Plasticizer 2-ethylhexanol-based

Other 2-ethylhexanol based plasticizers include di-2-ethylhexyl adipate for vinyl food wrap application, tri-2-ethylhexyl trimellitate, di-2-ethylhexyl azelate, and di-2-ethylhexyl sebacate. 

Other 2-ethylhexanol based plasticizers were introduced, including some which imparted outstanding low temperature flexibility—dioctyl adipate (DOA), dioctyl azelate (DOZ), dioctyl sebacate (DOS), and trioctyl phosphate (TOF). In addition, TOF showed high resistance to microorganisms which was important in military applications. Furthermore, TOF improved flame resistance. However, the mixed ester—octyl diphenyl phosphate—also introduced in the forties—was far superior and showed a better balance of low temperature performance and flame resistance than either TOF or the well-established plasticizer—tricresyl phosphate (TCP). Each of these found a market as a specialty plasticizer because of these specific performance attributes. None, however, was a serious threat to DOP on an overall price-performance basis. Rather, they were used to supplement the properties of DOP where its performance was inadequate. 

Ethyl alcohol has been made by the hydration of ethylene (9) since 1930. Like isopropyl alcohol, part of the output is used as a solvent, but most is converted to other oxygenated chemicals. Its most important raw material use is conversion to acetaldehyde by catalytic air oxidation. Acetaldehyde, in turn, is the raw material source of acetic acid, acetic anhydride, pentaerythritol, synthetic n-butyl alcohol (via aldol condensation), butyraldehyde, and other products. Butyraldehyde is the source of butyric acid, polyvinyl butyral resin, and 2-ethylhexanol (octyl alcohol). The last-named eight-carbon alcohol is based on the aldol condensation of butyraldehyde and is used to make the important plasticizer di-2-ethylhexyl phthalate. A few examples of the important reactions of acetaldehyde are as follows ... 

Shutdown of Oxochem s 2-ethylhexanol unit in 1978 eliminated 300 million pounds of capacity overnight. As a result, DOP users began a crash reformulation effort on alternative plasticizers. Linear alcohol and Cg and Ciq branched chain alcohol based phthalates as well as butyl benzyl phthalate, for example, were found to be wholly or partially substitutable plasticizers in many DOP applications. New 2-ethylhexanol capacity available starting in 1981 is expected... 

Meanwhile, Rohm and Haas introduced the first of the polymeries - polyesters based on the reaction of a dibasic acid with a glycol and with a monohydric alcohol or monobasic acid as chain terminator(j>). These plasticizers were developed as highly permanent, extraction and migration resistant types for specialty applications. 2-Ethylhexanol and isodecyl alcohol are examples of monohydric alcohols used as chain terminators in today s polymeries. 

As for condensation reactions. King ei al. [1 discussed on the search for solid base catalysts suitable for industrial aldol condensation of aldehydes (n-butanal and n-hexanal. mainly). Moreover, the authors made emphasis on the industrial importance of such processes to obtain a number of key compounds such as 2-ethylhexanol (which can be converted into dimethylhexylphtalate. a plasticizer for PVX ), methyl isobutyl-kctone (MIPK. an excellent solvent for cellulose and resin-based Ci>atings) or Ouerbet alcohols, used in cosmetics, textiles, lubricants and surfactants. In any case, condensation reactions will be more extensively discussed on the following section, devoted to Fine Chemistry. 

Monobenzoate esters are prepared by the esterification of benzoic acid with one molar equivalent of alcohol, usually 2-ethylhexanol, isononanol, or isodecanol. Monobenzoates are not used as primary plasticizers but as secondary plasticizers where they help reduce plastisol viscosities, lower the fusion or processing temperatures, and give a boost to stain resistance in formulations based on GP plasticizers. Both mono and dibenzoate esters can be used in non-PVC materials such as acrylic films and caulks, latex coatings, polysulfide sealants and coatings, and polyurethanes. 

Acetaldehyde is aldolized and hydrogenated into 2-ethylhexanol to make synthetic ester plasticizers for rubber compounds based on specialty elastomers. These plasticizers include DOP, DOA, and DOS. 

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