Ethyl butyrate

Base Information

• Chemical Name: Ethyl butyrate
• CAS No.: 105-54-4
• Molecular Formula: C6H12O2
• Molecular Weight: 116.16
• Hs Code.: 29156000
• European Community (EC) Number: 203-306-4
• NSC Number: 8857
• UN Number: 1180
• UNII: UFD2LZ005D
• DSSTox Substance ID: DTXSID6040111
• Nikkaji Number: J3.235B
• Wikipedia: Ethyl_butyrate
• Wikidata: Q412270
• RXCUI: 1314356
• Metabolomics Workbench ID: 46261
• ChEMBL ID: CHEMBL44800
• Mol file: 105-54-4.mol

Synonyms:butyric acid ethyl ester;ethyl butyrate

Chemical Property of Ethyl butyrate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 15.5 mm Hg ( 25 °C)
• Melting Point: -93.3 °C
• Refractive Index: n20/D 1.392(lit.)
• Boiling Point: 122.436 °C at 760 mmHg
• Flash Point: 19.444 °C
• PSA: 26.30000
• Density: 0.87 g/cm³
• LogP: 1.34960
• Storage Temp.: Flammables area
• Solubility.: Soluble in propylene glycol, paraffin oil, and kerosene.
• Water Solubility.: practically insoluble
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 116.083729621
• Heavy Atom Count: 8
• Complexity: 68.9
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Ethyl butyrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Esters (
• Canonical SMILES: CCCC(=O)OCC
• Description: Ethyl butyrate is an ester soluble in propylene glycol, paraffin oil, and kerosene. It has a fruity odor, similar to pineapple. Ethyl butyrate is present in many fruits e.g. apple, apricot, banana, plum, tangerine etc. Ethyl butyrate is used as an artificial flavoring resembling orange juice or pineapple in alcoholic beverages, as an ingredient of fragrance, and as a solvent and plasticizer for cellulose. It is also used in the production of polyvinyl butyral (PVB). Ethyl butyrate, also known as ethyl butanoate, or butyric ether, is an ester with the chemical formula CH3CH2CH2COO.CH2CH3.It is soluble in propylene glycol, paraffin oil, and kerosene.It has a fruity odor, similar to pineapple.
• Uses: Ethyl Butyrate is used in flavorings, extracts, perfumery, and as a solvent. These are not necessarily FDA approved indications, but instead are uses of liquid nitrogen.It is synthesized by reacting ethanol and butyric acid in a condensation reaction. Ethyl Butyrate is perceived as a tropical fruit, tutti fruity, mango or pineapple flavour. One of the ester flavours found in most beers, it can also be perceived as a slightly cheesy fruit flavour. Ethyl Butyrate generally occurs in beers due to fermentation and too much is normally considered an off flavour. Applications: artificial flavoring resembling orange juice or pineapple in alcoholic beverages, as a solvent in perfumes, and as a plasticizer for cellulose. Ethyl butyrate is used in flavors and fragrances. It is used as a solvent in perfumery products, and as a plasticizer for cellulose. It is used in the preparation of novel 2-cyanopyrimidines as cathespin K inhibitors. It is also used in the synthesis of pyridobenzimidazole derivatives exhibiting antifungal activity by the inhibition of β-1,6-glucan. It is commonly used as artificial flavoring resembling orange juice or pineapple in alcoholic beverages (e.g. martinis, daiquiris etc.), as a solvent in perfumery products, and as a plasticizer for cellulose. In addition, ethyl butyrate is often also added to orange juice, as most associate its odor with that of fresh orange juice. Ethyl butyrate is one of the most common chemicals used in flavors and fragrances. It can be used in a variety of flavors: orange (most common), cherry, pineapple, mango, guava, bubblegum, peach, apricot, fig, and plum. In industrial use, it is also one of the cheapest chemicals, which only adds to its popularity. manufacture of artificial rum; perfumery; the alcoholic solution constitutes the so-called "pineapple oil".

