Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Synthesis method of hydroquinone

A technology of hydroquinone and synthesis method, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of difficult catalyst recovery, low molar ratio, high toxicity, etc. Low product, mild effects of temperature and pressure

Inactive Publication Date: 2012-02-15
NANJING UNIV OF INFORMATION SCI & TECH
View PDF2 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because acetonitrile is used as the reaction medium, the toxicity of the reaction process is relatively large, and the phenol / H 2 o 2 The molar ratio of H is too low, H 2 o 2 The dosage is too large, in addition, catalyst recovery is difficult

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis method of hydroquinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Take 10 g phenol and 5 g copper sodium compound salt (CuSO 4 : NaCl = 1:3, purchased from Shanghai Reagent Factory) was added into a three-necked flask containing 50 mL of methanol, fed with oxygen, refluxed at 60°C for 6 hours, and monitored by TLC.

[0031] (2) Distill methanol off, add 10 mL of water to the residue, and steam distill until the distillate is colorless. Concentrate, cool, filter, and isolate 8.62 g of p-benzoquinone from the distillate (yield: 75.0 %). The mother liquor was concentrated by steam distillation, cooled, and filtered to isolate 2.07 g of phthaloquinone (yield: 18.0 %).

[0032] (3) Take 8.62 g of p-quinone and 9.0 g of ammonium thiosulfate / ammonium sulfate mixture (ammonium thiosulfate 68.5wt%, ammonium sulfate 31.5wt%, the residue after extracting potassium thiocyanate from Nangang steelmaking wastewater) Add it into 17 mL of hot water, stir for 20 minutes, adjust the pH value to 1 with sulfuric acid, cool, and precipitate the crude...

Embodiment 2

[0036] (1) Take 50 g phenol and 5 g copper sodium compound salt (CuSO 4 :NaCl=1:2, CuSO 4 and NaCl were purchased from Shanghai Reagent Factory) into a three-necked flask containing 250 mL of ethanol, fed with oxygen, refluxed at 70°C for 2 hours, and monitored the reaction progress by TLC.

[0037] (2) Ethanol was distilled off, 50 mL of water was added to the residue, and steam distilled until the distillate was colorless. Concentrate, cool, filter, and isolate 43.3 g of p-benzoquinone from the distillate (yield: 75.4%). The mother liquor was concentrated by steam distillation, cooled, and filtered to isolate 10.2 g of phthaloquinone (yield: 17.8 %).

[0038] (3) Take 43.3 g of p-quinone and 45.0 g of ammonium thiosulfate / ammonium sulfate mixture (ammonium thiosulfate 68.5wt%, ammonium sulfate 31.5wt%, the residue after extracting potassium thiocyanate from Nangang steelmaking wastewater) Add it into 85 mL of hot water, stir for 20 minutes, adjust the pH value to 1 with s...

Embodiment 3

[0042] (1) Take 100 g phenol and 7.5 g copper-sodium compound salt (Cu(NO 3 ) 2 : NaCl = 1:3, Cu(NO 3 ) 2 and NaCl (purchased from Shanghai Reagent Factory) were added to a three-necked flask containing 500 mL of propanol, heated (at a temperature of about 70°C), fed with oxygen, and the reaction was monitored by TLC, and the reaction was complete within 2 hours.

[0043] (2) Ethanol was distilled off, 100 mL of water was added to the residue, and steam distilled until the distillate was colorless. Concentrate, cool, filter, and isolate 87.2 g of p-benzoquinone from the distillate (yield: 75.9 %). The mother liquor was concentrated by steam distillation, cooled and filtered to isolate 20.1 g of phthaloquinone (yield: 17.5 %).

[0044] (3) Take 87.2 g of p-quinone and 90.7 g of ammonium thiosulfate / ammonium sulfate mixture (ammonium thiosulfate 68.5wt%, ammonium sulfate 31.5wt%, the residue after extracting potassium thiocyanate from Nangang steelmaking wastewater) Add it ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a synthesis method of hydroquinone. The method is characterized by comprising the following steps: carrying out catalytic oxidation on phenol and oxygen to generate a mixture of p-benzoquinone and o-benzoquinone, wherein a catalyst is copper and sodium complex salt; distilling to remove solvent, adding water in residual materials, and separating p-benzoquinone and o-benzoquinone by distillation; reducing separated p-benzoquinone with a reducing agent to obtain hydroquinone, filtering out hydroquinone crude product and recrystallizing so as to obtain hydroquinone crystal; and concentrating a mother liquid obtained by filtering out hydroquinone or catechol crude product to obtain an ammonium sulfate fertilizer. The synthesis method has simple process, mild reaction conditions and short reaction period, and the yield of hydroquinone in the product is larger than that of catechol.

Description

[0001] technical field [0002] This patent relates to a synthetic method of chemical products, specifically, a synthetic method of hydroquinone. It belongs to the technical field of medicinal chemistry. Background technique [0003] Hydroquinone is an important chemical product, which is widely used in chemical, pharmaceutical, pesticide, spice, rubber and other industries. The synthetic method of hydroquinone is as follows: [0004] (1) The Reppe method is to react acetylene with carbon monoxide to generate hydroquinone under the conditions of Ru and Rh catalysts, a temperature of 100-300 °C, and a pressure of 100-350 MPa. The process is simple, but the required catalyst is expensive and difficult to recycle. [0005] (2) The aniline oxidation method is to oxidize aniline to p-benzoquinone with manganese dioxide or sodium dichromate under acidic conditions in the presence of sulfuric acid; then reduce p-benzoquinone to p-benzoquinone with iron powder under acidic condit...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C39/08C07C37/07
Inventor 张超智
Owner NANJING UNIV OF INFORMATION SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com