Acids reacting with

Glycerol -dichlorohydrin, 2.3-dichloro-propanol, CH2CI CHC1 CH2 0H. Colourless liquid, b.p. 182 C. Prepared by the chlorination of propenyl alcohol. Oxidized by nitric acid to 1,2-dichloropropionic acid. Reacts with NaOH to give epichlorohydrin. 

NH2-C0-NH NH2,CH5N30. Colourless crystalline substance m.p. 96" C. Prepared by the electrolytic reduction of nitrourea in 20% sulphuric acid at 10 "C. Forms crystalline salts with acids. Reacts with aldehydes and ketones to give semicarbazones. Used for the isolation and identification of aldehydes and ketones. 

Pure hydrazoic acid is a colourless liquid, b.p. 310 K. It is very ready to detonate violently when subjected to even slight shock, and so is used in aqueous solution. It is a weak acid, reacting with alkali to give azides, which contain the ion Nj. 

Dichlorophenoxyacetates. Amino acids react with 2 chlorophenoxyacetyl chloride to give crystalline derivatives ... 

Carboxylic acids react with butadiene as alkali metal carboxylates. A mixture of isomeric 1- and 3-acetoxyoctadienes (39 and 40) is formed by the reaction of acetic acid[13]. The reaction is very slow in acetic acid alone. It is accelerated by forming acetate by the addition of a base[40]. Addition of an equal amount of triethylamine achieved complete conversion at 80 C after 2 h. AcONa or AcOK also can be used as a base. Trimethylolpropane phosphite (TMPP) completely eliminates the formation of 1,3,7-octatriene, and the acetoxyocta-dienes 39 and 40 are obtained in 81% and 9% yields by using N.N.N M -tetramethyl-l,3-diaminobutane at 50 in a 2 h reaction. These two isomers undergo Pd-catalyzed allylic rearrangement with each other. 

Thiazole sulfonic acid reacts with nucleophiles leading to the corresponding 2-substituted compounds (140. 141, and 142) (Scheme 73) (39, 334). 

Wnte an equation for the Brpnsted acid-base reaction that occurs when each of the fol lowing acids reacts with water Show all unshared electron pairs and formal charges and use curved arrows to track electron movement... 

Two molecules of ammonia are needed because its acylation produces in addi tion to the desired amide a molecule of hydrogen chloride Hydrogen chloride (an acid) reacts with ammonia (a base) to give ammonium chloride... 

The balanced chemical reaction provides the stoichiometric relationship between the moles of Fe used and the moles of oxalic acid in the sample being analyzed— specifically, one mole of oxalic acid reacts with two moles of Fe. As shown in Example 2.6, the balanced chemical reaction can be used to determine the amount of oxalic acid in a sample, provided that information about the number of moles of Fe is known. 

The moles of oxalic acid reacting with the Fe, therefore, is... 

Acids react with acetic anhydride to furnish higher anhydrides (20). An acid which has a higher boiling point than acetic acid is refluxed with acetic anhydride until an equiUbrium is estabflshed. The low boiling acetic acid is distilled off and the anhydride of the higher acid is left. Adipic polyanhydride is obtained in this manner (21). 

MetaUic ions are precipitated as their hydroxides from aqueous caustic solutions. The reactions of importance in chlor—alkali operations are removal of magnesium as Mg(OH)2 during primary purification and of other impurities for pollution control. Organic acids react with NaOH to form soluble salts. Saponification of esters to form the organic acid salt and an alcohol and internal coupling reactions involve NaOH, as exemplified by reaction with triglycerides to form soap and glycerol,... 

Aqueous mineral acids react with BF to yield the hydrates of BF or the hydroxyfluoroboric acids, fluoroboric acid, or boric acid. Solution in aqueous alkali gives the soluble salts of the hydroxyfluoroboric acids, fluoroboric acids, or boric acid. Boron trifluoride, slightly soluble in many organic solvents including saturated hydrocarbons (qv), halogenated hydrocarbons, and aromatic compounds, easily polymerizes unsaturated compounds such as butylenes (qv), styrene (qv), or vinyl esters, as well as easily cleaved cycHc molecules such as tetrahydrofuran (see Furan derivatives). Other molecules containing electron-donating atoms such as O, S, N, P, etc, eg, alcohols, acids, amines, phosphines, and ethers, may dissolve BF to produce soluble adducts. 

