Lipase-catalyzed synthesis of a pure macrocyclic polyester from dimethyl terephthalate and diethylene glycol.
The polymerization of dimethyl terephthalate and diethylene glycol by enzymic catalysis in toluene is described. The potential pi-pi interactions of the aromatic rings together with the relative flexibility of the diol segment have been regarded as synergy factors responsible for the formation of a pure cyclic compound. The so-called C2 macrocycle was characterized by (1)H and (13)C NMR, size-exclusion chromatography, differential scanning calorimetry, mass spectrometry, and X-ray diffraction on powder. Structurally speaking, it is made of two repeating units. The substitution of the central oxygen atom of the diol by -CH(2)- or -S- as well as the presence of ortho-substituents (-NH(2) or -NO(2)) on the phthalate were expected to disrupt the stacking of the phenyl groups more or less.
Lavalette
Arnaud
A
Laboratoire de Synthèse Macromoléculaire UMR 7610 "Chimie des Polymères", Université Pierre et Marie Curie, 4 place Jussieu, Case 184, F-75252 Paris cedex 05, France.
Lalot
Thierry
T
Brigodiot
Maryvonne
M
Maréchal
Ernest
E
D002384:Catalysis; D005026:Ethylene Glycols / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010795:Phthalic Acids / Q000737:chemistry*; D011091:Polyesters / Q000138:chemical synthesis*; D013696:Temperature; D014050:Toluene
D005026:Ethylene Glycols; D010795:Phthalic Acids; D011091:Polyesters; D014050:Toluene; C013484:diethylene glycol; D008049:Lipase; C004782:dimethyl 4-phthalate