Nippon Shokubai Co., Ltd.

Tokumasa Ishida

Yasuhiro Shingai

Yukihiro Yoneda

Masahiro Uemura

Hajime Matsumoto

Tetsuya Kajihara

Hiroyuki Takaki

Masatoshi Ueoka

Fumio Shibusawa

Tadayoshi Kawashima

Masataka Nakamura

Hiroshi Jinno

Hidekazu Mizohara

Hidekazu c/o Tsuda Mizohara

The hydroxyalkyl acrylate according to the present invention is characterized in that a content amount of an ester generated from acrylic acid dimer and an alkylene oxide is not more than 0.10 mass %. The method for producing a hydroxyalkyl acrylate according to the present invention is characterized in comprising the step of reacting acrylic acid with an alkylene oxide in the presence of a catalyst, wherein a content amount of acrylic acid dimer in the raw material acrylic acid is not more than 3.00 mass %.

Hydroxyalkyl acrylate and method for producing same

Processes for producing a hydroxyalkyl(meth)acrylate which comprise reacting (meth)acrylic acid with an alkylene oxide in the presence of a catalyst. A first process is characterized in that the amount of the acid ingredient is kept, on calculation, at 0.010 or more in terms of molar ratio to the catalyst present in the liquid reaction mixture and that the liquid reaction mixture from which the hydroxyalkyl(meth)acrylate has been distilled off is used in the subsequent reaction. A second process is characterized in that a dialkylene glycol mono(meth)acylate is supplied to the reaction system to cause the dialkyleneglycol mono(meth)acylate to coexist in the liquid reaction mixture.

Processes for producing hydroxyalkyl (meth) acrylate

The present invention provides a process for inhibition of polymerization of a (meth)acrylate ester, which has an extremely higher effect of inhibition of polymerization than in cases where conventional polymerization inhibitors are used. In the process for inhibition of polymerization of a (meth)acrylate ester; an N-oxyl compound and at least one member selected from the group consisting of manganese salt compounds, copper salt compounds, 2,2,6,6-tetramethylpiperidine compounds, and nitroso compounds are used together as polymerization inhibitors, and further an acid is used.

Process for inhibition of polymerization of (meth)acrylate ester

The present invention provides: a high-quality hydroxyalkyl (meth)acrylate of which the alkylene glycol di(meth)acrylate content and the acid component content are both low; and its novel production process. The hydroxyalkyl (meth)acrylate, which has a content, in terms of an alkylene glycol di(meth)acrylate as an impurity, of not more than 0.1 weight % and an acid component content of not more than 0.1 weight %, is obtained by a process comprising the step of carrying out a batch reaction between (meth)acrylic acid and an alkylene oxide in the presence of a catalyst in order to produce the hydroxyalkyl (meth)acrylate; with the process making an adjustment as to charging of both raw materials in such a manner that, for, of a time as needed for supplying both raw materials, a supplying time of not less than 40% of a total supplying time when the raw materials as supplied have a temperature of not lower than 40&#xb0; C., the molar ratio of the integrated amount of the alkylene oxide to the integrated amount of the (meth)acrylic acid that have been added to a reactor by then can be more than 1.0.

Hydroxyalkyl (meth)acrylate and its production process

The present invention provides a novel production process for a hydroxyalkyl (meth)acrylate, in which it is possible that: in a batch reaction system, the amount of the hydroxyalkyl (meth)acrylate (which is the objective product) as produced is kept nearly on the same level as conventional and further, at the same time, there is suppressed the side production of the alkylene oxide's diaddition product (dialkylene glycol mono(meth)acrylate) that lowers the purity of the product to thus give a bad influence upon its quality. The present invention production process comprises the step of carrying out a batch reaction between (meth)acrylic acid and an alkylene oxide in the presence of a catalyst in order to produce the hydroxyalkyl (meth)acrylate; with the production process being characterized by arranging that the reaction should be initiated in a state of a catalyst concentration of more than 1, wherein the catalyst concentration is defined as the amount of the catalyst as used relative to the integrated amount of the (meth)acrylic acid as supplied and is assumed to be 1 in terms of the amount of the entire catalyst to be used relative to the amount of the entire (meth)acrylic acid to be supplied.

Production process for hydroxyalkyl (meth) acrylate

There is disclosed a novel production process for a hydroxyalkyl (meth)acrylate in which: the diffusion of harmful substances due to disposal of catalysts can be reduced; and also the amount of the catalyst as used can be greatly saved in the entire production process. This production process comprises the step of carrying out a reaction between (meth)acrylic acid and an alkylene oxide in the presence of a catalyst in order to produce the hydroxyalkyl (meth)acrylate; with the production process being characterized by further comprising the step of recovering the catalyst as has been used for the reaction.

The present invention provides a process and its utilization in a process comprising the step of carrying out an addition reaction of an alkylene oxide to an addition-receiving substance in the presence of a resin catalyst, thereby producing the addition reaction product, when the resin catalyst as used for the reaction is persevered so as to recycle it after it is recovered, the unreacted alkylene oxide remaining in the resin catalyst can be prevented from polymerizing and solidifying during the preservation, and the resin catalyst accordingly can be preserved stably for a long time. The resin catalyst as recovered after it is used for the reaction may be preserved under any of the following conditions: 1) at a low temperature of not higher than 40&#xb0; C.; 2) in the presence of a carboxylic acid; 3) in the presence of a liquid having an alkylene oxide concentration of not more than 2 weight %; and 4) in the coexistence of a carboxylic acid and a liquid having an alkylene oxide concentration of not more than 2 weight %. The present catalyst is recycled for the above addition reaction.

