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One-step method for synthesizing lactone type crown ether by lactone ring expansion

A technology of lactone and crown ether, which is applied in the field of organic synthesis, can solve the problems of no reports of alkylene oxide embedded in cyclic carboxylate, and achieve the effects of reduced energy consumption, high conversion rate and mild reaction conditions

Inactive Publication Date: 2008-05-28
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In our previous work, Al-Mg-based composite catalysts were used to catalyze the reaction of chain carboxylic acid esters such as alkylene oxide embedded in ethyl acetate (Xia Y M, Shen Y A, Fang Y, et al. One-step Production of Alkoxylated Ethyl Acetate with Narrow Adduct Distribution.J of Chem Technology and Biotechnology, 2006, 82 (1): 47-50), but there is no report of alkylene oxide embedded in cyclic carboxylate

Method used

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  • One-step method for synthesizing lactone type crown ether by lactone ring expansion
  • One-step method for synthesizing lactone type crown ether by lactone ring expansion

Examples

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Effect test

Embodiment 1

[0017] Example 1: Synthesis of 17-octyl-1,4,7,10,13-pentaoxaneheptadecan-14-one

[0018] Add 1mol of γ-laurolactone and Al-Mg based composite catalyst into the autoclave, and the amount of catalyst added is 1% of the total mass of reactants. After sealing the lid of the kettle, use N 2 Replace the gas in the kettle 3 times. After heating the reactant to 100-105°C, add 4 mol of ethylene oxide dropwise under 0.5-0.6 MPa while stirring. After the ethylene oxide was added dropwise, the reaction was maintained for another 30 minutes to end the reaction, and the catalyst was removed by filtration while it was hot. The conversion rate of γ-laurolactone reached 80.4%.

Embodiment 2

[0019] Example 2: Synthesis of 3,6-dimethyl-1,4,7-trioxocycloundecane-8-one

[0020] Add 1mol of γ-butyrolactone and Al-Mg based composite catalyst into the autoclave, and the amount of catalyst added is 0.5% of the total mass of reactants. After sealing the lid of the kettle, use N 2 Replace the gas in the kettle 3 times. After heating the reactant to 140-145°C, add 2 mol of propylene oxide dropwise under 0.3-0.4 MPa while stirring. After the propylene oxide was added dropwise, the reaction was maintained for another 30 minutes to end the reaction, and the catalyst was removed by filtration while it was hot. The conversion rate of γ-butyrolactone reached 85.4%.

Embodiment 3

[0021] Example 3: Synthesis of 3,6,9,12-tetraethyl-1,4,7,10,13-pentaoxaneheptadecan-14-one

[0022] Add 1 mol ε-caprolactone and Al-Mg based composite catalyst into the autoclave, and the amount of catalyst added is 3% of the total mass of reactants. After sealing the lid of the kettle, use N 2 Replace the gas in the kettle 3 times. After heating the reactant to 195-200°C, add 4 mol of butylene oxide dropwise under 2.9-3.0 MPa while stirring. After the addition of butylene oxide was completed dropwise, the reaction was maintained for 60 minutes, and then the reaction was terminated, and the catalyst was removed by filtration while it was hot. The conversion of ε-caprolactone reached 68.4%.

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Abstract

The invention relates to a method for synthesizing lactone crown ether from lactone via ring enlargement one-step method, belonging to organic synthesis technical field. The invention uses lactone starting agent, at 100-200DEG C and 0.3-3.0MPa, to catalyze alkylene oxide via Al-Mg based compound catalyst to enlarge the ring of lactone, to synthesize lactone crown ether via one-step. The invention has simple and quick process, high conversion rate, eliminated diluent, non waste discharge, and environment friend, which can significantly reduce the synthesis time, as one safe, effective and energy-saving technique.

Description

technical field [0001] The invention discloses a method for synthesizing a lactone-type crown ether in one step through a ring-expanding reaction of a lactone, which belongs to the technical field of organic synthesis. Specifically, using lactone as the initiator, under the conditions of 100-200 °C and 0.3-3.0 MPa, the Al-Mg based composite catalyst is used to catalyze the alkylene oxide to expand the ring of the lactone, and synthesize the lactone crown ether in one step. Methods. Background technique [0002] Lactone-type crown ethers mainly use the cyclization reaction of non-ring initiators, generally through the acylation cyclization reaction of dibasic acid halides and polyglycols or dibasic carboxylates and dihalogenated polyglycols. However, this type of reaction often needs to be carried out in a large amount of solvents to inhibit the linear polymerization of molecules, and the synthetic reagents are expensive, the process is cumbersome and time-consuming, and the...

Claims

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Application Information

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IPC IPC(8): C07D323/00C07D325/00
Inventor 方云夏咏梅赵权
Owner JIANGNAN UNIV