CN105399594A - Method for separating p-xylene from xylene mixture - Google Patents
Method for separating p-xylene from xylene mixture Download PDFInfo
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Abstract
The invention provides a method for separating p-xylene from a xylene mixture. The method comprises the following steps that (a) catalytic hydrogenation, (b) distillation separation, (c) dehydrogenation reaction and (d) separation and purification. A metal-modified molecular sieve catalyst used in the catalytic hydrogenation process has the function of selecting and isomerizing o-xylene, m-xylene and ethylbenzene to generate the p-xylene, and accordingly the p-xylene yield can be effectively increased. By the adoption of the method, the rectification separation difficulty is reduced to the great degree, and the energy consumption and equipment investment scale are reduced. An obtained p-xylene product has higher yield, and the final product is higher in purity after being further purified.
Description
Technical field
The present invention relates to the technical field of organic chemical industry, be specially a kind of method of separating paraxylene from xylene mixture.
Background technology
P-Xylol (PX) is the maximum C8 aronmatic of industrial consumption, and it is the precursor of terephthalic acid (PTA).Terephthalic acid is the important source material of polyester industrial and plastics industry, and in the consumption structure of global PX, the PX of more than 80% is in order to produce PTA.P-Xylol is also widely used in fields such as medicine, agricultural chemicals, dyestuff and solvents.The market demand of p-Xylol is in ascendant trend always, and production capacity deficiency exists always.
The traditional technology one of industrial production p-Xylol is xylol isomerization, and two is toluene and C9 aromatic disproportion and transalkylation.According to the difference of xylol physicochemical property, mainly adopt the technology such as the separation of fractionation by adsorption, zeolite membrane, complexing abstraction, Crystallization Separation to carry out separation to xylol at present and obtain p-Xylol.
Crystallization process utilizes the fusing point of each component of C8 aromatic hydrocarbons to have larger gap: p-Xylol 13.3 DEG C, o-Xylol-25.2 DEG C, m-xylene-47.9 DEG C, and-94.95 DEG C, ethylbenzene, can by p-xylene separation the highest for fusing point out.As para-xylene concentration in raw material is not high, for reaching the acceptable yield of industrial production, general employing two sections of crystallizations.US3177255A, US3467724A describe the method for two sections of Crystallization Separation.But, in the physical system of three kinds of xylene isomers, there is the eutectic mixture that two are important: p-Xylol/m-xylene binary eutectic and p-Xylol/o-Xylol binary eutectic.Along with p-Xylol is from crystalline mixture, remaining mixture, close to the one in these binary eutectics, is but determined in the initial composition of mixture.Therefore, in the technique of business level, p-Xylol crystallization makes close to but does not reach binary eutectic to avoid the cocrystallization of other xylene isomer of the purity that can reduce the p-Xylol obtained.Due to these binary eutectics, often only have about 70% by the yield of a callable para-xylene product of crystallization processes process is the highest, likely lose the growth of the PX yield obtained by disproportionation alkylation and isomerization workshop section.In addition, crystallization is very expensive, because different xylene isomers all exists extremely low temperature crystallization.
Fractionation by adsorption is the separation utilizing xylol rate of diffusion difference on the sorbent to carry out, and adopting simulated Moving Bed Adsorption Separation Technology more, adopt faujusite as sorbent material industrial.The micro channel of about 1nm in molecular sieve is utilized to adsorb C8 Isomers, and micropore is all strong for the absorption property of other isomer of adsorptive power comparison of p-Xylol, desorbing agent generally adopts p-Diethylbenzene or toluene, in simulation moving-bed, the countercurrent flow of liquid feed and solid adsorbent is not move realization by the physics of solid, but injects to carry out analogous reverse flow with the position of drawing along fixed adsorbent bed by periodic variation liquid.US2985589A describes the method utilizing the simulation moving-bed separating paraxylene of adverse current; US3686342A, US3734974A, CN98810104.1 describe the X or Y zeolite that sorbent material that fractionation by adsorption uses is barium type or barium potassium type; US3558732A, US3686342A use toluene and p-Diethylbenzene as the desorbing agent of fractionation by adsorption respectively.But simulated moving bed adsorption technology has that it is restricted and operation is expensive, because it needs the internal recycling of a large amount of hydrocarbons desorbent material.In addition, because the monopolization of sorbent material controls, adsorption tower inner parts structure is complicated, and manufacture difficulty is large, and installation requirement is high, and domestic do not have ripe achievement in research to substitute, and PX production cost is higher.
