CN106478385B - A method of preparing the high-purity propylene glycol phenylate or ethylene glycol phenyl ether of Determination of Trace Phenol - Google Patents
A method of preparing the high-purity propylene glycol phenylate or ethylene glycol phenyl ether of Determination of Trace Phenol Download PDFInfo
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- CN106478385B CN106478385B CN201510555441.2A CN201510555441A CN106478385B CN 106478385 B CN106478385 B CN 106478385B CN 201510555441 A CN201510555441 A CN 201510555441A CN 106478385 B CN106478385 B CN 106478385B
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- phenol
- phenylate
- phenyl ether
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/44—Separation; Purification; Stabilisation; Use of additives by treatments giving rise to a chemical modification
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Abstract
The invention discloses a kind of methods of high-purity propylene glycol phenylate or ethylene glycol phenyl ether for preparing Determination of Trace Phenol, comprising the following steps: 1) propylene oxide or ethylene oxide and phenol is catalyzed and synthesized phenylate, are then distilled to recover excessive phenol, obtain crude product；2) inorganic base is added into above-mentioned resulting crude product, heating is sufficiently stirred；3) rectifying after removing low-boiling water, continues the product boiling point distillation that heats up, obtains Determination of Trace Phenol propylene glycol phenylate or phenol ethylene glycol phenyl ether；Using the phenolic hydroxyl group in phenol can with the alkali neutralization in inorganic base is at salt and characteristic that crude product is not volatile, phenol in crude product and inorganic base reaction are generated into the very poor sodium phenate of volatility, then remaining phenol, 30~90ppm of final products phenol content are removed through rectifying；Meanwhile the reducing component in inorganic base can remove trace oxygen compound (dissolved oxygen etc.), make that product appearance is good, extended shelf-life.This method is easy to operate, at low cost, and effect is obvious.
Description
Technical field
The invention belongs to chemical fields, and in particular to a kind of high-purity propylene glycol phenylate for preparing Determination of Trace Phenol or ethylene glycol phenyl
The method of ether.
Background technique
Propylene glycol phenylate is one of representative compound of phenylate, 242.7 DEG C of boiling point, relative density 1.063 (20/4 DEG C),
Relative molecular weight 152.19.Propylene glycol phenylate is the intermediate of phenoxybenzamine (phenoxybenzamine)；It is also that excellent higher boiling is organic molten
Agent or modified additive substitute toxicity or the biggish isophorone of smell, cyclohexanone, DBE, benzyl alcohol, ethylene glycol phenyl ether series.Cause
It is non-toxic, and compatibility is good, and rate of volatilization is moderate, excellent coalescence and coupling ability, lower surface tension, and is widely used in
Automobile and automobile repairing paint, electrophoretic coating, industrial baking vanish and ship, container, woodwork coating.
Ethylene glycol phenyl ether is also one of representative compound of phenylate, and 244.8 DEG C of boiling point, relative density 1.110 (20/4
DEG C), relative molecular weight 138.17.The efficient coalescing agent of ethylene glycol phenyl ether, film forming efficiency reach U.S. DOWANOL PPH (the third two
Alcohol phenylate) and EASTMAN KODAK company TEXANOL (alcohol ester -12) level, due to its excellent overall characteristic, early in
Just EPH is widely used to acrylic resin, NC Nitroncellulose, cellulose acetate, ethyl by American-European numerous enterprises in the seventies
Cellulose, epoxy resin, alkyd resin, the various resins such as phenoxy resin have fabulous dissolubility, it was demonstrated that ethylene glycol phenyl ether
It can make the solvent of acrylic resin, NC Nitroncellulose, cellulose acetate, ethyl cellulose, epoxy resin, phenoxy resin etc.,
It is the ideal solvent of hydroxybenzoic acid esters.In addition, and one of primary raw material in modern daily use chemicals industry.
Propylene glycol phenylate is catalyzed and synthesized by phenol or ethylene glycol phenyl ether by phenol and propylene oxide, under normal circumstances phenol mistake
5% or more amount, utilization is recovered by distillation in excessive phenol；And product then steams, 1000~5000ppm containing phenol.It is higher
The phenol of content may cause EHS problem, so that the use of propylene glycol phenylate or ethylene glycol phenyl ether is limited, especially in cosmetics
Deng and closely related industry of living.