Trifluoromethanesulfonic acid is miscible in all proportions with water and is soluble in many polar organic solvents such as dimethylformamide, dimethyl sulfoxide, and acetonitrile. In addition, it is soluble in alcohols, ketones, ethers, and esters, but these generally are not suitably inert solvents. The acid reacts with ethyl ether to give a colorless, Hquid oxonium complex, which on further heating gives the ethyl ester and ethylene. Reaction with ethanol gives the ester, but in addition dehydration and ether formation occurs. 

Formic acid forms esters with primary, secondary, and tertiary alcohols. The high acidity of formic acid makes use of the usual mineral acid catalysts unnecessary in simple esterifications (17). Formic acid reacts with most amines to form formylamino compounds. With certain diamines imida2ole formation occurs, a reaction that has synthetic utiHty (18) ... 

The formyl cation, HCO, is also likely to be an intermediate in the modification of the Koch reaction whereby formic acid reacts with olefins to give carboxyhc acids (20) ... 

In another DMF process, hydrocyanic acid reacts with methanol ia the presence of water and a titanium catalyst (16), or ia the presence of dimethylamine and a catalyst (17). 

Various electrophiles other than iodine have been used to induce alkenyl coupling (9). Alkyl haUdes and protic acids react with alkynylborates to yield mixtures of stereoisomeric alkenylboranes. Nevertheless, oxidation of these products is synthetically useful, providing single ketones (296—298). Alcohols are obtained from the corresponding alkenylborates. 

Carboxyhc acids react with aryl isocyanates, at elevated temperatures to yield anhydrides. The anhydrides subsequently evolve carbon dioxide to yield amines at elevated temperatures (70—72). The aromatic amines are further converted into amides by reaction with excess anhydride. Ortho diacids, such as phthahc acid [88-99-3J, react with aryl isocyanates to yield the corresponding A/-aryl phthalimides (73). Reactions with carboxyhc acids are irreversible and commercially used to prepare polyamides and polyimides, two classes of high performance polymers for high temperature appHcations where chemical resistance is important. Base catalysis is recommended to reduce the formation of substituted urea by-products (74). 

Nitric acid reacts with all metals except gold, iridium, platinum, rhodium, tantalum, titanium, and certain alloys. It reacts violentiy with sodium and potassium to produce nitrogen. Most metals are converted iato nitrates arsenic, antimony, and tin form oxides. Chrome, iron, and aluminum readily dissolve ia dilute nitric acid but with concentrated acid form a metal oxide layer that passivates the metal, ie, prevents further reaction. 

Oxahc acid reacts with various metals to form metal salts, which are quite important as the derivatives of oxahc acid. It also reacts easily with alcohols to give esters. Crystalline dimethyl oxalate is, for example, produced by the reaction of oxahc acid dihydrate and methanol under reflux for a few hours. When oxahc acid is treated with phosphoms pentachloride, oxalyl chloride, ClCOCOCl, is formed (6). 

Acids react with alkyl hydroperoxides in two different ways, depending on the hydroperoxide stmcture and the acid strength (45). 

This reaction is commercially important because it serves as a basis for the manufacture of polycarbonate. Carboxyhc acids react with phosgene to give acid chlorides (26) (see Carboxylic acids). 

Phosphoric acid, aside from its acidic behavior, is relatively unreactive at room temperature. It is sometimes substituted for sulfuric acid because of its lack of oxidising properties (see SuLFURic ACID AND SULFURTRIOXIDe). The reduction of phosphoric acid by strong reducing agents, eg, H2 or C, does not occur to any measurable degree below 350—400°C. At higher temperatures, the acid reacts with most metals and their oxides. Phosphoric acid is stronger than acetic, oxaUc, siUcic, and boric acids, but weaker than sulfuric, nitric, hydrochloric, and chromic acids. 

