CN101774879B - Method for simultaneously extracting high-purity beta-methylnaphthalene and indole from coal tar - Google Patents
Method for simultaneously extracting high-purity beta-methylnaphthalene and indole from coal tar Download PDFInfo
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Abstract
The invention belongs to the field of coal fine chemical industry, relates to a method for extracting high-purity beta-methylnaphthalene and indole, and particularly relates to a method for simultaneously extracting high-purity beta-methylnaphthalene and indole from coal tar. The invention is realized by the following modes: rectifying the washing oil fraction distilled from the coal tar in a vacuum distillation tower under reduced pressure, and collecting a fraction product rich in beta-methylnaphthalene from the side line; feeding the beta-methylnaphthalene distillate product into a high-efficiency intermittent rectifying tower, and cutting a front distillate, and blending the front distillate, the beta-methylnaphthalene crude product, a back distillate and tower bottom liquid; then the crude product of the beta-methylnaphthalene is subjected to semi-continuous azeotropic distillation, a mixture of the beta-methylnaphthalene and an entrainer is extracted from the top of the tower, and the mixture is subjected to standing, layering and separation to obtain the beta-methylnaphthalene; after each cycle of treatment technique, distillation is continued to obtain indole. The invention solves the problems of single product, serious pollution, serious equipment corrosion and the like in the existing beta-methylnaphthalene refining process.
Description
Technical field
The invention belongs to the coal field of fine chemical, relate to a kind of method of extracting high-purity beta-methylnaphthalene and indoles, be specifically related to a kind of method of extracting simultaneously high-purity beta-methylnaphthalene and indoles from coal tar.
Background technology
Beta-methylnaphthalene is a kind of important Organic Chemicals, can be widely used in to produce textile auxiliary agent, lubricant and plant-growth regulator, and highly purified beta-methylnaphthalene is the raw material of synthesise vitamins K class medicine and fodder additives.Natural beta-methylnaphthalene is mainly contained in coal tar, and content is about 1～1.5%, and in mainly concentrate on wash oil fraction (content approximately 8.8%) and fraction of naphthalene oil (content approximately 5.5%).
Because differing, beta-methylnaphthalene and alpha-methyl-naphthalene boiling point only have 3 ℃, while and indoles generation azeotropic, so extract the industrial applications of high-purity beta-methylnaphthalene seldom always, the low indoles beta-methylnaphthalene product that domestic real industrialization at present is purified to more than 97% almost only has one of Baoshan Iron ﹠ Steel Co., Ltd, other family concentrates on lab scale and experimental study stage, but the production technology of Baoshan Iron ﹠ Steel Co., Ltd exists pollution larger on removal indoles technique at present, the problems such as equipment corrosion also can't be extracted the indoles product simultaneously simultaneously.
The method of producing at present beta-methylnaphthalene both at home and abroad mainly contains:
The isomerization method, this method comprises azeotropic distillation, hydrogenating desulfurization, rectifying and isomerization four major parts.Theoretically, the method is considered comparison system, first remove nitrogenous compound with azeotropic distillation, hydrogenation is removed sulfocompound, other component is removed in rectifying again, heptamethylnonane is removed in isomerization, but the very large problem of its existence is can't realize industrial, even particularly isomerization technique does not obtain satisfied achievement at laboratory stage at present yet.
The azeotropic distillation combination process: the method is to obtain methylnaphthalene after with coal tar wash oil rectifying under normal reduced pressure; Then add 10%～20% sulfuric acid in methylnaphthalene, remove quinoline; Add a certain proportion of heptane and thanomin again in the methylnaphthalene component, remove indoles; After alkane is removed in distillation, add entrainer ethylene glycol, carry out rectifying under reduced pressure, pressure is 0.05MPa, and reflux ratio is 10～15:1, cuts 200～210 ℃ of cuts, and the methylnaphthalene of collecting carries out rectifying again and just obtains the beta-methylnaphthalene sterling.The method can obtain the higher product of purity, substantially represented present domestic isolation technique level, but it exists step too much, and the step of the contaminate environment such as pickling is arranged, and can't obtain simultaneously the deficiency of indoles, there is no the example of industrial application.
