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Method for preparing alkane carboxylic acid by increasing alkane carbon chains

An alkane carboxylic acid and carbon chain technology, applied in the field of alkane carboxylic acid synthesis, can solve problems such as being unsuitable for industrial production and harsh operation requirements.

Inactive Publication Date: 2021-06-08
北京岳达生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The purpose of the present invention is to overcome the shortcomings of the existing method for increasing the carbon chain length, such as strict requirements on reagents, harsh operation requirements, and unsuitability for industrial production, thereby proposing a method to increase the number of existing alkyl carboxylic acids by 5 or 6 Carbon is simple and easy to operate, a method more suitable for industrial production

Method used

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  • Method for preparing alkane carboxylic acid by increasing alkane carbon chains
  • Method for preparing alkane carboxylic acid by increasing alkane carbon chains
  • Method for preparing alkane carboxylic acid by increasing alkane carbon chains

Examples

Experimental program
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Effect test

Embodiment 1

[0045] Embodiment 1 8-Methyl nonanoic acid synthesis operation

[0046] 8-Methylnonanoic acid

[0047] Add 78.5g cyclohexanone, 83.6g morpholine, catalyzer p-toluenesulfonic acid (TsOH) 1.0g, 200mL entrainer toluene in 500mL reaction flask, stir, heat and reflux to separate water to the calculated amount (14.4g), Then vacuum distillation reclaims toluene 200mL, obtains 170g 1-morpholine-1-cyclohexene crude product, and its infrared spectrogram is as follows figure 1 shown.

[0048]To the obtained 100.0g crude 1-morpholine-1-cyclohexene, add 300.0mL of chloroform to dilute, then add 121.7g of triethylamine, after cooling down to below 10°C, slowly drop in 127.3g of isobutyryl chloride, dropwise After that, the stirring reaction was continued for 3 hours. Then add 110.0mL of 30% w / w hydrochloric acid aqueous solution, heat and reflux for 2 hours and separate the liquid, separate the chloroform layer and the water layer, and separate the water layer after neutralization with p...

Embodiment 2

[0050] Example 2 7-methyl octanoic acid synthesis operation

[0051] 7-methyloctanoic acid

[0052] Add 84.1g of cyclopentanone, 87.1g of morpholine, 1.0g of catalyst p-toluenesulfonic acid, 200mL of entrainer toluene into a 500mL reaction flask, stir, heat and reflux until the water is separated to the calculated amount (18.1g), and then depressurize Recover toluene 200mL by distillation, obtain 163g 1-morpholine-1-cyclopentene crude product, its infrared spectrogram is as follows Figure 4 shown.

[0053] Add 500mL of chloroform to the obtained crude product of 1-morpholine-1-cyclopentene for dilution, then add 210.2g of triethylamine, after cooling down to below 10°C, slowly drop in 220.8g of isobutyryl chloride, and continue stirring React for 3 hours. Then add 110.0mL of 30% w / w hydrochloric acid aqueous solution, heat and reflux for 2 hours and separate the liquid, separate the chloroform layer and the water layer, and separate the water layer after neutralization wit...

Embodiment 3

[0055] Example 3 9-Methyldecanoic Acid Synthesis Operation

[0056] 9-methyldecanoic acid

[0057] According to the method in Example 1, add 300.0mL chloroform to dilute the obtained 100.0g 1-morpholine-1-cyclohexene crude product, add 121.7g triethylamine, after cooling to below 10°C, slowly drop into 144.1g isovaleryl chloride, after dripping, continue to stir and react for 3 hours. Then add 110.0mL of 30% hydrochloric acid aqueous solution, heat and reflux for 2 hours and then separate the layers, separate the chloroform layer and the water layer, and separate the water layer after neutralizing with potassium hydroxide, collect the mixture of triethylamine and morpholine, then dry and Fractional distillation recovers triethylamine and morpholine for later use. The chloroform layer was washed twice with water, dried and filtered over anhydrous sodium sulfate, and concentrated to obtain 65.5g crude product 2-(3-methylbutyryl)cyclohexanone compound, and its infrared spectrum...

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Abstract

The invention discloses a method for preparing alkane carboxylic acid by increasing alkane carbon chains. The method comprises the following steps: (1) carrying out Stork enamine alkylation on cyclopentanone or cyclohexanone and a secondary amine compound to generate a corresponding 1-position secondary amine substituted cyclopentene or cyclohexene crude product, namely Stork enamine; (2) carrying out electrophilic reagent reaction on the Stork enamine and acyl halide to form a 2-acyl cyclic ketone compound; and (3) carrying out ring opening on the 2-acyl cyclic ketone compound under the action of alkali to generate a carbonyl carboxylic acid compound, and carrying out a Wolff-Huang Minglong reduction reaction on the carbonyl carboxylic acid compound to obtain the corresponding alkane carboxylic acid. According to the method disclosed by the invention, cyclopentanone or cyclohexanone can be flexibly selected to meet the requirement of increasing different carbon numbers according to the required carbon number and different sources of target carburant alkane carboxylic acid or corresponding acyl halide. The method has the advantages of simple reaction process and no complex operation difficulty, and is suitable for industrial mass production.

Description

technical field [0001] The invention relates to a method for synthesizing alkane carboxylic acid, in particular to a method for preparing alkane carboxylic acid by increasing the carbon chain of alkane, and the invention belongs to the technical field of chemical industry. Background technique [0002] In organic synthesis, the construction of carbon skeleton is an extremely important step, which involves the growth of carbon chains. There are many carbon chain growth reactions in organic chemistry, and the applicable occasions are different. The common carbon chain growth methods have the following methods: [0003] The use of organometallic compounds to grow carbon chains is common: Grignard reagents undergo nucleophilic addition reactions with aldehydes, ketones, esters, and alkylene oxides to form corresponding alcohols, and then undergo a series of reactions to obtain corresponding carboxylic acids. Reagents react with carbon dioxide to prepare carboxylic acids with on...

Claims

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Application Information

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IPC IPC(8): C07C51/31C07C59/185C07C51/377C07C57/03C07C59/76C07C53/126
CPCC07D295/033C07D295/023C07C45/455C07C51/31C07C51/377C07C2601/08C07C2601/14
Inventor 张天毛羽
Owner 北京岳达生物科技有限公司
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