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Preparation method of 1-pyrenol

A technology of hydroxypyrene and alkoxypyrene, which is applied in the field of preparation of 1-hydroxypyrene, can solve the problems of unfavorable industrialization, cumbersome operation, and many impurities in the reaction, and achieve the advantages of convenient industrial production, mild reaction conditions, and simple preparation method Effect

Active Publication Date: 2016-12-07
上海引盛生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] 1. Alkaline hydrolysis of 1-bromopyrene under high temperature and pressure requires the use of special equipment, high energy consumption, low yield, cumbersome operation, great safety hazards, and is not conducive to industrialization;
[0005] 2. Pyrene acylation, oxidation, and hydrolysis. This method has more impurities and lower yield. The product quality is the bottleneck, and it cannot provide quality requirements that meet the performance of high-purity materials.

Method used

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  • Preparation method of 1-pyrenol
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Examples

Experimental program
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Effect test

Embodiment 1

[0027] Embodiment 1: a kind of preparation method of 1-hydroxypyrene, comprises the following steps:

[0028] Step S1: heat up the sodium alkylate solution to reflux, add 1-bromopyrene for reaction, cool down, and centrifugally dry to obtain 1-alkoxypyrene, wherein in this step, the sodium alkylate solution is used as the synthetic route. What needs to be added in the pre-sequence synthesis, specifically, under the condition of nitrogen protection, raise the temperature of the sodium alkyl alkoxide solution to reflux in the reaction kettle, add 1-bromopyrene in batches, add a batch every 0.5-2 hours, and complete the addition Post-reaction for 10-15 hours.

[0029] Step S2: After the reaction in the reactor is completed, carry out a depressurization operation to recover the alkyl alcohol, slowly cool down to 40-50°C, add ice water to stir, centrifuge, and dry under reduced pressure to obtain 1-alkoxypyrene.

[0030] Step S3: Add 1-alkoxypyrene into DMSO, stir to dissolve, the...

Embodiment 2

[0034] Embodiment 2: a kind of preparation method of 1-hydroxypyrene, comprises the following steps: under the condition of nitrogen protection, add 340kg of 30% sodium methylate methanol solution in the reactor, heat up to reflux, add 170kg of 1-bromopyrene in three batches, each Add a batch in 1 hour, react for 12 hours after the addition, recover methanol under reduced pressure, cool down to 40-45°C, add ice water to stir, centrifuge, and dry under reduced pressure to obtain 134.3kg, yield 95.2%.

[0035] Add 134.3kg of 1-methoxypyrene to 390kg of DMSO, stir to dissolve, then add 90kg of cysteine ​​(2-amino-3-mercaptopropionic acid), 100kg of sodium hydroxide, heat up to 120-130°C, and react After 2 hours, recover 200kg of DMSO under reduced pressure, lower the temperature to 20-22°C, add 500kg of toluene and 600kg of water, let it stand for stratification, control the temperature of the water phase at 20-23°C, slowly add 25% hydrochloric acid, and adjust the pH to 1.8-2.2, ...

Embodiment 3

[0036] Embodiment 3: a kind of preparation method of 1-hydroxypyrene, comprises the following steps: under the condition of nitrogen protection, add 460kg of 30% sodium ethylate ethanol solution in the reactor, heat up to reflux, add 170kg of 1-bromopyrene in 2 batches, each Add a batch in 2 hours, react for 13 hours after the addition, recover ethanol under reduced pressure, cool down to 42-46°C, add ice water to stir, centrifuge, and dry under reduced pressure to obtain 141.1kg, yield 93.5%.

[0037] Add 141.1kg of 1-ethoxypyrene to 390kg of DMSO, stir to dissolve, then add 103kg of 2-amino-4-mercaptobutyric acid, 100kg of sodium hydroxide, heat up to 130-140°C, react for 2.5 hours, and then depressurize Recover 200kg of DMSO, lower the temperature to 20-25°C, add 500kg of toluene and 600kg of water, let it stand for stratification, control the temperature of the water phase at 23-28°C, slowly add 25% hydrochloric acid, adjust the pH to 3-3.5, precipitate the solid, and centr...

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Abstract

The invention relates to a preparation method of 1-pyrenol. The preparation method comprises the following steps of warming an alkyl sodium alkoxide solution for reflux, adding 1-bromine pyrene, performing a reaction for 10-15 hours, recovering a solvent, lowering the temperature, and performing centrifugal drying so as to obtain 1-alkoxyl pyrene; dissolving the 1-alkoxyl pyrene in the solvent, enabling the dissolved 1-alkoxyl pyrene and an amino acid compound containing tail-end sulfydryl to be subjected to a reaction under the condition of inorganic alkali and the temperature rising to 120-170 DEG C for 2-3 hours, recovering the solvent, performing purifying, and performing drying so as to obtain the 1-pyrenol. According to the 1-pyrenol prepared by the method disclosed by the invention, the content is 99%, and the yield is 88% or above.

Description

technical field [0001] The invention relates to the field of fine chemicals, in particular to a preparation method of 1-hydroxypyrene. Background technique [0002] 1-Hydroxypyrene is an important chemical intermediate. It has an important application in the field of new materials, especially COPNA resin. This kind of resin has good performance, good compatibility with graphite, high temperature resistance, roasting, small specific gravity, Corrosion resistance, thermal shock resistance, good heat transfer, good self-lubricating properties, etc., are obviously better than phenolic resin and polyimide resin with simple benzene rings; in addition, this kind of resin has excellent sliding properties, and can be used in friction materials as an important binder. In addition, 1-hydroxypyrene is also a ubiquitous metabolite of polycyclic aromatic hydrocarbons. A large number of experiments have shown that there is an obvious dose-effect relationship between the concentration ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/12C07C37/055
Inventor 顾焕许丽丽
Owner 上海引盛生物科技有限公司