CN106566577B - The method of sulfide in molecular sieve catalytic oxidation removal oil product - Google Patents
The method of sulfide in molecular sieve catalytic oxidation removal oil product Download PDFInfo
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- CN106566577B CN106566577B CN201510655569.6A CN201510655569A CN106566577B CN 106566577 B CN106566577 B CN 106566577B CN 201510655569 A CN201510655569 A CN 201510655569A CN 106566577 B CN106566577 B CN 106566577B
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Abstract
The present invention relates to a kind of method of sulfide in molecular sieve catalytic oxidation removal oil product, the prior art is mainly solved there are adsorbent Sulfur capacity saturated capacity is low, removes halfway problem.The present invention is by using including the steps that oil product, hydrogen peroxide is made to be contacted with molecular sieve；The molecular sieve is M Ti HMS, wherein M is to be selected from IB, IIB, IVB, VB, VI B, VII B or the element of VIII race in addition to Ti；In the molecular sieve, the technical solution that the molar ratio of Si and M are 1~100 preferably resolves the problem, can be used in molecular sieve catalytic oxidation removal oil product in the industrial production of sulfide.
Description
Technical field
The present invention relates to a kind of methods of sulfide in molecular sieve catalytic oxidation removal oil product.
Background technology
HMS mesoporous materials are the mesoporous silicon materials of a kind of hexagonal phase structure, due to long-range order and short distance is unordered
Institutional framework, since synthesis in the industries such as petrochemical industry as the research and development of catalyst by enough attention.In recent years, with generation
Various countries of boundary propose the sulfur-bearing standard that is increasingly stringenter, how effective desulfurization, producing ultra-clean fuel oil becomes research hotspot both domestic and external
With problem in the urgent need to address.Wherein, Titanium Sieve Molecular Sieve receives increasingly as a kind of efficient, environmentally protective catalyst
More concerns.
With research work gradually deeply, it has been found that HMS materials relative to M41S series materials have thicker hole wall,
Higher hydrothermal stability and the framework modification advantage for being more suitable for material.Therefore, the research of HMS materials becomes again in recent years
The important directions of mesoporous silicon material.Especially using HMS materials as carrier, by metal or nonmetalloid, inorganic salts, You Ji great
Molecule or bioactive substance etc. modify its skeleton, duct, surface or modified etc. more become new function material
Research hotspot.Currently, the synthesis of the heteroatom mesopore molecular sieves such as Ti, Zr, V, Cr, Mn, Cu and Fe, characterization and catalytic performance are ground
Study carefully common report.But in terms of the investigation for being catalyzed behavior to heteroatom mesopore molecular sieve is confined to catalysis oxidation more, and it is most of
Research concentrate on using HMS as carrier.Ti-HMS as a kind of excellent carrier, the research that it is modified at present also compared with
It is few.Zepeda etc. and Halachev etc. using Ti-HMS as carrier, prepare respectively CoMo and NiW bimetallic catalysts for plus hydrogen take off
Reaction of Salmon-Saxl obtains preferable desulfurization effect.Beneficial approach is provided for the removing of follow-up study macromolecular sulfide.
Currently used sulfur method has hydrodesulfurization, catalytic desulfurization, rectifying desulfurization and absorption desulfurization.Hydrodesulfurization due to
Hydrogen source is needed, and the phenyl ring of aromatic hydrocarbons can be hydrogenated in hydrodesulfurization, therefore the loss of of high cost and aroamtic hydrocarbon raw material is serious, no
It is suitble to aromatizing and desulfurizing.Rectifying desulphurization plant cost of investment is high, and since certain sulfide and aromatic hydrocarbons form total waste, desulfurization precision
Technological requirement is not achieved.Desulfurization is adsorbed there are the Sulfur capacity saturated capacity of adsorbent is low, removes halfway problem.
CN101525549A discloses a kind of hydrocracking tail oil deep adsorbent desulfurizing and denitrifying method, it includes that will contain a certain amount of vulcanization
The hydrocracking tail oil and a kind of hydrocracking tail oil deep absorption desulfurization, denitrifier of object and nitride are in certain temperature, pressure
With contacted under air speed, obtain the desulfurization removing nitric hydrocracking tail oil after adsorption refining, product sulphur nitrogen content meets plus hydrogen is different
The requirement of structure dewaxed feedstock.But this method has that complex process, equipment investment and operating cost are high, non-renewable.
