CN104341275A - Synthesis method for 2, 6-dihydroxytoluene - Google Patents
Synthesis method for 2, 6-dihydroxytoluene Download PDFInfo
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Abstract
The invention discloses a synthesis method for 2, 6-dihydroxytoluene. According to the method, the 2, 6-dihydroxytoluene is obtained from 3-chloro-2-methylaniline is used as raw materials through diazotization reaction, lanthanum phosphate catalysis hydrolysis, alkali dissolution and acidification. The synthesis method has the advantages that (1) the raw material resources are wide; (2) the process is simple, and the operation is easy; (3) active rear earth is used as catalysts, and the color and luster of products can be optimized; (4) the reaction conditions are relatively mild, and the safety factor is high; (5) the total yield is as high as more than 65 percent, the purity reaches more than 99.0 percent, in addition, solvents can be recovered and reused, and the energy-saving and emission-reduction effects are obvious.
Description
One technical field
The present invention relates to a kind of synthetic method of 2,6-orcin, belong to technical field of chemical material preparation.Present method is applicable to 3-chloro-2-methyl aniline for raw material, the occasion of synthesis 2,6-orcin.
Two background technologies
2,6-orcin is a kind of important fine-chemical intermediate, is widely used in the fields such as pigment, dyestuff, hair dye, synthetic resins, medicine, agricultural chemicals, photography.
At present, 2,6-orcin mainly contains following several synthetic method:
(1) be raw material high-pressure hydrogenation hydrolysis method with 2,6-dinitrotoluene (DNT).
This method is divided into two steps, first uses 2,6-dinitrotoluene (DNT) to carry out hydrogenation reaction under high-temperature and high-pressure conditions, then under acetate system, uses palladium. and carbon as catalyzer, then is hydrolyzed to obtain 2,6-orcins.But the method need acid and carry out under the condition of High Temperature High Pressure, and make equipment materials difficulty, the catalyzer of employing is expensive, makes the production cost of product increase, and the purity obtaining product is low, is not suitable for suitability for industrialized production simultaneously.
(2) be that raw material passes through CH with hydroresorcinol
3i or Mannich reaction introduces methyl dehydrogenation again in 2-position.
This circuit needs to carry out hydrogenation and dehydrogenation reaction in building-up process, and these two processes all need to use a large amount of palladium carbon catalysts, and reaction yield is low, makes product cost higher.
(3) Resorcinol methyl alcohol methylation reaction.
The method is that Resorcinol and methyl alcohol are at ammonium chloride. in the medium of methyl alcohol, obtain product through High Temperature High Pressure direct reaction.Reaction is carried out under the condition of high temperature, high pressure, and especially temperature of reaction is up to 530 DEG C, and this adds difficulty to the type selecting of equipment, and the yield of reaction is low, and the by product of generation is many, separation difficulty, is not suitable for the needs of suitability for industrialized production.
(4) Resorcinol methyl iodide methylation method.
The method is the industrial method used at present.Three reactions steps of this method all belong to classical reaction.The yield often walking product is also higher, but catalyst iodine methane is expensive, and belongs to hypertoxic raw material, and this makes the cost of product raise, and potential safety hazard is serious, causes the market competitiveness of target product not strong.
(5) resorcinol formaldehyde methylation method
This circuit and other several circuits contrast, and reactions steps is more, and total recovery is lower, complex manufacturing, actually operating difficulty.
(6) take pentanedioic acid as raw material
The catalyzer of this reaction is oil of mirbane and aluminum chloride.The acetic anhydride steam used in this route is poisonous, and this synthetic route more complicated, can produce more by product, be not easy to the separating-purifying of product, make post-processed also become relative sending out to mix, also comparatively serious to the pollution of environment, reaction conditions is difficult to control.
Three summary of the invention
The object of the invention is to selective reaction mild condition, safety coefficient be high, product yield is high, synthetic method that product purity is high.
The technical solution realizing the object of the invention is: a kind of synthetic method of 2,6-orcin, and with 3-chloro-2-methyl aniline for starting raw material, acidifying 4 step reaction molten through diazotization reaction, hydrolysis, alkali, obtains 2,6-orcin:
Step 1): diazotization reaction.In diazotization still, first sulfuric acid is mixed with 40% (mass percent) aqueous solution, starts to drip 3-chloro-2-methyl aniline, dropwise in 1.5-2h when being warming up to 90-95 DEG C, after insulation 1.0h, logical salt solution is cooled to less than 5 DEG C.Control temperature, at 0-5 DEG C, drips the sodium nitrite in aqueous solution that mass percent is 30% in 3-4h, and finish rear insulation 1.0h, it is for subsequent use that suction filtration obtains diazo liquid filtrate.
