Diacetyl peroxide
{{Chembox
| Watchedfields = changed
| verifiedrevid = 440123866
| ImageFile = Diacetyl peroxide.svg
| ImageSize = 180px
| ImageAlt = Skeletal formula
| ImageFile1 = Diacetyl-peroxide-3D-balls.png
| ImageSize1 =
| ImageAlt1 = Ball-and-stick model
| PIN = Acetic peroxyanhydride{{cite book |author=International Union of Pure and Applied Chemistry |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=The Royal Society of Chemistry |pages=829 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}
| OtherNames = acetyl peroxide (2:1); diacetyl peroxide; Peroxide, diacetyl; ethanoyl peroxide; acetyl ethaneperoxoate; ethanoyl ethane peroxoate; peracetic acid acetyl ester
|Section1={{Chembox Identifiers
| PubChem = 8040
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7749
| SMILES = O=C(OOC(=O)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H6O4/c1-3(5)7-8-4(2)6/h1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZQMIGQNCOMNODD-UHFFFAOYSA-N
| CASNo = 110-22-5
| CASNo_Ref = {{cascite|correct|??}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = FDU6Y8075A
| UNNumber = 2084
| EINECS = 203-748-8
}}
|Section2={{Chembox Properties
| C=4 | H=6 | O=4
| Appearance = Colorless crystals{{cite book|editor-last=Lewis|editor-first=R. J. Sr|title=Hawley's Condensed Chemical Dictionary|edition=13th|location=New York, NY|publisher=John Wiley & Sons|date=1997|page=13}}
| MeltingPtC = 30
| BoilingPtC = 121.4
| BoilingPt_notes = at 760 mmHg; {{convert|63|C|F K}} at 21 mmHg{{cite book|editor-last=Lide|editor-first=D. R.|title=CRC Handbook of Chemistry and Physics|edition=79th|location=Boca Raton, Florida|publisher=CRC Press|date=1998–1999|pages=3–250}}
| Solubility = slight in cold water
}}
|Section3={{Chembox Hazards
| MainHazards = Explosive, oxidizer
| FlashPtC = 32.2
| FlashPt_notes = ({{convert|45|C|F K|disp=sqbr}}{{cite web|url=http://nj.gov/health/eoh/rtkweb/documents/fs/0019.pdf|title=Acetyl peroxide|website=NJ.gov}})
| AutoignitionPt =
| NFPA-H = 1
| NFPA-F = 2
| NFPA-R = 4
}}
|Section6={{Chembox Explosive
| ShockSens = Very high / moderate when wet
| FrictionSens = Very high / moderate when wet
| DetonationV =
| REFactor =
}}
}}
Diacetyl peroxide is the organic peroxide with the formula (CH3CO2)2. It is a white solid or oily liquid with a sharp odor. As with a number of organic peroxides, it is explosive.{{cite book|last=Sax|first=N. I.|title=Dangerous Properties of Industrial Materials|url=https://archive.org/details/dangerouspropert00saxn|url-access=registration|edition=4th|location=New York, NY|publisher=Van Nostrand Reinhold|date=1975|page=[https://archive.org/details/dangerouspropert00saxn/page/357 357]|isbn=9780442273682}} It is often used as a solution, e.g., in dimethyl phthalate.
