CN104230669B - Separation and purification method of m-cresol - Google Patents
Separation and purification method of m-cresol Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
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Abstract
The invention relates to a separation and purification method of m-cresol. The separation and purification method comprises the following steps: a) complexing: adding mixed cresol, urea and a mixed solvent formed by toluene and liquid alkane into a reactor, stirring, heating to increase the temperature to 65-90 DEG C, performing heat preservation for 1-2h, reducing the temperature to 40-60 DEG C, then cooling and crystallizing at the temperature of 0-20 DEG C for 1-2h, and filtering to obtain a complex solid and filtrate A; and b) decomplexing: adding the complex solid obtained in the step a) into an ether type solvent, stirring at the temperature of 10-60 DEG C, performing decomplexing reaction for 0.5-3h, and filtering to obtain urea and filtrate B; and performing decompression rectification on the filtrate B to obtain m-cresol. The method for separating m-cresol from mixed cresol is high in product purity, simple in process, low in solvent consumption, high in recovery rate and low in energy consumption and can operate at normal pressure, prevent the production of three wastes in a separation process and realize recycling of resources, so that the method is environment-friendly.
Description
Technical field
The invention belongs to field of chemical separation and purification, it is related to a kind of side separating metacresol from cresols
Method.Specifically, using complexation-crystallization separation cresols, simply and efficiently obtain high-purity metacresol.
Background technology
Cresol is a kind of important chemical products, and it includes three kinds of isomerss：Orthoresol, paracresol,
Metacresol, metacresol is mainly as synthesising complex E, spice, pyrethroid pesticide, antioxidant
Important intermediate, increasing with downstream product demand, domestic metacresol is often in that supply falls short of demand
Situation, therefore, high-purity metacresol product has wide market prospect.
At present, the production of cresol mainly adopts toluene sulfonation alkali fusion, isopropyl toluene method, alkylation of phenol
Method, chlorination toluene Hydrolyze method, but in process of production orthoresol, paracresol, three kinds of isomers of metacresol with
Different ratios exists simultaneously；In addition, the cresol extracting from coal tar is often also mixture, fail fully
Separate and utilize.In cresols, the separation of Isomers is the problem of a focus, and orthoresol boiling point is relatively low,
Can be separated from their mixture by rectification, and paracresol, metacresol boiling point closely (phase
Differ from 0.3 DEG C) it is difficult to by the method for conventional distillation separately.
Between/separation method of paracresol mixture can be divided into physical method and chemical method two big class, physics
Method has azeotropic distillation method, dissociation extraction method, high voltage junction crystallization and molecular sieve absorption process；Chemical method
There are complexation-crystallization partition method, alkylation partition method etc..Wherein, azeotropic distillation method, exists in paracresol sodium
Under the conditions of, paracresol azeotrope with water steams, but energy consumption is too big, and phenol wastewater is difficult to process.High pressure crystal
Separate, pressure is up to 100～300MPa, too high to equipment requirements, and investment is big.Molecular sieve absorption process,
Because the selection of molecular sieve and preparation are difficult, mobile absorption bed apparatus and control system are complicated, only external UOP,
There is more ripe technique in Toray company；Alkylation partition method, comprises alkylation, two processes of alkylation removal,
Reaction needs more acidic catalyst, and acid medium leads to equipment corrosion serious, and alkylation is not thoroughly also given
Technological process brings complexity.
Although complexation-crystallization partition method, simple to operate, technological process is short, and raw material is easy to get, and chelating agent, molten
Agent reusable edible, but also more or less there are disadvantages that：
It is chelating agent that US3855195 adopts carbamide, and aromatic compound is solvent, carries out complexation-crystallization.CN
Normal hexane is adopted to be solvent in 102167658A complexation-crystallization method separating-purifying metacresol technique, reactant liquor drops
Wen Hou, then Deca solvent, non-disposable feed intake, crystallization temperature low (- 20～-10 DEG C), after hydrolysis, from water
Reclaim carbamide energy consumption in solution larger, and corresponding phenolic wastewater treatment is relatively difficult.
