Diglycol Bis(Carbonates) of Lactic Esters - Lactic Acid Derivatives as Plasticizers

Rehberg, C. E.; Dixon, Marion B.; Dietz, Thomas H.; Fisher, C. H.

doi:10.1021/ie50487a041

Cited by 22 publications

(10 citation statements)

References 3 publications

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“…Lactic acid derived from fermentation of biomass is not only a valuable chemical feedstock for the production of bioplastics, but it is also employed for the production of ethyl lactate and other lactate esters that are found in everyday products such as wine, cosmetics, perfumes, degreasers, and can be used as food additives, solvents, fragrances, and plasticizers 25–30. A significant opportunity, therefore, exists for repurposing commodity PLA into value‐added small molecules through a simple and versatile strategy.…”

Section: Introductionmentioning

confidence: 99%

Transforming polylactide into value‐added materials

Leibfarth

Moreno

Hawker³

et al. 2012

J. Polym. Sci. A Polym. Chem.

103

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The production of chemical building blocks and polymer precursors from biorenewable and sustainable resources is an attractive method to bypass traditional fossil fuel derived materials. Accordingly, we report the organocatalytic recycling of postconsumer polylactide (PLA) into value-added small molecules. This strategy, using the highly active transesterification catalyst triazabicyclodecene, is shown to completely depolymerize PLA in the presence of various alcohols into valuable lactate esters. Using previously used PLA packaging material, the depolymerization is complete in minutes at room temperature and fully retains the stereochemistry of the lactate species. Further, the modularity and utility of this methodology with respect to polyester substrate is detailed by using a variety of functional alcohols to depolymerize both PLA and polyglycolide, with the corresponding ester smallmolecules being used to make new polymeric materials. The opportunities to transform waste streams into value-added chemicals and new materials through simple and versatile chemistry hold significant potential to extend the lifecycle of renewable chemical feedstocks. KEYWORDS: biodegradable; depolymerization; glycolate ester; lactate ester; organic catalysis; polyesters; polyglycolide; polylactide; recycling; transesterification INTRODUCTION As society increasingly deals with inherently limited natural resources, the utilization of 7% of fossil fuels for the production of plastics is a significant drain on petrochemical feedstocks.1 With the demand for polymeric materials increasing, it is imperative to develop building blocks based on renewable and sustainable resources.2 The conversion of biomass to value-added small molecules and polymer precursors is an attractive method to bypass traditional fossil fuel-based chemical production.3-5 For example, polylactide (PLA) has emerged as one of the most promising biorenewable and biodegradable polymers due to its utility in packaging, textile, and biomedical applications. [6][7][8][9] The recent addition of Natureworks TM LLC facility in the US has put annual production capacity of PLA at over 150,000 tons, making it a high-volume commodity material. [10][11][12] This largescale production and the predicted annual growth rate of 19% for bioplastics 13 assures that many new PLA derived products will enter the marketplace in the coming decades.

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Section: Introductionmentioning

confidence: 99%

Transforming polylactide into value‐added materials

Leibfarth

Moreno

Hawker³

et al. 2012

J. Polym. Sci. A Polym. Chem.

103

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“…Alternatively, PLA can be modified by adding plasticisers to obtain more flexible materials [9][10].…”

Section: Introductionmentioning

confidence: 99%

Single-step reactive extrusion of PLLA in a corotating twin-screw extruder promoted by 2-ethylhexanoic acid tin(II) salt and triphenylphosphine

Jacobsen

Fritz

Degée

et al. 2000

Polymer

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The ring opening polymerisation of , -lactide using an equimolar complex of 2-ethylhexanoic acid tin(II) salt Sn(Oct) 2 and triphenylphosphine P( ) 3 as catalyst shows for the first time a reactivity providing a polymerisation propagation rate fast enough to imagine a continuous single-step reactive extrusion process for bulk polymerisation. The ring opening polymerisation has been realised on a corotating closely intermeshing twin-screw extruder, using a specially designed screw concept to provide sufficient energy input and mixing for further enhancement of the propagation rate, without detrimentally enhancing depolymerisation or transesterification reactions. Using one chosen screw and processing concept on a twin-screw extruder with 25 mm diameter and a L/D-ratio of 48, the influence of different processing parameters on the resulting molecular parameters of the Polylactide (PLA) has been determined. Furthermore, the mechanical property profile of the generated PLA-polymers is discussed and related to the molecular parameters.

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“…( 6) Perquin, L. H. C., Dutch Patent 58,545 (Nov. 15, 1946). (7) Ronchase, A., J. Pharm. Chim., 25, 611 (1907); Analyst, 32, 303 (1907).…”

Section: Literature Citedmentioning

confidence: 99%

“…and Dibasic Acids C. E. REHBERG, T. J. DIETZ1, P. E. MEISS2, AND MARION B. DIXON INTEREST in the utilization of lactic acid in the manufacture of plasticizers has been intensified in recent years by published data showing that lactic acid can be.produced at a cost competitive with currently used plasticizer intermediates (8) and that highly efficient plasticizers can be made from lactic acid (7,8). Recurrent shortages and threats of shortages of key intermediates currently used in plasticizer manufacture have stimulated interest in the use of lactic acid as an extender for scarce materials.…”

Section: Plasticizers From Lactic Estersmentioning

confidence: 99%