P-Propiolactone

Data were last reviewed in lARC (1974) and the compound was classified in lARC Monographs Supplement 7 (1987). 

57-57-8 Chem. Abstr. Name-. 2-Oxetanone 

Synonyms-. Hydracrylic acid, 3-lactone 3-hydroxypropionic acid, lactone 3-hydroxypropionic acid, P-lactone propanol ide 3-propanolide propiolactone 3-propiolactone P-propionolactone 

2 Structural and molecular formulae and relative molecular mass 

No information on the global production of (3-propiolactonc was available to the Working Group. 

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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. 

Reaction with Lactones. Hydroxycarboxyhc acid ester complexes of titanium are formed by reaction of a tetraalkyl titanate with a lactone, such as P-propiolactone, y-butyrolactone, or valerolactone (35). For example. 

Beta-Propiolactone. p-Propiolactone [57-57-8] was reported to be 4000 times more active than ethylene oxide, and 25 times more... 

The same considerations apply to polycaprolactone, with living alkoxide sites. Care has to be taken to minimize reshuffling and/or backbiting78). This implies initiation at low temperature and induced protonic deactivation at conversions around 30 %. The case of poly(P-propiolactone) is quite different as the active sites are carbox-ylates79) functionalization by the method indicated is not feasible. 

Slomkowski, S., and Penczek, S., Influence of dibenzo-18-crown-6 ether on the kinetics of anionic polymerization of p-propiolactone, Macromolecules, 9, 367-369, 1976. 

Thermodynamics of fusion of poly-p-propiolactone and poly-e-caprolactone. Comparative analysis of the melting of aliphatic polylactone and polyester chains, Eur. Polym. J.. 8, 449-463, 1972. 

P-parinaric acid, physical properties, 5 33t P-pentenoic acid, physical properties, 5 3 It P-peroxylactones, 18 484 Beta phase titanium, 24 838 in alloys, 24 854-856 properties of, 24 840, 941 P-phellandrene, 24 493 P-picoline, 21 110 from acrolein, 1 276 uses for, 21 120 P-pinene, 3 230 24 496-497 major products from, 24 478 /-menthol from, 24 522 as natural precursor for aroma chemicals, 3 232 terpenoids from, 24 478-479 P-propiolactone, polymerization of, 14 259 P-quartz solid solution, 12 637—638 Beta ratio, in filtration, 11 329—330 Beta (P) rays, 21 285 P-scission reactions, 14 280-281 P-skytanthine, 2 101 P-spodumene solid solution, 12 638-639 P-sulfur trioxide, 23 756 P-sultones, 23 527 P-tocopherol, 25 793 P-tocotrienol, 25 793 P-vinylacrylic acid, physical properties, 5 33t... 

Property taxes, 9 533-534 Property-temperature relationships, of vitreous silica, 22 416-417 P-Propiolactone, polymerization of, 14 259 Propiolic acid, 5 34t Propionaldehyde... 

Methyl acrylate is also produced by the carboxylation of acetylene in aqueous methanol, by the dehydration of methyl lactate and by the methanolysis of p-propiolactone or acrylic acid. 

Yields are variable, but the reaction appears to be promoted by the presence of alkoxymethyl substituents on the oxirane ring. Reactions with p-propiolactones give lower yields (<10%). Cyclic carbonates can also be obtained from the zinc(II) promoted reaction of oxiranes with carbon dioxide [62] the stereochemistry of substituents on the oxirane are retained in the carbonate. 

The reaction of P-propiolactone with wood can be catalysed by acid or base, to yield two different products (Figure 4.12). 

Chemical/Physical. Slowly hydrolyzes to hydracrylic acid (Windholz et al., 1983). In a reactor heated to 250 °C and a pressure of 12 mmHg, p-propiolactone decomposed to give equal amounts of ethylene and carbon dioxide (James and Wellington, 1969). 

Benzyp3U ene, see Benzojajpyrene Beosit, see a-Endosulfan, p-Endosulfan Bercema NMC50, see Carbaryl Betaprone, see p-Propiolactone Bexol, see Lindane... 

EPA pesticide chemical code 000169, see Amyl acetate EPA pesticide chemical code 000601, see Acrylonitrile EPA pesticide chemical code 000701, see Acrolein EPA pesticide chemical code 001502, see sec-Butyl alcohol EPA pesticide chemical code 004101, see Acetone EPA pesticide chemical code 005302, see Ammonia EPA pesticide chemical code 008801, see Benzene EPA pesticide chemical code 009001, see Lindane EPA pesticide chemical code 009101, see Benzoic acid EPA pesticide chemical code 009502, see Benzyl alcohol EPA pesticide chemical code 009601, see Oxalic acid EPA pesticide chemical code 010901, see p-Propiolactone EPA pesticide chemical code 011301, see l,2-Dibromo-3-chloropropane... 

Hydracrylic acid p-lactone, see p-Propiolactone Hydralin, see Cyclohexanol Hydrazine-benzene, see Phenylhydrazine Hydrazinobenzene, see Phenylhydrazine Hydrazobenzene, see 1,2-Diphenylhydrazine l,T-Hydrazobenzene, see 1,2-Diphenylhydrazine Hydrazodibenzene, see 1.2-Diphenylhydrazine Hydrazomethane, see Methylhydrazine Hydrindane, see Indan... 

Hydroxyphenol, see Hydroquinone p-Hydroxyphenol, see Hydroquinone 4-Hydroxy-3-(l-phenyl-3-oxobutyl)coumarin, see Warfarin 1 -Hydroxypropane, see 1 -Propanol 3 Hydroxypropene, see Allyl alcohol 3 Hydroxypropionic acid lactone, see p-Propiolactone... 

Oxa-4-azacyclohexane, see Morpholine 3-Oxa-l-butanol, see Methyl cellosolve Oxacyclopentane, see Tetrahydrofuran 3-Oxa-l-heptanol, see 2-Butoxyethanol Oxetan-2-one, see p-Propiolactone... 

Oxetanone, see p-Propiolactone Oxidation base 10, see p-Phenylenediamine Oxidation base 10a, see p-Phenylenediamine Oxiranemethanol, see Glycidol Oxiranylmethanol, see Glycidol... 

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