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O-phenyl phenoxyalkyl acrylate and methods for producing the same

一种邻苯基苯氧烷基丙烯酸酯、丙烯酸酯的技术，应用在无溶剂制备邻苯基苯氧烷基丙烯酸酯领域，能够解决反应时间长、反应条件严苛、工艺繁琐等问题，达到高转化率、降低生产成本、减少环境的危害的效果

Active Publication Date: 2020-05-01
CHINA PETROCHEM DEVMENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The traditional production method of o-phenylphenoxy alkyl acrylate is esterification synthesis. Although this method has the characteristics of high yield, however, this method requires the use of organic solvents, resulting in the need to separate the solvent through a purification process. This purification process needs to be operated at high temperature. Even if a polymerization inhibitor is used to suppress it, it is still difficult to avoid the occurrence of polymerization. There are problems such as harsh reaction conditions, long reaction time, and cumbersome process.

Method used

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  • O-phenyl phenoxyalkyl acrylate and methods for producing the same
  • O-phenyl phenoxyalkyl acrylate and methods for producing the same
  • O-phenyl phenoxyalkyl acrylate and methods for producing the same

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preparation example Construction

[0013] According to the present invention, a preparation method of o-phenylphenoxy alkyl acrylate comprises: in the presence of a catalyst and a polymerization inhibitor and under the condition of no solvent, make an acrylate compound and a compound having the following formula (I) Transesterification of Phenyl Alcohols

[0014]

[0015] To obtain the o-phenylphenoxy alkyl acrylate with the following formula (II)

[0016]

[0017] Wherein, the catalyst is a tin compound or a titanium compound;

[0018] And n represents an integer of 0 to 8, and R represents hydrogen or methyl.

[0019] In a specific embodiment, the acrylate compound is represented by the structure of formula (III):

[0020]

[0021] Wherein, R represents hydrogen or methyl; and X represents C1-C4 alkyl, among which C1-C2 alkyl is especially preferred.

[0022] In a specific embodiment, the acrylate compound is selected from the group consisting of methyl acrylate, ethyl acrylate, methyl methacrylat...

Embodiment 1

[0058] Ethyl acrylate (1800g, 17.98mole), 2-(2-biphenyloxy)ethanol (OPPEO) (1100g, 5.13mole), 1% by weight of inhibitor 6-tert-butyl-2,4- Dimethylphenol and 1.4% by weight of dioctyltin oxide are placed in a round-bottomed flask as a catalyst, and the temperature is raised to about 110 to 120°C. At the same time, the top temperature of the distillation equipment above is controlled at 78°C to make the ethyl acrylate The ester and the by-product ethanol form an azeotrope to distill off, so that the reactants in the flask undergo a transesterification reaction, and the reaction time is about 4 hours; after the reaction is completed, the unreacted acrylate compound is separated by vacuum distillation; finally, the The o-phenylphenoxyalkyl acrylate product after vacuum distillation is filtered and purified to obtain the o-phenylphenoxyalkyl acrylate product with a conversion rate of 92% and a selectivity greater than 97%.

[0059] According to the standard test method of ASTM-D120...

Embodiment 2

[0061] The preparation method is the same as in Example 1, but the dioctyltin oxide is replaced with 3% by weight of tetraisopropyl titanate, and the transesterification reaction time is 6 hours, and o-phenylbenzene with an Apha color value greater than 500 can be obtained. The oxyalkyl acrylate product has a conversion rate of 90% and a selectivity greater than 95%.

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Abstract

A method for produding o-phenyl phenoxyalkyl acrylate comprises the following steps: in the presence of a catalyst and a polymerization inhibitor and in the absence of a solvent, the acrylate compoundand the biphenyl alcohol compound are subjected to a transesterification reaction to obtain o-phenylphenoxyalkyl acrylate with the following formula (II); wherein the catalyst is a compound containing a tin element or a titanium element. According to the method of the present disclosure, the o-phenyl phenoxyalkyl acrylate having transparency and high refractive index can be obtained. Moreover, the method of the present disclosure has the characteristics of high conversion rate and high selectivity, and does not need to add other organic solvents, so that many purification processes can be saved, and the production cost is effectively reduced, which has the value of industrial application.

Description

technical field [0001] The invention relates to a method for preparing o-phenylphenoxy alkyl acrylate, in particular to a solvent-free method for preparing o-phenylphenoxy alkyl acrylate. Background technique [0002] Acrylic esters containing aromatic rings are mainly used in the field of optical materials, such as optical films, optical lenses, optical lenses, and optical resins, due to their good transparency and high refractive index. Among them, o-phenylphenoxyalkyl acrylate can best meet the requirements of high gloss and high transparency in these fields. Recently, this o-phenylphenoxyalkyl acrylate has been widely used in wear-resistant optical materials , Anti-scratch and wear-resistant self-repairing brightening film coatings, high refractive index brightening coatings and optical lens sheets, etc. [0003] The traditional production method of o-phenylphenoxy alkyl acrylate is esterification synthesis. Although this method has the characteristics of high yield, ho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/54C07C67/03C07C67/54
CPCC07C67/03C07C67/54C07C69/54B01J31/122B01J31/0212C07C67/02C07C69/52B01J31/0211B01J2531/42B01J2231/49B01J2531/002B01J31/38C08K5/57
Inventor 陈郁森黄敏嘉柳佑樵张芷维
Owner CHINA PETROCHEM DEVMENT
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