Technological method for synthesizing optical pure L-/D-lactide by using biomass organic guanidine catalyst method

一种丙交酯、有机胍的技术，应用在光学纯单体领域，能够解决不容易再生、环境污染、金属锡催化剂易污染等问题，达到操作简便、工艺流程简化、易于工业化实施的效果

Active Publication Date: 2013-07-10
JINDAN BIOLOGICAL NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to solve the existing problems in the synthesis of commercialized L- / D-lactide that the metal tin catalyst is easy to pollute the product, is not easy to regenerate, and may cause pollution to the environment, and provides a kind of biomass organic guanidine catalytic synthesis Process method of optically pure L- / D-lactide

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] ①Put 100g of L-lactic acid (mass content 90%) into the reactor, heat to 130°C under argon atmosphere and normal pressure, dehydrate for 4 hours, then slowly depressurize the reactor to 60torr and react at 130°C 8h. The lactic acid oligomer OLLA was obtained with a weight average molecular weight of 1500 Da.

[0015] ②Add catalyst biomimetic organic guanidine compound CR, control the mass ratio of catalyst CR to L-lactic acid oligomer to 1:100, control reaction temperature to 180°C, vacuum degree to 2torr, react for 1 hour, collect the evaporated white crude L- lactide.

[0016] ③The collected crude L-lactide was first washed with a 1% alkali (sodium hydroxide) solution, then washed with deionized water until neutral, and vacuum-dried at 20°C for 24 hours to obtain white needle-like L-lactide. Lactide, yield 35.5%, specific rotation [α] 25D=-276.

Embodiment 2

[0018] ①Put 100g of L-lactic acid (mass content 90%) into the reactor, heat to 170°C under argon atmosphere and normal pressure, dehydrate for 1 hour, then slowly depressurize the reactor to 30torr and react at 170°C 2h. The lactic acid oligomer OLLA was obtained with a weight average molecular weight of 600 Da.

[0019] ②Add the catalyst biomimetic organic guanidine compound CR, control the mass ratio of the catalyst to L-lactic acid oligomer to 1:10000, control the reaction temperature to 260°C, and the vacuum degree to 15torr, react for 4 hours, and collect the evaporated white crude L-propane lactide.

[0020] ③The collected crude L-lactide was first washed with a 10% alkali (sodium carbonate) solution, then washed with deionized water until neutral, and dried in vacuum at 40°C for 36 hours to obtain white needle-like L-lactide Ester, yield 40.3%, specific rotation [α]25D=-280.

Embodiment 3

[0022] ①Put 100g of L-lactic acid (mass content 90%) into the reactor, heat to 150°C under argon atmosphere and normal pressure, dehydrate for 2 hours, then slowly depressurize the reactor to 40torr and react at 150°C 4h. The lactic acid oligomer OLLA was obtained with a weight average molecular weight of 1100 Da.

[0023] ②Add the catalyst biomimetic organic guanidine compound CR, control the mass ratio of catalyst to L-lactic acid oligomer to 1:1000, control the reaction temperature to 200°C, vacuum degree to 10torr, react for 3 hours, and collect the evaporated white crude L-propane lactide.

[0024] ③Wash the collected crude L-lactide with an alkali (sodium bicarbonate) solution with a concentration of 8% first, then wash it with deionized water until it is neutral, and dry it in vacuum at 35°C for 30 hours to obtain white needle-like L-lactide Lactide, yield 45.8%, specific rotation [α] 25D=-277.

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Abstract

The invention relates to a technological method for synthesizing optical pure L- / D-lactide by using a biomass organic guanidine catalyst method. The technological method comprises the following step of: with biomass organic guanidine compound creatinine (CR) as a catalyst and L- / D-lactic acid (mass content of 90%) as a raw material, synthesizing the optical pure L- / D-lactide by using a reactive reduced pressure distillation catalysis method. The technological method has the advantages that the used catalyst is the biomass organic guanidine compound creatinine and free of toxicity, metal and cytotoxicity; the synthesized lactide is high in purity (the specific rotation [Alpha] 25D of the L-lactide ranges from minus 276 to minus 280, and the specific rotation [Alpha] 25D of the D-lactide is 280), and does not contain any metal; the use amount of the catalyst in the reaction process is low, the technological process is simplified as a process for rectifying and purifying a crude lactide product by using a conventional method is not used; and the technological method is simple and convenient to operate and easy for industrial implementation.

Description

technical field [0001] The invention belongs to the field of optically pure monomers for the synthesis of eco-friendly / biomedical degradable polylactic acid materials, specifically a process for synthesizing optically pure L- / D-lactide using biomass organic guanidine compound creatinine (CR) as a catalyst . Background technique [0002] Polylactic acid or polylactide (PLA) is a widely used eco-friendly material and biodegradable material, which can be used to prepare various medical materials, such as implantable hard tissue repair materials, surgical sutures, targeting and control release drug carriers, etc. In addition, polylactic acid can also be applied to the preparation of various biodegradable plastic products, such as films, fibers, packaging materials, etc. Commercial high-molecular-weight polylactic acid is generally prepared by catalytic ring-opening polymerization using lactide as a monomer. Therefore, the synthesis of lactide is of great significance for the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/12
CPCC07D319/12B01J31/0208B01J31/0241B01J31/0271B01J2231/34
Inventor 李弘张全兴成娜张天荣江伟黄伟潘丙才
Owner JINDAN BIOLOGICAL NEW MATERIAL CO LTD
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