Aliquat 336

Aliquat 336

Names
IUPAC name N-Methyl-N,N,N-trioctylammonium chloride
Other names Starks' catalyst; Tricaprylmethylammonium chloride, Methyltrioctylammonium chloride
Identifiers
CAS Number	63393-96-4
ChemSpider	19948
Jmol interactive 3D	Image Image
RTECS number	UZ2997500
InChI 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 Key: XKBGEWXEAPTVCK-UHFFFAOYSA-M 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
SMILES CCCCCCCC[N+](CCCCCCCC)(C)CCCCCCCC.[Cl-] [Cl-].C(CCCCCC[N+](CCCCCCCC)(CCCCCCCC)C)C
Properties
Chemical formula	C25H54ClN
Molar mass	404.16 g·mol^−1
Appearance	Colorless viscous liquid
Density	0.884 g/cm^3
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
EU classification (DSD)	Harmful (Xn)
R-phrases	R22 R38 R41 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).
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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 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. doi:10.1021/ja00730a033.
2. S. M. Reed; J. E. Hutchison (2000). "An Environmentally Benign Synthesis of Adipic Acid". J. Chem. Ed. 77 (12): 1627–8. doi:10.1021/ed077p1627.
3. Jakubec, Pavol; Hawkins, Alison; Felzmann, Wolfgang; Dixon, Darren J. (2012). "Total Synthesis of Manzamine A and Related Alkaloids". Journal of the American Chemical Society 134 (42): 17482–17485. doi:10.1021/ja308826x.