Summary of the invention
For solving the problem, the invention discloses a kind of method of separating paraxylene from xylene mixture.
In order to reach above object, the invention provides following technical scheme:
A method for separating paraxylene from xylene mixture, comprises the following steps:
A) shortening: xylol raw material and circulating hydrogen are entered reactor one simultaneously, control the reaction pressure 6.0 ~ 8.0MPa in reactor one, temperature of reaction is 250 ~ 350 DEG C, the volume ratio of hydrogen hydrocarbon is 500 ~ 700, under the effect of hydrogenation catalyst, xylol raw material carries out selectivity isomerization-hydrogenation reaction under hydro condition, generates the logistics containing Isosorbide-5-Nitrae-dimethyl cyclohexane after reaction; Hydrogenation catalyst is metal-modified molecular sieve catalyst, and the metal in metal-modified molecular sieve catalyst is one or more in Zn, Cu, Ni, Mn, Cr and Fe; Molecular sieve is Y zeolite;
B) rectifying separation: by step a) in generate containing 1, the logistics of 4-dimethyl cyclohexane is sent into rectifying separation unit and is carried out rectifying, rectifying separation unit adopts plate distillation column, logistics enters in the middle part of rectifying tower, 1,4-dimethyl cyclohexane flows out from tower top, unreacted dimethylbenzene is got back to reactor as raw material after discharging at the bottom of still, at rectifying tower tower top, condenser is set, at the bottom of tower, reboiler is set, tower top service temperature is 90 ~ 110 DEG C, and working pressure is 0.1 ~ 0.5MPa, and tower reactor service temperature is 120 ~ 150 DEG C;
C) dehydrogenation reaction: after rectifying separation, 1,4-dimethyl cyclohexane enters reactor two, control reaction pressure 1.0 ~ 1.5MPa in reactor two, temperature of reaction is 400 ~ 500 DEG C, and hydrogen/hydrocarbon mol ratio is 5 ~ 10, under the effect of dehydrogenation catalyst, Isosorbide-5-Nitrae-dimethyl cyclohexane produces p-Xylol by dehydrogenation reaction, and dehydrogenation reaction used catalyst is containing one or more loaded catalyst in transition metal Pt, Pd, Ni, Mo, Cu or Zn;
D) separating-purifying: p-Xylol step c) obtained carries out rectifying, isolates unreacted Isosorbide-5-Nitrae-dimethyl cyclohexane, obtains p-Xylol finished product, and isolated unreacted Isosorbide-5-Nitrae-dimethyl cyclohexane sends reactor two back to.
As preferably, the reaction pressure 7.2MPa in reactor one described in step a), temperature of reaction is 300 DEG C, and the volume ratio of hydrogen hydrocarbon is 600.
As preferably, in the metal-modified molecular sieve catalyst described in step a), the quality of metal accounts for 0.5% ~ 5.0% of catalyzer total mass, and the quality of molecular sieve modified element accounts for 1 ~ 3% of catalyzer total mass.
As preferably, the reaction pressure 1.2MPa in reactor two described in step c), temperature of reaction is 450 DEG C, and the volume ratio of hydrogen hydrocarbon is 8.
The beneficial effect that the present invention obtains is:
The metal-modified molecular sieve catalyst used in catalytic hydrogenation has selects isomerization to generate the function of p-Xylol in o-Xylol, m-xylene, ethylbenzene, thus can increasing yield of p-xylene effectively; In rectifying separation process, tower top, tower reactor cut boiling-point difference are about 20 DEG C, compared to direct separating mixed dimethyl system, reduce the difficulty of rectifying separation dramatically, reduce energy consumption and facility investment scale; The para-xylene product obtained has higher productive rate, makes the purity of the finished product higher through further purifying.
Embodiment
Below in conjunction with embodiment, illustrate the present invention further, following embodiment should be understood and be only not used in for illustration of the present invention and limit the scope of the invention.
