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A kind of mixed metal catalyst for preparing tert-butyl hydroquinone and the preparation method of tert-butyl hydroquinone

A technology of tertiary butyl hydroquinone and tertiary butyl quinone, which is applied in the field of preparation of tertiary butyl hydroquinone, can solve the problems of high production cost, great environmental pressure, and small environmental pollution, and achieve Breakthrough in yield and selectivity, reduction in raw material costs, and reduction in side reactions

Active Publication Date: 2020-04-28
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] GB761613 discloses a method for preparing TBHQ using phosphoric acid or sulfuric acid as a catalyst in a toluene solvent; WO9716402 uses benzenesulfonic acid for alkylation in hydrated methanol. Although these technologies are relatively mature, the production cost is too high and the production process Pollution to the environment is serious, facing greater pressure on environmental protection
[0005] CN1583698A discloses the preparation method of TBHQ, take hydroquinone and tert-butanol as raw materials and synthesize TBHQ by dehydration and alkylation under acid catalysis, and utilize a small amount of reducing agents such as sodium sulfite, sodium bisulfite and zinc powder in water and acid to TBHQ is separated and purified, the yield of this method is low, the crude product contains about 50% TBHQ, and the content of by-product DTBHQ is high
[0007] CN105294403B discloses a preparation process of tert-butyl hydroquinone, which mainly uses hydroquinone and tert-butyl acetate as raw materials, reacts under the action of dilute sulfuric acid, and then recycles the filtrate sulfuric acid after the reaction, However, because it uses a large amount of sulfuric acid, it still causes serious pollution to the environment
[0008] Based on the current demand for tert-butyl hydroquinone at home and abroad, as well as the high cost and high pollution of existing related synthesis technologies, the contradiction between demand and production technology has been formed. Therefore, it is necessary to develop a low-cost, environmentally polluting The preparation method of tert-butylhydroquinone with small size, high synthesis efficiency and selectivity has become a technical problem to be solved urgently

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The preparation method of tert-butylhydroquinone-sample 1:

[0044] Mixed metal catalysts are : The main catalyst is CuCl 1.5g and AgCl 2.2g; the co-catalyst is NaCl 0.6g.

[0045] Preparation method of sample 1 :

[0046] Step 1): Take the solid powder of the main catalyst and the co-catalyst according to the aforementioned mass ratio, mix them uniformly and add them into the reactor, and add 15g of 2-tert-butylphenol and 85g of methanol into the reactor, Wherein, the mass ratio of the 2-tert-butylphenol to the organic solvent is 1:5.67; the capacity of the reactor is 200ml, and the material accounts for 2 / 3 of the capacity of the reactor after adding;

[0047] Step 2): Close the reaction kettle, after sealing, feed oxygen into the reaction kettle, keep the internal pressure of the reaction kettle at 1Mpa, raise the temperature of the reaction kettle to 30°C under magnetic stirring, and keep stirring The state of edge reaction 8h;

[0048] Step 3): After the rea...

Embodiment 2

[0052] The preparation method of tert-butyl hydroquinone-sample 2:

[0053] Mixed metal catalysts are : The main catalyst is CuCl 1.5g and MgCl 2 1.7g; cocatalyst is NaCl 0.6g.

[0054] Preparation method of sample 2 :

[0055] Step 1): Take the solid powder of the main catalyst and the co-catalyst according to the aforementioned mass ratio, mix them uniformly and add them into the reactor, and add 15g of 2-tert-butylphenol and 85g of methanol into the reactor, Wherein, the mass ratio of the 2-tert-butylphenol to the organic solvent is 1:5.67; the capacity of the reactor is 200ml, and the material accounts for 2 / 3 of the capacity of the reactor after adding;

[0056] Step 2): Close the reaction kettle, after sealing, feed oxygen into the reaction kettle, keep the internal pressure of the reaction kettle at 1Mpa, raise the temperature of the reaction kettle to 30°C under magnetic stirring, and keep stirring The state of edge reaction 8h;

[0057] Step 3): After the rea...

Embodiment 3

[0061] The preparation method of tert-butylhydroquinone-sample 3:

[0062] Mixed metal catalysts are : The main catalyst is CuCl 1.5g and AgCl 2.2g; the co-catalyst is KCl 0.6g.

[0063] Preparation method of sample 3 :

[0064] Step 1): Take the solid powder of the main catalyst and the co-catalyst according to the aforementioned mass ratio, mix them uniformly and add them into the reactor, and add 15g of 2-tert-butylphenol and 85g of methanol into the reactor, Wherein, the mass ratio of the 2-tert-butylphenol to the organic solvent is 1:5.67; the capacity of the reactor is 200ml, and the material accounts for 2 / 3 of the capacity of the reactor after adding;

[0065] Step 2): Close the reaction kettle, after sealing, feed oxygen into the reaction kettle, keep the internal pressure of the reaction kettle at 1Mpa, raise the temperature of the reaction kettle to 30°C under magnetic stirring, and keep stirring The state of edge reaction 8h;

[0066] Step 3): After the reac...

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Abstract

The present invention relates to a mixed metal catalyst for preparing tert-butylhydroquinone and a preparation method of tert-butylhydroquinone. The mixed metal catalyst for tert-butylhydroquinone ofthe present invention comprises a main catalyst and a cocatalyst, wherein the main catalyst comprises one or more of CuCl, CuBr, AgCl, AgBr, AgI, FeCl3, MgCl2, CrCl3, ZnCl2 and CdCl2; and the cocatalyst comprises one or a combination of more of NaCl, KCl, LiCl and CaCl2. The invention further provides a method for preparing tert-butylhydroquinone by using the catalyst. The method uses tert-butylphenol as a raw material, thereby greatly reducing the cost of raw materials. The catalysts in the reaction process can be recycled. By controlling oxidizing condition, the reaction yield and selectivity of tert-butylhydroquinone in the whole system are greatly improved, the content of a crude product of tert-butylhydroquinone in the preparation method of the invention is as high as 60-90%, and thereaction selectivity is 60-80%.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of tert-butylhydroquinone. Background technique [0002] Tert-butyl hydroquinone (TBHQ), also known as tert-butyl hydroquinone, is a fine chemical product, commonly used as an antioxidant in food and edible oils, and can prevent rancidity and deterioration of most oils and fats It is used to prolong the storage period of fat and oily food. Because of its antioxidant and antibacterial effects, it is also used as an additive in the pharmaceutical and feed industries. With the rapid development of my country's economy, China is becoming a major consumer of 2-tert-butyl hydroquinone in the world, with an annual consumption of more than 1,000 tons, most of which need to be imported from abroad. Become a promising fine chemical product. However, due to the high production cost of TBHQ, the application of this product in other fields is limited to a cert...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J27/122B01J27/138B01J27/132C07C39/08C07C37/00C07C50/04C07C46/08
Inventor 黄崇品王新承邱果李英霞朱吉钦
Owner BEIJING UNIV OF CHEM TECH
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