Hydrocyanation - Usage

Usage

Hydrocyanation is important due to the versatility of alkyl nitriles (RCN), which are important intermediates for the syntheses of amides, amines, carboxylic acids, and ester compounds. The most popular industrial usage of nickel-catalyzed hydrocyanation is for adiponitrile (NC–(CH2)4–CN) synthesis from 1,3–butadiene (CH2=CH–CH=CH2). Adiponitrile is a precursor to hexamethylenediamine (H2N–(CH2)6–NH2), which is used for the production of certain kinds of Nylon. The DuPont ADN process to give adiponitrile is shown below:

This process consists of three steps: hydrocyanation of butadiene to a mixture of 2-methyl-3-butenenitrile (2M3BM) and 3-pentenenitrile (3PN), an isomerization step from 2M3BM (not desired) to 3PN and a second hydrocyanation (aided by a Lewis acid cocatalyst such as aluminium trichloride or triphenylboron) to adiponitrile.

Naproxen, an anti-inflammatory drug, utilizes an asymmetric enantioselective hydrocyanation of vinylnaphthalene from a phosphinite(OPR2) ligand, L .The enantioselectivity of this reaction is important because only the S enantiomer is medicinally desirable, whereas the R enantiomer produces harmful health effects. This reaction can produce the S enantiomer with > 90% selectivity. Upon recrystallization of the crude product, the optically pure nitrile can be attained.

Read more about this topic:  Hydrocyanation

Other articles related to "usage":

Usage - History
... According to Jeremy Butterfield, "The first person we know of who made usage refer to language was Daniel Defoe, at the end of the seventeenth century" ...
Gong - Other Uses
... In older Javanese usage and in modern Balinese usage, gong is used to identify an ensemble of instruments ... In contemporary central Javanese usage, the term gamelan is preferred and the term gong is reserved for the gong ageng, the largest instrument of the type, or for surrogate instruments such as the gong ... In Balinese usage, gong refers to Gamelan Gong Kebyar ...
Hyphen - Usage in English
... For Wikipedia's own standards for hyphen usage, see WikipediaManual of Style#Hyphens Hyphens are mostly used to break single words into parts, or to join ... manuals of style prescribe different usage guidelines ...
Nancy Mitford - Biography - U and Non-U
... to popularise the "U", or upper-class, and "non-U" classification of linguistic usage and behaviour (see U and non-U English) — although this is something she saw as a tease and she certainly ... portrayed her as the snobbish inventor and main preserver of this usage ... Ross, the actual inventor of the phrase, as an example of upper-class linguistic usage ...

Famous quotes containing the word usage:

    ...Often the accurate answer to a usage question begins, “It depends.” And what it depends on most often is where you are, who you are, who your listeners or readers are, and what your purpose in speaking or writing is.
    Kenneth G. Wilson (b. 1923)

    Girls who put out are tramps. Girls who don’t are ladies. This is, however, a rather archaic usage of the word. Should one of you boys happen upon a girl who doesn’t put out, do not jump to the conclusion that you have found a lady. What you have probably found is a lesbian.
    Fran Lebowitz (b. 1951)

    Pythagoras, Locke, Socrates—but pages
    Might be filled up, as vainly as before,
    With the sad usage of all sorts of sages,
    Who in his life-time, each was deemed a bore!
    The loftiest minds outrun their tardy ages.
    George Gordon Noel Byron (1788–1824)