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Dehydroabietic acid derivative, method for producing same, and method for producing 12-carboxydehydroabietic acid derivative

A technology of dehydroabietic acid and its manufacturing method, applied in the direction of preparation of organic compounds, preparation of carboxylic acid esters, chemical instruments and methods, etc., capable of solving the problems of low heat resistance

Active Publication Date: 2013-11-13
FUJIFILM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Polylactic acid is excellent in transparency, but has low heat resistance, so its application to molded products obtained by injection molding, etc., has been limited to applications that are not exposed to high temperatures

Method used

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  • Dehydroabietic acid derivative, method for producing same, and method for producing 12-carboxydehydroabietic acid derivative
  • Dehydroabietic acid derivative, method for producing same, and method for producing 12-carboxydehydroabietic acid derivative
  • Dehydroabietic acid derivative, method for producing same, and method for producing 12-carboxydehydroabietic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0131]Synthesis of Exemplary Compound (A-1)

[0132] The exemplified compound (A-1) was synthesized by the following synthetic route.

[0133]

[0134] 0.45 Kg of oxalyl chloride was added dropwise to a mixture of 1.00 Kg of 92% dehydroabietic acid (hereinafter, also referred to as "DHA": manufactured by Arakawa Chemical Industry Co., Ltd.) and 2 L of methylene chloride at room temperature. After stirring for 5 hours, the solvent was distilled off under reduced pressure, and 0.55 Kg of methanol was added dropwise thereto. After stirring at room temperature for 5 hours, excess methanol was distilled off under reduced pressure to obtain 1.10 kg of white crystals of dehydroabietic acid methyl ester (DHA-Me).

[0135] To 1.5 L of glacial acetic acid cooled to 15° C., 500 ml of concentrated sulfuric acid was slowly added dropwise while keeping the temperature in the system at 25° C. or lower. After adding 314 g of DHA-Me obtained above and 136 g of glyoxylic acid hydrate and s...

Embodiment 2

[0138] Synthesis of Exemplary Compound (A-8)

[0139] The exemplified compound (A-8) was synthesized by the following synthetic route.

[0140] [chemical formula 16]

[0141]

[0142] To a solution of 117.7 g of the exemplary compound (A-1) synthesized in Example 1 in 500 mL of tetrahydrofuran was added dropwise 60 mL of a 50 wt / v% sodium hydroxide aqueous solution. Warm up to room temperature in this state and leave overnight. 500 mL of ethyl acetate and 200 mL of ice water were added, neutralized with concentrated hydrochloric acid, liquid-separated, washed with water, and the organic layer was distilled off under reduced pressure to precipitate white crystals. After dispersion washing with hexane, drying was performed to obtain 95.2 g of white crystals of the exemplary compound (A-8).

[0143] Will exemplify compound (A-8) 1 H-NMR spectrum (solvent: CDCl 3 ) is shown in figure 2 .

Embodiment 3

[0145] Synthesis of Exemplary Compound (A-6)

[0146] The exemplified compound (A-6) was synthesized by the following synthetic route.

[0147]

[0148] To 150 mL of acrylic acid cooled to 5° C., 50 mL of concentrated sulfuric acid was slowly added dropwise while maintaining the temperature in the system at 15° C. or lower. After adding 31.4 g of DHA-Me and 13.6 g of glyoxylic acid hydrate and stirring at 40°C for 5 hours, the inside of the system was cooled to 10°C. The solution in the system was added while stirring ice-cooled water, and extracted with 500 mL of ethyl acetate. After washing the extract with sodium bicarbonate water and water in this order, the solvent was distilled off. The oily substance obtained was purified by column chromatography using a mixed solvent of hexane / ethyl acetate to obtain 32.2 g of an oily substance of Exemplified Compound (A-6).

[0149] Will exemplify compound (A-6) 1 H-NMR spectrum (solvent: CDCl 3 ) is shown in image 3 .

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Abstract

Provided are: a method for producing a 12-carboxydehydroabietic acid derivative which is capable of forming a polymer that has a main skeleton derived from a plant-origin compound; and a dehydroabietic acid derivative which is used in the method for producing a 12-carboxydehydroabietic acid derivative. A 12-carboxydehydroabietic acid derivative is produced by oxidizing or decarbonating a dehydroabietic acid derivative that is represented by general formula (I). (In general formula (I), R1 represents a hydrogen atom, an optionally substituted aryl group or an optionally substituted alkyl group having 1-10 carbon atoms; R2 represents a hydrogen atom or an optionally substituted alkyl group having 1-10 carbon atoms; and X represents a carbonyl group, a hydroxymethylene group or an acyloxymethylene group.)

Description

technical field [0001] The present invention relates to a dehydroabietic acid derivative, a method for producing the same, and a method for producing a 12-carboxydehydroabietic acid derivative. Background technique [0002] In recent years, depetroleumization of resources has been studied from the viewpoint of global environmental protection, focusing on various natural resources. Even in the field of plastics, depetroleumization is being pursued, and polylactic acid, which uses lactic acid obtained by fermentation of glucose as a raw material, is widely used in packaging materials and the like. Polylactic acid is excellent in transparency but low in heat resistance, so its application to molded articles obtained by injection molding or the like has been limited to limited uses that are not exposed to high temperatures. [0003] In addition, as a component derived from a natural product (preferably a plant), there is rosin which can be collected from pine resin or the like....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/757C07C51/38C07C63/49C07C67/31C07C69/753
CPCC07C69/757C07C2103/26C07C51/38C07C67/31C07C2603/26C07C63/49
Inventor 上平茂生佐藤幸藏
Owner FUJIFILM CORP
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