Process for preparing amidoalkanesulfonic acids

Details Process for preparing amidoalkanesulfonic acids Process for preparing amidoalkanesulfonic acids

1985-11-01

1987-10-20

Henderson, Christopher

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260513N, C07C143155

Patent

active

047012838

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

1. Technical Field
This invention relates to a process for preparing amidoalkanesulfonic acids and derivatives, such as salts, thereof (hereinafter referred to briefly as amidoalkanesulfonic acid derivatives), as well as copolymer-coated solid materials, copolymer emulsions and pigment dispersants in which the copolymer is obtained by copolymerizing such an amidoalkanesulfonic acid derivative (in particular, 2-acrylamido-2-phenylpropanesulfonic acid or its salt) with another monomer or the like.
2. Background Art
Amidoalkanesulfonic acid derivatives are useful as lime soap dispersants. Among others, unsaturated amidoalkanesulfonic acid derivatives are known to have wide applications as raw materials for the manufacture of water-soluble polymers (for example, flocculants, dispersants, adhesives and thickeners) and as raw materials for the manufacture of ion exchangers such as ion exchange resins.
Conventionally, there are two well-known methods for preparing amidoalkanesulfonic acid derivatives. One of them involves the reaction of an aminoalkanesulfonic acid or its derivative with acrylic acid chloride and the other involves the reaction of a nitrile, an olefin and concentrated sulfuric acid including fuming sulfuric acid.
However, the former method requires expensive raw materials and, therefore, is not suitable for industrial practice. On the other hand, the latter method is currently used in the industrial production of 2-acrylamido-2-methylpropanesulfonic acid (hereinafter abbreviated as AMPS). However, although this method is suitable for the preparation of AMPS, it is not yet perfected as a technique fully applicable to the preparation of other amidoalkanesulfonic acid derivatives. One reason for this is that the olefin used in the latter method generally has a very high degree of cationic polymerizability. Thus, the method is practicable in the case of isobutene, but other olefins used as raw materials tend to undergo side reactions (cationic polymerization and the like) in concentrated sulfuric acid and fail to produce satisfactory results.


DISCLOSURE OF THE INVENTION

It is an object of the present invention to provide a novel process for preparing amidoalkanesulfonic acid derivatives which permits not only AMPS but also other amidoalkanesulfonic acid derivatives to be prepared with ease.
It is another object of the present invention to provide polymer-coated solid materials, polymer emulsions and pigment dispersants useful in industry, which are obtained by using unsaturated amido- and phenyl-substituted alkanesulfonic acids, preferably 2-acrylamido-2-phenylpropanesulfonic acid, among the amidoalkanesulfonic acid derivatives prepared by the aforesaid process or the like and copolymerizing them with monomers having a radical polymerizable unsaturated bond or .alpha.,.beta.-monoethylenically unsaturated carboxylic acids.
The above-described first object of the present invention can be accomplished by reacting a nitrile compound of the general formula .beta.-hydroxyalkanesulfonic acid of the general formula ##STR3## where R.sub.2 and R.sub.3 are hydrogen, lower alkyl groups or phenyl groups, or an alkali metal, alkaline earth metal or ammonium salt thereof in concentrated sulfuric acid to form an amidoalkanesulfonic acid of the general formula ##STR4## where R.sub.1, R.sub.2 and R.sub.3 have the same meanings as described above, or a derivative thereof.
The above-described second object can be accomplished by carrying out the respective methods which will be described later.


BEST MODE FOR CARRYING OUT THE INVENTION

To begin with, there will be described the process for preparing amidoalkanesulfonic acid derivatives which process constitutes the first object of the present invention.
Specifically, the nitrile compounds which can be used in the process of the present invention include saturated hydrocarbon nitriles, unsaturated hydrocarbon nitriles and aromatic hydrocarbon nitriles, all having 1 to 12 carbon atoms. Examples thereof are acetonitrile, propionitrile, butyronitrile, octa

REFERENCES:
patent: 3547899 (1970-12-01), Arlt
patent: 4219498 (1980-08-01), Doi
Organic Reactions, 17, 216-217, and 226.
Kharash et al, J.A.C.S., 61, 3092-3098 (1939).
March, J., Advanced Org. Chem., McGraw Hill (N.Y.), 1968, p. 715.

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