CN101402552A - Method for producing m-cresol with direct hydrolyzation - Google Patents

Method for producing m-cresol with direct hydrolyzation Download PDF

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Publication number
CN101402552A
CN101402552A CNA2008102351007A CN200810235100A CN101402552A CN 101402552 A CN101402552 A CN 101402552A CN A2008102351007 A CNA2008102351007 A CN A2008102351007A CN 200810235100 A CN200810235100 A CN 200810235100A CN 101402552 A CN101402552 A CN 101402552A
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Prior art keywords
meta
cresol
extraction
aminotoluene
hydrolysis
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CN101402552B (en
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王武谦
刘伯军
许如海
杨崇高
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JIANGSU KESHENG CHEMICAL MACHINERY CO Ltd
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JIANGSU KESHENG CHEMICAL MACHINERY CO Ltd
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Abstract

The invention discloses a method for producing resordinol through direct hydrolysis. The method comprises the following steps: adding sulphuric acid or hydrochloric acid with certain concentration and meta-toluidine respectively according to a proportion into a blending pot so as to form meta-toluidine sulphate or meta-toluidine hydrochloride; sending the meta-toluidine sulphate or meta-toluidine hydrochloride aqueous solution from the blending pot into a high-pressure kettle; controlling the reaction temperature; carrying out the hydrolysis of the meta-toluidine sulphate or the meta-toluidine hydrochloride; recovering part of water in the hydrolysate through flash evaporation for blending; neutralizing the hydrolysate through ammonia spirit or caustic alkali aqueous solution till reaching a PH value of 3 to 5; carrying out organic extraction on the hydrolysate; and then recovering the extractant and refining coarse resordinol. The method adopts only one-step hydrolysis, thereby greatly reducing the dosage of sulphuric acid, and not using sodium nitrite. The concentration of the dilute sulfuric acid generated in the reaction process is lower than 2 percent. The method has the advantages that the cost of neutralizing the dilute acid is low, and the environmental pollution is also low.

Description

The direct hydrolysis method is produced the method for meta-cresol
Technical field
The invention belongs to the meta-cresol technical field of producing, more particularly relate to the method that the direct hydrolysis method is produced meta-cresol.
Background technology
Meta-cresol is the important chemical intermediate, mainly as pesticide intermediate, produces sterilant Sumithion, Tiguvon, meta-tolyl-N-methylcarbamate (MTMC), Permanone, also is the intermediate of color film, resin, softening agent and spices.
The domestic main employing meta-aminotoluene diazotization hydrolysis method of meta-cresol is carried out.This method normally is dissolved in meta-aminotoluene in the sulphuric acid soln, forms diazonium salt by dripping sodium nitrite solution, and diazonium salt is hydrolysis generation meta-cresol under acidic conditions again.The shortcoming of this method is: need the reaction of two steps to generate meta-cresol, product yield is low, and generally below 85%, total recovery is about 80% for the synthetic yield; There is the danger of easy decomposition explosion in the intermediates diazonium salt.Consume a large amount of sulfuric acid in diazotization reaction and hydrolysis reaction step, and the sulfuric acid concentration that generates is low, sulfuric acid concentration reclaims difficulty between 30-40%, and with the cost height, environmental pollution is serious in the diluted acid; Also to consume Sodium Nitrite simultaneously.
Summary of the invention
Purpose of the present invention just is to overcome above-mentioned shortcoming and defect, provide a kind of direct hydrolysis method to produce the method for meta-cresol, this method one one-step hydrolysis, a large amount of vitriolic consumptions that reduce, do not need to use Sodium Nitrite, the dilute sulphuric acid concentration that produces in the reaction process is lower than 2%, and low with cost in the diluted acid, environmental pollution is little.
