Aliquat 336

Aliquat 336
IUPAC name N-Methyl-N,N-dioctyloctan-1-ammonium chloride
Other names Starks' catalyst; Tricaprylmethylammonium chloride, Methyltrioctylammonium chloride
Identifiers
CAS number	63393-96-4 Y
ChemSpider	19948 Y
RTECS number	UZ2997500
Jmol-3D images	Image 1 Image 2
SMILES CCCCCCCC[N+](CCCCCCCC)(C)CCCCCCCC.[Cl-] [Cl-].C(CCCCCC[N+](CCCCCCCC)(CCCCCCCC)C)C
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 Y Key: XKBGEWXEAPTVCK-UHFFFAOYSA-M Y 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
Properties
Molecular formula	C25H54ClN
Molar mass	404.16 g mol−1
Appearance	Colorless viscous liquid
Density	0.884 g/cm³
Melting point	-20 °C, 253 K, -4 °F
Boiling point	225 °C, 498 K, 437 °F
Viscosity	1500 mPa·s at 30 °C
Hazards
MSDS	External MSDS
EU classification	Harmful (Xn)
R-phrases	R22 R38 R41 R50/53
S-phrases	S26 S39 S60 S61
Main hazards	Toxic (USA)
Flash point	113 °C (closed cup)
Related compounds
Related	Aliquat 100, Aliquat 134, Aliquat 175, Aliquat HTA-1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

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.

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 and J.E. Hutchison (2000). "An Environmentally Benign Synthesis of Adipic Acid". J. Chem. Ed. 77 (12): 1627–8. doi:10.1021/ed077p1627.