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Method for preparing 2,2'-biphenyldicarboxylic acid

A biphenyl dicarboxylic acid, H2O2 technology, applied in the direction of oxidative preparation of carboxylic acid, chemical instruments and methods, physical/chemical process catalysts, etc., can solve the problems of post-processing burden increase, acid waste water generation, high production cost, etc. Effects of processing burden, less usage, and reduction of production cost

Inactive Publication Date: 2012-07-25
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above methods all have the following disadvantages: in the production process, the oxidation reaction needs to consume a large amount of H 2 o 2 And glacial acetic acid, not only the production cost is higher, but also the post-processing burden increases
In addition, in the post-treatment process, it needs to be acidified with concentrated HCl, which produces acidic wastewater and pollutes the environment.

Method used

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  • Method for preparing 2,2'-biphenyldicarboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add industrial phenanthrene (25mmol, content 95%) in the Erlenmeyer flask that 100mL has condenser tube, mass concentration is acetic acid (8ml) of 99%, Na 2 WO 4 (0.5mmol) and sulfosalicylic acid (2mmol), be heated to 80 ℃, slowly add mass concentration under the condition of stirring and be 30% H 2 o 2 20mL, the time of adding is 1h. Continue heating, and continue to react for 3 hours at 90-100°C under reflux conditions. After the reaction, cool and filter to obtain white crystal 2,2'-biphenyldicarboxylic acid with a yield of 71%, a melting point of 226-228°C, and a purity of >99%. Product structure by IR, 1 H NMR, 13 C NMR, elemental analysis for characterization. The analysis results are as follows:

[0033] IR (KBr tablet method, cm -1 ): 2996(OH), 2885, 1689(C=O), 1597(V C＝C ), 1579 (v C＝C ), 1475 (V C＝C ), 1455 (V C＝C ), 753 (γ ＝CH ).

[0034] 1 H NMR (DMSO-d 6 ,300MHz)δ H : 12.43(s, 2H, 2OH), 7.90(d,

[0035] 2H, J=7.5Hz, 2ArH), 7.56(t.

[00...

Embodiment 2

[0042] Add industrial phenanthrene (25mmol, content 95%) in the Erlenmeyer flask that 100mL has condenser tube, mass concentration is acetic acid (5ml) of 99%, K 2 WO 4 (0.5mmol) and oxalic acid (2mmol), heated to 80 ° C, slowly adding mass concentration of 30% H 2 o 2 20mL, the time of adding is 1h. Continue heating, and continue to react for 6 hours at 90-100°C under reflux conditions. After the reaction, cool and filter to obtain white crystal 2,2'-biphenyldicarboxylic acid with a yield of 74%, a melting point of 226-228°C, and a purity of >99%. Product structure by IR, 1 H NMR, 13 C NMR, elemental analysis for characterization. The analysis result is consistent with Example 1.

Embodiment 3

[0044] Add industrial phenanthrene (25mmol, content 95%), mass concentration is 80% acetic acid (6ml), mass concentration is 99% propionic acid (2ml) and phosphotungstic acid (0.05 mmol), heated to 70 ° C, slowly adding mass concentration under the condition of stirring is 30% H 2 o 2 25mL, the time to add is 1.5h. Continue heating, and continue to react for 4.5h at 90-100°C under reflux conditions. After the reaction, cool and filter to obtain white crystal 2,2'-biphenyldicarboxylic acid with a yield of 63%, a melting point of 225-228°C, and a purity of >99%. Product structure by IR, 1 H NMR, 13 C NMR, elemental analysis for characterization. The analysis result is consistent with Example 1.

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Abstract

The invention belongs to the field of preparation methods of aromatic series binary acids, and in particular relates to a method for synthesizing 2,2'-biphenyldicarboxylic acid by using phenanthrene as a starting material under an acid condition, and comprises the following steps in turn: (1) adding the phenanthrene, an acid solvent, a catalyst and a catalyst ligand into a reaction kettle; (2) adding H2O2 into the reaction kettle in the step (1) slowly at a temperature of between 30 and 100 DEG C; and (3) continuously refluxing at a temperature of between 80 and 110 DEG C and at normal pressure to obtain a target product, wherein the mass concentration of the H2O2 is between 30 and 50 percent. The method has the advantages of simple and readily-available raw material, mild reaction condition, short reaction time, high yield, safe process route, low cost, high purity of the target product, and good environmental protection performance.

Description

technical field [0001] The invention belongs to the field of preparation methods of aromatic dibasic acids, and in particular relates to a method for synthesizing 2,2'-biphenyldicarboxylic acid under acidic conditions using phenanthrene as a starting material. Background technique [0002] 2,2'-Biphenyl dicarboxylic acid is a white crystal with a melting point of 226-229°C, soluble in ethanol, acetone, benzene, ether and other organic solvents, slightly soluble in water, and capable of sublimation. Biphenyl dicarboxylic acid has the chemical reactivity of aromatic dibasic acids, and can generate acid anhydrides, esters, imides, amides, and oxychlorides. The compound has the characteristics of heat resistance, cold resistance, alkali resistance, hydrophobicity, weather resistance, radiation resistance, etc. It can be used as a modifier for resin raw materials and engineering plastics, coating modifiers, fiber modifiers, special In addition to plasticizers and pressure-sensit...

Claims

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Application Information

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IPC IPC(8): C07C63/331C07C51/31B01J31/04B01J31/02B01J23/30B01J23/04B01J21/08B01J27/188
Inventor 王敏宋志国
Owner BOHAI UNIV
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