Process for preparing N-alkyl ammonium acetonitrile compounds

Details Process for preparing N-alkyl ammonium acetonitrile compounds Process for preparing N-alkyl ammonium acetonitrile compounds

1999-11-19

2001-05-22

Anthony, Joseph D. (Department: 1714)

Compositions

Oxidative bleachant, oxidant containing, or generative

Contains activator admixed with inorganic peroxide

C544S163000, C544S402000, C544S086000, C510S312000

Reexamination Certificate

active

06235218

ABSTRACT:

FIELD OF THE INVENTION
The present invention generally relates to N-alkyl ammonium acetonitrile compounds useful in applications such as bleaching and cleaning and particularly relates to a process for the preparation of such compounds.
This application is a continuation in part of Ser. No. 08/475,292, filed Jun. 7, 1995, entitled “N-ALKYL AMMONIUM ACETONITRILE BLEACH ACTIVATORS,” inventors Arbogast et al., of common assignment herewith.
BACKGROUND OF THE INVENTION
Peroxy compounds are effective bleaching agents, and compositions including mono- or di-peroxyacid compounds are useful for industrial or home laundering operations. For example, U.S. Pat. No. 3,996,152, issued Dec. 7, 1976, inventors Edwards et al., discloses bleaching compositions including peroxygen compounds such as diperazelaic acid and diperisophthalic acid.
Peroxyacids (also known as “peracids”) have typically been prepared by the reaction of carboxylic acids with hydrogen peroxide in the presence of sulfuric acid. For example, U.S. Pat. No. 4,337,213, inventors Marynowski et al., issued Jun. 29, 1982, discloses a method for making diperoxyacids in which a high solids throughput may be achieved.
However, granular bleaching products containing peroxyacid compounds tend to lose bleaching activity during storage, due to decomposition of the peroxyacid. The relative instability of peroxyacid can present a problem of storage stability for compositions consisting of or including peroxyacids.
One approach to the problem of reduced bleaching activity of peroxyacid compositions has been to include activators of hydrogen peroxide or an active oxygen source. U.S. Pat. No. 4,283,301, inventor Diehl, issued Aug. 11, 1981, discloses bleaching compositions including peroxygen bleaching compounds, such as sodium perborate monohydrate or sodium perborate tetrahydrate, and activator compounds such as isopropenyl hexanoate and hexanoyl malonic acid diethyl ester.
Other examples of activators include tetraacetyl ethylenediamine (TAED), nonanoyloxy benzene-sulfonate (NOBS), and nonanoylglycolate phenol sulfonate (NOGPS). NOBS and TAED are disclosed, for example, in U.S. Pat. No. 4,417,934, Chung et al., and NOGPS is disclosed, for example, in U.S. Pat. No. 4,778,618, Fong et al., the disclosures of which are incorporated herein by reference.
Thus, U.S. Pat. No. 4,778,618, Fong et al., issued Oct. 18, 1988 provides novel bleaching compositions comprising peracid precursors with the general structure
wherein R is C
1-20
linear or branched alkyl, alkylethoxylated, cycloalkyl, aryl, substituted aryl; R′ and R″ are independently H, C
1-20
alkyl, aryl, C
1-20
alkylaryl, substituted aryl, and N
+
R
3
&agr;
, wherein R
&agr;
is C
1-30
alkyl; and where L is a leaving group which can be displaced in a peroxygen bleaching solution by peroxide anion. U.S. Pat. No. 5,182,045, issued Jan. 26, 1993, and U.S. Pat. No. 5,391,812, issued Feb. 21, 1995, inventors Rowland et al. are similar, but are polyglycolates of the Fong et al. monoglycolate precursors, or activators.
U.S. Pat. No. 4,915,863, issued Apr. 10, 1990, inventors Aoyagi et al., discloses compounds said to be peracid precursors that have nitrile moieties. U.S. Pat. No. 5,236,616, issued Aug. 17, 1993, inventors Oakes et al., discloses compounds said to be cationic peroxyacid precursors that have nitrile moieties. These nitrile containing activators do not contain a leaving group, such as the Fong et al. leaving groups, but instead include a quaternary ammonium group suggested as activating the nitrile and said, upon reaction or perhydrolysis in the presence of hydrogen peroxide, to generate a peroxy imidic acid as bleaching species. The Aoyagi et al. activators include an aromatic ring, which tends to cause fabric yellowing.
