CN102167658A - Technology for complexing, crystallizing, separating and purifying metacresol - Google Patents
Technology for complexing, crystallizing, separating and purifying metacresol Download PDFInfo
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- CN102167658A CN102167658A CN2011100639562A CN201110063956A CN102167658A CN 102167658 A CN102167658 A CN 102167658A CN 2011100639562 A CN2011100639562 A CN 2011100639562A CN 201110063956 A CN201110063956 A CN 201110063956A CN 102167658 A CN102167658 A CN 102167658A
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- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 229940100630 metacresol Drugs 0.000 title claims description 37
- 230000000536 complexating effect Effects 0.000 title claims description 8
- 238000005516 engineering process Methods 0.000 title claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000004202 carbamide Substances 0.000 claims abstract description 29
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000002425 crystallisation Methods 0.000 claims abstract description 23
- 230000008025 crystallization Effects 0.000 claims abstract description 23
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000926 separation method Methods 0.000 claims abstract description 10
- 239000012074 organic phase Substances 0.000 claims abstract description 8
- 239000012071 phase Substances 0.000 claims abstract description 8
- 238000000746 purification Methods 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 7
- 239000000706 filtrate Substances 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 230000007062 hydrolysis Effects 0.000 claims abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
- 239000002002 slurry Substances 0.000 claims abstract description 4
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 claims abstract 2
- 238000002156 mixing Methods 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 36
- 239000002904 solvent Substances 0.000 abstract description 17
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- 238000000034 method Methods 0.000 abstract description 10
- 238000005265 energy consumption Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 1
- 229930003836 cresol Natural products 0.000 abstract 1
- 125000003717 m-cresyl group Chemical group [H]C1=C([H])C(O*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 abstract 1
- 238000009434 installation Methods 0.000 description 13
- 239000002994 raw material Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000197 pyrolysis Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 150000001896 cresols Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000003739 xylenols Chemical class 0.000 description 3
- 238000001311 chemical methods and process Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 238000000053 physical method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 241000270666 Testudines Species 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- -1 meta-cresol compound Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
络合结晶分离提纯间甲酚工艺属于化工分离提纯领域。本发明步骤如下：尿素在混酚中的溶解：向反应器中加入混酚，混酚含有邻甲酚10.907wt％、对甲酚34.276wt％、间甲酚53.176wt％、二甲酚1.641％；再向其中加入尿素，尿素和间甲酚摩尔比为1.0-1.8；通过在水浴或油浴加热升温至85-105℃，持续40-80min，使尿素在混酚溶液中全部溶解；冷却，在60℃温度时加入正己烷，之后在零下10-零下20℃结晶1-2小时；然后将结晶浆液送入过滤器中，完成固、液分离操作；滤液精馏回收，结晶固体加入水，加热在40℃水解，得到水和有机两相；水相回收，有机相即间甲酚。本发明相对于甲苯，用正己烷做络合结晶反应的溶剂时间甲酚的产率更高，且溶剂的使用量可以减少三分之一，用相对较少的能耗就可回收溶剂。
The process of separating and purifying m-cresol by complex crystallization belongs to the field of chemical separation and purification. The steps of the present invention are as follows: dissolving urea in mixed phenol: add mixed phenol to the reactor, mixed phenol contains o-cresol 10.907wt%, p-cresol 34.276wt%, m-cresol 53.176wt%, xylenol 1.641% ; Add urea to it again, the molar ratio of urea and m-cresol is 1.0-1.8; heat up to 85-105°C in a water bath or an oil bath for 40-80min, so that the urea is completely dissolved in the mixed phenol solution; cooling, Add n-hexane at a temperature of 60°C, and then crystallize at minus 10- minus 20°C for 1-2 hours; then send the crystallization slurry into a filter to complete the solid-liquid separation operation; the filtrate is rectified and recovered, and the crystallized solid is added to water, Heating at 40°C for hydrolysis to obtain two phases of water and organic; the water phase is recovered, and the organic phase is m-cresol. Compared with toluene, the present invention uses n-hexane as the solvent for the complex crystallization reaction, and the yield of cresol is higher, and the usage amount of the solvent can be reduced by one-third, and the solvent can be recovered with relatively less energy consumption.
Description
Technical field
The invention belongs to field of chemical separation and purification, relate to a kind of complexing crystallization process and separate purification meta-cresol technology.
