Industrial solvents methyl isobutyl ketone

The commercial production of the industrial solvent methyl isobutyl ketone (MIBK) is based on metal impregnated polymeric resin (Scheme 11.7). 

Ketones are an important class of industrial chemicals that have found widespread use as solvents and chemical intermediates. Acetone (qv) is the simplest and most important ketone and finds ubiquitous use as a solvent. Higher members of the aUphatic methyl ketone series (eg, methyl ethyl ketone, methyl isobutyl ketone, and methyl amyl ketone) are also industrially significant solvents. Cyclohexanone is the most important cycHc ketone and is primarily used in the manufacture of y-caprolactam for nylon-6 (see Cyclohexanoland cyclohexanone). Other ketones find appHcation in fields as diverse as fragrance formulation and metals extraction. Although the industrially important ketones are reviewed herein, the laboratory preparation of ketones is covered elsewhere (1). 

Methyl Isobutyl Ketone. Methyl isobutyl ketone (MIBK) (4-methyl-2-pentanone), (CH2)2CHCH2COCH2, is an industrially important solvent which after methyl methacrylate and bisphenol A is the third largest tonnage product obtained from acetone. 

One of the most thoroughly investigated aldol condensations is the selfcondensation of acetone. This is an important industrial reaction for the production of diacetone alcohol (DA) (Scheme 11), which is valuable as a chloride-free solvent and an intermediate in the synthesis of industrially important products such as mesityl oxide (MO), isophorone, methyl isobutyl ketone, and 3,5-xylenol. The reaction is exothermic, with the yield of DA decreasing with increasing reaction temperature it is usually performed with NaOH or KOH as a basic catalyst 118). 

Major markets as solvents and intermediates have made the ketones important commercial products lor many years. Acetone and mcthylethyl ketone have had the most impact on the chemical industry Acetone Is used s an intermediate In methyl isobutyl ketone, methyl methacrylate, diucelonc alcohol. ketone. hisphenol-A. phiwnc. and mesityl oxide Acetone is largely produced by dehydration of isopropyl alcohol In the production of phenol from cumene, acetone is produced as a by-product This mute to acetone has tended to control its price. 

Solvent extraction has proved to be the most effective method for the separation of zirconium and hafnium, which invariably occur in nature in close association, owing to their almost identical chemical properties. These metals have found considerable use in the nuclear-power industry on account of their unusually high (hafnium) and low (zirconium) neutron-capture cross-sections. It is evident that the mutual separation of the two metals must be of a high degree to make them suitable for such applications. Two different solvent-extraction processes are known to be used on a commercial scale in one process, zirconium is selectively extracted from nitrate media into TBP in the second process, hafnium is selectively extracted from thiocyanate solutions into methyl isobutyl ketone (MIBK). 

Commonly used water-immiscible solvents in industrial-scale processes include alcohols (isobutanol, -butanol), ketones (particularly methyl isobutyl ketone), acetates (butyl, ethyl, isopropyl), hydrocarbons (toluene, hexanes), and methylene chloride. These solvents are inexpensive, readily available, and exhibit physical properties of low viscosity and density significantly different from water. Common water-miscible solvents are the alcohols (particularly methanol). For laboratory-scale processes, the selection is greater since selection is not constrained by economics. Craig and Sogn (16) have prepared an extensive compilation of such solvents. 

Simplicity, rapidity, and specificity have caused adoption of atomic absorption as a standard method in water analysis. Often solutions must be concentrated prior to measurement. Freezing, evaporation, ion exchange, and solvent extraction techniques have been reported. This paper describes a method for concentrating ferric iron, copper, zinc, cadmium, and lead using sodium diethyldithiocarbamate and methyl isobutyl ketone. Data shows increase in sensitivity caused by (1) concentrating effect of extraction, and (2) choice of the ketone solvent in preference to water. Recovery data on various industrial waters indicate that the method is reliable, reproducible, and accurate. 