German patent application P4431212.1, published Mar. 7, 1996 describes production of quaternized glycinonitriles in the form of stable aqueous solutions.
New peroxygen activators that provide excellent bleaching and that can be formulated for liquid or solid compositions remain desirable for applications such as laundry and household bleaching and cleaning.
SUMMARY OF THE INVENTION
In one aspect of the present invention, nitrites are provided in substantially solid form having the structure of Formula I
wherein A is a saturated ring formed by five atoms in addition to the N
1
atom, the five saturated ring atoms being four carbon atoms and a heteroatom, the substituent R
1
bound to the N
1
atom of the Formula I structure including either (a) a C
1-24
alkyl or alkoxylated alkyl where the alkoxy is C
2-4
, (b) a C
4-24
cycloalkyl, (c) a C
7-24
alkaryl, (d) a repeating or nonrepeating alkoxy or alkoxylated alcohol, where the alkoxy unit is C
2-24
, or (e) —CR
2
R
3
C≡N where R
2
and R
3
are each H, a C
1-24
alkyl, cycloalkyl, or alkaryl, or a repeating or nonrepeating alkoxyl or alkoxylated alcohol where the alkoxy unit is C
2-4
.
The Formula I compounds have a quaternary nitrogen atom (N
1
), requiring the presence of at least one counterion (Y) to be associated therewith, which is illustrated in Formula I as “Y
⊖
,” but as understood can be monovalent, or multivalent. Y includes counterions, or organic and inorganic anions, such as chloride, bromide, nitrate, alkyl sulfate, bisulfate, sulfate, tosylate, and mesylate. Especially preferred are methyl sulfate, sulfate, bisulfate, tosylate, and mixtures thereof. Z will be in the range of 0 to 10. These compounds, or salts, are particularly well suited to granule bleaching and cleaning compositions.
The nitriles with the Formula I structure are particularly useful when formulated as compositions that include a source of active oxygen, and these compositions provide excellent bleaching in alkaline solutions.
Preferred embodiments include lower alkyls substituted at the N
1
, e.g. N-methyl morpholinium acetonitrile, N-ethyl morpholinium acetonitrile, N-butyl morpholinium acetonitrile, which are illustrated by Formula II (with “n” preferably being 0 to 24 and where “Y” is one of the above described counterions).
A particularly preferred embodiment is an N-methyl morpholinium acetonitrile salt where “n” of Formula II is 0. In the preferred process for preparing the Formula I or Formula II compounds, decomposition of a process intermediate is substantially avoided so as to reduce amounts of undesired free hydrogen cyanide, preferably to below the analytical detection limit. In a preferred embodiment of the process, a compound with the structure of Formula II is prepared to be substantially free of hydrogen cyanide by reacting morpholine with a monoaldehyde or a dialdehyde and hydrogen cyanide or an alkali metal cyanide in an aqueous medium (Step A) and then with an alkylating agent (Step B), whereby Step A is carried out in a pH range of from 8 to 14 and Step B is carried out at a pH of not less than about 2. Most preferably, Step B is carried out at a pH of not less than about 3.
Compositions including these nitriles are useful, for example, in laundry products, such as bleaching additives, detergents, detergent boosters, detergents with bleach, bleaches, bleaching aids, stain removers, and spot treatment products such as stain removers, prewash and presoak laundry aids. Among the advantages derived from such compositions are improved cleaning, stain removal, spot removal, whitening, and brightening of treated articles.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Application Ser. No. 08/475,291, filed Jun. 7, 1995, entitled “N-Alkyl Ammonium Acetonitrile Bleach Activators,” describes nitrites, typically quaternized, for which a preferred embodiment was N-methyl ammonium acetonitrile methylsulfate, to which this application relates. There are several aspects of the present invention.
One aspect is wherein novel quaternized nitriles are provided having certain counterions which result in substantially reduced hygroscopicity (with respect to amorphous N-methyl ammonium acetonitrile methylsulfate, or MMAMS). Another aspect is wherein novel nitrites are provided as granules by

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