Background technology
Cresols is important fine-chemical intermediate, comprise three kinds of isomer, promptly ortho-cresol, p-cresol, meta-cresol are domestic comparatively well sold and in short supply fine chemical product, especially domestic seriously supply falls short of demand to, meta-cresol, annually needs that import is a great deal of satisfies domestic market demand.Meta-cresol is widely used in fields such as agricultural chemicals, medicine, spices, dyestuff, oxidation inhibitor, stopper, UV light absorber, fuel dope, rubber ingredients, coating, fodder additives and synthetic materials.
Between, p-cresol is owing to boiling point separates with conventional method near being difficult to very much.Between, the separation method of p-cresol can be divided into physical method and chemical process generally.Physical method divides azeotropic distn, dissociation extraction method, high pressure crystal partition method, molecular sieve adsorption again: chemical process has class huge legendary turtle compound partition method, alkylation methods etc.
Shang Sihua etc. (chemical research and application, the 15th the 6th phase of volume) have proposed urea and meta-cresol eutectic method compartment/p-cresol; Yin Kailiang (Jiangsu Petrochemical Engineering College journal, the 11st the 2nd phase of volume) has studied the infrared spectra of urea and meta-cresol compound crystal.More than two pieces of articles to meta-cresol and urea crystallization in toluene solvant done introduction.More than research all is to make solvent with toluene.There are shortcomings such as the toluene consumption is big, productive rate is not high and the toluene boiling point is higher relatively, the recovery energy consumption is big in the solvent that toluene is done crystallization reaction.
US3855195A has introduced aromatics (toluene, vinylbenzene, chlorobenzene) when making solvent, the complexing crystallization reaction situation of urea and cresols.Set forth in the JP2010059137 by in cresols, adding urea and water, generated emulsion, method from emulsion from the separation and Extraction meta-cresol.Above-mentioned article is not all mentioned with alkane solvent in the very weak normal hexane of polarity particularly.
Summary of the invention
The object of the invention is to provide the processing method of the separation purification meta-cresol that a kind of solvent load is few, productive rate is high.
Now the present invention is summarized.
(1) dissolving of urea in mixing phenol: adding mixes phenol in reactor, to wherein adding a certain proportion of urea, by in water-bath or oil bath heating, urea is all dissolved and certain time in mixing phenol solution again.
(2) crystallization: along with the reduction of temperature, meta-cresol can and constantly be separated out with the crystalline form with complex compound that urea forms, and along with the increase of crystalline amount, the viscosity of mixture is also increasing.When temperature is reduced to a certain degree, in mixture, at the uniform velocity dripping a certain amount of normal hexane as solvent.
(3) crystal solution is separated: filter the xln that experiment produces, with the normal hexane washing leaching cake for several times, obtain the urea one meta-cresol complex compound crystal of white in the time of suction filtration.
(4) crystallisate pyrolysis: white crystal is placed on carries out pyrolysis in 40 ℃ in the water-bath, the meta-cresol that produces after the pyrolysis is present in organic phase, and urea then is dissolved in aqueous phase.
(5) separatory: to separating funnel, static layering treats that layering obviously separates lower floor's water in the back, gets upper organic phase and does purity assay the solution after the pyrolysis.
Complexing Crystallization Separation purification meta-cresol technology, it is characterized in that, step is as follows: the dissolving of urea in mixing phenol: add in reactor and mix phenol, mixed phenol contains ortho-cresol 10.907wt%, p-cresol 34.276wt%, meta-cresol 53.176wt%, xylenol 1.641%; To wherein adding urea, urea and meta-cresol mol ratio are 1.0-1.8 again; By at water-bath or oil bath heat temperature raising to 85-105 ℃, continue 40-80min, make urea all dissolvings in mixing phenol solution; Cooling adds the normal hexane in the normal hexane groove when 60 ℃ of temperature, the volume ratio of normal hexane and meta-cresol is 1-3; At the subzero 20 ℃ of crystallization 1-2 of subzero 10-hours, finish crystallization operation afterwards; Then slurry is sent in the strainer, finished the solid, liquid lock out operation; Filtrate rectifying is reclaimed, and crystalline solid adds entry, and heating obtains water and organic two-phase 40 ℃ of hydrolysis; Water reclaims, and organic phase is a meta-cresol.
