CN104370696A - Novel method for separating ethylene glycol and 1,2-pentanediol - Google Patents
Novel method for separating ethylene glycol and 1,2-pentanediol Download PDFInfo
- Publication number
- CN104370696A CN104370696A CN201410558082.1A CN201410558082A CN104370696A CN 104370696 A CN104370696 A CN 104370696A CN 201410558082 A CN201410558082 A CN 201410558082A CN 104370696 A CN104370696 A CN 104370696A
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- Prior art keywords
- ethylene glycol
- entrainer
- pentanediol
- extraction
- azeotropic distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/82—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/86—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
Abstract
The invention discloses a novel method for separating ethylene glycol and 1,2-pentanediol. The separation process mainly comprises the unit operation steps of azeotropic distillation, extraction, filtration, rectification and the like. According to the method, a proper entrainer is selected, and the rectification operation condition is preliminarily determined; a mixture of ethylene glycol and 1,2-pentanediol is fed into a rectification tower together with the entrainer, an azeotrope liquid of ethylene glycol and the entrainer is obtained on the top of the tower, and a qualified 1,2-pentanediol product is obtained at the bottom of the tower; an extracting agent is insoluble in the entrainer, but is soluble with ethylene glycol, the extracting agent is added into the azeotrope liquid and cooling and filtering are carried out, so that the azeotrope liquid can be separated, the filter cake is the entrainer and can be recycled, and the filtrate is a mixture of ethylene glycol and the extracting agent; the qualified ethylene glycol product can be prepared from the filtrate by normal-pressure or reduced-pressure rectification, and the extracting agent can be reclaimed and recycled.
Description
Technical field
The present invention relates to the novel method of a kind of separating ethylene glycol and 1,2-pentanediol.The method is applicable to the separation containing polyvalent alcohol mixed solutions such as ethylene glycol and 1,2-pentanediols, belongs to the separation engineering field in chemical engineering.
Background technology
Along with global economic development, the demand of oil increases day by day, and petroleum resources reduce day by day, and contradiction between oil supply and demand increasingly sharpens.Utilizing reproducible biomass resource, Developing Biomass chemical industry, petroleum replacing Chemicals, want the energy, resource and material to biomass, is global research focus.Corn is utilized to replace petroleum resources production plant chemical industry alcohol and chemical materials to become the emphasis of scientific research.Along with Global Oil resource reduces gradually, international oil price constantly rises, and proposes corn in recent years and " substitutes " Oil Strategy.Not only cost is low to replace oil to do raw material production chemical industry alcohol with corn, and is manufacture Chemicals with renewable resources, has broad prospects.The special national conditions development Maize Production chemical industry alcohol industry of China has more advantage: corn chemical alcohol is oil replacement industry, and particularly oil supply is nervous can to alleviate China's energy; Greatly developing with corn is the petrochemical complex substitute products of raw material, as fuel alcohol, polyvalent alcohol, poly(lactic acid) etc. can alleviate the dependence to oil, reduces the import of oil, alleviates the pressure of domestic petroleum supply; Refine chemical industry alcohol with corn not only most effective, and the target of recycling economy can be realized.
This raw material derives from corn fermentation treatment solution.Containing ethylene glycol, 1,2-pentanediol etc. in this stock liquid.Ethylene glycol and 1,2-pentanediol boiling point are very near, and very difficult usual way is isolated.China's ethylene glycol product is mainly for the production of polyester (comprising trevira, vibrin and film etc.), deicing fluid and tackiness agent, paint solvent, Everlube, tensio-active agent and polyester polyol etc.1,2-pentanediol is widely used in the whole world, except as except bactericide propiconazole intermediate, is also the important source material of producing the products such as trevira, tensio-active agent, medicine.The demand of these two kinds of products is increasing year by year in recent years.Therefore, the higher ethylene glycol of value is isolated from polyol product and 1,2-pentanediol product has important economic worth and realistic meaning.
Summary of the invention
The invention reside in the novel method providing a kind of separating ethylene glycol and 1,2-pentanediol mixture to obtain ethylene glycol and 1,2-pentanediol product, mainly adopt the technological processs such as azeotropic distillation, extraction, filtration, rectifying.
The present invention is realized by this method: adopt azeotropic distillation, select suitable entrainer to come to carry out initial gross separation to ethylene glycol and 1,2-pentanediol.To azeotropic distillation, can select to be rich in entrainer backflow or entrainer and stock blend and reflux with definite composition.So reflux ratio and working pressure to affect in tower concentration of component at the bottom of liquid phase distribution and tower top, tower to a great extent to be changed.By the adjustment to azeotropic distillation reflux ratio and working pressure, desirable separating effect can be obtained.
