CN103121908B - Method for separating mesitylene via extractive distillation - Google Patents
Method for separating mesitylene via extractive distillation Download PDFInfo
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Abstract
The invention discloses a method for separating mesitylene via extractive distillation, wherein an extractive distillation solvent adopted in the method is one of N-methyl-2-pyrrolidone and 2-pyrrolidone, and preferably is N-methyl-2-pyrrolidone. The method disclosed by the invention has the advantages of being relatively simple in separation process, low in operating energy consumption, and high in product yield. The extractive distillation solvent adopted in the method is high in separation efficiency for mesitylene and o-methyl-ethylbenzene, so that the separation process can be realized on an extractive distillation tower with few tower plates; and moreover, the solvent is easy to recover and good in chemical thermostability.
Description
Technical field
The present invention relates to chemical field, say further, relate to a kind of method of separation of extractive distillation sym-trimethylbenzene.
Background technology
Sym-trimethylbenzene is a kind of fine chemical material of preciousness, through nitrated, hydrogenating reduction, produce 2,4,6-trimethylaniline, then with the condensation of Isosorbide-5-Nitrae dihydroxyanthraquinone, sulfonation, then generate the gorgeous blue RAW in slightly acidic pula; Another kind of dyestuff be sym-trimethylbenzene through sulfonation, nitrated, reduction, make 2,4-diamino-sym-trimethylbenzene-6-sulfonic acid, blue color base is condensed into again with bromamine acid, then react with oxyethyl group dichloro s-triazine, finally generate reactive brilliant blue K-3R and RAN, for stamp and pad dyeing; In addition 2,4,6-trimethylaniline and the condensation of alpha-chloro methyl propionate, can be made into cornfield herbicidal, is made into 20% solution and uses.In addition, be that raw material can be made into antioxidant 330, trimesic acid with sym-trimethylbenzene, multiple Chemicals and the chemical intermediates such as 2,4,6-tri-cresols, also may be used for synthesis trimethylbenzene formaldehyde resin, its purposes is wide, and added value is very high.Sym-trimethylbenzene about 10% in oil at the bottom of refinery reformer benzenol hydrorefining.This part reformation carbon nine resource of current China does not develop always further, for Chang Ling refinery, this factory produces sym-trimethylbenzene about 0.7 ten thousand tons per year at present, if be isolated purification, petroleum resources not only can be made to obtain Appropriate application, also can increase the economic benefit of enterprise.
Because the boiling point of component each in C9 aromatic mixture is very close, particularly sym-trimethylbenzene and adjacent methyl-ethyl benzene boiling point only poor about 0.5 DEG C, relative volatility is 1.009, larger with conventional distillation separating difficulty, if be separated it with conventional distillation method, need thousands of pieces of theoretical stages, be therefore actually and cannot realize.
Up to now, be developed many methods preparing sym-trimethylbenzene, mainly contain the kinds of processes such as unsym-trimethyl benzene isomerization process, extraction fractional distillation, molecular sieve absorption process, complexing/partition method, alkylation-partition method, the raw material that above technique adopts all derives from C9 aromatic cut.It is reported, in the methods described above, extraction fractional distillation product yield is higher, and solvent is reused, and does not produce refuse, can comprehensive utilization of C
9aromatic hydrocarbon resource, and there is no environmental issue, compare with other method and there is many-sided advantage, there is very high commercial value.Extraction fractional distillation ultimate principle is the effect by selective solvent, changes the relative volatility between sym-trimethylbenzene and o-methylethylbenzene, thus reaches the object of purification sym-trimethylbenzene.Therefore, extraction distillation solvent plays a part crux to sym-trimethylbenzene and adjacent methyl-ethyl benzene separation efficiency in the technico-economical comparison of sepn process.
US Patent No. 3220933 discloses using dimethyl phthalate as extraction solvent, to C
9aromatic hydrocarbons carries out extractive distillation, because the separating effect of this solvent to sym-trimethylbenzene and o-methylethylbenzene is not good, only can obtain the sym-trimethylbenzene of 87%, well below 98% (purity of sym-trimethylbenzene first grade).Domestic Nanjing Normal University to the method carried out further research (extracting rectifying produces the experimental study of sym-trimethylbenzene. during chemical industry print .2000, 5:18 ~ 20.), from experimental result, when reflux ratio is 4, when the mass ratio of solvent and feedstock material is 10, extractive distillation column number of theoretical plate N is under the condition of 102 pieces, the massfraction of the sym-trimethylbenzene material in overhead distillate can reach more than 0.92, and analog calculation has been carried out to this process, analog calculation shows, when with N=170, the massfraction of the sym-trimethylbenzene material under equal conditions in overhead distillate just can reach more than 98%, dimethyl phthalate is adopted to prepare extracting rectifying column plate number requirement too high (N=170) needed for highly purified sym-trimethylbenzene as extraction solvent, solvent/material rate is excessive.
