CN107266294A - A kind of purification process of the guaiacol first product synthesized for catechol with methanol oxidation - Google Patents
A kind of purification process of the guaiacol first product synthesized for catechol with methanol oxidation Download PDFInfo
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Abstract
The invention discloses a kind of purification process of the guaiacol first product synthesized for catechol with methanol oxidation；The first product guaiacol of the present invention first obtains the guaiacol of high-purity after fusion-crystallization, heating sweating；The mother liquor produced in the residual mother liquor and sweating effort of crystallization process is collected respectively, purity higher than 90% mother liquor and raw material merge direct crystallization, purity less than 90% component by rectification under vacuum make guaiacol be enriched to meet crystallization require after crystallized again；Rectification under vacuum must be rich in the mixture of 1,2-dimethoxy benzene, carry out back extraction processing, obtain pure 1,2-dimethoxy benzene sterling.Purge process energy consumption of the present invention is low, and product quality is high, and separation costs are low；While high-purity guaiacol principal product is obtained, accessory substance 1,2-dimethoxy benzene can be also obtained；The guaiacol finished product purity of acquisition can reach more than 99.5%, and the wherein methyl guaiacol and 4 of impurity 6 and 3 methyl guaiacol and 4 contents is below 0.05%.
Description
Technical field
The invention belongs to synthetic perfume technical field, and in particular to the guaiaci lignum that a kind of catechol is synthesized with methanol oxidation
The purification process of phenol first product.
Background technology
Guaiacol is a kind of important fine chemical product, can be used as food additives, spices, and synthesis of vanillin
With the raw material of guaiacol glycerol ether.Whole world annual requirement reaches nearly 20,000 tons at present.Guaiacol mainly has two kinds of synthesis sides
Method, is o-nitrochlorobenzene method and catechol method (referring to publication CN101081805) respectively, because catechol method is relative
More clean, there is the trend for substituting o-nitrochlorobenzene method comprehensively at present.The reaction equation of catechol method synthesizing guaiacol is shown in
Fig. 1.
The reaction of catechol and methanol-fueled CLC guaiacol is general under the effect of acid solid acid catalyst, in fixed bed
Reaction is completed in reactor, General reactions temperature is at 270 DEG C or so.Because reaction temperature is higher, wound is cured in generation target product
While wooden phenol, part 1,2-dimethoxy benzene, 6- methyl guaiacol and 4s and the generation of 3- methyl guaiacol and 4s accessory substance are had, these three
The ratio regular meeting of accessory substance changes with catalyst type and is varied from reaction temperature, but general between 0.2~3.0%.Just
6- methyl guaiacol and 4s and 3- methyl guaiacol and 4s in product guaiacol can influence the synthesis of follow-up vanillic aldehyde, therefore, reaction
The first product guaiacol of acquisition needs to obtain the higher product of purity after being isolated and purified, and needs control to be cured in actual production
6- methyl guaiacol and 4s and 3- methyl guaiacol and 4s content are less than 0.05% in the wooden phenol of wound.
The purification process being currently known is the difference using product and raw material and accessory substance boiling point, using conventional rectifying side
Method is purified.And the boiling point of 1,2-dimethoxy benzene, the boiling point of 6- methyl guaiacol and 4s and 3- methyl guaiacol and 4s and guaiacol
Difference is smaller, and rectification efficiency is very low.And contained a small amount of 6- methyl guaiacol and 4s may be produced to the use of product in the product
Very big influence, and the fusing point of vanillic aldehyde can be significantly affected.As synthesized with the guaiacol containing a small amount of 6- methyl guaiacol and 4s
Vanillic aldehyde, can be mixed into 5- methyl vanillins in vanillic aldehyde (see Fig. 2).The physical property and vanillic aldehyde of 5- methyl vanillins are very
It is close, be difficult to adopt the conventional methods such as rectifying or crystallization and be removed, can not only significantly affect the yield of vanillic aldehyde product with it is pure
Degree, and the fusing point of vanillic aldehyde finished product can be influenceed.Influence of the 3- methyl guaiacol and 4s to synthesis of vanillin and 6- methyl guaiaci lignum
Phenols is seemingly.Therefore, in the guaiacol product of synthesis of vanillin, 6- methyl guaiacol and 4s to contain with 3- methyl guaiacol and 4s
Amount is required to be less than 0.05% in actual production.And the boiling of 6- methyl guaiacol and 4s, 3- methyl guaiacol and 4s and guaiacol
Point difference is smaller, although can be separated by the method for rectifying, but separating difficulty is very big, and energy consumption is larger.In experiment
Room reaches 5 to be separated off a small amount of 6- methyl guaiacol and 4s, it is necessary to number of theoretical plate reaches 50 rectifying column in reflux ratio：1
In the case of, a yield also only 50% or so.Multitower is generally required in plant produced and is used in series just to can ensure that product quality,
The steam energy consumption of ton product separation process reaches more than 10 tons.
