CN103965962A - Method for preparing benzylamine and clean fuel from dephenolized phenol oil - Google Patents
Method for preparing benzylamine and clean fuel from dephenolized phenol oil Download PDFInfo
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- CN103965962A CN103965962A CN201410212307.8A CN201410212307A CN103965962A CN 103965962 A CN103965962 A CN 103965962A CN 201410212307 A CN201410212307 A CN 201410212307A CN 103965962 A CN103965962 A CN 103965962A
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Abstract
The invention relates to a method for preparing benzylamine and clean fuel from dephenolized phenol oil, belonging to the field of environmental protection and energy technologies. The method is characterized by comprising the steps of mixing the dephenolized phenol oil and hydrogen, introducing into a hydrogenation tower, and performing low-temperature hydrogenation to remove cyanobenzene and diolefin in the dephenolized phenol oil; introducing the dephenolized phenol oil into a water washing tower after hydrogenation, performing room-temperature operation in the water washing tower, introducing a benzylamine aqueous solution at the lower layer of the tower bottom of the water washing tower into a rectifying tower, charging materials in the tower, discharging water from the tower top of the rectifying tower, circulating to enter the water washing tower, and discharging high-purity benzylamine from the tower bottom of the rectifying tower; after water washing, pressurizing the dephenolized phenol oil, mixing with hydrogen, then entering a hydrogenation refining tower, performing hydrogenation and quality improvement, removing monoene compounds by virtue of mono-olefine hydrogenation saturated reaction, and meanwhile, performing desulfurization, denitrification and pectin removal to produce an odor-free and high-quality gasoline and diesel oil mixture, and then distilling to obtain gasoline and diesel oil distillates. The method disclosed by the invention is simple in process and good in catalyst activity and stability, and has good economic benefits and industrial application prospects.
Description
Technical field
The invention belongs to environment protection and energy technology field, relate to the method for a kind of removal phenol carbolic oil benzene methanamine processed and clean fuel.
Background technology
In Coal Chemical Industry process, coal tar is as one of staple product of coking industry, and its output accounts for 3%～4% of shove charge coal, and it forms very complicated, produces about 15.00Mt per year.Cut before 170 ℃, coal tar is light oil; The cut of 170～210 ℃ is mainly carbolic oil.Removal phenol carbolic oil refers to that carbolic oil sloughed the oil after phenol by sodium hydroxide, and the solution after sodium hydroxide dephenolize, sodium phenolate solution, is the raw material of extraction crude phenols, carries out refining of crude phenol after extracting again.In coal tar, the content of removal phenol carbolic oil is in 3% left and right, and the fraction conventionally cutting in the actual course of processing is all greater than 3%, removal phenol carbolic oil approximately contains the cyanobenzene of 2%-3%, the existence of cyanobenzene not only increases hydrorefined hydrogen consumption, increase production cost, and to the toxic effect of Hydrobon catalyst.Cyanobenzene can Hydrogenation for benzylamine, benzylamine is a kind of chemicals of high added value, can be used as the intermediate of dyestuff, medicine and polymkeric substance.At present, in technique, the processing of removal phenol carbolic oil is roughly had to following several means: the first is back to mix in mixing oil, but the price of mixing oil is lower than the price of removal phenol carbolic oil, production added value is low.The second treatment process is to rebuild a set of rectifier unit, by removal phenol carbolic oil re-distillation, can reclaim a part of naphthalene, but low to removal phenol carbolic oil overall utilization rate.The third is as intermediates direct marketing by removal phenol carbolic oil.Above method does not all have recycling to removal phenol carbolic oil.
For abundant removal phenol carbolic oil recycling problem, according to the chemical constitution of removal phenol carbolic oil and character, we have successfully developed the novel process that high-purity benzene methylamine and clean fuel are produced in removal phenol carbolic oil liquid-phase hydrogenatin-washing-rectifying-hydrofining-distillation.Removal phenol carbolic oil is prepared high-purity benzene methylamine through liquid-phase hydrogenatin, washing and rectifying, end temperature liquid-phase hydrogenatin is removed in removal phenol carbolic oil diolefin and is made cyanobenzene hydrogenation generate benzene methanamine, benzene methanamine solution is prepared high-purity benzene methylamine through rectifying, and the catalyzer that hydrogenation is used is metal supported catalyst; After washing, removal phenol carbolic oil enters hydrofining tower, carry out hydrogenation upgrading, the catalyzer that hydrofining is used is sulfide catalyst, by monoolefin hydrogenation saturated reaction, remove monoene compound, and desulfurization, nitrogen are de-, produce to obtain free from extraneous odour, petrol and diesel oil mixing oil that quality is high except colloid, then obtain gasoline and diesel oil distillate oil through distillation.In liquid-phase hydrogenatin-washing-rectifying-hydrofining-distillation, without the three wastes, producing, is the process of green a, recycling.Following known technology, all comes with some shortcomings:
Chinese patent, publication number: CN103589466A, having introduced a kind of removal phenol carbolic oil by coal chemical technology is applied in oil fuel, utilized the high characteristic of allotment of removal phenol carbolic oil, be prepared into that a kind of production cost is low, oxidation stability is high, benzene content is low, the method of the oil fuel of normal viscosity, but the quality of oil fuel is low, removal phenol carbolic oil added value utilization ratio is low, causes the wasting of resources.
