CN102989196A - Separation method for phenol compounds in oil - Google Patents
Separation method for phenol compounds in oil Download PDFInfo
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- CN102989196A CN102989196A CN201110274037XA CN201110274037A CN102989196A CN 102989196 A CN102989196 A CN 102989196A CN 201110274037X A CN201110274037X A CN 201110274037XA CN 201110274037 A CN201110274037 A CN 201110274037A CN 102989196 A CN102989196 A CN 102989196A
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Abstract
The present invention provides a separation method for phenol compounds in oil. The method comprises: adopting a quaternary ammonium salt as a separation agent to separate phenol compounds in oil, and adopting an ether to re-crystallize the quaternary ammonium salt from a eutectic substance. With the method, use of a large amount of acid solutions and alkali solutions, and generation of a large amount of phenol-containing wastewater are avoided, the separation device body is reduced, the separation agent can be reused, recovery rate is high, cost is reduced, and the conventional oil phenol separation steps are substantially simplified.
Description
Technical field
The present invention relates to Coal Chemical Industry, petrochemical industry separation field, be specifically related to the separation method of a kind of phenol, aromatic hydrocarbon mixture.
Background technology
Phenolic compound is one of Elementary Chemical Industry raw material, is widely used in the fields such as fiber, plastics, agricultural chemicals, medicine, anticorrisive agent, explosive be synthetic.They are mainly derived from DCL/Direct coal liquefaction product, coal tar and oil product.In recent years, caused domestic and international researcher's extensive concern from the research of DCL/Direct coal liquefaction product, coal tar and oil product extraction phenolic compound.
Conventional method is to adopt sodium hydroxide solution to carry out wash-out, the wash-out ratio juris is to utilize phenolic compound to have faintly acid, after highly basic is reacted, forms sodium phenolate solution soluble in water, phenolic compound is transferred to from oil phase to water, reaches the purpose of separation.Its process is: with sodium hydrate aqueous solution, with the carbolic oil mixture, contact, phenol reacts with NaOH and generates sodium phenolate, and sodium phenolate is water-soluble, and oil does not dissolve in water, realizes that the sodium phenolate aqueous solution separates with the oil of dephenolize.The regenerative process of sodium phenolate is: clean phenol sodium and certain density sulfuric acid solution are sent into to reactor simultaneously, and product enters a separator after cooling.The crude phenols that reaction obtains are discharged from separator top, and metabisulfite solution is discharged in bottom.
Although the sodium hydroxide solution elution method is selectively higher, need to consume a large amount of acid-base solutions, high to equipment requirement, and also while when cut in, having alkali and phenol, such as the pyridine alkali, pyridine alkali and phenol generation complex compound, unfavorable to alkali cleaning simultaneously.After the more important thing is that pickling finishes, produce a large amount of phenol wastewater, cause the last handling process complexity, contaminated environment is seriously polluted.
For the problems referred to above, the present invention has developed the method for phenolic compound in a kind of anhydrous separating oil, and release agent easily separates with phenolic compound, thereby has avoided the generation of a large amount of phenol wastewater, has prevented environmental pollution.This method can reuse release agent, reduces separation costs, has important science and realistic meaning.
Summary of the invention
The invention provides and a kind ofly take quaternary ammonium salt and carry out the method for phenolic compound in separating oil as release agent.The method has been avoided the use of a large amount of acid, aqueous alkali; Reduced the separator volume; Release agent can be reused, and has reduced cost.
The present invention be take quaternary ammonium salt as release agent, thereby form eutectic at 0 ~ 150 ℃ with phenols in oil, realizes separating of oily phenol, and phenolic compound separates simple, and quaternary ammonium salt can reuse, thereby avoids environmental pollution, has reduced production cost.
The objective of the invention is to realize by the following technical solutions:
The separation method of phenolic compound in a kind of oil, the method comprises with aromatic hydrocarbon, and chlorinated aromatic hydrocarbons is simulated oil, and the quaternary ammonium salt of take carrys out the step of phenolic compound in separating oil as release agent.
In said method, described aromatic hydrocarbon and chlorinated aromatic hydrocarbons are one or more in benzene, toluene, paraxylene, meta-xylene, ortho-xylene, chlorobenzene, dichloro-benzenes.