Technical solution of the present invention is: add in the ingredients pot respectively certain density sulfuric acid or hydrochloric acid and meta-aminotoluene in proportion, form meta-aminotoluene vitriol or meta-aminotoluene hydrochloride, the meta-aminotoluene vitriol that comes out from ingredients pot or the meta-aminotoluene hydrochloride aqueous solution are delivered in the autoclave, control reaction temperature and pressure, meta-aminotoluene vitriol or the hydrolysis of meta-aminotoluene hydrochloride, hydrolyzed solution uses for batching by flash distillation recovery part water, by carrying out the recovery of extraction agent and making with extra care of product behind the organic solvent extracting taking-up meta-cresol.
The present invention specifically may further comprise the steps:
(1) batching is that 1-22% sulfuric acid or concentration are that 0.38-7.5% hydrochloric acid and concentration are that the 1-20% meta-aminotoluene aqueous solution mixes under whipped state with concentration, forms the meta-aminotoluene vitriol or the meta-aminotoluene hydrochloride aqueous solution;
(2) hydrolysis, with above-mentioned meta-aminotoluene vitriol or the meta-aminotoluene hydrochloride aqueous solution intermittently or deliver to continuously in the autoclave, hydrolysis reaction under temperature 200-280 ℃ condition generates meta-cresol and monoammonium sulfate or aqueous ammonium chloride solution;
(3) flash distillation or distillation dehydration, by flash distillation or distillation, recovery part water is used for (1) step batching with the hydrolyzed solution in the above-mentioned autoclave;
(4) neutralization, dropping ammonia or caustic-alkali aqueous solution in the still liquid behind above-mentioned recovery part water are adjusted to 3-5 with the pH value of still liquid;
(5) extraction, the still liquid after the above-mentioned neutralization extracts wherein meta-cresol with benzene, toluene or N-BUTYL ACETATE; The water that water after the extraction distills out wherein goes on foot batching usefulness for (1), and distillation residue are monoammonium sulfate or ammonium chloride, can make fertilizer and use;
(6) extraction agent reclaims, and the extraction phase after the above-mentioned extraction reclaims extraction agent by rectifying and uses for the extraction of (5) step;
(7) refining, the thick meta-cresol pressure 0.006Mpa rectifying behind the above-mentioned recovery extraction agent is collected cut for temperature 105-115 ℃ and is got the meta-cresol finished product.
Ultimate principle of the present invention is: aromatic amine and sulfuric acid or hydrochloric acid generate salt, and the sulfuric acid of aromatic amine or hydrochloride are hydrolyzed into phenol under High Temperature High Pressure; According to meta-cresol certain solubleness is arranged in water,, adopt the aqueous solution of organic solvent extraction meta-cresol in order to improve product yield and to reduce and pollute.
The present invention has the following advantages: 1, product yield height, and product yield is much higher than the diazotization hydrolysis process, and average yield is greater than 90%; 2, the sulfuric acid consumption is few, compares with traditional diazotization hydrolysis process, and the sulfuric acid consumption is saved more than 60%; 3, without Sodium Nitrite; 4, there are not dangerous middle work in-process, safe; 5, the dilute sulphuric acid concentration of Sheng Chenging is low, in and alkali needed few, in the sewage and cost low, environmental pollution is little.
Description of drawings
Fig. 1 is a technological process block-diagram of the present invention;
Embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail.Should be understood that these examples just in order to demonstrate the invention, but not limit the scope of the invention by any way.
