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  2. Beckmann rearrangement - Wikipedia

    en.wikipedia.org/wiki/Beckmann_rearrangement

    The Beckmann Rearrangement. The archetypal Beckmann rearrangement [4] is the conversion of cyclohexanone to caprolactam via the oxime. Caprolactam is the feedstock in the production of Nylon 6. [5] The Beckmann solution consists of acetic acid, hydrochloric acid and acetic anhydride, and was widely used to

  3. Cyclohexanone oxime - Wikipedia

    en.wikipedia.org/wiki/Cyclohexanone_oxime

    The most famous and commercially important reaction of cyclohexanone oxime is Beckmann rearrangement yielding ε-caprolactam, which is used to produce Nylon 6: This reaction is catalyzed by sulfuric acid, [1] but industrial scale reactions use solid acids. [2] Typical of oximes, the compound can be reduced by sodium amalgam to produce ...

  4. Caprolactam - Wikipedia

    en.wikipedia.org/wiki/Caprolactam

    It was estimated that 90% of all caprolactam is synthesised from cyclohexanone (1), which is first converted to its oxime (2). Treatment of this oxime with acid induces the Beckmann rearrangement to give caprolactam (3): [2] The immediate product of the acid-induced rearrangement is the bisulfate salt of caprolactam.

  5. Oxime - Wikipedia

    en.wikipedia.org/wiki/Oxime

    About half of the world's supply of cyclohexanone, more than a million tonnes annually, is converted to the oxime. In the presence of sulfuric acid catalyst , the oxime undergoes the Beckmann rearrangement to give the cyclic amide caprolactam: [ 18 ]

  6. Hydroxylamine - Wikipedia

    en.wikipedia.org/wiki/Hydroxylamine

    Conversion of cyclohexanone to caprolactam involving the Beckmann rearrangement. Approximately 95% of hydroxylamine is used in the synthesis of cyclohexanone oxime, a precursor to Nylon 6. [10] The treatment of this oxime with acid induces the Beckmann rearrangement to give caprolactam (3). [21]

  7. N-Hydroxyphthalimide - Wikipedia

    en.wikipedia.org/wiki/N-Hydroxyphthalimide

    The use of N-hydroxyphthalimide as a catalyst in the oxidation of KA oil avoids the formation of the undesirable by-product ammonium sulfate which is produced by the conventional ε-caprolactam synthesis (Beckmann rearrangement of cyclohexanone oxime with sulfuric acid). Alkanes are converted into nitroalkanes in the presence of nitrogen ...

  8. Ring expansion and contraction - Wikipedia

    en.wikipedia.org/wiki/Ring_expansion_and_contraction

    Examples include high impact applications of the Beckmann rearrangement (for introduction of nitrogen into codeine) [14] and the Baeyer-Villiger oxidation (introduction of oxygen to cage-annulated ethers) [15] in synthesis. Both occur with the expulsion of a leaving group as the alkyl group migrates onto the exocyclic heteroatom, which is ...

  9. Barton reaction - Wikipedia

    en.wikipedia.org/wiki/Barton_reaction

    After a short synthesis to obtain the desired spiro-[5.4] system, Nobel laureaute E.J. Corey and co-workers employed a Barton reaction to selectively introduce an oxime in a 1,3-diaxial position to the nitrite ester. The oxime is converted to a lactam via a Beckmann rearrangement and then reduced to the natural product. [24]