CN104789261A - Method adopting dephenollized phenol oil for preparing indane and clean fuel - Google Patents
Method adopting dephenollized phenol oil for preparing indane and clean fuel Download PDFInfo
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- CN104789261A CN104789261A CN201510170730.0A CN201510170730A CN104789261A CN 104789261 A CN104789261 A CN 104789261A CN 201510170730 A CN201510170730 A CN 201510170730A CN 104789261 A CN104789261 A CN 104789261A
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Abstract
The invention discloses a method adopting dephenollized phenol oil for preparing indane and clean fuel, and belongs to the technical field of environmental protection and energy. The method is characterized in that dephenollized phenol oil is adopted as the raw material, and the method is the technique used for preparing high-purity indane and clean fuel through the steps of liquid-phase hydrogenization, flash vaporization, rectification, cryogenic separation, centrifugal separation, rectification over again, hydrofining and redistillation. Petrol and diesel mixed oil which is free of bad odors and high in quality is obtained by desulphurization, denitrification and colloid elimination; distillation is carried out to obtain petrol and diesel distillate oil. According to the method, a hydrogenation catalyst and a hydrofining catalyst used in the method are adopted to prepare indane and clean fuel by selecting appropriate carriers according to the composition and performance of dephenollized phenol oil through the impregnation method. The method is simple in technique, 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 a kind of method of removal phenol carbolic oil indane and clean fuel.
Background technology
In Coal Chemical Industry process, coal tar is as one of the staple product of coking industry, and its output accounts for 3% ~ 4% of shove charge coal.Coal tar is mainly used to processing light oil, carbolic oil, naphtalene oil and modified pitch etc., then after deep processing, produce the multiple Chemicals such as benzene, phenol, naphthalene, anthracene, needle coke.Coal tar obtains following product through distillation cutting: light oil (<170 DEG C); Carbolic oil (170 ~ 210 DEG C); Naphtalene oil (210 ~ 230 DEG C); Carbolineum (300 ~ 360 DEG C).Removal phenol carbolic oil refers to the oil of carbolic oil after phenolic compound is sloughed in alkali cleaning.The production equipment that producer utilizes coal tar to produce phenolic compound in recent years constantly increases, and causes the output of removal phenol carbolic oil to grow with each passing day.Removal phenol carbolic oil contains a large amount of aromatic hydroxy compounds, and random abandoning can cause the wasting of resources and environmental pollution.Rationally utilize removal phenol carbolic oil for resource recycling fully, environment protection is significant.
Indane has another name called 2,3-indane, colourless solution, boiling point is 176.5 DEG C, can be used as shockproof dose of aviation fuel, shockproof dose of rubber industry etc., and its derivative can be made 20 more and plant medicine, can also, as the raw material of organic synthesis and solvent, be a kind of fine chemicals of high added value simultaneously.
Removal phenol carbolic oil contains 23.4% indane, the indenes of 15.7%, the coumarone of 4.1% and other aromatic compounds.After simple hydrogenation, indane content can reach 40%.And in industry at present and research, all producing of indane is not related to the process of removal phenol carbolic oil.Utilize the indenes in removal phenol carbolic oil and coumarone to prepare coumarone-indene resin to the process of removal phenol carbolic oil in current factory.This treatment process only uses indenes and coumarone component in removal phenol carbolic oil, causes indane and the waste of other components.
Producing clean fuel oil with removal phenol carbolic oil is the important directions all utilizing removal phenol carbolic oil.By hydrofining, slough the sulphur atom in raw material, nitrogen-atoms, colloid etc. and produce to obtain clean fuel.But containing indenes and diolefin in removal phenol carbolic oil, they are easily polymerized under Hydrofinishing conditions, the polymkeric substance of formation easily forms carbon distribution at catalyst surface, thus causes catalyst deactivation.And hydrofining also result in the waste of the indane of high-content in removal phenol carbolic oil.