The distribution of dissolved substances in two solvent phases is employed on a large scale in the industrial separation of mixtures of substances. Examples are the removal of unsaturated constituents from vegetable oils with furfurol or methanol, the purification of animal and vegetable oils with liquid propane, and the removal of waxes from lubricants with liquid propane or ketones. Penicillin is similarly concentrated with methyl isobutyl ketone, and aqueous glycerol is purified with xylene. Preparative and analytical separations are also performed by liquid-liquid extraction. Inorganic salts can be extracted from aqueous solutions with suitable solvents, such as ethers, ketones, and esters. This method is particularly efficient for metal halides and nitrates, e.g., the separation of uranium compounds from aqueous solutions or the fractional extraction of rare earths. 

Tables 14.25.1 and 14.25.2 provide data on the reported releases and transfers of solvents by the US rubber and plastics industry. These industries contribute small amounts of VOC which are in the range of0.00001-0.00005 kg VOC/kg of processed rubber. It was the ninth largest contributor to releases and transfers of all US industries. Dichloromethane, toluene, carbon disulfide, methyl ethyl ketone, methanol, 1,1,1-trichloroethane, hexane, methyl isobutyl ketone, and xylene are emitted in very large quantities.

MEK=methyl ethyl ketone, MIBK=methyl isobutyl ketone, EGBE=ethylene glycol monobutyl ether, AHC=aromatio hydrocarbon solvent Physical properties mainly from Industrial Solvents Handbook, 110 -114. Material Safety Data Sheet (Mobile Paint Co. Alabama)... 

Even though they are widely available as components of complex commercial products, thermosetting binders are difficult to obtain pure. For example, acrylic melamine formulations almost always contain mixtures of industrial solvents as diluents (such as 2-heptanone and -butanol), and they may also contain proprietary dispersing and wetting agents. Similarly, epoxy resin formulations commonly contain industrial xylene and/or methyl isobutyl ketone as diluents. 

Acetone and methyl ethyl ketone are components of solvent blends in urethane, nitrile rubber, and neoprene industrial adhesives. Acetone is the primary solvent in resin-type adhesives and pressure sensitive chlorinated rubber adhesives. Methyl isobutyl ketone is a solvent component for nitrile rubber and acrylic adhesives as well as in polyvinyl chloride and polyvinyl chloride-polyvinyl acetate copolymer bonding adhesives. Again, the desired evaporation rate of the adhesive formulation will often determine the ketone selected. 

Solvent use is controlled by both state and federal regulations. The federal Clean Air Act Amendments of 1990 mandate controls on solvent use in the industry. Almost all organic solvents are classified as VOCs under Title I of the 1990 Amendments and these regulations will require further reductions in future solvent use. Title III of the 1990 Amendments contains a long list of substances considered Hazardous Air Pollutants (HAPs). Some of the ketone solvents are on the HAP list. The solvents discussed in this chapter and that are on the HAP list include isophorone, methyl ethyl ketone, and methyl isobutyl ketone. The Maximum Achievable Control Technology (MACT) standards in the Title III section will become active during the late 1990s and... 

Solvent Extraction - Acetone is used to extract fats, oils, waxes, and resins from natural products, to dewax lubricating oils, and to extract certain essential oils. The pharmaceutical industry uses acetone to extract B-vitamin complexes, alkaloids, antibiotics and enzymes. Methyl ethyl ketone is used to dewax lube oil. Methyl isobutyl ketone is used to dewax mineral oil, refine tall oil, and in extractive distillation and separation of isopropyl alcohol from ethyl and butyl alcohols. The extraction and purification of antibiotics and other pharmaceutical products utilize MIBK. Methyl isobutyl ketone is used in the extraction of rosin from pine wood and the extraction of heavy metal ion complexes from water solutions. 

The dilution of crude oils and derivatives with organic solvents is an attractive sample preparation method, because it is simple and rapid and could be used for the determination of the metals by spectro-analytical techniques. The solvents commonly used are xylene, kerosene, methyl isobutyl ketone (MIBK), n-hexane, dimethylbenzene, 1-propanol and mixture of these solvents. The procedure is widely used in industry (Batho et al., 1993), (Botto and Zhu, 1996). Direct dilution of crude oils and residual fuels with an organic solvent for the determination of Ni, V, Fe and Na is proposed in ASTM standard test method (Standard test methods ASTM D 5863-00 a (2005). Ni and V in crudes and heavy crude fractions were determined after dilution in xylene (Fabec and Ruschak, 1985). The... 

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