Industrial quaternary amines

Glo-Sperse. [Global United Industries] Quaternary amine oxyalkylate dispos-ant, wetting agent, aitistat, emulsifier, ctXTOSion inhibitor. 

Antistatic agent can also be called antistat in the industry. The best antistatic agents used in fibre finishes are quaternary amines and alcohol phosphate esters. For example, A-cetyl-A-ethylmorpholinium ethylsulphate shown in Fig. 5.8a and stearyl alcohol phosphate shown in Fig. 5.8b are representative antistats. 

Polyelectrolytes are one of the most interesting and utiliz-able polymer materials presently under development. These water soluble polymers may be classified into three main groups nonionic polyelectrolytes, such as polyols, polyethers and polyamides anionic polyelectrolytes, such as carboxylates, sulfonates, and phosphates and cationic polyelectrolytes, such as ammonium, quaternary amines, sulfoniums and phosphoniums (1). These materials have wide and varied industrial applications. 

Organoclays are the most widely used inorganic thickeners in the paint and coating industry. They are derived by modification of naturally occurring laminar silicates (clays) such as hectorite and bentonite. They have replaceable cations (Na Ca" or Lk) on the surface of the crystal that are replaced, through an ion exchange reaction, by organic quaternary ammonium cations such as [dimethyldioctadecylammo-nium] or [dimethylbenzyloctadecylammonium]. Occasionally a blend of quaternary amines is used to tailor the properties of the product. 

The majority of polymers used in industrial coatings are of the carboxyl functional type and when neutralised, they produce a quaternary amine or ammonium salt of the polymer which is water reducible, as shown in Figure 7-6. 

Although anionics and nonionics may be used in industrial applications, all products destined for domestic applications have a cationic surfactant as the active agent. Fabric softeners are sold as dispersions, to be added to the rinse water, or in dry form carried on nonwoven sheets, for use in the dryer. The most common active agent for both applications is a quaternary amine salt with high alkyl character and low water solubility, such as the chloride or methyl sulfate salt of ditallowdimethylammonium ion. 

Companies producing fatty amine quaternaries include Akzo Chemicals Inc. (Arquad) (73) Henkel Corporation (formerly General Mills) (Aliquat) (74) Humko Chemical (Witco Corporation) (Kemamine Q) (31) Jetco Chemicals (The Procter Gamble Company) (fet Quat) (75) Jordan Chemical Company (PPG Industries) (fordaquat and specialty quaternaries) (78) Lonza (Barquat and specialty quaternaries) (79) Sherex (Adogen) (76) and Tomah Products (Exxon Chemical Company) (Tomah Q) (77). 

Nearly all uses and appHcations of benzyl chloride are related to reactions of the active haUde substituent. More than two-thirds of benzyl chloride produced is used in the manufacture of benzyl butyl-phthalate, a plasticizer used extensively in vinyl flooring and other flexible poly(vinyl chloride) uses such as food packaging. Other significant uses are the manufacture of benzyl alcohol [100-51-6] and of benzyl chloride-derived quaternary ammonium compounds, each of which consumes more than 10% of the benzyl chloride produced. Smaller volume uses include the manufacture of benzyl cyanide [140-29-4], benzyl esters such as benzyl acetate [140-11-4], butyrate, cinnamate, and saUcylate, benzylamine [100-46-9], and benzyl dimethyl amine [103-83-8], and -benzylphenol [101-53-1]. In the dye industry benzyl chloride is used as an intermediate in the manufacture of triphenylmethane dyes (qv). First generation derivatives of benzyl chloride are processed further to pharmaceutical, perfume, and flavor products. 

The alkyl halide (ethyl bromide in the above equation) can react further with the primary amine produced to give a secondary amine and with that to form a tertiary amine and finally a quaternary ammonium salt. Quaternary ammonium hydroxides are very strong bases like sodium hydroxide. Tetramethylammonium hydroxide is a very important chemical used in the manufacture of semiconductors and other electronic industry products. 

Four types of organic amines exist, as shown in Table 4.8 primary amines RNHj, secondary R2NH2, tertiary RsNH, and quaternary R4N (Appendix D). The hydrocarbon chain R is usually of length Cg-Cu, commonly a straight aliphatic chain, but branched chains and aromatic parts also occur. In general the amines extract metal complexes in the order tertiary > secondary > primary. Only long-chain tertiary and—to a smaller extent—quarternary amines are used in industrial extraction, because of their suitable physical properties trioctylam-ine (TOA, 8 carbons per chain) and trilauryl amine (TLA, 12 carbons per chain) are the most frequently used. For simplicity we abbreviate all amines by RN, and their salts by RNH L . 

Industrial surfactants find uses in almost every industry, from asphalt manufacturing to carpet fibers, from pulp and paper production to leather processing. Examples of the types of chemicals used as surfactants are fatty alcohol sulfates, alkanolamides, alkoxylates, sulfosuccinates, amines, quaternaries, phosphate esters, acid esters, blockcopolymers, betaines, imidazolines, alkyl sulfonates, etc. 

The industrial development of silica sol manufacturing methods is reviewed. Primary attention is focused on the preparation of monodispersed sols from water glass by the ion-exchange method. Details are given for variations of manufacturing process and for the characteristics of both the processes and sols obtained. Furthermore, the following surface modifications of particles are demonstrated silica sols stabilized with ammonia, amine, and quaternary ammonium hydroxide aluminum-modified or cation-coated silica sol and lithium silicate. Finally, future trends in silica sol manufacturing are discussed from the viewpoint of not only raw materials and improvement of the procedures but also the function of the silica sols and their particle shape. 

Figure 25 shows a specific example of extraction of furfural using a hydrocarbon solvent. Sharma (1988) has considered several other examples of reactions which would profit from introduction of an additional phase. Sharma (1988) has also provided several examples of liquid-liquid reactions of industrial interest which could benefit from the addition of substances such as quaternary ammonium and phosphonium salts, crown ethers and trialkyl amines, which function as phase transfer catalysts, significantly enhancing the reaction rates and in some cases improving the reaction selectivity. 

Genamin. [Hoechst Celanese/Colcxants Surf. Hoechst AG] Amines, ethoxylated amines, or quaternaries base material, emulsifier, conditioner for hair care and industrial prods. 

SPILL CLEAN-UP use water spray to "knock down" dust use solvent extraction with high molecular-weight amines and quaternary ammonium compounds for the removal or arsenic from industrial effluents. 

Analytical methods include thin-layer chromatography (69), gas chromatography (70), and specific methods for determining amine oxides in detergents (71) and foods (72). Nuclear magnetic resonance (73—75) and mass spectrometry (76) have also been used. A frequendy used procedure for industrial amine oxides (77) involves titration with hydrochloric acid before and after conversion of the amine to the quaternary ammonium salt by reaction with methyl iodide. A simple, rapid quaUty control procedure has been developed for the determination of amine oxide and unreacted tertiary amine (78). 

Most unsaturated ring quats of industrial importance are alkylpyridinium halides (I) and substituted imidazolinium compounds (11). To prepare alkylpyridinium halide, pyridine is reacted with the equimolar amounts of alkyl halide for several hours at 100-150 °C without solvent according the reactions given above. The reaction is two orders slower in this case because the basicity of pyridine is much weaker in comparison with aliphatic tertiary amines and heterocyclic aliphatic amines, such as N-alkylpiperidine and N-alkylmorpholine, too. Typical examples of the aromatic quaternaries are given below ... 

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