Carcinogenicity propiolactone

Ketene Process. The ketene process based on acetic acid or acetone as the raw material was developed by B. F. Goodrich (81) and Celanese (82). It is no longer used commercially because the intermediate P-propiolactone is suspected to be a carcinogen (83). In addition, it cannot compete with the improved propylene oxidation process (see Ketenes, ketene dimers, and related substances). 

P-Hydroxy acids lose water, especially in the presence of an acid catalyst, to give a,P-unsaturated acids, and frequendy P,y-unsaturated acids. P-Hydroxy acids do not form lactones readily because of the difficulty of four-membered ring formation. The simplest P-lactone, P-propiolactone, can be made from ketene and formaldehyde in the presence of methyl borate but not from P-hydroxypropionic acid. P-Propiolactone [57-57-8] is a usehil intermediate for organic synthesis but caution should be exercised when handling this lactone because it is a known carcinogen. 

US Department of Health and Human Services (NIOSH) Occupational safety and health guidelines for chemical hazards—Supplement II— OHG (Pub No. 89-104), pp 1-6. Occupational safety and health guideline for P propiolactone potential human carcinogen. Cincinnati, OH, 1988... 

P-Propiolactone was tested for carcinogenicity in mice by skin application and subcutaneous or intraperitoneal injection and in rats by inhalation exposure and subcutaneous injection, producing local tumours. The results obtained in studies in hamsters and guinea-pigs were equivocal. 

No epidemiological data relevant to the carcinogenicity of 3-propiolactone were available. 

There is sufficient evidence in experimental animals for the carcinogenicity of P-propiolactone. 

Baturay. N. Kennedy, A.R. (1986) Pyrene acts as a cocarcinogen with the carcinogens benzo[o]pyrene, P-propiolactone and radiation in the induction of malignant transformation in cultured mouse fibroblasts soybean extract containing the Bowman-Birk inhibitor acts as an anticarcinogen. Cell Biol. Toxicol., 2, 21-32... 

Rees, E.D., Shuck, A.E., Lowry, J.Q., Smith, T.M. Lipscomb, H. (1979) Comparison of the clastogenic and carcinogenic effects of intravenous p-propiolactone and benzo(a)pyrene in rats. J. environ. Pathol. Toxicol., 2, 1475-1485... 

P-Propiolactone [57-57-8] M 72.1, b 83°/45mm, d 1.150, n25 1.4117. Fractionally distd under reduced pressure, from sodium. CARCINOGEN. 

Chemical (vapor phase) Ethylene oxide Propylene oxide Formaldehyde (3 - Propiolactone Disinfection temperature Ethylene oxide also used as sterilizing agent Possible carcinogenic activity of p-propiolactone... 

The preparation of (3-propiolactone involves bubbling an equimolar mixture of gaseous ketene and formaldehyde into a solution of (3-PL containing a small amount of a complex catalyst composed of AlCl3 and ZnCl2. (3-PL is a carcinogenic compound and has to be handled with care. 

Among the various chemicals to form ether bonds with hydroxyl groups in wood, a high decay resistance of wood treated with P-propiolactone [25] and acrylonitrile [26,27], both at 25% WPG, has been reported earlier. However, an undesirable carcinogenic effect in (J-propiolactone as well as loss of impact strength and low ASE in acrylonitrile-treated wood discouraged further works on these treatments [7]. 

SAFETY PROFILE Moderately toxic by ingestion, intravenous, and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data by skin contact. Mutation data reported. Less acutely toxic than p-propiolactone. Combustible when exposed to heat or flame can react with oxidizing materials. To fight fire, use foam, alcohol foam, CO2, dry chemical. Potentially explosive reaction with butanol + 2,4-dichlorophenol + sodium hydroxide. When heated to decomposition it emits acrid and irritating fumes. 

The major problem in p-propiolactone reactions is that p-pro-piolactone has been labeled a very active carcinogen. For this reason, little future research can be expected on this chemical. It would be interesting, however, to look at this chemical reaction under the basic conditions that produce ester formation. 

Oxetan-2-one (p-propiolactone, propan-3-olide) [57-57-8] M 72.1, m -31.2°, -35 , b 51°/10mm, 83°/45mm, d f 1.1460, n d 1.4117. Fractionally distil the lactone from sodium under reduced pressure. It gives an acidic solution in H2O. It irritates the skin and is a possible carcinogen. Beilstein 171130,17 111/TV 4157.]... 

Carcinogen May cause cancer lA, IB Danger Known or presumed human carcinogen Benzidine, 2-naphthylamine, dimethylni- trosamine, bis(chloromethyl) ether, ethylenimine, nickel carbonyl, /3-propiolactone, vinyl chloride... 

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