1-Propanol: Difference between revisions
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1-Propanol shows the normal reactions of a [[primary alcohol]]. Thus it can be converted to [[Haloalkane|alkyl halides]]; for example red [[phosphorus]] and [[iodine]] produce [[1-iodopropane]] in 90% yield, while [[phosphorus trichloride|PCl<sub>3</sub>]] with catalytic [[Zinc chloride|ZnCl<sub>2</sub>]] gives [[1-chloropropane]]. Reaction with [[acetic acid]] in the presence of an [[sulfuric acid|H<sub>2</sub>SO<sub>4</sub>]] catalyst under [[Fischer esterification]] conditions gives propyl acetate, while refluxing propanol overnight with formic acid alone can produce propyl formate in 65% yield. Oxidation of 1-propanol with [[Sodium dichromate|Na<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub>]] and H<sub>2</sub>SO<sub>4</sub> gives only a 36% yield of [[propionaldehyde]], and therefore for this type of reaction higher yielding methods using [[Pyridinium chlorochromate|PCC]] or the [[Swern oxidation]] are recommended. Oxidation with [[chromic acid]] yields [[propionic acid]] |
1-Propanol shows the normal reactions of a [[primary alcohol]]. Thus it can be converted to [[Haloalkane|alkyl halides]]; for example red [[phosphorus]] and [[iodine]] produce [[1-iodopropane]] in 90% yield, while [[phosphorus trichloride|PCl<sub>3</sub>]] with catalytic [[Zinc chloride|ZnCl<sub>2</sub>]] gives [[1-chloropropane]]. Reaction with [[acetic acid]] in the presence of an [[sulfuric acid|H<sub>2</sub>SO<sub>4</sub>]] catalyst under [[Fischer esterification]] conditions gives propyl acetate, while refluxing propanol overnight with formic acid alone can produce propyl formate in 65% yield. Oxidation of 1-propanol with [[Sodium dichromate|Na<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub>]] and H<sub>2</sub>SO<sub>4</sub> gives only a 36% yield of [[propionaldehyde]], and therefore for this type of reaction higher yielding methods using [[Pyridinium chlorochromate|PCC]] or the [[Swern oxidation]] are recommended. Oxidation with [[chromic acid]] yields [[propionic acid]] |
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[[Image:Propanol |
[[Image:Propanol-reactions-2D-skeletal.png|450px|left|Some example reactions of 1-propanol]] |
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Revision as of 18:09, 18 April 2008
Propan-1-ol is a primary alcohol with the formula CH3CH2CH2OH. It is also known as 1-propanol, 1-propyl alcohol, n-propyl alcohol, or simply propanol. It is an isomer of propan-2-ol. It is used as a solvent in the pharmaceutical industry, and for resins and cellulose esters. It is formed naturally in small amounts during many fermentation processes.
Chemical properties
1-Propanol shows the normal reactions of a primary alcohol. Thus it can be converted to alkyl halides; for example red phosphorus and iodine produce 1-iodopropane in 90% yield, while PCl3 with catalytic ZnCl2 gives 1-chloropropane. Reaction with acetic acid in the presence of an H2SO4 catalyst under Fischer esterification conditions gives propyl acetate, while refluxing propanol overnight with formic acid alone can produce propyl formate in 65% yield. Oxidation of 1-propanol with Na2Cr2O7 and H2SO4 gives only a 36% yield of propionaldehyde, and therefore for this type of reaction higher yielding methods using PCC or the Swern oxidation are recommended. Oxidation with chromic acid yields propionic acid
Preparation
1-Propanol is a major constituent of fusel oil, a by-product formed from certain amino acids when potatoes or grains are fermented to produce ethanol. This is no longer a significant source of the material.
1-Propanol is manufactured by catalytic hydrogenation of propionaldehyde. The propionaldehyde is itself produced via the oxo process, by hydroformylation of ethylene using carbon monoxide and hydrogen in the presence of a catalyst such as cobalt octacarbonyl or a rhodium complex.
- (1) H2C=CH2 + CO + H2 → CH3CH2CH=O
- (2) CH3CH2CH=O + H2 → CH3CH2CH2OH
A traditional laboratory preparation of 1-propanol involves treating 1-iodopropane with moist Ag2O.
History
1-Propanol was discovered in 1853 by Chancel, who obtained it by fractional distillation of fusel oil.
References
 | This article has an unclear citation style. (September 2007) |
- Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. (1989), Vogel's Textbook of Practical Organic Chemistry (5th ed.), Harlow: Longman, ISBN 0-582-46236-3
- Handbook of Chemistry and Physics, 71st edition, CRC Press, Ann Arbor, Michigan, 1990.
- The Merck Index, 7th edition, Merck & Co, Rahway, New Jersey, USA, 1960.
- Perkin, W. H.; Kipping, F. S. (1922). Organic Chemistry, London: W. & R. Chambers.
