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Methyl trioctyl ammonium chloride

Basic information Description Reference Safety Supplier Related

Methyl trioctyl ammonium chloride Basic information

Product Name:
Methyl trioctyl ammonium chloride
Synonyms:
  • TRICAPRYLMETHYLAMMONIUM CHLORIDE
  • TRICAPRYLYLMETHYLAMMONIUM CHLORIDE
  • TRICAPRYLYL MONOMETHYLAMMONIUM CHLORIDE
  • TRI-N-OCTYLMETHYLAMMONIUM CHLORIDE
  • TRIOCTYLMETHYLAMMONIUM CHLORIDE
  • TOMAC
  • TricapryL
  • CAPRIQUAT
CAS:
5137-55-3
MF:
C25H54N.Cl
MW:
404.16
EINECS:
225-896-2
Product Categories:
  • organic intermediates
  • Quaternary ammonium salt
  • Industrial/Fine Chemicals
  • Ammonium Chlorides (Quaternary)
  • Quaternary Ammonium Compounds
Mol File:
5137-55-3.mol
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Methyl trioctyl ammonium chloride Chemical Properties

Melting point:
-20°C
Boiling point:
240°C
Density 
0.884 g/mL at 25 °C(lit.)
vapor pressure 
0Pa at 25℃
refractive index 
n20/D 1.4665(lit.)
Flash point:
>230 °F
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
soluble in Chloroform, Hexanes
form 
Viscous Liquid
color 
Colourless to pale orange
Odor
Ammonical
Water Solubility 
Partially insoluble
Sensitive 
Hygroscopic
BRN 
4039255
Stability:
Stable. Incompatible wth strong oxidizing agents. Hygroscopic.
InChIKey
XKBGEWXEAPTVCK-UHFFFAOYSA-M
LogP
4.5 at 25℃
CAS DataBase Reference
5137-55-3(CAS DataBase Reference)
EPA Substance Registry System
Methyltrioctylammonium chloride (5137-55-3)
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Safety Information

Hazard Codes 
Xn,N,C
Risk Statements 
22-38-41-50/53-36/37/38-20/21/22-34
Safety Statements 
26-39-60-61-36-45-36/37/39
RIDADR 
UN 2810 6.1/PG 3
WGK Germany 
3
RTECS 
UZ2997500
3-10
HazardClass 
6.1
PackingGroup 
III
HS Code 
29239000

MSDS

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Methyl trioctyl ammonium chloride Usage And Synthesis

Description

Methyltrioctylammonium chloride is a water insoluble quaternary ammonium salt, which is widely used as a counter ion in solvent extraction of anionic metal complexes. It is widely used as a phase transfer catalyst for the catalytic oxidation of cyclohexene to 1,6-hexanedioic acid. In comparison to traditional method of oxidizing cyclohexanol or cyclohexanone with nitric acid or potassium permanganate, the usage of methyltrioctylammonium chloride is a more environmentally friendly reaction.

Reference

N. Pourreza, H. Zavvar Mousavi, Determination of cadmium by flame atomic absorption spectrometry after preconcentration on naphthalene– methyltrioctylammonium chloride adsorbent as tetraiodocadmate (II) ions, Analytica Chimica Acta, 2004, vol. 503, pp. 279-282

Chemical Properties

viscous colourless to pale orange liquid

Uses

Methyltrioctylammonium chloride can be used:

  • As a catalyst in the synthesis of acridine dione derivatives from aromatic aldehyde, dimedone and amines under ultrasonic irradiations.
  • As a catalyst in the synthesis of extended π-systems using aromatic aldehydes and methyldiazines.
  • As a component of a catalytic system used in the Suzuki-Miyaura cross-coupling reaction of a variety of aryl and heteroaryl chlorides in H2O.

Uses

Mixture of C8 and C10 chains with C8 predominating. Used as a metal extraction reagent and a phase-transfer catalyst.

Definition

ChEBI: An organic chloride salt having methyltrioctylammonium as the cation.

Flammability and Explosibility

Not classified

Safety Profile

Poison by ingestion and intraperitoneal routes. When heated to decomposition it emits very toxic fumes of NOx, NH3, and Cl-.

Purification Methods

A 30% (v/v) of Aliquat 336 solution in *benzene is washed twice with an equal volume of 1.5M HBr. [Petrow & Allen, Anal Chem 33 1303 1961.] It is purified by dissolving 50g in CHCl3 (100mL) and shaking with 20% NaOH solution (200mL) for 10minutes, and followed by 20% NaCl (200mL) for 10minutes. It is then washed with a small volume of H2O and filtered through a dry filter paper [Adam & Pribil Talanta 18 733 1971]. n-Alkylammonium chloride n=2,4,6. Recrystallise them from EtOH or an EtOH/Et2O mixture. [Hashimoto & Thomas J Am Chem Soc 107 4655 1985, Chu & Thomas J Am Chem Soc 108 6270 1986.] n-Alkyltrimethylammonium bromide n=10,12,16. Recrystallise them from an EtOH/Et2O mixture. [Hashimoto & Thomas J Am Chem Soc 107 4655 1985.]

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