CN103030516A - Purification method of coking xylene - Google Patents
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- CN103030516A CN103030516A CN2013100031857A CN201310003185A CN103030516A CN 103030516 A CN103030516 A CN 103030516A CN 2013100031857 A CN2013100031857 A CN 2013100031857A CN 201310003185 A CN201310003185 A CN 201310003185A CN 103030516 A CN103030516 A CN 103030516A
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Abstract
The invention provides a purification method of coking xylene. The purification method comprises the following steps: (1) rectifying a raw material coking xylene; and (2) enabling the rectified coking xylene to sequentially pass through a modified and activated 13X molecular sieve, a silica-gel molding adsorbent and a ZSM (Zeolite Socony Mobil)-5 molecular sieve molding adsorbent in the form of liquid phase. According to the purification method of the coking xylene, the contents of benzene, toluene and ethylbenzene in the raw material coking xylene can be reduced after rectification and adsorption treatments on the coking xylene, and impurities including sulfides, nitrides, water, trace tar heavy components, solid residues and the like in the raw material coking xylene can be removed efficiently, as a result, the quality of the coking xylene can be improved.
Description
Technical field
The invention belongs to chemical field, in particular to the method for purification of coking xylene, mainly is to remove trace impurity in the coking xylene with the method for rectifying, absorption, improves the purity of coking xylene.
Background technology
Dimethylbenzene is a kind of important Organic Chemicals, is widely used in the industries such as coating, resin, dyestuff, printing ink as solvent; Be used for the industries such as medicine, explosive, agricultural chemicals as synthon or solvent; Also can be used as high octane gasoline component.In addition, dimethylbenzene can also be used for removing the pitch of vehicle body; Hospital pathology department mainly uses preparation; Be mainly used in dehydration, dewaxing.
Mainly exist with petroleum xylene and coking xylene product form in the market.The two originates different, and petroleum xylene is the product in the petroleum refining process, and coking xylene is to extract the product that obtains in the coal tar process from coal tar.Foreign matter content is few, quality is higher than the characteristics such as coking xylene because petroleum xylene has for a long time, and the petroleum xylene purposes is comparatively extensive.Coking xylene derives from coal tar, and dopant species is more, causes quality low, and purposes is narrower.The insider generally believes: because impurity is easy to make commercial catalysts to poison in the coking xylene, so can not be used for the production of downstream high value added product, therefore, the application of coking xylene is very limited.Product is compared with the same period on the market, low 500～1000 yuan/tons of the price of the cost ratio petroleum xylene of the coking xylene of same level.
Along with the development of chemical industry, the progress of chemical analysis means is for the mass discrepancy that solves coking xylene and petroleum xylene provides possibility in recent years.Especially in recent years international situation is intricate, and oil supply is unstable, and price increase significantly improves take the Chemicals cost of oil as the basis, and the quality that improves coking xylene can remedy the gaps in market of petroleum xylene, promotes the progress of coal chemical technology.On the one hand, China's oil self interdependency in short supply, external is high, can take full advantage of and have abundant coal resources; On the other hand, the quality gap of coking xylene and petroleum xylene is industry issue, solves this problem by development new technologies, can reduce the social running cost of commercial xylene industry, has very real meaning.
Summary of the invention
Technical problem to be solved by this invention is deimpurity problem in the coking xylene, mainly be by rectifying, absorbing process, grope deimpurity each physical parameter, finally make high-purity dimethylbenzene quality product of obtaining surpass the standard of petroleum xylene top grade product, satisfy the standard of dimethylbenzene analytical pure GB/T16494-1996.
Therefore, the method for purification that the purpose of this invention is to provide a kind of coking xylene.Described method can improve the purity of coking xylene with the impurity in the lower cost removal coking xylene, widens the product application scope.
According to an aspect of the present invention, provide a kind of method of purification of coking xylene, said method comprising the steps of:
Step 1): make the raw material coking xylene through rectifying; With
Step 2): make coking xylene after the rectifying with liquid form successively by through the 13X of modified active molecular sieve, silica gel formed absorbent and ZSM-5 molecular sieve formed absorbent.
