to the aspects of water-based UV (Ultraviolet) curing coating, water-based UV curing printing ink, water-based UV curing adhesive and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to an alkylated compound containing phenolic hydroxyl group oleic acid ester and its preparation method and application. Background technique [0002] my country's biomass resources are very rich, and many biomass resources can also be used in various forms in people's daily production and life. Among them, a wide variety of chemical products can be produced through direct reaction or deployment of natural oils, hydrolysis, etc., and due to the low price , Environmental friendliness and biodegradable characteristics are favored by people. At present, tung oil and raw lacquer, which are relatively mature in application, are traditional oily resources and natural anti-corrosion materials in my country. The main component structures of the two have certain similarities, but the performance of raw lacquer is superior. Known as the king of paint, it has the vast majority of sy...

Claims

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Application Information

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IPC IPC(8): C07C69/732C07C67/31C09D7/12C09D11/03C09D11/101C09J11/06
CPCC07C67/03C07C67/31C09D7/63C09D11/03C09D11/101C09J11/06C07C69/587C07C69/732
Inventor 杨卓鸿周闯袁腾张淑婷周健黄家健
Owner SOUTH CHINA AGRI UNIV
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