And washed for complex reaction using hexamethylene or petroleum ether in CN 103204766A, CN103333052A
Wash the solvent in stage, the metacresol-urea crystal of the white needles complexation obtaining, through toluene high temperature pyrolysis,
Solvent consumption is larger, energy consumption is big.
It is directed to add solvent (non-once during above-mentioned patent complexation-crystallization in complexation stage temperature-fall period
Property feed intake), gained complex need to wash purification, and it is relative complex to there is technical process, long the production cycle, solution
Complexing solvent consumption is big, and temperature is higher, the shortcomings of energy consumption is big.
Content of the invention
The technical problem to be solved is：There is provided a kind of by/mixture of paracresol is through once
Property Separation by Complexation, obtains pure metacresol (purity reaches 99.5%), and by with Oxalic Acid Method Separation by Complexation pair
Cresol circulation combination, thus realize by between/paracresol mixture carries out detached method；I.e. cresols warp
Cross and disposably separate, obtain pure paracresol and pure metacresol simultaneously, and be capable of circulation complexation-crystallization and divide
From.
For solving above-mentioned technical problem, the technical solution used in the present invention is：A kind of separating-purifying of metacresol
Method, its step is：
A) complexation：Cresols, carbamide, the mixing that toluene is formed is added with liquid alkane in reactor
Solvent, stirring, it is heated to 65～90 DEG C, after insulation 1～2h, be cooled to 40～60 DEG C, Ran Hou
0～20 DEG C of crystallisation by cooling 1～2h, filters, obtains complex solid and filtrate A；
Described filtrate A reclaims toluene, liquid alkane through rectification under vacuum, for step a) recycling, same
When, obtain the mother solution rich in paracresol, as the dispensing of Oxalic Acid Method Separation by Complexation paracresol；
B) solve complexation：Gained complex solid in step a) is added in ether solvent, in 10～60 DEG C of bars
Under part, stirring, solve complex reaction 0.5～3h, filter, obtain carbamide and liquor B；
Described carbamide supplies step a) to reuse, and described liquor B is between rectification under vacuum respectively obtains
Cresol, ether solvent, ether solvent supplies step b) to reuse.
In step a), the consisting of of described cresols：Paracresol 13～45wt.%, metacresol
50～86wt.%, 2,6- xylenol 1～6wt.%；Or raw material cresols are through oxalic acid complexation-crystallization method (specially
Sharp application number：201410280902.5, application is entitled：A kind of method of separating-purifying paracresol, its step
Suddenly it is：
1) complexation：Add toluene and chelating agent oxalic acid in reactor, be warming up to 60～70 DEG C, add mixed
Close cresol, insulation reaction 1～3h, filter, obtain filtrate and the paracresol-oxalate complex of white fine particulate
Crystal crude product；
The addition of described toluene is 2.1 ± 0.2 times of cresols quality, and described oxalic acid addition is
1.0 ± 0.1 times of paracresol mole in cresols；
2) purification：By step 1) in paracresol-oxalate complex crystal crude product be added in purification solvent,
Stirring 1 ± 0.5h, filters, obtains paracresol-oxalate complex sterling；
3) solve complexation：By step 2) paracresol-oxalate complex sterling of gained is added to the water, heats up
To 40～80 DEG C, insulation reaction 1.5 ± 0.5h, while hot (40～80 DEG C) isolate upper organic phase, lower floor
Aqueous phase is extracted with toluene, and extract is incorporated to upper organic phase；
4) distill：By step 3) upper organic phase distillation remove solvent, obtain paracresol, the first distilling out
Benzene is applied to step 1) or step 3) in；
5) reclaim chelating agent：By step 3) in lower floor's aqueous phase distill to obtain oxalic acid, be applied to step 1),
Water is back to step 3) in.
Step 1) in, described cresols comprise paracresol, metacresol and 2,6- xylenol, its group
Become：Paracresol 10～90wt.%, metacresol 10～90wt.%, 2,6- xylenol 0～5wt.%.