Invention content
The technical problem to be solved by the present invention is to the prior arts there are the Sulfur capacity saturated capacity of adsorbent is low, and removing is not thorough
The problem of bottom, the method that sulfide in a kind of molecular sieve catalytic oxidation removal oil product is provided.This method has absorption property strong, inhales
The big feature of attached capacity.
In order to solve the above technical problems, the technical solution adopted by the present invention is as follows：A kind of molecular sieve catalytic oxidation removal oil
The method of sulfide in product includes the steps that oil product, hydrogen peroxide is made to be contacted with molecular sieve；The molecular sieve is M-Ti-HMS,
Wherein, M is to be selected from IB, IIB, IVB, VB, VI B, VII B or the element of VIII race in addition to Ti；In the molecular sieve, Si and M's
Molar ratio is 1~100.
In above-mentioned technical proposal, it is preferable that the molar ratio of Si and M is 10~70.It is highly preferred that the molar ratio of Si and M is
10~60.
In above-mentioned technical proposal, it is preferable that a concentration of 0.01~20000 mg/kg of sulfide in oil product.More preferably
A concentration of 0.1~8000 mg/kg of sulfide in ground oil product.
In above-mentioned technical proposal, it is preferable that M be selected from Cu, Ag, Au, Zn, Ti, Zr, V, Nb, Cr, Mo, W, Mn, Re, Fe,
At least one of Co, Ni, Ru, Rh, Pd or Pt.It is highly preferred that M is selected from least one of Cu, Ag, Zn or Ni.
In above-mentioned technical proposal, it is preferable that the sulfide is thiophene, 2- methylthiophenes, 3 methyl thiophene, 2,5- diformazans
Base thiophene, 2,4- thioxenes, 2,3- thioxenes, 3,4- thioxenes, tetramethyl thiophene, methyl mercaptan, ethyl mercaptan,
At least one of propanethiol, isobutyl mercaptan, diethyl thioether, carbonyl sulfur or carbon disulfide.
In above-mentioned technical proposal, it is preferable that oil product is 0.1~10 hour with molecular sieve time of contact, oil product and molecular sieve
Contact Temperature is 10~100 DEG C, and the molar ratio of hydrogen peroxide and sulphur in oil product is 3~6, and the dosage of molecular sieve is oil product weight
1~3%.
In above-mentioned technical proposal, it is preferable that in the molecular sieve M-Ti-HMS, Si/Ti molar ratios are 10~60.
Molecular sieve M-Ti-HMS described in the method for the present invention is with the metal-modified Ti-HMS molecular sieves containing M.Modification side
Method is infusion process known in the art, in-situ synthesis or NH3The precipitation method.
By the present invention in that the oil product of sulfur-bearing, such as hydrocracking tail oil occur under the action of M-Ti-HMS molecular sieves
Catalytic oxidation, effectively removes sulfide, and the removal efficiency of sulfide can reach 90% or more.Simultaneously as removal efficiency is high,
So that the operation cycle of adsorbent extends, corresponding production cost reduces, and achieves preferable technique effect.
With reference to embodiment, the invention will be further elaborated.
Specific implementation mode
【Embodiment 1】
Using Ti-HMS as carrier (Si/Ti molar ratios is 20), with Cu (NO3)2For the sources Cu, rubbed according to Si/Cu using infusion process
You are than for 10 dipping 5 hours, then 70 DEG C of drying 5 hours, and 550 DEG C of roastings 4 hours obtain Cu/Ti-HMS-10 samples, 10 are
Si/Cu molar ratios.
Thiophene, 2,5- thioxenes and ethyl mercaptan are dissolved in normal octane, thiophene content 150mg/kg, 2,5- diformazans
Base thiophene content is 50mg/kg, and ethyl mercaptan content is 50mg/kg, and mould oil is made.
It weighs【Embodiment 1】In 0.1 gram of Cu/Ti-HMS-10 sample in conical flask, be added 10ml mould oils, second
Nitrile makees solvent, waits for that the temperature of heat collecting type constant temperature blender with magnetic force is stabilized to 70 DEG C, 0.5gH is added into flask rapidly2O2(quality
Score is that 30%), flask is put into water-bath, after reaction is finished and is cooled to room temperature, with electronic centrifuge, takes upper layer clear
Sulfur content after liquid measurement desulfurization in oil phase.The removal efficiency of sulfide is 92.62%.