Summary of the invention
The present invention is in order to solve the above technical problems, big portion can effectively be removed by inorganic alkali process, rectifying by providing one kind
Divide remaining phenol, thus the method for obtaining the high-purity propylene glycol phenylate of Trace Benzene or ethylene glycol phenyl ether.
The purpose of the present invention is what is be achieved through the following technical solutions: a kind of high-purity propylene glycol phenylate preparing Determination of Trace Phenol
Or the method for ethylene glycol phenyl ether, comprising the following steps:
1) propylene oxide or ethylene oxide and phenol are catalyzed and synthesized into phenylate, is then distilled to recover excessive phenol, obtained
Crude product；
2) inorganic base is added into above-mentioned resulting crude product, heating is sufficiently stirred；
3) rectifying, after removing low-boiling water, continue heat up product boiling point distillation, obtain Determination of Trace Phenol propylene glycol phenylate or
Phenol ethylene glycol phenyl ether.
The inorganic base in the step 2) is in potassium hydroxide, sodium hydroxide or potassium carbonate as a preferred technical solution,
One or any of several and zinc powder form.
As a preferred technical solution, relative to phenol in the crude product in the step 2), alkali is 200%~400%
Equivalent, and zinc powder last phase is for 100% equivalent of phenol in the crude product.
Phenol content is 1000~5000ppm in the crude product as a preferred technical solution,.
The step 2) is stirred 0.5~1 hour under conditions of 100~110 DEG C as a preferred technical solution, benzene
Phenol generates sodium phenate, and removes trace oxygen compound.
Contain trace in the propylene glycol phenylate or ethylene glycol phenyl ether product that the step 3) obtains as a preferred technical solution,
Measure 30~90ppm of phenol.
Step 3) the distillation residual liquid is containing sodium phenate and a small amount of propylene glycol phenylate or second two as a preferred technical solution,
Alcohol phenylate can be used as the raw material of synthesizing propanediol phenylate or ethylene glycol phenyl ether after processing again.
By adopting the above-described technical solution, a kind of high-purity propylene glycol phenylate for preparing Determination of Trace Phenol or ethylene glycol phenyl ether
Method, comprising the following steps: 1) propylene oxide or ethylene oxide and phenol are catalyzed and synthesized into phenylate, are then distilled to recover excessive
Phenol obtains crude product；2) inorganic base is added into above-mentioned resulting crude product, heating is sufficiently stirred；3) rectifying removes low-boiling
After water, continues the product boiling point distillation that heats up, obtain Determination of Trace Phenol propylene glycol phenylate or phenol ethylene glycol phenyl ether；Using in phenol
Phenolic hydroxyl group can with the alkali neutralization in inorganic base is at salt and characteristic that crude product is not volatile, phenol in crude product and inorganic base are reacted
The very poor sodium phenate of volatility is generated, then removes remaining phenol, 30~90ppm of final products phenol content through rectifying；Meanwhile
Reducing component in inorganic base can remove trace oxygen compound (dissolved oxygen etc.), make that product appearance is good, extended shelf-life.This method
Easy to operate, at low cost, effect is obvious, its scope of application is made to be extended to cosmetic industry, the industrial grade of raising and itself
Added value.
Specific embodiment
The present invention will be further described below with reference to examples, but protection scope of the present invention is not limited solely to implement
Example.
A method of preparing the high-purity propylene glycol phenylate or ethylene glycol phenyl ether of Determination of Trace Phenol, comprising the following steps:
1) propylene oxide or ethylene oxide and phenol are catalyzed and synthesized into phenylate, is then distilled to recover excessive phenol, obtained
Crude product；
2) inorganic base is added into above-mentioned resulting crude product, heating is sufficiently stirred；
3) rectifying, after removing low-boiling water, continue heat up product boiling point distillation, obtain Determination of Trace Phenol propylene glycol phenylate or
Phenol ethylene glycol phenyl ether.
Inorganic base in the step 2) is one of potassium hydroxide, sodium hydroxide or potassium carbonate or any several and zinc
Powder composition.