Chinese patent CN1958538A discloses a kind of method that double solvent extraction is separated C9 aromatic, comprises and C9 aromatic mixture is carried out prefractionation, intercepts the enriched fraction containing sym-trimethylbenzene and o-methylethylbenzene; Enriched fraction containing sym-trimethylbenzene and o-methylethylbenzene is introduced the middle part of double solvent extraction rectifying tower, high boiling solvent injects from described double solvent extraction rectifier, low boiling point solvent injects from described double solvent extraction rectifying tower bottom, under two kinds of solvent synergistic extraction effects, tower top obtains the mixed fraction containing sym-trimethylbenzene and low boiling point solvent, obtains the mixed fraction containing portion's o-methylethylbenzene and high boiling solvent at the bottom of tower; Tower top is separated respectively with two bursts of mixed fraction of tower reactor gained in solvent recovery tower, will the sym-trimethylbenzene and adjacent methyl-ethyl benzene product discharge system that obtain be separated, and reuse after two kinds of solvent recuperation.Owing in turn introducing a kind of solvent, must be separated this solvent and recycle, thus need increase low boiling point solvent knockout tower.There is the shortcoming of equipment one-time investment and flow process relative complex.In addition, discharge due to low boiling point solvent and sym-trimethylbenzene with from tower top, cause sepn process energy consumption to increase.
Chinese patent CN1513818A reports a kind of rectifying in extraction crossing in conjunction with separation of C
9technique, adopt N-N-formyl morpholine N-as extraction distillation solvent, in overhead distillate, the content of sym-trimethylbenzene can reach more than 98.5%, because the separation efficiency of this solvent to sym-trimethylbenzene and adjacent methyl-ethyl benzene is lower, extractive distillation column number of theoretical plate N reaches 123 pieces, and sym-trimethylbenzene yield is only 84%.Therefore, for solving the problems of the prior art, provide a kind of method of separation of extractive distillation sym-trimethylbenzene, the method with the separation of extractive distillation sym-trimethylbenzene that lock out operation is relatively simple, operation energy consumption is low, product yield is high and investment is lower is very necessary.
Summary of the invention
For solving the problems of the prior art, the invention provides a kind of method of separation of extractive distillation sym-trimethylbenzene, there is the advantage that separating technology is relatively simple, operation energy consumption is low, product yield is high, the extraction distillation solvent that the method utilizes is high to the separation efficiency between sym-trimethylbenzene and adjacent methyl-ethyl benzene, its sepn process is easily realized on the extractive distillation column that stage number is less, and this solvent is easy to recovery, chemical heat is stablized.
The object of this invention is to provide a kind of method of separation of extractive distillation sym-trimethylbenzene.
The extraction distillation solvent that described method adopts is the one in METHYLPYRROLIDONE, 2-Pyrrolidone, is preferably METHYLPYRROLIDONE.
The present inventor is through deep research, screen a large amount of extraction distillation solvent for separation of extractive distillation sym-trimethylbenzene, surprised discovery, the relative volatility between sym-trimethylbenzene and o-methylethylbenzene can be changed significantly containing nitrogen compound METHYLPYRROLIDONE, 2-Pyrrolidone, and compare with the solvent compositions containing inorganic salt, there is not blocking pipe, advantage simple to operate.
Described method comprises:
(1) the C9 aromatic mixture through removing light constituent is introduced unsym-trimethyl benzene tower, tower top discharges the enriched fraction containing sym-trimethylbenzene and methyl-ethyl benzene, and tower reactor draws the logistics containing sym-trimethylbenzene;
(2) enriched fraction that unsym-trimethyl benzene column overhead is discharged containing sym-trimethylbenzene and methyl-ethyl benzene is introduced from the middle part of extractive distillation column, described extraction distillation solvent is introduced from tower top, after extracting rectifying, sym-trimethylbenzene is discharged from the top of extractive distillation column, discharges the logistics containing o-methylethylbenzene and solvent at the bottom of tower;
(3) by discharging the logistics containing o-methylethylbenzene and solvent at the bottom of extractive distillation column tower, introduce solvent recovery tower, obtain logistics containing o-methylethylbenzene and discharge from solvent recuperation tower top, extraction distillation solvent is discharged Posterior circle and is utilized at the bottom of solvent recovery tower.