The present invention have chosen suitable entrainer, is tentatively determined azeotrope composition, azeotropic point and the separation sequence of testing system by ASPENPLUS.Azeotropy rectification column is by following conditional operation, and under normal or reduced pressure, rectifying entrainer and mixture are sent in tower, and operating reflux ratio is 3-30, by overhead extraction ethylene glycol and the entrainer of rectifying tower, and extraction 1,2-pentanediol at the bottom of tower.Because entrainer and ethylene glycol dissolve each other define homogeneous phase solution, so also need further separation and azeotropic liquid.Add another kind of extraction agent and the two can be separated by the method for filtering.Extraction agent is insoluble to entrainer and but can dissolves each other with ethylene glycol, uses extraction agent extract and carry out the separation that filter operation can realize azeotrope.Filter cake is entrainer, and filtrate is the mixed solution of extraction agent and ethylene glycol.Filtrate can obtain qualified ethylene glycol product and recycling use entrainer and extraction agent by conventional distillation.This operation can reach good separating effect.
Idiographic flow (see accompanying drawing one, two): containing ethylene glycol-1,2-pentanediol-entrainer mixture enters in azeotropy rectification column, and tower top azeotrope is after condenser condenses, and the extraction of partial reflux part, reflux ratio is 3-30, finally obtains 1,2-pentanediol product at the bottom of tower.Overhead extraction liquid is azeotropic mixture, by adding extraction agent and making solution be separated by the method for filtering.Filtrate is the mixing solutions of ethylene glycol and extraction agent, and filter cake is entrainer.Entrainer can continue to recycle after reclaiming.Ethylene glycol after separation and the mixture of extraction agent carry out normal pressure or rectification under vacuum and operate and can realize effectively being separated of ethylene glycol and extraction agent in rectifying tower, can obtain ethylene glycol product, and extraction agent can be made to recycle.
The invention has the advantages that and adopt entrainer and ethylene glycol to form azeotrope, azeotrope and 1, the relative volatility of 2-pentanediol and boiling point differ larger, high purity 1 can be isolated at the bottom of tower, 2-pentanediol, tower top azeotrope continues through extraction, filtration and distillation operation and can obtain ethylene glycol and reclaim entrainer and extraction agent.The advantages such as the present invention has practical, and device operational stability is strong.
The inventive method, by the restriction of above-mentioned concrete device, is carried out the adjustment of technical process or conversion according to this patent, is undertaken amplifying by treatment capacity, carries out the behavior that lab scale, pilot scale and suitability for industrialized production all belong to the infringement of patent according to this patent requirement.
Accompanying drawing explanation
Fig. 1 is azeotropic distillation process flow sheet, and Fig. 2 is conventional distillation process flow sheet.
Embodiment
Example one
Adopt azeotropy rectification column and carry out periodical operation, raw material is ethylene glycol-1, and the mixture (wherein containing ethylene glycol: 1,2-pentanediol: entrainer mass ratio is 2:1:2) of 2-pentanediol-entrainer, working pressure is set to 40kpa, and reflux ratio is 15.Tower top temperature is stabilized in about 145 DEG C, and bottom temperature changes to 169 DEG C by 160 DEG C.Tower top obtains the azeotropic liquid of ethylene glycol and entrainer, reaches 99.9% by regulating reflux ratio azeotrope content.Azeotropic distillation operation obtains good separating effect, proves that the method rectifying tower can obtain azeotrope.
Example two
In employing, routine equipment and operational condition carry out continuous rectification operation, with bottom normal temperature charging in the middle part of rectifying tower.Tower top still can obtain azeotrope, and after stablizing extraction, by regulating reflux ratio, continue rectifying and make tower reactor obtain 1,2-qualified pentanediol product, purity reaches more than 98%.
Example three
Collect the tower top azeotrope of above-mentioned two examples, extract with extraction agent, and by filter operation, filtrate is the mixing solutions of ethylene glycol and extraction agent, and filter cake is entrainer.The purity finally obtaining entrainer after super-dry is 99.5%.The mixing solutions of ethylene glycol and extraction agent, be separated through common rectifying tower and obtain qualified ethylene glycol product, product purity reaches more than 98%, and being extracted agent can recycle.
Claims (6)
1. an employing azeotropic distillation and extraction filtering technique are separated corn fermentation treatment solution and obtain ethylene glycol product and 1, the novel method of 2-pentanediol product, step is as follows: polyvalent alcohol mixed solution enters in rectifying tower, the azeotropic liquid of overhead extraction ethylene glycol and entrainer, extraction purity at the bottom of tower reaches more than 98% 1,2-pentanediol product; The entrainer that azeotropic distillation column overhead obtains and ethylene glycol dissolve each other and define homogeneous phase solution, add another kind of extraction agent and the two can be separated by the method for filtering.
2. azeotropic distillation column plate number is 60-200 block, working pressure normal pressure or decompression, and tower top temperature controls at 120 ~ 160 DEG C, and bottom temperature remains on 130 ~ 255 DEG C, and operating reflux ratio is under the azeotropic distillation condition of 3-30, can obtain good azeotropic distillation separating effect.