Step 2): hydrolysis.The mother liquid coming of water or recovery is injected in still, add active rare earth catalyst lanthanum orthophosphate, open and stir, at the uniform velocity drip the vitriol oil, the toluene extraction liquid of toluene or reextraction, be warming up to backflow, drip by step 1 in 3-4h) diazo liquid that obtains, lower the temperature after insulation 0.5h, leave standstill point water layer and an organic layer, a water layer part recycles as mother liquid coming, and remainingly put to waste water processing station after toluene reextraction, the toluene extraction liquid of reextraction can recycle; Organic layer need not dry directly be beaten to the molten still of alkali, be warming up to 60 DEG C, at the uniform velocity drip sheet alkali 11% (mass percent) aqueous solution and be about 1h, leave standstill point water layer and an organic layer, sodium phenolate solution water layer is placed in bucket, treat that high pressure feeds intake use, organic layer can recycle through the toluene of Distillation recovery.
Step 3): alkali is molten.Suction successively in autoclave: step 2) the sodium phenolate solution that obtains, mass percent 63.5% aqueous sodium hydroxide solution, sodium formiate, S-WAT, the cuprous chloride catalyst that sour water is washed.Heating, at 195 ~ 200 DEG C, still internal pressure is under 1.0 ~ 1.2Mpa condition, and insulation 1.5-2h, is then cooled to 100 DEG C and carries out suction filtration, elimination solid slag, unified collection.Filtrate is for subsequent use.
Step 4): acidifying.In advance hydrochloric acid and water being made into aqueous hydrochloric acid, step 3 according to 1: 1.2 ~ 1.3 ratios) filtrate that obtains enters in acidifying still, and in 0.5-1.0h, fast drop aqueous hydrochloric acid to pH value is 1.5-2.Be cooled to room temperature, suction filtration, extraction into ethyl acetate, saturated soda water washing is in neutral, and steam and add toluene, crystallisation by cooling except after ethyl acetate, centrifugation obtains crude product, obtains purified product after recrystallization decolouring.
The raw materials used ratio of the present invention is respectively:
Step 1): the mass percent of 3-chloro-2-methyl aniline, the vitriol oil, Sodium Nitrite is 1: 3.1 ~ 3.5: 0.49 ~ 0.53;
Step 2): the mass percent of toluene, the vitriol oil, catalyst P 1 is 1: 0.80 ~ 0.85: 0.014 ~ 0.021;
Step 3): the mass percent of sodium phenolate solution, cuprous chloride, S-WAT, sodium formiate is 1: 1.2 ~ 1.4: 1.6 ~ 1.8: 1.2 ~ 1.4;
Step 4): all drying processes all use homemade boiling drying equipment, dry product, often criticize 0.5h time of drying, solvent energy recovery at 40-50 DEG C.
According to the synthetic method of a kind of 2,6-orcins provided by the invention, its key problem in technology adopts 3-chloro-2-methyl aniline to be starting raw material, and, acidifying 4 step molten through diazotization reaction, hydrolysis, alkali is obtained by reacting target product;
According to the synthetic method of a kind of 2,6-orcins provided by the invention, wherein step 2) the 3-chloro-2-methyl phenol that generates not drying directly drip sodium phenolate processed throwing autoclave with alkali lye;
According to the synthetic method of a kind of 2,6-orcins provided by the invention, step 2) adopt active rare earth as catalyzer;
According to the synthetic method of a kind of 2,6-orcins provided by the invention, adopt homemade boiling drying equipment, save drying time and weight loss on drying effect is better.
Compared with prior art, its advantage is in the present invention: (1) raw material sources are extensive, the simple easy handling of (2) technique; (3) can optimizing product color and luster as catalyzer with active rare earth; (4) reaction conditions is relatively gentle, and safety coefficient is high; (5) total recovery is up to more than 65%, and purity reaches more than 99.0%; (6) adopt homemade boiling drying equipment, save drying time and weight loss on drying better effects if, and solvent can recovery, effects of energy saving and emission reduction is obvious.
Four embodiments
By the following examples in detail the present invention is described in detail, these embodiments are only clear open the present invention, not as limitation of the present invention.
