6-Chloropropionic acid

Nitroethane may be similarly obtained from sodium a chloropropionate. This is a general reaction for a chloro carboxylic acids, but in practice only monochloroacetic acid and a chloropropionic acid are readily available. 

Quaternary salts (33) obtained from aminothiazole derivatives liberate 2-imino-4-thiazolines in basic medium (Scheme 24). This reaction is general and independent of the nature of R in 33 (160-167). The same result was found when 2-propynylbromide (168) or 3-chloropropionic acid (169) were the quaternizing reagents. This method is particularly... 

Batchwise operated multipurpose plants are per defmitionem the vehicle for the production of fine chemicals. There are, however, a few examples of fine chemicals produced ia dedicated, coatiauous plants. These can be advantageous if the raw materials or products are gaseous or Hquid rather than soHd, if the reaction is strongly exothermic or endothermic or otherwise hazardous, and if the requirement for the product warrants a continued capacity utilization. Some fine chemicals produced by continuous processes are methyl 4-chloroacetoacetate [32807-28-6] C H CIO [32807-28-6], and malononittile [109-77-3] C2H2N2, made by Lonza dimethyl acetonedicarboxylate [1830-54-2] made by Ube and L-2-chloropropionic acid [107-94-8] C2H C102, produced by Zeneca. 

Other possible chemical synthesis routes for lactic acid include base-cataly2ed degradation of sugars oxidation of propylene glycol reaction of acetaldehyde, carbon monoxide, and water at elevated temperatures and pressures hydrolysis of chloropropionic acid (prepared by chlorination of propionic acid) nitric acid oxidation of propylene etc. None of these routes has led to a technically and economically viable process (6). 

Among other mercaptocarboxyhc acids, the mercaptopropionic acids have undergone a promising development. Thiolactic acid or 2-mercaptopropionic acid [79 2-5] HSCH(CH2)COOH, is manufactured by usiag 2-chloropropionic acid [598-78-7]. 3-Mercaptopropionic acid [107-96-0] HSCH2CH2COOH, competes with thioglycohc acid ia plastic additives or as modifiers ia various polymers. Mercaptopropionic acid is... 

After the chlorohydrin has been added the mixture is stirred for one-half hour longer, allowed to stand overnight, heated for one hour on the steam bath, and distilled as directed. The yield of /3-chloropropionic acid boiling at io7-rog°/20 mm. and freezing at 39° is 179-181 g. (78-79 per cent of the theoretical amount). 

Bromophenol blue (3.0...4.6) aliphatic carboxylic acids [225 — 228] malonic and lactic acids [229] palmitic and lactic acids [230] malonic, glycolic, malic, citric, tartaric, ketoglutaric, galacturonic and oxalic acids [196] dicarboxylic acids, succinic acid [231] indoleacetic acid, trichloroacetic acid [232] palmitic acid, palmityl- and stearyllactic acid [223] benzoic, sorbic and salicylic acid [234] metabolites of ascorbic acid [235] chloropropionic acid [236] oligogalacturonic acids [237] amino acids, hydrocarbons, mono-, di- and triglycerides [238] xylobiose, xylose, glucose and derivatives [239] sugar alcohols [91] toxaphene [240]... 

Merck and Maeder have patented the manufacture of arecaidine by loss of water from l-methyl-4-hydroxypiperidine-3-carboxylic acid. A method of producing the latter has been describd by Mannich and Veit and has been developed by Ugriumov for the production of arecaidine and arecoline. With the same objective, Dankova, Sidorova and Preobrachenski use what is substantially McElvain s process,but start by converting ethylene oxide, via the chlorohydrin and the cyanohydrin, into -chloropropionic acid. The ethyl ester of this with methylamine in benzene at 140° furnishes methylbis(2-carbethoxyethyl) amine (I) which on refluxing with sodium or sodium Moamyloxide in xylene yields l-methyl-3-carbethoxy-4-piperidone (II). The latter is reduced by sodium amalgam in dilute hydrochloric acid at 0° to l-methyl-3-carbethoxy-4-hydroxypiperidine (III) which on dehydration, and hydrolysis, yields arecaidine (IV R = H), convertible by methylation into arecoline (IV R = CH3). 

The reaction mixture may also be worked up by pouring it into water and extracting the 0-chloropropionic add with ether. This is less satisfactory as the nitric add is lost and some of the /3-chloropropionic acid remains in the water. 

J-Chloropropionic acid has been prepared by the hydrolysis of ethylene cyanohydrin with hydrochloric acid,1 and by the oxidation of /S-chloropropionaldehyde2 or of trimethylene chlorohydrin 3 by nitric acid. 

The /3-chloropropionic acid is best isolated by direct distillation under reduced pressure (Note 1) using a 250-cc. modified Claiscn flask (Org. Syn. 1, 40). The nitric acid is collected up to ioo°/2omm. using a water condenser. The condenser is then removed and the residual /3-chloropropionic acid is fractionated, collecting as pure product the portion boiling at 105-107720mm. The yield is 3i 3i.5g. (S4—55 Per cent of the theoretical amount) (Note 2). The product solidifies on cooling and melts at 41 41.5°. 

Chloroplast pigments 303 Chloropropham 108 Chloropropionic acid 45 Chlorothymol 67 a-Cholestanol 43,65 5-a-Cholestan-3-one 43, 334—336, 421, 422... 

CjHgO Dimethyl ether CaHgCtOj 2-Chloropropionic acid... 

The metabolism of carfentrazone-ethyl in animals and plants is similar. The major plant metabolites are carfentrazone-chloropropionic acid (C-CI-PAc), 3-desmethylcarfentrazone-chloropropionic acid (DM-C-CI-PAc), and 3-hydroxymethylcarfentrazone-chloropropionic acid (HM-C-CI-PAc). The major animal metabolites are carfentrazone-chloropropionic acid (C-CI-PAc) and carfentrazone-propionic acid (C-PAc). The tolerance expression for livestock and plant commodities is carfentrazone-ethyl plus the ester hydrolysis product, C-CI-PAc. 

The selective inclusion properties of 40 (Table 6) offer several possibilities of compound separation which are of interest in analytics and for preparation purposes37). The separation of methanol from a mixture with ethanol, or of propionic aldehyde from propionic acid, or of 2-chloropropionic acid from propionic acid or lactic acid, etc., are a few examples. 

It is of interest that reaction of methyl, benzyl, and p-nitrophenyl 2-acetamido-4,6-0-benzylidene-2-deoxy-/3-D-glucopyranosides, and also the corresponding methyl a-D-glucopyranoside derivative, with ( )-2-chloropropionic acid gave, in preponderant yields, the respective 3-0-(D-l-carboxyethyl) derivatives257 only from the last-mentioned reaction was a significant amount of the 3-0-(L-l-carboxy-ethyl) derivative isolated. 

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