The content of the invention
In order to solve 1,2-dimethoxy benzene, 6- methyl guaiaci lignum in the guaiacol that catechol is produced with methanol synthesis
The problem of phenol, 3- methyl guaiacol and 4s separating-purifying are difficult, is used for catechol it is an object of the invention to provide one kind
The purification process of the guaiacol first product synthesized with methanol oxidation.Present invention process method is simple, energy consumption reduction, while by-product is adjacent
Phenylene dimethyl ether, applied widely, treatment effeciency is high, is suitable for large-scale production.
In the present invention, content is subjected to fusion-crystallization in 95% to 98% first product guaiacol first, passes through fused junction
Crystalline substance can obtain mass percent >=99.5%；Simultaneously by fusion-crystallization by the impurity enriched in first product guaiacol to crystallize
In mother liquor.The higher crystalline mother solution of guaiacol purity continues through fusion-crystallization and purified, when guaiacol purity exists
It is no longer appropriate for carrying out fusion-crystallization when less than 90%.The mother liquor for being no longer appropriate for carrying out fusion-crystallization is contained guaiacol by rectifying
Amount is improved and crystallized again to more than 90%, while 1,2-dimethoxy benzene, 6- methyl guaiacol and 4s and 3- methyl guaiacol and 4s are existed
Tower reactor is enriched with.1,2-dimethoxy benzene, 6- methyl guaiacol and 4s and the rectifying again of 3- methyl guaiacol and 4s component of tower reactor enrichment,
1,2-dimethoxy benzene that can be higher from overhead collection to purity.1,2-dimethoxy benzene by enrichment, will through being stripped with alkali lye
The various guaiacol of phenolic hydroxy group wash aqueous phase, and the organic phase that separation is obtained is 1,2-dimethoxy benzene sterling.
Technical scheme is specifically described as follows.
The present invention provides a kind of purification process of the guaiacol first product synthesized for catechol with methanol oxidation, described
In guaiacol first product, the content of guaiacol is between 95~98wt%, and impurity includes 1,2-dimethoxy benzene, 6- methyl guaiaci lignum
Phenol and 3- methyl guaiacol and 4s, wherein single contaminant content is between 0.2~3.0wt%, using fusion-crystallization-rectifying-back extraction
Coupling technique is taken to carry out isolating and purifying acquisition guaiacol sterling, while obtaining 1,2-dimethoxy benzene accessory substance；Comprise the following steps that：
(1) crystallizer for having added guaiacol first product is rapidly heated to 28 DEG C~40 DEG C, makes guaiacol first product complete
Fully dissolved, then slow cooling is cooled down to 5~15 DEG C by chuck, keep after 5~20h, filter out uncrystallized mother liquor；
(2) after mother liquor discharge, crystal temperature effect slowly is raised to 22~26 DEG C by controlling jacket temperature, and holding 30~
60min, makes crystal block section melt sweating, filters out sweating liquid in different temperature points, and collected respectively as mother liquor by purity；
(3) crystallizer is rapidly heated to 28 DEG C~40 DEG C, is completely dissolved crystal, that is, obtain purity more than 99.5wt%
Guaiacol, the content of wherein 6- methyl guaiacol and 4s and 3- methyl guaiacol and 4s is respectively less than 0.05wt%；
(4) mother liquor filtered out in step (1) crystallization process, step (2) sweating effort is merged by content phase approximately principle, is contained
Component of the amount more than 90wt% is returned again to step (1) after being mixed with guaiacol first product and is continuing with as crystallization raw material；
(5) when in the mother liquor that crystallization process, sweating effort are filtrated to get Determination of Guaiacol be no longer appropriate for less than 90wt%
The component directly purified with fused junction crystallization, merge collect after carry out rectification under vacuum, from rectifying column tower top collect purity >=
95wt% guaiacol cut, the guaiacol cut is back to step (1) and is continuing with as crystallization raw material；
(6) tower reactor kettle liquid obtained by step (5) rectification under vacuum is collected and merged, rectification under vacuum is carried out again, is first received from tower top
The front-end volatiles that collection Determination of Guaiacol exceedes 5wt% are back to step (5) for reclaiming guaiacol, regather guaiacol and contain
Amount is incorporated as O-phthalic ether mixture less than 5wt% and O-phthalic ether content ＞ 5wt% cut to be used to reclaim adjacent benzene
Dimethyl ether；
(7) step (6) is collected to obtained O-phthalic ether mixture mass fraction for 5~15wt% aqueous slkali to enter
Row back extraction extract operation, layering obtains 1,2-dimethoxy benzene organic phase finished product and the sodium salt of methyl guaiacol and 4 containing 6- and 3- methyl is cured wound
The aqueous solution of wooden sodium phenolate.
