Method for synthesizing polyethyleneglycol monomethyl ether metacrylic acid ester

A technology of polyethylene glycol monomethyl ether and methacrylate, which is applied in the field of synthesis of polyethylene glycol monomethyl ether methacrylate, can solve the problems of low esterification rate and Michael addition side reactions, which are difficult to avoid Polymerization and other problems, to achieve the effect of simple steps, increase the rate of esterification, avoid polymerization and other side reactions

Inactive Publication Date: 2008-10-22
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The preparation of polyethylene glycol monomethyl ether methacrylate in the currently disclosed technical literature mostly adopts the direct esterification method or transesterification method under acid catalysis, and its reactivity is low, so higher temperature and long reaction time must be adopted , it is difficult to avoid the polymerization reaction. Secondly, the use of an acid catalyst may also cause other side reactions, such as the Michael addition side reaction of the double bond of alcohol and methacrylic acid (ester), which eventually leads to a low esterification rate. The product is a mixture, which is difficult to be directly applied to the subsequent polymerization reaction, and because the properties of the raw material and the product are similar, it is difficult to separate and purify to obtain pure polyethylene glycol monomethyl ether methacrylate

Method used

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  • Method for synthesizing polyethyleneglycol monomethyl ether metacrylic acid ester
  • Method for synthesizing polyethyleneglycol monomethyl ether metacrylic acid ester
  • Method for synthesizing polyethyleneglycol monomethyl ether metacrylic acid ester

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Embodiment 1

[0028] The experimental instruments are the instruments routinely used in the laboratory. Reagents are commercially available chemically pure or analytically pure chemical reagents.

[0029] Raw material polyethylene glycol monomethyl ether (MPEG-400) 1 See attached for H NMR spectrum figure 1 , at δ~3.4ppm is the end of MPEG-OCH 3 proton peak, 3.7ppm for MPEG-OCH 2 CH 2 The proton peak of O-.

[0030] Using polyethylene glycol monomethyl ether and methyl methacrylate to synthesize the polyethylene glycol monomethyl ether methacrylic acid by transesterification under the condition of feeding air and in the presence of an alkali catalyst, a polymerization inhibitor and a reaction medium ester. Concrete preparation process is as follows:

[0031] (1) Add 60g polyethylene glycol monomethyl ether (M n =400, 0.15mol), 22.5g methyl methacrylate (0.225mol), 0.042g phenothiazine (0.2mmol), 0.036g lithium tert-butoxide (0.45mmol) and 40ml cyclohexane, start stirring, pass into ...

Embodiment 2

[0038] The experimental equipment and reagent requirements are the same as in Example 1. The specific synthesis process is as follows:

[0039] (1) Add 90g polyethylene glycol monomethyl ether (M n =600, 0.15mol), 30g methyl methacrylate (0.3mol), 0.042g phenothiazine (0.2mmol), 0.036g lithium tert-butoxide (0.45mmol) and 45ml cyclohexane, start stirring and feed air Raise the temperature and heat to reflux under certain conditions, and keep the total reflux for 10 minutes, then control the reflux ratio to 5:1~6:1;

[0040] (2) Add 0.018g of lithium tert-butoxide every 30 minutes to lower the temperature of the kettle to below 70°C, three times in total, add 0.021g of phenothiazine at the same time for the third time, and adjust the reflux ratio to 8:1 ~9:1.

[0041] (3) After 4 hours and 20 minutes of reactive distillation, cyclohexane and unreacted methyl methacrylate were distilled off under reduced pressure to obtain 104.1 g of a light yellow viscous liquid product.

...

Embodiment 3

[0045] The experimental equipment and reagent requirements are the same as in Example 1. The specific synthesis process is as follows:

[0046] (1) Add 65g polyethylene glycol monomethyl ether (M n =1000, 0.065mol), 30ml methyl methacrylate (0.28mol), 0.03g phenothiazine (0.15mmol), 0.028g lithium tert-butoxide (0.35mmol) and 45ml cyclohexane, start stirring and feed air (10-15mL / min) and heat up to reflux, keep the total reflux for 10min, and control the reflux ratio to 5:1~6:1;

[0047] (2) Add 0.014g lithium tert-butoxide after 1h, continue the reaction distillation for 1h, add 0.02g phenothiazine and 0.014g lithium tert-butoxide, and adjust the reflux ratio to 8:1~9:1;

[0048] (3) After co-reactive distillation for 3 hours and 15 minutes, cyclohexane and unreacted methyl methacrylate were distilled off under reduced pressure, and 71.2 g of light yellow semi-solid product was obtained by cooling.

[0049] During the reaction, add cyclohexane in due course to ensure that...

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Abstract

The invention discloses a method for synthesizing poly (ethylene glycol) methyl ether methacrylate. Methyl methacrylate and PGME are synthesized to generate the poly (ethylene glycol) methyl ether methacrylateby through the ester exchange reaction. The catalyst used in the ester exchange reaction is a base catalyst and has high catalytic activity; an inhibitive substance is added in the reaction system to avoid the polyreaction in the process of reaction and air is put into the reaction system; the reaction temperature is moderate and is between 80 and 85 DEG C; the reaction side product of methanol and a reaction medium form an azeotrope which is taken out of the reaction system, thereby ensuring that the reaction is done completely. The method quantificationally converts the PGME into the poly (ethylene glycol) methyl ether methacrylate, has esterification rate close to 100 percent, avoids the polyreaction and other side reactions, has simple steps and is suitable for the industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a method for synthesizing polyethylene glycol monomethyl ether methacrylate. technical background [0002] Polyethylene glycol monomethyl ether methacrylate has many important applications, such as: (1) As a macromer, it is used as a high-performance polycarboxylate water reducer with important application value in cement and concrete engineering Synthesis is the most important and main raw material for determining the performance of polycarboxylate superplasticizers. The degree of esterification during the synthesis of the macromonomer directly affects the performance of the final polycarboxylate superplasticizer product; (2) As a reactive nonionic emulsifier used in emulsion polymerization, it can make the obtained emulsion have very good mechanical stability and stability to metal salts, and can make the stability of the prepared emulsion not affected by pH changes,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/48
Inventor 梁晖卢江徐文烈
Owner SUN YAT SEN UNIV
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