Some patterns of the synthesis of aromatic polyketones by precipitative polycondensation

Zolotukhin, Mikhail G.; Gileva, N. G.; Салазкин, С. Н.; Sangalov, Yu. A.; Genin, Ya.V.; Sultanova, V. S.

doi:10.1016/0032-3950(89)90307-9

Cited by 6 publications

(7 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In general, the Friedel–Crafts polymerization is carried out in chlorinated hydrocarbons such as DCE with excess AlCl 3 to diacid chlorides because of formation of 1:1 complex of carbonyl group of acid chloride and AlCl 3 . , When TPC and IPC were used as diacid chlorides, the optimum f c was reported to be 2.7–2.9. − In the polymerization, AlCl 3 was added to the monomer solution below 0 °C. Thereafter, the polymerization temperature was raised to 20 °C and the polymerization was performed at 20 °C for ca.…”

Section: Resultsmentioning

confidence: 99%

“…Preparations of PEKs are classified into two reactions. One is the aromatic nucleophilic substitution polymerization between activated aromatic dihalides and alkali metal phenoxides to form the ether linkage. , Another is the aromatic electrophilic substitution polymerization, so-called Friedel–Crafts polymerization, between aromatic diacid chlorides and electron-rich aromatic hydrocarbons to form the ketone linkages. − The latter polymerizations are generally carried out in organic solvents with a catalyst of aluminum chloride (AlCl 3 ) or iron(+III) chloride under moderate conditions. Hence, the Friedel–Crafts polymerization is more suitable to use FDCA as a monomer.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Preparation of Poly(ether ketone)s Derived from 2,5-Furandicarboxylic Acid by Polymerization in Ionic Liquid

2016

View full text Add to dashboard Cite

Aromatic poly(ether ketone)s were synthesized by the Friedel−Crafts polymerization of 2,5-furandicarbonyl dichloride prepared from biomass and petroleum-based aromatic ethers such as diphenyl ether and 1,4-diphenoxybenzene with aluminum chloride (AlCl 3 ). The polymerizations in common molecular solvents such as 1,2-dichloroethane and nitrobenzene did not afford polymers. The Friedel−Crafts polymerization usually undergoes in the swollen gel of the oligomer−AlCl 3 complexes; the precipitated physical gels had not been enough swollen. The polymerizations were carried out in various ionic liquids to form swollen gels. The polymerizations proceeded in specific ionic liquid such as 1-butyl-3-methylimidazolium chloride ([C 4 mim]Cl), and high molecular weight polymers were obtained with good yield. The gels formed in [C 4 mim]Cl were more highly swollen, and additionally the rate constant estimated by the model reaction of 2,5furandicarbonyl dichloride and anisole was higher in [C 4 mim]Cl than that in 1,2-dichloroethane. The obtained poly(ether ketone)s exhibited good thermal stability and chemical resistance comparable to common poly(ether ketone)s.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Preparation of Poly(ether ketone)s Derived from 2,5-Furandicarboxylic Acid by Polymerization in Ionic Liquid

2016

View full text Add to dashboard Cite

show abstract

“…In general, the Friedel-Crafts polymerization is carried out in chlorinated hydrocarbons such as DCE with excess AlCl 3 to diacid chlorides because 1:1 complex of carbonyl group of acid chloride and AlCl 3 is formed [5,6]. When typical diacid dichlorides such as terephthaloyl chloride were used, the optimum f a was reported to be 2.6-2.9 [7][8][9][10]. Th-PEK had been previously synthesized by the Friedel−Crafts polymerization of TDCC and DPE [10].…”

Section: Polymerizationsmentioning

confidence: 99%

Synthesis of Poly(ether ketone)s from 2,5-Thiophenedicarboxylic Acid

Kanetaka

Yamazaki

Kimura

2016

J. Photopol. Sci. Technol.

View full text Add to dashboard Cite

“…Preparations of PEKs are classified into two methods; the aromatic nucleophilic substitution and the aromatic electrophilic substitution, so-called Friedel-Crafts acylation catalyzed by aluminum trichloride (AlCl 3 ) [1]. In the latter case, the reaction gives a precipitate of the complex of oligomer and catalyst in the course of polymerization [2][3][4][5][6]. It has been revealed that even though the oligomer is precipitated, the molecular weight of PEK increases with reaction time in the precipitates formed in 1,2-dichloroethane (DCE) [3,5,7].…”

Section: Introductionmentioning

confidence: 99%

Consideration of Solvent Effect on Precipitation Polymerization of Poly(ether-ketone)s via Friedel-Craft Acylation

et al. 2006

View full text Add to dashboard Cite

Precipitation polymerization of diphenyl ether and isophthaloyl chloride catalyzed by AlCl 3 via Friedel-Crafts acylation was examined in various solvents to clarify the polymerization behavior. Polymerizations were carried out in three categorized solvents based on the solubility to both catalyst and polymer, which were cyclohexane (CH), 1,2-dichloroethane (DCE) and DCE containing 2 wt% nitrobenzene (2%-NB). In DCE which was widely used, the oligomers were precipitated as a form of the complex with AlCl 3 at the early stage of polymerization. The precipitates of the oligomers were swollen by the solvent, in which any short-range regular structure did not exist. The further polymerization proceeded even in the precipitates with eliminating by-produced HCl, and high molecular weight poly(ether-ketone)s (PEK) were finally formed. Nevertheless the reaction in 2%-NB yielded the well-swollen precipitates, the high molecular weight PEK was not synthesized in the precipitates because the reaction was terminated by not only the inefficient elimination of HCl due to the higher solubility of HCl but also the deactivation of catalyst by coordination of NB to AlCl 3 . Although the precipitation occurred more readily in CH due to the lower solubility of oligomers, the polymer was not synthesized in the precipitates. The resulting precipitates comprised of the dimers were not swollen in this case, and thereby it was very difficult to react between dimers and eliminate HCl from the precipitates. The solvents having high miscibility to catalyst and the polymers, low solubility of HCl gas, and no basicity are necessary for making high molecular weight polymers via the precipitation polymerization.

show abstract

Some patterns of the synthesis of aromatic polyketones by precipitative polycondensation

Cited by 6 publications

References 3 publications

Preparation of Poly(ether ketone)s Derived from 2,5-Furandicarboxylic Acid by Polymerization in Ionic Liquid

Preparation of Poly(ether ketone)s Derived from 2,5-Furandicarboxylic Acid by Polymerization in Ionic Liquid

Synthesis of Poly(ether ketone)s from 2,5-Thiophenedicarboxylic Acid

Consideration of Solvent Effect on Precipitation Polymerization of Poly(ether-ketone)s via Friedel-Craft Acylation

Contact Info

Product

Resources

About