DL-Tartaric Acid

Title: DL-Tartaric Acid
CAS Registry Number: 133-37-9
CAS Name: 2,3-Dihydroxybutanedioic acid
Additional Names: racemic tartaric acid; racemic acid; dl-tartaric acid; resolvable tartaric acid; uvic acid; paratartaric acid; dl-Weinsäure (German); Vogesensäure (German); Traubensäure (German)
Molecular Formula: C4H6O6
Molecular Weight: 150.09
Percent Composition: C 32.01%, H 4.03%, O 63.96%
Literature References: Probably never a natural product, although sometimes found in small amounts during wine-making. Prepn from L-tartaric acid by boiling with aq NaOH (meso-tartaric acid is obtained as a byproduct): Holleman, Org. Synth. 6, 82 (1926); coll. vol. I (2nd ed., 1941) p 497. Synthesis by oxidation of fumaric acid: Milas, Terry, J. Am. Chem. Soc. 47, 1412 (1925); Milas, Sussman, ibid. 58, 1302 (1936); US 2000213 (1935 to Standard Brands). From maleic acid: Church, Blumberg, Ind. Eng. Chem. 43, 1780 (1951).
Properties: Anhydr acid, triclinic pinacoidal crystals from abs alc, from water above 73°, or by drying the monohydrate at 100°. mp 206°. pKa1 2.96; pKa2 4.24. Less soluble in water than L-tartaric acid. pH of 0.1M aq soln: 2.0. Soly in alcohol (g/100 g): 2.006 at 0°; 3.153 at 15°; 5.01 at 25°; 6.299 at 40°. Soly in ether about 1%.
Melting point: mp 206°
pKa: pKa1 2.96; pKa2 4.24
Derivative Type: Monohydrate
Properties: Triclinic pinacoidal crystals from water. d420 1.697. One hundred parts (w/w) of water dissolve 14.00 parts at 10°; 20.60 at 20°; 29.10 at 30°; 43.32 at 40°; 99.88 at 70°; 184.91 at 100°.
Density: d420 1.697
D-Lyxose DMAN D-Mannitol Hexanitrate D-manno-Heptulose D-Mannose