The Effect of the Impurities in Refinery Process from Fermentation Broth on Lactic Acid Polymerization

Achmad, Feerzet; Yamanishi, Keisuke; Liu, Zhi Yuan; Kokugan, Takao

doi:10.1252/jcej.09we101

Cited by 5 publications

(11 citation statements)

References 11 publications

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“…The detection and removal of impurities is essential because they can strongly deteriorate the properties of the produced polymer. 11 Lactide, the ring-formed dimer of lactic acid, is used in the production of high molar mass PLA in the ring-opening polymerization (ROP) route and is therefore an important intermediate in the industrial production of PLA. Because of the chiral nature of lactic acid, lactide exists in three different forms: L,L-lactide, D, D-lactide, and D,L-lactide.…”

Section: ' Introductionmentioning

confidence: 99%

“…The available information about the specific effects of impurities in lactic acid solutions on the polymerization processes of PLA is scarce. 11 It is reported that the total amount of impurities in lactic acid should preferably be <0.05 mol % before step-growth polymerization. 12 In case they are not completely removed in the downstream processing stage, impurities such as butanol and butyl lactate can act as external catalysts in the step-growth polymerization of PLA and also affect the thermal degradation characteristics of the produced polymer.…”

Section: ' Introductionmentioning

confidence: 99%

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From Lactic Acid to Poly(lactic acid) (PLA): Characterization and Analysis of PLA and Its Precursors

et al. 2011

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The quality of the monomers lactic acid and lactide as well as the chemical changes induced during polymerization and processing are crucial parameters for controlling the properties of the resulting poly(lactic acid) (PLA) products. This review presents the most important analysis and characterization methods for quality assessment of PLA and its precursors. The impurities typically present in lactic acid or lactide monomers and their possible origins and effects on resulting PLA products are discussed. The significance of the analyses for the different polymer production stages is considered, and special applications of the methods for studying features specific for PLA-based materials are highlighted.

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Section: ' Introductionmentioning

confidence: 99%

Section: ' Introductionmentioning

confidence: 99%

From Lactic Acid to Poly(lactic acid) (PLA): Characterization and Analysis of PLA and Its Precursors

et al. 2011

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“…15 Infrared spectroscopy has been applied to analysis of impurities generated from fermentation process. 16 Li et al studied clustering of lactic acid using mass-analyzed ion kinetic-energy spectrometry (MIKES) and analyzed cluster ions of dimer to tetramer and their mono-dehydrated molecules, and they reported that there was no OLA in commercial lactic acid. 17 In atmospheric pressure chemical ionization-mass spectrometer (APCI-MS), an analyte solution is nebulized and evaporated through the heating zone that usually keeps high temperature of above 300 C for efficient evaporation.…”

Section: Introductionmentioning

confidence: 99%

Complex formation of lactic acid by atmospheric pressure chemical ionization

Son

Choi

2022

J Mass Spectrom

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Oligomers and polymers of lactic acid are generally synthesized through condensation reactions by dehydration at high emperature under catalysis. In the present work, ionization behaviors of lactic acid produced by atmospheric pressure chemical ionization were investigated. Influence of the sample concentration, the heating zone temperature, and the source fragmentor voltage on kinds and abundances of the product ions was examined. Complex formation of the product ions with neutral species was also investigated. Not only lactate, [M-H] À and its complexes but also ions of condended species, [nM-(n-1)H 2 O-H] À with n = 2-5, and their complexes were observed. The condensation reactions occurred in an aerosol state generated in the heating zone for evaporation. By increasing the concentration of lactic acid, abundances of the product ions were increased and the increase of larger ones was noticeable. By increasing the heating zone temperature, abundances of the product ions were decreased and the decrease of larger ones was remarkable. By increasing the source fragmentor voltage, abundances of small product ions were increased and those of the complexes, [nM-(n-2)H 2 O-H] À with n = 2-5, were significantly decreased. Complex formation of lactate with the neutral condensed species was more favorable than that of the condensed oligomer ions with a neutral lactic acid.The experimental results were explained by energies and structures of the product ions and neutral species obtained by theoretical calculations.

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“…Lactic acid produced by fermentation includes impurities, especially organic acids (such as citric, glyceric, succinic, malic, formic, propionic, fumaric, pyruvic, and acetic acid), monohydroxy alcohols (methanol, ethanol, butanol), lactates (methyl, ethyl and butyl lactates), amino acids, and protein fragments . The available information about the amount and effect of monofunctional impurities on the direct condensation reaction of lactic acid is scarce .…”

Section: Introductionmentioning

confidence: 99%

Direct condensation of lactic acid in the presence or absence of supported zirconium sulfate

Raase

Reichert

Schomäcker

2015

J of Applied Polymer Sci

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Direct condensation of L-lactic acid was studied, aiming at highly crystalline and enantiopure high molecular weight (MW) products. Catalyst-free polylactic acid (PLA) with weight average MW of 80,000 g mol 21 , based on PLA standards, and a crystallinity of 75% is synthesized at 1408C in a fixed-bed reactor under vacuum or nitrogen purging. Supported zirconium sulfate is found to be an efficient and enantioselective catalyst for the melt and solid-state post-condensation of short-chain prepolymers. Small-molecule monohydroxy alcohols, aldehydes, di-and monocarboxylic acids (e.g., acrylic acid [1,700 ppm], propionic acid [1,800 ppm]) are detected in the lactic acid and prepolymers by high performance liquid chromatography, electron spray ionization, and electron impact mass spectroscopy. Thermal degradation of polymer chains, the crystallinity of the prepolymer, and the presence of monofunctional impurities are crucial parameters for the limitation of the MW of the resulting product.

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The Effect of the Impurities in Refinery Process from Fermentation Broth on Lactic Acid Polymerization

Cited by 5 publications

References 11 publications

From Lactic Acid to Poly(lactic acid) (PLA): Characterization and Analysis of PLA and Its Precursors

From Lactic Acid to Poly(lactic acid) (PLA): Characterization and Analysis of PLA and Its Precursors

Complex formation of lactic acid by atmospheric pressure chemical ionization

Direct condensation of lactic acid in the presence or absence of supported zirconium sulfate

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