CN101613257A - A kind of production process for resorcinol - Google Patents
A kind of production process for resorcinol Download PDFInfo
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- CN101613257A CN101613257A CN200810050151A CN200810050151A CN101613257A CN 101613257 A CN101613257 A CN 101613257A CN 200810050151 A CN200810050151 A CN 200810050151A CN 200810050151 A CN200810050151 A CN 200810050151A CN 101613257 A CN101613257 A CN 101613257A
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Abstract
A kind of production process for resorcinol belongs to fine chemistry industry organic raw material technical field.Be raw material with benzene through sulfonation, in and operation, the sulfurous gas that produces in the neutralization reaction step feeds in the extraction solvent, treats its weightening finish 25～30% as the acidizing extraction solvent, the product of neutralization reaction is pulverized alkali fusion material cooling back behind alkali fusion; In reactor, add the acidizing extraction solvent, under agitation add the alkali fusion material after pulverizing in batches, drip water simultaneously, be warming up to 50～85 ℃, acidification reaction 0.5～2h, reaction product prepares Resorcinol through separation, filtration, distillation process.Because acidifying is finished, and is completely free of the dependence to water, realize the zero release of waste water in organic phase.
Description
Technical field
The invention belongs to fine chemistry industry organic raw material technical field, be specifically related to a kind of production process for resorcinol.
Background technology
Sulfonated alkali fusion method is the tradition and the main method of at present producing phenols in the world, wherein again with Resorcinol production according to representativeness.Resorcinol is a kind of important meticulous Organic Chemicals, is widely used in fields such as agricultural, dyestuff, coating, medicine, plastics, rubber, electronic chemical product.Wherein be mainly used in preparation tire fabric impregnation and wood gluing plate high performance adhesive, benzophenone UV light absorber, organic intermediate meta-aminophenol etc.Sulfonated alkali fusion method is the traditional method of producing phenols in the world, and sparetime universities of state-owned enterprise such as China, India, the U.S., Russia adopt this method to produce more at present.Its main raw material is benzene, sulphonating agent (sulfuric acid, sulphur trioxide), and auxiliary material is alkali (sodium hydroxide).Reaction process is: sulfonation-neutralization-alkali fusion-acidifying-extraction-distillation etc.
The subject matter that the technology of the Resorcinol of sulfonated alkali fusion method production at present exists is: consume a large amount of strong acid and strong bases, produce a large amount of inorganic salt and waste liquid simultaneously.1 ton of Resorcinol of every production need consume 31% 11.8 tons of hydrochloric acid, 7.2 tons in consumption sodium hydroxide, produce 1.8 tons in sodium sulfate, 3.5 tons of S-WATs, discharge waste liquid 15M3 approximately, the main source of waste liquid is the raffinate that contains saturated salt and high-concentration phenol, these treating waste liquid difficulty are bigger, processing costs is polluted more serious than higher.
Although adopt certain methods such as resin adsorption method, biological oxidation process, extractive distillation method, film reverse osmosis method etc., can handle, reduce saliferous, phenolic wastewater, fail fundamentally to solve the generation of waste liquid, and dispose waste liquid also will certain cost.
Summary of the invention
It is big to the objective of the invention is to solve the wastewater discharge that exists in the existing sulfonation method production Resorcinol technological process, consume a large amount of technical problems such as strong acid and strong base, providing a kind of merges acidizing process and extraction process, the production process for resorcinol that acidifying is carried out in organic phase, thereby shortened technical process, stopped the generation of waste water.
The objective of the invention is to be achieved through the following technical solutions:
Production process for resorcinol of the present invention, be raw material with benzene through sulfonation, in and operation, the sulfurous gas that produces in the neutralization reaction step feeds in the extraction solvent, treats that its weightening finish 25～30% is as the acidizing extraction solvent, the product of neutralization reaction is pulverized alkali fusion material cooling back behind alkali fusion; In reactor, add the acidizing extraction solvent, under agitation add the alkali fusion material after pulverizing in batches, drip water simultaneously, be warming up to 50～85 ℃, acidification reaction 0.5～2h, reaction product prepares Resorcinol through separation, filtration, distillation process.
Described extraction solvent is any one in n-butyl acetate, propyl carbinol, ether, isopropyl ether, pimelinketone or the hexone.
When described extraction solvent was n-butyl acetate, the acidification reaction temperature was preferably 82 ℃.
When described extraction solvent was propyl carbinol, the acidification reaction temperature was preferably 80 ℃.
When described extraction solvent was ether, the acidification reaction temperature was preferably 50 ℃.
