tert-Amyl alcohol
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
2-Methylbutan-2-ol | |||
| Other names
2-Methyl-2-butanol tert-Amyl alcohol t-Amylol TAA tert-Pentyl alcohol 2-Methyl-2-butyl alcohol t-Pentylol Amylene hydrate Dimethylethylcarbinol | |||
| Identifiers | |||
75-85-4  | |||
| 3D model (Jmol) | Interactive image | ||
| 1361351 | |||
| ChEBI | CHEBI:132750 | ||
| ChEMBL | ChEMBL44658 | ||
| ChemSpider | 6165 | ||
| ECHA InfoCard | 100.000.827 | ||
| EC Number | 200-908-9 | ||
| KEGG | D02931 | ||
| MeSH | tert-amyl+alcohol | ||
| PubChem | 6405 | ||
| RTECS number | SC0175000 | ||
| UNII | 69C393R11Z | ||
| UN number | 1105 | ||
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| Properties | |||
| C5H12O | |||
| Molar mass | 88.15 g·mol−1 | ||
| Appearance | Colorless liquid | ||
| Odor | Camphorous | ||
| Density | 0.805 g/cm−3 [1] | ||
| Melting point | −9 °C; 16 °F; 264 K | ||
| Boiling point | 101 to 103 °C; 214 to 217 °F; 374 to 376 K | ||
| 120 g·dm−3 | |||
| log P | 1.095 | ||
| Vapor pressure | 1.6 kPa (at 20 °C) | ||
| Refractive index (nD) |
1.405 | ||
| Viscosity | 4.4740 mPa·s (at 298.15 K)[1] | ||
| Thermochemistry | |||
| Std molar entropy (S |
229.3 J K−1 mol−1 | ||
| Std enthalpy of formation (ΔfH |
−380.0–−379.0 kJ mol−1 | ||
| Std enthalpy of combustion (ΔcH |
−3.3036–−3.3026 MJ mol−1 | ||
| Hazards | |||
| Safety data sheet | hazard.com | ||
| GHS pictograms |   | ||
| GHS signal word | DANGER | ||
| H225, H315, H332, H335 | |||
| P210, P261 | |||
| EU classification (DSD) |
 F  Xn | ||
| R-phrases | R11, R20, R37/38 | ||
| S-phrases | (S2), S46 | ||
| NFPA 704 | |||
| Flash point | 19 °C (66 °F; 292 K) | ||
| 437 °C (819 °F; 710 K) | |||
| Explosive limits | 9% | ||
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
 verify (what is ?) | |||
| Infobox references | |||
tert-Amyl alcohol (TAA), systematic name: 2-methylbutan-2-ol (2M2B), is a branched pentanol used primarily as a pharmaceutical or pigment solvent. It remains liquid at room temperature making it a useful alternative to tert-butyl alcohol. It is a colorless liquid with a pungent odor of camphor. It is slightly soluble in water and miscibile organic solvents. Although it can be produced naturally, by the fermentation of ethanol, it is primarily produced synthetically via hydroformylation.
Production
Industrial
Like other oxo alcohols TAA is primarily produced via hydroformylation. The reaction of 2-methyl-2-butene with water in the presence of an acid catalyst yields TAA.[2][3]
Natural occurrence
Fusel alcohols including TAA are grain fermentation by-products and therefore trace amounts of TAA are present in many alcoholic beverages.[4] Trace levels of TAA have also been detected in various foodstuffs, including fried bacon, cassava,[5][6] rooibos tea[7] and fruits such as apple and pineapple.
Pharmacology
Between about 1880–1950, it was used as an anesthetic, with the contemporary name of amylene hydrate. It was mainly used as a solvent for tribromoethanol, forming "avertin fluid" at a 0.5 : 1 ratio of TAA to TBE. TAA was rarely used as a sole hypnotic because of the existence of more efficient drugs.[3]
Tertiary alcohols like TAA cannot be oxidised to aldehyde or carboxylic acid metabolites, which are often toxic; this makes them safer drugs than primary alcohols.[8] However, like other tertiary alcohol based anaesthetics (e.g. methylpentynol, ethchlorvynol) TAA was eventually superseded by safer and more effective agents.