Relative to phenol in the crude product in the step 2), alkali is 200%~400% equivalent, and zinc powder last phase pair
100% equivalent of phenol in the crude product.
Phenol content is 1000~5000ppm in the crude product.
The step 2) is stirred 0.5~1 hour under conditions of 100~110 DEG C, and phenol generates sodium phenate, and removes
Trace oxygen compound.
Contain 30~90ppm of Determination of Trace Phenol in the propylene glycol phenylate or ethylene glycol phenyl ether product that the step 3) obtains.
Step 3) the distillation residual liquid after processing can containing sodium phenate and a small amount of propylene glycol phenylate or ethylene glycol phenyl ether
It is used as the raw material of synthesizing propanediol phenylate or ethylene glycol phenyl ether again.
Using the phenolic hydroxyl group in phenol can with the alkali neutralization in inorganic base is at salt and characteristic that crude product is not volatile, will be thick
Phenol and inorganic base reaction generate the very poor sodium phenate of volatility in product, then remove remaining phenol, final products benzene through rectifying
30~90ppm of phenol content；Meanwhile the reducing component in inorganic base can remove trace oxygen compound (dissolved oxygen etc.), make outside product
It sees, extended shelf-life.This method is easy to operate, at low cost, and effect is obvious, its scope of application is made to be extended to cosmetic industry,
The added value of the industrial grade of raising and itself.
Example 1: propylene glycol phenylate solid mixes caustic processes
1) thick propylene glycol phenylate 600g, content 98%, 4000ppm containing phenol are equivalent to 0.0255 equivalent and 1000ml burning are added
In bottle；Compound 2.75 equivalent of alkali is added, compound alkali is specially that NaOH2.34g (0.0583 equivalent), KOH 0.21g are equivalent to
0.00374 equivalent and zinc powder 1.7g are equivalent to 0.0225 equivalent.
2) 100 DEG C are heated to, is stirred 1 hour.
3) heating distillation, removes moisture removal；Reheating is warming up to finished product and distillates.
4) colourless transparent liquid, phenol content 72ppm are obtained；Product content 99.4%；The one-off rate of recovery 76%.
Example 2: propylene glycol phenylate lye method
1) thick propylene glycol phenylate 600g, content 98%, 4000ppm containing phenol are equivalent to 0.0255 equivalent and 1000ml burning are added
In bottle；Addition sodium hydroxide 2.5g is equivalent to 0.0668 equivalent and zinc powder 1.7g is equivalent to 0.0225 equivalent.
2) 105 DEG C are heated to, 2Hr is stirred.
3) heating distillation, removes moisture removal；Finished product is warming up to distillate.
4) colourless transparent liquid, phenol content 85ppm are obtained；Product content 99.1%；The one-off rate of recovery 69%.
Example 3: ethylene glycol phenyl ether solid mixes caustic processes
1) thick ethylene glycol phenyl ether 600g, content 98%, 4000ppm containing phenol are equivalent to 0.0255 equivalent and 1000ml burning are added
In bottle；Compound 2.75 equivalent of alkali is added, specially NaOH2.34g is equivalent to 0.0583 equivalent, KOH 0.21g is equivalent to
0.00374 equivalent and zinc powder 1.7g are equivalent to 0.0225 equivalent.
2) 110 DEG C are heated to, is stirred 1 hour.
3) heating distillation, removes moisture removal；Finished product is warming up to distillate.
4) colourless transparent liquid, phenol content 57ppm are obtained；Product content 99.5%；The one-off rate of recovery 74.5%.
Example 4: a method of preparing the high-purity propylene glycol phenylate or ethylene glycol phenyl ether of Determination of Trace Phenol, including following step
It is rapid:
1) propylene oxide or ethylene oxide and phenol are catalyzed and synthesized into phenylate, is then distilled to recover excessive phenol, obtained
Crude product；
2) inorganic base is added into above-mentioned resulting crude product, is stirred 1 hour at 100 DEG C；
3) rectifying, after removing low-boiling water, continue heat up product boiling point distillation, obtain Determination of Trace Phenol propylene glycol phenylate or
Phenol ethylene glycol phenyl ether.