When described extraction solvent was isopropyl ether, the acidification reaction temperature was preferably 60 ℃.
When described extraction solvent was pimelinketone, the acidification reaction temperature was preferably 85 ℃.
When described extraction solvent was hexone, the acidification reaction temperature was preferably 70 ℃.
Compare with prior art, beneficial effect of the present invention is as follows:
(1) because acidifying is finished, is completely free of dependence in organic phase, realizes the zero release of waste water water.
(2) because acidifying is finished in organic phase, the side reaction in the acidification reaction is reduced, improved yield.
(3) acidifying and extractive reaction are finished more rapidly, shortened when producing platform, increase the throughput of device.
Embodiment
The following example will further specify the present invention.
Embodiment 1
Add 1000Kg benzene (about 1136L) and the Powdered thenardite of 60Kg in the 5000L reactor, stir, slowly drip 65% oleum, control reaction temperature is no more than 45 ℃, adds the 1100Kg65% oleum in 20 minutes.Be warming up to 75 ℃, be incubated 10 minutes.
Add the Powdered thenardite of 95Kg in reaction product once more, control reaction temperature is no more than and drips sulfan 1070Kg under 165 ℃ of situations, adds in 40 minutes.Be warming up to 175 ℃ ± 2 ℃, be incubated 1 hour.
Add S-WAT 1800Kg in the 8000L reactor, water 2000Kg stirs, and is warming up to more than 80 ℃, and to wherein dripping above-mentioned sulfonated products, control reaction temperature is no more than 95 ℃.The pH value that dropwises back solution is added 30% sodium hydroxide and is regulated pH value to 8～9 below 4, keeps the temperature suction filtration, washes twice.Filtrate is treated alkali fusion usefulness.The sulfurous gas that produces in the reaction process feeds in the 5200L n-butyl acetate, treats that its weightening finish 30% back is stand-by.
Heating and melting in the alkali fusion reactor of the 10000L that the 3700Kg sodium hydrate solid is added; controlled temperature is at 320 ± 2 ℃; agitation condition drips in two sulfonated liquids and filtrated stock; time was controlled at 2 hours; be controlled at 352 ± 2 ℃ near terminal temperature; drip and finish insulation 1 hour, logical nitrogen protection during insulation.Alkali fusion material is emitted the cooling back pulverize, stand-by.
In the reactor of 10000L, add the n-butyl acetate that 5200L feeds sulfur dioxide gas body weight gains 30%, under agitation add the alkali fusion material after pulverizing in batches, drip 450L water simultaneously, be warming up to 82 ± 2 ℃.Acidification reaction is kept after 2 hours and is finished.
Suction filtration, filter cake are used 300L n-butyl acetate and each washed twice of 300L water respectively, merging filtrate and n-butyl acetate washings, and wash water is applied mechanically.
Solvent distillation obtains crude phenols 1366Kg, and mass percent is 76.39%.
Embodiment 2
Add 1000Kg benzene (about 1136L) and the Powdered thenardite of 62Kg in the 5000L reactor, stir, slowly drip 65% oleum, control reaction temperature is no more than 45 ℃, adds the 1100Kg65% oleum in 20 minutes.Be warming up to 75 ℃, be incubated 10 minutes.
Add the Powdered thenardite of 95Kg in reaction product once more, control reaction temperature is no more than and drips sulfan 1070Kg under 165 ℃ of situations, adds in 40 minutes.Be warming up to 175 ℃ 2 ℃, be incubated 1 hour.
Add S-WAT 1800Kg in the 8000L reactor, water 2000Kg stirs, and is warming up to more than 80 ℃, and to wherein dripping above-mentioned sulfonated products, control reaction temperature is no more than 95 ℃.The pH value that dropwises back solution is added 30% sodium hydroxide and is regulated pH value to 8～9 below 4, keeps the temperature suction filtration, washes twice.Filtrate is treated alkali fusion usefulness.The sulfurous gas that produces in the reaction process feeds in the 5200L ether, treats that its weightening finish 25% back is stand-by.
Heating and melting in the alkali fusion reactor of the 10000L that the 3700Kg sodium hydrate solid is added; controlled temperature is at 330 ± 2 ℃; agitation condition drips in two sulfonated liquids and filtrated stock; time was controlled at about 2 hours; be controlled at 353 ± 2 ℃ near terminal temperature; drip and finish insulation 1 hour, logical nitrogen protection during insulation.Alkali fusion material is emitted the cooling back pulverize, stand-by.
