O-PHENYL PHENOXYALKYL ACRYLATE AND METHODS FOR PRODUCING THE SAME

• US 20200131110A1
• Filed: 06/20/2019
• Published: 04/30/2020
• Est. Priority Date: 10/24/2018
• Status: Active Grant

• Current Assignee: China Petrochemical Development Corporation, Taipei (Taiwan)
• Original Assignee: China Petrochemical Development Corporation, Taipei (Taiwan)
• Inventors: Chen, Yu-Sen, Huang, Min-Chia, Liu, Yu-Chiao, Chang, Chih-Wei
• Granted Patent: US 10,633,325 B1
• Time in Patent Office: Days
• CPC Class Codes: B01J 2231/49 Esterification or transesterification
• CPC Class Codes: B01J 2531/002 Materials
• CPC Class Codes: B01J 31/0211 with a metal-oxygen link
• CPC Class Codes: B01J 31/0212 Alkoxylates
• CPC Class Codes: B01J 31/122 Metal aryl or alkyl compounds
• CPC Class Codes: B01J 31/38 of titanium, zirconium or hafnium
• CPC Class Codes: C07C 67/02 by interreacting ester groups, i.e. transesterification
• CPC Class Codes: C07C 67/03 by reacting an ester group with a hydroxy group
• CPC Class Codes: C07C 69/54 Acrylic acid esters; Methacrylic acid esters
• CPC Class Codes: C08K 5/57 Organo-tin compounds

Abstract

The present disclosure provides a method for preparing o-phenyl phenoxyalkyl acrylate, including: transesterifying an acrylate-based compound with a biphenyl alcohol compound in the absence of a solvent and in the presence of a catalyst and a polymerization inhibitor to prepare the o-phenyl phenoxyalkyl acrylate represented by 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.

Claims

1. A method for preparing o-phenyl phenoxyalkyl acrylate, comprising:

transesterifying an acrylate-based compound with a biphenyl alcohol compound represented by following formula (I),

2. The method of claim 1, wherein the homogeneous catalyst is bis-(C1-C10)alkyl tin oxide.

3. The method of claim 2, wherein the bis-(C1-C10)alkyl tin oxide is at least one selected from the group consisting of dioctyltin oxide and dibutyltin oxide.

4. The method of claim 2, wherein the bis-(C1-C10)alkyl tin oxide is in an amount of from 0.5% to 1.5% by weight.

5. The method of claim 1, wherein the homogeneous catalyst is a titanate catalyst.

6. The method of claim 5, wherein the titanate catalyst is at least one selected from the group consisting of tetrabutyl titanate and tetraisopropyl titanate.

7. The method of claim 5, wherein the titanate catalyst is in an amount of from 1.5% to 3.5% by weight.

8. The method of claim 1, wherein the polymerization inhibitor is at least one selected from the group consisting of oxygen, phenothiazine, a phenolic compound, and a nitroxide free-radical compound.

9. The method of claim 8, wherein the phenolic compound is 6-tert-butyl-2,4-dimethylphenol, 2-tert-butyl hydroquinone, 2,5-di-tert-butyl hydroquinone, p-hydroxyanisole or hydroquinone.

10. The method of claim 8, wherein the nitroxide free-radical compound is piperidinol nitroxide or piperidine nitroxide phosphite.

11. The method of claim 1, wherein the polymerization inhibitor is in an amount of from 0.1% to 1.5% by weight.

12. The method of claim 8, wherein the polymerization inhibitor is the phenolic compound in an amount of from 0.5% to 1.5% by weight.

13. The method of claim 1, wherein the acrylate-based compound is selected from the group consisting of methyl acrylate, ethyl acrylate, methyl methacrylate and ethyl methacrylate.

14. The method of claim 1, wherein the transesterification is performed with a molar ratio of the acrylate-based compound to the biphenyl alcohol compound represented by the formula (I) from 2.5:

1 to 4;

1.

15. The method of claim 1, wherein the transesterification is performed in a reaction temperature from 110°

C. to 120°

C.

16. The method of claim 15, wherein the transesterification is performed in a reaction time from 4 hours to 6 hours.

17. The method of claim 1, further comprising distilling off an azeotrope containing the acrylate-based compound and a byproduct of alcohol by using a distillation apparatus in the transesterification.

18. The method of claim 1, further comprising separating an unreacted acrylate-based compound by reduced pressure distillation after the transesterification.