In said method, described quaternary ammonium salt general formula is R
1r
2r
3r
4n
+x
?, R wherein
1, R
2, R
3, R
4can be identical or different, represent C
1~ C
6alkyl, haloalkyl or hydroxyl substituted alkyl, wherein X means the halogens such as fluorine, chlorine, bromine or iodine.
In said method, described phenolic compound is phenol, cresols, ethyl-phenol, xylenol, naphthols or dihydroxy or polyhydroxy phenol as one or more in resorcinol.
In said method, separation temperature is 0 ~ 150 ℃; Disengaging time is 0.1 ~ 60min.
Said method also comprise quaternary ammonium salt with oily phenol mixture, contact form 2 be separated and finish after, the eutectic vacuum removal a small amount of oil wherein by lower phase quaternary ammonium salt with phenols formation.The vacuum removal temperature is 50 ~ 250
oc, be 0.2 ~ 24h drying time, and then be recrystallized.
Said method also comprises employing ethers recrystallization quaternary ammonium salt, and the quaternary ammonium salt of recovery is reused to step as release agent.The ethers adopted comprises one or more of ether, benzinum, methyl phenyl ethers anisole, n-butyl ether, phenetole.10 ~ 50 ℃ of recrystallization temperatures, recrystallization time 1 ~ 60min.
Said method comprises the steps:
(1) phenolic compound is dissolved in to aromatic hydrocarbon or chlorinated aromatic hydrocarbons prepares simulated oil;
(2) take quaternary ammonium salt as release agent, with phenolic compound in oil, form eutectic, phenolic compound leaves oil phase;
(3) after separating end, the eutectic of the resulting lower floor of vacuum drying removes a small amount of oil carried wherein mutually, and then uses ethers recrystallization quaternary ammonium salt.
Below will describe the present invention.
The invention provides and take quaternary ammonium salt as release agent, phenols in quaternary ammonium salt and oil forms eutectic and isolates oil phase, and phenolic compound is phenol, cresols, ethyl phenol, dimethyl phenol, naphthols or dihydroxy or polyhydroxy phenol as one or more in resorcinol; The separation process the present invention relates to, in oil, phenolic compound concentration is 10 ~ 300g/L, quaternary ammonium salt and phenolic compound mol ratio are 0.3 ~ 2.0; Separation temperature is 0 ~ 150 ℃, and disengaging time is 0.1 ~ 60min; Separate and finish the final vacuum drying, baking temperature is 50 ~ 250
oc, be 0.2 ~ 24h drying time.Use ethers recrystallization quaternary ammonium salt, ethers comprises one or more of ether, benzinum, methyl phenyl ethers anisole, n-butyl ether, phenetole; While using ethers recrystallization quaternary ammonium salt, recrystallization temperature is 10 ~ 50 ℃, and the time is 1 ~ 60min.
Quaternary ammonium salt can with separate the principle that forms eutectic in oil and be: the phenolic compound in oil has the functional groups such as hydroxyl, these functional groups can form intermolecular hydrogen bonding with the halogen ion of quaternary ammonium salt, thereby reduced quaternary ammonium salt and the phenolic compound interior active force of molecule separately, thereby formed eutectic.This eutectic has the advantages that to be similar to ionic liquid, is insoluble to oil phase, thereby has realized the separation of oily phenol.
Compared with prior art, the present invention at least possesses following beneficial effect:
The present invention provides for phenolic compound in oil separates that a kind of technique is simple, separation costs is low, the disjunctive path of phenolic compound in environment amenable oil.
With traditional sodium hydroxide solution elution method, compare, it is release agent that the present invention adopts quaternary ammonium salt, has avoided the use of a large amount of acid-base solutions, has reduced cost.
The present invention can also adopt ether compound recrystallization quaternary ammonium salt, and quaternary ammonium salt can reuse, and prevents the generation of a large amount of phenol wastewater, has avoided environmental pollution.
The specific embodiment
Take quaternary ammonium salt as release agent below in conjunction with embodiment to provided by the invention, and in separating oil, the process of phenolic compound is described in further detail, but not thereby limiting the invention.
embodiment 1
The present embodiment explanation new method is compared with commercial run has very large advantage.