Recrystallization method: obtain content greater than 80% beta-methylnaphthalene cut with rectificating method, low temperature crystallization then, then carry out suction filtration or centrifugal obtains purity greater than 95% beta-methylnaphthalene.This method is used to some extent in little washing oil source mill, its technique is take industrial beta-methylnaphthalene as raw material at rectifying tower, obtain content greater than 80% beta-methylnaphthalene cut, low temperature crystallization in crystallizer tank, then the whizzer of packing into is centrifugal obtains content greater than 95% beta-methylnaphthalene, but indoles content is greater than 1%.This technique can only be carried out in the season below 20 ℃ at temperature, and labor strength is large, is only suitable in small-scale production.
Indoles is a kind of important fine chemical material, is widely used in the fields such as medicine, agricultural chemicals, spices, foodstuff additive, dyestuff.Natural indoles is substantially all to extract from coal tar fractional distillation, and the method for indoles mainly contains chemical separation technique and physical sepn two general orientation:
Chemical separation technique be to enrichment add basic metal potassium in the coal tar wash oil cut of indoles, the pharmaceutical chemicalss such as sodium or caustic alkali, sulfuric acid make it and indoles generation chemical reaction, after isolating reaction product, the more treated indoles product that obtains.The main drawback of chemical separation technique is that the yield of indoles is low, and technical process is long, periodical operation is many, is difficult to realize mechanize, automatization, contaminate environment.Institute thinks that to seek the indoles yield high, and simple process is easy to realize industrialized method, and the emphasis of research has been transferred to the physical chemistry separating technology.
The physical chemistry separating technology has abroad been reported a few days ago mainly contains highly efficient distilling-azeotropic distillation, extraction-azeotropic distillation, preparation stratography, meat or fish and gets-techniques such as rectifying.
Highly efficient distilling-azeotropic distillation technique: raw material with dephenolize, take off pyridine, take off the coal tar light oil wash oil fraction of acenaphthene, 230～275 ℃ of boiling ranges contain indoles 3%.Highly efficient distilling is decompression operation.Entrainer is mainly for separating of indoles and biphenyl, because both boiling point only differs and only differs from 1 ℃, the isolated indoles cut of azeotropic distillation gets the product of 44.9～51.3 ℃ of fusing points through recrystallization.Entrainer can be recycled through refining.This method still is in the lab scale stage in China.
Extraction-azeotropic distillation technique: the difference of this method and highly efficient distilling-azeotropic distillation technique is to have replaced highly efficient distilling with the extraction cells operation, can reduce facility investment.Raw material is 230～234 ℃ of boiling ranges, contain the coal tar wash oil cut of indoles 6%～7%.Extraction agent ethylene carbonate.Azeotropic distillation carries out in theoretical stage number is 30 tower.Entrainer is selected n-tridecane hydrocarbon, n-tetradecane hydrocarbon, tetrahydro-acenaphthene, decahydro acenaphthene, hexahydro-fluorenes etc.The yield of this method indoles and purity are respectively more than 95%, 98%.
Preparation stratography technique: utilize the absorption agent in solid phase carrier that indoles is separated with the difference of other impurity retention time, this technique is applicable to small-scale production.
Extraction-rectification technique: the extraction process take heptane-single ethylol amine as extraction agent.The distinguishing feature that adopts heptane-single ethylol amine to make extraction agent is that selectivity is high.Can directly make raw material with the coal tar wash oil cut that contains indoles 1%-5%, but the shortcoming that it exists is also not realize industrialized report, can't extract simultaneously the beta-methylnaphthalene product.
Highly efficient distilling-azeotropic distillation of mentioning in patent of the present invention extracts the method for high-purity beta-methylnaphthalene and indoles simultaneously, be different from above-mentioned any method, its ingredient requirement is all lower than above-mentioned any method, and product is better than it, and suitable industrialized production.Special needs to be pointed out is: the method has significant difference with " highly efficient distilling-azeotropic distillation technique " above reported, is that mainly the kind of entrainer is different with application target.The method has not yet to see related documents or patent report.
Summary of the invention
A first aspect of the present invention purpose is to propose a kind of method of extracting simultaneously high-purity beta-methylnaphthalene and indoles from coal tar, the method does not adopt pickling, and can reclaim simultaneously beta-methylnaphthalene and indoles, single to solve the product that existing traditional process for refining beta-methylnaphthalene exists, the problem such as pollute and equipment corrosion is serious.
