Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1998-07-11
2000-10-31
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C07C 6952
Patent
active
061405337
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a process for producing sec-butyl acrylate with a high selectivity and a high conversion ratio, while inhibiting catalyst deterioration.
BACKGROUND ART
Japanese Patent Application Examined Publication No. 6-104645 discloses a process for producing sec-butyl acrylate by allowing acrylic acid to react with 1-butene in the presence of ion exchange resins having sulfo groups. Although this process is excellent in selectivity and conversion ratio, there is a demand for processes for producing sec-butyl acrylate further excelling in selectivity and conversion ratio.
DISCLOSURE OF INVENTION
The object of the present invention is to improve the above-described process, thereby providing a process for producing sec-butyl acrylate with a higher selectivity and a higher conversion ratio, while inhibiting catalyst deterioration.
As the results of researches for achieving the object, the inventor has found that a high selectivity toward sec-butyl acrylate, a high conversion ratio and the inhibition of catalyst deterioration can be attained by carrying out the reaction of acrylic acid with specific butenes in the presence of ion exchange resins having sulfo groups in a liquid phase reaction system containing 0.01 to 1.50 wt % of water, and has completed the present invention based on the finding.
That is, the present invention provides a process for producing sec-butyl acrylate, comprising allowing acrylic acid to react with a butene selected from the group consisting of butene-1, trans-2-butene and cis-2-butene, in a molar ratio of butene/acrylic acid ranging from 1 to 6, in the presence of an ion exchange resin having sulfo groups, in a liquid-phase reaction system containing 0.01 to 1.50 wt % of water, at a reaction temperature of 40 to 120.degree. C.
BEST MODE FOR CARRYING OUT THE INVENTION
The butene to be used in the present invention is selected from the group consisting of butene-1, trans-2-butene and cis-2-butene, which may be used individually or as a mixture of two or three.
The molar ratio of butene to acrylic acid (butene/acrylic acid) ranges from 1 to 6, preferably from 2 to 5, more preferably from 3 to 4.
The ion exchange resin having sulfo groups to be used in the present invention may be selected from any ion exchange resins having sulfo groups. None-limitative examples of the ion exchange resins are those prepared by introducing sulfo groups into polymer substrates, for example, copolymers of polymerization monomers, such as styrene, with di- or more-functional crosslinking agents, such as divinylbenzene. It is possible to use commercial ion exchange resins, for example, AMBERLYST 15, AMBERLYST 16 (trade names, produced by Rohm & Haas Co., Ltd.), K2441, K2461, K2661 (trade names, produced by Bayer Aktiengesellschaft), DOWEX 88 and DOWEX MSC-1 (trade names, produced by The Dow Chemical Company).
These ion exchange resins are porous, and the preferred ion exchange resins have a BET surface area of 20 to 100 m.sup.2 /g, a maximum pore diameter of 1000 .ANG., a porosity of 20 to 80% and an ion exchange capacity of 0.5 to 3 milliequivalent/litter.
The amount of the ion exchange resins having sulfo groups is generally 2 to 20 wt %, preferably 4 to 15 wt %, based on acrylic acid.
The reaction is carried out in a liquid phase and may be performed by using a fixed bed or an agitation chamber, and also may be performed by a patch process or a continuous process.
The reaction of the process of the present invention should be carried out in the presence of 0.01 to 1.50 wt % of water in the reaction system. Herein, the terms "reaction system" mean a system comprising the reaction mixture of acrylic acid and butene, water and optional polymerization inhibitors, and the amount of the ion exchange resins used as catalysts is not included in the amount of the reaction system. If the water content in the reaction system is less than 0.01 wt % or more than 1.50 wt %, the selectivity and the conversion ratio toward sec-butyl acrylate will be decreased, and signifi
REFERENCES:
patent: 5138092 (1992-08-01), Perez Pascual et al.
patent: 5596126 (1997-01-01), Riondel
Idemitsu Petrochemical Co. Ltd.
Killos Paul J.
White Everett
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