CN107754850A - A kind of method for preparing charcoal base acid material using the alkylation spent acid containing ionic liquid - Google Patents
A kind of method for preparing charcoal base acid material using the alkylation spent acid containing ionic liquid Download PDFInfo
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- CN107754850A CN107754850A CN201610683222.7A CN201610683222A CN107754850A CN 107754850 A CN107754850 A CN 107754850A CN 201610683222 A CN201610683222 A CN 201610683222A CN 107754850 A CN107754850 A CN 107754850A
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- ionic liquid
- charcoal base
- acid
- containing ionic
- acid material
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B17/00—Sulfur; Compounds thereof
- C01B17/69—Sulfur trioxide; Sulfuric acid
- C01B17/88—Concentration of sulfuric acid
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B17/00—Sulfur; Compounds thereof
- C01B17/69—Sulfur trioxide; Sulfuric acid
- C01B17/90—Separation; Purification
- C01B17/92—Recovery from acid tar or the like, e.g. alkylation acids
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C1/00—Ammonia; Compounds thereof
- C01C1/24—Sulfates of ammonium
- C01C1/242—Preparation from ammonia and sulfuric acid or sulfur trioxide
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- Organic Chemistry (AREA)
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Abstract
The present invention relates to a kind of method for preparing charcoal base acid material using the alkylation spent acid containing ionic liquid, it comprises the following steps：Alkylation spent acid containing ionic liquid auxiliary agent is heated to 100~500 DEG C, keeps 1~10h, product is washed to neutrality with solvent, 60~200 DEG C of drying, the charcoal base acid material is obtained, wherein, the solvent is at least one of water, dilute sulfuric acid, ammoniacal liquor, ammonium sulfate.Method process route that the present invention prepares charcoal base acid material is short, investment is small, simple to operate, operating cost is low, applied widely, it is possible to achieve the recycling of the molten oil of Waste Sulfuric Acid intermediate ion liquid, acid and sulfuric acid recycles, and reduces carbon emission.
Description
Technical field
The present invention relates to a kind of method for preparing charcoal base acid material using the alkylation spent acid containing ionic liquid, especially
It is that the spent acid of ionic liquid concerted catalysis iso-butane and olefine reaction generation alkylate oil prepares charcoal base acid material.
Technical background：
Sulfuric acid alkylation is using catalytic cracking, the butylene of catalytic reforming unit by-product, isobutene or amylene as raw material, is used
98% sulfuric acid is catalyst, the higher technical octane of the purity that the isoparaffin of carbon four and alkene are produced by alkylation techniques
Technique.The worsening of domestic atmospheric environment promotes the speed-raising that oil product upgrades, alkylate oil have octane number is high, steam forces down,
Without sulphur, without aromatic hydrocarbons the advantages that, be preferable to substitute MTBE and the environment-friendly high-knock rating gasoline addO-on therapy of ethanol.Increase
The harmonic proportion of isooctane is to speed up the upgrading of domestic gasoline, reduces in motor-vehicle tail-gas noxious gas emission and environmental protection most
Effective way.At the same time, the recoverable amount sustainable growth of national automobile, the rigid demand to high-quality oil product sharply increase.Cause
This, in following prevention and control of air pollution and oil quality escalation process, the importance of isooctane will become increasingly conspicuous, while also indicate
The bright market prospects that isooctane produces in China's oil refining industry.Sulphate method is in isooctane industrialized production at present
Occupy leading position, the newly-built isooctane device of recent domestic uses sulfate technology more, and 84% uses in domestic new device
Concentrated sulfuric acid technology.In alkylation process, when sulfuric acid concentration is less than 90%, it must be discharged from reactor, here it is institute
The waste sulfuric acid from alkylation said, alkylate oil per ton can produce 80-100kg Waste Sulfuric Acid.Domestic sulfuric acid process alkylation production capacity at present
More than 10,000,000 tons, more than 1,000,000 tons of Waste Sulfuric Acid such as will be had up to production.
