Hydracrylic acid

Hydracrylic acid CH2OH—CH2—CO OH /5-Hydroxy propionic acid 

Propionic acid plainly yields two isomeric hydroxy acids, viz., an alpha- and a e/o-acid. The constitution of the two compounds is, 

We have just spoken of the different action of the alpha-, beta-, and gowwo-halogen acids toward alkalies (p. 233), and of the similar different action of the alpha-, beta-, and gamma-hydioxy acids when dehydrated (p. 241). The second of the above acids, viz., the /3-hydroxy propionic acid, shows the reaction characteristic of eto-acids. On heating, or by the action of sulphuric acid, it loses water and is converted into the corresponding ethylene unsaturated acid, propenoic acid, as follows  

Propenoic acid is commonly known as acrylic acid (p. 172), and j(3-hydroxy propionic acid is therefore named hydracrylic acid, i.e., hydrated acrylic acid. 

Synthesis from Acrylic Acid.—Three methods of synthesis of hydra-crylic acid show its relation to acrylic acid, to propionic acid and to ethylene. When acrylic acid is. heated with sodium hydroxide to loo it takes up a molecule of water and yields hydracrylic acid. The reaction is simply the reverse of the one above. 

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Chemical Designations - Synonyms Betaprone Hydracrylic acid, beta-lactone 2-Oxetanone Propanolide beta-Propionolactone Chemical Formula OCH2CH2CO. 

This compound may be produced by reacting o-chlorobenzophenone with acetonitrile in the presence of sodium amide or another strongly basic condensing agent, to form the nitrile of /3-phenyl-/3-o-chlorophenyl-hydracrylic acid, which is then hydrogenated to yield Tphenyl-l-o-chlorophenyl-S-aminopropanol-l. The latter intermediate compound is subsequently dimethylated with an agent such as methyl sulfate to provide the desired end product l-o-chlorophenyl-Tphenyl-S-dimethylaminopropanol. 

Synonyms AI3-24257 AIDS-6024 Betaprone BPL BRN 0001360 Caswell No. 709 CCRIS 536 EINECS 200-340-1 EPA pesticide chemical code 010901 Hydracrylic acid p iactone 3-Hydroxypropionic acid lactone p Lactone NSC 21626 Oxetan-2-one 2-Oxetanone Propano-lide Propiolactone 1,3-Propiolactone 3-Propiolactone p Propionolactone 3-Propionolactone p Propro-lactone UN 2810. 

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). 

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... 

Hydracrylic acid, see p-Propiolactone Hydrazobenzene, see Aniline Hydriodic acid, see Methyl iodide Hydrobromic acid, see Bromodichloromethane, Bromoform, Methyl bromide, Metobromuron Hydrochloric acid, see Alachlor. Aldrin, Benzyl chloride, a-BHC, p-BHC, Bis (2-chloroethyl) ether, Bis(2-chloroisopropyl) ether, Bromacil. Bromodichloromethane, Carbon tetrachloride, Chloroethane, Chloroform, o-Chloronitrobenzene. Chloropicrin, Chloroprene, p-Chloronitrobenzene, 2,4-D, see Dalanon-sodium. p.p -DDD, p,p -DDT, Dicamba. 1,1-Dichloroethane, 1,1-Dichloroethylene, fratts-l,2-Dichloroethylene, s/m-Dichloromethyl ether, 2.3-Dichloronitrobenzene. 3.4-Dichloronitrobenzene. 1,2-Dichloropropane, cis-1,3-... 

The chief methods for the preparation of /3-bromopropionic acid are the action of hydrobromic acid on acrylic acid,1 on hydracrylic acid,2 and on ethylene cyanohydrin 3 the oxidation of /3-bromopropionaldehyde 4 and of trimethylene bromohydrin 5 with nitric acid. 

Hydracrylic Acid, Beta-Lactone Beta-Prop Iolactone... 

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

Hydracrylic acid or -hydroxy-propionic acid A hydroxymono-carboxvlic acid... 

Hi HYDRACRYLIC ACID, t - I-2-HETHYL-2-PHEHYL-. 3-alpha-TROPANYL ESTERi HYDROCHLORIDE... 

Oxetanone, hydracrylic acid (3-lactone, P propionolactone, propanolide, NSC-21626, Betaprone. 

ETHYL P-HYDROXY-P.P-DIPHENYLPROPIONATE (Hydracrylic acid, 3,3-diphenyl, ethyl ester)... 

Hydracrylic Acid (Ethylenelactic Acid=/3-oxypropionic Acid). —Resin and a little formic acid were found present in the electrolyte surrounding the positive pole. 

Sodium succinate and sodium perchlorate, electrolyzed, by Hofer and Moest,2 gave hydracrylic acid as the chief product, besides acetaldehyde, acetic acid, methyl alcohol, and formic acid. The splitting off of carbonic acid and the introduction of the hydroxyl group occurs only at one carboxyl group ... 

There is no evidence at hand as to whether the intermediate product is hydracrylic acid or ClCH2CHaCN, or both, although it is known that ji-chloropropionic acid can be prepared from the former.5... 

Other Syntheses. Acrylic acid and other unsaturated compounds can also be made by a number of classical elimination reactions. Acrylates have been obtained from the thermal dehydration of hydracrylic acid (3-hydroxypropanoic acid [503-66-2]) (84), from the dehydrohalogenation of 3-halopropionic acid derivatives (85), and from the reduction of dilaalopropionates (2). These studies, together with the related characterization and chemical investigations, contributed significantly to the development of commercial orgaioic chemistry. 

Polyhydric alcohol mercaptoalkanoate esters are prepared by reaction of the appropriate alcohols and thioester usingtytoluenesulfonic acid catalyst under nitrogen and subsequent heating (16,17). Organotin mercapto esters are similady produced by reaction of the esters with dibutyltin oxide (18). Pentaeiytlnitol can be oxidized to 2,2-bis(hydroxyinethyl)hydracrylic acid [2831-90-5], C5H10O5,... 

Hydracrylic acid Propanoic acid, 3-hydroxy- Malic acid Butanedioic acid, hydroxy-... 

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