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Related Concept Videos

Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

3.3K
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
3.3K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

5.7K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
5.7K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

9.9K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
9.9K
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

1.7K
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
1.7K
Aldehydes and Ketones with Water: Hydrate Formation01:20

Aldehydes and Ketones with Water: Hydrate Formation

3.1K
An oxygen-based nucleophile, like water, can undergo addition reactions with aldehydes and ketones. The reaction leads to the formation of hydrates, also referred to as 1,1-diols or geminal diols.
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...
3.1K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K

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Related Experiment Video

Updated: Jun 12, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Advances in biosynthesis and downstream processing of diols.

Yongfei Liu1, Chijian Zhang2, An-Ping Zeng1

  • 1Center for Synthetic Biology and Integrated Bioengineering, Westlake University, Hangzhou 310030, Zhejiang, China; School of Engineering, Westlake University, Hangzhou 310030, Zhejiang, China; Zhejiang Provincial Key Laboratory of Intelligent Low-Carbon Biosynthesis, Hangzhou 310030, Zhejiang, China; Research Center for Industries of the Future, Westlake University, No. 600 Dunyu Road, 310030, Zhejiang Province, China.

Biotechnology Advances
|September 21, 2024
PubMed
Summary

This review explores microbial production of key diols like 1,3-propanediol (PDO) and butanediols (BDOs). It highlights metabolic platforms and downstream processing for bio-based diol manufacturing.

Keywords:
1,3-butanediol1,3-propanediol1,4-butanediolDiolDownstream processingMetabolic engineeringSynthetic biology

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Area of Science:

  • Biotechnology
  • Chemical Engineering
  • Industrial Microbiology

Background:

  • Diols are vital platform chemicals with broad applications in various industries.
  • 1,3-propanediol (PDO), 1,4-butanediol (1,4-BDO), and 1,3-butanediol (1,3-BDO) are key monomers for polymers and plastics.
  • Commercialization of bio-based diols is crucial for biomanufacturing, especially in the fiber industry.

Purpose of the Study:

  • To review microbial production routes for PDO, 1,4-BDO, and 1,3-BDO.
  • To introduce and discuss metabolic platforms for generic diol bioconversion.
  • To analyze downstream processing of PDO as a case study for industrial diol purification.

Main Methods:

  • Comprehensive literature review of microbial diol production.
  • Analysis of different microbial strains and biological pathways.
  • Examination of metabolic engineering strategies for diol synthesis.
  • Evaluation of downstream processing techniques for PDO.

Main Results:

  • Overview of various microbial strains and biological routes for PDO, 1,4-BDO, and 1,3-BDO production.
  • Introduction of novel metabolic platforms for versatile diol bioconversion.
  • Detailed assessment of PDO downstream processing, including advantages and disadvantages.

Conclusions:

  • Microbial production of diols offers a sustainable alternative for industrial chemicals.
  • Metabolic platforms provide a versatile approach for producing various diols.
  • Downstream processing remains a critical challenge for the industrial-scale purification of bio-based diols.