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      1-Hexanol (IUPAC name hexan-1-ol) is an organic alcohol with a six-carbon chain and a condensed structural formula of CH3(CH2)5OH. This colorless liquid is slightly soluble in water, but miscible with diethyl ether and ethanol. Two additional straight chain isomers of 1-hexanol, 2-hexanol and 3-hexanol, exist, both of which differing by the location of the hydroxyl group. Many isomeric alcohols have the formula C6H13OH. It is used in the perfume industry.


      Preparation


      Hexanol is produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products. An idealized synthesis is shown:

      Al(C2H5)3 + 6C2H4 → Al(C6H13)3
      Al(C6H13)3 + 1+1⁄2O2 + 3H2O → 3HOC6H13 + Al(OH)3
      The process generates a range of oligomers that are separated by distillation.


      = Alternative methods

      =
      Another method of preparation entails hydroformylation of 1-pentene followed by hydrogenation of the resulting aldehydes. This method is practiced in industry to produce mixtures of isomeric C6-alcohols, which are precursors to plasticizers.
      In principle, 1-hexene could be converted to 1-hexanol by hydroboration (diborane in tetrahydrofuran followed by treatment with hydrogen peroxide and sodium hydroxide):

      This method is instructive and useful in laboratory synthesis but of no practical relevance because of the commercial availability of inexpensive 1-hexanol from ethylene.


      Occurrence in nature


      1-Hexanol is believed to be a component of the odour of freshly mown grass. Alarm pheromones emitted by the Koschevnikov gland of honey bees contain 1-hexanol. It also is partly responsible for the fragrance of strawberries.


      See also


      Cis-3-Hexenal, another volatile organic compound, is also considered responsible for the freshly mowed grass odor.


      References




      External links


      International Chemical Safety Card 1084

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    1-Hexanol - Wikipedia

    1-Hexanol (IUPAC name hexan-1-ol) is an organic alcohol with a six-carbon chain and a condensed structural formula of CH 3 (CH 2) 5 OH. This colorless liquid is slightly soluble in water, but miscible with diethyl ether and ethanol.

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    1-Hexanol anhydrous, = 99 111-27-3 - MilliporeSigma

    1-Hexanol is a linear primary alcohol. It is formed as an intermediate during the catalytic transformation of cellulose. The ability of 1,1,3,3-tetramethylguanidine (TMG) in 1-hexanol solvent system to capture carbon dioxide has been assessed. The solubility of light fullerenes in 1-hexanol as a function of temperature and pressure was studied.

    1-Hexanol | 111-27-3 - ChemicalBook

    1-Hexanol (CAS 111-27-3) information, including chemical properties, structure, melting point, boiling point, density, formula, molecular weight, uses, prices, suppliers, SDS and more, available at Chemicalbook.

    1-Hexanol - Hexyl alcohol - MilliporeSigma

    1-Hexanol. CH3(CH2)5OH. Synonyms: Hexyl alcohol. CAS 111-27-3. Molecular Weight 102.17. Browse 1-Hexanol and related products at MilliporeSigma.

    hexanol | C6H14O - ChemSpider

    ChemSpider record containing structure, synonyms, properties, vendors and database links for hexanol, 111-27-3, 1-Hexanol, ZSIAUFGUXNUGDI-UHFFFAOYSA-N