Regioselective synthesis of renewable bisphenols from 2,3-pentanedione and their application as plasticizers

Literature Information

Publication Date 2014-02-24
DOI 10.1039/C4GC00250D
Impact Factor 10.182
Authors

Wouter Schutyser, Steven-Friso Koelewijn, Michiel Dusselier, Joice Thomas, Feng Yu, Maria Josefina Carbone, Mario Smet, Peter Van Puyvelde, Wim Dehaen, Bert F. Sels


View Original

Abstract

2,3-Pentanedione (2,3-PD), a bio-based chemical derived from lactic acid, has the potential to serve as a precursor for the synthesis of novel bisphenols. We developed a solvent-free catalytic strategy for the condensation of phenol with 2,3-PD by using acid catalysts at temperatures ranging from 323 to 373 K. Various soluble and solid acids exhibit high activity, while a high chemoselectivity to bisphenol requires a high phenol to 2,3-PD molar ratio. Bisphenol yields as high as 84% are for instance reported in an excess of phenol in the presence of Nafion NR50. Recycling of the Nafion catalyst after washing with ethanol at room temperature is demonstrated. The regioselectivity in the bisphenol fraction is influenced by the acid strength. A clear trend is presented in which the regioselectivity towards the desired p,p′-isomers increases with increasing acid strength, showing p,p′/o,p′-isomer ratios as high as 100. A tentative mechanism is discussed based on the ionic versus non-ionic pathway. The purified 2,3-PD-derived p,p′-bisphenols are assessed as plasticizers for polyethylene terephthalate (PET), showing promising properties similar to that of the reference bisphenol A, but with a broader processing window due to the lower melting point and higher thermal stability under an inert atmosphere.

Related Literature

Methanol electro-oxidation on platinum modified tungsten carbides in direct methanol fuel cells: a DFT study

Xiao Lin, Zhao-Yang Chen, P. Hu, Shi-Gang Sun, You-Qun Chu

2015-08-25 Paper

DOI: 10.1039/C5CP02072G

Aqueous biphasic systems composed of ionic liquids and polypropylene glycol: insights into their liquid–liquid demixing mechanisms

Catarina M. S. S. Neves, Jesus Lemus, Jorge F. B. Pereira, Mara G. Freire, João A. P. Coutinho

2016-06-24 Paper

DOI: 10.1039/C6CP04023C

Fluorescence fluctuation of an antigen–antibody complex: circular dichroism, FCS and smFRET of enhanced GFP and its antibody

Debmalya Bhunia, Rajdeep Chowdhury, Kankan Bhattacharyya

2015-08-28 Paper

DOI: 10.1039/C5CP04908C

Illuminating solid gas storage in confined spaces – methane hydrate formation in porous model carbons

Lars Borchardt, Winfried Nickel, Mirian Casco, Irena Senkovska, Volodymyr Bon, Dirk Wallacher, Nico Grimm, Simon Krause, Joaquín Silvestre-Albero

2016-07-07 Paper

DOI: 10.1039/C6CP03993F

New organophilic kaolin clays based on single-point grafted 3-aminopropyl dimethylethoxysilane

A. Zaharia, F.-X. Perrin, M. Teodorescu, A.-L. Radu, T.-V. Iordache, A.-M. Florea, D. Donescu, A. Sarbu

2015-08-27 Paper

DOI: 10.1039/C5CP04395F

Troponin structure: its modulation by Ca2+ and phosphorylation studied by molecular dynamics simulations

Juan Eiros Zamora, Maria Papadaki, Andrew E. Messer, Steven B. Marston, Ian R. Gould

2016-07-06 Paper

DOI: 10.1039/C6CP02610A

Strong solvent dependence of linear and non-linear optical properties of donor–acceptor type pyrrolo[3,2-b]pyrroles

Rafał Orłowski, Marzena Banasiewicz, Guillaume Clermont, Frédéric Castet, Rashid Nazir, Mireille Blanchard-Desce, Daniel T. Gryko

2015-07-08 Paper

DOI: 10.1039/C5CP03523F

You might also like

Compound Q&A

What precautions should be taken when handling 4-Methyl-6-(trifluoromethyl)quinoline (CAS: 40716-16-3)?

When handling 4-Methyl-6-(trifluoromethyl)quinoline (CAS: 40716-16-3), safety go...

40716-16-34-Methyl-6-(trifluor...
Compound Q&A

What is 4-(3,5-Difluorophenyl)aniline (CAS: 405058-00-6)?

