Β-Propiolactone: Difference between revisions

{{Redirect|Propiolactone|α-propiolactone|Methyloxiranone}}

{{lowercase title}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 444422830

| Name = β-Propiolactone

| ImageFile = Beta-Propiolactone-2D-skeletal.svg

| ImageSize = 120px

| ImageName = Skeletal formula

| ImageFile1 = Beta-Propiolactone-3D-balls.png

| ImageSize1 = 180px

| ImageName1 = Balla-and-stick model

| PIN = Oxetan-2-one

| OtherNames = Propiolactone<br />2-Oxetanone<br />3-Hydroxypropanoic acid lactone

|Section1={{Chembox Identifiers

| CASNo = 57-57-8

| CASNo_Ref = {{cascite|correct|CAS}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 49073

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1200627

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| DrugBank = DB09348

| PubChem = 2365

| RTECS = RQ7350000

| UNNumber = 2810

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 6RC3ZT4HB0

| EINECS = 200-340-1

|Section2={{Chembox Properties

| C=3 | H=4 | O=2

| Appearance = Colorless liquid

| Odor = slightly sweet<ref name=PGCH/>

| Density = 1.1460 g/cm³

| MeltingPtC = -33.4

| BoilingPtC = 162

| BoilingPt_notes = (decomposes)

| RefractIndex = 1.4131

| Solubility = 37 g/100 mL

| SolubleOther = Miscible

| Solvent = organic solvents

| VaporPressure = 3 mmHg (25°C)<ref name=PGCH/>

|Section3={{Chembox Hazards

| IDLH = Ca [N.D.]<ref name=PGCH>{{PGCH|0528}}</ref>

| REL = Ca<ref name=PGCH/>

| PEL = OSHA-Regulated [[carcinogen]]<ref name=PGCH/>

| FlashPtF = 165

| FlashPt_ref = <ref name=PGCH/>

| ExploLimits = 2.9%-?<ref name=PGCH/>

| GHSPictograms = {{GHS06}}{{GHS07}}{{GHS08}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|315|319|330|350}}

| PPhrases = {{P-phrases|201|202|260|264|271|280|281|284|302+352|304+340|305+351+338|308+313|310|320|321|332+313|337+313|362|403+233|405|501}}

}}

'''β-Propiolactone''', often simply called '''propiolactone''', is an [[organic compound]] with the formula {{chem2|CH2CH2CO2}}. It is a [[lactone]] family, with a four-membered ring. It is a colorless liquid with a slightly sweet odor, highly soluble in water and organic solvents.<ref name="nih"/><ref name="merck">''Merck Index'', 12th Edition, entry 8005.</ref> The carcinogenicity of this compound has limited its commercial applications.<ref>{{cite book |doi=10.1002/14356007.a15_063 |chapter=Ketenes |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2001 |last1=Miller |first1=Raimund |last2=Abaecherli |first2=Claudio |last3=Said |first3=Adel |last4=Jackson |first4=Barry |isbn=978-3-527-30385-4 }}</ref>

==Production==

β-Propiolactone is prepared industrially by the reaction of [[formaldehyde]] and [[ethenone]] in the presence of [[aluminium chloride|aluminium-]] or [[zinc chloride]] as catalyst:<ref name=Ullmann>{{Ullmann|doi=10.1002/14356007.a13_507|title=Hydroxycarboxylic Acids, Aliphatic|year=2000|last1=Miltenberger|first1=Karlheinz}}</ref>

[[File:Industrial synthesis of beta-propiolactone.svg|frameless|upright=2.2|Industrial synthesis of beta-propiolactone]]

In the research laboratory, propiolactones have been produced by the [[carbonylation]] of [[epoxide]]s.<ref>{{cite journal|title=Low Pressure Carbonylation of Epoxides to β-Lactones |author=John W. Kramer |author2=Daniel S. Treitler |author3=Geoffrey W. Coates|journal=Org. Synth.|year=2009|volume=86|page=287|doi=10.15227/orgsyn.086.0287|doi-access=free}}</ref>

