Diphenyl adipate

This structure was conclusively established by carboxylation of the dimer which produced a mixture of stereoisomers of 2-5-dimethyl-2,5-diphenyl-adipic acids (19). 

A soln. of e s-/3,//-diphenyl-a,a,-dihydromueonic acid in 10%-NaOH warmed on a steam bath, treated with small portions of Ni-Al, and worked up after a further hr. <5n the steam bath —>- meso-, //-diphenyl-adipic acid. Y almost 100%.—In the same manner, the trans-acid is reduced to the corresponding D,L-acid. (F. e. s. G. M. Badger, Soc. 1948, 999.)... 

PVB resins are also compatible with a limited number of plasticizers and resins. Plasticizers (qv) improve processibility, lower T, and increase flexibihty and resiUency over a broad temperature range. Usehil plasticizers include dibutyl and butyl benzyl phthalates, tricresyl and 2-ethylhexyl diphenyl phosphates, butyl ricinoleate, dibutyl sebacate, dihexyl adipate, triethylene glycol di-2-ethylbutyrate, tetraethylene glycol diheptanoate, castor oil, and others (64-73). 

On the other hand, Davies5 , studying the reaction of adipic add with 1,5-pentanediol in diphenyl oxide or diethylaniline found an order increasing slowly from two with conversion. From this result he concluded that Flory s1,252-254> and Hinshelwood s240,241 interpretations are erroneous. Two remarks must be made about the works of Davies5 experimental errors relative to titrations are rather high and kinetic laws are established for conversions below 50%. Under such conditions the accuracy of experimental determinations of orders is rather poor. 

PBX-9011-02 HMX 90 Sc Estane (Trademark of B.F, Goodrich Chemical Co for polyester urethane of adipic acid 1,4-butanediol, diphenyl methane diisocyanate) 10%... 

Abbreviations PTMA poly(tetramethylene adipate) PEA poly(ethylene adipate) MDI diphenyl-methane diisocyanate BD butane diol PAN polyacrylonitrile Ar polyarylate OBU oligobutadiene-urethane... 

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. 

Various organic plasticizers having boiling points over 300 °C are available, such as di(2-ethylhexyl) phthalate (4a), di(2-ethylhexyl) adipate (8), oligomers formed from dicarboxylic acids and diols with molecular weights ranging up to 3500, esters of tri-mellitic acid, epoxidised fatty acids or organic phosphates, such as tris(2-ethylhexyl) phosphate (9) or (2-ethylhexyl) diphenyl phosphate (10). Most phosphates also function as flame retardants and some, such as 10, are smoke suppressants as well (Meier, 1990). 

Diphenyl carbonate from dimethyl carbonate and phenol Dibutyl phthalate from butanol and phthalic acid Ethyl acetate from ethanol and butyl acetate Recovery of acetic acid and methanol from methyl acetate by-product of vinyl acetate production Nylon 6,6 prepolymer from adipic acid and hexamethylenediamine MTBE from isobutene and methanol TAME from pentenes and methanol Separation of close boiling 3- and 4-picoline by complexation with organic acids Separation of close-boiling meta and para xylenes by formation of tert-butyl meta-xyxlene Cumene from propylene and benzene General process for the alkylation of aromatics with olefins Production of specific higher and lower alkenes from butenes... 

Taking DOP as the reference standard of performance for low-temperature flex efficiency, other commercial plasticizers that are significantly better performers include linear dialkyl phthalates and alkyl esters of sebacic, azelaic, adipic, phosphoric, and epoxidized oleic acids. Significantly poorer performers are tricresyl phosphate, diphenyl phthalate, butyl benzyl phthalate, and branched dialkyl phthalates. 

An alternative interpretation of this polymerization was advocated by Schlenk and Bergmann8. In his early work reported in 19149 Schlenk described the addition of alkali metals to aromatic hydrocarbons leading to intensely colored solutions. The concepts of free radicals or radical-ions were unknown at that time, hence Schlenk referred to the adduct as a complex. He also showed that a similar reaction of 1,1-diphenyl ethylene resulted in its colored dimer which yielded 2,2,5,5-tetraphenyl adipic add on carboxyla-tion. When the concept of free radicals was established, Schlenk and Bergmann argued that the initially formed adduct is a free radical, e.g. 

In many cases the crude acid chloride can be used for further reactions. For instance, a mixture of adipic acid (1 mole) and SOCl2 (3 moles) is warmed at 50-60° until evolution of HC1 and S02 ceases (4 h) and the excess of SOCl2 is distilled off in a vacuum the resulting crude adipoyl chloride can be used for preparation of l,6-diphenyl-l,6-hexanedione.1107... 

DIDA diisodecyl adipate DPCF diphenyl cresyl phosphate... 

Admex 409 Admex 6996 Isodecyl diphenyl phosphate Polyester adipate, Santicizer 148 Santicizer 261 Tehabromobis (2-ethyttexyl) phthalate, Uniplex FRP-45... 

Butyl acetyl ricinoleate, Dt (C7S alkyl) adipate Plasthall P-7046 Plasthall P-7092 Santicizer 97 plasticizer, NBR elastomers Isodecyl diphenyl phosphate, Phosflex 390... 

Albrite TBP Antiblaze 519 Diisobutyi phthaiate, Diisodecyi phthaiate Diisoheptyi phthaiate, Diisononyi adipate Diisononyi phthalate. Dioctyl sebacate Dioctyl terephthalate. Diphenyl octyl phosphate, Dlpropylene glycol dibenzoate, DIstearyl thiodipropionate Drakeol 9 Drakeol 34 Ethyl toluenesulfonamide Isobutyl stearate Isodecyl diphenyl phosphate,... 

Santheose. See Theobromine Santicizer 8. See Ethyl toluenesulfonamide Santicizei 97. See Di (C7-9 alkyl) adipate Santicizer 141. See Diphenyl octyl phosphate Santicizer 148-DLD. See Isodecyl diphenyl phosphate... 

Diisobutyl sodium sulfosuccinate Dimethicone copolyol acetate Dimethicone copolyol adipate Dioleyl tocopheryl methylsilanol Diphenyl dimethicone... 

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