Summary of the invention
The method that the invention provides a kind of removal phenol carbolic oil benzene methanamine processed and clean fuel is low for removal phenol carbolic oil conversion process added value, secondary pollution and the problem such as catalyst life is short, take high-purity benzene methylamine and high-quality petrol and diesel oil is target product, realize removal phenol carbolic oil recycling, make the energy-conservation and environmental protection of production process, avoided secondary pollution, the extending catalyst life-span.Specifically, the present invention prepares high-purity benzene methylamine by removal phenol carbolic oil through liquid-phase hydrogenatin, washing and rectifying, removal phenol carbolic oil is removed diolefin and cyanobenzene hydrogenation generation benzene methanamine in removal phenol carbolic oil through high pressure low temperature liquid-phase hydrogenatin, the benzene methanamine aqueous solution is prepared high-purity benzene methylamine through rectifying, and the catalyzer that hydrogenation is used is metal supported catalyst; After washing, removal phenol carbolic oil enters hydrofining tower, carry out hydrogenation upgrading, the catalyzer that hydrofining is used is sulfide catalyst, by monoolefin hydrogenation saturated reaction, remove monoene compound, and desulfurization, nitrogen are de-, produce to obtain free from extraneous odour, high-quality petrol and diesel oil mixing oil except colloid, then obtain gasoline and diesel oil distillate oil through distillation.The present invention has improved removal phenol carbolic oil utilization ratio, has increased its added value, energy-conservation of consumption reduction, extending catalyst life-span, and flow process is simple and reduce investment outlay.
Technical scheme of the present invention is as follows:
Removal phenol carbolic oil and hydrogen are mixed into hydrogenation tower, carry out low temperature hydrogenation and remove cyanobenzene and diolefin in removal phenol carbolic oil, feeding temperature 140-180 ℃, hydrogen partial pressure 4-8MPa, volume space velocity 0.5-1.0h
-1, hydrogen to oil volume ratio 400-600:1; Hydrogenation catalyst is metal supported catalyst; After hydrogenation, removal phenol carbolic oil enters water wash column, water wash column ambient operation, water and removal phenol carbolic oil volume ratio 0.5-2, under water wash column tower, the layer benzene methanamine aqueous solution enters rectifying tower, charging in tower, and rectifying tower ejects water, beat and be recycled into water wash column, at the bottom of rectifying tower, go out high-purity benzene methylamine; After hydrogenation, removal phenol carbolic oil is mixed into hydrofining tower through washing, pressurization and hydrogen, carries out hydrogenation upgrading, feeding temperature 320-360 ℃, hydrogen partial pressure 6-8MPa, volume space velocity 0.4-1.0h
-1, hydrogen to oil volume ratio 600-1200:1; The catalyzer that hydrogenation is used is sulfide catalyst; Distillate after hydrofining, through air distillation, cuts into gasoline (<180 ℃) and diesel oil (>180 ℃) according to recovered temperature.Technique scheme can continuous operation.
Hydrogenation catalyst in the present invention is metal supported catalyst, and metal catalyst is that metal supported catalyst is Pd, PtPd, Co, Ni, CoMo or NiMo; Carrier is SiO
2, Al
2o
3, TiO
2, SiO
2-Al
2o
3or Al
2o
3-TiO
2.The Main Function of catalyzer is under low hydrogen/gasoline ratio and high-speed, low temperature liquid phase hydrogenation is removed diolefin in removal phenol carbolic oil, prevent its polymerization in hydrofining tower, increase the Hydrobon catalyst life-span, and make the cyanobenzene hydrogenation in removal phenol carbolic oil generate benzene methanamine.The Hydrobon catalyst that hydrofining tower is used for loading type sulfide catalyst be NiMo, NiW, CoMo, CoW, NiMoW or CoMoW, the Main Function of catalyzer is that monoolefin hydrogenation saturated reaction removes monoene compound, and desulfurization, nitrogen are de-, except colloid; Carrier is SiO
2-Al
2o
3or Al
2o
3-TiO
2.