Among the present invention, after the rectifying of coking xylene process, the adsorption treatment, can reduce preferably the content of benzene in the raw material coking xylene, toluene, ethylbenzene, can effectively remove the impurity such as sulfide in the raw material coking xylene, nitride, moisture, the restructuring of micro-tar minute, solid residue, thereby improve the quality of coking xylene.
Among the present invention, described coking xylene can be the technical grade coking xylene, and quality will reach the requirement of GB/T2285-93 salable product.
Among the present invention, preferably, in the step 1), make the raw material coking xylene under normal pressure, carry out batch fractionating, wherein, reflux ratio is 2.0～6.0, is preferably 5.0, and the cat head service temperature is 132～138 ℃, be preferably 136 ℃, the tower reactor service temperature is 180～190 ℃, is preferably 190 ℃.
Among the present invention, preferably, in step 2) in, describedly can carry out by the following method modification and activation through the 13X of modified active molecular sieve, concrete experimental procedure is as follows:
Step a): the 13X molecular sieve is pulverized rear screening, get 40-60 order grade.
Step b): make the 13X molecular sieve that obtains in the step a) and contain KCl and BaCl
2The aqueous solution in the microwave reaction stove, carry out ion-exchange.For example, be specially: make the 13X molecular sieve 10g that obtains in the step a) and 0.32mol/LKCl, the 0.18mol/LBaCl of 133ml
2Solution stirs 1～1.5h in the microwave reaction stove, realize ion-exchange.
Step c): the roasting of wetting is processed to the 13X molecular sieve that obtains in the step b).For example, be specially: the deionized water gasification is passed in the tube furnace of placing the 13X molecular sieve, keep 110 ℃ of tube furnace steady temperatures, keep 3～5h, the temperature rise rate with 2 ℃/min carries out temperature programming again, until temperature reaches 220 ℃, keep 2h, finish wet roasting and process.
Step d): the 13X molecular sieve that the wet roasting of the process that obtains in the step c) is processed with contain KCl and BaCl
2The aqueous solution in the microwave reaction stove, carry out ion-exchange, then dryly obtain the molecular sieve through the 13X of modification.For example, be specially: the 0.32mol/LKCl, the 0.18mol/LBaCl that the 13X molecular sieve 10g of the wet roasting processing of the process that obtains in the step c) are put into 133ml
2In the solution, in microwave oven, fully stir 1～1.5h, suction filtration, the 13X molecular sieve that obtains obtains the molecular sieve through the 13X of modification at 120 ℃ of lower dry 3～6h.
Step e): put into tube furnace through the 13X of modification molecular sieve with what obtain in the step d), pass into 150～200 ℃, preferred 180 ℃ hot nitrogen and purge 2～3h, continue to pass into the carbon dioxide through vitriol oil washing after finishing, keep the interior temperature of tube furnace at 60～80 ℃, obtain described through the 13X of modified active molecular sieve.
Among the present invention, preferably, in step 2) in, described silica gel formed absorbent can make by the following method:
A) activation treatment of silica gel:
With dehydrated alcohol flushing silica gel powder (preferred 5～7 times), drying is 2～3 hours under 110～150 ℃; Then dried silica gel is put into the HAc-NaAc solution of PH=6～7, in 25～40 ℃ of lower vibrations 1 ~ 5 hour (preferred 2h), left standstill the rear pure water rinsing (preferred 5～8 times) of using, again 120 ℃ of lower oven dry; Put at last retort furnace, 200～230 ℃ of lower bakings 2～3 hours, make activated silica gel.
B) moulding of activated silica gel:
Get a) activated silica gel of middle preparation of above-mentioned steps, by weight, amount based on activated silica gel, adding auxiliary material sesbania powder (5～8%), active oxidation aluminium powder form (7～9%), tetramethyl-sodium cellulosate (3～5%) and concentration is 10～12% salpeter solutions (3～6%), carry out extrusion moulding, 120～150 ℃ of lower oven dry 2～3 hours, 230～260 ℃ of lower roastings 4～6 hours, obtain at last the silica gel formed absorbent.