According to chemical constitution and the character of removal phenol carbolic oil, Problems existing in utilizing for above-mentioned removal phenol carbolic oil, we successfully develop the new technology that indane and clean fuel oil are produced in removal phenol carbolic oil hydrogenation-flash distillation-rectifying-low temperature separation process-centrifugation-rectifying-hydrofining-distillation.Removal phenol carbolic oil contains the indane of 23.4% and the indenes of 15.7%, by low temperature hydrogenation, indenes is converted into indane, thus the content that improve indane also eliminates the hidden danger of hydrofinishing state indenes at catalyst surface polymerization carbon distribution.Highly purified indane is reclaimed by flash distillation-rectifying-low temperature separation process-centrifugation-rectifying separation after hydrogenation.Removal phenol carbolic oil remaining ingredient is through the obtained clean petrol and diesel oil component of hydrofining-distillation.Producing without the three wastes in hydrogenation-flash distillation-rectifying-low temperature separation process-centrifugation-rectifying-hydrofining-distillation, is a green recycling process.Following known technology, all comes with some shortcomings:
Chinese patent, publication number: CN103589466A, describing a kind of removal phenol carbolic oil by coal chemical technology is applied in oil fuel, make use of the characteristic that the allotment of removal phenol carbolic oil is high, 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.
Wu Guojun mentions and utilizes indenes in removal phenol carbolic oil, coumarone component to synthesize coumarone indene resin in " taking removal phenol carbolic oil as waste high-quality coumarone-indene resin " literary composition.But the treatment process of remaining ingredient do not mentioned in article, cause the wasting of resources of remaining ingredient.
Bai Qingzi etc. mention in " research of Technology of Recovering Naphthalene from Dephenollized Phenol Oil " and utilize the characteristic of the easy crystallization of naphthalene to prepare NAPTHALENE FLAKES. (INDUSTRIAL GRADE） from removal phenol carbolic oil.The treatment process of other components do not mentioned in same article.
Summary of the invention
The invention provides a kind of method of removal phenol carbolic oil indane and clean fuel.Low and utilize the problems such as insufficient for removal phenol carbolic oil conversion process added value, with high purity indane and high-quality petrol and diesel oil for target product, realize removal phenol carbolic oil recycling, make production process energy saving standard, avoid the wasting of resources.Specifically, the present invention by removal phenol carbolic oil low temperature hydrogenation, flash distillation, rectifying, low temperature separation process, centrifugation and again rectifying prepare high purity indane, diolefin in removal phenol carbolic oil is removed in the liquid-phase hydrogenatin of removal phenol carbolic oil high pressure low temperature, hydrotreated lube base oil indenes generates indane, and the catalyzer that hydrogenation uses is metal supported catalyst or metal sulfide catalyst; After hydrogenation, removal phenol carbolic oil enters flashing tower, and the gaseous fraction after flash distillation obtains high purity indane through rectifying-low temperature separation process-centrifugation-rectifying; Liquid ingredient after flash distillation and rectifying tower A overhead components are mixed into hydrofining tower, the catalyzer that hydrofining uses is sulfide catalyst, monoene compound is removed by monoolefin hydrogenation saturated reaction, and desulfurization, denitrogenation, except colloid produce free from extraneous odour, high-quality petrol and diesel oil mixing oil, then through distillation obtain gasoline and diesel oil blending oil.Invention increases removal phenol carbolic oil utilization ratio, increase its added value, energy-conservation of consumption reduction, the extending catalyst life-span.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 diolefin in removal phenol carbolic oil, and indenes hydrogenation generates indane reaction, feeding temperature 100-160 DEG C, hydrogen partial pressure 4-8MPa, volume space velocity 0.5-1.0h
-1, hydrogen to oil volume ratio 200-400:1; Hydrogenation catalyst is metal supported catalyst or metal sulfide catalyst; After hydrogenation, removal phenol carbolic oil enters flashing tower, carries out simple separation to removal phenol carbolic oil.Flashing tower tower top cuts out the cut before 178 DEG C, wherein comprises most of indane.After flash distillation, gaseous fraction enters rectifying tower A and carries out the degree of depth to indane and other components and be separated, and obtain the cut of 175 ~ 178 DEG C in rectifying tower A tower reactor, its main component is indane and connects triphen.Main component is that the material of indane enters in low temperature separation process cold hydrazine, and cold hydrazine temperature is-40 DEG C, be used for separating indan with connect triphen, connect triphen crystallization.Centrifugation connects triphen crystal and obtains the indane centrifugate that purity is 93.6%, and impeller pump is set to two one and opens one standby to realize operate continuously.The indane product that purity is greater than 96% can be obtained after rectifying tower B is separated through centrifugal indane.Flashing tower liquid ingredient and rectifying tower A overhead components are mixed into hydrofining tower, feeding temperature 320-360 DEG C, 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 uses is sulfide catalyst; Distillate after hydrofining, through air distillation, cuts into gasoline (<180 DEG C) and diesel oil (>180 DEG C) according to recovered temperature.Technique scheme can continuous operation.