By removal phenol carbolic oil of the present invention, through liquid-phase hydrogenatin, washing and rectifying, produce and obtain benzene methanamine purity >98.5%; Removal phenol carbolic oil through liquid-phase hydrogenatin, washing, hydrofining, distill the yield of gasoline fraction (<180 ℃) at 85-90%, octane value is 85-92, density 0.70-0.75g/cm
3, can be used as the blend component of gasoline.The yield of diesel oil distillate (>180 ℃) is at 10-15%, and cetane value is 45, density 0.82-0.84g/cm
3, can be used as diesel oil.
Liquid-phase hydrogenatin of the present invention, water washing process, rectifying, hydrogenation upgrading, air distillation adopt the mode of operate continuously, flexible operation, easy.Adopt liquid-phase hydrogenatin, washing and rectifying to prepare high-purity benzene methylamine, and under low hydrogen/gasoline ratio and high-speed, low temperature liquid phase hydrogenation is removed diolefin in removal phenol carbolic oil, prevent its polymerization in hydrofining tower, increase the Hydrobon catalyst life-span, and make the cyanobenzene hydrogenation in removal phenol carbolic oil generate high valuable chemicals benzene methanamine.After washing, removal phenol carbolic oil, through hydrogenation upgrading, removes monoene compound by monoolefin hydrogenation saturated reaction, and desulfurization, nitrogen are de-, produce to obtain free from extraneous odour, high-quality petrol and diesel oil mixing oil except colloid, then obtains gasoline and diesel oil distillate oil through distillation.The present invention can obtain high purity high added value benzene methanamine and high-quality clean fuel oil, thereby realizes the recycling of removal phenol carbolic oil.
Accompanying drawing explanation
Accompanying drawing is process flow diagram of the present invention.
In figure: 1 hydrogenation tower; 2 water wash columns; 3 rectifying tower; 4 hydrofining towers; 5 distillation towers.
Embodiment
Below in conjunction with technical scheme and accompanying drawing, describe specific embodiments of the invention in detail.
Embodiment 1
Removal phenol carbolic oil is injected to hydrogenation tower, and hydrogenation catalyst is loading type Pd, PtPd, Co, Ni, CoMo or NiMo metal catalyst.Carrier adopts SiO
2-Al
2o
3, specific surface area is at 400-500m
2/ g, pore volume is at 2-3cm
3/ g, most probable pore size distribution is at 2-4nm and 10-15nm.Metal precursor adopts respectively palladium or Palladous nitrate, palladium and Platinic chloride or Palladous nitrate and methyl ethyl diketone platinum, Cobaltous diacetate or Jing Ti/Bao Pian COBALT NITRATE CRYSTALS/FLAKES, acetic acid pinch or nickelous nitrate, Jing Ti/Bao Pian COBALT NITRATE CRYSTALS/FLAKES and ammonium molybdate, nickelous nitrate and ammonium molybdate.Adopt equi-volume impregnating to prepare load type metal catalyst through dipping-dry-roasting-steps such as reduction.For metal Pd metal loading at 3-10%; Loading difference 2-8% and 0.5-2% for metal bimetal PtPd Pt metal and Pd; For metal Co and Ni metal loading at 20-40%; For CoMo and NiMo metal Co and Ni, be supported on 15-25%, metal M o is supported on 5-15%.Following table 1 is shown in reaction process condition and product property.
As shown in Table 1, removal phenol carbolic oil is through the de-diene of high pressure low temperature hydrogenation, and all metal catalysts take off diene successful, and nitrogen and sulphur content there are not change substantially, all very high to the hydrogenation activity activity of cyanobenzene.Consider catalyzer price and diolefin and cyanobenzene hydrogenation effect, choose reasonable price, active best metal NiMo catalyzer.
Embodiment 2
The metal NiMo catalyzer of take is investigated temperature of reaction and reaction pressure to removing the impact of diene and cyanobenzene hydrogenation effect as example, and the loading of Ni and Mo is respectively 20% and 10%.Following table 2 is shown in reaction process condition and product property.