Among the present invention, preferably, in step 2) in, described ZSM-5 molecular sieve formed absorbent can make by the following method:
Behind washing with acetone ZSM-5 molecular sieve (preferred 3～5 times), 80 ℃ of dryings (preferred 2～3 hours) were soaked molecular sieve 18～20 hours in saturated aqueous common salt, washed with water clean; Then, be the flushing of 5～10% sodium hydroxide solution with concentration, remove inorganic impurity wherein, again with water rinse to neutral; At last, be the flushing of 5～8% hydrochloric acid with concentration, remove inorganic impurity wherein, water is flushed to neutrality again, makes thus the ZSM-5 molecular sieve formed absorbent.
Among the present invention, preferably, described 13X molecular sieve can be the white amorphous powder that 100-200 order chromatography is used.
Among the present invention, preferably, described silica gel can be the white glass shape amorphous powder that 200-300 order column chromatography is used.
Among the present invention, preferably, described ZSM-5 molecular sieve can be the globe that particle diameter is 2～3mm.
Among the present invention, preferably, can be respectively charged in the different adsorption columns through the 13X of modified active molecular sieve, three kinds of sorbent materials of silica gel formed absorbent and ZSM-5 molecular sieve formed absorbent above-mentioned, will pass through through the 13X of modified active molecular sieve, silica gel formed absorbent and ZSM-5 molecular sieve formed absorbent successively with liquid form after the rectifying of raw material coking xylene.Wherein, accompanying hot temperature is 40～100 ℃, and preferred 60～80 ℃, most preferably 75 ℃, the pressure of raw material coking xylene is 0.2～1.0MPa, preferred 0.2～0.6MPa, and 0.5MPa most preferably, the liquid air speed is 1.0～3.0h
-1, preferred 1.2～2.5h
-1, 2.3h most preferably
-1
Among the present invention, except special appointment, all per-cents all are weight percentage.
The inventor finds that by research dopant species is many in the raw material coking xylene, mainly contains the vinylbenzene of benzene, toluene, ethylbenzene and the two keys of band or with the unsaturated compound of the phenylacetylene of triple bond; Organic contains S, N compound, and inorganic states contains S, N compound; The material of easy carbonization; Free H
+, OH
-Therefore the polymorphic type such as ion, moisture impurity adopt first rectifying to reduce benzene, toluene, ethylbenzene content, is very necessary by the continuous removal of impurities of sorbent material again.The raw material coking xylene passes through through the 13X of modified active molecular sieve, in the raw material exchanged dose of the anionic species such as sulfur-bearing, nitrogen impurity adsorb, and the silica gel formed absorbent utilizes chromatographic theory can hold back polarity greatly and the material of some easy carbonizations, the ZSM-5 molecular sieve formed absorbent is because large specific surface area, its micropore surface adsorptive power is very strong, can adsorb hydro carbons in the raw material coking xylene (such as C
8H
16, C
8H
14Deng).Therefore, foreign matter content obviously reduces in the coking xylene, thereby reaches the purpose of purification.
Benzene, toluene, the equal decrease of ethylbenzene content in the high-purity dimethylbenzene product that obtains by method of the present invention, other trace impurity also significantly reduces, indices is the standard pure above the petroleum xylene top grade all, thereby reaches the purpose of purifying coking xylene.The technical grade coking xylene derives from tar stock, and foreign matter content is of a great variety, and its purposes is very limited, and present method can improve the purity of coking xylene with the impurity in the lower cost removal technical grade coking xylene, widens the product application scope.
