Method for preparing bisphenol compound antioxidant product by using organic acid catalyst

An organic acid catalyst and compound technology, which is applied in the preparation of organic compounds, organic compound/hydride/coordination complex catalysts, organic chemistry, etc. The production process is complex and other problems, so as to protect the environment and human health, facilitate the production and operation process, and simplify the production and operation process.

Active Publication Date: 2010-05-12
溧阳常大技术转移中心有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its weak point is that the production process is complicated, and the equipment investment is large; the price of methylal raw materials is expensive, and the production cost is high; the danger when using methylal raw materials is very large, and the industrialized production is difficult; when using solid acid catalysts, 2- The conversion rate of tert-butyl-4-methylphenol raw material and the selectivity of products are far inferior to the homogeneous water emulsification system with liquid acid as a catalyst, and the product contains 2-tert-butyl-4-methylphenol, which is difficult to refine and purify
Therefore, this technical method cannot realize industrialized production so far
[0010] CN101092334A discloses taking formaldehyde aqueous solution and 2-tert-butyl-4-methylphenol as raw materials, sulfuric acid catalyst, adding aromatic hydrocarbon solvent and surfactant to prepare 2,2'-methylenebis(4-methyl-6- tert-butylphenol) method, the reaction product is neutralized, washed, solvent distilled, and crystallized to obtain 2,2'-methylene bis(4-methyl-6-tert-butylphenol) product. Its shortcomings A large amount of aromatic hydrocarbon solvent is required in the reaction, even if it is recycled, it will still bring poison to the operating environment; the process is complicated, the investment in equipment is large; a large amount of sewage is generated in the production.
Its disadvantage is that the conversion rate of raw materials is reduced and the yield of final products is reduced; a large amount of industrial waste water is produced, which causes very serious harm to the environment
Its disadvantage is that the remaining reaction mother liquor cannot be recycled, and if it is discharged, a large amount of sewage will be generated in production
Its disadvantage is that a large amount of organic solvent is required in the reaction, even if it is recycled, the volatile aliphatic hydrocarbon solvent will still have a large consumption; the production process is more complicated, and the equipment investment is large; a large amount of sewage is still produced in the production
[0016] Due to the oxidizing properties of sulfuric acid, the raw materials and products of alkylphenols will be easily oxidized, and as a result, the appearance of the obtained bisphenol compounds is yellowish.

Method used

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  • Method for preparing bisphenol compound antioxidant product by using organic acid catalyst
  • Method for preparing bisphenol compound antioxidant product by using organic acid catalyst
  • Method for preparing bisphenol compound antioxidant product by using organic acid catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] In a WHFSK type 2000mL stainless steel reaction kettle with a magnetic stirrer, 300 grams of 2-tert-butyl-4-methylphenol, 1000 grams of water, 30 grams of paraformaldehyde, and 30 grams of 1# liquid organic acid catalyst were successively added. The air in the reactor was replaced with nitrogen. Turn on the heating power supply to slowly heat up the material in the kettle. Stir while heating. Adjust the number of rotations to 150-160 rpm, and when the temperature of the reaction mixture rises to 83-86° C., keep the reaction for 5.0 hours. After the reaction, cool down, filter, and collect the obtained filtrate as the reaction mother liquor for use. The filter cake was washed with 50-80% ethanol aqueous solution to obtain 309.0 g of 2,2'-methylenebis(4-methyl-6-tert-butylphenol) white crystal product with a melting point of 128.3-130.8°C.

Embodiment 2

[0060] In a WHFSK type 2000mL stainless steel reaction kettle with a magnetic stirrer, 300 grams of 2-tert-butyl-4-methylphenol, 1200 grams of water, and 28 grams of paraformaldehyde were successively added. 35 grams of 1# liquid organic acid catalyst replace the air in the reactor with nitrogen. Turn on the heating power supply to slowly heat up the material in the kettle. Stir while heating. Adjust the number of revolutions to 150-160 revs / min, and when the temperature of the reaction mixture rises to 83-86° C., keep the reaction for 4.5 hours. After the reaction, cool down, filter, and collect the obtained filtrate as the reaction mother liquor for use. The filter cake was washed with 50-80% aqueous ethanol to obtain 305.5 g of 2,2'-methylenebis(4-methyl-6-tert-butylphenol) white crystal product with a melting point of 128.5-131.0°C.

Embodiment 3

[0062] In a WHFSK type 2000mL stainless steel reaction kettle with a magnetic stirrer, 300 grams of 2-tert-butyl-4-methylphenol, 1100 grams of water, and 29 grams of paraformaldehyde were successively added. 40 grams of 2# liquid organic acid catalyst, replace the air in the reactor with nitrogen. Turn on the heating power supply to slowly heat up the material in the kettle. Stir while heating. Adjust the number of rotations to 150-160 rpm, and when the temperature of the reaction mixture rises to 83-85° C., keep the reaction for 5.5 hours. After the reaction, cool down, filter, and collect the obtained filtrate as the reaction mother liquor for use. The filter cake was washed with 50-80% ethanol aqueous solution to obtain 306.1 g of 2,2'-methylenebis(4-methyl-6-tert-butylphenol) white crystal product with a melting point of 129.1-130.5°C.

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Abstract

The invention discloses a method for preparing a bisphenol compound antioxidant product by using an organic acid catalyst. A closed reactor is adopted, water is used as reaction solvent, a liquid organic acid catalyst is selected as a catalyst, and the bisphenol compound antioxidant product is generated through the condensation reaction of dialkyl phenol and aliphatic aldehyde. The liquid organicacid catalyst is one or a mixture of more of long-chain alkyl benzene sulfonic acid, long-chain dialkyl benzene sulfonic acid, long-chain alkyl diphenyl ether disulfonic acid and long-chain dialkyl diphenyl ether disulfonic acid and aliphatic hydrocarbon of C6 to C10 or aromatic hydrocarbon of C6 to C8 in a mass ratio of 1: 0.1-1.0. The dosage of the liquid organic acid catalyst is 7 to 30 percent by mass of dialkyl phenol; the mass ratio of the water to the dialkyl phenol is 2-5:1; and the molar ratio of the aliphatic aldehyde to the dialkyl phenol is 0.45-0.60: 1. The reaction pressure is 0to 0.1MPa, the reaction temperature is 60 to 95 DEG C, and the reaction time is 4 to 7 hours. The raw material variety used by the method is reduced, and the production efficiency is improved; and the method avoids using sulfuric acid and hydrochloric acid with stronger corrosion on the equipment.

Description

technical field [0001] The present invention relates to a kind of method for preparing bisphenol compound antioxidant product with organic acid catalyst, and bisphenol compound refers to following formula (I): [0002] [0003] Where: R 1 =C 1 ~C 5 Straight chain alkyl or branched alkyl; [0004] R 2 =C 1 ~C 5 Straight chain alkyl or branched alkyl; [0005] R 3 = H or CH 3 . Background technique [0006] The above formula (I) bisphenol compound antioxidant product is mainly used in synthetic rubber, polyolefin plastics, engineering plastics and other polymer materials, as well as antioxidants for oil products such as lubricating oil and fuel oil; it is also a bisphenol monoacrylate The main raw material of antioxidants. [0007] In the prior art, this bisphenol compound adopts aliphatic aldehyde and dialkylphenol represented by formula (II) as raw materials, and uses water as a reaction solvent, and contains anionic surfactant and an aqueous emulsion formed by...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/16C07C37/20B01J31/04
Inventor 杜飞刘涛明徐婷婷耿旺常美荣
Owner 溧阳常大技术转移中心有限公司
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