Synthesis of butyl ether

Preparation of butyl ether (di-n-butyl ether; 1-butoxybutane; n-Butyl ether; butane, 1,1′-oxybis-)

Preparation of butyl ether (di-n-butyl ether; 1-butoxybutane; n-Butyl ether; butane, 1,1'-oxybis-)

Preparation of butyl ether (di-n-butyl ether; 1-butoxybutane; n-Butyl ether; butane, 1,1′-oxybis-)

For the preparation of butyl ether, the Dean-Stark apparatus is fitted with a round bottom flask and a condenser.

A glass apparatus for the preparation of butyl ether

A glass apparatus for the preparation of butyl ether

A small amount of water is placed in the Dean-Stark apparatus. A mixture of 62 ml (50 g) of n-butyl alcohol and with 9 ml (16 g) of concentrated sulfuric acid are added in the round bottom flask. The flask is gently heated so that the liquid refluxes and is condensed by the condenser. Water and n-butyl alcohol will first collect in the Dean-Stark apparatus, and when the combined volumes exceed certain volume (depending on Dean-Stark used), automatic separation of the two liquids will commence; the denser water will fall to the bottom of the tube and the lighter n-butyl alcohol will pass back into the flask. The heating is continued for 30-40 minutes and the temperature inside the flask rises to 134-135° C. The reaction is complete when 5-6 ml of water is collected in Dean-Stark apparatus. Further heating will merely result in considerable darkening of the mixture in the flask and the formation of the highly inflammable butylene. When the reaction is complete the reaction mixture is cooled to room temperature the contents of the flask and Dean-Stark apparatus are mixed and transferred into a separatory funnel containing 100 ml of water. The mixture is shaken and upper layer containing the crude ether mixed with a little unreacted n-butyl alcohol are separated, treated with 25 ml of cold 50% sulfuric acid by weight (from 20 ml of concentrated acid and 35 ml of water) for 2-3 minutes. The upper layer is separated and the extraction is repeated with another 25 ml of the sulfuric acid. Finally, the crude butyl ether is washed twice with 25 ml portions of water, dried with anhydrous calcium chloride, filtered into a 50 ml distilling flask, and purified by distillation. The fraction boiling at 139-142° C is collected yielding 15 g of pure butyl ether.

An alternative method for isolating the butyl ether utilizes the fact that n-butyl alcohol is soluble in saturated calcium chloride solution whilst butyl ether is slightly soluble. The reaction mixture is cooled in ice and transferred to a separatory funnel, where it is washed cautiously with 100 ml of 2-3N sodium hydroxide solution; the washings should be alkaline to litmus. Then washed with 30 ml of water, followed by 30 ml of saturated calcium chloride solution, dried with anhydrous calcium chloride, filtered and distilled, collecting the butyl ether at 139-142°. The yield is 20 g.

A text book of practical organic chemistry, by A. I. Vogel, 3011-313, 1974

IUPAC Name

1-butoxybutane

InChI

InChI=1S/C8H18O/c1-3-5-7-9-8-6-4-2/h3-8H2,1-2H3

InChI Key

DURPTKYDGMDSBL-UHFFFAOYSA-N

Canonical SMILES

CCCCOCCCC

MeSH Synonyms

dibutyl ether

Depositor-Supplied Synonyms

Butyl ether, DIBUTYL ETHER, Di-n-butyl ether, 1-Butoxybutane, n-Butyl ether, Butane, 1,1′-oxybis-, 142-96-1, Dibutyl oxide, Butyl oxide, Ether butylique, 1,1′-oxydibutane, 1,1′-Oxybis(butane), n-Dibutyl ether, NSC 8459, Ether butylique [French], butoxybutane, CCRIS 6010, HSDB 306, DURPTKYDGMDSBL-UHFFFAOYSA-N, dibutylether, DBE CDR-grade, EINECS 205-575-3, SBB060059, BRN 1732752, AI3-00402, butylether, monobutylether, monobutyl ether, n-butylether, di-n-butylether, 1-Butoxy-butane, 5-Oxanonane, di-n butyl ether, di(1-butyl) ether, 1,1′-Oxybisbutane, Butane,1′-oxybis-, Butyl ether (8CI), ACMC-1BPWC, AC1L1RXJ, DSSTox_CID_2007, UNII-PBM2R52P5G, DSSTox_RID_76456, PBM2R52P5G, DSSTox_GSID_22007, SCHEMBL15167, KSC175G7F, 10917_ALDRICH, 80103_ALDRICH, CHEMBL48132, 110280_ALDRICH, 271454_ALDRICH, WLN: 4O4, Jsp002525, (n-C4H9)2O, 10917_FLUKA, 34462_FLUKA, 80103_FLUKA, CTK0H5372, NSC8459, MolPort-001-770-815, 34462_SIAL, 110280_SIAL, 271454_SIAL, NSC-8459, Tox21_201037, ANW-42155, LS-842, STL280282, ZINC01586751, AKOS015915425, MCULE-8568026186, RP19930, RTR-005486, TRA0076468, UN 1149, NCGC00248903-01, NCGC00258590-01, AN-23250, CAS-142-96-1, KB-50120, TR-005486, 400-EP2272537A2, 400-EP2272842A1, 400-EP2275411A2, 400-EP2301927A1, 400-EP2305666A1, 400-EP2374538A1, 400-EP2377847A1, B0721, FT-0625171, ST51046309, 26065-EP2269986A1, 26065-EP2275423A1, 26065-EP2287152A2, 26065-EP2289879A1, 26065-EP2295399A2, 26065-EP2301918A1, 26065-EP2305825A1, 26065-EP2311802A1, 26065-EP2311803A1, 26065-EP2314558A1, 26065-EP2371795A1, 26065-EP2380568A1, 4-01-00-01520 (Beilstein Handbook Reference), A807991, I14-5863, InChI=1/C8H18O/c1-3-5-7-9-8-6-4-2/h3-8H2,1-2H

Removed Synonyms

CID8909, DBE

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