Hydrogenation catalyst in the present invention is metal supported catalyst or metal sulfide catalyst, and metal supported catalyst is Pd, Co, Ni, CoMo or NiMo; Metal sulfide catalyst is NiMo or NiMoW sulfide catalyst; 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, and low temperature liquid phase hydrogenation removes diolefin in removal phenol carbolic oil, prevents it to be polymerized in hydrofining tower, increases the Hydrobon catalyst life-span.Hydrofining tower use Hydrobon catalyst for supported sulfide catalyzer 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
3, TiO
2, SiO
2-Al
2o
3or Al
2o
3-TiO
2.
Produce through hydrogenation, flash distillation, rectifying, low temperature separation process, centrifugation the indane purity >96% obtained by removal phenol carbolic oil of the present invention; Removal phenol carbolic oil through low temperature liquid phase hydrogenation, hydrofining, distill the yield of gasoline fraction (<180 DEG C) at 85-90%, octane value is 85-92, density 0.70-0.75g/cm
3, can as the blend component of gasoline.The yield of diesel oil distillate (>180 DEG C) is at 10-15%, and cetane value is 45, density 0.82-0.84g/cm
3, can as diesel oil.
The mode of low temperature liquid phase hydrogenation of the present invention, flash distillation, rectifying, low temperature separation process, centrifugation, hydrogenation upgrading, air distillation employing operate continuously, flexible operation.Adopt hydrogenation, flash distillation, rectifying, high purity indane is prepared in low temperature separation process and under low hydrogen/gasoline ratio and high-speed, low temperature hydrogenation removes diolefin in removal phenol carbolic oil, prevents it to be polymerized in hydrofining tower, increases the Hydrobon catalyst life-span.The present invention can obtain high purity high added value indane and high-quality clean fuel oil, thus realizes the recycling of removal phenol carbolic oil.
Accompanying drawing explanation
Fig. 1 is process flow diagram of the present invention.
In figure: 1 hydrogenation tower; 2 flashing towers; 3 rectifying tower A; 4 low temperature separation process cold hydrazines; 5 impeller pumps; 6 rectifying tower B; 7 hydrofining towers; 8 distillation towers.
Embodiment
The specific embodiment of the present invention is described in detail below in conjunction with technical scheme and accompanying drawing.
Embodiment 1
Hydrogenation catalyst is loading type Pd, Co, Ni, CoMo, NiMo metal catalyst or NiMo or NiMoW sulfide catalyst.Carrier adopts SiO
2-Al
2o
3, specific surface area is at 300-500m
2/ g, pore volume is at 2-3cm
3/ g, most probable pore size is distributed in 2-4nm and 10-15nm.Metal precursor adopts palladium or Palladous nitrate, Cobaltous diacetate or Jing Ti/Bao Pian COBALT NITRATE CRYSTALS/FLAKES respectively, acetic acid pinches or nickelous nitrate, Jing Ti/Bao Pian COBALT NITRATE CRYSTALS/FLAKES and ammonium molybdate, nickelous nitrate and ammonium molybdate.Equi-volume impregnating is adopted to prepare load type metal catalyst through steps such as dipping-drying-roast-reduction.For metal Pd metal loading at 3-10%; For metal Co and Ni metal loading at 20-40%; Be supported on 15-25% for CoMo and NiMo metal Co and Ni, metal M o is supported on 5-15%.For NiMo and NiMoW sulfide catalyst, adopt equi-volume impregnating through step preparations such as dipping-drying-roast-reduction-sulfurations.Metal precursor is nickelous nitrate, ammonium molybdate and ammonium tungstate, and the loading of Ni, Mo and W is respectively 20%, 5% and 5%.Following table 1 is shown in reaction process condition and product property.
As shown in Table 1, removal phenol carbolic oil takes off diene through high pressure low temperature hydrogenation, and all metal catalysts take off diene successful, indenes through hydrocracking be indane.Owing to high temperature polymerization can generate carbon distribution because of component in hydrofining section afterwards, cause catalyst deactivation, therefore choose indenes active better, the highest NiMo metal of corresponding indane content is as catalyzer.