【Comparative example 1】
Using HMS as carrier (Si/Ti molar ratios is 20), with Cu (NO3)2For the sources Cu, using infusion process according to Si/Cu moles
Than for 10 dipping 5 hours, then 70 DEG C of dryings 5 hours, 550 DEG C roast 4 hours, obtain Cu-HMS samples.
0.1 gram of Cu-HMS sample is weighed in conical flask, 10ml is added【Embodiment 1】In mould oil, acetonitrile is made molten
0.5gH is added rapidly after the temperature of heat collecting type constant temperature blender with magnetic force is stabilized to 70 DEG C in agent into flask2O2(mass fraction
For 30%), flask is put into water-bath, reaction finishes be cooled to room temperature after, with electronic centrifuge, supernatant liquor is taken to survey
Determine the sulfur content in oil phase after desulfurization.The removal efficiency of sulfide is 86.87%.
【Embodiment 2】
Using Ti-HMS as carrier (Si/Ti molar ratios is 25), with Cu (NO3)2For the sources Cu, rubbed according to Si/Cu using infusion process
You were than 20 dipping 5 hours, then 70 DEG C of drying 5 hours, and 550 DEG C of roastings 4 hours obtain Cu/Ti-HMS-20 samples.
0.2 gram of Cu/Ti-HMS-20 sample is weighed in conical flask, 10ml is added【Embodiment 1】In mould oil, second
Nitrile makees solvent, and after the temperature of heat collecting type constant temperature blender with magnetic force is stabilized to 70 DEG C, 0.5gH is added into flask rapidly2O2(matter
It is that 30%), flask is put into water-bath to measure score, after reaction is finished and is cooled to room temperature, with electronic centrifuge, takes upper layer
Sulfur content after clear liquid measurement desulfurization in oil phase.The removal efficiency of sulfide is 91.58%.
【Embodiment 3】
Using Ti-HMS as carrier (Si/Ti molar ratios is 40), with Cu (NO3)2For the sources Cu, rubbed according to Si/Cu using infusion process
You were than 30 dipping 5 hours, then 70 DEG C of drying 5 hours, and 550 DEG C of roastings 4 hours obtain Cu/Ti-HMS-40 samples.
0.2 gram of Cu/Ti-HMS-40 sample is weighed in conical flask, 10ml is added【Embodiment 1】In mould oil, second
Nitrile makees solvent, and after the temperature of heat collecting type constant temperature blender with magnetic force is stabilized to 70 DEG C, 0.4gH is added into flask rapidly2O2(matter
It is that 30%), flask is put into water-bath to measure score, after reaction is finished and is cooled to room temperature, with electronic centrifuge, takes upper layer
Sulfur content after clear liquid measurement desulfurization in oil phase.The removal efficiency of sulfide is 88.42%.
【Embodiment 4】
Using Ti-HMS as carrier (Si/Ti molar ratios is 60), with Cu (NO3)2For the sources Cu, rubbed according to Si/Cu using infusion process
You were than 10 dipping 5 hours, then 70 DEG C of drying 5 hours, and 550 DEG C of roastings 4 hours obtain Cu/Ti-HMS-60 samples.
0.1 gram of Cu/Ti-HMS-60 sample is weighed in conical flask, 10ml is added【Embodiment 1】In mould oil, second
Nitrile makees solvent, and after the temperature of heat collecting type constant temperature blender with magnetic force is stabilized to 70 DEG C, 0.3gH is added into flask rapidly2O2(matter
It is that 30%), flask is put into water-bath to measure score, after reaction is finished and is cooled to room temperature, with electronic centrifuge, takes upper layer
Sulfur content after clear liquid measurement desulfurization in oil phase.The removal efficiency of sulfide is 86.87%.
【Embodiment 5】
Using Ti-HMS as carrier (Si/Ti molar ratios is 10), with AgNO3For the sources Ag, using infusion process according to Si/Ag moles
Than 15 dipping 5 hours, then 70 DEG C of drying 5 hours, 550 DEG C of roastings 4 hours obtained Ag/Ti-HMS-15 samples.