Step 1) in, described chelating agent oxalic acid is anhydrous oxalic acid or two oxalic acid hydrates.
In step 2) in, purification solvent is the mixture of toluene-methanol, and the volume content of wherein methanol is
1%～20%, preferably 2%～10%.
Step 2) in, during filtration, the temperature of purification solvent is 0～24 DEG C, preferably 0～5 DEG C.
Step 2) in, the quality of purification solvent is 1～4 times of paracresol-oxalate complex crude product quality, excellent
Elect 1～2 times as.
Step 3) in, in solution complex reaction, the consumption of water is 1～5 times of paracresol-oxalate complex quality,
It is preferably 1～3 times.
Step 3) in, the temperature of solution complex reaction is preferably 45～55 DEG C.) isolate the residue after paracresol
Mother solution, the composition of cresols in mother solution：Paracresol 14.5～16.3wt.%, metacresol 80.1～84.6wt.%,
2,6- dimethyl cresol 0.8～4wt.%.
In step a), described carbamide addition is 0.5～1.3 with the mol ratio of metacresol in cresols；
Described liquid alkane is selected from pentane, hexane, hexamethylene, normal heptane, octane, 60～90 DEG C of boiling range
One or more of petroleum ether；Toluene is 4 with the volume ratio of liquid alkane:1～1:5；Toluene and liquid alkane
The mixed solvent that hydrocarbon is formed is 1 with the mass ratio of cresols:1～3:1；Insulation reaction temperature is preferably
75～90 DEG C, more preferably 80～85 DEG C, carbamide is enable fully to dissolve；Described crystallisation by cooling
Temperature is preferably 0～10 DEG C, and further preferred 5～10 DEG C, suitable crystallization temperature is more suitable for industrialized production.
In wherein step b), described ether solvent is just being selected from ether, positive propyl ether, diisopropyl ether, ethyl
Butyl ether, n-butyl ether, cyclopentyl methyl ether, methyl tertiary butyl ether(MTBE), diamyl ether, isoamyl ether, two n-hexyl ethers,
Oxolane, 2- methylfuran, 1,3- dioxolane, Isosorbide-5-Nitrae-dioxane, 2,2 ＇-dichloro two
Ether, 2,2 ＇-dichlorodiisopropyl ether, dimethoxymethane, diethoxymethane, 1,1- dimethoxy
Ethane, 1,1- diethoxyethane, methyl phenyl ethers anisole, ethyl phenyl ether, dibenzyl ether, Pentamethylene oxide., epoxy chlorine
One or more of propane；Described ether solvent be preferably methyl tertiary butyl ether(MTBE), diisopropyl ether, methyl phenyl ethers anisole,
One or more of n-butyl ether, cyclopentyl methyl ether, dioxane.Described ether solvent is solid with complex
Body mass ratio is 0.5:1～2:1.The temperature of described ether solvent solution complex reaction is preferably 20～60 DEG C, enters
One step is preferably 20～45 DEG C, and temperature is relatively low, and energy consumption is little, easy to operate.Solution complexation time is preferably 0.5～1h,
Ether solvent solution complexation efficiency high, the time used is short, shortens the production cycle.
Beneficial effect：This method by the way of disposably feeding intake, with toluene and liquid alkane as solvent,
Certain proportion is issued to the optimum polarity of complex crystallization, and solvent load is few, after solid-liquid separation, powdery complexation
Thing solid need not wash purification；Solution complexation, at a lower temperature, using ether solvent, quickly and efficiently divides
From obtaining highly purified metacresol.
The method separating metacresol from cresols, product purity is high, and process is simple, and atmospheric operation is molten
Agent consumption is few and the response rate is high, less energy consumption, does not produce the three wastes, resource circulation utilization in separation process, is one
Plant green environment friendly method.