Industrial sodium hydroxide eluant solution method adopts the sodium hydroxide solution washing that mass fraction is 10% ~ 15%, and the sodium hydroxide solution that 40ml concentration is 15% joins 20ml simulated oil (97.67g/L is dissolved with the toluene solution of phenol), stirs 20min.Lower floor's water adds the sulfuric acid solution 10ml acidifying that mass fraction is 60% after steaming and blowing down oily 30min, phenol recovery rate 95%, and NaOH, sulfuric acid solution is not recyclable, and produces phenol wastewater 38ml.
The process conditions of the present embodiment explanation are: phenol is dissolved in toluene and prepares simulated oil solution, and concentration is 97.67g/L, and quaternary ammonium salt is Choline Chloride (HOEt (Me)
3nCl), in Choline Chloride and toluene solution, the phenol mol ratio is 1, and separation temperature is 25 ℃, mixing time 15min.
Under 25 ℃, the 2.893g Choline Chloride joins in the 20ml oil solution, and standing 5min after stirring 15min, measure upper oil phase volume and phenol content, and the phenol clearance is 90.2%.Shift out upper oil phase, lower floor's congruent melting is vacuum drying 1h at 80 ℃ of temperature, removes the oil component that lower floor carries mutually.After cooling, add the 20ml ether, standing 5min after stirring 15min, reclaim Choline Chloride after centrifugal drying.Above process repeats 3 circulations, and the phenol clearance is that 90% ~ 91%, 3 circulation afterchlorinate choline rate of recovery are greater than 97%.
Because the boiling point difference of ether and phenol is larger, the phenol be dissolved in ether adopts the simple distillation method to separate.
With commercial run, compare, above method has been avoided the use of acid-base solution, has avoided the generation of a large amount of phenol wastewater, and quaternary ammonium salt can be used by Efficient Cycle.
embodiment 2
The process conditions of the present embodiment explanation are: phenol is dissolved in toluene and prepares simulated oil solution, and concentration is 97.67g/L, and quaternary ammonium salt is Choline Chloride, and in Choline Chloride and toluene solution, the phenol mol ratio is 0.8, and separation temperature is 50 ℃, mixing time 15min.
Under 50 ℃, the 2.893g Choline Chloride joins in the 20ml oil solution, and standing 5min after stirring 15min, measure upper oil phase volume and phenol content, and the phenol clearance is 89.0%.
Shift out upper oil phase, after the 80 ℃ of dry 1h of congruent melting phase vacuum of lower floor are cooling, add the 20ml ether, standing 5min after stirring 15min, reclaim Choline Chloride after centrifugal drying.
?
embodiment 3
The process conditions of the present embodiment explanation are: phenol is dissolved in toluene and prepares simulated oil solution, and concentration is 97.67g/L, and quaternary ammonium salt is Choline Chloride, and in Choline Chloride and toluene solution, the phenol mol ratio is 1, and separation temperature is 0 ℃, mixing time 15min.
Under 0 ℃, the 2.893g Choline Chloride joins in the 20ml oil solution, and standing 5min after stirring 15min, measure upper oil phase volume and phenol content, and the phenol clearance is 86.0%.
Shift out upper oil phase, after the 80 ℃ of dry 1h of congruent melting phase vacuum of lower floor are cooling, add the 20ml ether, standing 5min after stirring 15min, reclaim Choline Chloride after centrifugal drying.
?
embodiment 4
The process conditions of the present embodiment explanation are: phenol is dissolved in toluene and prepares simulated oil solution, and concentration is 47.20g/L, and quaternary ammonium salt is Choline Chloride, and in Choline Chloride and toluene solution, the phenol mol ratio is 1, and separation temperature is 0 ℃, mixing time 15min.
Under 0 ℃, the 1.397g Choline Chloride joins in the 20ml oil solution, and standing 5min after stirring 15min, measure upper oil phase volume and phenol content, and the phenol clearance is 84.0%.
Shift out upper oil phase, after the 80 ℃ of dry 1h of congruent melting phase vacuum of lower floor are cooling, add the 20ml ether, standing 5min after stirring 15min, reclaim Choline Chloride after centrifugal drying.