As shown in Table 2, temperature of reaction is larger to diolefin hydrogenation and cyanobenzene hydrogenation influential effect, but work as temperature of reaction, is greater than 160 ℃, and it is not obvious that impact effect becomes.And reaction pressure is less to diolefin hydrogenation influential effect, and cyanobenzene hydrogenation is had to impact.Therefore, selective reaction condition is: 160 ℃ of temperature of reaction, reaction pressure 8MPa, volume space velocity 1h
-1, hydrogen to oil volume ratio 600.
Embodiment 3
Take NiMo catalyzer as example, on the basis of embodiment 2,8MPa and 160 ℃, carry out diolefin hydrogenation and the experiment of cyanobenzene stabilized hydrogenation, following table 3 is shown in the reaction process condition of operation in 500 hours and the product property finally obtaining.
The experimental result of 500 hours as shown in Table 3, on metal NiMo catalyzer in 160 ℃, 8MPa, volume space velocity 1h
-1, hydrogen to oil volume ratio 600, diolefin hydrogenation and cyanobenzene hydrogenation, known according to data before and after reaction, diene content and cyanobenzene hydrogenation rate are compared substantially constantly with starting test, show that catalyzer has high activity and stability.
Embodiment 4
On the basis of embodiment 2, removal phenol carbolic oil after low temperature hydrogenation is injected to water wash column, water wash column ambient operation, water and removal phenol carbolic oil volume ratio 0.5-2:1, at the bottom of water wash column tower, upper oil phase is pressed into hydrofining tower through adding, and at the bottom of water wash column tower, water enters rectifying tower, rectifying tower middle part charging, rectifying tower ejects water and removes water wash column, goes out high-purity benzene methylamine at the bottom of rectifying tower.Following table 4 is shown in reaction process condition and product property.
As shown in Table 4, the benzene methanamine concentration that removal phenol carbolic oil is produced after liquid-phase hydrogenatin, washing and rectifying is all greater than 98.5%, and when in water wash column, water removal phenol carbolic oil volume ratio is greater than 1, benzene methanamine percentage extraction is greater than 95%, but water removal phenol carbolic oil volume ratio is greater than 1, benzene methanamine percentage extraction increases not obvious.Therefore selection condition is: water/removal phenol carbolic oil volume ratio is 1, and water cooling tower temperature is 25 ℃.
Embodiment 5
On the basis of embodiment 2 and 4, investigate the stability experiment of technique, following table 5 is shown in the reaction process condition of operation in 500 hours and the product property finally obtaining.
As shown in Table 5: the present invention produces high-purity benzene methylamine through liquid-phase hydrogenatin, washing and distillation technology, and there is satisfactory stability.
Embodiment 6
Hydrobon catalyst adopts loading type NiMo sulfur catalyst.Carrier adopts SiO
2-Al
2o
3, specific surface area is at 200-400m
2/ g, pore volume is at 0.5-2.0cm
3/ g, most probable pore size distribution is at 2-4nm and 10-15nm.Nickel molybdenum sulphide precursor adopts nickelous nitrate or nickel acetate or acetylacetonate nickel and ammonium thiomolybdate.Adopt equi-volume impregnating to prepare loading type NiMo sulfide catalyst through dipping-dry-roasting-steps such as sulfuration.Following table 6 is shown in that reaction process condition and product form.
As shown in Table 6, oil distillate on load-type nickel molybdenum sulphide catalyzer in 360 ℃ of hydrofinings, diolefine in the product obtaining, do not detected, sulphur and nitrogen and gum level reduce greatly, show that load-type nickel molybdenum sulphide catalyzer has good desulfurization removing nitric deolefination efficiency.The product water-white obtaining, free from extraneous odour, the petrol and diesel oil mixture that quality is high.
Embodiment 7
Product introduction atmospheric distillation tower after hydrofining cuts into gasoline (<180 ℃) and diesel oil (>180 ℃) according to recovered temperature.Petrol and diesel oil character is shown in by lower 7 tables.
As shown in Table 7, oil distillate on supported cobalt molybdenum sulphide catalyzer in 360 ℃ of hydrofinings, diolefine in the product obtaining, do not detected, the content of sulphur and nitrogen reduces greatly, shows that load-type nickel molybdenum sulphide catalyzer has good desulfurization removing nitric deolefination efficiency.The product water-white obtaining, free from extraneous odour, the gasoline that quality is high and diesel oil.
Embodiment 8
Take catalytic distillation diesel oil distillate as raw material, on the basis of embodiment 6 and 7,8MPa and 360 ℃, carry out stability experiment, following table 8 is shown in the reaction process condition of operation in 1000 hours and the product property finally obtaining.