Wherein, by weight, described extraction distillation solvent consumption is 0.5-12 times of the enriched fraction inlet amount of described sym-trimethylbenzene and methyl-ethyl benzene, and preferred 3-8 doubly;
(1) light constituent removing the C9 aromatic mixture of light constituent in step refers to that boiling point is less than the component of sym-trimethylbenzene, mainly isopropyl benzene, n-proplbenzene, to methyl-ethyl benzene.(1) method removing light constituent in C9 aromatic mixture in step can adopt precise distillation of the prior art or extraction and distillation technology.
Operational condition can adopt common operational condition in this area, can be preferred in the present invention:
The theoretical plate number of described unsym-trimethyl benzene tower is 60-100, and trim the top of column is than being 10-20, and tower top temperature is 150-170 DEG C, and column bottom temperature is 170-200 DEG C, and tower top pressure is 0.08-0.12MPa, and tower bottom pressure is 0.09-0.14MPa.
The theoretical plate number of described extractive distillation column is 70-120, and trim the top of column is than being 2-5, and tower top temperature is 150-170 DEG C, and column bottom temperature is 190-220 DEG C, and tower top pressure is 0.08-0.12MPa, and tower bottom pressure is 0.09-0.14MPa.
The theoretical plate number of described recovery tower is 10-20, and the reflux ratio of tower top is 1-3, and tower top temperature is 155-170 DEG C, and column bottom temperature is 190-230 DEG C, and tower top pressure is 0.08-0.12MPa, and tower bottom pressure is 0.09-0.14MPa.
Described C9 aromatic mixture can preferably from oil, xylene isomerization by-product, cycle oil or cracking naphtha at the bottom of platinum reforming tower, wherein the content of sym-trimethylbenzene is 8 % by weight-50 % by weight, the content of adjacent methyl-ethyl benzene is 5 % by weight-50 % by weight, and the content of unsym-trimethyl benzene is 8 % by weight-60 % by weight.The C9 aromatic composition of different sources is slightly different, can regulate flow process and operational means according to practical situation.
Method of the present invention has the following advantages: solvent is high to the separation efficiency between sym-trimethylbenzene and adjacent methyl-ethyl benzene,
1, the separation efficiency of solvent to sym-trimethylbenzene and adjacent methyl-ethyl benzene adopted due to the method is high, not only make the separation of sym-trimethylbenzene can realize on the extractive distillation column that stage number is less, but also reduce extraction distillation solvent consumption (reducing the mass ratio of the enriched fraction of solvent/sym-trimethylbenzene and methyl-ethyl benzene), investment can be reached less, the object that production process energy consumption is lower.
2, adopt method of the present invention, the sym-trimethylbenzene yield obtained is significantly improved, and therefore improves the economic benefit obtaining sym-trimethylbenzene product from C9 aromatic.
Accompanying drawing explanation
Fig. 1: separation of extractive distillation sym-trimethylbenzene schematic flow sheet of the present invention
Description of reference numerals
Equipment class: T1 unsym-trimethyl benzene tower, T2 extractive distillation column, T3 solvent recovery tower
Logistics class: the 1 C9 aromatic mixture removing light constituent, the enriched fraction of 2 sym-trimethylbenzene and methyl-ethyl benzene, 3 unsym-trimethyl benzenes, 4 sym-trimethylbenzene, 5 o-methylethylbenzenes and solvent, 6 logistics mainly containing o-methylethylbenzene, 7 circulating solvents
Embodiment
Below in conjunction with embodiment, further illustrate the present invention.
Embodiment:
As shown in Figure 1, the C9 aromatic mixture 1 through removing light constituent enters the middle and lower part of unsym-trimethyl benzene tower T1, and tower top discharges the enriched fraction 2 containing sym-trimethylbenzene and portion's methyl-ethyl benzene, and tower reactor draws the main logistics 3 containing sym-trimethylbenzene; The middle and lower part of extractive distillation column T2 is entered from the enriched fraction 2 containing sym-trimethylbenzene and portion's methyl-ethyl benzene of T1 tower top outflow, circulating solvent 7 enters extractive distillation column T2 by top, through separation of extractive distillation, tower top distillates sym-trimethylbenzene 4, discharges the main logistics 5 containing o-methylethylbenzene and solvent at the bottom of tower; The main logistics 5 containing o-methylethylbenzene and solvent of discharging from T2 tower reactor is introduced into solvent recovery tower, and the main logistics 6 containing o-methylethylbenzene is discharged from solvent recuperation tower top, and extraction distillation solvent 7 is discharged Posterior circle and utilized at the bottom of solvent recovery tower.
