71.218.165.238 (talk) |
resummarize recent tox info with LD50 and citation, mention some drugs made from it, move instruction use (I have never seen it converted to styrene in a teaching lab) |
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===Precursor to resins=== |
===Precursor to resins=== |
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Commercially significant [[resin]]s are produced from treatment of acetophenone with [[formaldehyde]] and base. The resulting polymers are conventionally described with the formula [(C<sub>6</sub>H<sub>5</sub>C(O)CH]<sub>x</sub>(CH<sub>2</sub>)<sub>x</sub>}<sub>n</sub>, resulting from [[aldol condensation]]. These substances are components of [[coating]]s and [[ink]]s. Modified acetophenone-formaldehyde resins are produced by the hydrogenation of the aforementioned ketone-containing resins. The resulting [[polyol]] can be further crosslinked with [[diisocyanate]]s.<ref name=Ullmann/> These modified resins are again found in coatings, inks, as well as [[adhesive]]s. |
Commercially significant [[resin]]s are produced from treatment of acetophenone with [[formaldehyde]] and base. The resulting polymers are conventionally described with the formula [(C<sub>6</sub>H<sub>5</sub>C(O)CH]<sub>x</sub>(CH<sub>2</sub>)<sub>x</sub>}<sub>n</sub>, resulting from [[aldol condensation]]. These substances are components of [[coating]]s and [[ink]]s. Modified acetophenone-formaldehyde resins are produced by the hydrogenation of the aforementioned ketone-containing resins. The resulting [[polyol]] can be further crosslinked with [[diisocyanate]]s.<ref name=Ullmann/> These modified resins are again found in coatings, inks, as well as [[adhesive]]s. |
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===Precursor to styrene=== |
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===Use in pharmaceutical and related areas=== |
===Use in pharmaceutical and related areas=== |
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Acetophenone is a raw material for the synthesis of some pharmaceuticals<ref> |
Acetophenone is a raw material for the synthesis of some pharmaceuticals, examples include [[dextropropoxyphene]] and [[phenylpropanolamine]].<ref> |
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{{Cite book |
{{Cite book |
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| isbn = 978-0-8155-1144-1 |
| isbn = 978-0-8155-1144-1 |
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| title = Process Chemistry in the Pharmaceutical Industry, Volume 2 |
| title = Process Chemistry in the Pharmaceutical Industry, Volume 2 |
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| year = 2007 |
| year = 2007 |
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}}</ref> |
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===Niche uses=== |
===Niche uses=== |
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Acetophenone is |
Acetophenone is an ingredient in fragrances that resemble [[almond]], [[cherry]], [[honeysuckle]], [[jasmine]], and [[strawberry]]. It is used in chewing gum.<ref>{{Citation |
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| last = Burdock |
| last = Burdock |
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| first = George A. |
| first = George A. |
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| id = |
| id = |
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| isbn = 0-8493-3034-3}}</ref> |
| isbn = 0-8493-3034-3}}</ref> |
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===Laboratory reagent=== |
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== Natural occurrence == |
== Natural occurrence == |
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== Toxicity == |
== Toxicity == |
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⚫ | The [[LD50]] is 815 mg/kg (oral, rats).ref name=Ullmann/> Acetophenone is currently listed as a Group D [[carcinogen]] (Not Classifiable as to Human Carcinogenicity), indicating that it does not produce carcinogenic effects in humans, although no studies on humans have ever been conducted on acetophenones' carcinogenic potential. Studies have shown that acetophenone causes chromosomal damage in hamsters.<ref name=pubchem /> |
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Little is known about acetophenone toxicity, however reports of suspected airborne exposures have listed numerous symptoms including rash to the face, neck, arms, and legs, eye and throat irritation, headaches, dizziness, and nausea.<ref name=pubchem /> Studies have confirmed that acetophenone exposure (through various routes) may result in a weakened pulse, [[chemical burns]], reduced reflexes, [[respiratory depression]], generalized weakness, incoordination/[[ataxia]], [[hypothermia]], [[convulsions]], ocular damage, dilated pupils, [[olfactory bulb]] damage, [[anesthesia]], [[analgesia]], and a continuous decrease in [[hemoglobin]] levels. It is therefor recommended that exposure to acetophenone be avoided when possible and that workers who may be exposed to acetophenone be monitored for signs of toxic levels of exposure. |
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⚫ | Acetophenone is currently listed as a Group D [[carcinogen]] (Not Classifiable as to Human Carcinogenicity), indicating that it does not produce carcinogenic effects in humans, although no studies on humans have ever been conducted on acetophenones' carcinogenic potential. Studies have shown that acetophenone causes chromosomal damage in hamsters.<ref name=pubchem /> |
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== References == |
== References == |
Revision as of 11:50, 12 August 2013
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Names | |||
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IUPAC name
1-phenylethanone
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Other names
Phenyl methyl ketone, ACP, Phenylethanone
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Identifiers | |||
3D model (JSmol)
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard | 100.002.462 | ||
KEGG | |||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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Properties | |||
C8H8O | |||
Molar mass | 120.151 g·mol−1 | ||
Density | 1.028 g/cm³ | ||
Melting point | 19–20 °C | ||
Boiling point | 202 °C | ||
5.5 g/L at 25 °C 12.2 g/L at 80 °C | |||
Hazards | |||
NFPA 704 (fire diamond) | |||
Flash point | 77 °C | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances.[1]
Production
Acetophenone can be obtained by a variety of methods. In industry, acetophenone is recovered as a by-product of the oxidation of ethylbenzene, which mainly gives ethylbenzene hydroperoxide for use in the production of propylene oxide.[1]
Uses
Precursor to resins
Commercially significant resins are produced from treatment of acetophenone with formaldehyde and base. The resulting polymers are conventionally described with the formula [(C6H5C(O)CH]x(CH2)x}n, resulting from aldol condensation. These substances are components of coatings and inks. Modified acetophenone-formaldehyde resins are produced by the hydrogenation of the aforementioned ketone-containing resins. The resulting polyol can be further crosslinked with diisocyanates.[1] These modified resins are again found in coatings, inks, as well as adhesives.
