Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus acids or salts thereof
Patent
1996-03-01
1997-10-21
Geist, Gary
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus acids or salts thereof
C07F 938
Patent
active
056798440
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a manufacturing method for N-phosphonomethylglycine and salts thereof which are phosphonic acid derivatives and are useful as herbicides and starting materials and the like for herbicides.
BACKGROUND ART
N-phosphonomethylglycine and salts thereof, for example, glyphosate, sodium glyphosate, ammonium glyphosate, glyphosate-monodimethylamine, glyphosphate trimethylsulfonium salt (sulfosate), glyphosamine, and the like, can be biologically degraded, in addition, they are effective for use in small amounts as herbicide, and are either being used widely, or are having their effectiveness examined.
There are many known manufacturing methods for N-phosphonomethylglycine; there are methods which use N-phosphonomethylglycinonitrile as a starting material or intermediate, which can be converted into the desired N-phosphonomethylglycine by means of hydrolysis of the nitrile group of the N-phosphonomethylglycinonitrile.
Moreover, manufacturing methods for N-phosphonomethylglycinonitrile are described in, for example, Japanese Patent Application, Second Publication, No. Sho 60-4840; Japanese Patent Application, First Publication, No. Hei 4-279595; U.S. Pat. No. 4,221,583; etc.
With regard to the hydrolysis of N-phosphonomethylglycinonitrile, hydrolysis by means of sodium hydroxide is given as an example in U.S. Pat. No. 4,221,583.
In addition, Japanese. Patent Application, First Publication, No. Hei 4-279595 describes a reaction of aminomethylphosphonic acid and glycolonitrile, wherein not less than twice the number of moles of alkali metal hydroxide, compared with the aminomethylphosphonic acid, are added and reacted. Hydrolysis takes place by the addition of additional alkali metal hydroxide in amounts sufficient to neutralize the carboxylic acid generated as a result of the hydrolysis of the nitrile group of the obtained N-phosphonomethylglycinonitrile.
In the isolation of N-phosphonomethylglycine from the aqueous solution resulting from the alkali hydrolysis of N-phosphonomethylglycinonitrile, since a method of neutralization using acid takes place, a salt by-product is produced by the use of alkali metal hydroxide, and dealing with this salt by-product is expensive and laborious.
An object of the present application is to provide a manufacturing method for N-phosphonomethylglycine which brings about a reduction in the salt by-product which is produced by using alkali, such as alkali metal hydroxides or alkaline-earth metal hydroxides, and which is a major problem when manufacturing N-phosphonomethylglycine by means of alkali hydrolysis of N-phosphonomethylglycinonitrile; moreover, the present application aims to provide a manufacturing method for N-phosphonomethylglycine which is industrially advantageous, and achieves high purity and high yields.
DISCLOSURE OF THE INVENTION
The manufacturing method for the phosphonic acid derivatives of the present invention is a method in which N-phosphonomethylglycine and salts thereof are obtained by hydrolysis using alkali so as to result in not less than 2 molecules and less than 3 molecules of the alkali for each molecule of the N-phosphonomethylglycinonitrile when the alkali cation is monovalent, and using the alkali so as to result in not less than 1 molecule and less than 1.5 molecules of the alkali for each molecule of the N-phosphonomethylglycinonitrile when the alkali cation is divalent.
As the above-mentioned alkali, it is preferable to use alkali metal hydroxides or alkaline-earth metal hydroxides. When using alkali metal hydroxides, the alkali metal hydroxides so as to result in 2 molecules or more and less than 3 molecules, preferably 2.1 molecules or more and less than 2.7 molecules of the alkali metal hydroxides for each molecule of N-phosphonomethylglycinonitrile are used. In addition, when using alkaline-earth metal hydroxides, the alkaline-earth metal hydroxides so as to result in 1 molecule or more and less than 1.5 molecules, preferably 1.05 molecules or more and less than 1.35 molecules of the alkalin
REFERENCES:
patent: 3799758 (1974-03-01), Franz
patent: 3923877 (1975-12-01), Barton
patent: 3977860 (1976-08-01), Franz
patent: 4221583 (1980-09-01), Gaertner et al.
patent: 4415503 (1983-11-01), Robbins
patent: 5453537 (1995-09-01), Morikawa et al.
International Search Report Sep. 26, 1995.
Miyata Hideo
Morikawa Kohei
Sasaki Toru
Geist Gary
Showa Denko K.K.
Vollano Jean F.
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