Cannabaceae

thcscience_admin
1-Phenylethanol
Names
IUPAC name
1-Phenylethanol
Other names
Styrallyl alcohol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.461 Edit this at Wikidata
EC Number
  • 202-707-1
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
Appearance Colourless 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)[5]
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.[4]

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[edit]

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[edit]

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[edit]

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[edit]

References[edit]

  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. ^ a b Fenaroli's Handbook of Flavor Ingredients. Volume 2. Edited, translated, and revised by T.E. Furia and N. Bellanca. 2nd ed. Cleveland: The Chemical Rubber Co., 1975., p. 348
  5. ^ Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 325-71
  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. ^ US patent 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.
source: https://en.wikipedia.org/wiki/1-Phenylethanol

One thought on “Cannabaceae”

  1. Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
    View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction

Leave a Reply