Trioctylmethylammonium chloride

Acids such as sulfuric or nitric acids or bases such as sodium hydroxide may catalyze the hydrolysis of PET. It has been demonstrated that the rate of alkaline PET hydrolysis increases in the presence of quaternary ammonium compounds.26 27 Niu et al.26 reported an increase in the rate of alkaline PET degradation in the presence of dodecylbenzyldimethylammonium chloride at 80°C. Polk et al.27 reported increases in the rate of sodium hydroxide depolymerization of PET in the presence of trioctylmethylammonium chloride, trioctyl-methylammonium bromide, and hexadecyltrimethylammonium bromide at 80° C. 

As expected, HTMAB made a respectable showing in these experiments. Trioctylmethylammonium chloride (TOMAC) and trioctylmetliylammonium bromide (TOMAB) outperformed all other catalysts. It was postulated that the three octyl groups were the proper length for solvation of the polymer while at the same time small enough to avoid sterically hindering the reaction. In order to determine if TOMAB could be used to catalyze PET depolymerization for more than one treatment cycle, the catalyst was recovered upon completion of one treatment and added to a second run for 60 min. Tetraethylammonium hydroxide (TEAOH) was studied as a catalyst in order to demonstrate the effect of hydroxide ion as a counterion. The percent PET conversion for the second cycle was 85.7% compared to a conversion of 90.4% for the first treatment cycle. 

There are a number of industrially important reactions where two liquid phases are involved and the aqueous phase contains ionic species. Here the rate may be severely limited due to low solubiblity of the reactant, located in the organic phase, in water. We would benefit from using a pha.se-transfer (PT) catalyst, which ferries the ionic species into the organic phase thus overcoming a severe limitation. Such PT catalysts are typically quaternary ammonium compounds like tetrabutylammonium halides, trioctylmethylammonium chloride, etc. (see also Section 3.8). 

FIG. 15 Potential response of anion ISFETs based on sol-gel-derived membranes encapsulating trioctylmethylammonium chloride ( ) and modified chemically by alkoxysilylated quaternary ammonium salt (12) (O) to CC-activity changes. (From Ref 50.)... 

Trioctylmethylammonium chloride [7] has been widely used as a phase transfer catalyst. This compound is slightly soluble in water and forms aggregates at very low concentrations (Okahata et al., 1977). Figure 3 shows surface tension data, which indicate aggregation occurring at 10-4-10-5 M. The dye probe method and conductance measurements suggest that the... 

As mentioned in Section 2, trioctylmethylammonium chloride [7] appears to form small, highly hydrophobic aggregates. Okahata et al. (1977) found that the reactivity of hydrophobic nucleophiles (hydroxamate and imidazole anion) was very much enhanced in the presence of this aggregate. Thus, the combination of LImAm [60] and [7] (7 x 10-5 M) was more than 10 times more reactive toward PNPA than [60] in micellar CTAB (1 x 10-3 M). Less hydrophobic nucleophiles were not activated. 

To a solution of me.vo-l,2-dibromo-l,2-diphenylethane (2 mmol) in benzene (5 ml) was added a 30% aqueous Na2CS3 solution (6 mmol) and trioctylmethylammonium chloride (0.08 mmol). The mixture was stirred... 

Fig. 2. a spectra showing the decay of a few 261Rf atoms in three sequential elution fractions from a column containing trioctylmethylammonium chloride. Reprinted from [17] with the permission from Excerpta Medica Inc. (2001). 

Most systems examined to date have employed the AOT anionic reversed micellar system (366-370). In one case, amylase was extracted using trioctylmethylammonium chloride (cationic surfactant) in isooctane (375) while in another, catalase was extracted using a cationic DTAB/octane/hexanol reversed micelle (377). In our own research, we have successfully employed nonionic Igepal CO-530 -CCl, cationic CTAB - hexanol, and zwitterionic lecithin - CC1, reversed micellar systems in the extraction of some amino acids and proteins (379). The availability of such a pool of different charge-type micellar systems allows one flexibility in the development of such extraction schemes. In fact, preliminary results seem to indicate that better extractions are obtainable in some instances via use of zwitterionic reversed micellar media (379). 

SYNS ALIQUAT336 AIJQUAT336N ALIQUAT 336-PTC N-METHYL-N,N-DIOCTYL-l-OCTAN-AiMINIUM CHLORIDE METHYLTRICAPRYLYL-AMMONIUM CHLORIDE 1-OCTANAMINIUM, N-METHYDN.N-DIOCTYL-, CHLORIDE (9CI) TRICAPRYLMETHYLAMMONIUM CHLORIDE TRICAPRYLYLMETHYLAMMONIUM CHLORIDE TRIOCTYLMETHYLAMMONIUM CHLORIDE... 

TRIOCTANOIN see TMOOOO TRIOCTANOYLGLYCEROL see TMOOOO TRI-n-OCTYL BORATE see TMO550 TRIOCTYL(BUTYLTHIO)STANNANE see BS0200 TRIOCTYLMETHYLAMMONIUM CHLORIDE see MQHOOO... 

Methyl methylthiomethyl sulfone and methylthiomethyl p-tosyl sulfone have been monoalkylated, benzylated or alkylsilylated with 1.5 equiv. of the electrophile in the presence of aqueous sodium hydroxide and trioctylmethylammonium chloride (TOMAC). Without doubt the organometallic is less reactive than the one derived from the corresponding sulfoxide since the reaction is rather slow with... 

