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Acetic anhydride in a glass bottle. Acetic anhydride, like most acid anhydrides, is a flexible molecule with a nonplanar structure. [4] The pi system linkage through the central oxygen offers very weak resonance stabilization compared to the dipole-dipole repulsion between the two carbonyl oxygens. The energy barriers to bond rotation between ...
In the laboratory, it can be easily synthesized from anthranilic acid and acetic anhydride. N-Acetylanthranilic acid exhibits triboluminescence when crushed. [5] The fractured crystals have large electrical potentials between areas of high and low charge.
Methyl acetate is produced industrially via the carbonylation of methanol as a byproduct of the production of acetic acid. [6] Methyl acetate also arises by esterification of acetic acid with methanol in the presence of strong acids such as sulfuric acid; this production process is famous [according to whom?] because of Eastman Kodak's intensified process using a reactive distillation.
sec-Butyl acetate, or s-butyl acetate, is an ester commonly used as a solvent in lacquers and enamels, where it is used in the production of acyclic polymers, vinyl resins, and nitrocellulose. [3]
Triacetin was prepared in the 19th century from glycerol and acetic acid. [13] Its synthesis from acetic anhydride and glycerol is simple and inexpensive. 3 (CH 3 CO) 2 O + 1 C 3 H 5 (OH) 3 → 1 C 3 H 5 (OCOCH 3) 3 + 3 CH 3 CO 2 H. This synthesis has been conducted with catalytic sodium hydroxide and microwave irradiation to give a 99% yield ...
Thioglycolic acid with a pK a of 3.83 [7] is an acid about 8.5 times stronger than acetic acid (pK a 4.76): HSCH 2 CO 2 H → HSCH 2 CO 2 − + H + The second ionization has a pK a of 9.3: HSCH 2 CO 2 − → − SCH 2 CO 2 − + H + Thioglycolic acid is a reducing agent, especially at higher pH.
It hydrolyzes in moist air to acetic acid and nitric acid. Alternatively, nitric acid adds to ketene. [2] For aromatic nitrations, acetyl nitrate is generated in situ by mixing nitric acid with an excess of acetic anhydride in the presence of the aromatic substrate. [3] It acetylates amines, akin to the behavior of acetyl chloride:
Triacetate is derived from cellulose by acetylating cellulose with acetic acid and/or acetic anhydride. Acetylation converts hydroxyl groups in cellulose to acetyl groups, which renders the cellulose polymer much more soluble in organic solvents. The cellulose acetate is dissolved in a mixture of dichloromethane and methanol for spinning.