Embodiment 2
Temperature of reaction and reaction pressure is investigated on the impact of indane content for NiMo metal catalyst.The loading of Ni, Mo is respectively 20%, and 10%.Following table 2 is shown in reaction process condition and product property.
By table 2, consider the impact of reaction conditions on diolefin, indane content, selective reaction condition is: temperature of reaction 160 DEG C, reaction pressure 8MPa, volume space velocity 1h
-1, hydrogen to oil volume ratio 400.
Embodiment 3
For NiMo metal catalyst, catalyst stability experiment is carried out at 8MPa and 160 DEG C in the basis of embodiment 2, following table 3 is shown in the reaction process condition run for 500 hours and the product property finally obtained.
The experimental result of 500 hours as shown in Table 3, NiMo metal catalyst in 160 DEG C, 8MPa, volume space velocity 1h
-1, hydrogen to oil volume ratio 400, diolefin hydrogenation, indenes hydrocracking is indane, according to reaction before and after data, diene content start test with indane content compared with substantially constant, show that catalyzer has high activity and stability.
Embodiment 4
Removal phenol carbolic oil after hydrogenation enters flashing tower and carries out simple division.Tower top is the <178 DEG C of component containing indane, and the percentage composition of its composition sees the following form 4
Embodiment 5
Flashing tower gas enters rectifying tower A and splits further material, and tower reactor cuts the cut of 175 ~ 178 DEG C.Its composition percentage ratio sees the following form 5
Embodiment 6
The cut of rectifying tower A tower reactor enters cryogenic separation device through heat exchange.Triphen crystallization is connected and indane is still liquid in the deep cooling stage.After sufficient crystallising, material enters whizzer and carries out solid-liquid separation.It is the vapor-compression refrigerant cycle that refrigeration agent is formed that deep cooling adopts with propylene, and its cryogenic temperature is-40 DEG C.Through centrifugal, connect triphen crystal and be separated with indane, the composition percentage ratio of centrifugate is as shown in table 6 below.
Embodiment 7
After low temperature separation process, the purity of indane can reach 93.6%, is separated high-purity indane that can obtain purity and be greater than 96% through rectifying tower B further.Feed liquid after centrifugal enters rectifying tower B after heat exchange.Tower reactor cuts out the component of 176 ~ 178 DEG C.Its content percentage ratio is as shown in table 7 below after testing.
Embodiment 8
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 is distributed in 2-4nm and 10-15nm.Nickel molybdenum sulphide precursor adopts nickelous nitrate or nickel acetate or acetylacetonate nickel and ammonium thiomolybdate.Equi-volume impregnating is adopted to prepare loading type NiMo sulfide catalyst through steps such as dipping-drying-roast-reduction-sulfurations.Following table 8 is shown in reaction process condition and product composition.
As shown in Table 8, distillate on load-type nickel molybdenum sulfide catalyst in 360 DEG C of hydrofinings, diolefine do not detected in the product obtained, the content of sulphur and nitrogen reduces greatly, shows that load-type nickel molybdenum sulfide catalyst has good desulfurization removing nitric deolefination efficiency.The product water-white obtained, free from extraneous odour, the petrol and diesel oil mixture that quality is high.
Embodiment 9
Product introduction atmospheric distillation tower after hydrofining cuts into gasoline (<180 DEG C) and diesel oil (>180 DEG C) according to recovered temperature.Following table 9 is shown in petrol and diesel oil character.
As shown in Table 9, distillate on supported cobalt molybdenum sulfide catalyst in 360 DEG C of hydrofinings, diolefine do not detected in the product obtained, the content of sulphur and nitrogen reduces greatly, shows that load-type nickel molybdenum sulfide catalyst has good desulfurization removing nitric deolefination efficiency.The product water-white obtained, free from extraneous odour, the gasoline that quality is high and diesel oil.
Embodiment 10
With catalytic distillation diesel oil distillate for raw material, stability experiment is carried out at 8MPa and 360 DEG C in the basis of embodiment 8 and 9, following table 10 is shown in the reaction process condition run for 1000 hours and the product property finally obtained.
