Aliquat 336

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Aliquat 336
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Names
IUPAC name
N-Methyl-N,N,N-trioctylammonium chloride
Other names
Starks' catalyst; Tricaprylmethylammonium chloride, Methyltrioctylammonium chloride
Identifiers
63393-96-4 N
ChemSpider 19948 YesY
Jmol 3D model Interactive image
Interactive image
RTECS number UZ2997500
  • InChI=1S/C25H54N.ClH/c1-5-8-11-14-17-20-23-26(4,24-21-18-15-12-9-6-2)25-22-19-16-13-10-7-3;/h5-25H2,1-4H3;1H/q+1;/p-1 YesY
    Key: XKBGEWXEAPTVCK-UHFFFAOYSA-M YesY
  • InChI=1/C25H54N.ClH/c1-5-8-11-14-17-20-23-26(4,24-21-18-15-12-9-6-2)25-22-19-16-13-10-7-3;/h5-25H2,1-4H3;1H/q+1;/p-1
    Key: XKBGEWXEAPTVCK-REWHXWOFAD
  • CCCCCCCC[N+](CCCCCCCC)(C)CCCCCCCC.[Cl-]
  • [Cl-].C(CCCCCC[N+](CCCCCCCC)(CCCCCCCC)C)C
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
Vapor pressure {{{value}}}
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).
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Infobox references

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[citation needed] or potassium permanganate[citation needed], 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

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