The present invention solves the problems of the technologies described above by the following technical programs, reaches purpose of the present invention.
Extract simultaneously the method for high-purity beta-methylnaphthalene and indoles from coal tar, comprise the following steps:
A) fore-distillation: take the wash oil fraction of coal tar distillation as raw material, carry out underpressure distillation in vacuum still, be rich in the cut of beta-methylnaphthalene from upper strata side line extraction;
B) intermittently efficiently distillation: the cut that is rich in beta-methylnaphthalene described in a) carries out batch fractionating in batch fractionating tower with step, respectively the extraction front-end volatiles, return and join front-end volatiles, beta-methylnaphthalene crude product, return and join after cut and tower bottoms;
C) the beta-methylnaphthalene crude product semicontinuous azeotropic distillation: with step b) carries out semicontinuous azeotropic distillation in rectifying tower, this semicontinuous azeotropic distillation divides two stages:
C1) the semicontinuous stage, the continuous charging of this stage, the mixture of the continuous extraction beta-methylnaphthalene of tower top and entrainer separates obtaining beta-methylnaphthalene after standing demix;
C2) entrainer recovery stage and indoles production phase, this stage charging stops, and tower reactor constantly steams entrainer and thick quinoline, steams at last indoles.
The vacuum still of step described in a) is that stage number is the sieve-tray tower more than 60 layers, tower top pressure is-80 ~-20kPa, tower top temperature is 195～215 ℃, cutting temperature is 205～225 ℃, reflux ratio is 5～12, and the cut recovery ratio that beta-methylnaphthalene is rich in upper strata side line extraction is that 30 ~ 50%(recovery ratio refers to that the weight of the cut that is rich in beta-methylnaphthalene of extraction accounts for the per-cent of raw material weight).Cut temperature and refer to that upper strata side line extraction is rich in the extraction temperature of the cut of beta-methylnaphthalene.
Step b) batch fractionating tower described in be packed height to be equivalent to stage number be efficient Stainless Steel Helices batch fractionating tower more than 100 layers, tower top pressure is-80 ~-20kPa, effectively extraction section temperature is 175～195 ℃, reflux ratio is 20～40.Effectively extraction section temperature refers to the extraction temperature of beta-methylnaphthalene crude product.
Step c) rectifying tower in semicontinuous azeotropic distillation is that to be equivalent to stage number be efficient Stainless Steel Helices rectifying tower more than 60 layers to packed height, adopt normal pressure or reduced pressure distillation process, reduced pressure distillation process control tower pressure on top surface is-60～10kpa, c1) semicontinuous stage tower top temperature is controlled to be the temperature of ethylene glycol and methylnaphthalene azeotropic, and the normal pressure situation is between 187～191 ℃; C2) entrainer recovery stage and indoles production phase tower top temperature are controlled to be the boiling temperature of indoles, between 250～255 ℃, adjust accordingly in the decompression situation in the normal pressure situation.
Step c) entrainer described in is a kind of in ethylene glycol, monoethanolamine, N-METHYLFORMAMIDE, heptane and glycol.Further, step c) entrainer described in is ethylene glycol, and carrying out beta-methylnaphthalene crude product that described semicontinuous azeotropic distillation adds and the mass ratio of ethylene glycol in step c) is 1:1 ~ 3.
The present invention compared with prior art has following characteristics: by method of the present invention can purify simultaneously highly purified beta-methylnaphthalene product and indoles product, avoid present most of technique can only produce a kind of drawback of product; The present invention has very strong adaptability to raw material, as long as in raw material, beta-methylnaphthalene content greater than 30%, has no requirement to indoles content; Method of the present invention is easy to operate simple, and required equipment is conventional equipment, and processing condition are gentle, and turndown ratio is large; Abandoned present acid cleaning process to the corrosion of equipment and the pollution of environment.Entrainer toxicological harmless effect used in the present invention, and product can physical sepn, and separate thoroughly, quality product is had no effect.The chemical purity of the beta-methylnaphthalene that the present invention obtains can reach more than 97%, and the chemical purity of indoles can reach more than 98%.