TAA produces euphoria, sedative, hypnotic, and anticonvulsant effects similar to ethanol through ingestion or inhalation.[9] It is active in doses of 2,000–4,000 mg, making it 20 times more potent than ethanol.[10][11] Its hypnotic potency is between chloral hydrate and paraldehyde[12] and between benzodiazepines and ethanol.
In rats, TAA is primarily metabolized via glucuronidation, as well as by oxidation to 2-methyl-2,3-butanediol. It is likely that the same path is followed in humans,[13] though older sources suggest it is excreted unchanged.[3]
Overdose and toxicity
An overdose produces symptoms similar to alcohol poisoning and is a medical emergency due to the sedative/depressant properties. The oral LD50 in rats is 1000 mg/kg. The subcutaneous LD50 in mice is 2100 mg/kg.[14]
See also
References
- 1 2 Lomte, S. B.; Bawa, M. J.; Lande, M. K.; Arbad, B. R. (2009). "Densities and Viscosities of Binary Liquid Mixtures of 2-Butanone with Branched Alcohols at (293.15 to 313.15) K". Journal of Chemical & Engineering Data. 54: 127. doi:10.1021/je800571y.
- ↑ Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V2: 716. http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+5005
- 1 2 3 Adriani, John (1962). The Chemistry and Physics of Anesthesia. Second Edition. Illinois: Thomas Books. pp. 273–274. ISBN 9780398000110.
- ↑ George Milbry Gould; Richard John Ernst Scott (1919). The Practitioner's Medical Dictionary: Containing All the Words and Phrases Generally Used in Medicine and the Allied Sciences, with Their Proper Pronunciation, Derivation, and Definition. P. Blakiston's. p. 50. Retrieved February 7, 2013.
- ↑ Dougan, J.; Robinson, J. M.; Sumar, S.; Howard, G. E.; Coursey, D. G. (1983). "Some flavouring constituents of cassava and of processed cassava products". Journal of the Science of Food and Agriculture. 34 (8): 874. doi:10.1002/jsfa.2740340816.
- ↑ Ho, C. T.; Lee, K. N.; Jin, Q. Z. (1983). "Isolation and identification of volatile flavor compounds in fried bacon". Journal of Agricultural and Food Chemistry. 31 (2): 336. doi:10.1021/jf00116a038.
- ↑ Habu, Tsutomu; Flath, Robert A.; Mon, T. Richard; Morton, Julia F. (1 March 1985). "Volatile components of Rooibos tea (Aspalathus linearis)". Journal of Agricultural and Food Chemistry. 33 (2): 249–254. doi:10.1021/jf00062a024.
- ↑ Carey, Francis. Organic Chemistry (4 ed.). ISBN 0072905018. Retrieved 2013-02-05.
- ↑ Robert A. Lewis (1998). Lewis' Dictionary of Toxicology. CRC Press. p. 45. ISBN 1-56670-223-2.
- ↑ Hans Brandenberger & Robert A. A. Maes, ed. (1997). Analytical Toxicology for Clinical, Forensic and Pharmaceutical Chemists. p. 401. ISBN 3-11-010731-7.
- ↑ D. W. Yandell; et al. (1888). "Amylene hydrate, a new hypnotic". The American Practitioner and News. Lousville KY: John P. Morton & Co. 5: 88–89.
- ↑ F. A. Castle & C. Rice (March 1888). "Amylene and amylene hydrate". The American Druggist. 17 (3): 58–59.
- ↑ Collins, A. S.; Sumner, S. C.; Borghoff, S. J.; Medinsky, M. A. (1999). "A physiological model for tert-amyl methyl ether and tert-amyl alcohol: Hypothesis testing of model structures". Toxicological Sciences. 49 (1): 15–28. doi:10.1093/toxsci/49.1.15. PMID 10367338.
- ↑ Soehring, K.; Frey, H. H.; Endres, G. (1955). "Relations between constitution and effect of tertiary alcohols". Arzneimittel-Forschung. 5 (4): 161–165. PMID 14389140.