Embodiment
Preparation Example
Material and reagent:
Instrument:
The modified active of Preparation Example 113X molecular sieve
1, the 13X molecular sieve is pulverized rear screening, got 40-60 order grade;
2, make the 13X molecular sieve 10g that obtains in the step 1 and 0.32mol/LKCl, the 0.18mol/LBaCl of 133ml
2Solution stirs 1h in the microwave reaction stove, realize ion-exchange;
3, the roasting of wetting is processed to the 13X molecular sieve that obtains in the step 2: the deionized water gasification is passed in the tube furnace of placing the 13X molecular sieve, keep 110 ℃ of tube furnace steady temperatures, keep 3h, temperature rise rate with 2 ℃/min carries out temperature programming again, until temperature reaches 220 ℃, keep 2h, finish wet roasting and process;
4, the 13X molecular sieve 10g that the wet roasting of the process that obtains in the step 3 is processed puts into 0.32mol/LKCl, the 0.18mol/LBaCl of 133ml
2In the solution, in microwave oven, fully stir 1h, suction filtration, 120 ℃ of lower dry 3h obtain the molecular sieve through the 13X of modification;
5, in the activation step 3 obtain through the 13X of modification molecular sieve: will put into tube furnace through the 13X molecular sieve of modification, and pass into 180 ℃ of hot nitrogens and purge 2h.Continue to pass into the carbon dioxide through vitriol oil washing after finishing, keep the interior temperature of tube furnace at 60 ℃, obtain through the 13X of modified active molecular sieve stand-by.
The preparation of Preparation Example 2 silica gel formed absorbents
A) activation treatment of silica gel: wash the silica gel powder 5 times with dehydrated alcohol, lower dry 2 hours at 130 ℃; Then dried silica gel is put into the HAc-NaAc solution of PH=6～7,25 ℃ of lower vibrations 2 hours, left standstill rear pure water rinsing 6 times of using, again 120 ℃ of lower oven dry; Put at last retort furnace, 230 ℃ of lower bakings 2 hours, make the silica gel of activation, it is for subsequent use to put into sample sack after the cooling.
B) moulding of activated silica gel: by weight, take by weighing a) the activated silica gel 500g of middle preparation of above-mentioned steps, weight based on activated silica gel, add auxiliary material sesbania powder (5%), active oxidation aluminium powder form (7%), tetramethyl-sodium cellulosate (3%) and 10% salpeter solution (3%), carry out extrusion moulding, 120 ℃ of lower oven dry 2 hours, 260 ℃ of lower roastings 4 hours, obtain at last the silica gel formed absorbent.
The preparation of the molecular sieve molded sorbent material of Preparation Example 3ZSM-5
Behind washing with acetone ZSM-5 molecular sieve 4 times, 80 ℃ of dryings 2 hours were soaked molecular sieve 20 hours in saturated aqueous common salt, use the deionized water wash clean; Then, be 10% sodium hydroxide solution flushing with 2～3 times of pending ZSM-5 molecular sieve volume and concentration, remove inorganic impurity wherein, again with rinsed with deionized water to neutral; At last, be 8% hydrochloric acid flushing with processing 2～3 times of ZSM-5 molecular sieve and concentration, remove inorganic impurity wherein, be flushed to neutrality with deionized water again, make thus the ZSM-5 molecular sieve formed absorbent.
Embodiment
The rectifying of embodiment 1-10 coking xylene
Take xylene content more than or equal to 90.0% coking xylene (available from rising sun sun Chemical Group) as raw material, make raw material pass through stainless steel with 3mm ﹡ 3mm
Ring carries out batch fractionating for the rectifier unit of filler, under normal pressure, operate, reflux ratio is 2.0～6.0, the cat head service temperature is 132～138 ℃, the tower reactor service temperature is 180～190 ℃, the dimethylbenzene product cut receives by the cooling of rectifier unit condenser, enters the product receptor by thrust-augmenting nozzle, and xylene content sees Table 1 in the concrete technology condition of each embodiment and the product.
Embodiment 1-10 Instrumental and correlation parameter:
The content of the dimethylbenzene before and after the concrete technology condition of table 1. embodiment 1-10 and the processing, toluene, benzene, ethylbenzene.
Embodiment 11-22 liquid phase adsorption method is removed the impurity in the coking xylene
Fill respectively above-mentioned three kinds of sorbent materials in three adsorption columns, order is: the ZSM-5 molecular sieve formed absorbent that silica gel formed absorbent and the 84.9g Preparation Example 3 through the 13X of modified active molecular sieve, 2 preparations of 104.7g Preparation Example of 90.3g Preparation Example 1 preparation prepares.Press the processing condition among the embodiment 10-22, the dimethylbenzene that embodiment 7 rectifying are obtained passes through above-mentioned each sorbent material successively with liquid form.Xylene content before and after the concrete technology condition of each embodiment and the processing sees Table 2.