Embodiment 1
Step 1): in 2000L doazo reaction still, add the aqueous sulfuric acid 1750kg that mass percent is 40%, steam heating, start when temperature rises to 90-95 DEG C at the uniform velocity to drip 3-chloro-2-methyl aniline 225kg, dropwise in 1.5-2h, insulation reaction 1.0h.Logical salt solution is cooled to less than 5 DEG C.Control temperature, at 0-5 DEG C, drips the sodium nitrite in aqueous solution 380kg that mass percent is 30% in 3-4h, and finish rear insulation 1.0h, it is for subsequent use that suction filtration obtains suction filtration diazo liquid.
Step 2): the mother liquid coming injecting 780kg water or recovery in hydrolysis kettle, add the active rare earth catalyst lanthanum orthophosphate of 10kg, open and stir, at the uniform velocity drip the 560kg vitriol oil, the toluene extraction liquid of 700kg toluene or reextraction, be warming up to backflow, step 1 is dripped in 3-4h) diazo liquid that obtains, lower the temperature after insulation 0.5h, leave standstill point water layer and an organic layer, water layer is got 780kg and is recycled as mother liquid coming, remainingly puts to waste water processing station after toluene reextraction, and the toluene extraction liquid of reextraction goes to hydrolysis kettle header tank and recycles; Organic layer is directly beaten to the molten still of alkali, be warming up to 60 DEG C, at the uniform velocity drip 675kg. sheet alkali 11% (mass percent) aqueous solution and be about 1h, leave standstill point water layer and an organic layer, sodium phenolate solution water layer is placed in bucket, treat that high pressure feeds intake use, organic layer can recycle as the toluene solvant of reextraction through the toluene of Distillation recovery.
Step 3): suction successively in autoclave: 550kg step 2) the sodium phenolate solution that obtains, 275kg mass percent 63.5% aqueous sodium hydroxide solution, 8kg sodium formiate, 10kg S-WAT, the cuprous chloride catalyst that 8kg sour water is washed.Heating, at 195 ~ 200 DEG C, still internal pressure is under 1.0 ~ 1.2Mpa condition, and insulation 1.5-2h, is then cooled to 100 DEG C and carries out suction filtration, elimination solid slag, unified collection.Filtrate is for subsequent use.
Step 4): in advance by 650kg hydrochloric acid and 800kg water wiring solution-forming, step 3) filtrate that obtains enters in acidifying still, and in 0.5-1.0h, fast drop aqueous hydrochloric acid to pH value is 1.5-2.Be cooled to room temperature, suction filtration, 800kg extraction into ethyl acetate, saturated soda water washing is in neutral, and steam and add 350kg toluene, crystallisation by cooling except after ethyl acetate, centrifugation obtains crude product, obtains purified product after recrystallization decolouring.Total recovery reaches more than 65%, and purity reaches more than 99.0%.
Embodiment 2
Step 1): in 2000L doazo reaction still, add the aqueous sulfuric acid 1969kg that mass percent is 40%, steam heating, start when temperature rises to 90-95 DEG C at the uniform velocity to drip 3-chloro-2-methyl aniline 225kg, dropwise in 1.5-2h, insulation reaction 1.0h.Logical salt solution is cooled to less than 5 DEG C.Control temperature, at 0-5 DEG C, drips the sodium nitrite in aqueous solution 390kg that mass percent is 30% in 3-4h, and finish rear insulation 1.0h, it is for subsequent use that suction filtration obtains suction filtration diazo liquid.
Step 2): in hydrolysis kettle, inject the mother liquid coming that 780kg reclaims, add the active rare earth catalyst lanthanum orthophosphate of 15kg, open and stir, at the uniform velocity drip the 600kg vitriol oil, the toluene extraction liquid of 700kg reextraction, be warming up to backflow, step 1 is dripped in 3-4h) diazo liquid that obtains, lower the temperature after insulation 0.5h, leave standstill point water layer and an organic layer, water layer is got 780kg and is recycled as mother liquid coming, remainingly puts to waste water processing station after toluene reextraction, and the toluene extraction liquid of reextraction goes to hydrolysis kettle header tank and recycles; Organic layer is directly beaten to the molten still of alkali, be warming up to 60 DEG C, at the uniform velocity drip 675kg sheet alkali 11% (mass percent) aqueous solution and be about 1h, leave standstill point water layer and an organic layer, sodium phenolate solution water layer is placed in bucket, treat that high pressure feeds intake use, organic layer can recycle as the toluene solvant of reextraction through the toluene of Distillation recovery.