Embodiment one
A method for separating paraxylene from xylene mixture, comprises the following steps:
A) shortening: xylol raw material and circulating hydrogen are entered reactor one simultaneously, control the reaction pressure 6.0MPa in reactor one, temperature of reaction is 250 DEG C, the volume ratio of hydrogen hydrocarbon is 500, under the effect of hydrogenation catalyst, xylol raw material carries out selectivity isomerization-hydrogenation reaction under hydro condition, generates the logistics containing Isosorbide-5-Nitrae-dimethyl cyclohexane after reaction; Hydrogenation catalyst is with the Y zeolite of Cr modification, and wherein Cr content is 5wt%;
B) rectifying separation: by step a) in generate containing 1, the logistics of 4-dimethyl cyclohexane is sent into rectifying separation unit and is carried out rectifying, and rectifying separation unit adopts plate distillation column, and logistics enters in the middle part of rectifying tower, 1,4-dimethyl cyclohexane flows out from tower top, and unreacted dimethylbenzene is got back to as raw material reactor after discharging at the bottom of still, arranges condenser at rectifying tower tower top, at the bottom of tower, reboiler is set, tower top service temperature is 90 DEG C, and working pressure is 0.1MPa, and tower reactor service temperature is 120 DEG C;
C) dehydrogenation reaction: after rectifying separation, 1,4-dimethyl cyclohexane enters reactor two, control reaction pressure 1.0MPa in reactor two, temperature of reaction is 400 DEG C, and hydrogen/hydrocarbon mol ratio is 5, under the effect of dehydrogenation catalyst, Isosorbide-5-Nitrae-dimethyl cyclohexane produces p-Xylol by dehydrogenation reaction, and dehydrogenation reaction used catalyst is the loaded catalyst containing transition metal Ni;
D) separating-purifying: p-Xylol step c) obtained carries out rectifying, isolates unreacted Isosorbide-5-Nitrae-dimethyl cyclohexane, obtains p-Xylol finished product, and isolated unreacted Isosorbide-5-Nitrae-dimethyl cyclohexane sends reactor two back to.
After measured, the purity of para-xylene product is 99.8%.
Embodiment two
A method for separating paraxylene from xylene mixture, comprises the following steps:
A) shortening: xylol raw material and circulating hydrogen are entered reactor one simultaneously, control the reaction pressure 8.0MPa in reactor one, temperature of reaction is 350 DEG C, the volume ratio of hydrogen hydrocarbon is 700, under the effect of hydrogenation catalyst, xylol raw material carries out selectivity isomerization-hydrogenation reaction under hydro condition, generates the logistics containing Isosorbide-5-Nitrae-dimethyl cyclohexane after reaction; Hydrogenation catalyst is with the Y zeolite of Mn modification, and wherein Mn content is 2wt%;
B) rectifying separation: by step a) in generate containing 1, the logistics of 4-dimethyl cyclohexane is sent into rectifying separation unit and is carried out rectifying, rectifying separation unit adopts plate distillation column, logistics enters in the middle part of rectifying tower, 1,4-dimethyl cyclohexane flows out from tower top, unreacted dimethylbenzene is got back to reactor as raw material after discharging at the bottom of still, at rectifying tower tower top, condenser is set, at the bottom of tower, reboiler is set, tower top service temperature is 110 DEG C, and working pressure is 0.5MPa, and tower reactor service temperature is 150 DEG C;
C) dehydrogenation reaction: after rectifying separation, 1,4-dimethyl cyclohexane enters reactor two, control reaction pressure 1.5MPa in reactor two, temperature of reaction is 500 DEG C, and hydrogen/hydrocarbon mol ratio is 10, under the effect of dehydrogenation catalyst, Isosorbide-5-Nitrae-dimethyl cyclohexane produces p-Xylol by dehydrogenation reaction, and dehydrogenation reaction used catalyst is the loaded catalyst containing Mo;
D) separating-purifying: p-Xylol step c) obtained carries out rectifying, isolates unreacted Isosorbide-5-Nitrae-dimethyl cyclohexane, obtains p-Xylol finished product, and isolated unreacted Isosorbide-5-Nitrae-dimethyl cyclohexane sends reactor two back to.