4-(3,5-Difluorophenyl)aniline is an aromatic organic compound with the CAS numbe...

405058-00-64-(3,5-Difluoropheny...
Compound Q&A

How is 5-{[4-(Trifluoromethyl)phenyl]sulfanyl}-1,2,3-thiadiazole-4-carboxylic acid (CAS: 338982-07-3) typically synthesized?

5-{[4-(Trifluoromethyl)phenyl]sulfanyl}-1,2,3-thiadiazole-4-carboxylic acid can ...

338982-07-35-{[4-(Trifluorometh...
Compound Q&A

What is the market or research trend for 4-Benzylaniline hydrochloride (CAS: 6317-57-3)?

The market for 4-Benzylaniline hydrochloride (CAS: 6317-57-3) is steadily growin...

6317-57-34-Benzylaniline hydr...
Compound Q&A

Is [3-(Diethylsulfamoyl)phenyl]boronic acid (CAS: 871329-58-7) safe?

[3-(Diethylsulfamoyl)phenyl]boronic acid is generally considered safe when handl...

871329-58-7[3-(Diethylsulfamoyl...
Compound Q&A

What are the main uses of 3-Bromo-2,5-dimethoxyaniline (CAS: 115929-62-9)?

3-Bromo-2,5-dimethoxyaniline is mainly used in the pharmaceutical and chemical i...

115929-62-93-Bromo-2,5-dimethox...
Compound Q&A

What regulatory guidelines apply to N-Methyl-1-(5-methyl-1H-indol-3-yl)methanamine (CAS: 915922-67-7)?

N-Methyl-1-(5-methyl-1H-indol-3-yl)methanamine (CAS: 915922-67-7) is subject to ...

915922-67-7N-Methyl-1-(5-methyl...
Compound Q&A

What industries use Carbamic acid, N-[(5S)-5,6-diamino-6-oxohexyl]-, 1,1-dimethylethyl ester (CAS: 24828-96-4)?

This compound is primarily used in the pharmaceutical industry for the synthesis...

24828-96-4Carbamic acid, N-[(5...
Compound Q&A

How should 2-Methyl-2-propanyl [(1S,3R)-3-aminocyclohexyl]carbamate (CAS: 1298101-47-9) be stored?

2-Methyl-2-propanyl [(1S,3R)-3-aminocyclohexyl]carbamate (CAS: 1298101-47-9) sho...

1298101-47-92-Methyl-2-propanyl ...
Compound Q&A

What industries use Ethyl 2-bromo-4,4,4-trifluorobutanoate (CAS: 367-33-9)?

Ethyl 2-bromo-4,4,4-trifluorobutanoate (CAS: 367-33-9) is utilized in the pharma...

367-33-9Ethyl 2-bromo-4,4,4-...

Source Journal

Green Chemistry

Green Chemistry
CiteScore: 16.1
Self-citation Rate: 7.5%
Articles per Year: 944

Green Chemistry provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on, but not limited to, the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998). Green chemistry is the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry is at the frontiers of this continuously-evolving interdisciplinary science and publishes research that attempts to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. Submissions on all aspects of research relating to the endeavour are welcome. The journal publishes original and significant cutting-edge research that is likely to be of wide general appeal. To be published, work must present a significant advance in green chemistry. Papers must contain a comparison with existing methods and demonstrate advantages over those methods before publication can be considered. For more information please see this Editorial. Coverage includes the following, but is not limited to: Design (e.g. biomimicry, design for degradation/recycling/reduced toxicity…) Reagents & Feedstocks (e.g. renewables, CO2, solvents, auxiliary agents, waste utilization…) Synthesis (e.g. organic, inorganic, synthetic biology…) Catalysis (e.g. homogeneous, heterogeneous, enzyme, whole cell…) Process (e.g. process design, intensification, separations, recycling, efficiency…) Energy (e.g. renewable energy, fuels, photovoltaics, fuel cells, energy storage, energy carriers…) Applications (e.g. electronics, dyes, consumer products, coatings, pharmaceuticals, preservatives, building materials, chemicals for industry/agriculture/mining…) Impact (e.g. safety, metrics, LCA, sustainability, (eco)toxicology…) Green chemistry is, by definition, a continuously-evolving frontier. Therefore, the inclusion of a particular material or technology does not, of itself, guarantee that a paper is suitable for the journal. To be suitable, the novel advance should have the potential for reduced environmental impact relative to the state of the art. Green Chemistry does not normally deal with research associated with 'end-of-pipe' or remediation issues.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.