Description of drawings
Fig. 1 is schema of the present invention.
Embodiment
Further illustrate technical scheme of the present invention below in conjunction with drawings and Examples.
Referring to Fig. 1.Extract simultaneously the method for high-purity beta-methylnaphthalene and indoles from coal tar, comprise the following steps:
A) fore-distillation: take the wash oil fraction of coal tar distillation as raw material (DMNO-1), in raw material, indoles content is at 2～5wt%, and beta-methylnaphthalene content is at 30～40wt%, and contains the blending ingredients of the impurity such as biphenyl, quinoline beautiful jade, acenaphthene and fluorenes.Raw material (DMNO-1) is carried out underpressure distillation in vacuum still, from the overhead extraction fraction of naphthalene oil, the cut (DMNO-2) of beta-methylnaphthalene is rich in upper strata side line extraction, and the cut of heptamethylnonane is rich in lower floor's side line extraction, and the cut of the heavy constituents such as acenaphthene is rich in the tower reactor extraction.
The preferred stage number of vacuum still is the sieve-tray tower more than 60 layers, tower top pressure is preferably-80 ~-20kPa, tower top temperature is 195～215 ℃, cutting temperature is 205～225 ℃, reflux ratio is 5～12, the cut recovery ratio that beta-methylnaphthalene is rich in upper strata side line extraction is preferably 30 ~ 50%, can with the ratio control of beta-methylnaphthalene and alpha-methyl-naphthalene more than 4:1, be beneficial to the separation of follow-up beta-methylnaphthalene like this.
B) intermittently efficiently distillation: the above-mentioned cut (DMNO-2) that is rich in beta-methylnaphthalene is carried out batch fractionating in batch fractionating tower, respectively the extraction front-end volatiles, return and join front-end volatiles, beta-methylnaphthalene crude product, time join after cut and tower bottoms.
The beta-methylnaphthalene crude product is subsequent processing azeotropic raw material, returns to join front-end volatiles and to return and joins after cut and allocate next still into as raw material.
It is efficient Stainless Steel Helices batch fractionating tower more than 100 layers that batch fractionating tower preferred filler height is equivalent to stage number, tower top pressure is preferably-80 ~-20kPa, effectively extraction section temperature is 175～195 ℃, reflux ratio is 20～40, return dosage and account for 20% of the total amount of packing into, the variable speed method is adopted in the batch fractionating extraction, reduces extraction speed at difficult segregation section.
C) semicontinuous azeotropic distillation: this step is divided two stages, first stage is the semicontinuous stage, mainly that extraction purity is at the beta-methylnaphthalene product more than 97.0%, constantly charging in this process, the mixture of the continuous extraction beta-methylnaphthalene of tower top and ethylene glycol, mixture is after medial launder is standing, and the upper strata is the beta-methylnaphthalene product of purity more than 97%, and lower floor is the ethylene glycol entrainer that can be recycled; Second process is entrainer recovery stage and indoles production phase, and charging stops in this process, and tower reactor constantly steams entrainer and thick quinoline, steams at last purity at the indoles product more than 98.0%.
Step c) rectifying tower in semicontinuous azeotropic distillation is that packed height is equivalent to the efficient Stainless Steel Helices rectifying tower of stage number more than 60 layers, adopts normal pressure or reduced pressure distillation process, and the control tower pressure on top surface is at-60～10kpa, c
1) semicontinuous stage tower top temperature is controlled to be the temperature of ethylene glycol and methylnaphthalene azeotropic, the normal pressure situation is between 187～191 ℃; c
2) entrainer recovery stage and indoles production phase tower top temperature be controlled to be the indoles boiling temperature, between 250～255 ℃, adjust accordingly in the decompression situation in the normal pressure situation.
Semicontinuous azeotropic distillation is mainly to remove the nitrogenous compound that wherein contains, as quinoline and indoles.The preferred ethylene glycol of entrainer, proportioning is selected raw material: ethylene glycol=1:1 ~ 3; Produce the beta-methylnaphthalene product at 50 ~ 100 tons in each semicontinuous stage, each cycle also regenerates to entrainer at the production indoles simultaneously.