Embodiment 11-22 Instrumental and correlation parameter:
The dimethylbenzene that embodiment 7 rectifying are obtained enters adsorption column by micro-sampling pump (Series II), puts in order successively through three adsorption columns of above-mentioned three kinds of sorbent materials are housed, wherein by above-mentioned sorbent material:
The liquid air speed remains on 1.2～2.5h
-1Adsorption column is by thermostat water bath circulating hot water companion warm, and temperature remains on 60～80 ℃; The adsorption column internal pressure remains on 0.2～0.6Mpa.Press embodiment 11-22 different technology conditions and flow out, the product xylene content that obtains sees Table 2.
The concrete technology condition of table 2. embodiment 11-22 and each index of dimethylbenzene product of processing front and back:
High-purity dimethylbenzene product evaluation, employing petroleum xylene top grade is pure to combine with GB analytical pure dimethylbenzene standard, and detected result sees Table 3.
Table 3.
Illustrate: petroleum xylene top grade product standard, state label GB3407-90.
GB dimethylbenzene analytical pure standard, state label GB/T16494-1996.
As can be seen from the above data, the present invention is directed to the deimpurity problem of coking xylene, developed the impurity-removing method of a kind of first rectifying, rear absorption.Find out each physical parameter of rectifying, adsorption-edulcoration matter, finally made high-purity dimethylbenzene quality product surpass the petroleum xylene specification of quality, reached the requirement of GB analytical pure dimethylbenzene.
Claims (10)
1. the method for purification of a coking xylene said method comprising the steps of:
Step 1): make the raw material coking xylene through rectifying; With
Step 2): make coking xylene after the rectifying with liquid form successively by through the 13X of modified active molecular sieve, silica gel formed absorbent and ZSM-5 molecular sieve formed absorbent.
2. method according to claim 1, in the step 1), make the raw material coking xylene under normal pressure, carry out batch fractionating, wherein, reflux ratio is 2.0～6.0, is preferably 5.0, the cat head service temperature is 132～138 ℃, be preferably 136 ℃, the tower reactor service temperature is 180～190 ℃, is preferably 190 ℃.
3. method according to claim 1 and 2 is in step 2) in, describedly make by the following method through the 13X of modified active molecular sieve:
Step a): the 13X molecular sieve is pulverized rear screening, get 40-60 order grade;
Step b): make the 13X molecular sieve that obtains in the step a) and contain KCl and BaCl
2The aqueous solution in the microwave reaction stove, carry out ion-exchange;
Step c): the roasting of wetting is processed to the 13X molecular sieve that obtains in the step b);
Step d): the 13X molecular sieve that the wet roasting of the process that obtains in the step c) is processed with contain KCl and BaCl
2The aqueous solution in the microwave reaction stove, carry out ion-exchange, then dryly obtain the molecular sieve through the 13X of modification;
Step e): put into tube furnace through the 13X of modification molecular sieve with what obtain in the step d), pass into 150～200 ℃ of hot nitrogens and purge 2～3h, continue to pass into the carbon dioxide through vitriol oil washing after finishing, keep the interior temperature of tube furnace at 60～80 ℃, obtain described through the 13X of modified active molecular sieve.
4. method according to claim 3, step b) comprises: make the 13X molecular sieve 10g that obtains in the step a) and 0.32mol/L KCl, the 0.18mol/LBaCl of 133ml
2Solution stirs 1～1.5h in the microwave reaction stove, realize ion-exchange.
5. method according to claim 3, step c) comprises: the deionized water gasification is passed in the tube furnace of placing the 13X molecular sieve, keep 110 ℃ of tube furnace steady temperatures, keep 3～5h, temperature rise rate with 2 ℃/min carries out temperature programming again, until temperature reaches 220 ℃, keep 2h, finish wet roasting and process.
6. method according to claim 3, step d) comprises: the 13X molecular sieve 10g that the wet roasting of the process that obtains in the step c) is processed puts into 0.32mol/LKCl, the 0.18mol/LBaCl of 133ml
2In the solution, in microwave oven, fully stir 1～1.5h, suction filtration, the 13X molecular sieve that obtains obtains the molecular sieve through the 13X of modification at 120 ℃ of lower dry 3～6h.