In the reactor of 10000L, add the ether that 5200L feeds sulfur dioxide gas body weight gains 25%,, under agitation add the alkali fusion material after pulverizing in batches, drip 450L water simultaneously, be warming up to 50 ± 2 ℃.Reaction is kept after 1 hour and is finished.
Suction filtration, filter cake are used 300L ether and each washed twice of 300L water respectively, merging filtrate and ether washings, and wash water is applied mechanically.
Solvent distillation obtains crude phenols 1289Kg, and mass percent is 78.49%.
Embodiment 3
Add 1000Kg benzene (about 1136L) and the Powdered thenardite of 60Kg in the 5000L reactor, stir, slowly drip 65% oleum, control reaction temperature is no more than 45 ℃, adds the 1100Kg65% oleum in 20 minutes.Be warming up to 75 ℃, be incubated 10 minutes.
Add the Powdered thenardite of 95Kg in reaction product once more, control reaction temperature is no more than and drips sulfan 1070Kg under 165 ℃ of situations, adds in 40 minutes.Be warming up to 175 ℃ ± 2 ℃, be incubated 1 hour.
Add S-WAT 1800Kg in the 8000L reactor, water 2000Kg stirs, and is warming up to more than 80 ℃, and to wherein dripping above-mentioned sulfonated products, control reaction temperature is no more than 95 ℃.The pH value that dropwises back solution is added 30% sodium hydroxide and is regulated pH value to 8～9 below 4, keeps the temperature suction filtration, washes twice.Filtrate is treated alkali fusion usefulness.The sulfurous gas that produces in the reaction process feeds in the 5200L pimelinketone, treats that its weightening finish 28% back is stand-by.
Heating and melting in the alkali fusion reactor of the 10000L that the 3700Kg sodium hydrate solid is added; controlled temperature is at 325 ± 2 ℃; agitation condition drips in two sulfonated liquids and filtrated stock; time was controlled at about 2 hours; be controlled at 354 ± 2 ℃ near terminal temperature; drip and finish insulation 1 hour, logical nitrogen protection during insulation.Alkali fusion material is emitted the cooling back pulverize, stand-by.
In the reactor of 10000L, add the pimelinketone that 5200L feeds sulfur dioxide gas body weight gains 28%, under agitation add the alkali fusion material after pulverizing in batches, drip 450L water simultaneously, be warming up to 85 ℃.Acidification reaction is kept after 0.5 hour and is finished.
Suction filtration, filter cake are used 300L pimelinketone and each washed twice of 300L water respectively, merging filtrate and pimelinketone washings, and wash water is applied mechanically.
Solvent distillation obtains crude phenols 1307Kg, and mass percent is 73.87%.
Embodiment 4
Add 1000Kg benzene (about 1136L) and the Powdered thenardite of 60Kg in the 5000L reactor, stir, slowly drip 65% oleum, control reaction temperature is no more than 45 ℃, adds the 1100Kg65% oleum in 20 minutes.Be warming up to 75 ℃, be incubated 10 minutes.
Add the Powdered thenardite of 95Kg in reaction product once more, control reaction temperature is no more than and drips sulfan 1070Kg under 165 ℃ of situations, adds in 40 minutes.Be warming up to 175 ℃ ± 2 ℃, be incubated 1 hour.
Add S-WAT 1800Kg in the 8000L reactor, water 2000Kg stirs, and is warming up to more than 80 ℃, and to wherein dripping above-mentioned sulfonated products, control reaction temperature is no more than 95 ℃.The pH value that dropwises back solution is added 30% sodium hydroxide and is regulated pH value to 8～9 below 4, keeps the temperature suction filtration, washes twice.Filtrate is treated alkali fusion usefulness.The sulfurous gas that produces in the reaction process feeds in the 5200L propyl carbinol, treats that its weightening finish 30% back is stand-by.
Heating and melting in the alkali fusion reactor of the 10000L that the 3700Kg sodium hydrate solid is added; controlled temperature is at 325 ± 2 ℃; agitation condition drips in two sulfonated liquids and filtrated stock; time was controlled at about 2 hours; be controlled at 354 ± 2 ℃ near terminal temperature; drip and finish insulation 1 hour, logical nitrogen protection during insulation.Alkali fusion material is emitted the cooling back pulverize, stand-by.
In the reactor of 10000L, add the propyl carbinol that 5200L feeds sulfur dioxide gas body weight gains 30%, under agitation add the alkali fusion material after pulverizing in batches, drip 450L water simultaneously, be warming up to 85 ℃.Acidification reaction is kept after 1.5 hours and is finished.