Acetophenone is a raw material for the synthesis of some pharmaceuticals, examples include dextropropoxyphene and phenylpropanolamine.[2] [3]
Niche uses
Acetophenone is an ingredient in fragrances that resemble almond, cherry, honeysuckle, jasmine, and strawberry. It is used in chewing gum.[4] It is also listed as an approved excipient by the U.S. FDA.[5] In a 1994 report released by five top cigarette companies in the U.S., acetophenone was listed as one of the 599 additives to cigarettes.[6]
Laboratory reagent
In instructional laboratories,[citation needed] acetophenone is converted to styrene in a two step process that illustrates the reduction of carbonyls and the dehydration of alcohols:[clarification needed]
- 4 C6H5C(O)CH3 + NaBH4 + 4 H2O → 4 C6H5CH(OH)CH3 + NaOH + B(OH)3
A similar process is used industrially but the hydrogenation step to 1-phenylethanol is done over a copper catalyst.[1]
- C6H5CH(OH)CH3 → C6H5CH=CH2 + H2O
Being prochiral, acetophenone is also a popular test substrate for asymmetric transfer hydrogenation experiments.
Natural occurrence
Acetophenone occurs naturally in many foods including apple, cheese, apricot, banana, beef, and cauliflower. It is also a component of castoreum, the exudate from the castor sacs of the mature beaver.[7]
Pharmacology
In the late 19th and early 20th centuries, acetophenone was used in medicine.[8] It was marketed as a hypnotic and anticonvulsant under brand name Hypnone. The typical dosage was 0.12 to 0.3 milliliters.[9] It was considered to have superior sedative effects to both paraldehyde and chloral hydrate.[10] In humans, acetophenone is metabolized to benzoic acid, carbonic acid, and acetone.[11] Hippuric acid occurs an indirect metabolite and its quantity in urine may be used to confirm acetophenone exposure.[12]
Toxicity
The LD50 is 815 mg/kg (oral, rats).ref name=Ullmann/> Acetophenone is currently listed as a Group D carcinogen (Not Classifiable as to Human Carcinogenicity), indicating that it does not produce carcinogenic effects in humans, although no studies on humans have ever been conducted on acetophenones' carcinogenic potential. Studies have shown that acetophenone causes chromosomal damage in hamsters.[12]
References
- ^ a b c d Hardo Siegel, Manfred Eggersdorfer “Ketones” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, 2002, Wienheim. doi:10.1002/14356007.a15_077
- ^ Sittig, Marshall (1988). Pharmaceutical Manufacturing Encyclopedia. pp. 39, 177. ISBN 978-0-8155-1144-1.
- ^
Gadamasetti, Kumar (2007). Process Chemistry in the Pharmaceutical Industry, Volume 2. pp. 142–145. ISBN 978-0-8493-9051-7.
{{cite book}}
: Unknown parameter|coauthors=
ignored (|author=
suggested) (help) - ^ Burdock, George A. (2005), Fenaroli's Handbook of Flavor Ingredients (5th ed.), CRC Press, p. 15, ISBN 0-8493-3034-3
{{citation}}
: Cite has empty unknown parameters:|month=
and|chapterurl=
(help) - ^ http://www.accessdata.fda.gov/scripts/cder/iig/index.cfm
- ^ "What's in a cigarette?". Archived from the original on 23 May 2006. Retrieved 2006-05-31.
{{cite web}}
: Unknown parameter|deadurl=
ignored (|url-status=
suggested) (help) - ^ Pheromonal activity of single castoreum constituents in beaver,Castor canadensis., Müller-Schwarze, D and Houlihan, P.W., Journal of Chemical Ecology, April 1991, Volume 17, Number 4, Springer Netherlands, doi:10.1007/BF00994195
- ^ The Merck Index, 12th Edition
- ^ Bartholow, Roberts. "A Practical Treatise On Materia Medica And Therapeutics." Appleton & Co, 1908.
- ^ Norman, Conolly. "Cases illustrating the sedative effects of aceto-phenone." Journal of Mental Science, Vol 32, p 519. 1887.
- ^ "Hypnone - The new hypnotic." J Am Med Assoc. Vol 5, p 632. 1885. doi:10.1001/jama.1885.02391220016006
- ^ a b "Acetophenone Compound Summary".