Acetone toxicity

Compatibihty of acetone with other materials should be carefliUy considered, especially in disposal of wastes. It reacts with chlorinating substances to form toxic chloroketones, and potentially explosively with some peroxy compounds and a number of oxidizing mixtures. Mixed with chloroform, acetone will react violently in the presence of bases. Other incompatibilities ate Hsted in the Sax handbook (53). 

Acrolein is a highly toxic material with extreme lacrimatory properties. At room temperature acrolein is a Hquid with volatiUty and flammabiUty somewhat similar to acetone but unlike acetone, its solubiUty in water is limited. Commercially, acrolein is always stored with hydroquinone and acetic acid as inhibitors. Special care in handling is required because of the flammabiUty, reactivity, and toxicity of acrolein. 

CeUulose triacetate is insoluble in acetone, and other solvent systems are used for dry extmsion, such as chlorinated hydrocarbons (eg, methylene chloride), methyl acetate, acetic acid, dimethylformamide, and dimethyl sulfoxide. Methylene chloride containing 5—15% methanol or ethanol is most often employed. Concerns with the oral toxicity of methylene chloride have led to the recent termination of the only triacetate fiber preparation faciHty in the United States, although manufacture stiH exists elsewhere in the world (49). 

Health and Safety Factors. MEK is slightly more toxic than acetone, but is not considered highly toxic, and nor does it exhibit cumulative toxicological properties. The OSHA time weighted average iu air is 200 ppm other measured toxicity values are shown iu Table 3. Methyl ethyl ketone is highly flammable. 

Solubility and Solvent Resistance. The majority of polycarbonates are prepared in methylene chloride solution. Chloroform, i7j -l,2-dichloroethylene, yy -tetrachloroethane, and methylene chloride are the preferred solvents for polycarbonates. The polymer is soluble in chlorobenzene or o-dichlorobenzene when warm, but crystallization may occur at lower temperatures. Methylene chloride is most commonly used because of the high solubiUty of the polymer (350 g/L at 25°C), and because this solvent has low flammabiUty and toxicity. Nonhalogenated solvents include tetrahydrofuran, dioxane, pyridine, and cresols. Hydrocarbons (qv) and aUphatic alcohols, esters (see Esters, organic), or ketones (qv) do not dissolve polycarbonates. Acetone (qv) promotes rapid crystallization of the normally amorphous polymer, and causes catastrophic failure of stressed polycarbonate parts. 

The handling of toxic materials and disposal of ammonium bisulfate have led to the development of alternative methods to produce this acid and the methyl ester. There are two technologies for production from isobutylene now available ammoxidation to methyl methacrylate (the Sohio process), which is then solvolyzed, similar to acetone cyanohydrin, to methyl methacrylate and direct oxidation of isobutylene in two stages via methacrolein [78-85-3] to methacryhc acid, which is then esterified (125). Since direct oxidation avoids the need for HCN and NH, and thus toxic wastes, all new plants have elected to use this technology. Two plants, Oxirane and Rohm and Haas (126), came on-stream in the early 1980s. The Oxirane plant uses the coproduct tert-huty alcohol direcdy rather than dehydrating it first to isobutylene (see Methacrylic acid). 

Methyl amyl ketone, derived from the crossed aldol condensation of -butyraldehyde and acetone, is used predominandy as a high soHds coatings solvent. It is also employed as a replacement for the very toxic 2-ethoxyethyl acetate [111 -15-9J. 

Cellulose acetate [9004-35-7] is the most important organic ester because of its broad appHcation in fibers and plastics it is prepared in multi-ton quantities with degrees of substitution (DS) ranging from that of hydrolyzed, water-soluble monoacetates to those of fully substituted triacetate (Table 1). Soluble cellulose acetate was first prepared in 1865 by heating cotton and acetic anhydride at 180°C (1). Using sulfuric acid as a catalyst permitted preparation at lower temperatures (2), and later, partial hydrolysis of the triacetate gave an acetone-soluble cellulose acetate (3). The solubiUty of partially hydrolyzed (secondary) cellulose acetate in less expensive and less toxic solvents such as acetone aided substantially in its subsequent commercial development. 

