Synthesis of n-decane

Preparation of n-decane

Preparation of n-decane from n-amyl bromide and sodium

Preparation of n-decane from n-amyl bromide and sodium

Preparation of n-decane from n-amyl bromide and sodium

23 grams of clean sodium are cut into small pieces and introduced into a dry 1000 ml round-bottomed flask, which is fitted with an efficient condenser and a dropping funnel. 62 ml (or 75.5 grams) of n-amyl bromide (or 99 grams (65.5 ml) of n-amyl iodide) (previously dried over anhydrous sodium or magnesium sulfate) are added in a dropping funnel and about 5 ml of n-amyl bromide are introduced into the flask. If no reaction sets in, the flask gently warmed and the heating source is removed immediately when the reaction commences (the sodium will acquire a blue color). When the reaction subsides, the contents of the flask are mixed well, leading further reaction and some of the sodium may melt. A further 5 ml of n-amyl bromide are added, and the contents of the flask are mixed. When the reaction has slowed down, the above process is repeated until all the 62 ml of n-amyl bromide has been transferred to the flask. This can take up to 1.5 hours. Then the mixture is allowed to stand for 1-2 hours. Through the dropping funnel, 50 ml of ethanol dropwise over 1.5 hours are added, followed by 50 ml of 50% alcohol during 30 minutes, and 50 ml of distilled water over 15 minutes. During the addition, the reaction flask is mixed from time to time. 2-3 small pieces of porous porcelain are added and the mixture is reflux for 3 hours. During this time, any unreacted n-amyl bromide will be hydrolyzed. In order to obtain n-decane, a large excess of water is added and the upper layer containing crude n-decane is separated. The crude product is washed once with an equal volume of water and dried with anhydrous magnesium sulfate. The crude n-decane is purified by distillation, collecting fraction boiling at 171-174° C. The yield of n-decane is 28 grams.

All hydrocarbons prepared by the Wurtz reaction contain small quantities of unsaturated hydrocarbons. These may be removed by shaking repeatedly with 10% of the volume of concentrated sulfuric acid until the acid is no longer colored. The purified hydrocarbon is washed with water, 10% sodium carbonate solution, water (twice), and dried with anhydrous magnesium or calcium sulfate. The hydrocarbon is then distilled from sodium; two distillations are usually necessary to obtain a perfectly pure product. The residual sodium is destroyed by treatment with methanol.

A text book of practical organic chemistry, by A. I. Vogel, 236-237, 1974

IUPAC Name

decane

InChI

InChI=1S/C10H22/c1-3-5-7-9-10-8-6-4-2/h3-10H2,1-2H3

InChI Key

DIOQZVSQGTUSAI-UHFFFAOYSA-N

Canonical SMILES

CCCCCCCCCC

MeSH Synonyms

decane

Depositor-Supplied Synonyms

DECANE, n-Decane, 124-18-5, Decyl hydride, HSDB 63, CCRIS 653, Decane Fraction, CHEBI:41808, DIOQZVSQGTUSAI-UHFFFAOYSA-N, NSC 8781, EINECS 204-686-4, UN2247, BRN 1696981, AI3-24107, DSSTox_CID_4913, DSSTox_RID_77577, DSSTox_GSID_24913, CAS-124-18-5, D10, decan, normal-decane, Nonane, methyl-, Decane, n-, ACMC-1BUCN, Alkanes, C10-18, AC1Q2VXY, (C10-C18) Alkanes, D901_ALDRICH, UNII-NK85062OIY, D901_SIAL, KSC179Q2P, 30570_ALDRICH, 442669_SUPELCO, 457116_ALDRICH, AC1L268C, CHEMBL134537, NK85062OIY, QSPL 111, WLN: 10H, Jsp001609, n-C10H22, 30540_FLUKA, 30570_FLUKA, CTK0H9827, N-DECANE, CERTIFIED GRADE, NSC8781, MolPort-001-783-724, LTBB002320, 457116_SIAL, NSC-8781, Tox21_201881, Tox21_300336, ANW-42089, LMFA11000568, LS-693, STL280316, AKOS005145676, DB02826, MCULE-6071426098, RP20784, RTR-003754, TRA0023373, UN 2247, n-Decane [UN2247] [Flammable liquid], NCGC00247996-01, NCGC00247996-02, NCGC00254283-01, NCGC00259430-01, AN-22946, I932, KB-49638, n-Decane [UN2247] [Flammable liquid], TR-003754, D0011, S0282, S0554, 4-01-00-00464 (Beilstein Handbook Reference), 3B4-0751, I14-17989, DBF497D1-4529-4457-841E-9D33CDF22B1C, InChI=1/C10H22/c1-3-5-7-9-10-8-6-4-2/h3-10H2,1-2H, Reference Material for Flash Point Certified by The Japan Petroleum Institute, Decane, 28598-83-6, 63335-87-5, 73138-29-1

Removed Synonyms

Pentadecane, Tridecane, Undecane,

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