Phosphonic acid is an intermediate in the production of alkylphosphonates that are used as herbicides and as water treatment chemicals for sequestration, scale inhibition, deflocculation, and ion-control agents in oil weUs, cooling tower waters, and boiler feed waters. For example, aqueous phosphonic acid reacts with formaldehyde and ammonium chloride in the presence of hydrochloric acid to yield aminotri(methylenephosphonic acid) [6419-19-8]. 

The carboxylic acids react with ammonia and with primary amines in a similar manner ... 

The by-product of this process, pelargonic acid [112-05-0] is also an item of commerce. The usual source of sebacic acid [111-20-6] for nylon-6,10 [9008-66-6] is also from a natural product, ticinoleic acid [141-22-0] (12-hydroxyoleic acid), isolated from castor oil [8001-79-4]. The acid reacts with excess sodium or potassium hydroxide at high temperatures (250—275°C) to produce sebacic acid and 2-octanol [123-96-6] (166) by cleavage at the 9,10-unsaturated position. The manufacture of dodecanedioic acid [693-23-2] for nylon-6,12 begins with the catalytic trimerization of butadiene to make cyclododecatriene [4904-61-4] followed by reduction to cyclododecane [294-62-2] (see Butadiene). The cyclododecane is oxidatively cleaved to dodecanedioic acid in a process similar to that used in adipic acid production. 

Reactions. Thiosahcyhc acids reacts with ethyhnercuric chloride in alcohol and in the presence of sodium hydroxide to yield sodium ethyhnercurithiosahcylate [54-64-8] (thimerosal Merthiolate, Eh Lilly and Company) (63) (eq. 12). 

Oxidation. Succinic acid reacts with hydrogen peroxide, giving different products that depend on the experimental conditions peroxysuccinic acid [2279-96-1] (CH2COOOH)2, oxosuccinic acid [328-42-7] (oxaloacetic acid) malonic acid [141-82-2] or a mixture of acetaldehyde, malonic acid, and make acid [6915-15-7]. Succinic anhydride in dimethylformamide (DMF) with H2O2 gives monoperoxysuccinic acid [3504-13-0], HOOCCH2CH2COOOH, mp 107°C (70). 

Succinic acid reacts with urea in aqeous solution to give a 2 1 compound having mp 141°C (116,117), which has low solubiUty in water. A method for the recovery of succinic acid from the wastes from adipic acid manufacture is based on this reaction (118,119). The monoamide succinamic acid [638-32-4] NH2COCH2CH2COOH, is obtained from ammonia and the anhydride or by partial hydrolysis of succinknide. The diamide succinamide [110-14-3], (CH2C0NH2)2, nip 268—270°C, is obtained from succinyl chloride and ammonia or by partial hydrolysis of succinonitrile. Heating succinknide with a primary amine gives A/-alkylsucckiknides (eq. 9). 

Chlorine Vehicle ndStabilizer. Sulfamic acid reacts with hypochlorous acid to produce /V-ch1orosu1famic acids, compounds in which the chlorine is stiU active but more stable than in hypochlorite form. The commercial interest in this area is for chlorinated water systems in paper mills, ie, for slimicides, cooling towers, and similar appHcations (54) (see INDUSTRIALANTIMICROBIALAGENTS). 

Sulfonic acids may be subjected to a variety of transformation conditions, as shown in Figure 2. Sulfonic acids can be used to produce sulfonic anhydrides by treatment with a dehydrating agent, such as thionyl chloride [7719-09-7J. This transformation is also accomphshed using phosphoms pentoxide [1314-56-3J. Sulfonic anhydrides, particulady aromatic sulfonic anhydrides, are often produced in situ during sulfonation with sulfur trioxide. Under dehydrating conditions, sulfonic acids react with substituted aromatic compounds to give sulfone derivatives. 

Compounds, eg, phenacyl hahdes, ben2yl hahdes, alkyl iodides, or alkyl esters of sulfonic acids, react with DMSO at 100—120°C to give aldehydes (qv) and ketones (qv) in 50—85% yields (eq. 8) (41) ... 

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