The experimental result of 1000 hours in 360 ℃ of hydrofinings, does not detect diolefine in the petrol and diesel oil product obtaining in air distillation on load-type nickel molybdenum sulphide catalyzer as shown in Table 8, for gasoline gum content, reaches 2mg100mL
-1, for diesel oil gum level, be also reduced to 12mg100mL
-1, sulphur and nitrogen containing comparing substantially constantly with starting test, meet national petrol and diesel oil standard, show the product free from extraneous odour that this technology obtains, have good stability, the petrol and diesel oil that quality is high.The above results shows that technology of the present invention has satisfactory stability.
Claims (5)
1. a method for removal phenol carbolic oil benzene methanamine processed and clean fuel, is characterized in that:
Removal phenol carbolic oil pressurization is mixed into hydrogenation tower with hydrogen, carries out low temperature hydrogenation and remove cyanobenzene and diolefin in removal phenol carbolic oil, feeding temperature 140-180 ℃, hydrogen partial pressure 4-8MPa, volume space velocity 0.5-1.0h
-1, hydrogen to oil volume ratio 400-600:1; Hydrogenation catalyst is metal supported catalyst; After hydrogenation, removal phenol carbolic oil enters water wash column, water wash column ambient operation, water and removal phenol carbolic oil volume ratio 0.5-2, under water wash column tower, the layer benzene methanamine aqueous solution enters rectifying tower, charging in tower, and rectifying tower ejects water, beat and be recycled into water wash column, at the bottom of rectifying tower, go out high-purity benzene methylamine; After hydrogenation, removal phenol carbolic oil is mixed into hydrofining tower with hydrogen after washing, carries out hydrogenation upgrading, feeding temperature 320-360 ℃, hydrogen partial pressure 6-8MPa, volume space velocity 0.4-1.0h
-1, hydrogen to oil volume ratio 600-1200:1; The catalyzer that hydrogenation is used is sulfide catalyst; Distillate after hydrofining, through air distillation, cuts into gasoline according to recovered temperature.
2. method according to claim 1, is further characterized in that: described metal supported catalyst is Pd, PtPd, Co, Ni, CoMo or NiMo; Carrier is SiO
2, Al
2o
3, TiO
2, SiO
2-Al
2o
3or Al
2o
3-TiO
2.
3. method according to claim 1 and 2, is further characterized in that: described sulfide catalyst is NiMo, NiW, CoMo, CoW, NiMoW or CoMoW; Carrier is SiO
2-Al
2o
3or Al
2o
3-TiO
2.
4. the method for a kind of removal phenol carbolic oil according to claim 1 and 2 benzene methanamine processed and clean fuel, is further characterized in that: liquid-phase hydrogenatin, washing, rectifying, hydrofining and distillation operate continuously.
5. the method for a kind of removal phenol carbolic oil according to claim 3 benzene methanamine processed and clean fuel, is further characterized in that: liquid-phase hydrogenatin, washing, rectifying, hydrofining and distillation operate continuously.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110756534A (en) * | 2019-10-16 | 2020-02-07 | 宝钢化工湛江有限公司 | Shutdown cleaning method for industrial naphthalene distillation device |
Citations (3)
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|---|---|---|---|---|
| EP0590673A1 (en) * | 1992-10-02 | 1994-04-06 | Mitsubishi Oil Company, Limited | Process for producing low viscosity lubricating base oil having high viscosity index |
| CN102465033A (en) * | 2010-11-04 | 2012-05-23 | 中国石油化工股份有限公司 | Processing method of medium-low temperature coal tar |
| CN102807900A (en) * | 2011-06-01 | 2012-12-05 | 中国科学院过程工程研究所 | High-value utilization method for oxygen-enriched coal tar |
-
2014
- 2014-05-19 CN CN201410212307.8A patent/CN103965962B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0590673A1 (en) * | 1992-10-02 | 1994-04-06 | Mitsubishi Oil Company, Limited | Process for producing low viscosity lubricating base oil having high viscosity index |
| CN102465033A (en) * | 2010-11-04 | 2012-05-23 | 中国石油化工股份有限公司 | Processing method of medium-low temperature coal tar |
| CN102807900A (en) * | 2011-06-01 | 2012-12-05 | 中国科学院过程工程研究所 | High-value utilization method for oxygen-enriched coal tar |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110756534A (en) * | 2019-10-16 | 2020-02-07 | 宝钢化工湛江有限公司 | Shutdown cleaning method for industrial naphthalene distillation device |
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