Preparation method for 3, 3-dimethylbutyraldehyde

A technology of dimethylbutyraldehyde and dimethylbutyl, which is applied in the new preparation field, can solve the problems of high industrial cost, high reaction energy consumption, and high cost, and achieve high production safety, mild reaction conditions, and production process short effect

Inactive Publication Date: 2015-08-05
QINGDAO CHENGHUI SHUANGDA BIOLOGICAL TECH CO LTD
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0003] In the prior art, there are many preparation methods for 3,3-dimethylbutyraldehyde, such as some foreign preparation methods such as patent US4175204, which discloses the use of sodium bromide and allyl chloride, and the substituted allyl chloride is used in the catalyst In the presence of a certain amount of sodium bromide, it is oxidized to the corresponding aldehyde with N,N-dimethylsulfoxide; in the patent US5994593, it is disclosed that it is prepared by hydrolysis of 1,1-dichloro-3,3-dimethylbutane; US In 5905175, the preparation of 3,3-dimethylbutanal by oxidation of 1-chloro 3,3-dimethylbutane is disclosed; in the patent US6825384 and the World Intellectual Property Organization WO2005082825, the use of 3.3-dimethylbutanol is disclosed Oxidation to prepare 3,3-dimethylbutyraldehyde; in EP0391652 and EP0374952, 3,3-dimethylbutyraldehyde is obtained by 3,3-dimethylbutyraldehyde in methylene chloride solution with oxalyl chloride, dimethyl When sulfoxide and triethylamine exist, it is prepared by oxidation. This method is the well-known Swern oxidation method, which will produce a foul-smelling dimethyl sulfide by-product, which is not conducive to industrialization
[0004] In addition, there are currently many domestic patents publishing methods for preparing 3,3-dimethylbutyraldehyde, such as the use of 1-

Method used

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  • Preparation method for 3, 3-dimethylbutyraldehyde
  • Preparation method for 3, 3-dimethylbutyraldehyde
  • Preparation method for 3, 3-dimethylbutyraldehyde

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Experimental program
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Embodiment 1

[0022] The preparation method of 3,3-dimethylbutanal of the present invention, it specifically comprises the following steps:

[0023] Step 1. Put 100 kg of dichloromethane into the reaction kettle, turn on the stirring and cooling cycle, and when the temperature drops to -10°C--5°C, add 2.5 kg of ferric chloride, and add tert-butanol dropwise within 5 hours 60 kg, and then 45 kg of vinyl chloride gas was introduced within 3 hours, and after the ventilation was completed, it was kept at -5°C--2°C for 3 hours;

[0024] Step 2. After the reaction is over, pour 30 kg of deionized water into the reaction kettle, stir well, separate the organic layer, add 12 kg of sodium sulfate to dry, then concentrate and recover dichloromethane at 30°C-45°C until exhausted. Continue vacuum distillation, collect 60°C-64°C / 20mmHg fractions, and obtain 110.2 kg of colorless liquid 1-hydroxy-3,3-dimethylbutyl chloride;

[0025] Step 3. Put 100.2 kg of 1-hydroxy-3,3-dimethylbutyl chloride into the r...

Embodiment 2

[0027] The preparation method of 3,3-dimethylbutanal of the present invention, it specifically comprises the following steps:

[0028] Step 1. Put 200 kg of dichloromethane into the reaction kettle, turn on the stirring and cooling cycle, and when the temperature drops to -10°C--5°C, add 6 kg of aluminum trichloride, and add tert-butanol dropwise within 5 hours 122 kg, and then 105 kg of vinyl chloride gas was introduced within 3 hours, and after the ventilation was completed, it was kept at -5°C--2°C for 3 hours;

[0029] Step 2. After the reaction is over, pour 70 kg of deionized water into the reaction kettle, stir well, separate the organic layer, add 30 kg of sodium sulfate to dry, and concentrate and recover dichloromethane at 30°C-45°C until exhausted. Continue vacuum distillation, collect fractions at 60°C-64°C / 20mmHg, and obtain 224.2 kg of colorless liquid 1-hydroxy-3,3-dimethylbutyl chloride;

[0030] Step 3. Put 205.6 kg of 1-hydroxy-3,3-dimethylbutyl chloride int...

Embodiment 3

[0032] The preparation method of 3,3-dimethylbutanal of the present invention, it specifically comprises the following steps:

[0033] Step 1. Put 320 kg of dichloromethane into the reaction kettle, turn on the stirring and cooling cycle, and when the temperature drops to -10°C--5°C, add 6 kg of methanesulfonic acid, and dropwise add 200 kg of tert-butanol within 5 hours kg, and then 150 kg of vinyl chloride gas was introduced within 3 hours, and after the ventilation was completed, it was kept at -5°C--2°C for 3 hours;

[0034] Step 2. After the reaction is over, put 100 kg of deionized water into the reaction kettle, stir well, separate the organic layer, add 16 kg of sodium sulfate to dry, concentrate and recover dichloromethane at 30°C-45°C until exhausted, Continue vacuum distillation, collect fractions at 60°C-64°C / 20mmHg, and obtain 366.6 kg of colorless liquid 1-hydroxy-3,3-dimethylbutyl chloride;

[0035] Step 3. Put 326.6 kg of 1-hydroxy-3,3-dimethylbutyl chloride i...

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Abstract

The invention discloses a preparation method for 3, 3-dimethylbutyraldehyde. The method includes: taking tert-butyl alcohol and vinyl chloride as raw materials and dichloromethane as the reaction solvent to conduct catalytic synthesis of 1-hydroxy-3, 3-dimethyl butyl chloride, then under the action of a catalyst, controlling the temperature at 40DEG C-60DEG C, conducting hydrolysis disproportionation on 1-hydroxy-3, 3-dimethyl butyl chloride to prepare a hydrolysis disproportionation reaction mixture containing 3, 3-dimethylbutyraldehyde; and finally subjecting the hydrolysis disproportionation reaction mixture containing 3, 3-dimethylbutyraldehyde to rectification purification, thus obtaining 3, 3-dimethylbutyraldehyde. Compared with the prior art, the raw materials used by the method are low in price, the production cost can be reduced, the temperature needed by the reaction process is low, wherein the disproportionation temperature is 40DEG C-60DEG C, and compared with the 100DEG C-110DEG C disproportionation temperature in the prior art, the preparation method provided by the invention has the characteristics of milder reaction conditions, no need for high temperature, no special requirement for production equipment, high production safety, higher product purity, and yield up to over 97%.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a new preparation method of 3,3-dimethylbutyraldehyde. Background technique [0002] Neotame N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester is a high-intensity sweetener developed by NutraSweet Company in the United States. Flavoring agent, it has advantages such as high sweetness, low calorie, high stability, no cariogenicity, has huge market potential; And 3,3-dimethyl butyraldehyde is the important intermediate of synthetic neotame (disclosed in Patents US5480668 and US5510508), its market price is expensive, so it is necessary to find an economical and specific method for preparing this intermediate. [0003] In the prior art, there are many preparation methods for 3,3-dimethylbutyraldehyde, such as some foreign preparation methods such as patent US4175204, which discloses the use of sodium bromide and allyl chloride, and the sub...

Claims

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Application Information

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IPC IPC(8): C07C45/42C07C47/02
CPCC07C45/42C07C29/32C07C47/02C07C31/36
Inventor 胡俊峰刘速凌王刚于东海孔江
Owner QINGDAO CHENGHUI SHUANGDA BIOLOGICAL TECH CO LTD
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