Embodiment 1
Be 35.24% with 300 tons of beta-methylnaphthalene content, indoles content is that (vacuum still is that stage number is the sieve-tray tower of 60 layers through fore-distillation as raw material (DMNO-1) for the wash oil fraction of 4.12% coal tar distillation, tower top pressure is controlled to be-66kPa, cutting temperature is 205～215 ℃, control of reflux ratio is 8, the cut recovery ratio that beta-methylnaphthalene is rich in upper strata side line extraction is controlled to be 36%), obtaining beta-methylnaphthalene content is 76.67wt%, and indoles content is 155 tons of the cuts that is rich in beta-methylnaphthalene (DMNO-2) of 3.01wt%; The cut (DMNO-2) that is rich in beta-methylnaphthalene in efficient Stainless Steel Helices batch fractionating tower distillation (it is 110 layers that the packed height of efficient Stainless Steel Helices batch fractionating tower is equivalent to stage number, tower top pressure is controlled to be-80Pa, effectively extraction section temperature is approximately 181 ℃, reflux ratio is 32) beta-methylnaphthalene crude product that to obtain 72 tons of beta-methylnaphthalene content be 96.4wt%, wherein indoles content is 1.2wt%; (packed height of efficient Stainless Steel Helices rectifying tower is equivalent to 60 layers of stage number to the beta-methylnaphthalene crude product through semicontinuous component distillation device component distillation, tower top pressure is normal pressure), entrainer ethylene glycol and raw material ratio are 1.8:1, obtaining chemical purity is 69.5 tons of 97.6% beta-methylnaphthalenes, and chemical purity is 750 kilograms of 97.1% indoles products.
Embodiment 2
Be 38.07% with beta-methylnaphthalene content, indoles content is that (vacuum still is that stage number is the sieve-tray tower of 100 layers through fore-distillation as raw material (DMNO-1) for the wash oil fraction of 3.79% coal tar distillation, tower top pressure is-20kPa, cutting temperature is 215～225 ℃, reflux ratio is 12, the recovery ratio that the cut of beta-methylnaphthalene is rich in upper strata side line extraction is 50%), obtaining beta-methylnaphthalene content is 77.8%, indoles content is 2.39% the cut that is rich in beta-methylnaphthalene (DMNO-2), and the recovery rate of beta-methylnaphthalene is 70.5%; (packed height of efficient Stainless Steel Helices batch fractionating tower is equivalent to 100 layers of stage number to the cut (DMNO-2) that is rich in beta-methylnaphthalene at efficient Stainless Steel Helices batch fractionating tower, tower top pressure is-20kPa, effectively extraction section temperature is approximately 195 ℃, reflux ratio is 20) in distill to such an extent that the content of beta-methylnaphthalene is 96.2% beta-methylnaphthalene crude product, wherein indoles content is 1.5wt%, yield be 55%(deduct back join after); (packed height of efficient Stainless Steel Helices rectifying tower is equivalent to 100 layers of stage number to the beta-methylnaphthalene crude product through semicontinuous component distillation device component distillation, tower top pressure is normal pressure), entrainer and raw material ratio are 3:1, obtaining pure beta-methylnaphthalene chemical purity is 97.3%, yield is 97%, the indoles chemical purity is 97.5%, and yield is 99.1%.
In the present invention, the content detection of beta-methylnaphthalene is according to the ferrous metallurgy industry standard YB/T 4150-2006 of People's Republic of China (PRC) development and the issue of the reform council, and instrument is Shimadzu GC-4000 series gas chromatograph (Shimadzu Seisakusho Ltd. of Amada Co., Ltd. product).The content detection of indoles also adopts Shimadzu GC-4000 series gas chromatograph, detects according to ordinary method.
Those of ordinary skill in the art will be appreciated that, above embodiment illustrates the present invention, and be not to be used as limitation of the invention, as long as in connotation scope of the present invention, all will drop in claims scope of the present invention variation, the modification of the above embodiment.
