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Aromatic diether dicarboxylic acid and preparation method thereof

An aromatic and dicarboxylic acid technology, which is applied in the preparation of carboxylic acid nitrile, nitrile preparation, chemical instruments and methods, etc., can solve the problems of tight supply, high content of p-carboxybenzaldehyde, etc., and achieve increased yield, effective collision probability, and The effect of alleviating the tight supply

Inactive Publication Date: 2019-09-06
珠海派锐尔新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Patent CN 103772191 B discloses a preparation method of terephthalic acid, which mainly solves the problem in the prior art that the content of p-carboxybenzaldehyde in terephthalic acid produced by oxidation of p-xylene is too high, and can be used for terephthalic acid Industrial production of formic acid
But these are the improvement and optimization of existing monomer synthesis methods rather than the synthesis of a new type of excellent dicarboxylic acid monomer to improve or even solve the problem of tight monomer supply

Method used

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  • Aromatic diether dicarboxylic acid and preparation method thereof
  • Aromatic diether dicarboxylic acid and preparation method thereof
  • Aromatic diether dicarboxylic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) Synthesis of nitrile compounds

[0034] Under the protection of nitrogen at room temperature, add 45.6g of bisphenol A (0.2mol) and 41.4g of finely ground anhydrous K 2 CO 3 (0.3mol), 60.5g p-chlorobenzonitrile (0.44mol) and 200ml NMP, 50ml toluene, heat up to 150°C and reflux to divide the water, wait for the anhydrous to come out and finish the water separation, let off the water and most of the toluene after the water separation is completed, Stir and heat up to 180°C. After about 5 hours of reaction, the reaction is over. After cooling, pour the product into 200ml of high-speed stirring water, filter, wash the solid with water, and dry to obtain bisphenol A diether dicarbonitrile.

[0035] The result of NMR analysis of the product was 1H-NMR (DMSO-d6 (deuterated dimethyl sulfoxide), δ, ppm) 7.79 (4H, d), 7.29 (4H, d), 1.65 (6H, d).

[0036] The resulting bisphenol A diether dinitrile has a melting point of 124-125° C. as measured by a hot stage polarizing micr...

Embodiment 2

[0041] (1) Synthesis of nitrile compounds

[0042] Under the protection of nitrogen at room temperature, add 74.484g biphenol (0.4mol) and 52.95g finely ground anhydrous sodium carbonate (0.5mol ), 121g p-chlorobenzonitrile (0.88mol) and 800ml sulfolane, 100ml toluene, heat up to 160°C to reflux for water separation, wait for anhydrous to come out and finish water separation, let off water and most of toluene after water separation, stir and heat up to 200 ℃, after about 3 hours of reaction, the reaction is over. After cooling, pour the product into 400ml of high-speed stirred water, filter, wash the solid with water, and dry to obtain biphenol-type diether dicarbonitrile.

[0043] The resulting biphenol type diether dinitrile has a melting point of 238-240° C. as measured by a hot stage polarizing microscope.

[0044] (2) Synthesis of acid compounds

[0045] Add 21.5g of biphenol-type diether dinitrile (0.05mol), 28g of KOH (0.5mol), 200ml of DMSO and 50ml of water into a 5...

Embodiment 3

[0048] (1) Synthesis of nitrile compounds

[0049] Under the protection of nitrogen at room temperature, add 75.27g 6,6'-dihydroxy-2,2'-bipyridine (0.4mol) to a 1000ml four-neck flask equipped with mechanical stirring, water separator, nitrogen inlet and thermometer, 52.95 g finely ground anhydrous sodium carbonate (0.5mol), 121g p-chlorobenzonitrile (0.88mol) and 800ml sulfolane, 100ml toluene, heat up to 160°C and reflux to divide the water. Remove water and most of the toluene, stir and heat up to 200°C, react for about 3 hours, and the reaction is over. After cooling, pour the product into 400ml of high-speed stirring water, filter, wash the solid, and dry to obtain 6,6'-dihydroxy -2,2'-Bipyridyl Diether Dicarbonitrile.

[0050]The obtained 6,6'-dihydroxy-2,2'-bipyridyl diether dinitrile has a melting point of 262-265°C as measured by a hot stage polarizing microscope.

[0051] (2) Synthesis of acid compounds

[0052] Add 21.6g 6,6'-dihydroxy-2,2'-bipyridine diphenol ty...

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Abstract

Disclosed is an aromatic diether dicarboxylic acid. The aromatic diether dicarboxylic acid accords with the general formula which is shown in the description, wherein the R group is selected from oneof three groups which are shown in the description, a heterocyclic aromatic group and a polycyclic aromatic group and the n is a positive integer. The heterocyclic aromatic group refers to an aromaticgroup having carbon atoms and at least one heterocyclic atom which constitute a ring. The polycyclic aromatic group refers to an aromatic group in which two or more benzene rings are connected in a condensed ring form. The invention also discloses applications of the aromatic diether dicarboxylic acid as a monomer raw material in the fields of coating, adhesives, macromolecule materials, especially special engineering plastics. In a polymerization reaction, the introduction of an ether bond in the monomer, the effective collision probability of a reaction group is increased, the utilization rate of the monomer is increased, the yield of the polymer is improved, and a feasible solution is provided for the problem of tight supply of the dicarboxylic acid monomer.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to an aromatic diether dicarboxylic acid and a preparation method thereof. Background technique [0002] Aromatic dicarboxylic acid is the main organic synthesis intermediate, which can undergo reactions such as salt formation, dehydration, hydrogenation, halogenation, and acylation. It is used in coatings, polyester resins, unsaturated polyester resins, special fibers, thermal adhesives, It has a wide range of uses in printing ink, coordination polymer supramolecular materials, synthesis of liquid crystal products, polyester fiber dyeing and modification, and resin plasticization. [0003] In recent years, with the advancement of science and technology, the people's demand for materials has become more and more diverse. Many materials originally used in the military field such as polyamide (PA), thermotropic liquid crystal polymer (TLCP), Kepler fiber and other special...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/54C07C51/08C07C65/24C07D213/643
CPCC07C65/24C07C255/54C07D213/643
Inventor 王贤文黄文刚谭麟饶先花龚维胡三友
Owner 珠海派锐尔新材料有限公司
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