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Method for continuous synthesis of β-ionone by micro-chemical technology

A technology for ionone and pseudo-ionone, which is applied in the field of pseudo-ionone cyclization to synthesize beta-ionone, can solve the problems of small application potential, reduced reaction selectivity and yield, complicated operation, etc., and saves low-temperature energy consumption. , the effect of reducing costs

Active Publication Date: 2018-12-14
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this method can show better results in laboratory tests, it will have the following disadvantages in large-scale production: (1) the operation of adding dry ice is complicated, which increases the production cost and difficulty; (2) in the process of cyclization The heat of reaction should be removed quickly, otherwise the reaction selectivity and yield will be greatly reduced
Although this method can directly obtain the β-ionone product from α-ring citral, it does not need to overcome the strong exothermic cyclization reaction catalyzed by sulfuric acid, but the synthetic process of α-ring citral is complicated, and it is necessary to use citral with a primary or Secondary amines protect the aldehyde group, cyclization at low temperature in the presence of acid, hydrolytic deamination to obtain cyclic citral, or ozone oxidation of ionone to obtain cyclic citral, so the application potential is small

Method used

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  • Method for continuous synthesis of β-ionone by micro-chemical technology
  • Method for continuous synthesis of β-ionone by micro-chemical technology
  • Method for continuous synthesis of β-ionone by micro-chemical technology

Examples

Experimental program
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Effect test

Embodiment 1

[0023]Put the mixture of dichloromethane / pseudo-ionone with a volume ratio of 1 / 1, and 95-98wt% concentrated sulfuric acid at the flow rates of 2.2mL / min and 1.7mL / min, respectively, and simultaneously use a plunger pump to input the integrated In the microreactor 1 of the temperature control device, the channel volume of the microreactor 1 is 0.283mL, the reaction temperature at the front end of the reactor 1 is controlled at 20°C, and the temperature at the rear end of the reactor 1 is controlled at 60°C. The channel structure of the channel of the microreactor is a fish raft structure. The rear end of microreactor 1 introduces microreactor 2 to introduce quenching water to quench the reaction, thereby obtaining the reaction mixture by controlling the reaction residence time. The volume flow of quenching water and the volume flow of sulfuric acid are controlled at a ratio greater than 3:1. within range. Connect the effluent for 3.5 minutes to obtain a milky purple-red liqui...

Embodiment 2

[0025] Put the mixture of dichloromethane / pseudo-ionone with a volume ratio of 1 / 1, and 95-98wt% concentrated sulfuric acid at the flow rate of 4.3mL / min and 2.7mL / min, respectively, and simultaneously use the plunger pump to input the integrated In the microreactor 1 of the temperature control device, the channel volume of the microreactor 1 is 0.283mL, the reaction temperature at the front end of the reactor 1 is controlled at 20°C, and the temperature at the rear end of the reactor 1 is controlled at 60°C. The channel structure of the channel of the microreactor is a fish raft structure. The back end of the microreactor 1 introduces a T-shaped micro-mixer with a diameter of 1.2 mm, which is used to introduce quenching water to quench the reaction, so that the reaction mixture is obtained by controlling the reaction residence time. The volume flow rate of the quenching water and the volume flow rate of sulfuric acid Control in the range greater than 3:1. The effluent was co...

Embodiment 3

[0027] Put the mixture of dichloromethane / pseudo-ionone with a volume ratio of 1:1, and 95-98wt% concentrated sulfuric acid at the flow rate of 10mL / min and 5.6mL / min, respectively, and simultaneously use the plunger pump to input the integrated temperature In the microreactor 1 of the control device, the channel volume of the microreactor 1 is 0.283mL, the reaction temperature at the front end of the reactor 1 is controlled at 20°C, and the temperature at the rear end of the reactor 1 is controlled at 50°C. The channel structure of the channel of the microreactor is a comb structure. The rear end of microreactor 1 introduces microreactor 2 to introduce quenching water to quench the reaction, thereby obtaining the reaction mixture by controlling the reaction residence time. The volume flow of quenching water and the volume flow of sulfuric acid are controlled at a ratio greater than 3:1. within range. Connect the effluent for 1.05 min to obtain a milky purple-red liquid, add ...

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Abstract

The invention relates to a method for continuously synthesizing β-ionone by applying micro-chemical technology to pseudo-ionone. The method comprises: passing solvent-diluted pseudo-ionone and concentrated sulfuric acid continuously through a micro-reactor 1 integrating micro-reaction and micro-heat exchange, and reacting and exchanging heat in the channel of the micro-reactor to generate β-ionone product. The reaction mixture material is an acid-in-oil microemulsion system, and the microemulsion flows through a microreactor 2 integrating micro-reaction and micro-heat exchange, and dilutes the microemulsion with a certain volume ratio of ice water for post-processing in the subsequent section. The invention precisely controls the reaction parameters through the microchannel technology, and the yield of β-ionone can reach 80-85%.

Description

technical field [0001] The invention relates to a method for synthesizing beta-ionone by cyclization of pseudoionone, in particular to a method for continuously producing beta-ionone by utilizing microchemical technology. Background technique [0002] Industrial synthesis of carotene, carotenoids, vitamin A and their derivatives generally needs to be synthesized from existing available chemicals. As an intermediate in the synthesis of vitamin A and its derivatives, ionone connects petrochemical products and daily chemical products. Starting from the petrochemical product isobutene, citral can be synthesized through a series of reactions including Prins reaction, hydroisomerization reaction, oxidative dehydrogenation reaction and acid-catalyzed condensation-cracking-remake, and then citral and acetone undergo Claisen- The intermediate pseudoionone is obtained by Schmidt condensation reaction, and the pseudoionone undergoes cyclization reaction in acidic medium to generate io...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/21C07C45/67
CPCC07C45/67C07C49/21
Inventor 陈光文张博宇周峰
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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