3- propenoic acids hydrolysis

So-called pure acryUc latexes are employed for maximum durabiUty as required, for example, in high performance exterior latex paints. On the other hand, interior flat wall latex paints do not need the high resistance to exterior exposure and hydrolysis. The most widely used latexes for this appHcation are vinyl acetate copolymer latexes such as vinyl acetate/butyl acrylate (2-propenoic acid butyl ester) [141-32-2] copolymers having just sufficient... 

Acidic and basic hydrolysis of ethyl 4-oxo-4//-pyrido[l, 2-u]pyrimidin-3-carboxylates gave 3-carboxylic acid derivatives (OlMIPl). Stirring rerr-butyl ( )-3-(2-hydroxy-8-[2-(4-isopropyl-l, 3-thiazol-2-yl)-l-ethenyl]-4-oxo-4//-pyrido[l,2-u]pyrimidin-3-yl)-2-propenoate in CF3CO2H at room temperature yielded ( )-3-substituted 2-propenoic acid. 

As shown in scheme 1, (S)-amide 2 (ref. 4) obtained from ethyl ester of (S)-proline, chiral auxiliary and 2-substituted-2-propenoic acids 1 are bromolactonized with N-bromosuccinimide (NBS)-DMF, followed by hydrolysis with 6N-HC1 to afford (S)-4. The results are summarized in Table 1. 

Lipases are the enzymes for which a number of examples of a promiscuous activity have been reported. Thus, in addition to their original activity comprising hydrolysis of lipids and, generally, catalysis of the hydrolysis or formation of carboxylic esters [107], lipases have been found to catalyze not only the carbon-nitrogen bond hydrolysis/formation (in this case, acting as proteases) but also the carbon-carbon bond-forming reactions. The first example of a lipase-catalyzed Michael addition to 2-(trifluoromethyl)propenoic acid was described as early as in 1986 [108]. Michael addition of secondary amines to acrylonitrile is up to 100-fold faster in the presence of various preparations of the hpase from Candida antariica (CAL-B) than in the absence of a biocatalyst (Scheme 5.20) [109]. 

Oxetan-2-one (j3-propanolactoiic) unci also oxetani-3-one are known, although most interest lies in the former compound. It is a carcinogen, possibly because it can alkylate guanidine, one of the constituent bases of nucleic acids. On standing, oxetan-2-one slowly polymerizes, and on pyrolysis it forms propenoic acid (Scheme 8.13). Alkaline hydrolysis gives a salt of 3-hydroxypropanoic acid. 

Halocyclization of the amide 5 (R1 = C6H5 R2 = H R3 = CH3), derived from (S)-proline and ( )-2-methyl-3-phenyI-2-propenoic acid, can be performed by stirring a mixture of the potassium salt of 5 and 2 equivalents of TV-bromosuccinimide in dimethylformamide for 48 hours. This results in a 99 1 (transjeis) mixture of lactones 6 in 91 % yield1. Debromination of the crude lactone, followed by acidic hydrolysis, gives ( + )-(/ )-2-hydroxy-2-methyl-3-phenylpropanoic acid fmp 115-117 °C [a]D + 16.7 (c = 5.71, dioxane)3] in 36% overall yield. Other bromolactones 6 can be similarly prepared from the corresponding (S)-7V-(a,/l-unsaturated acyl)prolines 5. 

Besides water, another small molecule in the pyrolysate is CO2. This small molecule may be eliminated by various mechanisms including a hydrolysis of the amide groups with the formation of acrylic acid, followed by decarboxylation. Some small peaks In the pyrolysis of polyacrylamide are identical with those from poly(acrylic acid). Even traces of propanoic acid and propenoic acid are present in the acrylamide pyrolysate. A comparison between a time window 25.0 min. to 70 min. from the pyrogram of poly(acrylic acid) and from the pyrogram of polyacrylamide is shown in Figure 6.7.17. 

Methacrylic acid me-tho- kri-lik- [ISV] (1865) (a-methacrylic acid, 2-methyl-2-propenoic acid) n. CH2=C(CH3)COOH. A colorless liquid prepared by the acid hydrolysis of acetone, from which are derived all of the methacrylate compounds. Most important of these are the esters, especially methyl methacrylate. 

---