Nitrogen → Hexadecanediol

HRID 2071887

Reaction equation

HRID 2071887 reaction equation
[O:1]1[CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:2]1.[OH:18]S(O)(=O)=O.N#N>>[CH:2]([OH:18])([OH:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 3

HCID 947NitrogenHCID 1118Sulfuric AcidHCID 237411,2-Epoxyhexadecane

Product 1

HCID 656980HexadecanediolYield 95%

Procedure

120 grams of random, internal epoxyhexadecane was placed in a glass-lined autoclave with 40 ml. of 10% H2SO4. The mixture was heated to 150° C. for 3 hours under 300 psi N2. Upon cooling, the product solidified in the autoclave. The aqueous portion was decanted, and the solid was dissolved in hot hexane. The solution was dried over anhydrous, MgSO4, filtered, and cooled. The resulting crystals were removed by filtration to yield approximately 95% of pure random, internal vicinal hexadecane diol.

Workup

  1. temperatureUpon cooling
  2. customThe aqueous portion was decanted
  3. dissolutionthe solid was dissolved in hot hexane
  4. dry with materialThe solution was dried over anhydrous, MgSO4
  5. filtrationfiltered
  6. temperaturecooled
  7. customThe resulting crystals were removed by filtration

Sources & evidence

ORD record
ord-a64193dfa94c40509bfdf109555e2396
Source dataset
uspto-grants-1977_09
Patent number
US04049585

Linked notes

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