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Names | |
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Preferred IUPAC name
Octan-1-ol | |
Other names
1-Octanol; n-Octanol; Capryl alcohol; Octyl alcohol
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Identifiers | |
3D model (JSmol)
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1697461 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.561 |
EC Number |
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82528 | |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C8H18O | |
Molar mass | 130.231 g·mol−1 |
Appearance | Colorless liquid[1] |
Odor | Aromatic[1] |
Density | 0.83 g/cm3 (20 °C)[1] |
Melting point | −16 °C (3 °F; 257 K)[1] |
Boiling point | 195 °C (383 °F; 468 K)[1] |
0.3 g/L (20 °C)[1] | |
Viscosity | 7.36 cP[2] |
Hazards | |
GHS labelling: | |
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Warning | |
H319 | |
P264, P280, P305+P351+P338, P337+P313 | |
NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1-Octanol, also known as octan-1-ol, is the organic compound with the molecular formula CH3(CH2)7OH. It is a fatty alcohol. Many other isomers are also known generically as octanols. 1-Octanol is manufactured for the synthesis of esters for use in perfumes and flavorings. It has a pungent odor. Esters of octanol, such as octyl acetate, occur as components of essential oils.[3] It is used to evaluate the lipophilicity of pharmaceutical products.
YouTube Encyclopedic
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1/5Views:23 3441 94079 9713 5251 981
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Nomenclatura de ALCOHOLES (paso a paso)
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Hydroboration/Oxidation of 1-Octene Experiment, Part 1: Prelab Lecture
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Oxidation of Alcohols: Primary, Secondary and Tertiary
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Hydroboration/Oxidation of 1-Octene Experiment, Part 2: Carrying out the Hydroboration Reaction
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Hydroboration/Oxidation of 1-Octene Experiment, Part 4: Carrying out the Oxidation Reaction and GC
Transcription
Preparation
Octanol is mainly produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products. This route is known as the Ziegler alcohol synthesis.[3] An idealized synthesis is shown:
- Al(C2H5)3 + 9 C2H4 → Al(C8H17)3
- Al(C8H17)3 + 3 O + 3 H2O → 3 HOC8H17 + Al(OH)3
The process generates a range of alcohols, which can be separated by distillation.
The Kuraray process defines an alternative route to 1-octanol, but using C4 + C4 building strategy. 1,3-Butadiene is dimerized concomitant with the addition of one molecule of water. This conversion is catalyzed by palladium complexes. The resulting doubly unsaturated alcohol is then hydrogenated.[4]
Water/octanol partitioning
Octanol and water are immiscible. The distribution of a compound between water and octanol is used to calculate the partition coefficient, P, of that molecule (often expressed as its logarithm to the base 10, log P). Water/octanol partitioning is a relatively good approximation of the partitioning between the cytosol and lipid membranes of living systems.[5]
Many dermal absorption models consider the stratum corneum/ water partition coefficient to be well approximated by a function of the water/octanol partition coefficient of the form:[6]
Where a and b are constants, is the stratum corneum/water partition coefficient, and is the water/octanol partition coefficient. The values of a and b vary between papers, but Cleek & Bunge[7] have reported the values a = 0, b = 0.74.
Properties and uses
With a flash point of 81 °C, 1-octanol is not seriously flammable, though its autoignition temperature is as low as 245 °C. 1-Octanol is mainly consumed as a precursor to perfumes.[3] It has been examined for controlling essential tremor and other types of involuntary neurological tremors because evidence indicates it can relieve tremor symptoms at lower doses than are required to obtain a similar level of symptomatic relief from consumption of ethanol, thereby reducing the risk alcohol intoxication at therapeutic dosages.[8]
1-Octanol hydrogen bonds to Lewis bases. It is a Lewis acid in the ECW model and its acid parameters are EA = 0.85 and C A = 0.87.[9]
See also
References
- ^ a b c d e f Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ Bhattacharjee, A.; Roy, M. N. (2010-11-17). "Density, Viscosity, and Speed of Sound of (1-Octanol + 2-Methoxyethanol),(1-Octanol + N,N-Dimethylacetamide), and (1-Octanol + Acetophenone) at Temperatures of (298.15, 308.15, and 318.15) K". Journal of Chemical & Engineering Data. 55 (12): 5914–5920. doi:10.1021/je100170v.
- ^ a b c Falbe, Jürgen; Bahrmann, Helmut; Lipps, Wolfgang; Mayer, Dieter; Frey, Guido D. (2013). "Alcohols, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. American Cancer Society. doi:10.1002/14356007.a01_279.pub2. ISBN 978-3527306732.
- ^ J. Grub; E. Löser (2012). "Butadiene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_431.pub2. ISBN 978-3527306732.
- ^ Schwarzenbach, Rene P.; Gschwend, Philip M.; Imboden, Dieter M. (2003). <i>Environmental organic chemistry</i>. John Wiley. ISBN 0-471-35053-2.
- ^ McCarley KD, Bunge AL (2001). "Pharmacokinetic Models of Dermal Absorption". Journal of Pharmaceutical Sciences. 90 (11): 1699–1719. doi:10.1002/jps.1120. PMID 11745728.
- ^ Cleek RL, Bunge AL (1993). "A new method for estimating dermal absorption from chemical exposure. 1. General approach". Pharmaceutical Research. 10 (4): 497–506. doi:10.1023/A:1018981515480. PMID 8483831. S2CID 24534572.
- ^ Bushara K.; et al. (2004). "Pilot trial of 1-octanol in essential tremor". Neurology. 62 (1): 122–124. doi:10.1212/01.wnl.0000101722.95137.19. PMID 14718713. S2CID 9015641.
- ^ Vogel, Glenn C.; Drago, Russell S. (1996). "The ECW Model". Journal of Chemical Education. 73 (8): 701. Bibcode:1996JChEd..73..701V. doi:10.1021/ed073p701. ISSN 0021-9584.
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