Embodiment 1: produce meta-cresol according to following steps:
(1) batching is that 1% sulfuric acid and content are that 1% the meta-aminotoluene aqueous solution adds in the autoclave with content, mixes under whipped state;
(2) hydrolysis stops to stir and heating up, and hydrolysis reaction is 8 hours under 220 ℃ of conditions, generates the meta-cresol and the monoammonium sulfate aqueous solution;
(3) flash distillation is carried out atmospheric flashing with said hydrolyzed liquid, and recovery part water uses for (1) step batching;
(4) neutralization, dropping ammonia solution in reactor is transferred to 3 with the pH value;
(5) extraction extracts wherein meta-cresol with the still liquid after the neutralization with benzene; The water that water after the extraction distills out wherein goes on foot batching usefulness for (1), and distillation residue are monoammonium sulfate, can make fertilizer and use;
(6) extraction agent reclaims, and the extraction phase after the above-mentioned extraction is carried out rectifying under normal pressure, reclaims extraction agent benzene and uses for the extraction of (5) step;
(7) refining, the thick meta-cresol pressure 0.006Mpa rectifying behind the above-mentioned recovery extraction agent, tower top temperature is collected cut for 105 ℃, and the yield of meta-cresol is 90.57%
Embodiment 2: produce meta-cresol according to following steps:
(1) batching is that 5% sulfuric acid and content are that 5% the meta-aminotoluene aqueous solution adds in the autoclave with content, mixes under whipped state;
(2) hydrolysis stops to stir and heating up, and hydrolysis reaction is 8 hours under 200 ℃ of conditions, generates the meta-cresol and the monoammonium sulfate aqueous solution;
(3) flash distillation is carried out atmospheric flashing with said hydrolyzed liquid, and recovery part water uses for (1) step batching;
(4) neutralization, dropping ammonia solution in reactor is with pH value modulation 4;
(5) extraction extracts wherein meta-cresol with the still liquid after the neutralization with toluene; The water that water after the extraction distills out wherein goes on foot batching usefulness for (1), and distillation residue are monoammonium sulfate, can make fertilizer and use;
(6) extraction agent reclaims, and the extraction phase after the above-mentioned extraction is carried out rectifying under normal pressure, reclaims extraction agent benzene and uses for the extraction of (5) step;
(7) refining, the thick meta-cresol pressure 0.006Mpa rectifying behind the above-mentioned recovery extraction agent, tower top temperature is collected cut for 110 ℃, and the yield of meta-cresol is 91.20%
Embodiment 3: produce meta-cresol according to following steps:
(1) batching is that 10% sulfuric acid and content are that 10% the meta-aminotoluene aqueous solution adds in the autoclave with content, mixes under whipped state;
(2) hydrolysis stops to stir and heating up, and hydrolysis reaction is 8 hours under 250 ℃ of conditions, generates the meta-cresol and the monoammonium sulfate aqueous solution;
(3) flash distillation is carried out atmospheric flashing with said hydrolyzed liquid, and recovery part water uses for (1) step batching;
(4) neutralization, the dropping sodium aqueous solution in reactor is with pH value modulation 5;
(5) extraction extracts wherein meta-cresol with the still liquid after the neutralization with N-BUTYL ACETATE; The water that water after the extraction distills out wherein goes on foot batching usefulness for (1), and distillation residue are monoammonium sulfate, can make fertilizer and use;
(6) extraction agent reclaims, and extraction phase after the above-mentioned extraction is carried out rectifying under normal pressure, reclaims extraction agent benzene and uses for the extraction of (5) step;
(7) refining, the thick meta-cresol pressure 0.006Mpa rectifying behind the above-mentioned recovery extraction agent, tower top temperature is collected cut for 115 ℃, and the yield of meta-cresol is 90.25%
Embodiment 4: produce meta-cresol according to following steps:
(1) batching is that 22% sulfuric acid and content are that 20% the meta-aminotoluene aqueous solution adds in the autoclave with content, mixes under whipped state;
(2) hydrolysis stops to stir and heating up, and hydrolysis reaction is 8 hours under 280 ℃ of conditions, generates the meta-cresol and the monoammonium sulfate aqueous solution;
(3) flash distillation is carried out atmospheric flashing with said hydrolyzed liquid, and recovery part water uses for (1) step batching;