7. method according to claim 1 and 2 is in step 2) in, described silica gel formed absorbent makes by the following method:
A) activation treatment of silica gel: with dehydrated alcohol flushing silica gel powder, drying is 2～3 hours under 110～150 ℃; Then dried silica gel is put into the HAc-NaAc solution of PH=6～7,25～40 ℃ of lower vibrations 1 ~ 5 hour, left standstill the rear pure water rinsing of using, again 120 ℃ of lower oven dry; Put at last retort furnace, 200～230 ℃ of lower bakings 2～3 hours, make activated silica gel.
B) moulding of activated silica gel: get a) activated silica gel of middle preparation of above-mentioned steps, by weight, amount based on activated silica gel, sesbania powder, 7～9% active oxidation aluminium powder form, 3～5% tetramethyl-sodium cellulosate and 3～6% the concentration of adding auxiliary material 5～8% are 10～12% salpeter solutions, carry out extrusion moulding, 120～150 ℃ of lower oven dry 2～3 hours, 230～260 ℃ of lower roastings 4～6 hours, obtain at last the silica gel formed absorbent.
8. method according to claim 1 and 2 is in step 2) in, described ZSM-5 molecular sieve formed absorbent makes by the following method:
Behind the washing with acetone ZSM-5 molecular sieve, 80 ℃ of dryings were soaked molecular sieve 18～20 hours in saturated aqueous common salt, washed with water clean; Then, be the flushing of 5～10% sodium hydroxide solution with concentration, remove inorganic impurity wherein, again with water rinse to neutral; At last, be the flushing of 5～8% hydrochloric acid with concentration, remove inorganic impurity wherein, water is flushed to neutrality again, makes thus the ZSM-5 molecular sieve formed absorbent.
9. method according to claim 1 and 2, in step 2) in, be respectively charged in the different adsorption columns through the 13X of modified active molecular sieve, three kinds of sorbent materials of silica gel formed absorbent and ZSM-5 molecular sieve formed absorbent above-mentioned, will pass through through the 13X of modified active molecular sieve, silica gel formed absorbent and ZSM-5 molecular sieve formed absorbent successively with liquid form after the rectifying of raw material coking xylene.
10. method according to claim 9, wherein, accompanying hot temperature is 40～100 ℃, preferred 60～80 ℃, most preferably 75 ℃; The pressure of raw material coking xylene is 0.2～1.0MPa, preferred 0.2～0.6MPa, most preferably 0.5MPa; The liquid air speed is 1.0～3.0h
-1, preferred 1.2～2.5h
-1, 23h most preferably
-1
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| CN104230619B (en) * | 2013-06-17 | 2016-12-28 | 中国石油化工股份有限公司 | The method of aromatic hydrocarbons deep purifying |
| CN104275215A (en) * | 2013-07-09 | 2015-01-14 | 中国石油化工股份有限公司 | Microwave continuous ion exchange method of molecular sieve |
| CN104276921A (en) * | 2013-07-09 | 2015-01-14 | 中国石油化工股份有限公司 | Desulphurization denitrification method for aromatic hydrocarbons |
| CN104276582A (en) * | 2013-07-09 | 2015-01-14 | 中国石油化工股份有限公司 | Rapid ion exchange method of molecular sieve |
| CN104276921B (en) * | 2013-07-09 | 2016-04-13 | 中国石油化工股份有限公司 | The method of aromatizing and desulfurizing denitrogenation |
| CN107915567A (en) * | 2016-10-08 | 2018-04-17 | 中国石油化工股份有限公司 | The method that polar compound is removed from the aromatic raw material containing polar compound |
| CN113511770A (en) * | 2021-09-13 | 2021-10-19 | 江苏飞亚化学工业集团股份有限公司 | Sewage treatment system in xylene course of working |
| CN114315502A (en) * | 2021-12-31 | 2022-04-12 | 南京化学试剂股份有限公司 | Method for purifying low-moisture high-purity xylene |
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