Auxiliary agent can increase sulfuric acid and the contact surface of Liquefied Hydrocarbon, in reactor catalyst can be made more preferably to be connect with reactant
Touch, in good emulsified state, so as to improve reaction efficiency, improve the octane number of product, reduce catalyst consumption.2009
Year, American scholar BalaSubramaniam takes the lead in reporting the alkyl for carrying out iso-butane/butylene with regulation of ionic liquid liquid acid
Change reaction, shown preferable alkylation catalytic activity (Journal of Catalysis2009,268,243-250,
US20100331599Al), this is alkylated field for research C4 and has opened up a new direction.Domestic patent also discloses that use
Ionic liquid surfactant carries out the alkylated reaction of iso-butane as ionic liquid/super acids coupled catalyst of auxiliary agent
(CNI01885655A, CNI02134507A, CN101851526A, CN104232153), good catalysis is equally also shown
Effect, the service life cycle of ionic liquid/super acids fusion catalyst can significantly be improved by showing the addition of auxiliary agent.Contain
Acid fat, auxiliary agent and water account for 10-15% or so in the Waste Sulfuric Acid of auxiliary agent, and outward appearance is brown or dark brown and has strong thorn
Swash property smell.The price of auxiliary agent is general higher, and the conventional acid regeneration technique of industry at present is high temperature pyrolytic cracking (HTP), and molten oil of acid etc. is organic
Thing burn at high temperature production carbon dioxide be discharged into air, auxiliary agent also decomposes at high temperature.
With the increasingly strict and cost pressure of environmental requirement, Waste Sulfuric Acid is always a great problem for perplexing manufacturing enterprise,
The alkylation spent acid that recycling treatment contains ionic liquid auxiliary agent is imperative.If in strict accordance with national environmental protection policy and easily
System poisons product management rules to perform, and the enterprise that most domestic produces Waste Sulfuric Acid will close down.It is so-called chemically for angle
Waste refers to the material not being utilized, if these materials effectively utilized, not only can significantly cut down pollution, while
Resource can be saved.
Common solid sulfoacid catalyst has sulfamic acid, p-methyl benzenesulfonic acid, sulfonate resin, biomass carbon sulfonic acid etc., makees
For a kind of strong protonic acid catalyst, it is widely used in being esterified, is etherified, is dehydrated, being hydrated, in the acid catalyzed reaction such as isomery.To toluene
Sulfonic acid and sulfamic acid are soluble in water and be catalyzed as liquid acid when being catalyzed organic reaction, exist difficult separation, corrosivity it is strong,
The shortcomings of seriously polluted.Sulfonate resin heatproof is low, the silicon substrate solid sulfoacid obtained on silica-base material through silanization, oxidation, system
The standby time is grown, cumbersome.Carbonized using biomass through sulfuric acid, then the solid sulfoacid of sulfonated dose of sulfonation, preparation journey be present
The shortcomings of sequence is more, cost is high.
Sour molten oil in spent acid is the mixture with very wide boiling point, is the COMPLEX MIXED that height is unsaturated and ionizes
Thing, its ingredient amount is widely distributed, complicated, predominantly sulfuric ester and be mostly containing five C atoms rings and branch chain group
Into hydrocarbon compound, contain 2~4 double bonds in per molecule on average, two of which is conjugated double bond, and conjugated double bond is very
It may be respectively distributed on cyclic hydrocarbon and its side chain.Using the unsaturated double-bond and hydrogen bond of these molten hydrocarbon molecules of acid, sent out in sulfuric acid
The reactions such as raw esterification, sulfonation, polymerization, charing, it is acid to generate the charcoal base containing groups such as sulfuryl, sulfonic group, acidic ion liquids
Material.Waste Sulfuric Acid, which is regenerated, for this can both mitigate environmental pollution significantly, and recyclable a part of sulfuric acid resource and carbon resource,
With great economic benefit and environmental benefit.
The content of the invention
It is an object of the invention to provide a kind of charcoal base acid material is prepared using the alkylation spent acid containing ionic liquid
Method, it is intended to solve the problems, such as that iso-butane and olefin alkylation are combined to obtain Waste Sulfuric Acid recycling caused by alkylate oil.