Technology Process of Ethyl butyrate

There total 157 articles about Ethyl butyrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

ethanol (64-17-5) + carbon monoxide (201230-82-2) + N-butylamine (109-73-9,85404-21-3) → N-butylformamide (871-71-6) + ethyl n-valerate (539-82-2) + N-(ethoxycarbonyl)butylamine (591-62-8) + butanoic acid ethyl ester (105-54-4)

Guidance literature:

With oxygen; Sulfate; zirconium(IV) oxide; palladium dichloride; at 170 ℃; for 3h; under 45003.6 Torr; Title compound not separated from byproducts;

DOI:10.1006/jcat.2001.3350

Reference yield: 79.0%

1-(5-bromo-1H-indol-1-yl)ethan-1-one (61995-52-6) + Ethyl 4-bromobutyrate (2969-81-5) → N-acetylindole (576-15-8) + diethyl suberate (2050-23-9) + ethyl 4-(1-acetyl-1H-indol-5-yl)butanoate (1365610-78-1) + C20H16N2O2 + butanoic acid ethyl ester (105-54-4)

Guidance literature:

With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 4,4'-Dimethoxy-2,2'-bipyridin; NiI₂*3.5H₂O; sodium iodide; zinc; at 20 - 60 ℃; for 19h; chemoselective reaction;

DOI:10.1021/ja301769r

Reference yield: 79.0%

Ethyl 4-bromobutyrate (2969-81-5) + p-bromophenylboronic acid pinacol ester (68716-49-4) → diethyl suberate (2050-23-9) + ethyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butanoate (1365610-75-8) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) + butanoic acid ethyl ester (105-54-4) + 4,4′-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1′-biphenyl (207611-87-8)

Guidance literature:

With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 1,10-Phenanthroline; NiI₂*3.5H₂O; sodium iodide; zinc; at 20 - 60 ℃; for 20h; chemoselective reaction;

DOI:10.1021/ja301769r

upstream raw materials:

butanoic acid anhydride

heptane-2,4-dione

ethanol

butyryloxy-acetic acid ethyl ester

Downstream raw materials:

4-heptanone

N-(2-hydroxyethyl)butyramide

4,6-Nonanedione

ethyl butyroyl acetate

Refernces

• 1、 Takami, Kazuaki,Mikami, Satoshi,Yorimitsu, Hideki,Shinokubo, Hiroshi,Oshima, Koichiro. "Triethylborane-induced radical reactions with gallium- and indium hydrides". . p. 6627 - 6635. Retrieved 2003.
• 2、 Larock. "-". . p. 834. Retrieved 1974.
• 3、 Huyser et al.. "-". . p. 4377. Retrieved 1965.
• 4、 Filler,R.,Naqvi,S.M.. "-". . p. 879 - 889. Retrieved 1963.
• 5、 Okayasu, Teruyuki,Saito, Kei,Nishide, Hiroyuki,Hearn, Milton T. W.. "Poly(vinylsulfonic acid)-grafted solid catalysts: New materials for acid-catalysed organic synthetic reactions". . p. 1981 - 1989. Retrieved 2010.
• 6、 Tundo. "-". . p. 2048. Retrieved 1979.
• 7、 Chi-San Chen. "-". . p. 213,215. Retrieved 1978.
• 8、 Fallavena, Lucas P.,Antunes, Fabio H. F.,Alves, Joana S.,Paludo, Natalia,Ayub, Marco A. Z.,Fernandez-Lafuente, Roberto,Rodrigues, Rafael C.. "Ultrasound technology and molecular sieves improve the thermodynamically controlled esterification of butyric acid mediated by immobilized lipase from Rhizomucor miehei". . p. 8675 - 8681. Retrieved 2014.
• 9、 Kumaravel, Sakthivel,Thiripuranthagan, Sivakumar,Radhakrishnan, Ramakrishnan,Erusappan, Elangovan,Durai, Mani,Devarajan, Arulselvan,Mukannan, Arivanandhan. "Liquid phase esterification of levulinic acid into ethyl levulinate over sulphobenzylated nanoporous Al-SBA-15 catalyst". . p. 6965 - 6977. Retrieved 2019.
• 10、 Mouat, Aidan R.,Lohr, Tracy L.,Wegener, Evan C.,Miller, Jeffrey T.,Delferro, Massimiliano,Stair, Peter C.,Marks, Tobin J.. "Reactivity of a Carbon-Supported Single-Site Molybdenum Dioxo Catalyst for Biodiesel Synthesis". . p. 6762 - 6769. Retrieved 2016.