Extraction distillation solvent used is METHYLPYRROLIDONE;
Raw material used in embodiment is the C9 aromatic mixture removing light constituent, and wherein contain the sym-trimethylbenzene of 35.10 % by weight, its concrete component and content are in table 1.
Table 1 removes C9 aromatic mixture composition and the boiling point of light constituent
| Ingredient names | Content (% by weight) | Boiling point (DEG C) |
| Light constituent | 0.40 | - |
| Sym-trimethylbenzene | 35.10 | 164.74 |
| O-methylethylbenzene | 38.10 | 165.18 |
| Unsym-trimethyl benzene | 26.40 | 169.38 |
The yield of product is calculated by following formula:
Yield and the purity of concrete separation process conditions, each logistics explanation, product see table 2, table 3, table 4.
The separation process conditions of table 2 embodiment
Each logistics explanation of table 3 embodiment
Each product yield of table 4 embodiment and purity
| Unsym-trimethyl benzene yield (% by weight) | O-methylethylbenzene yield (% by weight) | Sym-trimethylbenzene yield (% by weight) |
| 98.50 | 99.51 | 93.20 |
| Unsym-trimethyl benzene purity (% by weight) | O-methylethylbenzene purity (% by weight) | Sym-trimethylbenzene purity (% by weight) |
| 99.3 | 93.38 | 98.5 |
Comparative example:
Raw material used is the C9 aromatic mixture removing light constituent, and wherein contain the sym-trimethylbenzene of 35.10 % by weight, its concrete component and content are in table 1.
Extraction distillation solvent adopts China's specially sharp N-N-formyl morpholine N-disclosed of CN1513818A.Implement by the method for enriched mesitylene from C9 aromatic described in Fig. 1, the yield of concrete separation process conditions, each logistics explanation, product and purity in table 5, table 6, table 7.
The separation process conditions of table 5 comparative example
Each logistics explanation of table 6 comparative example
Each product yield of table 7 comparative example and purity
| Unsym-trimethyl benzene yield (% by weight) | O-methylethylbenzene yield (% by weight) | Sym-trimethylbenzene yield (% by weight) |
| 98.50 | 99.8 | 82.8 |
| Unsym-trimethyl benzene receives purity (% by weight) | O-methylethylbenzene purity (% by weight) | Sym-trimethylbenzene purity (% by weight) |
| 99.3 | 85.90 | 98.50 |
From table 2,5, owing to adopting the extraction distillation solvent that separation efficiency is higher, solvent/raw material (weight rate ratio) is reduced to 7 from 10, thus reduces energy consumption; In addition, from table 4,7, owing to adopting the extraction distillation solvent that separation efficiency is higher, product sym-trimethylbenzene yield brings up to 93.2% from 82.3%, therefore improves the economic benefit obtaining sym-trimethylbenzene product from C9 aromatic.
Claims (6)
1. a method for separation of extractive distillation sym-trimethylbenzene, is characterized in that:
The extraction distillation solvent that described method adopts is the one in METHYLPYRROLIDONE, 2-Pyrrolidone;
Said method comprising the steps of:
(1) the C9 aromatic mixture through removing light constituent is introduced unsym-trimethyl benzene tower, tower top discharges the enriched fraction containing sym-trimethylbenzene and methyl-ethyl benzene, and tower reactor draws the logistics containing sym-trimethylbenzene;
(2) enriched fraction that unsym-trimethyl benzene column overhead is discharged containing sym-trimethylbenzene and methyl-ethyl benzene is introduced from the middle part of extractive distillation column, described extraction distillation solvent is introduced from tower top, after extracting rectifying, sym-trimethylbenzene is discharged from the top of extractive distillation column, discharges the logistics containing o-methylethylbenzene and solvent at the bottom of tower;
(3) by discharging the logistics containing o-methylethylbenzene and solvent at the bottom of extractive distillation column tower, introduce solvent recovery tower, the logistics containing o-methylethylbenzene is discharged from solvent recuperation tower top, and extraction distillation solvent is discharged Posterior circle and utilized at the bottom of solvent recovery tower.