(4) neutralization, dropping ammonia solution in reactor is with pH value modulation 5;
(5) extraction extracts wherein meta-cresol with the still liquid after the neutralization with benzene; The water that water after the extraction distills out wherein goes on foot batching usefulness for (1), and distillation residue are monoammonium sulfate, can make fertilizer and use;
(6) extraction agent reclaims, and extraction phase after the above-mentioned extraction is carried out rectifying under normal pressure, reclaims extraction agent benzene and uses for the extraction of (5) step;
(7) refining, the thick meta-cresol pressure 0.006Mpa rectifying behind the recovery extraction agent, tower top temperature is collected cut for 105 ℃, and the yield of meta-cresol is 88.36%
Embodiment 5: produce meta-cresol according to following steps:
(1) batching in ingredients pot is that 0.38% hydrochloric acid and content are that 1% the meta-aminotoluene aqueous solution mixes under whipped state with content;
(2) hydrolysis is delivered to the above-mentioned meta-aminotoluene hydrochloride aqueous solution in the autoclave continuously, is under 200 ℃ the condition in temperature, and the reaction that is hydrolyzed generates meta-cresol and aqueous ammonium chloride solution;
(3) flash distillation is carried out atmospheric flashing with said hydrolyzed liquid, and recovery part water uses for (1) step batching;
(4) neutralization, dropping ammonia solution in the hydrolyzed solution after above-mentioned flash distillation is with pH value modulation 3;
(5) extraction extracts wherein meta-cresol with the still liquid after the neutralization with benzene; The water that water after the extraction distills out wherein goes on foot batching usefulness for (1), and distillation residue are ammonium chloride, can make fertilizer and use;
(6) extraction agent reclaims, and extraction phase after the above-mentioned extraction is carried out rectifying under normal pressure, reclaims extraction agent benzene and uses for the extraction of (5) step;
(7) refining, the thick meta-cresol pressure 0.006Mpa rectifying behind the above-mentioned recovery extraction agent, tower top temperature is collected cut for 110 ℃, and the yield of meta-cresol is 90.85%
Embodiment 6: produce meta-cresol according to following steps:
(1) batching in ingredients pot is that 1.8% hydrochloric acid and content are that 5% the meta-aminotoluene aqueous solution mixes under whipped state with content;
(2) hydrolysis is delivered to the above-mentioned meta-aminotoluene hydrochloride aqueous solution in the autoclave continuously, is under 220 ℃ the condition in temperature, and the reaction that is hydrolyzed generates meta-cresol and aqueous ammonium chloride solution;
(3) flash distillation is carried out atmospheric flashing with said hydrolyzed liquid, and recovery part water uses for (1) step batching;
(4) neutralization, dropping ammonia solution in the hydrolyzed solution after above-mentioned flash distillation is with pH value modulation 4;
(5) extraction extracts wherein meta-cresol with the still liquid after the neutralization with toluene; The water that water after the extraction distills out wherein goes on foot batching usefulness for (1), and distillation residue are ammonium chloride, can make fertilizer and use;
(6) extraction agent reclaims, and the extraction phase after the above-mentioned extraction is carried out rectifying under normal pressure, reclaims extraction agent toluene and uses for the extraction of (5) step;
(7) refining, the thick meta-cresol pressure 0.006Mpa rectifying behind the above-mentioned recovery extraction agent, tower top temperature is collected cut for 115 ℃, and the yield of meta-cresol is 90.75%
Embodiment 7: produce meta-cresol according to following steps:
(1) batching in ingredients pot is that 3.7% hydrochloric acid and content are that 10% the meta-aminotoluene aqueous solution mixes under whipped state with content;
(2) hydrolysis is delivered to the above-mentioned meta-aminotoluene hydrochloride aqueous solution in the autoclave continuously, is under 250 ℃ the condition in temperature, and the reaction that is hydrolyzed generates meta-cresol and aqueous ammonium chloride solution;
(3) flash distillation is carried out atmospheric flashing recovery part water with said hydrolyzed liquid, uses for (1) step batching;
(4) neutralization, dropping ammonia solution in the hydrolyzed solution after above-mentioned flash distillation is with pH value modulation 5;