The embodiment of the present invention is achieved in that offer is a kind of and prepares charcoal base using the alkylation spent acid containing ionic liquid
The method of acid material, it comprises the following steps：
Alkylation spent acid containing ionic liquid auxiliary agent is heated to 100~500 DEG C, keeps 1~10h, product solvent
Wash to neutrality, drying, obtain the charcoal base acid material, wherein, the solvent is in water, dilute sulfuric acid, ammoniacal liquor, ammonium sulfate
It is at least one.
The method that alkylation spent acid of the utilization containing ionic liquid of the present invention prepares charcoal base acid material, utilizes alkylation
Sour molten oil and ionic liquid in Waste Sulfuric Acid, polymerization is heated in sulfuric acid solution, obtains the charcoal base acidity material containing ionic liquid
Material, realizes the separation of Organic Materials of Spent acid and sulfuric acid.The present invention prepares charcoal base acid using the alkylation spent acid containing ionic liquid
The method of property material, process route is short, investment is small, simple to operate, operating cost is low, applied widely, it is possible to achieve Waste Sulfuric Acid
The recycling of middle organic matter, ionic liquid and sulfuric acid recycles, and reduces carbon emission, is ionic liquid concerted catalysis iso-butane
It is combined to obtain Waste Sulfuric Acid caused by alkylate oil with olefin alkylation and carries out recycling treatment.
Embodiment
In order to make the purpose , technical scheme and advantage of the present invention be clearer, with reference to embodiments, to the present invention
It is described in further detail.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, it is not used to limit
The fixed present invention.
The embodiment of the present invention is achieved in that offer is a kind of and prepares charcoal base using the alkylation spent acid containing ionic liquid
The method of acid material, it comprises the following steps：
Alkylation spent acid containing ionic liquid auxiliary agent is heated to 100~500 DEG C, keeps 1~10h, product solvent
Wash to neutrality, drying, obtain the charcoal base acid material, wherein, the solvent is at least one in water, ammoniacal liquor, ammonium sulfate
Kind.
Specifically, the organic impurities hair such as the ionic liquid in the alkylation spent acid containing ionic liquid auxiliary agent, the molten oil of acid
Raw polymerisation, obtains the black charcoal base acid material containing sulfuric acid.It can add to criticize in the heating polymerization process and obtain
Product charcoal base acid material or activated carbon accelerate polymerization speed, the sulfurous gas discharged in the heating process passes through dilute sulphur
Discharged after the washing of bronsted lowry acids and bases bronsted lowry liquid.
The product washing need to be carried out at room temperature, and the washing can be repeated several times, and cleaning solution can repeat to make
With.Further, the pickle after the water washing can further be concentrated to give the concentrated sulfuric acid, and the water of concentrating and separating can be further
Washing for charcoal base acid material；The obtained concentrated sulfuric acid can adjust to obtain concentration using oleum or sulfur trioxide
90~98% concentrated sulfuric acid is used to produce.
Further, the product after ammonia scrubbing liquid is ammonium sulfate, is obtained after condensing crystallizing separation, ammonium sulfate and sulphur
Washing or obtained ammonium sulfate of the water that sour ammonium mother liquor, ammonium sulfate liquor and concentrating and separating go out still available for charcoal base acid material are straight
Connect and be used for chemical fertilizer fertilizer.
The method provided in an embodiment of the present invention for preparing charcoal base acid material using the alkylation spent acid containing ionic liquid,
Using the sour molten oil and ionic liquid in waste sulfuric acid from alkylation, it is anti-that polymerization, esterification, charing, sulfonation etc. are heated in sulfuric acid solution
Carbon based material should be generated.Because the molten oil content of acid is high in Waste Sulfuric Acid, the molten oil of ionic liquid, acid and sulfuric acid have very strong combination
Power, the molten oil composition of the acid such as ionic liquid, sulfuric acid ester can be polymerized to charcoal in sulfuric acid solution in the molten oily course of reaction of acid
Base acid material, realize the recycling of organic matter and sulfuric acid.Charcoal base acid material sulfur content is handled without sulfonation
More than 5%, and containing 0.1~5% ionic liquid, there is stronger acidity, available for acidic catalyst.Tune can also be passed through
Section polymerization technique obtains polymerizeing Carbon Materials, substitutes petroleum coke and is used for electrode and fuel.Meanwhile in the dilute sulfuric acid obtained in the process
Content of organics is very low, and COD is less than 2000mg/L, requires no decolouring and deodorization processing, is directly concentrated to give colourless dense sulphur
Acid is directly neutralized to obtain ammonium sulfate with ammonia.