?
embodiment 5
The process conditions of the present embodiment explanation are: phenol is dissolved in toluene and prepares simulated oil solution, and concentration is 47.20g/L, and quaternary ammonium salt is cycocel (ClEtMe
3nCl), in cycocel and toluene solution, the phenol mol ratio is 1, and separation temperature is 0 ℃, mixing time 15min.
Under 0 ℃, the 3.563g cycocel joins in the 20ml oil solution, and standing 5min after stirring 15min, measure upper oil phase volume and phenol content, and the phenol clearance is 79.0%.
Shift out upper oil phase, after the 80 ℃ of dry 1h of congruent melting phase vacuum of lower floor are cooling, add the 20ml benzinum, standing 5min after stirring 15min, reclaim cycocel after centrifugal drying.
?
embodiment 6
The process conditions of the present embodiment explanation are: orthoresol is dissolved in paraxylene and prepares simulated oil solution, concentration is 201.5g/L, and quaternary ammonium salt is Choline Chloride, and in Choline Chloride and paraxylene solution, o-cresol mole ratios is 1, separation temperature is 25 ℃, mixing time 15min.
Under 25 ℃, the 6.117g Choline Chloride joins in the 20ml oil solution, and standing 5min after stirring 15min, measure upper oil phase volume and phenol content, and the orthoresol clearance is 92.4%.
The same embodiment of quaternary ammonium salt method of reducing.
?
embodiment 7
The process conditions of the present embodiment explanation are: metacresol is dissolved in paraxylene and prepares simulated oil solution, concentration is 200.2g/L, and quaternary ammonium salt is Choline Chloride, and in Choline Chloride and paraxylene solution, the metacresol mol ratio is 1, separation temperature is 25 ℃, mixing time 15min.
Under 25 ℃, the 6.170g Choline Chloride joins in the 20ml oil solution, and standing 5min after stirring 15min, measure upper oil phase volume and phenol content, and the metacresol clearance is 94.7%.
The same embodiment of quaternary ammonium salt method of reducing.
embodiment 8
The process conditions of the present embodiment explanation are: paracresol is dissolved in paraxylene and prepares simulated oil solution, concentration is 200.3g/L, and quaternary ammonium salt is Choline Chloride, and in Choline Chloride and paraxylene solution, the paracresol mol ratio is 1, separation temperature is 25 ℃, mixing time 15min.
Under 25 ℃, the 6.169g Choline Chloride joins in the 20ml oil solution, and standing 5min after stirring 15min, measure upper oil phase volume and phenol content, and the paracresol clearance is 94.7%.
The same embodiment of quaternary ammonium salt method of reducing.
Claims (9)
1. the separation method of phenolic compound in an oil, the method comprises take quaternary ammonium salt as release agent, thus quaternary ammonium salt and phenolic compound form the step that eutectic is isolated oil phase.
2. method according to claim 1, is characterized in that, described oil is that aromatic hydrocarbon and chlorinated aromatic hydrocarbons are one or more in benzene, toluene, paraxylene, meta-xylene, ortho-xylene, chlorobenzene, dichloro-benzenes.
3. according to the method described in claim 1, it is characterized in that, described phenolic compound is phenol, cresols, ethyl phenol, dimethyl phenol, naphthols or dihydroxy or polyhydroxy phenol as one or more in resorcinol.
4. according to the method described in claim 1, it is characterized in that, described method comprises the steps:
(1) take quaternary ammonium salt as release agent, contacted the phenolic compound in extraction oil with the oil that contains phenol;
(2) after separate finishing, the mixture of lower phase quaternary ammonium salt and phenol is carried out to vacuum drying, remove the oil wherein carried;
(3) add ether compound in the mixture to quaternary ammonium salt and phenol, the quaternary ammonium salt recrystallization is separated out with solid form, realizes the regeneration of quaternary ammonium salt;
(4) quaternary ammonium salt of regeneration is cycled to used in the separation of phenolic compound in oil.
5. according to the method described in claim 1 and 4, it is characterized in that, described quaternary ammonium salt general formula is R
1r
2r
3r
4n
+x
?, R wherein
1, R
2, R
3, R
4can be identical or different, represent C
1~ C
6alkyl, haloalkyl or hydroxyl substituted alkyl, wherein X means fluorine, chlorine, bromine or iodine, quaternary ammonium salt more is optimized for Choline Chloride.