With respect to toluene, the productive rate of meta-cresol is higher when making the solvent of complexing crystallization reaction with normal hexane, and the usage quantity of solvent can reduce 1/3rd.When solvent is reclaimed in rectifying, relatively low because of the boiling point of normal hexane, can use less relatively energy consumption with regard to recyclable solvent.
Description of drawings
Fig. 1 process flow sheet of the present invention.
Embodiment
In conjunction with the accompanying drawings the present invention is summarized in detail now.Accompanying drawing is the process flow sheet of complexing Crystallization Separation meta-cresol.Raw material mixes the mixed phenol of the storage of raw materials in the phenol groove.The raw material that reacts used mixes phenol and mainly contains ortho-cresol (10.907wt%), p-cresol (34.276wt%), meta-cresol (53.176wt%), xylenol (1.641%) for mixing the phenol isomer.Raw material mixes phenol and enters in the reactor, and simultaneously, urea is also put into reactor.Urea and meta-cresol mol ratio are 1.0-1.8.In reactor, be warming up to 85-105 ℃, continue 40-80min.Cooling adds the normal hexane in the normal hexane groove when 60 ℃ of temperature, the volume ratio of normal hexane and meta-cresol is 1-3.Afterwards, reaction solution enters crystallizer.Subzero 10-20 ℃ crystallization 1-2 hour, finish crystallization operation.Then slurry is sent in the strainer, finished the solid, liquid lock out operation.Filtrate enters rectifying tower, reclaims normal hexane by rectifying.The crystalline solid phase that is filtered out by strainer enters splitter, and the water in splitter adding tank decomposes about 40 ℃ simultaneously, obtains organic phase and water two-phase, and water reclaims, and organic phase is a meta-cresol.Whole technology has only raw material to mix the phenol inlet and by-product mixes phenol outlet and the outlet of product meta-cresol, and other normal hexanes, urea can be at system's internal recycle, and this flow process can be added the normal hexane and the urea of loss at any time.
Example (1)
In reactor, add raw material and mix phenol (the mixed phenol composition of raw material: ortho-cresol 10.907wt%, p-cresol 34.276wt%, meta-cresol 53.176wt%, xylenol 1.641%), add complexing agent urea again, the mol ratio that its add-on and raw material mix meta-cresol in the phenol is 1.4: 1, puts into oil bath, be warming up to 95 ℃, reacted one hour.After reaction is finished, when question response liquid is cooled to 60 ℃, drip normal hexane, the volume ratio that normal hexane consumption and raw material mix phenol is 2.Dropwise the back there-necked flask is placed in the low temperature thermostat bath,, filter after 1 hour-15 ℃ of maintenances, filtrate rectifying is reclaimed, and crystalline solid adds the deionized water of three times of quality, and heating hydrolysis obtains water and organic two-phase.Organic phase is the product meta-cresol.With gc analysis meta-cresol product.Experimental result sees Table 1.
[Comparative Examples] example 2 experimental installations and operation are with example (1), and just the solvent that drips is that toluene is while the volume ratio of the mixed phenol of toluene consumption and raw material is 3.Experimental result sees Table 1.
[Comparative Examples] example 3 experimental installations and operation are with example (2), and just crystallization time is 2 hours.Experimental result sees Table 1.
Example 4 experimental installations and operation are with example (1), and just crystallization time is 2 hours.Reaction result sees Table 1.
Example 5 experimental installations and operation are with example (1), and just the normal hexane consumption that drips is 3 with the volume ratio of the mixed phenol of raw material.Experimental result sees Table 1.
Example 6 experimental installations and operation are with example (1), and just the normal hexane consumption that drips is 1 with the specific volume ratio that raw material mixes phenol.Experimental result sees Table 1.
Example 7 experimental installations and operation are with example (1), and just the temperature of complex reaction is 105 ℃.Experimental result sees Table 1.
Example 8 experimental installations and operation together routine (1) the just temperature of complex reaction are 85 ℃.Reaction result sees Table 1.
Example 9 experimental installations and operation be with example (1), just and Tc be 2 hours for-10 ℃ and crystallization time.Experimental result sees Table 1.
