Aliquat 336

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Aliquat 336
Aliquat 336.svg
Aliquat-336-3D-vdW.png
Names
IUPAC name
N-Methyl-N,N,N-trioctylammonium chloride
Other names
Starks' catalyst; Tricaprylmethylammonium chloride, Methyltrioctylammonium chloride
Identifiers
  • 63393-96-4 ☒N
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.023.542 Edit this at Wikidata
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 checkY
    Key: XKBGEWXEAPTVCK-UHFFFAOYSA-M checkY
  • 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 at 30 °C
Hazards
Main hazards Toxic (USA)
Safety data sheet (SDS) External MSDS
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Signal word
 Danger
H301, H315, H318, H319, H410
P264, P270, P273, P280, P301+P310, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P337+P313, P362, P391, P405, P501
Flash point 113 °C (235 °F; 386 K) (closed cup)
Related compounds
Related
, , ,
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N  (what is checkY☒N ?)
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 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[]

  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. S2CID 95868263.
  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.
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