Inorganic base in the step 2) is one of potassium hydroxide, sodium hydroxide or potassium carbonate or any several and zinc
Powder composition.
Relative to phenol in the crude product in the step 2), alkali is 200%% equivalent, and zinc powder last phase is for described
100% equivalent of phenol in crude product.
Phenol content is 1000ppm in the crude product.
The step 2) is sufficiently stirred under conditions of 100 DEG C, and phenol generates sodium phenate, and removes trace oxygen compound.
Contain Determination of Trace Phenol 30ppm in the propylene glycol phenylate or ethylene glycol phenyl ether product that the step 3) obtains.
Step 3) the distillation residual liquid after processing can containing sodium phenate and a small amount of propylene glycol phenylate or ethylene glycol phenyl ether
It is used as the raw material of synthesizing propanediol phenylate or ethylene glycol phenyl ether again.
Example 5: a method of preparing the high-purity propylene glycol phenylate or ethylene glycol phenyl ether of Determination of Trace Phenol, including following step
It is rapid:
1) propylene oxide or ethylene oxide and phenol are catalyzed and synthesized into phenylate, is then distilled to recover excessive phenol, obtained
Crude product；
2) inorganic base is added into above-mentioned resulting crude product, is stirred 0.8 hour at 105 DEG C；
3) rectifying, after removing low-boiling water, continue heat up product boiling point distillation, obtain Determination of Trace Phenol propylene glycol phenylate or
Phenol ethylene glycol phenyl ether.
Inorganic base in the step 2) is one of potassium hydroxide, sodium hydroxide or potassium carbonate or any several and zinc
Powder composition.
Relative to phenol in the crude product in the step 2), alkali is 400% equivalent, and zinc powder last phase is for described thick
100% equivalent of phenol in product.
Phenol content is 5000ppm in the crude product.
The step 2) is sufficiently stirred under conditions of 110 DEG C, and phenol generates sodium phenate, and removes trace oxygen compound.
Contain Determination of Trace Phenol 90ppm in the propylene glycol phenylate or ethylene glycol phenyl ether product that the step 3) obtains.
Step 3) the distillation residual liquid after processing can containing sodium phenate and a small amount of propylene glycol phenylate or ethylene glycol phenyl ether
It is used as the raw material of synthesizing propanediol phenylate or ethylene glycol phenyl ether again.
Example 6: a method of preparing the high-purity propylene glycol phenylate or ethylene glycol phenyl ether of Determination of Trace Phenol, including following step
It is rapid:
1) propylene oxide or ethylene oxide and phenol are catalyzed and synthesized into phenylate, is then distilled to recover excessive phenol, obtained
Crude product；
2) inorganic base is added into above-mentioned resulting crude product, is stirred 0.5 hour at 110 DEG C；
3) rectifying, after removing low-boiling water, continue heat up product boiling point distillation, obtain Determination of Trace Phenol propylene glycol phenylate or
Phenol ethylene glycol phenyl ether.
Inorganic base in the step 2) is one of potassium hydroxide, sodium hydroxide or potassium carbonate or any several and zinc
Powder composition.
Relative to phenol in the crude product in the step 2), alkali is 300% equivalent, and zinc powder last phase is for described thick
100% equivalent of phenol in product.
Phenol content is 3000ppm in the crude product.
The step 2) is sufficiently stirred under conditions of 105 DEG C, and phenol generates sodium phenate, and removes trace oxygen compound.
Contain Determination of Trace Phenol 60ppm in the propylene glycol phenylate or ethylene glycol phenyl ether product that the step 3) obtains.
Step 3) the distillation residual liquid after processing can containing sodium phenate and a small amount of propylene glycol phenylate or ethylene glycol phenyl ether
It is used as the raw material of synthesizing propanediol phenylate or ethylene glycol phenyl ether again.
Finally, it should be noted that above embodiments are only to illustrate the present invention and not limit technology described in the invention
Scheme；Therefore, although this specification is referring to above-mentioned each embodiment, the present invention has been described in detail, this
Field it is to be appreciated by one skilled in the art that still can modify to the present invention or equivalent replacement；And all do not depart from this
The technical solution and its improvement of the spirit and scope of invention, should all cover within the scope of the claims of the present invention.