In the present invention, in step (1) and step (3), the rate of temperature fall control of crystallization process is in 0.5~3.0 DEG C/h, heating
Speed control is in .0~5.0 DEG C/h.
In the present invention, in step (5), the condition of rectification under vacuum is as follows：Theoretical cam curve is between 10-30, distillation process
Reflux ratio be 1-3, vacuum degree control is in 10~30mmHg.
In the present invention, in step (6), the theoretical cam curve of rectifying is between 50-60, and the reflux ratio of distillation process is 3-5,
Vacuum degree control is in 10~30mmHg.
In the present invention, in step (7), alkali sodium hydroxide or sodium carbonate, the concentration of alkali lye is 5~15wt% of mass fraction
Between.
In the present invention, in step (7), alkali addition make it that aqueous pH values are more than 8 after back extraction, and organic phase is after back extraction
For 1,2-dimethoxy benzene sterling.
The present invention has advantages below compared with prior art：
1. it is used for the purifying of guaiacol, more single rectifying there is provided a kind of fusion-crystallization-rectifying-back extraction coupling technique
Process greatly reduces energy consumption, can also improve the separation yield of guaiacol.
2. isolated guaiacol purity is more than 99.5%, 6- methyl guaiacol and 4s and 3- methyl guaiacol and 4s
Content is below 0.05%, and purity meets vanillic aldehyde production requirement；By separating for several times purification, finally energy total separation yield rate exists
More than 98%.
3. in addition to it can obtain guaiacol, accessory substance 1,2-dimethoxy benzene finished product can be also obtained, and 1,2-dimethoxy benzene purity can
To reach more than 98%.
Brief description of the drawings
Fig. 1 is catechol method synthesizing guaiacol reaction equation.
Reaction equation when Fig. 2 is guaiacol and impurity synthesis of vanillin.
Fig. 3 is first product guaiacol Typical gas chromatograph figure after recovery catechol.
Fig. 4 is fusion-crystallization guaiacol Typical gas chromatograph figure after purification.
Embodiment
The present invention is described in further detail with reference to embodiment, but the present invention is not limited to following embodiments.
Embodiment 1：Fusion-crystallization
Taking a certain amount of first product guaiacol, (mass content of main matter is：Guaiacol 97.73%, 6- methyl are cured
The wooden phenol 0.64% of wound, 1,2-dimethoxy benzene 1.29%, 3- methyl guaiacol and 4s 0.29%) it is placed in the crystallizer with glass jacket.
It can be passed through between the diameter of inner pipe 50mm of crystallizer, high 230mm, outer tube diameter 65mm, high 200mm, inner and outer pipes and water is heated or cooled
Carry out temperature control.Crystallizer is warming up into 28 DEG C to be completely dissolved with up to crystal, then cooled with 1.0 DEG C/h rate of temperature fall
To 15 DEG C, 20h is incubated.Open crystalliser feet valve and release uncrystallized mother liquor, mother liquor is enriched with guaiacol as rectifying
Raw material.Sweating is carried out by chuck slow heating heating again, heating rate is 1.0 DEG C/h, is warming up to 26 DEG C, be incubated 60min, hair
Sweat terminates, and releases sweat, collects sweating liquid, and being mixed with raw material can use as crystallization raw material.By crystallizer be rapidly heated to
More than 28 DEG C, melt crystal and obtain colourless transparent liquid, one way crystallization yield is 70.5%.After gas chromatographic analysis, production
Guaiacol purity is 99.97% in product, and single contaminant content is respectively less than 0.05%.Fig. 3 is to reclaim first product after catechol to be cured
The wooden phenol Typical gas chromatograph figure of wound.Fig. 4 is fusion-crystallization guaiacol Typical gas chromatograph figure after purification.