After measured, the purity of para-xylene product is 99.9%.
Embodiment three
A method for separating paraxylene from xylene mixture, comprises the following steps:
A) shortening: xylol raw material and circulating hydrogen are entered reactor one simultaneously, control the reaction pressure 7.0MPa in reactor one, temperature of reaction is 300 DEG C, the volume ratio of hydrogen hydrocarbon is 600, under the effect of hydrogenation catalyst, xylol raw material carries out selectivity isomerization-hydrogenation reaction under hydro condition, generates the logistics containing Isosorbide-5-Nitrae-dimethyl cyclohexane after reaction; Hydrogenation catalyst is with the Y zeolite of Zn and Cu modification, and wherein Zn content is 2wt%, Cu content is 3wt%;
B) rectifying separation: by step a) in generate containing 1, the logistics of 4-dimethyl cyclohexane is sent into rectifying separation unit and is carried out rectifying, rectifying separation unit adopts plate distillation column, logistics enters in the middle part of rectifying tower, 1,4-dimethyl cyclohexane flows out from tower top, unreacted dimethylbenzene is got back to reactor as raw material after discharging at the bottom of still, at rectifying tower tower top, condenser is set, at the bottom of tower, reboiler is set, tower top service temperature is 100 DEG C, and working pressure is 0.3MPa, and tower reactor service temperature is 135 DEG C;
C) dehydrogenation reaction: after rectifying separation, 1,4-dimethyl cyclohexane enters reactor two, control reaction pressure 1.2MPa in reactor two, temperature of reaction is 450 DEG C, and hydrogen/hydrocarbon mol ratio is 8, under the effect of dehydrogenation catalyst, Isosorbide-5-Nitrae-dimethyl cyclohexane produces p-Xylol by dehydrogenation reaction, and dehydrogenation reaction used catalyst is the loaded catalyst containing transition metal Pt and Zn;
D) separating-purifying: p-Xylol step c) obtained carries out rectifying, isolates unreacted Isosorbide-5-Nitrae-dimethyl cyclohexane, obtains p-Xylol finished product, and isolated unreacted Isosorbide-5-Nitrae-dimethyl cyclohexane sends reactor two back to.
After measured, the purity of para-xylene product is 99.8%.
Embodiment four
A method for separating paraxylene from xylene mixture, comprises the following steps:
A) shortening: xylol raw material and circulating hydrogen are entered reactor one simultaneously, control the reaction pressure 7.0MPa in reactor one, temperature of reaction is 300 DEG C, the volume ratio of hydrogen hydrocarbon is 600, under the effect of hydrogenation catalyst, xylol raw material carries out selectivity isomerization-hydrogenation reaction under hydro condition, generates the logistics containing Isosorbide-5-Nitrae-dimethyl cyclohexane after reaction; Hydrogenation catalyst is with the Y zeolite of Fe and Ni modification, and wherein Fe content is 4wt%, Ni content is 0.5wt%;
B) rectifying separation: by step a) in generate containing 1, the logistics of 4-dimethyl cyclohexane is sent into rectifying separation unit and is carried out rectifying, rectifying separation unit adopts plate distillation column, logistics enters in the middle part of rectifying tower, 1,4-dimethyl cyclohexane flows out from tower top, unreacted dimethylbenzene is got back to reactor as raw material after discharging at the bottom of still, at rectifying tower tower top, condenser is set, at the bottom of tower, reboiler is set, tower top service temperature is 100 DEG C, and working pressure is 0.3MPa, and tower reactor service temperature is 135 DEG C;
C) dehydrogenation reaction: after rectifying separation, 1,4-dimethyl cyclohexane enters reactor two, control reaction pressure 1.2MPa in reactor two, temperature of reaction is 450 DEG C, and hydrogen/hydrocarbon mol ratio is 8, under the effect of dehydrogenation catalyst, Isosorbide-5-Nitrae-dimethyl cyclohexane produces p-Xylol by dehydrogenation reaction, and dehydrogenation reaction used catalyst is the loaded catalyst containing transition metal Pd and Cu;
D) separating-purifying: p-Xylol step c) obtained carries out rectifying, isolates unreacted Isosorbide-5-Nitrae-dimethyl cyclohexane, obtains p-Xylol finished product, and isolated unreacted Isosorbide-5-Nitrae-dimethyl cyclohexane sends reactor two back to.