Behr and Lehn (14) first demonstrated carrier-facilitated transport of amino acids through "liquid membranes" composed of a toluene layer floating on top of two isolated aqueous solutions. The carriers used were the quaternary ammonium salt Aliquat 336 (trioctylmethylammonium chloride) and the alkylated arylsulfonic acid dinonylnapthalenesulfonic acid. Amino acids were transported in the form of anions or cations, respectively, with the above carriers. The process is an ion-exchange process, as the carrier must exchange an ionized atom or molecule each time it forms a new ion pair (Figure 2). The net result of this type of carrier-facilitated transport process is that a solute ion is transported into the LM while an equal number of counterions are transported out of the LM. 

The last contribution quoted in this section is a phosphine-free hydroformylation process based on a liquid triphasic system consisting of isooctane, water and trioctylmethylammonium chloride (TOMAC). The hydroformylation of model olefins required neat RhCls only as catalyst precursor. In the triphasic system, the catalyst is confined in the TOMAC phase, likely in the form of an ion pair. Products are obtained in excellent yields (> 90% at 80 °C) and high regioselectivity (>98%) in favour of the branched aldehyde in the case of styrene, while the exo isomer was obtained in >90% selectivity in the case of norbornene. The products were easily removed and the catalyst was recycled several times, with no leaching of rhodium into the organic phase. 

MMTS MsOH NBS NHMDS NMP NMR PPb Ph Pr PTC rt TBDMS Tf THF THP TLC TMEDA TMS TMSOTf Tol TOMAC Ts TsOH UDP methyl methylthiomethyl sulfoxide (=FAMSO) methanesulfonic acid N-bromosuccinimide sodium hexamethyldisililazide /V-methyl-2-pyrrolidone nuclear magnetic resonance parts per billion phenyl propyl Phase transfer catalysis room temperature t-butyldimethylsilyl triflatc (trifluoromethanesulfonate) tetrahydrofuran 2-tetrahydro-2//-pyran-2-yl thin-layer chromatography /V./V./V /V -tetramethylethylenediamine trimethylsilyl trimethylsilyl triflate p-tolyl trioctylmethylammonium chloride tosyl p-toluenesulfonic acid ultrasonically dispersed potassium... 

Aroyl chlorides and aryl sulfonyl chlorides can also be employed as arylating agents under decarbonylative and desulfitative conditions respectively. Improved yields were reported by Dubbaka and Vogel [64] using Herrmann s palladacycle [63], arenesul-fonyl chlorides and bulky trioctylmethylammonium chloride under reflux conditions (Figure 3.11). 

This work was extended by Hulet et al. (1980) to the chloride complexes of rutherfordium. Computer automation was used to help perform the chemical operations rapidly and reproducibly. An HCl solution containing Rf was passed through an extraction chromatography column loaded with trioctylmethylammonium chloride which strongly extracts anionic chloride complexes. Such complexes are formed by the group IV elements such as rutherfordium while the actinides, and members of groups I and II, form weaker complexes and are not extracted. Thus, the actinide recoil products elute first and zirconium, hafnium and rutherfordium were shown to elute in a second fraction as expected for group IV elements. 

For example, hydroformylation of 1-dodecene has been carried out with a phosphabicyclononane-modified Co catalyst at 8.5 MPa syngas pressure (CO/H2 = 1 2) at 120 °C with a Co/P ratio of 1 2 to produce 55% isomeric Cj g alcohols [61]. RhClj immobilized on trioctylmethylammonium chloride operating in a multiphase Uquid system together with isooctane and water was developed for the conversion of tetradecene [62]. In more sophisticated approaches, phosphorus-modified Rh catalysts have been screened in biphasic systems, sometimes containing surface-active compounds [63]. Even internal olefins, such as (Z)-2-tridecene, have been used as substrates. Thus, by using a mixed, homogeneous Rh/Ru catalyst in a hydroformylation-hydrogenation protocol, 1-tetradecanol was obtained with a yield of 83% and with an Hb selectivity of 12 (see Section 5.2) [64]. 

When measuring the surface pressure isotherms, it is desirable that the values of the interfacial tension are not time-dependent. In this case, in the interfacial region a state is reached close to the equilibrium for the surfactant distribution between the phases [55]." If the surfactant is soluble in both phases, one should be careful in calculating the surface excess in such systems, and the surfactant distribution coefficient should be determined independently. For instance, trioctylmethylammonium chloride (Oct3MeNCl) in the benzene-water system has a distribution coefficient of the order of 10 [57]. The surface pressure isotherms at the benzene-water interface are almost independent of the phase in which Oct3MeNCl is dissolved. It means that in both cases Oct3MeNCl is almost completely located in the benzene phase, i.e. the surfactant distribution equilibrium is reached at the interface. Apparently, the anomalies in the... 

Reagents i, trioctylmethylammonium chloride-NaOH-HjO-toluene ii, H2O2-CH3CO2H ui, HCI-MeOH... 

Selective separation of lead(II) and cadmium(II) chloride complexes by both liquid membranes containing liquid anion-exchangers as mobile carriers and solid polymeric membranes with anion-exchange sites as fixed carriers is described by Hayashita in Chapter 21. A novel polymeric plasticizer membrane, which is composed of cellulose triacetate polymer as a membrane support, o-nitrophenyl octyl ether as a membrane plasticizer, and trioctylmethylammonium chloride as an anion-exchange carrier, provides enhanced permeation selectivity and efficiency. 

Jensen, M.P. Neuefeind, J. Beitz, J.V. Skanthakumar, S. Soderholm, L. (2003). Mechanisms of Metal Ion Transfer into Room-Temperature Ionic Liquids the Role of Anion Exchange. /. Am. Chem. Soc., Vol.125, pp. 15466-15473 Kejun, L. Yen, W.T. Shibayama, A. Miyazaki, T. Fujita T. (2004). Gold Extraction from Thiosulfate Solution Using Trioctylmethylammonium Chloride. Hydrometallurgy, Vol. 73, pp. 41-53... 

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