Suction filtration, filter cake are used 300L propyl carbinol and each washed twice of 300L water respectively, merging filtrate and propyl carbinol washings, and wash water is applied mechanically.
Solvent distillation obtains crude phenols 1321Kg, and mass percent is 74.87%.
Embodiment 5
Add 1000Kg benzene (about 1136L) and the Powdered thenardite of 60Kg in the 5000L reactor, stir, slowly drip 65% oleum, control reaction temperature is no more than 45 ℃, adds the 1100Kg65% oleum in 20 minutes.Be warming up to 75 ℃, be incubated 10 minutes.
Add the Powdered thenardite of 95Kg in reaction product once more, control reaction temperature is no more than and drips sulfan 1070Kg under 165 ℃ of situations, adds in 40 minutes.Be warming up to 175 ℃ ± 2 ℃, be incubated 1 hour.
Add S-WAT 1800Kg in the 8000L reactor, water 2000Kg stirs, and is warming up to more than 80 ℃, and to wherein dripping above-mentioned sulfonated products, control reaction temperature is no more than 95 ℃.The pH value that dropwises back solution is added 30% sodium hydroxide and is regulated pH value to 8～9 below 4, keeps the temperature suction filtration, washes twice.Filtrate is treated alkali fusion usefulness.The sulfurous gas that produces in the reaction process feeds in the 5200L isopropyl ether, treats that its weightening finish 30% back is stand-by.
Heating and melting in the alkali fusion reactor of the 10000L that the 3700Kg sodium hydrate solid is added; controlled temperature is at 325 ± 2 ℃; agitation condition drips in two sulfonated liquids and filtrated stock; time was controlled at about 2 hours; be controlled at 354 ± 2 ℃ near terminal temperature; drip and finish insulation 1 hour, logical nitrogen protection during insulation.Alkali fusion material is emitted the cooling back pulverize, stand-by.
In the reactor of 10000L, add the isopropyl ether that 5200L feeds sulfur dioxide gas body weight gains 30%, under agitation add the alkali fusion material after pulverizing in batches, drip 450L water simultaneously, be warming up to 60 ℃.Acidification reaction is kept after 0.8 hour and is finished.
Suction filtration, filter cake are used 300L isopropyl ether and each washed twice of 300L water respectively, merging filtrate and isopropyl ether washings, and wash water is applied mechanically.
Solvent distillation obtains crude phenols 1321Kg, and mass percent is 74.87%.
Embodiment 6
Add 1000Kg benzene (about 1136L) and the Powdered thenardite of 60Kg in the 5000L reactor, stir, slowly drip 65% oleum, control reaction temperature is no more than 45 ℃, adds the 1100Kg65% oleum in 20 minutes.Be warming up to 75 ℃, be incubated 10 minutes.
Add the Powdered thenardite of 95Kg in reaction product once more, control reaction temperature is no more than and drips sulfan 1070Kg under 165 ℃ of situations, adds in 40 minutes.Be warming up to 175 ℃ ± 2 ℃, be incubated 1 hour.
Add S-WAT 1800Kg in the 8000L reactor, water 2000Kg stirs, and is warming up to more than 80 ℃, and to wherein dripping above-mentioned sulfonated products, control reaction temperature is no more than 95 ℃.The pH value that dropwises back solution is added 30% sodium hydroxide and is regulated pH value to 8～9 below 4, keeps the temperature suction filtration, washes twice.Filtrate is treated alkali fusion usefulness.The sulfurous gas that produces in the reaction process feeds in the 5200L hexone, treats that its weightening finish 30% back is stand-by.
Heating and melting in the alkali fusion reactor of the 10000L that the 3700Kg sodium hydrate solid is added; controlled temperature is at 325 ± 2 ℃; agitation condition drips in two sulfonated liquids and filtrated stock; time was controlled at about 2 hours; be controlled at 354 ± 2 ℃ near terminal temperature; drip and finish insulation 1 hour, logical nitrogen protection during insulation.Alkali fusion material is emitted the cooling back pulverize, stand-by.
In the reactor of 10000L, add the hexone that 5200L feeds sulfur dioxide gas body weight gains 30%, under agitation add the alkali fusion material after pulverizing in batches, drip 450L water simultaneously, be warming up to 70 ℃.Acidification reaction is kept after 1.7 hours and is finished.
Suction filtration, filter cake are used 300L hexone and each washed twice of 300L water respectively, merging filtrate and hexone washings, and wash water is applied mechanically.
Solvent distillation obtains crude phenols 1350Kg, and mass percent is 76.87%.