Specific embodiment
Embodiment 1
With cresols (paracresol 16.5wt.%, metacresol 81.6wt.%, 2,6- dimethyl cresol 1.9wt.%)
For raw material, the mixed solvent of cresols, carbamide, toluene and hexane formation is added in reactor in the lump,
Wherein carbamide and the molar ratio of metacresol in cresols are 0.7:1, the mixing that toluene is formed with hexane is molten
The addition of agent and the mass ratio of cresols are 1:1, in mixed solvent, toluene and the volume ratio of hexane are
3:1, reactor is heated to 85 DEG C, is incubated 2h, is then cooled to 50 DEG C, be incubated 1h, then
Crystallize 1.5 hours in 7 DEG C, filter, obtain white powder complex solid and filtrate A；
Filtrate A reclaims toluene, hexane through rectification under vacuum, for complex reaction recycling, obtains meanwhile
Mother solution rich in paracresol, as the dispensing of Oxalic Acid Method Separation by Complexation paracresol；
White powder complex solid is added in methyl tertiary butyl ether(MTBE), temperature is 25 DEG C, methyl tertiary butyl ether(MTBE)
It is 1 with complex solid mass ratio:1, stirring, after reaction 1h, filter, obtain carbamide and liquor B, urine
Element is reused for complex reaction.
Liquor B respectively obtains metacresol, methyl tertiary butyl ether(MTBE) through rectification under vacuum, and methyl tertiary butyl ether(MTBE) is for solution
Complexation reuses.
Embodiment 2
Experimental provision and operation with embodiment 1, simply the consisting of of raw material cresols：Paracresol 40wt.%,
Metacresol 57wt.%, 2,6- dimethyl cresol 3wt.%.
Embodiment 3
With embodiment 1, simply raw material cresols are derived from self-produced cresols (to first for experimental provision and operation
Phenol 71.3wt.%, metacresol 28.2wt.%, 2,6- dimethyl cresol 0.5wt.%) through oxalic acid complexation-crystallization method
Isolate the remaining mother solution after paracresol, in mother solution, cresols consists of：Paracresol 15.9wt.%,
Cresol 82.9wt.%, 2,6- dimethyl cresol 1.2wt.%.
Embodiment 4
, with embodiment 1, simply the addition of carbamide and the molar ratio of metacresol are for experimental provision and operation
1.1:1.
Embodiment 5
, with embodiment 1, simply in mixed solvent, toluene and the volume ratio of hexane are for experimental provision and operation
1:1, the mixed solvent that toluene is formed with hexane is 2 with the mass ratio of cresols:1.
Embodiment 6
With embodiment 4, simply mixed solvent is replaced by toluene and normal heptane for experimental provision and operation, toluene with
The volume ratio of normal heptane is 1:2.
Embodiment 7
With embodiment 4, simply mixed solvent is replaced by toluene and petroleum ether (boiling range for experimental provision and operation
60～90 DEG C), toluene is 1 with the volume ratio of petroleum ether (60～90 DEG C of boiling range):3.
Embodiment 8
Experimental provision and operation, with embodiment 4, simply adopt diisopropyl ether during solution complexation.
Embodiment 9
Experimental provision and operation with embodiment 4, simply adopt methyl phenyl ethers anisole during solution complexation, its addition with
Complex solid mass ratio is 0.5:1.
Embodiment 10
Experimental provision and operation with embodiment 4, simply adopt n-butyl ether during solution complexation, its addition with
Complex solid mass ratio is 1.5:1.
Embodiment 11
Experimental provision and operation, with embodiment 4, simply adopt cyclopentyl methyl ether during solution complexation, its addition
Amount and complex solid mass ratio are 2:1.
Embodiment 12
Experimental provision and operation, with embodiment 4, simply adopt dioxane during solution complexation.
Embodiment 13
Experimental provision and operation, with embodiment 11, simply solve complexation process, temperature is 45 DEG C.
