Ethyl butyrate: Difference between revisions

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| ImageFile1 = Ethyl-butyrate3D.png

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| PIN = Ethyl butanoate <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->

| OtherNames = Ethyl butyrate acid ethyl ester Butyric ether UN 1180

|Section1={{Chembox Identifiers

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

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

| ChEBI = 88764

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|ChEMBL = 44800

| EINECS = 203-306-4

| PubChem = 7762

| SMILES = CCCC(=O)OCC

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|Section2={{Chembox Properties

| Properties_ref = <ref name=Merck>''[[Merck Index]]'', 12th Edition, '''3822'''</ref>

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| Appearance = Colorless liquid with fruity odor

| Density = 0.879 g/cm³

| =

| BoilingPtC = 120–121

| Solubility =

| VaporPressure = 1510Pa (11.3)

| MagSus = −77.7×10⁻⁶ cm³/mol

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|Section7={{Chembox Hazards

| NFPA-H = 1

| NFPA-F = 2

| NFPA-R = 0

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| GHSSignalWord = Warning

| HPhrases = {{H-phrases|226}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|280|303+361+353|370+378|403+235|501}}

| FlashPtF = 78

| FlashPt_notes = c.c.

| AutoignitionPtC = 463

| LD50 = 1350 mg/kg (oral, rat)<ref name=Merck/>

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'''Ethyl butyrate''', also known as '''ethyl butanoate''', or '''butyric ether''', is an [[ester]] with the chemical formula CH₃CH₂CH₂COOCH₂CH₃. It is soluble in [[propylene glycol]], [[paraffin oil]], and [[kerosene]].

==Uses==

It is commonly used as [[artificial flavor]]ing resembling [[orange juice]]<ref>{{cite magazine|url=http://www.newyorker.com/online/blogs/books/2009/05/ask-an-academic-orange-juice.html|title=Ask an Academic: Orange Juice|author=Andrea Walker|date=12 May 2009|magazine=The New Yorker}}</ref> and is hence used in nearly all orange juices sold in the US, including those sold as "[[Tropicana Products|fresh]]" or “concentrated".<ref>{{cite book |last1=Hamilton |first1=Alissa |title=Squeezed |publisher=Yale University}}</ref> It is also used in alcoholic beverages (e.g. martinis, daiquiris etc.), as a solvent in [[perfume]]ry products, and as a [[plasticizer]] for [[cellulose]].

Ethyl butyrate is one of the most common chemicals used in and . It can be used in a variety of flavors orange (most common), cherry, pineapple, mango, guava, bubblegum, peach, apricot, fig, and plum. its also one of the cheapest chemicals, which only adds to its popularity.

==Production==

It can be synthesized by reacting [[ethanol]] and [[butyric acid]]. This is a [[condensation reaction]], meaning water is produced in the reaction as a byproduct. Ethyl butyrate from natural sources can be distinguished from synthetic ethyl butyrate by [[Isotope analysis|Stable Isotope Ratio Analysis]] (SIRA).<ref name=Ashurst98>{{cite book|last1=Ashurst|first1=P.R.|last2=Dennis|first2=M.J.|title=Analytical methods of food authentication|date=1998|publisher=Blackie Academic & Professional|location=London|isbn=9780751404265|edition=1st|url=https://books.google.com/books?id=80qArVT12FwC&pg=PA22|access-date=27 January 2016}}</ref>

{{Refimprove-section|date=January 2017}}

| 296°C (569 K)

| 2.38mol.l

| [[Refractive index]] (n) at 20°C

{{reflist}}

* [http://../// MSDS sheet]

* [http://cat.inist.fr/?aModele=afficheN&cpsidt=3822500 Sorption of ethyl butyrate and octanal constituents of orange essence by polymeric adsorbents]

* [http://cat.inist.fr/?aModele=afficheN&cpsidt=16129526 Biosynthesis of ethyl butyrate using immobilized lipase: a statistical approach]

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[[Category:]]

[[Category:Sweet-smelling chemicals]]