The experimental result of 1000 hours as shown in Table 10, in 360 DEG C of hydrofinings on load-type nickel molybdenum sulfide catalyst, does not detect diolefine, reaches 2mg100mL for gasoline gum content in the petrol and diesel oil product that air distillation obtains
-1, also 12mg100mL is reduced to for diesel oil gum level
-1, sulphur and nitrogen containing with start compared with test substantially constant, meet national petrol and diesel oil standard, show to have good stability the product free from extraneous odour that this technology obtains, 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. the method for a removal phenol carbolic oil indane and clean fuel, it is characterized in that, removal phenol carbolic oil and hydrogen are mixed into hydrogenation tower, and low temperature hydrogenation removes diolefin in removal phenol carbolic oil, indenes hydrogenation generates indane reaction, feeding temperature 100-160 DEG C, hydrogen partial pressure 4-8MPa, volume space velocity 0.5-1.0h
-1, hydrogen to oil volume ratio 200-400:1; Hydrogenation catalyst is metal supported catalyst or metal sulfide catalyst; After hydrogenation, removal phenol carbolic oil enters flashing tower, flashing tower tower top cuts out the cut before 178 DEG C, after flash distillation, gaseous fraction enters rectifying tower A and carries out the degree of depth to indane and other components and be separated, and obtain the cut of 175-178 DEG C in rectifying tower A tower reactor, its composition is indane and connects triphen; Indane enters in low temperature separation process cold hydrazine, and temperature is-40 DEG C, and further separating indan and even triphen, connect triphen crystallization; Centrifugation connects triphen crystal and obtains the indane centrifugate that purity is 93.6%, and impeller pump is set to two one and opens one for realizing operate continuously; After rectifying tower B is separated, the indane that purity is greater than 96% is obtained through centrifugal indane; Flashing tower liquid ingredient and rectifying tower A overhead components are mixed into hydrofining tower, feeding temperature 320-360 DEG C, hydrogen partial pressure 6-8MPa, volume space velocity 0.4-1.0h
-1, hydrogen to oil volume ratio 600-1200:1; Hydrobon catalyst is sulfide catalyst; Distillate after hydrofining, through air distillation, cuts into gasoline and diesel oil according to recovered temperature.
2. method according to claim 1, is characterized in that, described metal supported catalyst is Pd, Co, Ni, CoMo or NiMo; Described metal sulfide catalyst is NiMo or NiMoW sulfide catalyst; 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 characterized in that, described sulfide catalyst is NiMo, NiW, CoMo, CoW, NiMoW or CoMoW, and carrier is SiO
2, Al
2o
3, TiO
2, SiO
2-Al
2o
3or Al
2o
3-TiO
2.
4. method according to claim 1 and 2, is characterized in that, low temperature hydrogenation, flash distillation, rectifying, low temperature separation process, centrifugation, hydrofining and distillation are operate continuously.
5. method according to claim 3, is characterized in that, low temperature hydrogenation, flash distillation, rectifying, low temperature separation process, centrifugation, hydrofining and distillation are operate continuously.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114436752A (en) * | 2020-10-16 | 2022-05-06 | 中国石油化工股份有限公司 | Method for improving comprehensive utilization rate of ethylene cracking C9 fraction |
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| US20090277823A1 (en) * | 2005-11-30 | 2009-11-12 | Bsh Bosch Und Siemens Haugerate Gmbh | Refrigeration Device Comprising a Water Filter |
| CN102336622A (en) * | 2010-07-29 | 2012-02-01 | 邢台旭阳煤化工有限公司 | Reclaiming device and separation method for heavy component residue of coked crude benzene hydrogenation process |
-
2015
- 2015-04-10 CN CN201510170730.0A patent/CN104789261B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090277823A1 (en) * | 2005-11-30 | 2009-11-12 | Bsh Bosch Und Siemens Haugerate Gmbh | Refrigeration Device Comprising a Water Filter |
| CN102336622A (en) * | 2010-07-29 | 2012-02-01 | 邢台旭阳煤化工有限公司 | Reclaiming device and separation method for heavy component residue of coked crude benzene hydrogenation process |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114436752A (en) * | 2020-10-16 | 2022-05-06 | 中国石油化工股份有限公司 | Method for improving comprehensive utilization rate of ethylene cracking C9 fraction |
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