Embodiment 2：Fusion-crystallization
Taking a certain amount of first product guaiacol, (mass content of main matter is：Guaiacol 97.93%, 6- methyl are cured
The wooden phenol 0.54% of wound, 1,2-dimethoxy benzene 1.02%, 3- methyl guaiacol and 4s 0.44%) it is placed in the identical glass clamp noose of example 1
In brilliant device, crystallizer is warming up to 28 DEG C and is completely dissolved with up to crystal, then 15 are cooled to 2.0 DEG C/h rate of temperature fall
DEG C, it is incubated 10h.Open crystalliser feet valve and release uncrystallized mother liquor, mother liquor can be enriched with the original of guaiacol as rectifying
Material.Sweating is carried out by chuck slow heating heating again, heating rate is 1.0 DEG C/h, is warming up to 26 DEG C, is incubated 60min, sweating
Terminate, release sweat, collect sweating liquid, crystallization raw material can be used as.Crystallizer is rapidly heated to more than 28 DEG C, melts crystal
Change obtains colourless transparent liquid, and one way crystallization yield is 72.1%.After gas chromatographic analysis, guaiacol purity is in product
99.92%, single contaminant content is respectively less than 0.05%.
Embodiment 3：Fusion-crystallization
Taking a certain amount of first product guaiacol, (mass content of main matter is：Guaiacol 95.23%, 6- methyl are cured
The wooden phenol 1.19% of wound, 1,2-dimethoxy benzene 1.36%, 3- methyl guaiacol and 4s 0.69%) it is placed in the identical glass clamp noose of example 1
In brilliant device, crystallizer is warming up to 28 DEG C and is completely dissolved with up to crystal, then 5 DEG C are cooled to 3.0 DEG C/h rate of temperature fall,
It is incubated 10h.Open crystalliser feet valve and release uncrystallized mother liquor, mother liquor can be enriched with the raw material of guaiacol as rectifying.
Sweating is carried out by chuck slow heating heating again, heating rate is 3.0 DEG C/h, is warming up to 24 DEG C, is incubated 30min, sweating knot
Beam, releases sweat, collects sweating liquid, and the raw material of guaiacol can be enriched with as rectifying.Crystallizer is rapidly heated to 28 DEG C
More than, melt crystal and obtain colourless transparent liquid, one way crystallization yield is 68.8%.After gas chromatographic analysis, in product
Guaiacol purity is 99.88%, and single contaminant content is respectively less than 0.05%.
Embodiment 4：Rectification under vacuum
Main matter in rectification under vacuum experiment, the product is carried out by raw material of the mother liquor of the fusion-crystallization of embodiment 1 collection
Mass content is：Guaiacol 87.79%, 6- methyl guaiacol and 4s 3.82%, 1,2-dimethoxy benzene 4.79%, 3- methyl guaiaci lignum
Phenol 1.70%.Above-mentioned product 1000g is taken in three-necked flask, rectifying, rectifying are carried out in theoretical cam curve is 10 rectifying column
Pressure process is about 10mmHg, and reflux ratio is 3：1.It is final to collect overhead fraction 832.4g, it is main in the cut of collection through analyzing
The content of material is：Guaiacol 95.87%, 6- methyl guaiacol and 4s 0.61%, 1,2-dimethoxy benzene 0.84%, 3- methyl are cured wound
Wooden phenol 1.27%, can be used as crystallizing raw material.Tower bottom distillate can be obtained simultaneously, the content of main matter is：Guaiacol 49.87%,
6- methyl guaiacol and 4s 11.61%, 1,2-dimethoxy benzene 23.22%, 3- methyl guaiacol and 4s 12.02%, can be used as rectifying again
Enrichment 1,2-dimethoxy benzene raw material.
Embodiment 5：Rectification under vacuum
Main matter in rectification under vacuum experiment, the product is carried out by raw material of the mother liquor of the fusion-crystallization of embodiment 2 collection
Mass content is：Guaiacol 86.42%, 6- methyl guaiacol and 4s 3.62%, 1,2-dimethoxy benzene 5.95%, 3- methyl guaiaci lignum
Phenol 2.50%.Above-mentioned product 1000g is taken in three-necked flask, rectifying, rectifying are carried out in theoretical cam curve is 30 rectifying column
Pressure process is about 20mmHg, and reflux ratio is 1：1.It is final to collect overhead fraction 824.4g, it is main in the cut of collection through analyzing
The content of material is：Guaiacol 97.01%, 6- methyl guaiacol and 4s 0.58%, 1,2-dimethoxy benzene 0.92%, 3- methyl are cured wound
Wooden phenol 0.87%, can be used as crystallizing raw material.Tower bottom distillate can be obtained simultaneously, the content of main matter is：Guaiacol 34.03%,
6- methyl guaiacol and 4s 20.11%, 1,2-dimethoxy benzene 32.72%, 3- methyl guaiacol and 4s 12.98%, can be used as rectifying again
Enrichment 1,2-dimethoxy benzene raw material.