After measured, the purity of para-xylene product is 99.9%.
Technique means disclosed in the present invention program is not limited only to the technique means disclosed in above-mentioned embodiment, also comprises the technical scheme be made up of above technical characteristic arbitrary combination.It should be pointed out that for those skilled in the art, under the premise without departing from the principles of the invention, can also make some improvements and modifications, these improvements and modifications are also considered as protection scope of the present invention.
Claims (4)
1. the method for separating paraxylene from xylene mixture, comprises the following steps:
A) shortening: xylol raw material and circulating hydrogen are entered reactor one simultaneously, control the reaction pressure 6.0 ~ 8.0MPa in reactor one, temperature of reaction is 250 ~ 350 DEG C, the volume ratio of hydrogen hydrocarbon is 500 ~ 700, under the effect of hydrogenation catalyst, xylol raw material carries out selectivity isomerization-hydrogenation reaction under hydro condition, generates the logistics containing Isosorbide-5-Nitrae-dimethyl cyclohexane after reaction; Hydrogenation catalyst is metal-modified molecular sieve catalyst, and the metal in metal-modified molecular sieve catalyst is one or more in Zn, Cu, Ni, Mn, Cr and Fe; Molecular sieve is Y zeolite;
B) rectifying separation: by step a) in generate containing 1, the logistics of 4-dimethyl cyclohexane is sent into rectifying separation unit and is carried out rectifying, rectifying separation unit adopts plate distillation column, logistics enters in the middle part of rectifying tower, 1,4-dimethyl cyclohexane flows out from tower top, unreacted dimethylbenzene is got back to reactor as raw material after discharging at the bottom of still, at rectifying tower tower top, condenser is set, at the bottom of tower, reboiler is set, tower top service temperature is 90 ~ 110 DEG C, and working pressure is 0.1 ~ 0.5MPa, and tower reactor service temperature is 120 ~ 150 DEG C;
C) dehydrogenation reaction: after rectifying separation, 1,4-dimethyl cyclohexane enters reactor two, control reaction pressure 1.0 ~ 1.5MPa in reactor two, temperature of reaction is 400 ~ 500 DEG C, and hydrogen/hydrocarbon mol ratio is 5 ~ 10, under the effect of dehydrogenation catalyst, Isosorbide-5-Nitrae-dimethyl cyclohexane produces p-Xylol by dehydrogenation reaction, and dehydrogenation reaction used catalyst is containing one or more loaded catalyst in transition metal Pt, Pd, Ni, Mo, Cu or Zn;
D) separating-purifying: p-Xylol step c) obtained carries out rectifying, isolates unreacted Isosorbide-5-Nitrae-dimethyl cyclohexane, obtains p-Xylol finished product, and isolated unreacted Isosorbide-5-Nitrae-dimethyl cyclohexane sends reactor two back to.
2. the method for separating paraxylene from xylene mixture as claimed in claim 1, it is characterized in that, the reaction pressure 7.2MPa in reactor one described in step a), temperature of reaction is 300 DEG C, and the volume ratio of hydrogen hydrocarbon is 600.
3. the method for separating paraxylene from xylene mixture as claimed in claim 1, it is characterized in that, in the metal-modified molecular sieve catalyst described in step a), the quality of metal accounts for 0.5% ~ 5.0% of catalyzer total mass.
4. the method for separating paraxylene from xylene mixture as claimed in claim 1, it is characterized in that, the reaction pressure 1.2MPa in reactor two described in step c), temperature of reaction is 450 DEG C, and the volume ratio of hydrogen hydrocarbon is 8.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114534771A (en) * | 2022-03-03 | 2022-05-27 | 大庆亿鑫化工股份有限公司 | Isomerization catalyst of mixed xylene and separation method of o-xylene |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114534771A (en) * | 2022-03-03 | 2022-05-27 | 大庆亿鑫化工股份有限公司 | Isomerization catalyst of mixed xylene and separation method of o-xylene |
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Application publication date: 20160316 |