Ammonium salts quaternary

Tetraethylammonium chloride is insoluble in liquid phosgene, whilst tetrabutylammonium chloride undergoes solvolysis, possibly releasing an amine [1012]. 

The quaternary ammonium group is not hydrolysed by acids, but ester or amide groups in the alkyl chain may be hydrolysed. 

Alkali. Conversion to olefin and tertiary amine or pyridine takes place. 

There are, however, apparently no reports in the literature of the use of this hydrolysis for analytical purposes. 

Dialkyldimethylammonium salts of the type R2N+(CH3)2C1 and imidazolinium salts of structure 

At present, triethanolamine ester quats (TEAEQ), with a formal structure of (RC02CH2CH2)2N+(CH3)CH2CH2OH-CH3SC 4 are the fabric softeners of choice in Europe and elsewhere, replacing the imidazolinium and dialkyldimethyl ammonium types. 

Hoffmann, C. E. (1972) In Herbicides, Fungicides, Formulation Chemistry Proc. lUPAC 2ndInternat. 

Kecskes, M., Gombos., Horvith, L. and Pozsar, B. (1974) lUPAC, Third Internal. Congr. Pestic. 

Meeklah, F. A. and McRobb, H. (1973) Proc. 26th New Zealand Weed and Pest. Control Conf.. 26,65. Moreland. D. E. (1967) Ann. Rev. Plant Physiol, 18, 365. 

It has been known for some time that one group of surfactants, the quaternary ammonium compounds, are more phytotoxic than the anionic and nonionic types. 

The field of research was then extended to nontensioactive quaternary ammonium compounds, and in the reaction product of 2,2-bipyridyl, prepared for other purposes, with ethylene bromide a herbicide (diquat, 1) was discovered which proved efficient in greenhouses at a rate of 125 g/ha (Brian et at.. 1958). This compound was followed by paraquat (2) (Jeater, 1963) and other isomeric bipyridyls and their substituted derivatives. 

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Girard s reagents Quaternary ammonium salts of the type Me3NCH2CONHNH2 X which form water-soluble compounds with aldehydes and ketones, and are therefore separable from other neutral compounds the aldehyde or ketone may be subsequently regenerated after separation. 

Girard s reagent T is carbohydrazidomethyltrimethylammonium chloride (I) and is prepared by the reaction of the quaternary ammonium salt formed from ethyl chloroacetate and trimethylamine with hydrazine hydrate in alco-hoUc solution ... 

Amines are powerful nucleophiles which react under neutral or slightly basic conditions with several electron-accepting carbon reagents. The reaction of alkyl halides with amines is useful for the preparation of tertiary amines or quaternary ammonium salts. The conversion of primary amines into secondary amines is usually not feasible since the secondary amine tends towards further alkylation. 

Allylic amine is a less reactive leaving group[7], but the allylic ammonium salts 214 (quaternary ammonium salts) can be used for allylalion(l30,131]. Allylic sulfonium salts are also used for the allylation[130]. The allylic nitrile in the cyclic aminonitrile 215 can be displaced probably via x-allylic complex formation. The possibility of the formation of the dihydropyridinium salts 216 and subsequent conjugate addition are less likelyfl 32],... 

Benzyltnmethyl ammonium iodide (a quaternary ammonium salt)... 

Ammonium salts that have four alkyl groups bonded to nitrogen are called quaternary ammonium salts... 

In spite of being ionic many quaternary ammonium salts dissolve m nonpolar media The four alkyl groups attached to nitrogen shield its positive charge and impart lipophilic character to the tetraalkylammonium ion The following two quaternary ammonium salts for example are soluble m solvents of low polarity such as benzene decane and halo genated hydrocarbons... 

This property of quaternary ammonium salts is used to advantage m an experi mental technique known as phase transfer catalysis Imagine that you wish to carry out the reaction... 

Sodium cyanide does not dissolve m butyl bromide The two reactants contact each other only at the surface of the solid sodium cyanide and the rate of reaction under these con ditions IS too slow to be of synthetic value Dissolving the sodium cyanide m water is of little help because butyl bromide is not soluble m water and reaction can occur only at the interface between the two phases Adding a small amount of benzyltrimethyl ammonium chlonde however causes pentanemtnle to form rapidly even at room temper ature The quaternary ammonium salt is acting as a catalyst it increases the reaction rate How7... 

Quaternary ammonium salts catalyze the reaction between an anion and an organic substrate by transfemng the anion from the aqueous phase where it cannot contact the substrate to the organic phase In the example just cited the first step occurs m the... 

Even the tertiary amine competes with ammonia for the alkylating agent The product is a quaternary ammonium salt... 

Because of its high reactivity toward nucleophilic substitution methyl iodide is the alkyl halide most often used to prepare quaternary ammonium salts... 

Quaternary ammonium salts as we have seen are useful m synthetic organic chem istry as phase transfer catalysts In another more direct application quaternary ammo mum hydroxides are used as substrates m an elimination reaction to form alkenes... 

