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Method for preparing ketone or carboxylic acid through catalytic oxidation of secondary alcohol or primary alcohol

A technology for catalytic oxidation and primary alcohol, which is applied in the preparation of carbonyl compounds by oxidation, organic chemical methods, and carbon-based compound preparation. It can solve the problems of numerous by-products, difficult recycling, environmental pollution, etc., and achieve environmental pollution and catalytic effects. Good, the effect of reducing the cost of use

Inactive Publication Date: 2019-11-22
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to provide a method for preparing ketones or carboxylic acids by catalytic oxidation of secondary alcohols or primary alcohols in order to overcome the defects of the above-mentioned prior art, so as to solve the serious environmental pollution caused by traditional alcohol oxidants, difficulties in recycling, and numerous by-products. Technical problem, is a green catalytic oxidation reaction method of alcohol

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] This embodiment is a synthesis method of phthalocyanine, that is, the synthesis of tetraamide group-substituted cobalt phthalocyanine. The method refers to the method in the literature of Rezaeifard, M, et al.Catal.Commun.2011, 12:761, and the specific method is : Add 13.8g4-carboxyphthalic anhydride, 4.2g cobalt chloride (CoCl2), 25g urea (ratio of the amount of substance: 4:1:20), 1.9g ammonium chloride and 4.2g ammonium molybdate Mix it evenly in a mortar, grind it thoroughly, then place it in a 500mL thick-walled three-neck flask, react at a constant temperature of 130°C to 140°C for 0.5h, then raise the temperature to 180°C for 0.5h, and then add an appropriate amount of urea, then Raise the temperature to 220°C to 230°C for 4 hours. The obtained solid was repeatedly washed with boiling water until the filtrate was colorless. Then wash with acetone and methanol three times respectively, and dry to obtain a blue-black solid which is tetraamide-substituted metal pht...

Embodiment 2

[0041] A kind of green catalytic oxidation reaction method of alcohol, the steps of this method are:

[0042] Add 10mL of benzonitrile, 1.0016g of cyclohexanol, 0.3224g of NHPI, and 0.5945g of phthalocyanine in sequence in a three-neck flask, then feed oxygen at 20mL / min under normal pressure, stir at a constant temperature of 100°C for 24h, and finally detect and analyze by GC , the yield of cyclohexanone was 73.17%.

[0043] Wherein the proportioning of used cyclohexanol and benzonitrile is calculated according to the molar volume ratio, namely cyclohexanol: benzonitrile is 1mol:1000mL; the addition of NHPI and phthalocyanine and the molar mass ratio calculation of cyclohexanone, namely NHPI: Phthalocyanine: cyclohexanol is 0.2:0.08:1; the oxygen flow rate is calculated as 2000mL / min per 1mol cyclohexanol.

[0044] Comparing Example 2 and Comparative Example 1, it is found that when the added amount of phthalocyanine is reduced, the yield of reactants will also drop signifi...

Embodiment 3

[0047] A kind of green catalytic oxidation reaction method of alcohol, the steps of this method are:

[0048] Add 10mL of acetonitrile, 1.0813g of benzyl alcohol, 0.3224g of NHPI, and 0.5945g of phthalocyanine into the three-necked flask in sequence, then feed oxygen at 20mL / min under normal pressure, stir at 80°C for 9h, and finally detect by GC and spot on the plate by TLC The final product was determined to be benzoic acid by the method, and the solvent acetonitrile was evaporated with a rotary vacuum evaporator, and the yield of benzoic acid was calculated to be 86.78%.

[0049] Wherein the proportioning of used benzyl alcohol and acetonitrile is calculated according to the molar volume ratio, i.e. benzyl alcohol: acetonitrile is 1mol:1000mL; 0.2:0.08:1; Oxygen flow is calculated as 2000mL / min per 1mol of benzyl alcohol.

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Abstract

The invention relates to a method for preparing ketone or carboxylic acid through catalytic oxidation of alcohol. The method specifically comprises the following steps: adding secondary alcohol or primary alcohol into a certain amount of organic solvent to serve as a raw material, forming an N-hydroxyphthalimide (NHPI)-phthalocyanine catalytic system and taking oxygen as an oxidant, and reacting for 9-36 hours at the reaction temperature of 60-120 DEG C under the condition of normal pressure to obtain the ketone or carboxylic acid with higher yield. Compared with the prior art, the method hasthe advantages of green and environment-friendly oxidant, cheap and easily-prepared catalyst, easiness in separation from the product, mild reaction conditions and the like, and is a green alcohol oxidation method.

Description

technical field [0001] The invention relates to the technical field of green chemical synthesis, in particular to a method for preparing ketones or carboxylic acids by catalytic oxidation of secondary alcohols or primary alcohols. Background technique [0002] The conversion from secondary or primary alcohols to ketones or carboxylic acids through certain chemical reactions is the most basic and important type of reaction in organic synthesis. The selective oxidation of alcohols has a wide range of applications in fine chemicals, pharmaceutical synthesis, flavors and fragrances, etc. The oxidants used in traditional alcohol oxidation are high-valent transition metal compounds and hypervalent iodine reagents, which cause serious environmental pollution. Molecular oxygen has attracted people's attention as an environmentally friendly green oxidant. However, the activation of molecular oxygen easily leads to over-oxidation of oxidation products to generate by-products such as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/235C07C45/39C07B41/08C07C49/403C07C49/78C07C47/02C07C49/76C07C63/06C07C53/124C07C53/126C07B41/06B01J31/22
CPCB01J31/183B01J2231/763B01J2531/025B01J2531/845C07B41/06C07B41/08C07C45/39C07C51/235C07C2601/14C07C49/403C07C49/78C07C47/02C07C49/76C07C63/06C07C53/124C07C53/126B01J31/006B01J31/0247B01J2540/442C07C45/38B01J2231/70C07C45/29C07C51/255
Inventor 孙小玲李飞叶玲君唐志林赵晋鑫李和华
Owner SHANGHAI INST OF TECH
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