Embodiment 6：Rectification under vacuum
Main matter in rectification under vacuum experiment, the product is carried out by raw material of the mother liquor of the fusion-crystallization of embodiment 3 collection
Mass content is：Guaiacol 89.17%, 6- methyl guaiacol and 4s 2.38%, 1,2-dimethoxy benzene 5.12%, 3- methyl guaiaci lignum
Phenol 2.34%.Above-mentioned product 1000g is taken in three-necked flask, rectifying, rectifying are carried out in theoretical cam curve is 30 rectifying column
Pressure process is about 30mmHg, and reflux ratio is 2：1.It is final to collect overhead fraction 846.9g, it is main in the cut of collection through analyzing
The content of material is：Guaiacol 97.23%, 6- methyl guaiacol and 4s 1.75%, 1,2-dimethoxy benzene 1.04%, 3- methyl are cured wound
Wooden phenol 0.73%, can be used as crystallizing raw material.Tower bottom distillate can be obtained simultaneously, the content of main matter is：Guaiacol 36.42%,
6- methyl guaiacol and 4s 19.24%, 1,2-dimethoxy benzene 31.52%, 3- methyl guaiacol and 4s 11.65%, can be used as rectifying again
Enrichment 1,2-dimethoxy benzene raw material.
Embodiment 7：Rectification under vacuum
1000 grams of the bottom of towe mother liquor being enriched with example 4-6 is that raw material carries out main matter in rectification under vacuum experiment, the product
Mass content be guaiacol 42.43%, 6- methyl guaiacol and 4s 17.56%, 1,2-dimethoxy benzene 27.43%, 3- methyl be cured
The wooden phenol 13.23% of wound：Above-mentioned product 1000g is taken in three-necked flask, rectifying is carried out in theoretical cam curve is 50 rectifying column,
Distillation process pressure is 20mmHg, reflux ratio 5:1.First collecting cut of the recovery Determination of Guaiacol more than 5% can be with fused junction
Brilliant mother liquor is incorporated as the raw material of enriching and recovering guaiacol, regathers the midbarrel containing 1,2-dimethoxy benzene, until adjacent benzene two
Stop collecting midbarrel when methyl ether content is less than 5%, it is final to collect midbarrel 285g, it is main in the cut of collection through analyzing
The content for wanting material is：Guaiacol 2.05%, 6- methyl guaiacol and 4s 9.55%, 1,2-dimethoxy benzene 81.46%, 3- methyl are cured
The wooden phenol 5.91% of wound.
Embodiment 8：Back extraction is handled
100 grams of O-phthalic ether mixture obtained by the rectifying of Example 7, is added in 500 milliliters of there-necked flasks, under stirring
5% sodium hydroxide solution to aqueous pH values are added dropwise and reach 8.5.Mixed liquor is transferred in 500 milliliters of separatory funnels and is layered,
Organic phase is collected as 81.2 grams of 1,2-dimethoxy benzene finished product, its purity is 98.49% through gas phase analysis.
Embodiment 9：Back extraction is handled
100 grams of O-phthalic ether mixture obtained by the rectifying of Example 7, is added in 500 milliliters of there-necked flasks, under stirring
10% sodium hydroxide solution to aqueous pH values are added dropwise and reach 8.0.Mixed liquor is transferred in 500 milliliters of separatory funnels and divided
Layer, collects organic phase as 81.3 grams of 1,2-dimethoxy benzene finished product, its purity is 98.01% through gas phase analysis.
