Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2001-11-19
2003-03-11
Richter, Johann (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S471000, C568S472000, C568S689000, C568S878000, C568S884000
Reexamination Certificate
active
06531635
ABSTRACT:
This application is a 371 of PCT/JP00/03130, filed May 16, 2000, now WO00/69799, published Nov. 23, 2000.
TECHNICAL FIELD
The present invention relates to a method for producing 3-alkoxyalkanol precursors, and to a method for producing 3-alkoxyalkanols. More precisely, the invention relates to a method for producing a 3-alkoxyalkanol precursor mixture of 1,1,3-trialkoxyalkane and 3-alkoxyalkanal; to a method for producing a 3-alkoxyalkanal precursor, 1,1,3-trialkoxyalkane; to a method for producing a 3-alkoxyalkanol precursor, 3-alkoxyalkanal; and to a method for producing a 3-alkoxyalkanol.
BACKGROUND ART
For producing 3-alkoxyalkanols such as 3-methoxypropanol, which are useful for solvents for paints and photoresists and for materials for chemical products, heretofore known are <1> a method of reacting trimethylene glycol with a metal followed by reacting the resulting sodium alkoxide with an alkyl halide (J. Am. Chem. Soc., 65, 1276, 1943); <2> a method of reacting 3-chloro-1-propyl alcohol with a metal alkoxide (Japanese Patent Laid-Open No. 113546/1996); and <3> a method of decomposing a diazonium salt obtained from an aminoether (Japanese Patent Laid-Open No. 316605/1998). However, the starting materials for these methods are difficult to obtain, and the practicability of the methods is therefore low.
Another method <4> for which the starting materials are easy to obtain is known. The method comprises hydrogenating a reaction product, which is obtained through reaction of acrolein and methanol in the presence of a basic catalyst, followed by reacting the resulting hydrogenate with acetic acid in the presence of an acid catalyst to give 3-methoxy-1-acetoxypropane (Japanese Patent Laid-Open No. 25821/1995). The patent publication says that the reaction of acrolein with methanol in the presence of a basic catalyst gives a reaction product containing 3-methoxypropylaldehyde, and that the hydrogenation of the reaction product gives a liquid reaction product containing 3-methoxypropanol. However, the method <4> requires a basic catalyst and therefore requires accurate and delicate reaction control. Another drawback of the method is that the yield of 3-alkoxyalkanol therein is low.
The present invention is to solve the drawbacks of the prior-art methods as above, and to provide an efficient and high-yield method for producing 3-alkoxyalkanols and their precursors.
The invention includes four aspects, first to fourth aspects.
The first aspect of the invention is to provide an efficient and high-yield method for producing a 3-alkoxyalkanol precursor mixture of 1,1,3-trialkoxyalkane and 3-alkoxyalkanal. Another object of the first aspect is to provide an efficient and high-yield method for producing a 3-alkoxyalkanol precursor, 3-alkoxyalkanal, from the mixture. Still another object is to provide an efficient and high-yield method for producing the 3-alkoxyalkanol, a final product, from an &agr;,&bgr;-unsaturated aldehyde and an alcohol.
The second aspect of the invention is to provide an industrial method for producing a 3-alkoxyalkanal. Another object of the second aspect is to provide a method for producing a 3-alkoxyalkanol of high purity.
The third aspect of the invention is to provide an industrial method for producing a 3-alkoxyalkanol.
The forth aspect of the invention is to provide an industrial method for producing a 3-alkoxyalkanol of high purity. Another object of the fourth aspect is to provide a method for producing a 1,1,3-trialkoxyalkane and a 3-alkoxyalkanal that give such a 3-alkoxyalkanol.
DISCLOSURE OF THE INVENTION
We, the present inventors have assiduously studied so as to attain the objects of the first aspect of the invention, and, as a result, have found that the objects can be attained by reacting an &agr;,&bgr;-unsaturated aldehyde with an alcohol in the presence of an acid catalyst followed by hydrolyzing the resulting reaction product and then hydrogenating it. On the basis of this finding, we have completed the first aspect of the invention.