6. according to the method described in claim 1 and 4, it is characterized in that, in oil, phenolic compound concentration is 10 ~ 300g/L, and quaternary ammonium salt and phenolic compound mol ratio are 0.3 ~ 2.0, and separation temperature is 0 ~ 150 ℃, and disengaging time is 0.1 ~ 60min; More preferably quaternary ammonium salt and phenolic compound mol ratio are 0.8 ~ 1.5, are separated into temperature 10 ~ 80
oc, disengaging time 5 ~ 30 min.
7. according to the described method of any one in claim 1 and 4, it is characterized in that, after having separated, the eutectic vacuum drying that quaternary ammonium salt and phenols form, the vacuum drying temperature is 50 ~ 250
oc, be 0.2 ~ 24 h drying time; More preferably temperature 70 ~ 150
oc, drying time 0.5 ~ 2 h.
8. according to the method described in claim 4, it is characterized in that, the ethers of employing comprises one or more of ether, benzinum, methyl phenyl ethers anisole, n-butyl ether, phenetole; More preferably ether and benzinum.
9. according to the method described in claim 4, it is characterized in that, in quaternary ammonium salt recrystallization regenerative process, temperature is 10-50 ℃, crystallization time 1 ~ 60min.
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| CN104946303A (en) * | 2015-05-18 | 2015-09-30 | 太原师范学院 | Method for selectively separating phenol mixture from oil |
| CN106039763A (en) * | 2016-07-08 | 2016-10-26 | 神华集团有限责任公司 | Phenolic substance extraction device and method |
| CN106831455A (en) * | 2016-12-09 | 2017-06-13 | 北京化工大学 | A kind of method of the neutral oil in removal eutectic solvent |
| CN107399779A (en) * | 2017-08-09 | 2017-11-28 | 北京盖雅环境科技有限公司 | A kind of processing method of phenol wastewater |
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| CN108211423A (en) * | 2018-02-28 | 2018-06-29 | 北京化工大学 | It is a kind of by the use of biodegradable compound as the method for phenolic compound in adsorbent adsorbing separation oil |
| CN112391186A (en) * | 2019-08-15 | 2021-02-23 | 中国石油化工股份有限公司 | Method for separating phenolic compounds from coal tar |
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| CN103272407A (en) * | 2013-06-06 | 2013-09-04 | 河北科技大学 | Method for removing residual formic acid in epoxidized fatty acid methyl esters or epoxidized soybean oil by use of eutectic solvent |
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| CN104946303A (en) * | 2015-05-18 | 2015-09-30 | 太原师范学院 | Method for selectively separating phenol mixture from oil |
| CN104946303B (en) * | 2015-05-18 | 2017-04-05 | 太原师范学院 | A kind of method of phenol mixture in Selective Separation oil |
| CN106039763A (en) * | 2016-07-08 | 2016-10-26 | 神华集团有限责任公司 | Phenolic substance extraction device and method |
| CN106831455A (en) * | 2016-12-09 | 2017-06-13 | 北京化工大学 | A kind of method of the neutral oil in removal eutectic solvent |
| CN107399779A (en) * | 2017-08-09 | 2017-11-28 | 北京盖雅环境科技有限公司 | A kind of processing method of phenol wastewater |
| CN107937009A (en) * | 2017-11-10 | 2018-04-20 | 中国五环工程有限公司 | The separation method of phenolic compound in coal tar and DCL/Direct coal liquefaction product |
| CN107937009B (en) * | 2017-11-10 | 2020-08-04 | 中国五环工程有限公司 | Method for separating phenolic compounds from coal tar and direct coal liquefaction product |
| CN108211423A (en) * | 2018-02-28 | 2018-06-29 | 北京化工大学 | It is a kind of by the use of biodegradable compound as the method for phenolic compound in adsorbent adsorbing separation oil |
| CN108211423B (en) * | 2018-02-28 | 2021-01-12 | 北京化工大学 | Method for adsorbing and separating phenolic compounds in oil by using biodegradable compound as adsorbent |
| CN112391186A (en) * | 2019-08-15 | 2021-02-23 | 中国石油化工股份有限公司 | Method for separating phenolic compounds from coal tar |
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