Step-Growth Polyesters with Biobased (R)-1,3-Butanediol

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https://doi.org/10.13020/7fkh-c288
https://hdl.handle.net/11299/215257

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Keywords

Polyesters

Polymerization

Biobased

Collection period

2018-08-01
2020-03-01

Date completed

2020-05-05

Date updated

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Journal Title

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Volume Title

Title

Step-Growth Polyesters with Biobased (R)-1,3-Butanediol

Published Date

2020-08-26

Authors

DeRosa, Christopher A

Kua, Xiang Qi

Bates, Frank S

Hillmyer, Marc A

Group

University of Minnesota, Department of Chemistry

Author Contact

Hillmyer, Marc A
hillmyer@umn.edu

Type

Dataset

Abstract

These files contain primary data along with associated output from "Step-Growth Polyesters with Biobased (R)-1,3-Butanediol" by Hillmyer et al. We present the synthesis and characterization of polymers containing 1,3-butanediol, also known as butylene glycol. Butylene glycol (BG) can be prepared from petroleum or sugar-based feedstocks. Petrol-based BG (petrol-BG) is isolated as a racemic mixture, whereas the bio-based BG from sugar that we utilized (Bio-BG), is enantiopure upon purification (>99.7%). In the presence of a titanium catalyst, polyesters were prepared by transesterification polymerization between petrol- or Bio-BG and various aliphatic and aromatic diacid derivatives. Polymers were analyzed by size-exclusion chromatography (SEC), 1H NMR and 13C NMR spectroscopies, thermogravimetric analysis (TGA), and differential scanning calorimetry (DSC). The synthesized polyesters were statistical in nature, according to 13C NMR spectroscopy, a result of the asymmetric nature of the BG-starting material. As a result, many of the polyesters were amorphous in nature with low thermal glass transitions (Tg) and no melting points (Tm). In many of the polyester derivatives, the racemic petrol-based and enantiopure bio-based BG polymers were nearly identical in thermal performance. Differences arose in semi-crystalline polyesters with long, aliphatic backbones (e.g., 1,14-tetradecanediocic acid; C14 diacid) or regioregular 4-hydroxybenzoate polyesters. This suggests the polymer microstructure (statistical versus sequenced) and the optical activity (racemic versus enantiopure) are important determinates in establishing the structure-property relationships in BG-containing polyesters. This work establishes synthetic protocols and the foundation for materials based on BG-containing polymers.

Description

Full description in the file "README_Stepgrowth BG Polymers.txt". The files below includes the raw data associated with the synthesis and characterization of butylene glycol containing polyesters. File folders are organized by the characterization method (e.g. Raw Nuclear Magnetic Resonance Spectroscopy (NMR), with further organization though expimernts in the manuscripts. Files are named after polymer samples, and knowledge of the polymer names referred to the paper and required to understand the nomenclature.NMR spectroscopy files are the raw data generated from the Bruker software and can be accessed through MNova or Bruker software. CDX files can be opened with proprietary ChemDraw 12.0, distributed by CambridgeSoft. All other files (DSC, SEC , and TGA) are provided as CSV files.

Referenced by

DeRosa, C.A., Kua, X.Q., Bates F,S., Hillmyer, M.A. (2020). Step-Growth Polyesters with Biobased (R)-1,3-Butanediol, Industrial & Engineering Chemistry Research.
https://doi.org/10.1021/acs.iecr.0c03009

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CC0 1.0 Universal
http://creativecommons.org/publicdomain/zero/1.0/

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Data Repository for U of M (DRUM)
CSP Research Data

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Genomatica

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Previously Published Citation

Suggested citation

DeRosa, Christopher A; Kua, Xiang Qi; Bates, Frank S; Hillmyer, Marc A. (2020). Step-Growth Polyesters with Biobased (R)-1,3-Butanediol. Retrieved from the Data Repository for the University of Minnesota (DRUM), https://doi.org/10.13020/7fkh-c288.

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