Tiglic acid

Tiglic acid

2-Butenoic acid,2-methyl-,(2E)-;Crotonic acid,2-methyl-,(E)-;Tiglic acid;2-Butenoic acid,2-methyl-,(E)-;(2E)-2-Methyl-2-butenoic acid;Cevadic acid;trans-α,β-Dimethylacrylic acid;trans-2,3-Dimethylacrylic acid;trans-2-Methyl-2-butenoic acid;trans-2-Methylcrotonic acid;(E)-2-Methylcrotonic acid;Tiglinic acid;(E)-2,3-Dimethylacrylic acid;(E)-α-Methylcrotonic acid;(E)-2-Methyl-2-butenoic acid;NSC 44235;NSC 8999

80-59-1

C5H8O2

InChIKey=UIERETOOQGIECD-ONEGZZNKSA-N

100.12

100.12

1236500

201-295-0

I5792N03HC

44235|8999

3261

Triclinic plates, rods from water|Thick, syrupy liquid or colorless crystals|Tablets

29161980

Perfuming

37.3

1

White to beige Crystalline Powder and Chunks

0.9427 g/cm³ @ Temp: 99.5 °C

64.5 °C

198.5 °C

101°C

1.451

soluble in hot water

Refrigerator (+4°C)

1.33X10-1 mm Hg at 25 deg C

This material is capable of creating a dust explosion.

Spicey

Henry's Law constant = 7.1X10-7 atm-cu m/mole at 25 °C (est)

pKa = 4.96 at 18 °C|pk = 5.02 at 25 °C

Volatile with steam|Combustible|Liquid; density: 0.9498 at 20 °C/4 °C; boiling point: 139.6 °C at 766 mm Hg; index of refraction: 1.4370 at 20 °C/D. /Methyl ester/|Liquid; density: 0.9247 at 20 °C/4 °C; boiling point: 156 °C at 752 mm Hg, 55.5 °C at 11 mm Hg; index of refraction: 1.4350 at 20 °C/D; heat of formation: 953.2 kilocalories at constant volume, 954.4 kilocalories at constant pressure. /Ethyl ester/|Liquid; pleasant odor; density: 0.9279 at 15 °C/15 °C; boiling point: 149-151 °C at 7 mm Hg. /Geranyl ester/|Leaflets; much less soluble in water than calcium angelate: 100 parts of aqueous solution saturated at 17 °C contains 6.05 parts of anhydrous calcium tiglate. /Calcium salt trihydrate/|Hydroxyl radical reaction rate constant = 3.1X10-11 cu cm/molecule-sec at 25 °C (est)

Slightly soluble in water.

Acids, Carboxylic

TIGLIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Molar heat of combusion: 635.1 kilocalories

Critical temperature: 680.62 K; critical pressure: 4857.97 kPa (est)