Insecticide methomyl is a very toxic pesticide and is highly soluble in water (57.9 g/1). It has a low sorption affinity to soil and can cause groundwater and surface water contamination in agricultural areas. Solubilities of methomyl in different solvents are in methanol 1000 g/1, in aceton 730 g/1, in ethanol 420 g/1, in isopropanol 220 g/1, in toluene 30 g/1. 

V-Allylthiourea (thiosinamine) [109-57-9] M 116.2, m 70-73 , 78 . Recrystd from H2O. Soluble in 30 parts of cold H2O, soluble in EtOH but insoluble in "CeHg. Also recrystd from acetone, EtOH or ethyl acetate, after decolorising with charcoal. The white crystals have a bitter taste with a slight garlic odour and are TOXIC. [Anal Chem 21 421 7949.]... 

Benzoyl suinde [644-32-6] M 174.4, m 131.2-132.3 . About 300mL of solvent was blown off from a filtered soln of benzoyl disulfide (25g) in acetone (350mL). The remaining acetone was decanted from the solid which was recrystd first from 300mL of 1 1 (v/v) EtOH/ethyl acetate, then from 300mL of EtOH, and finally from 240mL of 1 1 (v/v) EtOH/ethyl acetate. Yield about 40% [Pryor and Pickering J Am Chem Soc 84 2705 7962]. Handle in a fume cupboard because o/TOXICITY and obnoxious odour. 

Acetone cyanohydrin (Oxyisobutyric nitrile) (CH3)2C(0H)CN Highly toxic by inhalation or ingestion Irritating and moderately toxic upon skin contact Readily decomposes to HCN and acetone at 1 20°C, or at lower temperatures when exposed to alkaline conditions Colourless combustible liquid Elash point 73°C Ignition temperature 68.7°C Completely soluble in water... 

Solvents acetone, methyl ethyl ketone (MEK), toluene, xylene, glycol, ethers, alcohol defats and dries skin some may be absorbed may carry other components through skin high volatility, exposure possible irritation central nervous system depression (e.g. dizziness, loss of coordination) low to high toxicity, longterm effects... 

Because osmium tetroxide is expensive, and its vapors are toxic, alternate methods have been explored for effecting vic-glycol formation. In the aliphatic series, olefins can be hydroxylated with hydrogen peroxide with the use of only a catalytic amount of osmium tetroxide. Anhydrous conditions are not necessary 30% hydrogen peroxide in acetone or acetone-ether is satisfactory. The intermediate osmate ester is presumably cleaved by peroxide to the glycol with regeneration of osmium tetroxide. When this reaction was tried on a A -steroid, the product isolated was the 20-ketone ... 

Sodium azide (Eastman, 97-99%) is activated by dissolving 100 g of the salt in 400 ml of distilled water and stirring with 14 ml of hydrazine hydrate for 15 min. The solution is filtered and added dropwise to 4 liters of rapidly stirred, dry acetone. The solid is collected by filtration and washed with 150 ml of dry acetone. The fine powder (57-85 g) is dried under vacuum at 50° for 2 hr. Sodium azide is extremely toxic and the fine powder should be handled with care to avoid breathing the dust. 

Ascher and Nemny 495) found that residues of triphenyltin acetate on glass, resulting from the evaporation of acetone solutions thereof, were, on contact to houseflies, less toxic with rising concentration. As triphenyltin acetate is likely to be a self-associated polymer in the solid state [similar to trimethyltin acetate (355)] and in concentrated solutions, it was suggested 495) that the monomer, which exists in dilute solutions, is toxic to insects, and the polymer, nontoxic. Interestingly, in this connection, a triphenyltin methacrylate copolymer has 470) a very low mammalian toxicity (acute, oral LDso for mice >2000 mg/kg). 

Areas for handling toxic or flammables should be segregated. A chemical like acetone, for example, should never be handled in the vicinity of an open heat source. Work wth highly toxic materials should be strictly confined to designated areas. Many operations must be performed in fume hoods. For others, only improved ventilation may be required. 

Haggard HW, Greenberg LA, Turner JA. The physiological principles governing the action of acetone together with determination of toxicity. J Ind Hyg Toxicol 1944 26 133-51. 

Acetone is flammable. It is slightly toxic by ingestion and inhalation. 

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