Claims (8)
1. production process for resorcinol, be raw material with benzene through sulfonation, in and operation, the sulfurous gas that produces in the neutralization reaction step feeds in the extraction solvent, treats that its weightening finish 25～30% is as the acidizing extraction solvent, the product of neutralization reaction is pulverized alkali fusion material cooling back behind alkali fusion; In reactor, add the acidizing extraction solvent, under agitation add the alkali fusion material after pulverizing in batches, drip water simultaneously, be warming up to 50～85 ℃, acidification reaction 0.5～2h, reaction product prepares Resorcinol through separation, filtration, distillation process.
2. production process for resorcinol according to claim 1 is characterized in that: described extraction solvent is selected from any one in n-butyl acetate, propyl carbinol, ether, isopropyl ether, pimelinketone or the hexone.
3. production process for resorcinol according to claim 2 is characterized in that: described extraction solvent is a n-butyl acetate, and the acidification reaction temperature is 82 ℃.
4. production process for resorcinol according to claim 2 is characterized in that: described extraction solvent is a propyl carbinol, and the acidification reaction temperature is 80 ℃.
5. production process for resorcinol according to claim 2 is characterized in that: described extraction solvent is an ether, and the acidification reaction temperature is 50 ℃.
6. production process for resorcinol according to claim 2 is characterized in that: described extraction solvent is an isopropyl ether, and the acidification reaction temperature is 60 ℃.
7. production process for resorcinol according to claim 2 is characterized in that: described extraction solvent is a pimelinketone, and the acidification reaction temperature is 85 ℃.
8. production process for resorcinol according to claim 2 is characterized in that: described extraction solvent is a hexone, and the acidification reaction temperature is 70 ℃.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102329253A (en) * | 2011-03-22 | 2012-01-25 | 江苏中丹集团股份有限公司 | Reaction apparatus for resorcinol neutralization reaction section and reaction technology thereof |
| CN108467338A (en) * | 2018-03-16 | 2018-08-31 | 苏州富博宏新材料科技有限公司 | A kind of process for cleanly preparing of resorcinol |
| CN111018676A (en) * | 2019-12-11 | 2020-04-17 | 乌海时联环保科技有限责任公司 | Method for preventing resorcinol from discoloring |
| CN111217677A (en) * | 2020-02-26 | 2020-06-02 | 山东创蓝垚石环保技术有限公司 | Method for producing resorcinol by material recycling and pressurized alkali fusion |
| CN111362780A (en) * | 2020-04-21 | 2020-07-03 | 哈密盛典科技有限公司 | Method for producing resorcinol by using sulfur trioxide |
| CN113929561A (en) * | 2020-06-29 | 2022-01-14 | 王兴路 | Alkali fusion method for preparing phenolic compound |
| CN114149306A (en) * | 2021-12-09 | 2022-03-08 | 青岛科技大学 | Synthesis process of resorcinol |
-
2008
- 2008-06-25 CN CN200810050151A patent/CN101613257A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102329253A (en) * | 2011-03-22 | 2012-01-25 | 江苏中丹集团股份有限公司 | Reaction apparatus for resorcinol neutralization reaction section and reaction technology thereof |
| CN102329253B (en) * | 2011-03-22 | 2013-10-30 | 江苏中丹集团股份有限公司 | Reaction apparatus for resorcinol neutralization reaction section and reaction technology thereof |
| CN108467338A (en) * | 2018-03-16 | 2018-08-31 | 苏州富博宏新材料科技有限公司 | A kind of process for cleanly preparing of resorcinol |
| CN111018676A (en) * | 2019-12-11 | 2020-04-17 | 乌海时联环保科技有限责任公司 | Method for preventing resorcinol from discoloring |
| CN111217677A (en) * | 2020-02-26 | 2020-06-02 | 山东创蓝垚石环保技术有限公司 | Method for producing resorcinol by material recycling and pressurized alkali fusion |
| CN111362780A (en) * | 2020-04-21 | 2020-07-03 | 哈密盛典科技有限公司 | Method for producing resorcinol by using sulfur trioxide |
| CN111362780B (en) * | 2020-04-21 | 2022-12-27 | 哈密盛典科技有限公司 | Method for producing resorcinol by using sulfur trioxide |
| CN113929561A (en) * | 2020-06-29 | 2022-01-14 | 王兴路 | Alkali fusion method for preparing phenolic compound |
| CN114149306A (en) * | 2021-12-09 | 2022-03-08 | 青岛科技大学 | Synthesis process of resorcinol |
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