==Reactions and applications==

It reacts with many nucleophiles in a ring-opening reactions. With water [[hydrolysis]] occurs to produce [[3-Hydroxypropionic acid|3-hydroxypropionic acid]] (hydracryclic acid). Ammonia gives the [[beta-Alanine|β-alanine]], which is a commercial process.<ref name=Ullmann/>

Propiolactone was once widely produced as an intermediate in the production of [[acrylic acid]] and its [[acrylate|esters]]. That application has been largely displaced in favor of safer and less expensive alternatives. β-Propiolactone is an excellent sterilizing and sporicidal agent, but its carcinogenicity precludes that use.<ref name="nih"/> It is used to [[inactivated vaccine|inactivate]] a wide variety of viruses,<ref>{{cite journal|doi=10.1111/j.1749-6632.1960.tb40931.x|title=Investigations of the Use of Beta-Propiolactone in Virus Inactivation|year=1960|last1=Logrippo|first1=Gerald A.|journal=Annals of the New York Academy of Sciences|volume=83|issue=4|pages=578–594|pmid=14417982|bibcode=1960NYASA..83..578L|s2cid=6025589}}</ref> for example as a step in vaccine production.<ref>{{cite journal|journal=Science|title=Development of an inactivated vaccine candidate for SARS-CoV-2|author1=Qiang Gao |author2=Linlin Bao |author3=Haiyan Mao |author4=Lin Wang |author5=Kangwei Xu |author6=Minnan Yang |author7=Yajing Li |author8=Ling Zhu |author9=Nan Wang |author10=Zhe Lv |author11=Hong Gao |author12=Xiaoqin Ge |author13=Biao Kan |author14=Yaling Hu |author15=Jiangning Liu |author16=Fang Cai |author17=Deyu Jiang |author18=Yanhui Yin |author19=Chengfeng Qin |author20=Jing Li |author21=Xuejie Gong |author22=Xiuyu Lou |author23=Wen Shi |author24=Dongdong Wu |author25=Hengming Zhang |author26=Lang Zhu |author27=Wei Deng |author28=Yurong Li |author29=Jinxing Lu |author30=Changgui Li |author31=Xiangxi Wang |author32=Weidong Yin |author33=Yanjun Zhang |author34=Chuan Qin |date=2020-07-03|doi=10.1126/science.abc1932|volume=369|issue=6499|pages=77–81|pmid=32376603|pmc=7202686|bibcode=2020Sci...369...77G|doi-access=free}}</ref> The principal use of propiolactone is an intermediate in the synthesis of other chemical compounds.<ref name=Ullmann/>

[[File:AKDstructure.png|thumb|220 px|left|Structure of an [[alkyl ketene dimer]] (AKD), a propiolactone derivative that is used in papermaking.]]

==Safety==

β-Propiolactone is "reasonably anticipated to be a human carcinogen" ([[International Agency for Research on Cancer|IARC]], 1999).<ref name="nih">[http://ntp.niehs.nih.gov/ntp/roc/content/profiles/propiolactone.pdf "β-Propiolactone CAS No. 57-57-8"] - US Department of Health and Human Services, Report on Carcinogens, National Toxicology Program, Thirteenth Edition, 2 October 2014. Accessed on 2015-01-03.</ref> It is one of 13 "OSHA-regulated carcinogens," chemicals regarded occupational carcinogens by the U.S. [[Occupational Safety and Health Administration]], despite not having an established [[permissible exposure limit]].<ref name="cdc">[https://www.cdc.gov/niosh/npg/nengapdxb.html "Appendix B - Thirteen OSHA-Regulated Carcinogens"] - [[Centers for Disease Control and Prevention]]. Accessed on 2013-11-06.</ref>

* [[Malonic anhydride]] (2,4-oxetanone)

[[Category:Beta-lactones]]

[[Category:Sweet-smelling chemicals]]