Process for preparing &bgr;-hydroxy-&ggr;-butyrolactones and...

Details Process for preparing &bgr;-hydroxy-&ggr;-butyrolactones and... Process for preparing &bgr;-hydroxy-&ggr;-butyrolactones and...

2000-06-26

2001-11-06

Solola, T. A. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S318000

Reexamination Certificate

active

06313321

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a process for preparing &bgr;-hydroxy-&ggr;-butyrolactone and &bgr;-methyl-&bgr;-hydroxy-&ggr;-butyrolactone (hereinafter referred to as “&bgr;-hydroxy-&ggr;-butyrolactones”), and a process for preparing &bgr;-(meth)acryloyloxy-&ggr;-butyrolactone and &bgr;-methyl-&bgr;-(meth)acryloyloxy-&ggr;-butyrolactone (hereinafter referred to as “&bgr;-(meth)acryloyloxy-&ggr;-butyrolactones”) which are useful as a constituent component monomer of paints, adhesives, sticking agents, and resins for ink, for example.
2. Description of the Background
&bgr;-hydroxy-&ggr;-butyrolactones, which are used as a precursor of &bgr;-(meth)acryloyloxy-&ggr;-butyrolactones, for example, may be prepared by reacting glycidol with carbon monoxide at high temperature under high pressure using a noble metal as a catalyst (U.S. Pat. No. 4,968,817) and by lactonizing an epoxidized product, obtained by reacting 3-butenoic acid with hydrogen peroxide in the presence of a platinum catalyst, after hydrating the epoxidized product (Angew. Chem., Int. Ed. Eng. 994-1000 (1966)). However, both methods are attended by a high risk of explosion.
Due to this risk, it is difficult to industrially prepare &bgr;-hydroxy-&ggr;-butyrolactones, hence, &bgr;-(meth)acryloyloxy-&ggr;-butyrolactones have never been producing industrially using these compounds as a raw material, despite the expected use for various purposes.
Therefore, it has been considered desirable to develop a process for preparing &bgr;-hydroxy-&ggr;-butyrolactones in a safe and simple manner, as well as a process for preparing &bgr;-(meth)acryloyloxy-&ggr;-butyrolactones.
SUMMARY OF THE INVENTION
Accordingly, it is an object of the present invention to provide a process for preparing &bgr;-hydroxy-&ggr;-butyrolactones in a safe and simple manner, as well as a process for preparing &bgr;-(meth)acryloyloxy-&ggr;-butyrolactones, which are useful as a constituent component monomer of paints, adhesives, sticking agents, and resins for ink, for example, using &bgr;-hydroxy-&ggr;-butyrolactones obtained by the above process.
In particular, the present invention provides a process for preparing corresponding &bgr;-hydroxy-&ggr;-butyrolactone or &bgr;-methyl-&bgr;-hydroxy-&ggr;-butyrolactone represented by the formula (1):
wherein R
1
represents a hydrogen atom or a methyl group, which entails cyanating glycidol or 2-methyl-2,3-epoxypropanol, followed by hydrolysis and then lactonization.
The present invention also provides a process for preparing corresponding the &bgr;-(meth)acryloyloxy-&ggr;-butyrolactone or &bgr;-methyl-&bgr;-(meth)acryloyloxy-&ggr;-butyrolactone represented by the formula (2):
wherein R
1
and R
2
independently represent a hydrogen atom or a methyl group, which entails preparing &bgr;-hydroxy-&ggr;-butyrolactone or &bgr;-methyl-&bgr;-hydroxy-&ggr;-butyrolactone by the above process, and then reacting the resulting &bgr;-hydroxy-&ggr;-butyrolactone or &bgr;-methyl-&bgr;-hydroxy-&ggr;-butyrolactone with (meth)acrylic acid chloride, (meth)acrylic acid or (meth)acrylic ester.


REFERENCES:
patent: 4200582 (1980-04-01), Distler et al.
patent: 4968817 (1990-11-01), Brima
patent: 54-95558 (1979-07-01), None
patent: 2-129645 (1990-05-01), None
patent: 10-212283 (1998-08-01), None

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