History
Diacetyl peroxide was discovered in 1858 by Benjamin Collins Brodie,{{cite journal|date=30 March 1881 |title=Anniversary Meeting|url=https://pubs.rsc.org/en/content/articlelanding/1881/ct/ct8813900177 |journal=Journal of the Chemical Society, Transactions |volume=39 |pages=177–201 |doi=10.1039/CT8813900177 |access-date=17 February 2022}} who obtained the compound by treating glacial acetic acid with barium peroxide in anhydrous diethyl ether.{{cite journal |last1=Brodie |first1=Benjamin Collins |date=1 January 1859 |title=I. Note on the formation of the peroxides of the radicals of the organic acids|journal=Proceedings of the Royal Society of London |volume=9 |pages=361–365 |doi=10.1098/rspl.1857.0087 |s2cid=97728118 |doi-access=free }}
Preparation
Diacetyl peroxide forms upon combining hydrogen peroxide and excess acetic anhydride. Peracetic acid is an intermediate.{{cite journal|url=http://cen.acs.org/articles/89/i2/Chemical-Safety-Synthesis-Procedure.html|title=Chemical Safety: Synthesis Procedure|journal=Chemical & Engineering News|volume=89|issue=2|page=2|date=2011-01-10}}
Safety
Consisting of both an oxidizer, the O-O bond and reducing agents, the C-C and C-H bonds, diacetyl peroxide is shock sensitive and explosive.{{cite book|author=National Fire Protection Association|title=Fire Protection Guide on Hazardous Materials|edition=7th|location=Boston, MA|publisher=National Fire Protection Association|date=1978|pages=49–110}}
The threshold quantity for Process Safety Management per Occupational Safety and Health Administration 1910.119 is {{convert|5000|lb|kg|abbr=on}} if the concentration of the diacetyl peroxide solution is greater than 70%.{{Cite web|url=http://www.osha.gov/pls/oshaweb/owadisp.show_document?p_table=STANDARDS&p_id=9761|title = 1910.119 App A - List of Highly Hazardous Chemicals, Toxics and Reactives (Mandatory) | Occupational Safety and Health Administration}}
There have been reports of detonation of the pure material. The 25% solution also has explosive potential.{{cite book|author=National Research Council|title=Prudent Practices for Handling Hazardous Chemicals in Laboratories|location=Washington, DC|publisher=National Academy Press|date=1981|page=106}} The crystalline peroxide is especially shock sensitive and a high explosion risk.{{cite book|last=Bretherick|first=L.|title=Handbook of Reactive Chemical Hazards|edition=4th|location=Boston, MA|publisher=Butterworth-Heinemann|date=1990|pages=453, 1104}}
Organic peroxides are all prone to exothermic decomposition, potentially leading to explosions and fire.{{Ullmann|first1=Herbert|last1=Klenk|first2=Peter H.|last2=Götz|first3=Rainer|last3=Siegmeier|first4=Wilfried|last4=Mayr|title=Peroxy Compounds, Organic|doi=10.1002/14356007.a19_199.pub2}}
Contact with liquid causes irritation of the exposed area. If ingested, it irritates the mouth and stomach.{{cite book|author=National Research Council|author-link=United States National Research Council|title=Prudent Practices for Handling Hazardous Chemicals in Laboratories|location=Washington, DC|publisher=National Academy Press|date=1981|page=106}}{{cite book|author=International Labour Office|title=Encyclopaedia of Occupational Health and Safety|edition=4th|volume=1–4|date=1998|location=Geneva|publisher=International Labour Office|page=104.349}}{{cite book|editor1-last=Clayton|editor1-first=G.D.|editor2-first=F.E.|editor2-last=Clayton|title=Patty's Industrial Hygiene and Toxicology|volume=2A–2F|edition=4th|location=New York, NY|publisher=John Wiley & Sons|date=1993–1994|page=545}}{{cite book|editor1-last=Mackison|editor1-first=F. W.|editor2-first=R. S.|editor2-last=Stricoff|editor3-first=L. J. Jr|editor3-last=Partridge|title=NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards|series=DHHS(NIOSH) Publication No. 81–123|location=Washington, DC|publisher=U.S. Government Printing Office|date=Jan 1981|page=1}}
References
{{Reflist|2}}
- {{cite web|url=http://lb.chemie.uni-hamburg.de/static/RN/1_109-52-4%20...%20110-85-0.php?content=127/MS8aBDeF|title=Peroxide, diacetyl (C4H6O4)|website=Landolt-Boernstein Substance/Property Index|access-date=2010-12-22|archive-date=2011-07-17|archive-url=https://web.archive.org/web/20110717191622/http://lb.chemie.uni-hamburg.de/static/RN/1_109-52-4%20...%20110-85-0.php?content=127/MS8aBDeF|url-status=dead}}
- {{cite web|url=http://www.bge.de/asp2/dms.asp?url=%2Fuvv%2F58%2Fanh2.htm|title=Zuordnung der Organischen Peroxide zu Gefahrgruppen nach § 3 Abs. 1|language=German|website=Berufsgenossenschaft Handel und Warendistribution|access-date=2010-12-22|archive-date=2011-07-18|archive-url=https://web.archive.org/web/20110718202451/http://www.bge.de/asp2/dms.asp?url=%2Fuvv%2F58%2Fanh2.htm|url-status=dead}}