1-Phenylethanol

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1-Phenylethanol
Methylphenylcarbinol.svg
Names
IUPAC name
1-Phenylethanol
Other names
Styrallyl alcohol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.461 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-707-1
PubChem CID
UNII
UN number 2937
  • InChI=1S/C8H10O/c1-7(9)8-5-3-2-4-6-8/h2-7,9H,1H3
    Key: WAPNOHKVXSQRPX-UHFFFAOYSA-N
  • CC(C1=CC=CC=C1)O
Properties
C8H10O
Molar mass 122.167 g·mol−1
AppearanceColourless liquid with a floral [1] or almond-like odor [2]
Melting point 20.7 °C (69.3 °F; 293.8 K)
Boiling point 204 °C (399 °F; 477 K)
1.95 g dm−3 [3]
log P 1.4
Hazards
Flash point 93 °C (199 °F; 366 K) [4]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1-Phenylethanol is the organic compound with the formula C6H5CH(OH)CH3. It is one of the most commonly available chiral alcohols. It is a colorless liquid with a mild gardenia-hyacinth scent. [5]

Contents

Phenylethanol is an aromatic alcohol, it has the role of mouse metabolite. It is a natural product and is found in Cichorium endivia, Castanopsis cuspidata and other organisms. [6]

Natural occurrence

1-Phenylethanol is found in nature as a glycoside, together with its hydrolase β-primeverosidase in tea (Camellia sinensis) flowers. [7] It is also reportedly present in cranberries, grapes, chives, Scottish spearmint oil, cheeses, cognac, rum, white wine, cocoa, black tea, filbert, cloudberries, beans, mushrooms, and endives. [8]

Synthesis

Racemic 1-phenylethanol is produced by the reduction of acetophenone by sodium borohydride. Alternatively, benzaldehyde can be reacted with methylmagnesium chloride or similar organometallic compounds to afford racemic 1-phenylethanol.

Asymmetric hydrogenation of acetophenone by Noyori catalysts proceeds quantitatively (50 atm H2, room temperature, minutes) in >99% e.e. [9]

The organic oxidising agent ethylbenzene hydroperoxide yields 1-phenylethanol when reduced. Used for the epoxidation of propene, this coproduces propylene oxide, and is an important step in the PO/SM process for the production of styrene. [10]

Applications

In the final step of the PO/SM process, dehydration of 1-phenylethanol yields styrene, analogous to many other dehydrations of alcohols to yield alkenes. While secondary to the direct dehydrogenation of ethylbenzene, the PO/SM method remains industrially significant. This route accounted for approximately 15% of styrene production in the United States in 1993, [11] and has seen international development in the 21st century, especially in developing economies that have seen growth in demand for both styrene and propylene oxide. [12]

See also

References

  1. ↑ Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 759
  2. ↑ Gerhartz, W. (exec ed.). Ullmann's Encyclopedia of Industrial Chemistry. 5th ed.Vol A1: Deerfield Beach, FL: VCH Publishers, 1985 to Present., p. VA24 488
  3. ↑ Southworth GR, Keller JL; Water Air Soil Poll 28: 239-48 (1986)
  4. ↑ Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 325-71
  5. ↑
  6. ↑ PubChem. "1-Phenylethanol". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-09-10.
  7. ↑ Zhou, Ying; Dong, Fang; Kunimasa, Aiko; Zhang, Yuqian; Cheng, Sihua; Lu, Jiamin; Zhang, Ling; Murata, Ariaki; Mayer, Frank (2014-08-13). "Occurrence of glycosidically conjugated 1-phenylethanol and its hydrolase β-primeverosidase in tea (Camellia sinensis) flowers". Journal of Agricultural and Food Chemistry. 62 (32): 8042–8050. doi:10.1021/jf5022658. ISSN   1520-5118. PMID   25065942.
  8. ↑ Burdock, George A. (2005). Fenaroli's Handbook of Flavor Ingredients, Fifth Edition. CRC Press.
  9. ↑ Dub, Pavel A.; Gordon, John C. (2018). "The role of the metal-bound N–H functionality in Noyori-type molecular catalysts". Nature Reviews Chemistry. 2 (12): 396–408. doi:10.1038/s41570-018-0049-z. S2CID   106394152.
  10. ↑ USpatent 6504038B1,Jacobus Johannes Van Der Sluis,"Process for the preparation of styrene and propylene oxide",published 2003-01-07,issued 2003-01-07, assigned to Shell USA Inc
  11. ↑ Radian Corporation (1993-04-20). LOCATING AND ESTIMATING AIR EMISSIONS FROM SOURCES OF STYRENE (PDF) (Report). United States Environmental Protection Agency. p. 18. Retrieved 2024-05-06. The majority of styrene is produced by dehydrogenation of ethylbenzene, with about 15 percent produced by hydroperoxidation of ethylbenzene.
  12. ↑ O'Connor, Rhian (2017-07-06). "The propylene oxide problem". Independent Commodity Intelligence Services. ICIS Chemical Business. Retrieved 2024-05-06.
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