Claims (2)
1. a kind of method of propylene glycol phenylate for preparing Determination of Trace Phenol or ethylene glycol phenyl ether, comprising the following steps:
1) propylene oxide or ethylene oxide and phenol are catalyzed and synthesized into phenylate, is then distilled to recover excessive phenol, obtain crude product；
2) inorganic base is added into above-mentioned resulting crude product, heating is sufficiently stirred；Under conditions of 100~110 DEG C stirring 0.5~
1 hour, phenol generated phenolate, and removes trace oxygen compound；Relative to phenol in the crude product, base excess 200%~400%
Equivalent, and zinc powder last phase is for 100% equivalent of phenol in the crude product；Inorganic base in the step 2) is hydroxide
One of potassium, sodium hydroxide or potassium carbonate or any several and zinc powder form；
3) rectifying after removing low-boiling water, continues the product boiling point distillation that heats up, obtains the propylene glycol phenylate or second of Determination of Trace Phenol
Glycol phenylate contains 30~90ppm of Determination of Trace Phenol in the propylene glycol phenylate or ethylene glycol phenyl ether product that the step 3) obtains；Institute
Step 3) distillation residual liquid is stated containing sodium phenate and a small amount of propylene glycol phenylate or ethylene glycol phenyl ether, after processing, conjunction can be used as again
At propylene glycol phenylate or the raw material of ethylene glycol phenyl ether.
2. the method for the propylene glycol phenylate or ethylene glycol phenyl ether of preparation Determination of Trace Phenol as described in claim 1, it is characterised in that:
Phenol content is 1000~5000ppm in the crude product.
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| CN107694602B (en) | 2017-08-18 | 2019-11-12 | 佳化化学（茂名）有限公司 | A kind of synthetic method of the catalyst for preparing propylene glycol phenylate and propylene glycol phenylate |
| CN110642706B (en) * | 2019-10-08 | 2020-10-09 | 江苏东南纳米材料有限公司 | Preparation method of high-purity phenoxyethanol |
| CN111454129B (en) * | 2020-04-29 | 2023-04-11 | 浙江皇马科技股份有限公司 | Preparation method of high-purity phenoxyethanol |
| CN111718244B (en) * | 2020-07-28 | 2023-06-27 | 浙江皇马科技股份有限公司 | Preparation process of phenoxyethanol as raw material for cosmetics |
| CN113072431A (en) * | 2021-03-25 | 2021-07-06 | 浙江皇马科技股份有限公司 | High-selectivity synthesis method of propylene glycol phenyl ether |
| CN114874078B (en) * | 2022-03-29 | 2023-09-29 | 浙江皇马科技股份有限公司 | Synthesis method of propylene glycol phenyl ether with high isomer content |
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| CN101712600A (en) * | 2008-10-07 | 2010-05-26 | 抚顺佳化聚氨酯有限公司 | Method for preparing ethylene glycol phenyl ether, propylene glycol phenyl ether and butylene glycol phenyl ether |
| CN104292083A (en) * | 2014-10-11 | 2015-01-21 | 江苏常州酞青新材料科技有限公司 | Method for removing phenol in refining process of propylene glycol monophenyl ether |
| CN104326887A (en) * | 2014-10-11 | 2015-02-04 | 江苏常州酞青新材料科技有限公司 | Method for removing phenol in ethylene glycol phenyl ether refining course |
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| CN101712600A (en) * | 2008-10-07 | 2010-05-26 | 抚顺佳化聚氨酯有限公司 | Method for preparing ethylene glycol phenyl ether, propylene glycol phenyl ether and butylene glycol phenyl ether |
| CN104292083A (en) * | 2014-10-11 | 2015-01-21 | 江苏常州酞青新材料科技有限公司 | Method for removing phenol in refining process of propylene glycol monophenyl ether |
| CN104326887A (en) * | 2014-10-11 | 2015-02-04 | 江苏常州酞青新材料科技有限公司 | Method for removing phenol in ethylene glycol phenyl ether refining course |
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