Claims (6)
1. a kind of purification process of the guaiacol first product synthesized for catechol with methanol oxidation, the guaiacol first product
In, the content of guaiacol is between 95~98wt%；Impurity is cured including 1,2-dimethoxy benzene, 6- methyl guaiacol and 4s and 3- methyl
The wooden phenol of wound, wherein single contaminant content is between 0.2~3.0wt%, it is characterised in that use fusion-crystallization-rectifying-back extraction
Coupling technique carries out isolating and purifying acquisition guaiacol sterling, while obtaining 1,2-dimethoxy benzene accessory substance；Comprise the following steps that：
(1) crystallizer for having added guaiacol first product is rapidly heated to 28 DEG C~40 DEG C, makes guaiacol first product completely molten
Solution, then slow cooling is cooled down to 5~15 DEG C by chuck, keep after 5~20h, filter out uncrystallized mother liquor；
(2) after mother liquor discharge, crystal temperature effect slowly is raised to 22~26 DEG C by controlling jacket temperature, and holding 30~
60min, makes crystal block section melt sweating, filters out sweating liquid in different temperature points, and collected respectively as mother liquor by purity；
(3) crystallizer is rapidly heated to 28 DEG C~40 DEG C, is completely dissolved crystal, that is, obtain purity being cured more than 99.5wt%
The wooden phenol of wound, the content of wherein 6- methyl guaiacol and 4s and 3- methyl guaiacol and 4s is respectively less than 0.05wt%；
(4) mother liquor filtered out in step (1) crystallization process, step (2) sweating effort is merged by content phase approximately principle, and content surpasses
Cross 90wt% component mixed with guaiacol first product after return again to step (1) as crystallization raw material be continuing with；
(5) when in the mother liquor that crystallization process, sweating effort are filtrated to get Determination of Guaiacol be no longer appropriate for directly less than 90wt%
The component purified with fused junction crystallization, merges and carries out rectification under vacuum after collecting, collect purity >=95wt%'s from rectifying column tower top
Guaiacol cut, the guaiacol cut is back to step (1) and is continuing with as crystallization raw material；
(6) tower reactor kettle liquid obtained by step (5) rectification under vacuum is collected and merged, rectification under vacuum is carried out again, is first collected more from tower top
The front-end volatiles that the wooden phenol content of wound exceedes 5wt%, which are back to step (5), to be used to reclaim guaiacol, regathers Determination of Guaiacol small
Being incorporated as O-phthalic ether mixture in 5wt% and O-phthalic ether content ＞ 5wt% cut is used to reclaim O-phthalic
Ether；
(7) step (6) is collected to obtained O-phthalic ether mixture to be carried out instead for 5~15wt% aqueous slkali with mass fraction
Extracting operation, layering obtains 1,2-dimethoxy benzene organic phase finished product and the sodium salt of methyl guaiacol and 4 containing 6- and 3- methyl guaiacol and 4s
The aqueous solution of sodium salt.
2. purification process according to claim 1, it is characterised in that：In step (1) and step (3), in knot crystallization process
Rate of temperature fall control between 0.5~3.0 DEG C/h, heating rate control between 1.0~5.0 DEG C/h.
3. purification process according to claim 1, it is characterised in that：In step (5), the condition of rectification under vacuum is as follows：Reason
By the number of plates between 10-30, the reflux ratio of distillation process is 1-3, and vacuum degree control is in 10~30mmHg.
4. purification process according to claim 1, it is characterised in that：In step (6), the theoretical cam curve of rectifying is in 50-
Between 60, the reflux ratio of distillation process is 3-5, and vacuum degree control is in 10~30mmHg.
5. purification process according to claim 1, it is characterised in that：In step (7), alkali sodium hydroxide or sodium carbonate,
The concentration of alkali lye is between 5~15wt% of mass fraction.
6. purification process according to claim 1, it is characterised in that：In step (7), alkali addition causes water after back extraction
Phase pH value is more than 8, and organic phase is 1,2-dimethoxy benzene sterling after back extraction.
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| CN110642680A (en) * | 2019-09-19 | 2020-01-03 | 天津大学 | Crystallization separation method for preparing high-purity o-cresol |
| CN110944968A (en) * | 2019-10-29 | 2020-03-31 | 上海应用技术大学 | Method for recovering catechol from o-ethoxyphenol reaction liquid |
| CN111499499A (en) * | 2020-04-03 | 2020-08-07 | 上海艾麟化工技术服务中心 | Purification method and purification system of natural guaiacol |
| CN114181043A (en) * | 2021-12-09 | 2022-03-15 | 上海试四化学品有限公司 | Method for treating wastewater containing sodium methyl sulfate |
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| CN114181043A (en) * | 2021-12-09 | 2022-03-15 | 上海试四化学品有限公司 | Method for treating wastewater containing sodium methyl sulfate |
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