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Preparation method of 1-hydroxyl-2-alkanone

An alkanone and hydroxyl technology, which is applied in the field of preparation of 1-hydroxy-2-alkanone, can solve the problems of low selectivity, difficulty in preparation, and many by-products, and achieves high product selectivity and easy industrialization. The effect of large-scale production and simple process flow

Active Publication Date: 2020-06-23
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw material ketone suitable for this method is 1-phenyl-1-acetone compound, and the α-hydroxy ketone product with the hydroxyl at the end cannot be prepared by the α-hydroxylation method
Literature (Han Li, Food and Fermentation Industry, 2006, 32(10): 116-118) reported a method for preparing α-hydroxy ketones by oxidation of vicinal diols, using 2,3-butanediol as raw material, through the air oxidation method Or electrochemical oxidation method can prepare 3-hydroxy-2-butanone, but the selectivity is low, and there are many by-products, and this method is difficult to oxidize 1,2-butanediol to 1-hydroxy-2-butanone with high selectivity. 2-butanone, not suitable for large-scale continuous production
In summary, the methods described are difficult to be used in the preparation of α-hydroxy ketones with hydroxyl at the end of the alkyl chain, such as 1-hydroxy-2-alkanone

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Catalyst Z1 was prepared by co-precipitation method, using copper nitrate, ytterbium nitrate and aluminum nitrate as raw materials, and a mixture of potassium hydroxide and potassium bicarbonate as precipitant.

[0035] According to elemental analysis, the weight content of CuO in catalyst Z1 is 46.1%, Yb 2 o 3 The weight content is 44.6%, K 2 The weight content of O is 0.8%, Al 2 o 3 The weight content is 8.5%.

[0036]Weigh 10 ml of catalyst Z2, place it in a fixed-bed reactor with an inner diameter of 10 mm, and first reduce it in a hydrogen atmosphere at 250 °C for 5 hours. After the reduction is completed, switch to 1,2-propanediol as the raw material, use hydrogen as the diluent, and the molar ratio of the diluent to the raw material is 1, at a temperature of 250°C, a pressure of 0.1 MPa and a liquid hourly space velocity of 5 h -1 Under the conditions, the conversion reaction was carried out, the conversion rate of raw materials was 41.8%, the product select...

Embodiment 2

[0038] Catalyst Z2 was prepared by co-precipitation method, using copper nitrate, nickel nitrate and aluminum nitrate as raw materials, and a mixture of potassium hydroxide and potassium bicarbonate as precipitant.

[0039] Through element analysis, the weight content of CuO of catalyst Z2 is 49.8%, the weight content of NiO is 35.2%, K 2 The weight content of O is 2.9%, Al 2 o 3 The weight content is 12.1%.

[0040] Weigh 10 ml of catalyst Z2, place it in a fixed-bed reactor with an inner diameter of 10 mm, and first reduce it in a hydrogen atmosphere at 250 °C for 5 hours. After the reduction is completed, switch to 1,2-propanediol as the raw material, use water vapor as the diluent, and the molar ratio of the diluent to the raw material is 0.1, at a temperature of 300°C, a pressure of 0.2 MPa and a liquid hourly space velocity of 2 h -1 Under the conditions, the conversion reaction was carried out, the conversion rate of raw materials was 45.4%, the product selectivity o...

Embodiment 3

[0042] Catalyst Z3 was prepared by co-precipitation method, using copper nitrate, zinc nitrate and aluminum nitrate as raw materials, and a mixture of potassium hydroxide and potassium bicarbonate as precipitant.

[0043] Through element analysis, the weight content of CuO of catalyst Z3 is 40.2%, the weight content of ZnO is 43.1%, K 2 The weight content of O is 2.5%, Al 2 o 3 The weight content is 14.2%.

[0044] Weigh 10 ml of catalyst Z3, place it in a fixed-bed reactor with an inner diameter of 10 mm, and first reduce it in a hydrogen atmosphere at 250 °C for 5 hours. After the reduction is completed, switch to 1,2-propanediol as the raw material, use nitrogen as the diluent, and the molar ratio of the diluent to the raw material is 0.5, at a temperature of 200°C, a pressure of 0.2 MPa and a liquid hourly space velocity of 1 h -1 Under the conditions, the conversion reaction is carried out, the conversion rate of raw materials is 49.3%, the product selectivity of 1-hyd...

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Abstract

The invention discloses a preparation method of 1-hydroxyl-2-alkanone. According to the preparation method, dihydric alcohol is converted into 1-hydroxy-2-alkanone in the presence of a copper-based catalyst (a conversion step). The reaction conditions of the conversion step are as follows: the reaction temperature is 200-400 DEG C, the reaction pressure is 0.01-0.5 MPa, and the liquid hour space velocity is 0.1-10 h<-1>. The method has a high dihydric alcohol conversion rate and 1-hydroxyl-2-alkanone selectivity, and is easy for industrial implementation.

Description

technical field [0001] The invention relates to a method for preparing 1-hydroxyl-2-alkanone, more specifically, the invention relates to a method for preparing 1-hydroxyl-2-alkanone by selective dehydrogenation of 1,2-dioxanol. Background technique [0002] 1-Hydroxy-2-alkanone is an α-hydroxy ketone compound with two functional groups of hydroxyl and carbonyl. Hydroxyl can be converted into double bond, halogenated hydrocarbon, carbonyl, ester group and other groups through mild reaction, and carbonyl group can also be converted into hydroxyl, alkyl, amino and other groups through reaction. Therefore, α-hydroxyketone compounds can be used as raw materials for the preparation of various fine chemicals and pharmaceutical intermediates, and can also be used as photoinitiators in UV-curable coatings. [0003] α-Hydroxy ketones mainly include azoin condensation method, ketone α-hydroxylation method and vicinal diol selective oxidation method. CN103781752 discloses a method ...

Claims

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Application Information

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IPC IPC(8): C07C45/00C07C49/17B01J23/83B01J23/80B01J23/78B01J37/03
CPCC07C45/002B01J23/83B01J23/80B01J23/78B01J23/002B01J37/03B01J2523/00C07C49/17B01J2523/13B01J2523/17B01J2523/3787B01J2523/31B01J2523/27B01J2523/847Y02P20/584
Inventor 乔凯周峰马会霞翟庆铜张淑梅
Owner CHINA PETROLEUM & CHEM CORP