Method for synthesizing gamma-butyrolactone containing spiro 1, 3-indandione structure by using micro-channel reaction device

A microchannel reaction, indanedione technology, applied in chemical instruments and methods, chemical/physical/physical-chemical reactors, chemical/physical/physical-chemical processes, etc. Low efficiency and other problems, to achieve the effect of easy control of the reaction process, shortening the reaction time, and speeding up the reaction rate

Active Publication Date: 2020-06-05
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Purpose of the invention: the present invention aims at the deficiencies of the prior art, and provides a method for synthesizing gamma-butyrolactone containing a spirocyclic 1,3-indanedione structure by using a microchannel reaction device, so as to solve the reaction steps existing in the prior art cumbersome, long reaction time, difficult acid wastewater treatment, low reaction efficiency and other problems, without the use of strong acid and expensive metal catalysts, simple and efficient realization of γ-butyrolactone containing spiro ring 1,3-indanedione structure Synthesis

Method used

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  • Method for synthesizing gamma-butyrolactone containing spiro 1, 3-indandione structure by using micro-channel reaction device
  • Method for synthesizing gamma-butyrolactone containing spiro 1, 3-indandione structure by using micro-channel reaction device
  • Method for synthesizing gamma-butyrolactone containing spiro 1, 3-indandione structure by using micro-channel reaction device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] The molar ratio of 2-benzylidene indene-1,3-dione to cyclo(ethylene)isopropyl malonate is 1:1.5, and the concentration of 2-benzylidene indene-1,3-dione is 0.2mol / L; the molar weight of tetrabutyl ammonium iodide is 20% of 2-benzylidene indene-1,3-dione; the molar weight concentration of tetrabutyl ammonium iodide is 0.04mol / L; 30wt% peroxide The molar amount of the hydrogen solution is three times that of 2-benzylidene indene-1,3-dione, and the ratio of the mixed solution of 1,2-dichloroethane to γ-valerolactone is 1:1.

[0079] Prepare the mixed solution of 2-benzylidene indene-1,3-dione, cyclo(ethylene)isopropyl malonate, 1,2-dichloroethane and γ-valerolactone as solution A; The mixed solution of tetrabutylammonium iodide, 30wt% hydrogen peroxide solution and 1,2-dichloroethane and γ-valerolactone is configured as solution B, and then solution A and solution B are according to the flow volume ratio of 1:1 pumped into the microchannel reaction device, the flow rate ...

Embodiment 2

[0097] The molar ratio of 2-[(2-methylphenyl)methylene]-1H-indene-1,3(2H)-dione to cyclo(methylene)isopropyl malonate is 1:1.5, 2- The concentration of [(2-methylphenyl)methylene]-1H-indene-1,3(2H)-dione is 0.2mol / L; the molar weight of tetrabutylammonium iodide is 2-[(2 20% of -methylphenyl)methylene]-1H-indene-1,3(2H)-dione; the molar concentration of tetrabutylammonium iodide is 0.04mol / L; 30wt% aqueous hydrogen peroxide The molar amount of 2-[(2-methylphenyl)methylene]-1H-indene-1,3(2H)-dione is three times that of 2-[(2-methylphenyl)methylene]-1H-indene-1,3(2H)-dione, and 1,2-dichloroethane and γ-pentane The mixed solution ratio of ester is 1:1.

[0098] 2-[(2-Methylphenyl)methylene]-1H-indene-1,3(2H)-dione, cyclo(methylene)isopropyl malonate and 1,2-dichloroethane The mixed solution prepared with γ-valerolactone is designated as solution A; the mixed solution obtained by preparing tetrabutylammonium iodide, 30 wt% aqueous hydrogen peroxide and 1,2-dichloroethane and γ-...

Embodiment 3

[0100] The molar ratio of 2-[(2-bromophenyl)methylene]-1H-indene-1,3(2H)-dione to cyclo(ethylene)isopropyl malonate is 1:1.5, 2-[ The concentration of (2-bromophenyl)methylene]-1H-indene-1,3(2H)-dione is 0.2mol / L; the molar amount of tetrabutylammonium iodide is 2-[(2-bromo 20% of phenyl)methylene]-1H-indene-1,3(2H)-dione; the molar concentration of tetrabutylammonium iodide is 0.04mol / L; the molar quantity of 30wt% hydrogen peroxide aqueous solution 3 times that of 2-[(2-bromophenyl)methylene]-1H-indene-1,3(2H)-dione, a mixed solution of 1,2-dichloroethane and γ-valerolactone The ratio is 1:1.

[0101] 2-[(2-Bromophenyl)methylene]-1H-indene-1,3(2H)-dione, cyclo(methylene)isopropylmalonate and 1,2-dichloroethane were mixed with The mixed solution configuration of γ-valerolactone is denoted as solution A; Be solution B, then solution A and solution B are pumped in the microchannel reaction device according to the flow volume ratio of 1:1, and the flow rate is 2.5mL / min, ente...

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Abstract

The invention discloses a method for synthesizing gamma-butyrolactone containing a spiro 1, 3-indandione structure by using a micro-channel reaction device. The method comprises the following steps: (1) dissolving a 2-benzal-1,3-indandione compound and malonic acid cyclic (sub)isopropyl ester in an organic solvent to prepare a homogeneous solution A; (2) dissolving a catalyst and an oxidant in anorganic solvent to prepare a homogeneous solution B; (3) respectively pumping the homogeneous solution A and the homogeneous solution B into a micro-mixer in a micro-channel reaction device at the same time, mixing, and introducing into a micro-reactor to carry out reactions; and (4) collecting the effluent of the micro-reactor to obtain the product. Compared with the prior art, gamma-butyrolactone containing a spiro 1,3-indandione structure is prepared by taking the 2-benzal-1,3-indandione compound as the substrate for the first time, the method avoids the use of acidic raw materials and expensive metals, and the used non-metal catalyst also has an excellent catalytic performance.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for synthesizing gamma-butyrolactone containing a spiro-ring 1,3-indanedione structure by using a microchannel reaction device. Background technique [0002] γ-butyrolactone containing spirocyclic 1,3-indanedione structure is the key skeleton and important structural unit of a large number of natural products and physiologically active compounds, and has potential antitumor, antibacterial and growth regulation effects. Not only that, this type of compound is also widely used in the synthesis of dyes, pigments, and semiconductor materials. In addition, it can be used for fingerprint identification in forensic chemistry. The development of fast and efficient synthetic methods for such compounds is one of the important problems to be solved in organic synthesis methodology. [0003] There are generally two methods for the preparation of such γ-butyro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10B01J19/00
CPCC07D493/10B01J19/0093
Inventor 郭凯丁晓娟段金电张磊徐高晨朱宁方正李振江
Owner NANJING UNIV OF TECH
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