Quaternary ammonium salts compounds of the type R4N" X find application m a technique called phase transfer catalysis A small amount of a quaternary ammonium salt promotes the transfer of an anion from aqueous solution where it is highly solvated to an organic solvent where it is much less solvated and much more reactive... 

Ammonia can act as a nucleophile toward primary and some secondary alkyl halides to give primary alkylamines Yields tend to be modest because the primary amine IS itself a nucleophile and undergoes alkylation Alkylation of ammonia can lead to a mixture containing a primary amine a secondary amine a tertiary amine and a quaternary ammonium salt... 

Alkylation (Section 22 12) Amines act as nucleophiles toward alkyl halides Pri mary amines yield secondary amines secondary amines yield tertiary amines and tertiary amines yield quaternary ammonium salts... 

Physostigmme an alkaloid obtained from a West African plant is used in the treatment of glaucoma Treatment of physostigmme with methyl iodide gives a quaternary ammonium salt What IS the structure of this salt" ... 

Quantum (Section 13 1) The energy associated with a photon Quaternary ammonium salt (Section 22 1) Salt of the type R4N X The positively charged ion contains a nitrogen with a total of four organic substituents (any combination of alkyl and aryl groups)... 

A typical composition of the catholyte is adiponitrile, 15 wt % acrylonitrile, 15 wt % quaternary ammonium salt, 39 wt % water, 29 wt % and by-products, 2 wt %. Such a solution is extracted with acrylonitrile and water, which separates the organics from the salt that can be returned to the cell. 

The reactions are catalyzed by tertiary amines, quaternary ammonium salts, metal salts, and basic ion-exchange resins. The products are difficult to purify and generally contain low concentrations of acryhc acid and some diester which should be kept to a minimum since its presence leads to product instabihty and to polymer cross-linking. 

Halex rates can also be increased by phase-transfer catalysts (PTC) with widely varying stmctures quaternary ammonium salts (51—53) 18-crown-6-ether (54) pytidinium salts (55) quaternary phosphonium salts (56) and poly(ethylene glycol)s (57). Catalytic quantities of cesium duoride also enhance Halex reactions (58). 

Medicated Dandruff Shampoos. Dandmff is a scalp condition characterized by the production of excessive cellular material (18). A number of shampoos have been marketed which are designed to control and alleviate this condition, and many additives have been included in shampoo compositions to classify them as treatment products for dandmff. These additives include antimicrobial additives, eg, quaternary ammonium salts keratolytic agents, eg, saUcychc acid and sulfur heavy metals, eg, cadmium sulfide coal tar resorcinol and many others. More recent (ca 1993) systems use selenium sulfide [7488-56-4] or zinc pyrithione [13463-41 -7] as active antidandmff shampoo additives. Both of these additives are classified as dmgs, but can be found in over-the-counter products. A stronger version, incorporating the use of higher levels of selenium sulfide in a shampoo, is available but requires a prescription for purchase. 

Basic Extractants. Only long-chain quaternary ammonium salts, R3NCH3 X , ia which R represents Cg—0 2 groups and X nitrate or thiocyanate, are effectively used for REE separations (see Quaternary ammonium compounds). The extractant reacts with REE according to an anion-exchange reaction ... 

Solids present in oil and synthetic muds must be kept wet with the nonaqueous phase to prevent coagulation and settling and mud instabiUty. Oil-wetting agents are normally incorporated in the basic mud package. These materials are typically amines or quaternary ammonium salts having hydrocarbon chains of 10 or more carbon atoms. They also render clays or lignites oil-wet for use in viscosity and filtration control (128). 

Both in situ cross-linking of partially hydroly2ed polyacrylamides (69) and injection of quaternary ammonium salt polymers having long hydrophilic side chains (70) have been used to reduce the permeabiUty of water-producing 2ones adjacent to production wells. This permeabiUty reduction decreases the produced water oil ratio as does injection of polyacrylamide in high hardness brine to reduce permeabiUty (71). 

The substantial decrease of polyacrylamide solution viscosity in mildly saline waters can be uti1i2ed to increase injection rates. A quaternary ammonium salt polymer can be added to the polyacrylamide solution to function as a salt and reduce solution viscosity (144). If the cationic charge is in the polymer backbone and substantially shielded from the polyacrylamide by steric hindrance, formation of an insoluble interpolymer complex can be delayed long enough to complete polyacrylamide injection. Upon contacting formation surfaces, the quaternary ammonium salt polymer is adsorbed reducing... 

The action of redox metal promoters with MEKP appears to be highly specific. Cobalt salts appear to be a unique component of commercial redox systems, although vanadium appears to provide similar activity with MEKP. Cobalt activity can be supplemented by potassium and 2inc naphthenates in systems requiring low cured resin color lithium and lead naphthenates also act in a similar role. Quaternary ammonium salts (14) and tertiary amines accelerate the reaction rate of redox catalyst systems. The tertiary amines form beneficial complexes with the cobalt promoters, faciUtating the transition to the lower oxidation state. Copper naphthenate exerts a unique influence over cure rate in redox systems and is used widely to delay cure and reduce exotherm development during the cross-linking reaction. 

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