The purity of the separating obtained metacresol product of embodiment 1～13, yield, the results are shown in Table 1.Between/paracresol
Qualitative be by buy standard sample carry out contrast retention time show, the detection of purity uses gas phase
Chromatograph external standard curve method.Detecting instrument is Shimadzu gas chromatograph GC-2010, the chiral capillary of α-DEX 120
Post, model specification is：30m × 0.25mm ID × 0.25 μm, fixing phase：Nonbonding phase, SPB-35 poly- (35%
Phenyl/65% methylsiloxane) in contain 20% Hypermethylation alpha-cyclodextrin.
Table 1
| Embodiment | Metacresol purity % | Metacresol yield % |
| Embodiment 1 | 99.0% | 78% |
| Embodiment 2 | 98.9% | 75% |
| Embodiment 3 | 99.1% | 82% |
| Embodiment 4 | 99.2% | 81% |
| Embodiment 5 | 99.1% | 83% |
| Embodiment 6 | 99.7% | 88% |
| Embodiment 7 | 99.5% | 82% |
| Embodiment 8 | 99.1% | 79% |
| Embodiment 9 | 99.3% | 83% |
| Embodiment 10 | 99.4% | 90% |
| Embodiment 11 | 99.6% | 86% |
| Embodiment 12 | 99.1% | 85% |
| Embodiment 13 | 99.5% | 82% |
Present invention achieves following effect：
1) using disposably feeding intake, complex solid need not wash purification, simplify and operated for complex reaction
Journey, shortens the production cycle.
2) complexation-crystallization, using optimum solvent polarity, enables the complex that metacresol is formed with carbamide
Crystallization separates out to greatest extent；The suitable commercial production of crystallization temperature, energy consumption is low.
3) adopt ether solvent first, carry out solving complexation in room temperature, solvent load is few, efficiently, quickly,
And solve the problems, such as using high temperature solution complexation energy consumption is big, solvent loss is big.
4) step being related to is atmospheric operation, carbamide, toluene, and liquid alkane, ether solvent all reclaim
Recycle, separation process three wastes produce, and are environmentally friendly separating technology.
5) can be combined with Oxalic Acid Method Separation by Complexation paracresol technique, thus the circulation realizing cresols divides
From.
Claims (6)
1. a kind of process for separation and purification of metacresol, its step is：
A) complexation：Cresols, carbamide, toluene and liquid alkane shape is added in reactor
The mixed solvent becoming, stirring, it is heated to 65～90 DEG C, be incubated 1～2h at 65～90 DEG C
Afterwards, it is cooled to 40～60 DEG C, then in 0～20 DEG C of crystallisation by cooling 1～2h, filter, obtain complexation
Thing solid and filtrate A；
B) solve complexation：Gained complex solid in step a) is added in ether solvent,
Under the conditions of 10～60 DEG C, stirring, solve complex reaction 0.5～3h, filter, obtain carbamide and liquor B；
Described liquor B obtains metacresol, ether solvent respectively through rectification under vacuum；
In step a), the consisting of of described cresols：Paracresol 14.5～16.3wt.%,
Metacresol 80.1～84.6wt.%, 2,6- dimethyl cresol 0.8～4wt.%；
In step a), described carbamide is 0.5～1.3 with the mol ratio of metacresol in cresols；
In step a), described liquid alkane is selected from pentane, hexane, hexamethylene, positive heptan
One or more of alkane, octane, petroleum ether of 60～90 DEG C of boiling range；
In step a), toluene is 4 with the volume ratio of liquid alkane:1～1:5；Toluene and liquid alkane
The mixed solvent that hydrocarbon is formed is 1 with the mass ratio of cresols:1～3:1.
2. the process for separation and purification of a kind of metacresol according to claim 1, its feature
It is：In step a), insulation reaction temperature is 75～90 DEG C；The temperature of described crystallisation by cooling
Spend for 0～10 DEG C.
