Depolymerization of Cellulose in Water Catalyzed by Phenylboronic Acid Derivatives

Noam Levi, Alexander M. Khenkin, Bekele Hailegnaw, Ronny Neumann

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Based on the knowledge that o-aminomethylphenylboronic acids reversibly bind to carbohydrates, relevant water-soluble derivatives of the former were prepared by appending hydrophilic tethers. In this way the phenylboronic acid derivatives were used to hydrolytically dissolve, i.e. depolymerize cellulose in water at nearly neutral pH values. Some of these hydrophilic tethers consisted of moieties that were surmised to be able to promote hydrolysis of the glycosidic bonds such as a carboxylic acid, phosphonic acid as weak Bronsted acids, or an imidazole functionality as a nucelophilic catalyst; water-soluble polyethylene glycol and polyethyenelimine appendages were also used. The results show that at around 120 °C efficient hydrolysis of cellulose to form water-soluble oligosaccharides could be attained in a period of 24 h. Importantly preimpregnation of a morpholine substituted o-aminomethylphenylboronic acid led to the very selective formation of glucose.

Original languageEnglish
Pages (from-to)5799-5803
Number of pages5
JournalACS Sustainable Chemistry and Engineering
Volume4
Issue number10
DOIs
Publication statusPublished - Oct 3 2016

Fingerprint

Depolymerization
Cellulose
cellulose
Derivatives
Acids
Water
acid
Hydrolysis
hydrolysis
water
Carboxylic Acids
Oligosaccharides
carboxylic acid
Carbohydrates
Carboxylic acids
Polyethylene glycols
Glucose
carbohydrate
glucose
Catalysts

Keywords

  • Catalysis
  • Cellulose
  • Glucose
  • Hydrolysis
  • Phenylboronic acid

ASJC Scopus subject areas

  • Chemistry(all)
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Renewable Energy, Sustainability and the Environment

Cite this

Depolymerization of Cellulose in Water Catalyzed by Phenylboronic Acid Derivatives. / Levi, Noam; Khenkin, Alexander M.; Hailegnaw, Bekele; Neumann, Ronny.

In: ACS Sustainable Chemistry and Engineering, Vol. 4, No. 10, 03.10.2016, p. 5799-5803.

Research output: Contribution to journalArticle

Levi, Noam ; Khenkin, Alexander M. ; Hailegnaw, Bekele ; Neumann, Ronny. / Depolymerization of Cellulose in Water Catalyzed by Phenylboronic Acid Derivatives. In: ACS Sustainable Chemistry and Engineering. 2016 ; Vol. 4, No. 10. pp. 5799-5803.
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