Sodium monochloroacetate

Nitromethane, CH3NO2, the first member of the homologous series, can, however, be readily prepared by a special reaction. When equimolecular amounts of sodium nitrite and sodium monochloroacetate are heated together in aqueous solution, the chlorine in the monochloroacetate is replaced by the nitro group, and the sodium nitroacetate thus formed undergoes hydrolysis follow ed by decarboxylation ... 

Nitromethane is more easily prepared by heating together equimolecular amounts of sodium monochloroacetate and sodium nitrite in aqueous solution sodium nitroacetate is intermediately formed and is decomposed to nitromethane and sodium bicarbonate. The latter yields sodium carbonate and carbon dioxide at the temperature of the reaction. 

Carboxymethylcelluloses (CMC). CarboxymethylceUulose [9004 2-6] (CMC) is the carboxymethyl ether of cellulose. To prepare CMC, cellulose is steeped in sodium hydroxide solution, and the so-called alkaU cellulose is treated under controlled conditions with sodium monochloroacetate to form the sodium salt of CarboxymethylceUulose and sodium chloride. Therefore, the CMC of commerce is actuaUy sodium CarboxymethylceUulose... 

In 1948 Sandoz A.G. found a more simple method of preparation [3-7]. An ethoxylated compound was reacted with a molar amount of NaOH and after that with twice a molar amount of chloroacetic acid. In 1953 a process was patented in which sodium monochloroacetate instead of chloroacetic acid was used [8]. 

In concentrated NaOH, chitin becomes alkali chitin which reacts with 2-chloroethanol to yield 0-(2-hydroxyethyl) chitin, known as glycol chitin this compoimd was probably the first derivative to find practical use (as the recommended substrate for lysozyme). Alkali chitin with sodium monochloroacetate yields the widely used water-soluble 0-carboxymethyl chitin sodium salt [118]. The latter is also particularly susceptible to lysozyme, and its oUgomers are degraded by N-acetylglucosaminidase, thus it is convenient for medical appHcations, including bone regeneration. 

A new industrial process based on the reaction of sodium monochloroacetate with aqueous alkyl polyglycoside (without additional solvents) enables the manufacturing of this product in an economically and ecologically favorable way (Fig. 4.16). 

To prepare croscarmellose sodium, crude cellulose is steeped in sodium hydroxide solution [1] and treated with sodium monochloroacetate to form carboxymethylcellu-lose sodium. After completion of the reaction, the excess sodium monochloroacetate slowly hydrolyzes to glycolic acid. The glycolic acid converts a few of the sodium earboxymethyl groups to the free acid and catalyzes the cross-linkage to form croscarmellose sodium. The by-products sodium chloride and sodium glycolate can be removed by extraction with alcohol to achieve 99.5% purity. Croscarmellose sodium may be milled to break the polymer fibers into shorter lengths and hence improve flow properties. 

Although numerous technical improvements in the production of carboxymethylcellulose are continually appearing in the patent literature,311 the basic reaction is essentially unchanged from that devised by Jansen1 and later improved by Chowdhury4 and Hoppler,6 in which cellulose (ROH) is steeped in caustic soda, and the alkali-cellulose is etherified by sodium monochloroacetate to form sodium carboxymethylcellulose plus sodium chloride. The reaction may be simply represented as follows. 

Two methods have been reported for the synthesis of EDTA. The first method involves condensation of ethylenediamine with sodium monochloroacetate with the aid of sodium carbonate. An aqueous solution of the reactants is... 

In both its acid form and its salt forms (e.g. sodium monochloroacetate), MCA is highly toxic to the skeletal muscles, the renal system and cardiovascular system and is rapidly absorbed through the skin and mucous membranes. 

The last step in its synthesis is the condensation of sodium monochloroacetate with 2,4,5-trichlorophenol. The preparation of the latter from the inactive hexachlorocyclohexane (BHC) isomers has been described by Galat (1952). 

Acetic acid, chloro-. sod Acetic acid, ohioro-. sodium salt Caswell No. 755A Chloroctan sodny Dow defoliant EPA Pesticide Chemical Code 355200 Monoxone SMA SMCA Sodium chioroacetate Sodium monochloroacetate UN2569. Used as a herbicide. White crystals soluble in H2O (85 g/100 ml at 20 LDsO (rat orl) = 76 mg/kg. (mus orl) = 255 mg/kg. (gpg orl) = 80 mg/kg. Atlas Interlates Ltd Rhdne-Poulenc Syngenta Crop Protection. 

When sodium monochloroacetate is desired, the molten MCA from the MCA or MC receivers is delivered to plastic-coated cast-iron neutralizers (Pig. 6-15). Mother liquor from a previous charge is added, and then the equivalent sodium carbonate is run in steadily by screw feed. The resulting slurry is pumped from a bottom discharge line to holding tanks feeding a centrifugal. 

In the next reaction step, the imidazoline is car-boxymethylated with chloroacetic acid (MCA) or sodium monochloroacetate in alkaline aqueous solution. Depending on the reaction conditions, this step results in sodium amphomonoacetate or sodium amphodiacetate. 

The raw materials are cotton linters, soft wood pulp or dissolving pulp. They must be high in alpha - cellulose content, free of metals and uniformly absorb water and the NaOH solution. The other starting materials include alkylene oxides and alkyl chlorides for the preparation of nonionic cellulose ethers and sodium monochloroacetate for anionic types such as sodium carboxymethyl cellulose. 

Cocamidopropyldimethyl amine can be prepared from whole coconut oil, coconut fatty acid, or methyl esters either whole cut or stripped of the C6-C10 chain fractions. The aforementioned tertiary amines are converted to betaines by reaction with sodium monochloroacetate (SMCA) in a relatively dilute aqueous system (Scheme 1.1). 

Synthesis of imidazolinium amphoteric surfactants was reported in a patent awarded to Manheimer in 1950 [10], in which l-(2-hydroxyethyl)-2-alkyl-2-imidazoline (hereafter called imidazoline) was reacted with sodium monochloroacetate (SMCA). The Miranol company was the first to engage in large-scale production of these products in 1947, and it was around that time when Miranol s products came to be recognized for their mildness and ability to reduce the irritation of anionic surfactants. 

Four nitropyrenes (1-nitropyrene, 1,3-, 1,6-, and 1,8-dinitrt iyrene) were isolated from aiibome particulates and separated in 17 min on a 40°C C]g column (electrochemical detector, 0.60 V vs. Ag/AgCI) using a 70/30 acetonitrile/water (10 mM sodium monochloroacetate at pH 4.7) mobile phase [937]. A plot of response versus pH showed a distinct maximum at 4.7. Working curves from 0.006 to 1.6 pg/mL (analyte dependent) and detection limits of 20 pg injected were reported. 

Carboxymethyl guar Not permitted In food Guar gum Sodium monochloroacetate Printing pastes (reactive dyestuffs)... 

Sodium carboxymethylcellulose is prepared from alkaU cellulose and sodium monochloroacetate. The reaction may be represented as follows ... 

Carboxymethyl cellulose sodium By treating wood pulp with alkaU followed by reaction with sodium monochloroacetate Binder, Disintegrant... 

Koshti and Naik (2003) Sodium monochloroacetate Alkylamido betaine LC... 

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