3. the process for separation and purification of a kind of metacresol according to claim 1, its feature
It is：In step b), described ether solvent be selected from ether, positive propyl ether, diisopropyl ether,
Ethyl n-butyl ether, n-butyl ether, cyclopentyl methyl ether, methyl tertiary butyl ether(MTBE), diamyl ether, two different
Amyl ether, two n-hexyl ethers, oxolane, 2- methylfuran, 1,3- dioxolane, 1,
4- dioxane, 2,2 ＇-dichlorodiethyl ether, 2,2 ＇-dichlorodiisopropyl ether, dimethoxy
Methane, diethoxymethane, 1,1- dimethoxy-ethane, 1,1- diethoxyethane, benzene
Methyl ether, ethyl phenyl ether, dibenzyl ether, Pentamethylene oxide., epoxychloropropane one or more；Institute
The ether solvent stated and complex solid mass ratio are 0.5:1～2:1.
4. the process for separation and purification of a kind of metacresol according to claim 1 or 3, its
It is characterised by：In step b), described ether solvent is methyl tertiary butyl ether(MTBE), diisopropyl ether,
One or more of methyl phenyl ethers anisole, n-butyl ether, cyclopentyl methyl ether, dioxane.
5. the process for separation and purification of a kind of metacresol according to claim 1, its feature
It is：In step b), the temperature of described ether solvent solution complex reaction is 20～60 DEG C,
Solution complexation time is 0.5～1h.
6. the process for separation and purification of a kind of metacresol according to claim 1, its feature
It is：Toluene that described filtrate A reclaims through rectification under vacuum, liquid alkane, for step a)
Recycling；
In step b), described carbamide supplies step a) to reuse, described liquor B warp
Crossing the ether solvent that rectification under vacuum obtains supplies step b) to reuse.
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| CN107879900B (en) * | 2017-12-22 | 2024-05-14 | 中触媒新材料股份有限公司 | Process method for separating and purifying cresol mixed isomer |
| CN108947777B (en) * | 2018-05-31 | 2021-09-10 | 江苏焕鑫新材料股份有限公司 | Enrichment and separation process of low-concentration multi-component phenol-containing mixture |
| CN111909004A (en) * | 2019-05-10 | 2020-11-10 | 陕西省石油化工研究设计院 | Method for separating m-cresol from p-cresol |
| CN112745199A (en) * | 2019-10-31 | 2021-05-04 | 湖北健翔生物制药有限公司 | Preparation method of pharmaceutic adjuvant injection interstage cresol |
| CN113501748A (en) * | 2021-07-05 | 2021-10-15 | 湘潭大学 | Method for separating m-cresol and p-cresol |
| CN115124408B (en) * | 2022-07-28 | 2023-07-25 | 天津大学 | Co-crystallization resolution method of cresol isomeride mixture |
| CN115304456B (en) * | 2022-08-09 | 2023-09-22 | 宁夏派可威生物科技有限公司 | Separation process for separating m-cresol from urea |
| CN115636735B (en) * | 2022-10-27 | 2024-05-28 | 北京化工大学 | Process method for extracting and separating m-cresol and p-cresol mixture |
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|---|---|---|---|---|
| US3855195A (en) * | 1970-07-22 | 1974-12-17 | Sumitomo Chemical Co | Method for producing pure m-cresol |
| CN103204766A (en) * | 2013-03-01 | 2013-07-17 | 北京旭阳化工技术研究院有限公司 | Method for separating and purifying m-cresol from mixture of m-cresol and p-cresol |
| CN103333051A (en) * | 2013-07-18 | 2013-10-02 | 北京旭阳化工技术研究院有限公司 | Method for producing m-cresol |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3855195A (en) * | 1970-07-22 | 1974-12-17 | Sumitomo Chemical Co | Method for producing pure m-cresol |
| CN103204766A (en) * | 2013-03-01 | 2013-07-17 | 北京旭阳化工技术研究院有限公司 | Method for separating and purifying m-cresol from mixture of m-cresol and p-cresol |
| CN103333051A (en) * | 2013-07-18 | 2013-10-02 | 北京旭阳化工技术研究院有限公司 | Method for producing m-cresol |
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