0.1 gram of Ag/Ti-HMS-15 sample is weighed in conical flask, 10ml is added【Embodiment 1】In mould oil, second
Nitrile makees solvent, and after the temperature of heat collecting type constant temperature blender with magnetic force is stabilized to 70 DEG C, 0.4gH is added into flask rapidly2O2(matter
It is that 30%), flask is put into water-bath to measure score, after reaction is finished and is cooled to room temperature, with electronic centrifuge, takes upper layer
Sulfur content after clear liquid measurement desulfurization in oil phase.The removal efficiency of sulfide is 90.21%.
【Comparative example 2】
Using HMS as carrier (Si/Ti molar ratios is 10), with AgNO3For the sources Ag, using infusion process according to Si/Ag molar ratios
15 dippings 5 hours, then 70 DEG C of drying 5 hours, 550 DEG C of roastings 4 hours obtain Ag-HMS samples.
0.1 gram of Ag-HMS sample is weighed in conical flask, 10ml is added【Embodiment 1】In mould oil, acetonitrile is made molten
0.4gH is added rapidly after the temperature of heat collecting type constant temperature blender with magnetic force is stabilized to 70 DEG C in agent into flask2O2(mass fraction
For 30%), flask is put into water-bath, reaction finishes be cooled to room temperature after, with electronic centrifuge, supernatant liquor is taken to survey
Determine the sulfur content in oil phase after desulfurization.The removal efficiency of sulfide is 85.64%.
【Embodiment 6】
Using Ti-HMS as carrier (Si/Ti molar ratios is 30), with Zn (NO3)2For the sources Zn, rubbed according to Si/Zn using infusion process
You were than 25 dipping 5 hours, then 70 DEG C of drying 5 hours, and 550 DEG C of roastings 4 hours obtain Zn/Ti-HMS-25 samples.
0.2 gram of Zn/Ti-HMS-25 sample is weighed in conical flask, 10ml is added【Embodiment 1】In mould oil, second
Nitrile makees solvent, and after the temperature of heat collecting type constant temperature blender with magnetic force is stabilized to 70 DEG C, 0.5gH is added into flask rapidly2O2(matter
It is that 30%), flask is put into water-bath to measure score, after reaction is finished and is cooled to room temperature, with electronic centrifuge, takes upper layer
Sulfur content after clear liquid measurement desulfurization in oil phase.The removal efficiency of sulfide is 89.46%.
【Comparative example 3】
Using HMS as carrier (Si/Ti molar ratios is 30), with Zn (NO3)2For the sources Zn, using infusion process according to Si/Zn moles
Than 25 dipping 5 hours, then 70 DEG C of drying 5 hours, 550 DEG C of roastings 4 hours obtained Zn-HMS samples.
0.2 gram of Zn-HMS sample is weighed in conical flask, 10ml is added【Embodiment 1】In mould oil, acetonitrile is made molten
0.5gH is added rapidly after the temperature of heat collecting type constant temperature blender with magnetic force is stabilized to 70 DEG C in agent into flask2O2(mass fraction
For 30%), flask is put into water-bath, reaction finishes be cooled to room temperature after, with electronic centrifuge, supernatant liquor is taken to survey
Determine the sulfur content in oil phase after desulfurization.The removal efficiency of sulfide is 78.53%.
【Embodiment 7】
Using Ti-HMS as carrier (Si/Ti molar ratios is 10), with Ni (NO3)2For the sources Ni, rubbed according to Si/Ni using infusion process
You were than 30 dipping 5 hours, then 70 DEG C of drying 5 hours, and 550 DEG C of roastings 4 hours obtain Ni/Ti-HMS-30 samples.
0.1 gram of Ni/Ti-HMS-30 sample is weighed in conical flask, 10ml is added【Embodiment 1】In mould oil, second
Nitrile makees solvent, and after the temperature of heat collecting type constant temperature blender with magnetic force is stabilized to 70 DEG C, 0.4gH is added into flask rapidly2O2(matter
It is that 30%), flask is put into water-bath to measure score, after reaction is finished and is cooled to room temperature, with electronic centrifuge, takes upper layer
Sulfur content after clear liquid measurement desulfurization in oil phase.The removal efficiency of sulfide is 89.57%.
【Comparative example 4】
Using HMS as carrier (Si/Ti molar ratios is 10), with Ni (NO3) 2 for the sources Ni, using infusion process according to Si/Ni moles
Than 30 dipping 5 hours, then 70 DEG C of drying 5 hours, 550 DEG C of roastings 4 hours obtained Ni-HMS samples.
