2-Nitro-l,3-propanediol

On dehydration, nitro alcohols yield nitro-olefins. The ester of the nitro alcohol is treated with caustic or is refluxed with a reagent, eg, phthaUc anhydride or phosphoms pentoxide. A mil der method involves the use of methane sulfonyl chloride to transform the hydroxyl into a better leaving group. Yields up to 80% after a reaction time of 15 min at 0°C have been reported (5). In aqueous solution, nitro alcohols decompose at pH 7.0 with the formation of formaldehyde. One mole of formaldehyde is released per mole of monohydric nitro alcohol, and two moles of formaldehyde are released by the nitrodiols. However, 2-hydroxymethyl-2-nitro-l,3-propanediol gives only two moles of formaldehyde instead of the expected three moles. The rate of release of formaldehyde increases with the pH or the temperature or both. 

In a battery of tests, which determine the tendency of chemicals to inhibit aquatic organisms, accumulate in such organisms, and degrade in the environment, 2-hydroxy-2-nitro-l,3-propanediol was found to have low potential for harm in the environment (7). 

Polymers. AH nitro alcohols are sources of formaldehyde for cross-linking in polymers of urea, melamine, phenols, resorcinol, etc (see Amino RESINS AND PLASTICS). Nitrodiols and 2-hydroxymethyl-2-nitro-l,3-propanediol can be used as polyols to form polyester or polyurethane products (see Polyesters Urethane polymers). 2-Methyl-2-nitro-l-propanol is used in tires to promote the adhesion of mbber to tire cord (qv). Nitro alcohols are used as hardening agents in photographic processes, and 2-hydroxymethyl-2-nitro-l,3-propanediol is a cross-linking agent for starch adhesives, polyamides, urea resins, or wool, and in tanning operations (17—25). Wrinkle-resistant fabric with reduced free formaldehyde content is obtained by treatment with... 

Stabilizers. Nitro alcohols can be used to prevent the decomposition of phenylenediarnine color-developing agents (27). 2-Hydroxymethyl-2-nitro-l,3-propanediol and 2-nitro-1-butanol have been used as additives for the stabilization of 1,1,1-trichloroethane. 

Other. 2-Nitro-1-butanol is an excellent solvent for many polyamide resins, cellulose acetate butyrate, and ethylceUulose. It can be utilized in paint removers for epoxy-based coatings. 2-Hydroxymethyl-2-nitro-l,3-propanediol is usebil for control of odors in chemical toilets. Its slow release of formaldehyde ensures prolonged action to control odor, and there is no reodorant problem which sometimes is associated with the use of free formaldehyde. 2-Hydroxymethyl-2-nitro-l,3-propanediol solutions are effective preservative and embalming fluids. The slow Uberation of formaldehyde permits thorough penetration of the tissues before hardening. 

Nitromethane. The nitroparaffins are used widely as raw materials for synthesis. Nitromethane is used to produce the nitro alcohol (qv) 2-(hydroxymethyl)-2-nitro-l,3-propanediol, which is a registered biocide useful for control of bacteria in a number of industrial processes. This nitro alcohol also serves as the raw material for the production of the alkanolamine (qv) 2-amino-2-(hydroxymethyl)-l,3-propanediol, which is an important buffering agent useful in a number of pharmaceutical appHcations. 

Methyl-2-nitro-l,3-propanediol [77-49-6] M 135.1, m 145 . Crystd from n-butanol. 

Tris-(hydroxymethyl)nitromethane [2-(hydroxymethyl)-2-nitro-l,3-propanediol] [126-11-4] M 151.1, m 174-175°(dec, tech grade), 214°(pure). Crystd from CHCl3/ethyl acetate or ethyl acetate/ benzene. It is an acid and a O.IM sol in H2O has pH 4.5. IRRITANT. 

Replacement of one tosyloxy group m 2-fluoro-2-nitro-l,3-propanediol ditosylate by azide ion occurs easily [S5] (equation 75)... 

Ethyl-2-nitro-l, 3-propanediol dinitrate see 1, l-Di(methylol)-l -nitropropane dinitrate 5 D1359... 

Nitroethane and formaldehyde are first reacted to give 2-methyl-2-nitro-l,3-propanediol. This is reacted with 2-ethylhexylamine and formaldehyde to give 5-nitro-l,3-bis(2-ethylhexyl)-5-methyl-hexahydropyrimidine. 

Scheme 9.2 Formation of 2-amino-1-butanol in the hydrogenation of 2-ethyl-2-nitro-l,3-propanediol over Raney Ni.

By March 1, 1957, the aminoethylation of the following materials and compds had been achieved by the Wyandotte Chemicals Corp cellulose, cellulose derivatives, regenerated cellulose, 2-hydroxymethyl-2-nitro-l,3-propanediol, nylon, polyurethane, polyvinyl alcohol, polyvinylchloride, protein(wool), starch and toluene diisocyanate... 

Bromo-2-nitro-l,3-propanediol p-bromo-p-nitrotrimethyl-eneglycol Myacide. 

Tris-(hydroxymethyl)nitromethane [2-(hydroxymethyl)-2-nitro-l,3-propanediol] [126-11-4]... 

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