(5) extraction extracts wherein meta-cresol with the still liquid after the neutralization with N-BUTYL ACETATE; The water that water after the extraction distills out wherein goes on foot batching usefulness for (1), and distillation residue are ammonium chloride, can make fertilizer and use;
(6) extraction agent reclaims, and the extraction phase after the above-mentioned extraction is carried out rectifying under reduced pressure, reclaims the extraction agent N-BUTYL ACETATE and uses for the extraction of (5) step;
(7) refining, the thick meta-cresol pressure 0.006Mpa rectifying behind the above-mentioned recovery extraction agent, tower top temperature is collected cut for 105 ℃, and the yield of meta-cresol is 91.85%
Embodiment 8: produce meta-cresol according to following steps:
(1) batching is that 5.6% hydrochloric acid and content are that 15% the meta-aminotoluene aqueous solution adds in the autoclave with content, mixes under whipped state;
(2) hydrolysis stops to stir and heating up, and hydrolysis reaction is 8 hours under 260 ℃ of conditions, generates meta-cresol and aqueous ammonium chloride solution;
(3) flash distillation is carried out atmospheric flashing with said hydrolyzed liquid, and recovery part water uses for (1) step batching;
(4) neutralization, dropping ammonia solution in reactor is with pH value modulation 3;
(5) extraction extracts wherein meta-cresol with the still liquid after the neutralization with benzene; The water that water after the extraction distills out wherein goes on foot batching usefulness for (1), and distillation residue are ammonium chloride, can make fertilizer and use;
(6) extraction agent reclaims, and the extraction phase after the above-mentioned extraction is carried out rectifying under normal pressure, reclaims extraction agent benzene and uses for the extraction of (5) step;
(7) refining, the thick meta-cresol pressure 0.006Mpa rectifying behind the above-mentioned recovery extraction agent, tower top temperature is collected cut for 110 ℃, and the yield of meta-cresol is 90.75%
Embodiment 9: produce meta-cresol according to following steps:
(1) batching is that 7.5% hydrochloric acid and content are that 20% the meta-aminotoluene aqueous solution adds in the autoclave with content, mixes under whipped state;
(2) hydrolysis stops to stir and heating up, and hydrolysis reaction is 8 hours under 280 ℃ of conditions, generates meta-cresol and aqueous ammonium chloride solution;
(3) flash distillation is carried out atmospheric flashing with said hydrolyzed liquid, and recovery part water uses for (1) step batching;
(4) neutralization, the dropping sodium aqueous solution in reactor is with pH value modulation 4;
(5) extraction extracts wherein meta-cresol with the still liquid after the neutralization with toluene; The water that water after the extraction distills out wherein goes on foot batching usefulness for (1), and distillation residue are ammonium chloride, can make fertilizer and use;
(6) extraction agent reclaims, and the extraction phase after the above-mentioned extraction is carried out rectifying under condition of normal pressure, reclaims extraction agent benzene and uses for the extraction of (5) step;
(7) refining, the thick meta-cresol pressure 0.006Mpa rectifying behind the above-mentioned recovery extraction agent, tower top temperature is collected cut for 115 ℃, and the yield of meta-cresol is 91.20%
Embodiment 10: produce meta-cresol according to following steps:
(1) batching is that 7.5% hydrochloric acid and content are that 20% the meta-aminotoluene aqueous solution adds in the autoclave with content, mixes under whipped state;
(2) hydrolysis stops to stir and heating up, and hydrolysis reaction is 8 hours under 280 ℃ of conditions, generates meta-cresol and aqueous ammonium chloride solution;
(3) flash distillation is carried out atmospheric flashing with said hydrolyzed liquid, and recovery part water uses for (1) step batching;
(4) neutralization, dropping ammonia solution in reactor is with pH value modulation 5;
(5) extraction extracts wherein meta-cresol with the still liquid after the neutralization with N-BUTYL ACETATE; The water that water after the extraction distills out wherein goes on foot batching usefulness for (1), and distillation residue are ammonium chloride, can make fertilizer and use;
(6) extraction agent reclaims, and the extraction phase of above-mentioned extraction is carried out rectifying under condition of normal pressure, reclaims extraction agent benzene and uses for the extraction of (5) step;
(7) refining, the thick meta-cresol pressure 0.006Mpa rectifying behind the above-mentioned recovery extraction agent, tower top temperature is collected cut for 105 ℃, and the yield of meta-cresol is 89.20%.

