Method for producing ethylenically unsaturated group-containing garma-butyrolactone derivative

A manufacturing method and unsaturated technology, applied in the fields of organic chemistry, organic chemistry, etc., can solve the problems of difficult compound manufacturing, poor reaction selectivity, and difficult to obtain.

Pending Publication Date: 2019-03-15
JNC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, when the above method is used to produce a hydroxyl compound having a β-propiolactone skeleton, it is difficult to produce a compound as a raw material and difficult to obtain it, or there are many side reactions and the reaction selectivity is poor, so it is difficult to implement it industrially.
Therefore, industrial production of β-hydroxy compounds of γ-butyrolactones is still difficult

Method used

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  • Method for producing ethylenically unsaturated group-containing garma-butyrolactone derivative
  • Method for producing ethylenically unsaturated group-containing garma-butyrolactone derivative
  • Method for producing ethylenically unsaturated group-containing garma-butyrolactone derivative

Examples

Experimental program
Comparison scheme
Effect test

experiment example 1

[0129] In a glove box under a nitrogen atmosphere, 21.3 g of glycidylmethacrylate (Glycidylmethacrylate, GMA), 85.24 g of 2-acetoxy-1-methoxypropane, 0.02 g of 4,4′-methylene Bis(2,6-di-tert-butylphenol) (BBHT), 3.0 ml of 1 mol / L triethylaluminum (15% hexane solution, manufactured by Wako Pure Chemical Industries), 0.256 g of dicobalt octacarbonyl into a 200 ml autoclave container and mixed (initial concentration: 20% by mass). Install the CO gas line into the autoclave, and perform three replacements with CO gas. CO gas was introduced until the pressure became 5.0 MPa and heated. The reaction was carried out for 240 minutes at a temperature of 90° C. and an internal pressure of 4.8 MPa to 5.0 MPa.

[0130] After the reaction finishes, utilize GC (GC device; Shimadzu Corporation GC-2014, column; Agilent J&W (AgilentJ&W) capillary GC column DB-1 60m * 0.25mmID * 0.25μm) to glycidyl methacrylate Quantitative analysis of β-methacryloyloxymethyl-β-propiolactone and β-methacrylo...

experiment example 2

[0133] The reaction was carried out in the same manner as in Experimental Example 1 except that 4,4'-methylenebis(2,6-di-tert-butylphenol) was not added.

[0134] After the reaction, use GC to quantitatively analyze glycidyl methacrylate, and use HPLC to analyze β-methacryloyloxymethyl-β-propiolactone and β-methacryloyloxy-γ-butylene Quantitative analysis of lactones. As a result, the conversion rate of glycidyl methacrylate was 99.4%, the lactone production rate was 62.7%, and β-methacryloyloxy-γ-butyrolactone (γ) The ratio of methyl-β-propiolactone (β) is γ:β=62:38. Table 1 shows the experimental conditions and results.

experiment example 3

[0136] In a glove box under a nitrogen atmosphere, 27.0 g of glycidyl methacrylate, 76.0 g of 2-acetoxy-1-methoxypropane, 0.03 g of 4,4'-methylenebis(2, 6-di-tert-butylphenol), 3.8ml of 1mol / L triethylaluminum (15% hexane solution, manufactured by Wako Pure Chemical Industries), 0.325g of dicobalt octacarbonyl were placed in a 200ml autoclave container and Mixing (initial concentration: 25% by mass). Install the CO gas line into the autoclave, and perform three replacements with CO gas. CO gas was introduced until the pressure became 5.0 MPa and heated. The reaction was carried out for 240 minutes at a temperature of 90° C. and an internal pressure of 4.8 MPa to 5.0 MPa.

[0137] After the reaction, use GC to quantitatively analyze glycidyl methacrylate, and use HPLC to analyze β-methacryloyloxymethyl-β-propiolactone and β-methacryloyloxy-γ-butylene Quantitative analysis of lactones. As a result, the conversion rate of glycidyl methacrylate was 99.4%, and the lactone produ...

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Abstract

The purpose of the present invention is to provide an industrial production method by which an ethylenically unsaturated group-containing GARMA-butyrolactone derivative is highly selectively obtainedwith use of a low-cost catalyst that is easily available. A method for producing an ethylenically unsaturated group-containing GARMA-butyrolactone derivative, wherein an ester compound represented byformula (1) and having, as terminal groups, an epoxy group and an ethylenically unsaturated group is reacted with carbon monoxide in the presence of dicobalt octacarbonyl and trialkyl aluminum. This production method is characterized in that the initial concentration of the ester compound, which is represented by formula (1) and has, as terminal groups, an epoxy group and an ethylenically unsaturated group, is from 10% by mass to 70% by mass (inclusive). In formula (1), each of R1-R5 independently represents H or an optionally branched alkyl group having 1-6 carbon atoms; and R6 represent H oran optionally branched alkyl group having 1-10 carbon atoms.

Description

technical field [0001] The present invention relates to a method for producing γ-butyrolactone derivatives containing ethylenically unsaturated groups. Background technique [0002] Ethylenically unsaturated group-containing compounds such as (meth)acrylate compounds are used in various applications such as optical materials, resist materials, coating materials, and laminated materials by copolymerizing other polymerizable monomers . [0003] A lactone skeleton has polarity, and attempts have been made to increase the polarity of a polymer obtained by polymerizing the monomer by introducing a lactone skeleton into an acrylate monomer, and to improve properties. For example, α-(meth)acryloyloxy-γ-butyrolactones are known as (meth)acrylate compounds having a five-membered ring lactone (γ-butyrolactone) skeleton (Patent Document 1) or β-(meth)acryloyloxy-γ-butyrolactones (Patent Document 2), especially industrially provided α-(meth)acryloyloxy- γ-butyrolactones, and can be u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33C07B61/00
CPCC07B61/00C07D307/33
Inventor 中山実山田浩纲池津暁峰林秀树河村栄
Owner JNC CORP
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