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 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	19948 ;
ECHA InfoCard	100.023.542
PubChem CID	21218;
RTECS number	UZ2997500;
CompTox Dashboard (EPA)	DTXSID1044487 ;
	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/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
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H315, H318, H319, H400, H410
GHS precautionary statements	P264, P270, P273, P280, P301+310, P302+352, P305+351+338, P310, P321, P330, P332+313, P337+313, P362, P391, P405, P501
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. It is an ionic liquid.[1]

Applications

Organic Chemistry

Aliquat 336 is used as a phase transfer catalyst,[2] including in the catalytic oxidation of cyclohexene to 1,6-hexanedioic acid.[3] 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.[4]

Aliquat 336 was used in the total synthesis of manzamine A by Darren Dixon in an early step to the electrophile.[5]

Solvent extraction of metals

Aliquat 336 has been used for the extraction of metals, it does so by acting as a liquid anion exchanger. It is often used while diluted in hydrocarbon solvents such as aromatic kerosene. It is possible to use it in aliphatic kerosene but in such solvents often a phase modifier (typically a long chain alcohol) must be added to prevent the formation of third phase.

References

Litaiem, Yousra; Dhahbi, Mahmoud (2015). "Physicochemical Properties of an Hydrophobic Ionic Liquid (Aliquat 336) in a Polar Protic Solvent (Formamide) at Different Temperatures". Journal of Dispersion Science and Technology. 36 (5): 641. doi:10.1080/01932691.2013.862170.
C. M. Starks (1971). "Phase-transfer catalysis. I. Heterogeneous reactions involving anion transfer by quaternary ammonium and phosphonium salts". J. Am. Chem. Soc. 93: 195–199. doi:10.1021/ja00730a033.
S. M. Reed; J. E. Hutchison (2000). "An Environmentally Benign Synthesis of Adipic Acid". J. Chem. Educ. 77 (12): 1627–8. doi:10.1021/ed077p1627.
Ameta, Suresh C; Ameta, Rakshit (2013-09-11). Green Chemistry: Fundamentals and Applications. ISBN 9781466578265.
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. PMID 23039372.

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[1] Litaiem, Yousra; Dhahbi, Mahmoud (2015). "Physicochemical Properties of an Hydrophobic Ionic Liquid (Aliquat 336) in a Polar Protic Solvent (Formamide) at Different Temperatures". Journal of Dispersion Science and Technology. 36 (5): 641. doi:10.1080/01932691.2013.862170.

[2] C. M. Starks (1971). "Phase-transfer catalysis. I. Heterogeneous reactions involving anion transfer by quaternary ammonium and phosphonium salts". J. Am. Chem. Soc. 93: 195–199. doi:10.1021/ja00730a033.

[3] S. M. Reed; J. E. Hutchison (2000). "An Environmentally Benign Synthesis of Adipic Acid". J. Chem. Educ. 77 (12): 1627–8. doi:10.1021/ed077p1627.

[4] Ameta, Suresh C; Ameta, Rakshit (2013-09-11). Green Chemistry: Fundamentals and Applications. ISBN 9781466578265.

[5] 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. PMID 23039372.