Synthesis method of 1,2-diphenoxyethane thermosensitive sensitizer

A diphenoxyethane heat-sensitive sensitizer and a technology of a synthesis method, which are applied in the first field, can solve problems such as high difficulty in industrialization, long reaction time, and large investment in equipment, and achieve short reaction time, easy conditions, and easy raw materials. The effect

Inactive Publication Date: 2017-10-03
SHENYANG GOLD JYOUKI TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Chinese patent (publication number CN103073398A) and Chinese patent (publication number CN102276432A), both documents are all to use sodium hydroxide lye as acid-binding agent, and its reaction time is long, and yield is low
In addition, Song Yu of Shenyang Photosensitive Chemical Research Institute and others use dichloroethane as raw material, high temperature and high pressure reaction, large investment in equipment, and great difficulty in industrialization

Method used

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  • Synthesis method of 1,2-diphenoxyethane thermosensitive sensitizer
  • Synthesis method of 1,2-diphenoxyethane thermosensitive sensitizer
  • Synthesis method of 1,2-diphenoxyethane thermosensitive sensitizer

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Present embodiment 1, the synthetic route of 2-diphenoxyethane thermal sensitizer is as follows:

[0020]

[0021] Add 100kg of melted phenol and 420kg of dichloroethane into the reactor, heat up to 85°C and reflux, slowly add 161kg of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) dropwise, After dropping, react for 3 hours, the gas phase detection phenol reaction is complete, and the reaction product is 2-chlorophenetole; Dichloroethane is distilled off under reduced pressure, and 1,8-diazabicyclo[5.4.0]undec-7 -ene (DBU) 161kg, heat up to 130°C, add 100kg of phenol dropwise, follow up and detect that the reaction of 2-chlorophenetole is complete, stop adding phenol dropwise, cool down to 100°C, add 100kg of water, stir for 1h, let go of the water phase, and then add the organic phase Add 100kg of water, stir for 1h, slowly cool down, solids are precipitated, filter, and the filter cake is recrystallized with ethanol to obtain 408kg of white crystals, the yield is 89.82%...

Embodiment 2

[0026] Present embodiment 1, the synthetic route of 2-diphenoxyethane thermal sensitizer is as follows:

[0027]

[0028] Add 100kg of melted phenol and 420kg of dichloroethane into the reactor, heat up to 85°C and reflux, slowly add 1,4-diazabicyclo[2.2.2]octane (DABCO) 119kg dropwise, After reacting for 3 hours, the phenol reaction was detected by the gas phase, and the reaction product was 2-chlorophenetole; the dichloroethane was distilled off under reduced pressure, and 1,4-diazabicyclo[2.2.2]octane (DABCO) 119kg was added , raise the temperature to 130°C, add 100kg of phenol dropwise, track and detect that the reaction of 2-chlorophenetole is complete, stop the dropwise addition of phenol, cool down to 100°C, add 100kg of water, stir for 1h, let go of the water phase, add 100kg of water to the organic phase, stir for 1h, Slowly lower the temperature, solids are precipitated, filtered, and the filter cake is recrystallized with ethanol to obtain 391kg of white crystals...

Embodiment 3

[0030] Present embodiment 1, the synthetic route of 2-diphenoxyethane thermal sensitizer is as follows:

[0031]

[0032] Add 100kg of melted phenol and 420kg of dichloroethane into the reaction kettle, raise the temperature to 85°C and reflux, slowly add 138kg of N,N-diisopropylethylamine (DIPEA) dropwise, and react for 4 hours, and detect the phenol by gas phase The reaction is complete, and the reaction product is 2-chlorophenetole; the dichloroethane is distilled off under reduced pressure, and 138kg of N,N-diisopropylethylamine (DIPEA) is added, the temperature is raised to 130°C, and 100kg of phenol is added dropwise. Detect that the reaction of 2-chlorophenetole is complete, stop adding phenol dropwise, cool down to 100°C, add 100kg of water, stir for 1h, let go of the water phase, add 100kg of water to the organic phase, stir for 1h, cool down slowly, solids are precipitated, filter, and use as a filter cake Recrystallization from ethanol gave 332kg of white crystal...

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Abstract

The invention relates to the field of sensitizers for thermosensitive paper, particularly a synthesis method of a high-purity 1,2-diphenoxyethane thermosensitive sensitizer. The method comprises the following steps: adding phenol and dichloroethane into a reaction kettle, performing heating under reflux, dropwisely adding an acid-binding agent into the reaction kettle, performing reaction until no phenol is detected, performing reduced pressure distillation to remove the dichloroethane, supplementing the acid-binding agent, performing heating, dropwisely adding the phenol, performing tracking detection until 2-chlorophenetole reacts completely, stopping dropwisely adding the phenol, performing water washing to remove the salt, and performing ethanol recrystallization to obtain the product. The reaction condition is mild: the maximum temperature is controlled at 120-150 DEG C, so the condition is accessible. The method has the advantages of short reaction time, accessible raw materials, simple technical operation process, recyclable raw materials and high product purity, and is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of sensitizers for heat-sensitive paper, in particular to a method for synthesizing high-purity 1,2-diphenoxyethane heat-sensitive sensitizers. Background technique [0002] 1,2-Diphenoxyethane is a sensitizer for thermal paper. The commonly used production method is to prepare by reacting 1,2-dibromoethane and phenol, which leads to relatively high production costs, so the choice of 1 , The preparation method of 1,2-diphenoxyethane with 2-dichloroethane as the starting material has attracted the attention of research institutes. [0003] Chinese patent (publication number CN103073398A) and Chinese patent (publication number CN102276432A), both documents are to use sodium hydroxide lye as an acid-binding agent, and its reaction time is long and the yield is low. In addition, the Chinese patent (publication number CN104710287A) uses sodium carbonate, potassium carbonate, and sodium hydroxide as alkali, polyethylene gl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/16C07C43/205
CPCC07C41/16C07C43/2055C07C43/225
Inventor 姜鹏飞于凯闫奇
Owner SHENYANG GOLD JYOUKI TECH
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