Example 10 experimental installations and operation are with example (1), and just Tc is-20 ℃.Experimental result sees Table 1
Example 11 experimental installations and operation are with example (1), and just the reaction times is 40min, and experimental result sees Table 1
Example 12 experimental installations and operation are with example (1), and just the reaction times is 80min, and experimental result sees Table 1
Example 13 experimental installations and operation are with example (1), and just urea and meta-cresol mol ratio are 1.0: 1, and experimental result sees Table 1
Example 14 experimental installations and operation are with example (1), and just urea and meta-cresol mol ratio are 1.8: 1, the results are shown in Table 1
Table 1
The present invention produces a desired effect.When the effect during as the solvent of crystallization reaction with normal hexane will be significantly better than the time with toluene effect, and the relative toluene consumption of the consumption of normal hexane has reduced 1/3rd.When solvent is reclaimed in rectifying, relatively low because of the boiling point of normal hexane, can use less relatively energy consumption with regard to recyclable solvent.
Claims (1)
1. complexing Crystallization Separation purification meta-cresol technology, it is characterized in that, step is as follows: the dissolving of urea in mixing phenol: add in reactor and mix phenol, mixed phenol contains ortho-cresol 10.907wt%, p-cresol 34.276wt%, meta-cresol 53.176wt%, xylenol 1.641%; To wherein adding urea, urea and meta-cresol mol ratio are 1.0-1.8 again; By at water-bath or oil bath heat temperature raising to 85-105 ℃, continue 40-80min, make urea all dissolvings in mixing phenol solution; Cooling adds normal hexane when 60 ℃ of temperature, the volume ratio of normal hexane and meta-cresol is 1-3; At the subzero 20 ℃ of crystallization 1-2 of subzero 10-hours, finish crystallization operation afterwards; Then slurry is sent in the strainer, finished the solid, liquid lock out operation; Filtrate rectifying is reclaimed, and crystalline solid adds entry, and heating obtains water and organic two-phase 40 ℃ of hydrolysis; Water reclaims, and organic phase is a meta-cresol.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN103333052A (en) * | 2013-07-25 | 2013-10-02 | 北京旭阳化工技术研究院有限公司 | Method for preparing pure p-cresol and pure m-cresol by separating industrial mixed p-cresol and m-cresol |
| CN104098445A (en) * | 2014-07-03 | 2014-10-15 | 河北华旭化工有限公司 | Method for extracting m-cresol from mixture of m-cresol and p-cresol |
| CN104324519A (en) * | 2014-11-04 | 2015-02-04 | 中国科学院过程工程研究所 | Method for directly separating phenols from coal pyrolytic oil |
| CN108558609A (en) * | 2018-05-10 | 2018-09-21 | 江苏焕鑫新材料股份有限公司 | A kind of polyphenol mixture recycling purifying technique |
| 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 |
| CN114570053A (en) * | 2022-03-22 | 2022-06-03 | 山西永东化工股份有限公司 | Method for separating and purifying o-cresol, m-cresol and p-cresol of coal tar |
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Cited By (14)
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| 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 |
| CN103333051B (en) * | 2013-07-18 | 2015-12-23 | 北京旭阳化工技术研究院有限公司 | A kind of method of producing meta-cresol |
| CN103333052B (en) * | 2013-07-25 | 2015-07-29 | 北京旭阳化工技术研究院有限公司 | Between a kind of separation industries to mixture cresol to prepare the method for pure p-cresol and pure meta-cresol |
| CN103333052A (en) * | 2013-07-25 | 2013-10-02 | 北京旭阳化工技术研究院有限公司 | Method for preparing pure p-cresol and pure m-cresol by separating industrial mixed p-cresol and m-cresol |
| CN104098445A (en) * | 2014-07-03 | 2014-10-15 | 河北华旭化工有限公司 | Method for extracting m-cresol from mixture of m-cresol and p-cresol |
| CN104098445B (en) * | 2014-07-03 | 2016-05-11 | 河北华旭化工有限公司 | A kind of method of extracting metacresol from M-and P-cresols mixture |
| CN104324519A (en) * | 2014-11-04 | 2015-02-04 | 中国科学院过程工程研究所 | Method for directly separating phenols from coal pyrolytic oil |
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| CN113501748A (en) * | 2021-07-05 | 2021-10-15 | 湘潭大学 | Method for separating m-cresol and p-cresol |
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