Claims (5)
1. extract simultaneously the method for high-purity beta-methylnaphthalene and indoles from coal tar, it is characterized in that, comprise the following steps:
A) fore-distillation: take the wash oil fraction of coal tar distillation as raw material, carry out underpressure distillation in vacuum still, be rich in the cut of beta-methylnaphthalene from upper strata side line extraction;
B) intermittently efficiently distillation: the cut that is rich in beta-methylnaphthalene described in a) carries out batch fractionating in batch fractionating tower with step, respectively the extraction front-end volatiles, return and join front-end volatiles, beta-methylnaphthalene crude product, return and join after cut and tower bottoms;
C) the beta-methylnaphthalene crude product semicontinuous azeotropic distillation: with step b) carries out semicontinuous azeotropic distillation in rectifying tower, rectifying tower in semicontinuous azeotropic distillation is that to be equivalent to stage number be efficient Stainless Steel Helices rectifying tower more than 60 layers to packed height, adopt normal pressure or reduced pressure distillation process, reduced pressure distillation process control tower pressure on top surface is-60～10kpa, and this semicontinuous azeotropic distillation divides two stages:
c
1) the semicontinuous stage, the continuous charging of this stage, the mixture of the continuous extraction beta-methylnaphthalene of tower top and entrainer separates obtaining beta-methylnaphthalene after standing demix, and described entrainer is ethylene glycol, and the tower top temperature in this stage is the temperature of ethylene glycol and methylnaphthalene azeotropic;
c
2) entrainer recovery stage and indoles production phase, this stage charging stops, and tower reactor constantly steams entrainer and thick quinoline, steams at last indoles, and the tower top temperature in this stage is the boiling temperature of indoles.
2. the method for extracting simultaneously high-purity beta-methylnaphthalene and indoles from coal tar according to claim 1, it is characterized in that: the vacuum still of step described in a) is that stage number is the sieve-tray tower more than 60 layers, tower top pressure is-80 ~-20kPa, cutting temperature is 205～225 ℃, reflux ratio is 5～12, and the recovery ratio that the cut of beta-methylnaphthalene is rich in upper strata side line extraction is 30 ~ 50%.
3. the method for extracting simultaneously high-purity beta-methylnaphthalene and indoles from coal tar according to claim 1, it is characterized in that: the batch fractionating tower step b) is that to be equivalent to stage number be efficient Stainless Steel Helices batch fractionating tower more than 100 layers to packed height, tower top pressure is-80 ~-20kPa, effectively extraction section temperature is 175～195 ℃, and reflux ratio is 20～40.
4. the method for extracting simultaneously high-purity beta-methylnaphthalene and indoles from coal tar according to claim 1 is characterized in that: carrying out beta-methylnaphthalene crude product that described semicontinuous azeotropic distillation adds and the mass ratio of ethylene glycol in step c) is 1:1 ~ 3.
5. the method for extracting simultaneously high-purity beta-methylnaphthalene and indoles from coal tar according to claim 1, it is characterized in that: in described wash oil fraction, beta-methylnaphthalene content is greater than 30%.
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| CN102935292B (en) * | 2011-08-16 | 2015-01-07 | 上海宝钢化工有限公司 | Method and device for removing indole from beta-methylnaphthalene |
| CN103992199A (en) * | 2014-05-04 | 2014-08-20 | 黄骅市信诺立兴精细化工股份有限公司 | Method for extracting highly pure beta-methylnaphthalene from coal tar wash oil |
| CN106543067A (en) * | 2015-09-17 | 2017-03-29 | 鞍钢股份有限公司 | A kind of method that indoles is extracted in therefrom matter washing oil |
| CN106316753A (en) * | 2016-08-23 | 2017-01-11 | 吴江市万事达环保溶剂有限公司 | Separation and purification technology of 2-methylnaphthalene |
| CN111205157B (en) * | 2018-11-21 | 2022-08-09 | 河北中化鑫宝化工科技有限公司 | Process for purifying liquids containing crude methylnaphthalenes |
| CN112279799B (en) * | 2019-07-26 | 2022-02-22 | 中石化南京化工研究院有限公司 | Method for preparing spice-grade indole by extraction crystallization |
| CN112569633A (en) * | 2019-09-30 | 2021-03-30 | 青岛海德利纳米科技有限公司 | Method for separating, enriching or producing phenolic compounds, and method and equipment for processing oil products |
| JP2023546762A (en) * | 2021-09-14 | 2023-11-08 | 煤炭科学技術研究院有限公司 | Acylation liquid and process method for continuous synthesis of acylnaphthalene using acylation liquid |
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