Step 3): suction successively in autoclave: 570kg step 2) the sodium phenolate solution that obtains, 275kg mass percent 63.5% aqueous sodium hydroxide solution, 7kg sodium formiate, 9kg S-WAT, the cuprous chloride catalyst that 7kg sour water is washed.Heating, at 195 ~ 200 DEG C, still internal pressure is under 1.0 ~ 1.2Mpa condition, and insulation 1.5-2h, is then cooled to 100 DEG C and carries out suction filtration, elimination solid slag, unified collection.Filtrate is for subsequent use.
Step 4): in advance by 700kg hydrochloric acid and 900kg water wiring solution-forming, step 3) filtrate that obtains enters in acidifying still, and in 0.5-1.0h, fast drop aqueous hydrochloric acid to pH value is 1.5-2.Be cooled to room temperature, suction filtration, 800kg extraction into ethyl acetate, saturated soda water washing is in neutral, and steam and add 350kg toluene, crystallisation by cooling except after ethyl acetate, centrifugation obtains crude product, obtains purified product after recrystallization decolouring.Total recovery reaches more than 65%, and purity reaches more than 99.0%.
Embodiment 3
Step 1): in 2000L doazo reaction still, add the aqueous sulfuric acid 1850kg that mass percent is 40%, steam heating, start when temperature rises to 90-95 DEG C at the uniform velocity to drip 3-chloro-2-methyl aniline 225kg, dropwise in 1.5-2h, insulation reaction 1.0h.Logical salt solution is cooled to less than 5 DEG C.Control temperature, at 0-5 DEG C, drips the sodium nitrite in aqueous solution 385kg that mass percent is 30% in 3-4h, and finish rear insulation 1.0h, it is for subsequent use that suction filtration obtains suction filtration diazo liquid.
Step 2): in hydrolysis kettle, inject the mother liquid coming that 780kg reclaims, add the active rare earth catalyst lanthanum orthophosphate of 13kg, open and stir, at the uniform velocity drip the 560kg vitriol oil, the toluene extraction liquid of 700kg reextraction, be warming up to backflow, step 1 is dripped in 3-4h) diazo liquid that obtains, lower the temperature after insulation 0.5h, leave standstill point water layer and an organic layer, water layer is got 780kg and is recycled as mother liquid coming, remainingly puts to waste water processing station after toluene reextraction, and the toluene extraction liquid of reextraction goes to hydrolysis kettle header tank and recycles; Organic layer is directly beaten to the molten still of alkali, be warming up to 60 DEG C, at the uniform velocity drip 675kg sheet alkali 11% (mass percent) aqueous solution and be about 1h, leave standstill point water layer and an organic layer, sodium phenolate solution water layer is placed in bucket, treat that high pressure feeds intake use, organic layer can recycle as the toluene solvant of reextraction through the toluene of Distillation recovery.
Step 3): suction successively in autoclave: 560kg step 2) the sodium phenolate solution that obtains, 275kg mass percent 63.5% aqueous sodium hydroxide solution, 7.5kg sodium formiate, 9.5kg S-WAT, the cuprous chloride catalyst that 7.5kg sour water is washed.Heating, at 195 ~ 200 DEG C, still internal pressure is under 1.0 ~ 1.2Mpa condition, and insulation 1.5-2h, is then cooled to 100 DEG C and carries out suction filtration, elimination solid slag, unified collection.Filtrate is for subsequent use.
Step 4): in advance by 675kg hydrochloric acid and 850kg water wiring solution-forming, step 3) filtrate that obtains enters in acidifying still, and in 0.5-1.0h, fast drop aqueous hydrochloric acid to pH value is 1.5-2.Be cooled to room temperature, suction filtration, 800kg extraction into ethyl acetate, saturated soda water washing is in neutral, and steam and add 350kg toluene, crystallisation by cooling except after ethyl acetate, centrifugation obtains crude product, obtains purified product after recrystallization decolouring.Total recovery reaches more than 65%, and purity reaches more than 99.0%.