Claims (2)

1. the direct hydrolysis method is produced the method for meta-cresol, it is characterized in that: add in the ingredients pot respectively certain density sulfuric acid or hydrochloric acid and meta-aminotoluene in proportion, form meta-aminotoluene vitriol or meta-aminotoluene hydrochloride, the meta-aminotoluene vitriol that comes out from ingredients pot or the meta-aminotoluene hydrochloride aqueous solution are delivered in the autoclave, control reaction temperature and pressure, meta-aminotoluene vitriol or the hydrolysis of meta-aminotoluene hydrochloride, hydrolyzed solution uses for batching by flash distillation recovery part water, by carrying out the recovery of extraction agent and making with extra care of product behind the organic solvent extracting taking-up meta-cresol.
2. direct hydrolysis method according to claim 1 is produced the method for meta-cresol, it is characterized in that specifically may further comprise the steps:
(1) batching is that 1-22% sulfuric acid or concentration are that 0.38-7.5% hydrochloric acid and concentration are that the 1-20% meta-aminotoluene aqueous solution mixes under whipped state with concentration, forms the meta-aminotoluene sulfate solution;
(2) hydrolysis, with above-mentioned meta-aminotoluene vitriol or the meta-aminotoluene hydrochloride aqueous solution intermittently or deliver to continuously in the autoclave, hydrolysis reaction under temperature 200-280 ℃ condition generates meta-cresol and monoammonium sulfate or aqueous ammonium chloride solution;
(3) flash distillation or distillation dehydration, by flash distillation or distillation, recovery part water is used for (1) step batching with the hydrolyzed solution in the above-mentioned autoclave;
(4) neutralization, dropping ammonia or caustic-alkali aqueous solution in the still liquid behind above-mentioned recovery part water are adjusted to 3-5 with the pH value of still liquid;
(5) extraction, the still liquid after the above-mentioned neutralization extracts wherein meta-cresol with benzene, toluene or N-BUTYL ACETATE; The water that water after the extraction distills out wherein goes on foot batching usefulness for (1), and distillation residue are monoammonium sulfate or ammonium chloride, can make fertilizer and use;
(6) extraction agent reclaims, and the extraction phase after the above-mentioned extraction reclaims extraction agent by rectifying and uses for the extraction of (5) step;
(7) refining, the thick meta-cresol pressure 0.006Mpa rectifying behind the above-mentioned recovery extraction agent is collected cut for temperature 105-115 ℃ and is got the meta-cresol finished product.
CN2008102351007A 2008-11-13 2008-11-13 Method for producing m-cresol with direct hydrolyzation Active CN101402552B (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101941890A (en) * 2010-09-02 2011-01-12 江苏淮河化工有限公司 Method and device for preparing metacresol
CN102838457A (en) * 2012-09-20 2012-12-26 山东潍坊润丰化工有限公司 Synthesis method of 2, 5-dichlorophenol
CN103044205A (en) * 2012-12-08 2013-04-17 浙江鼎龙科技有限公司 Preparation method of 3-methyl-4-isopropylphenol

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1223565C (en) * 2003-01-06 2005-10-19 唐师法 Preparation process of meta-cresol
CN101125800A (en) * 2007-09-28 2008-02-20 中北大学 Technique for preparing m-cresol
CN101591223A (en) * 2008-05-30 2009-12-02 南京理工大学 The direct hydrolysis meta-aminotoluene prepares the method for meta-cresol

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101941890A (en) * 2010-09-02 2011-01-12 江苏淮河化工有限公司 Method and device for preparing metacresol
CN101941890B (en) * 2010-09-02 2014-06-11 江苏淮河化工有限公司 Method and device for preparing metacresol
CN102838457A (en) * 2012-09-20 2012-12-26 山东潍坊润丰化工有限公司 Synthesis method of 2, 5-dichlorophenol
CN103044205A (en) * 2012-12-08 2013-04-17 浙江鼎龙科技有限公司 Preparation method of 3-methyl-4-isopropylphenol

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