0.08 gram of Ni-HMS sample is weighed in conical flask, 10ml is added【Embodiment 1】In mould oil, acetonitrile is made molten
0.3gH is added rapidly after the temperature of heat collecting type constant temperature blender with magnetic force is stabilized to 70 DEG C in agent into flask2O2(mass fraction
For 30%), flask is put into water-bath, reaction finishes be cooled to room temperature after, with electronic centrifuge, supernatant liquor is taken to survey
Determine the sulfur content in oil phase after desulfurization.The removal efficiency of sulfide is 77.45%.
Claims (10)
1. a kind of method of sulfide in molecular sieve catalytic oxidation removal oil product, including oil product, hydrogen peroxide and molecular sieve is made to connect
Tactile step；The molecular sieve is M-Ti-HMS, wherein M is in addition to Ti selected from IB, IIB, IVB, VB, VI B, VII B or VIII
The element of race；In the molecular sieve, the molar ratio of Si and M are 1~100.
2. according to claim 1 in molecular sieve catalytic oxidation removal oil product sulfide method, it is characterised in that Si's and M
Molar ratio is 10~70.
3. according to claim 2 in molecular sieve catalytic oxidation removal oil product sulfide method, it is characterised in that Si's and M
Molar ratio is 10~60.
4. according to claim 1 in molecular sieve catalytic oxidation removal oil product sulfide method, it is characterised in that in oil product
A concentration of 0.01~20000 mg/kg of sulfide.
5. according to claim 4 in molecular sieve catalytic oxidation removal oil product sulfide method, it is characterised in that in oil product
A concentration of 0.1~8000 mg/kg of sulfide.
6. according to claim 1 in molecular sieve catalytic oxidation removal oil product sulfide method, it is characterised in that M is selected from
At least one of Cu, Ag, Au, Zn, Ti, Zr, V, Nb, Cr, Mo, W, Mn, Re, Fe, Co, Ni, Ru, Rh, Pd or Pt.
7. according to claim 6 in molecular sieve catalytic oxidation removal oil product sulfide method, it is characterised in that M is selected from
At least one of Cu, Ag, Zn or Ni.
8. according to claim 1 in molecular sieve catalytic oxidation removal oil product sulfide method, it is characterised in that the sulphur
Compound is thiophene, 2- methylthiophenes, 3 methyl thiophene, 2,5- thioxenes, 2,4- thioxenes, 2,3- dimethyl thiophenes
Pheno, 3,4- thioxenes, tetramethyl thiophene, methyl mercaptan, ethyl mercaptan, propanethiol, isobutyl mercaptan, diethyl thioether, carbonyl sulfur
Or at least one of carbon disulfide.
9. according to claim 1 in molecular sieve catalytic oxidation removal oil product sulfide method, it is characterised in that described point
In son sieve M-Ti-HMS, Si/Ti molar ratios are 10~60.
10. according to claim 1 in molecular sieve catalytic oxidation removal oil product sulfide method, it is characterised in that oil product with
Molecular sieve Contact Temperature is 10~100 DEG C, and time of contact is 0.1~10 hour, and the molar ratio of hydrogen peroxide and sulphur in oil product is 3
~6, molecular sieve dosage is the 1~3% of oil product weight.
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| CN1912060A (en) * | 2006-07-07 | 2007-02-14 | 中国石油化工股份有限公司 | Highly sulfur removal method of diesel oil |
| CN101255352A (en) * | 2008-04-21 | 2008-09-03 | 大连理工大学 | Method for removing sulfides in gasoline by oxidation-absorption under mild conditions |
| CN102757811A (en) * | 2011-04-26 | 2012-10-31 | 中国石油化工股份有限公司 | Diesel oil oxidative desulphurization method |
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| CN1912060A (en) * | 2006-07-07 | 2007-02-14 | 中国石油化工股份有限公司 | Highly sulfur removal method of diesel oil |
| CN101255352A (en) * | 2008-04-21 | 2008-09-03 | 大连理工大学 | Method for removing sulfides in gasoline by oxidation-absorption under mild conditions |
| CN102757811A (en) * | 2011-04-26 | 2012-10-31 | 中国石油化工股份有限公司 | Diesel oil oxidative desulphurization method |
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