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Aliquat 336

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Aliquat 336

Aliquat 336
Names
IUPAC name
N-Methyl-N,N,N-trioctylammonium chloride
Other names
Starks' catalyst; Tricaprylmethylammonium chloride, Methyltrioctylammonium chloride
Identifiers
 N
ChemSpider  Y
Jmol-3D images Image
Image
RTECS number UZ2997500
Properties
C25H54ClN
Molar mass 404.16 g·mol−1
Appearance Colorless viscous liquid
Density 0.884 g/cm3
Melting point −20 °C (−4 °F; 253 K)
Boiling point 225 °C (437 °F; 498 K)
Viscosity 1500 mPa·s at 30 °C
Hazards
Main hazards Toxic (USA)
Safety data sheet External MSDS
Harmful (Xn)
R-phrases R50/53
S-phrases S26 S39 S60 S61
Flash point 113 °C (235 °F; 386 K) (closed cup)
Related compounds
Related
Aliquat 100, Aliquat 134, Aliquat 175, Aliquat HTA-1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: Y/N?)

Aliquat 336 (Starks' catalyst) is a quaternary ammonium salt used as a phase transfer catalyst and metal extraction reagent. It contains a mixture of C8 (octyl) and C10 (decyl) chains with C8 predominating.

Applications

Aliquat 336 is used as a phase transfer catalyst,[1] including in the catalytic oxidation of cyclohexene to 1,6-hexanedioic acid.[2] This reaction is more environmentally friendly. It is an example of green chemistry, compared with the traditional method of oxidizing cyclohexanol or cyclohexanone with nitric acid or potassium permanganate, which produce hazardous wastes.

Aliquat 336 was used in the total synthesis of Manzamine A by Darren Dixon in an early step to the electrophile.[3]

References

  1. ^ C. M. Starks (1971). "Phase-transfer catalysis. I. Heterogeneous reactions involving anion transfer by quaternary ammonium and phosphonium salts". J. Amer. Chem. 93: 195.  
  2. ^ S. M. Reed; J. E. Hutchison (2000). "An Environmentally Benign Synthesis of Adipic Acid".  
  3. ^ Jakubec, Pavol; Hawkins, Alison; Felzmann, Wolfgang; Dixon, Darren J. (2012). "Total Synthesis of Manzamine A and Related Alkaloids".  
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