Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1987-04-03
1990-08-07
Gray, Bruce
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
564484, C07C 8504
Patent
active
049469967
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a method for preparing an allyl amine compound and to a method for preparing a quaternary, diallyl ammonium compound therefrom.
Quaternary diallyl dialkyl ammonium compounds such as diallyl dimethyl ammonium chloride are monomeric materials which can be polymerized, both homo- and copolymerized, to form polymers useful in a variety of applications. For example, a polymer derived, at least partially, from a diallyl dimethyl ammonium chloride can be employed as a flocculant in waste water treatment, as a wet strength agent or retention and drainage aid in the preparation of paper, as an antistatic additive, an acid-dye receptor or a biocide.
Heretofore, quaternary diallyl dialkyl ammonium compounds have conventionally been prepared, on a commercial scale, by the reaction, in an aqueous medium, of a secondary amine such as dimethyl amine with an allyl halide (e.g., allyl chloride) in the presence of an alkali metal hydroxide (e.g., sodium hydroxide). See, for example, U.S. Pat. No. 2,923,701. In general, an excess of the allyl halide is employed to ensure complete reaction of the secondary amine. The excess allyl halide is stripped under vacuum. The resulting product is an aqueous solution containing the desired quaternary diallyl dialkyl ammonium compound. Unfortunately, a large amount of salt (e.g., sodium chloride) is formed during the reaction, and is present in the reaction product. This restricts the ability to polymerize the resulting compound.
Various methods have been proposed to reduce the amount of salt and otherwise improve the purity of the quaternary ammonium product. See, for example, U.S. Pat. No. 3,472,740. Using the described techniques, the purity of the quaternary ammonium compound is improved while simultaneously reducing the amounts of salt in solution by evaporating water from the aqueous reaction product such as by steam distillation to remove the unreacted allyl chloride and secondary amine and to precipitate the salt. The precipitated salt can subsequently be removed from the aqueous solution by filtration. Following evaporation of the water and removal of the precipitated salt, the aqueous solution of the quaternary ammonium compound can be passed over an activated carbon to further purify the reaction product. Unfortunately, the amounts of water which can be evaporated (and hence, the amounts of salt which can be precipitated from solution) is limited due to the hygroscopic nature of the quaternary ammonium compound. In fact, upon the removal of all possible water, a highly viscous oil of an over-saturated solution of the quaternary ammonium compound in water which still contains a high percentage of salt is formed. Moreover, the described purification method is time consuming and capital intensive.
Yet another means for reducing the amount of salt formed in the preparation of the quaternary ammonium compound is disclosed in Japanese patent specification 50-77308. Specifically, the disclosed method comprises precipitating the salt with organic solvent following the reaction of dialkyl amine with allyl halide. Subsequently, the precipitated salt is removed to yield an aqueous solution of the quaternary ammonium compound. Unfortunately, the described method does not precipitate all the salt and the product still contains a relatively high concentration of salt. Moreover, it is necessary using the described process, to separate the added organic liquid from the mixture of water and quaternary ammonium compound.
In addition to containing relatively large amounts of salt, using the described techniques and other known techniques, the quaternary ammonium compound is prepared as a solution in an aqueous liquid. Therefore, it is necessary to ship large amounts of water in transporting the quaternary ammonium product. In addition, polymerization of the quaternary ammonium compound is limited to aqueous polymerization systems. Moreover, further improvements in yield of the desired quaternary ammonium compound are desired.
The preparation of a solid diallyl di
REFERENCES:
patent: 3461163 (1969-08-01), Boothe
patent: 3471561 (1969-10-01), Dadekian et al.
Turner, The Design of Organic Syntheses, Elsevier Scientific Publishing Company, (1976).
Lienert Klaus-Wilhelm
Schleinzer Matthias
Gray Bruce
Karadzic Dragan J.
The Dow Chemical Company
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