2. the method for separation of extractive distillation sym-trimethylbenzene as claimed in claim 1, is characterized in that:
Described extraction distillation solvent is METHYLPYRROLIDONE.
3. the method for separation of extractive distillation sym-trimethylbenzene as claimed in claim 1, is characterized in that:
Described extraction distillation solvent consumption is 0.5-12 times of the enriched fraction inlet amount of described sym-trimethylbenzene and methyl-ethyl benzene.
4. the method for separation of extractive distillation sym-trimethylbenzene as claimed in claim 3, is characterized in that:
Described extraction distillation solvent consumption is 3-8 times of the enriched fraction inlet amount of described sym-trimethylbenzene and methyl-ethyl benzene.
5. the method for separation of extractive distillation sym-trimethylbenzene as claimed in claim 1, is characterized in that:
The theoretical plate number of described extractive distillation column is 70-120, and trim the top of column is than being 2-5, and tower top temperature is 150-170 DEG C, and column bottom temperature is 190-220 DEG C, and tower top pressure is 0.08-0.12MPa, and tower bottom pressure is 0.09-0.14MPa.
6. the method for separation of extractive distillation sym-trimethylbenzene as claimed in claim 1, is characterized in that:
Described C9 aromatic mixture is from oil, xylene isomerization byproduct, cycle oil or cracking naphtha at the bottom of platinum reforming tower, wherein the content of sym-trimethylbenzene is 8 % by weight-50 % by weight, the content of adjacent methyl-ethyl benzene is 5 % by weight-50 % by weight, and the content of unsym-trimethyl benzene is 8 % by weight-60 % by weight.
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Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105542834A (en) * | 2014-10-30 | 2016-05-04 | 中国石化扬子石油化工有限公司 | Composite solvent for extraction distillation separation of aromatic hydrocarbons, and applications thereof |
| CN104591952A (en) * | 2014-12-25 | 2015-05-06 | 天津大学 | Method for refining mesitylene by virtue of differential pressure thermal coupling rectification |
| CN105837394B (en) * | 2016-04-05 | 2018-12-21 | 天津大学 | A kind of method of purification of high-purity 1,2,3-trimethylbenzene |
| CN109627140A (en) * | 2017-10-09 | 2019-04-16 | 中国石化扬子石油化工有限公司 | A kind of mesitylene extraction and rectification separation method |
| CN111886062B (en) * | 2018-11-01 | 2022-04-26 | 株式会社Lg化学 | Method for separating organic solvent from mixed solution containing organic solvent |
| CN114292155B (en) * | 2021-12-31 | 2024-05-03 | 黄河三角洲京博化工研究院有限公司 | Method for purifying mesitylene through thermal coupling |
| CN114213208B (en) * | 2021-12-31 | 2024-01-30 | 黄河三角洲京博化工研究院有限公司 | Method for extracting, rectifying and purifying mesitylene by high-efficiency composite solvent |
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| CN1513818A (en) * | 2003-06-30 | 2004-07-21 | ����ʦ����ѧ | Rectification and extraction crossing and combining separation process of carbon 9 arene |
| KR100623187B1 (en) * | 2002-12-28 | 2006-09-11 | 차이나 페트로리움 앤드 케미컬 코포레이션 | A process for separating aromatics by extractive distillation and a composite solvent used therein |
| CN1958538A (en) * | 2005-10-31 | 2007-05-09 | 中国石油化工股份有限公司 | Method of double solvents, benzene substitutive rectification for separating c9 aromatics |
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| CN1278291A (en) * | 1997-09-03 | 2000-12-27 | Hfm国际公司 | Aromatics separation process and method of retrofitting existing equipment for same |
| KR100623187B1 (en) * | 2002-12-28 | 2006-09-11 | 차이나 페트로리움 앤드 케미컬 코포레이션 | A process for separating aromatics by extractive distillation and a composite solvent used therein |
| CN1513818A (en) * | 2003-06-30 | 2004-07-21 | ����ʦ����ѧ | Rectification and extraction crossing and combining separation process of carbon 9 arene |
| CN1958538A (en) * | 2005-10-31 | 2007-05-09 | 中国石油化工股份有限公司 | Method of double solvents, benzene substitutive rectification for separating c9 aromatics |
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