Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Benzene to Phenol via Cumene: Hock Process01:27

Benzene to Phenol via Cumene: Hock Process

3.1K
The synthesis of phenol from benzene via cumene and cumene hydroperoxide is called the Hock process. First, a Friedel–Crafts alkylation reaction of benzene with propene gives cumene. Then cumene forms cumene hydroperoxide via a radical chain reaction. In the chain initiation step, the benzylic hydrogen is abstracted to give a benzylic radical. In the chain propagation step, the benzylic radical reacts with an oxygen diradical to form a cumene hydroperoxide radical. The cumene...
3.1K
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

2.6K
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
2.6K
Types of Step-Growth Polymers: Polyesters01:20

Types of Step-Growth Polymers: Polyesters

2.2K
The introduction of polyesters has brought major development to the textile industry. The wrinkle-free behavior of polyester blends has eliminated the need for starching and ironing clothes.
Polyesters are commonly prepared from terephthalic acid and ethylene glycol; the crude product is known as poly(ethylene terephthalate) or PET. However, polyesters are synthesized industrially by transesterification of dimethyl terephthalate with ethylene glycol at 150 °C. The two reactants and the...
2.2K
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

2.0K
Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
2.0K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

2.5K
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
2.5K
Physical Properties of Alcohols and Phenols02:32

Physical Properties of Alcohols and Phenols

13.9K
Alcohols are organic compounds in which a hydroxy group is attached to a saturated carbon. Phenols are a class of alcohols containing a hydroxy group attached to an aromatic ring. The physical properties of the alcohols and phenols are influenced by hydrogen bonding due to the oxygen–hydrogen dipole in the hydroxy functional group and dispersion forces between alkyl or aryl regions of alcohol and phenol molecules.
Alcohols possess a higher boiling point than aliphatic hydrocarbons of...
13.9K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Electrochemical Oxygen-Atom Transfer to Alkenes and Pyridines with a Mn-Porphyrin Catalyst Using Water as the Source of Oxygen.

ACS catalysis·2026
Same author

Functional and Network PHAs via Stereoselective Polymerization and Tailored Post-Transformation.

Angewandte Chemie (International ed. in English)·2026
Same author

Mechanism of O<sub>2</sub>/NO-Promoted Oxidative C-C Bond Cleavage in Linear Alkanes.

Journal of the American Chemical Society·2026
Same author

Positional Isomer of P3HB by Stereoselective Polymerization of Racemic α-Methyl-β-propiolactone Delivers Polyethylene-like Properties.

Journal of the American Chemical Society·2026
Same author

Lignin to adipic acid in a high-yield chemical and biological redox process.

Nature·2026
Same author

Fe(porphyrin)-Catalyzed Alkene Epoxidation with NaOCl: A Practical Small- and Large-Scale Alternative to <i>m</i>CPBA.

Journal of the American Chemical Society·2026

Related Experiment Video

Updated: May 25, 2025

Preparation of Hollow Polystyrene Particles and Microcapsules by Radical Polymerization of Janus Droplets Consisting of Hydrocarbon and Fluorocarbon Oils
07:01

Preparation of Hollow Polystyrene Particles and Microcapsules by Radical Polymerization of Janus Droplets Consisting of Hydrocarbon and Fluorocarbon Oils

Published on: January 25, 2018

9.9K

Can the Hock Process Be Used to Produce Phenol from Polystyrene?

Doohyun Baek1,2, Abdullah J Al Abdulghani3, Dylan J Walsh1,2

  • 1Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706, United States.

Journal of the American Chemical Society
|February 26, 2025
PubMed
Summary

Researchers explored converting waste polystyrene (PS) into phenol using a modified Hock process. Neighboring phenyl rings in PS hinder the reaction, resulting in lower phenol yields compared to small molecules.

More Related Videos

Stabilizing Hepatocellular Phenotype Using Optimized Synthetic Surfaces
08:50

Stabilizing Hepatocellular Phenotype Using Optimized Synthetic Surfaces

Published on: September 26, 2014

10.2K
Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer
10:22

Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer

Published on: November 30, 2020

3.4K

Related Experiment Videos

Last Updated: May 25, 2025

Preparation of Hollow Polystyrene Particles and Microcapsules by Radical Polymerization of Janus Droplets Consisting of Hydrocarbon and Fluorocarbon Oils
07:01

Preparation of Hollow Polystyrene Particles and Microcapsules by Radical Polymerization of Janus Droplets Consisting of Hydrocarbon and Fluorocarbon Oils

Published on: January 25, 2018

9.9K
Stabilizing Hepatocellular Phenotype Using Optimized Synthetic Surfaces
08:50

Stabilizing Hepatocellular Phenotype Using Optimized Synthetic Surfaces

Published on: September 26, 2014

10.2K
Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer
10:22

Designed for Molecular Recycling: A Lignin-Derived Semi-aromatic Biobased Polymer

Published on: November 30, 2020

3.4K

Area of Science:

  • Polymer Chemistry
  • Chemical Engineering
  • Sustainable Materials

Background:

  • Polystyrene (PS) has a low recycling rate, necessitating chemical conversion strategies.
  • Current oxidation methods for PS yield benzoic acid, a low-demand product.
  • Phenol is a high-volume chemical, but direct conversion from PS is unachieved.

Purpose of the Study:

  • To investigate the adaptation of the Hock process for converting waste polystyrene into phenol.
  • To understand the chemical reactivity of polystyrene under Hock process conditions.
  • To identify challenges and insights for polymer-to-chemical conversion.

Main Methods:

  • Autoxidation of benzylic C-H bonds in PS model compounds and PS to form hydroperoxides.
  • Acid-promoted rearrangement of hydroperoxides to yield phenol.
  • Experimental and computational studies on dimeric and trimeric PS models.
  • Analysis of conformational constraints impacting hydrogen-atom transfer.

Main Results:

  • The Hock process was adapted to polystyrene, yielding phenol and an oxygenated polymer.
  • Neighboring phenyl rings in PS impose conformational constraints, increasing the barrier to hydrogen-atom transfer.
  • These steric effects reduce phenol yields from polystyrene compared to small-molecule feedstocks.

Conclusions:

  • Adapting small-molecule processes like the Hock process to polymers presents unique challenges due to macromolecular structure.
  • Understanding polymer-specific reactivity is crucial for developing efficient chemical recycling methods.
  • The findings offer insights for converting other polymers into valuable chemicals.