Process for preserving resin catalyst for addition reaction of alkylene oxide and utilization of this process

To sufficiently stabilize a hydroxyalkyl (meth)acrylate in spite of its easily polymerizable property, a hydroxyalkyl saturated-carboxylate and/or alkylene glycol as well as a phenol compound is added thereto.

Stabilized hydroxyalkyl (meth)acrylate

When carrying out a liquid-phase reaction by using a heterogeneous catalyst, the separation of the heterogeneous catalyst and the reaction liquid is carried out certainly and effectively. A reaction method involves carrying out a reaction in liquid phase by using a heterogeneous catalyst particle in a reactor , and comprises the steps of: (a) allowing a reaction liquid supplied into the reactor from such as a supplying inlet to react in the presence of the heterogeneous catalyst particle , and (b) passing the resultant reaction liquid containing the heterogeneous catalyst particle through a line screen having an opening width where the heterogeneous catalyst particle is not allowed to pass substantially, and then extracting the reaction liquid separated from the heterogeneous catalyst particle from the reactor by way of such as an extracting outlet

Reaction method by using heterogeneous catalyst and reaction apparatus therefor

Process for producing hydroxyalkyl (meth)acrylate

The present invention provides a process for producing a hydroxyalkyl (meth)acrylate which comprises the step of carrying out a reaction between (meth)acrylic acid and an alkylene oxide, wherein the process provides enablement for economically and efficiently recovering and recycling the unreacted residue of the alkylene oxide. The process for producing a hydroxyalkyl (meth)acrylate comprises the steps of, carrying out a reaction between (meth)acrylic acid and an alkylene oxide; stripping the unreacted residue of the alkylene oxide from the resultant reaction liquid; and causing a solvent to absorb the stripped alkylene oxide; wherein: water is used as the absorbing solvent; and an absorbing liquid resultant from the absorption of the unreacted residue of the alkylene oxide is used for production of an alkylene glycol.

The present invention provides: a production process for a hydroxyalkyl(meth)acrylate, which can raise productivity together with avoiding danger of explosion, and further can suppress side-formation of impurities such as a diester or a monoester wherein the impurities have a bad influence on product quality. When the time from the start of adding an alkylene oxide (AO) till the end of supplying the entirety of the AO is defined as T (hour), the amount of more than 50% of the entirety of the AO is supplied before T/2 (hour) has passed since the start of adding the AO. In addition, when the total amount of an AO as supplied and the time from the start of adding the AO till the end of supplying the entirety of the AO are defined as W (mol) and T (hour) respectively, the supply of the AO is started at a supplying speed V0 (mol/hour) that is faster than the average supplying speed V (&equals;W/T) (mol/hour), and thereafter the supplying speed of the AO is decreased at least once, and then the supply of the entirety of the AO is completed for T (hour) from the start of adding the AO.

Production process for hydroxyalkyl (meth)acrylate

In a production process for a hydroxyalkyl ester, comprising the step of carrying out a reaction between a carboxylic acid and an alkylene in the presence of a catalyst, the present invention is to provide: a production process which can stop the reaction economically and sufficiently safely. In a production process which comprises the step of carrying out the reaction between a carboxylic acid and an alkylene in a reactor in the presence of a catalyst so as to produce a hydroxyalkyl ester, the reaction is stopped by introducing a reaction terminating liquid into the reactor , wherein the reaction terminating liquid comprises water in a ratio of not less than 50 weight %, and has a low temperature of &minus;5 to 45&deg; C.

Production process for hydroxyalkyl ester

A production process for a hydroxyalkyl(meth)acrylate, which comprises the steps of carrying out a reaction between (meth)acrylic acid and an alkylene oxide and stripping the unreacted residue of the alkylene oxide from the resultant reaction liquid, wherein: (1) the stripping step is performed by use of an inert gas, and the concentration of oxygen in the inert gas is adjusted in the range of 0.1 to 5 mol %; (2) the concentration of the unreacted residue of the (meth)acrylic acid in the resultant reaction liquid is suppressed to not higher than 10 weight %; (3) the difference in operational pressure between the stripping step and the absorption step of causing a solvent to absorb the stripped alkylene oxide is suppressed to not more than 1,000 hPa; (4) the reaction liquid resultant from the reaction is directly supplied to the stripping step without being heated; (5) a part of the liquid left behind in the stripping step is heated and then supplied to the stripping step again; (6) a hydroxyalkyl (meth)acrylate solution is used as the absorbing solvent; (7) a part of the liquid resultant from the absorption step is cooled and then supplied to the absorption step again; or (8) a part or the whole of the absorbing liquid which is on the way of the absorption step is extracted and then cooled and then supplied to the absorption step again.

Production process for hydroxyalkyl(meth)acrylate

The present invention provide a production process for a hydroxyalkyl ester which comprises the step of carrying out a reaction between a carboxylic acid and an alkylene oxide in the presence of a catalyst, wherein the production process sufficiently enhances the conversion or selectivity in the reaction. The production process is characterized in that the reaction is carried out in a reaction liquid under conditions where a relationship a<b is kept throughout the reaction wherein &ldquo;a&rdquo; is a molar concentration (mol %) of the carboxylic acid in the reaction liquid and wherein &ldquo;b&rdquo; is a molar concentration (mol %) of the alkylene oxide in the reaction liquid.

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Himeji, Japan

Tokumasa Ishida