Claims (4)
1. the synthetic method of an orcin, is characterized in that: with 3-chloro-2-methyl aniline for starting raw material, acidifying 4 steps molten through diazotization reaction, hydrolysis, alkali, and obtain 2,6-orcin, synthesis step is as follows:
Step 1): in diazotization still, first sulfuric acid is mixed with 40% (mass percent) aqueous solution, start when being warming up to 90-95 DEG C to drip 3-chloro-2-methyl aniline, dropwise in 1.5-2h, after insulation 1.0h, logical salt solution is cooled to less than 5 DEG C, and control temperature, at 0-5 DEG C, drips the sodium nitrite in aqueous solution that mass percent is 30% in 3-4h, finish rear insulation 1.0h, it is for subsequent use that suction filtration obtains diazo liquid filtrate;
Wherein, the mass percent of 3-chloro-2-methyl aniline, the vitriol oil, Sodium Nitrite is 1: 3.1 ~ 3.5: 0.49 ~ 0.53;
Step 2): the mother liquid coming injecting water or recovery in still, add active rare earth catalyst lanthanum orthophosphate and open stirring, at the uniform velocity drip the vitriol oil, the toluene extraction liquid of toluene or reextraction, be warming up to backflow, drip by step 1 in 3-4h) diazo liquid that obtains, lower the temperature after insulation 0.5h, leave standstill point water layer and an organic layer, a water layer part recycles as mother liquid coming, remainingly put to waste water processing station after toluene reextraction, the toluene extraction liquid of reextraction can recycle; Organic layer need not dry directly be beaten to the molten still of alkali, be warming up to 60 DEG C, at the uniform velocity drip sheet alkali 11% (mass percent) aqueous solution and be about 1h, leave standstill point water layer and an organic layer, sodium phenolate solution water layer is placed in bucket, treat that high pressure feeds intake use, organic layer can recycle through the toluene of Distillation recovery;
Wherein, the mass percent of toluene, the vitriol oil, catalyzer lanthanum orthophosphate is 1: 0.80 ~ 0.85: 0.014 ~ 0.021;
Step 3): suction step 2 successively in autoclave) the washed cuprous chloride catalyst of the sodium phenolate solution, mass percent 63.5% aqueous sodium hydroxide solution, sodium formiate, S-WAT, the sour water that obtain, be warming up to 195 ~ 200 DEG C, still internal pressure is under 1.0 ~ 1.2Mpa condition, insulation 1.5-2h, then be cooled to 100 DEG C and carry out suction filtration, elimination solid slag, unified collection, filtrate is for subsequent use;
Wherein, the mass percent of sodium phenolate solution, cuprous chloride, S-WAT, sodium formiate is 1: 1.2 ~ 1.4: 1.6 ~ 1.8: 1.2 ~ 1.4;
Step 4): in advance hydrochloric acid and water are made into aqueous hydrochloric acid according to 1: 1.2 ~ 1.3 ratios, step 3) filtrate that obtains enters in acidifying still, in 0.5-1.0h, fast drop aqueous hydrochloric acid to pH value is 1.5-2, be cooled to room temperature, suction filtration, extraction into ethyl acetate, saturated soda water washing is in neutral, steam and add toluene except after ethyl acetate, crystallisation by cooling, centrifugation obtains crude product, obtains purified product after recrystallization, decolouring, all drying processes all use homemade boiling drying equipment, solvent energy recovery;
2. the synthetic method of a kind of 2,6-orcins according to claim 1, is characterized in that: step 2) the 3-chloro-2-methyl phenol that generates not drying directly drip sodium phenolate processed throwing autoclave with alkali.
3. the synthetic method of a kind of 2,6-orcins according to claim 1, is characterized in that: the active rare earth lanthanum orthophosphate of step 2 is as catalyst optimization product color.
4. the synthetic method of a kind of 2,6-orcins according to claim 1, is characterized in that: the homemade boiling drying equipment of step 4, and dry product at 40-50 DEG C, often criticize 0.5h time of drying, recovery wanted by the solvent of volatilization.
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| CN104974054A (en) * | 2015-06-16 | 2015-10-14 | 重庆紫光化工股份有限公司 | Method and apparatus for preparing iminodiacetic acid by using iminodiacetonitrile to produce mother liquor |
| CN105152870A (en) * | 2015-08-27 | 2015-12-16 | 河南黑马动物药业有限公司 | Method for preparing pyroline by means of water re-crystallization |
| CN107473943A (en) * | 2017-08-22 | 2017-12-15 | 江苏鼎烨药业有限公司 | A kind of preparation method of 2,6 orcin |
| CN113214051A (en) * | 2021-05-11 | 2021-08-06 | 南京美茵生命科技有限公司 | Method for synthesizing 2, 6-dihydroxytoluene by using waste acid |
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| CN115784846A (en) * | 2022-11-28 | 2023-03-14 | 安徽英特美科技有限公司 | Preparation method of 2,6-dihydroxytoluene |
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| CN116283500A (en) * | 2023-02-13 | 2023-06-23 | 内蒙古源宏精细化工有限公司 | Synthesis method of high-purity 2,6-dihydroxytoluene |
| CN116283500B (en) * | 2023-02-13 | 2024-05-07 | 内蒙古源宏精细化工有限公司 | Synthesis method of high-purity 2, 6-dihydroxytoluene |
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