To attain the objects of the second aspect of the invention, we, the inventors have assiduously studied on the premise of direct use of oxidized products of propylene or isobutylene, and, as a result, have found that the objects can be attained by distilling a liquid reaction product of acrolein or methacrolein with an alcohol to collect an azeotropic mixture of 3-alkoxyalkanal with water from it, followed by hydrogenating the thus-obtained 3-alkoxyalkanal. On the basis of this finding, we have completed the second aspect of the invention.
To attain the objects of the third aspect of the invention, we, the inventors have specifically noted a step of hydrolysis and a step of hydrogenation of a mixture of 1,1,3-trialkoxyalkane and 3-alkoxyalkanal, and have assiduously studied them. As a result, we have found that the objects can be attained by simultaneously hydrolyzing and hydrogenating the mixture, and, on the basis of this finding, we have completed the third aspect of the invention.
To attain the objects of the fourth aspect of the invention, we, the inventors have specifically noted the treatment of the oxidation product gas of propylene or isobutylene, and have assiduously studied it. As a result, we have found that the objects can be attained by contacting the oxidation product gas of propylene or isobutylene with an alcohol in a specific condition, and, on the basis of this finding, we have completed the fourth aspect of the invention.
Specifically, the present invention provides the following:
(1) A method for producing a mixture of 1,1,3-trialkoxyalkane and 3-alkoxyalkanal, which comprises reacting an &agr;,&bgr;-unsaturated aldehyde with an alcohol in the presence of an acid catalyst;
(2) A method for producing a 3-alkoxyalkanal, which comprises hydrolyzing the mixture produced in the method of above (1);
(3) A method for producing a 3-alkoxyalkanol, which comprises hydrogenating the 3-alkoxyalkanal produced in the method of above (2);
(4) A method for producing a 3-alkoxyalkanal, which comprises distilling a liquid reaction product of acrolein or methacrolein obtained through oxidation of propylene or isobutylene and containing acids, with an alcohol, to thereby collect an azeotropic mixture of a 3-alkoxyalkanal with water;
(5) A method for producing a 3-alkoxyalkanol, which comprises hydrogenating the 3-alkoxyalkanal produced in the method of above (4);
(6) A method for producing a 3-alkoxyalkanol, which comprises simultaneously hydrolyzing and hydrogenating a reaction mixture of 1,1,3-trialkoxyalkane and 3-alkoxyalkanal obtained through reaction of an &agr;,&bgr;-unsaturated aldehyde with an alcohol;
(7) A method for producing a 1,1,3-trialkoxyalkane, which comprises reacting acrolein gas or methacrolein gas obtained through contact of an oxidation product gas of propylene or isobutylene with an alcohol capable of almost completely vaporizing in the system, with an alcohol;
(8) A method for producing a 3-alkoxyalkanal, which comprises hydrolyzing the 1,1,3-trialkoxyalkane produced in the method of above (7);
(9) A method for producing a 3-alkoxyalkanol, which comprises hydrogenating the 3-alkoxyalkanal produced in the method of above (8); and
(10) A method for producing a 3-alkoxyalkanol, which comprises simultaneously hydrolyzing and hydrogenating the 1,1,3-trialkoxyalkane produced in the method of above (7).
BEST MODES OF CARRYING OUT THE INVENTION
Embodiments of the invention are described below.
First described is the first aspect of the invention. It includes three embodiments. The first embodiment is a method for producing a mixture of 1,1,3-trialkoxyalkane and 3-alkoxyalkanal, and it comprises reacting an &agr;,&bgr;-unsaturated aldehyde with an alcohol in the presence of an acid catalyst.
The acid catalyst to be used in this first aspect is not specifically defined. For this, however, preferred are mineral acids such as sulfuric acid and hydrochloric acid; and solid catalysts such as strong-acidic ion-exchange resins. Of those, especially preferred is a catalyst
Kawano Naoya
Kawasaki Hiroshi
Yoshitome Toshihide
Idemitsu Petrochemicals Co., Ltd.
Richter Johann
Witherspoon Sikarl A.
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