Embodiment
Embodiment one
A certain amount of spent acid (250mL) in round-bottomed flask is weighed, 140 DEG C is increased to from room temperature, then maintains 5h, is cooled down
To room temperature, the water for weighing twice of spent acid is added in round-bottomed flask, is stirred overnight, is filtered, obtaining filtrate, (dilute sulfuric acid is molten at room temperature
Liquid) and filter cake (charcoal base acid material), filtrate is collected into beaker, and ammoniacal liquor (25- is slowly added under conditions of stirring
28wt%), until then solution evaporates solution, there is crystal precipitation in neutrality.Filter cake is washed with deionized until neutral, baking
It is dry, elementary analysis detection sulfur content, icp detection Oil repellents.The COD value of filtrates tested, as a result as shown in table 1：
Table 1
Embodiment two
A certain amount of spent acid (250mL) in round-bottomed flask is weighed, 200 DEG C is increased to from room temperature, then maintains 3h, is cooled down
To room temperature, the water for weighing twice of spent acid is added in round-bottomed flask, is stirred overnight, is filtered, obtaining filtrate, (dilute sulfuric acid is molten at room temperature
Liquid) and filter cake (charcoal base acid material), filtrate is collected into beaker, and ammoniacal liquor (25- is slowly added under conditions of stirring
28wt%), until then solution evaporates solution, there is crystal precipitation in neutrality.Filter cake is washed with deionized until neutral, baking
It is dry, elementary analysis detection sulfur content, icp detection Oil repellents.The COD value of filtrates tested, as a result as shown in table 2：
Table 2
Embodiment three
Weigh inventory nAcetic acid：nEthanol=1:1.2(nAcetic acid=0.5mol, nEthanol=0.6mol), add three mouthfuls with condenser pipe
Flask, add charcoal base acid material mCharcoal base acid material=1g, T=60 DEG C of reaction temperature, reaction time t=2h, reaction negate after terminating
Liquid is answered to do gas-chromatography, acetic acid conversion 98.5%, the charcoal base acid material has good catalytic activity.
Applicant state, the above embodiments are merely illustrative of the technical solutions of the present invention and it is unrestricted, although with reference to preferable
The present invention is described in detail embodiment, it will be understood to those skilled in the art that can be to the technical side of the present invention
Case is modified or equivalent substitution, and without departing from the spirit and scope of technical solution of the present invention, it all should cover in the present invention
Right in.
The preferred embodiment of the present invention described in detail above, still, the present invention are not limited in above-mentioned embodiment
Detail, in the range of the technology design of the present invention, a variety of simple variants can be carried out to technical scheme, this
A little simple variants belong to protection scope of the present invention.
It is further to note that each particular technique feature described in above-mentioned embodiment, in not lance
In the case of shield, can be combined by any suitable means, in order to avoid unnecessary repetition, the present invention to it is various can
The combination of energy no longer separately illustrates.
In addition, various embodiments of the present invention can be combined randomly, as long as it is without prejudice to originally
The thought of invention, it should equally be considered as content disclosed in this invention.
Claims (8)
1. a kind of method for preparing charcoal base acid material using the alkylation spent acid containing ionic liquid, it comprises the following steps：
Alkylation spent acid containing ionic liquid auxiliary agent is heated to 100~500 DEG C, keeps 1~10h, product is washed with solvent
To neutrality, 60~200 DEG C of drying, the charcoal base acid material is obtained, wherein, the solvent is water, dilute sulfuric acid, ammoniacal liquor, sulfuric acid
At least one of ammonium.
2. the method for preparing charcoal base acid material using the alkylation spent acid containing ionic liquid as claimed in claim 1, its
It is characterised by, the sulfurous gas discharged in the heating process after dilute sulfuric acid and alkali liquid washing by discharging.
3. the method for preparing charcoal base acid material using the alkylation spent acid containing ionic liquid as claimed in claim 1, its
It is characterised by, the product washing is carried out at room temperature, and the washing can be repeated several times, and cleaning solution can repeat to make
With.
4. the method for preparing charcoal base acid material using the alkylation spent acid containing ionic liquid as claimed in claim 1, its
Be characterised by, the drying temperature of the product is 60~200 DEG C, and drying pressure is -0.1~0.1MPa, drying time for 0.5~
5 hours.
5. the method for preparing charcoal base acid material using the alkylation spent acid containing ionic liquid as claimed in claim 1, its
It is characterised by, pickle is further concentrated to give the concentrated sulfuric acid after the water washing, and the water of concentrating and separating can be further used for charcoal
The washing of base acid material.
6. the method for preparing charcoal base acid material using the alkylation spent acid containing ionic liquid as claimed in claim 1, its
It is characterised by, the product after ammoniacal liquor or ammonium sulfate cleaning solution is ammonium sulfate, and ammonium sulfate is obtained after condensing crystallizing separation.
7. the method for preparing charcoal base acid material using the alkylation spent acid containing ionic liquid as claimed in claim 1, its
It is characterised by, the charcoal base acid material contains 1~20% sulphur and 0.1~5% acidic ion liquid.
8. the method that alkylation spent acid of the utilization as described in claim 1~8 containing ionic liquid prepares charcoal base acid material
The charcoal base acid material of acquisition can be used for be esterified, etherification reaction catalyst.
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| CN201610683222.7A CN107754850B (en) | 2016-08-17 | 2016-08-17 | Method for preparing carbon-based acidic material by using alkylated waste acid containing ionic liquid |
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| CN201610683222.7A CN107754850B (en) | 2016-08-17 | 2016-08-17 | Method for preparing carbon-based acidic material by using alkylated waste acid containing ionic liquid |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108751162A (en) * | 2018-07-05 | 2018-11-06 | 北京中富瑞科环保科技有限公司 | A kind of carbonizing treatment method of antibiotic bacterium dregs |
| CN108910858A (en) * | 2018-07-05 | 2018-11-30 | 北京中富瑞科环保科技有限公司 | A kind of recycling processing method of organic medical waste |
| CN110092358A (en) * | 2019-05-24 | 2019-08-06 | 华东理工大学 | A kind of processing method of waste sulfuric acid from alkylation |
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| US4014982A (en) * | 1975-06-30 | 1977-03-29 | Texaco Development Corporation | Combined process for upgrading spent alkylation acid and reducing noxious gas content of waste gaseous streams |
| CN87100790A (en) * | 1987-02-18 | 1988-08-31 | 李寿彬 | A kind of treatment process of waste sulfuric acid from alkylation |
| CN104229746A (en) * | 2014-09-18 | 2014-12-24 | 中石化南京工程有限公司 | New method for preparing sulfur from alkylated waste acid |
-
2016
- 2016-08-17 CN CN201610683222.7A patent/CN107754850B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4014982A (en) * | 1975-06-30 | 1977-03-29 | Texaco Development Corporation | Combined process for upgrading spent alkylation acid and reducing noxious gas content of waste gaseous streams |
| CN87100790A (en) * | 1987-02-18 | 1988-08-31 | 李寿彬 | A kind of treatment process of waste sulfuric acid from alkylation |
| CN104229746A (en) * | 2014-09-18 | 2014-12-24 | 中石化南京工程有限公司 | New method for preparing sulfur from alkylated waste acid |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108751162A (en) * | 2018-07-05 | 2018-11-06 | 北京中富瑞科环保科技有限公司 | A kind of carbonizing treatment method of antibiotic bacterium dregs |
| CN108910858A (en) * | 2018-07-05 | 2018-11-30 | 北京中富瑞科环保科技有限公司 | A kind of recycling processing method of organic medical waste |
| CN108751162B (en) * | 2018-07-05 | 2023-03-21 | 北京中富瑞科环保科技有限公司 | Carbonization treatment method of antibiotic fungi residues |
| CN108910858B (en) * | 2018-07-05 | 2023-04-07 | 北京中富瑞科环保科技有限公司 | Resourceful treatment method for organic medical waste |
| CN110092358A (en) * | 2019-05-24 | 2019-08-06 | 华东理工大学 | A kind of processing method of waste sulfuric acid from alkylation |
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