3. extraction agent is insoluble to entrainer and but can dissolves each other with ethylene glycol, is joined by extraction agent in azeotropic liquid, and reduce temperature and also make it be separated by filter operation, filter cake is entrainer, can recycle; The filtrate that ethylene glycol and extraction agent are formed can effectively realize being separated by normal pressure or rectification under vacuum, and can obtain purity and reach more than 98% ethylene glycol product, extraction agent also can recycle.
4., according to described in claims 1, the entrainer that the processing method of azeotropic distillation separating ethylene glycol and 1,2-pentanediol mixture uses is one or more in aromatic hydrocarbons, alkane, alcohol, ether, ketone compound, and entrainer is solid-state in normal conditions.
5., according to described in claims 3, the extraction agent used is the one in benzene, methyl alcohol, ethanol, butanols, water, methyl ethyl ether, dme, sherwood oil and ketone compounds.
6. adopt azeotropic distillation and extraction filtering technique to be separated corn fermentation treatment solution according to the one described in claim 1,2,3 and obtain ethylene glycol product and 1, the novel method of 2-pentanediol product, it is characterized in that not patenting and utilizing the method to carry out lab scale, pilot scale and suitability for industrialized production all belongs to infringement act.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410558082.1A CN104370696A (en) | 2014-10-21 | 2014-10-21 | Novel method for separating ethylene glycol and 1,2-pentanediol |
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| CN201410558082.1A CN104370696A (en) | 2014-10-21 | 2014-10-21 | Novel method for separating ethylene glycol and 1,2-pentanediol |
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| CN104370696A true CN104370696A (en) | 2015-02-25 |
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| CN201410558082.1A Pending CN104370696A (en) | 2014-10-21 | 2014-10-21 | Novel method for separating ethylene glycol and 1,2-pentanediol |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105130755A (en) * | 2015-07-24 | 2015-12-09 | 常州大学 | Method of separating mixture of neopentyl glycol and ethylene glycol |
| CN110117122A (en) * | 2019-06-17 | 2019-08-13 | 武汉兴天宇环境股份有限公司 | A kind of hydroxypropyl first producing wastewater treatment |
| CN110878007A (en) * | 2018-09-05 | 2020-03-13 | 长春美禾科技发展有限公司 | Refining method of non-petroleum-based ethylene glycol |
| US11180436B2 (en) * | 2019-09-25 | 2021-11-23 | Nan Ya Plastics Corporation | Method for purifying by-product ethylene glycol of polyester in converting plasticizer |
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| JP2000239201A (en) * | 1999-02-16 | 2000-09-05 | Teijin Ltd | Recovery of dimethyl terephthalate and ethylene glycol |
| US20080275277A1 (en) * | 2006-10-27 | 2008-11-06 | Peter Kalagias | Processes for isolating or purifying propylene glycol, ethylene glycol and products produced therefrom |
| US20130284584A1 (en) * | 2012-01-10 | 2013-10-31 | Shanghai Research Institute Of Petrochemical Technology, Sinopec | Process for separating ethylene glycol and 1, 2-butanediol |
| CN103396290A (en) * | 2013-07-08 | 2013-11-20 | 吉林化工学院 | Novel process for separating ethylene glycol and 1,2-butanediol |
| CN103772148A (en) * | 2013-07-08 | 2014-05-07 | 吉林化工学院 | Novel method for separating mixture of ethylene glycol and 1, 2-butanediol by adopting azeotropic distillation and extraction coupling technologies |
-
2014
- 2014-10-21 CN CN201410558082.1A patent/CN104370696A/en active Pending
Patent Citations (5)
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| JP2000239201A (en) * | 1999-02-16 | 2000-09-05 | Teijin Ltd | Recovery of dimethyl terephthalate and ethylene glycol |
| US20080275277A1 (en) * | 2006-10-27 | 2008-11-06 | Peter Kalagias | Processes for isolating or purifying propylene glycol, ethylene glycol and products produced therefrom |
| US20130284584A1 (en) * | 2012-01-10 | 2013-10-31 | Shanghai Research Institute Of Petrochemical Technology, Sinopec | Process for separating ethylene glycol and 1, 2-butanediol |
| CN103396290A (en) * | 2013-07-08 | 2013-11-20 | 吉林化工学院 | Novel process for separating ethylene glycol and 1,2-butanediol |
| CN103772148A (en) * | 2013-07-08 | 2014-05-07 | 吉林化工学院 | Novel method for separating mixture of ethylene glycol and 1, 2-butanediol by adopting azeotropic distillation and extraction coupling technologies |
Non-Patent Citations (1)
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105130755A (en) * | 2015-07-24 | 2015-12-09 | 常州大学 | Method of separating mixture of neopentyl glycol and ethylene glycol |
| CN110878007A (en) * | 2018-09-05 | 2020-03-13 | 长春美禾科技发展有限公司 | Refining method of non-petroleum-based ethylene glycol |
| CN110878007B (en) * | 2018-09-05 | 2023-04-28 | 长春美禾科技发展有限公司 | Refining method of non-petroleum ethylene glycol |
| CN110117122A (en) * | 2019-06-17 | 2019-08-13 | 武汉兴天宇环境股份有限公司 | A kind of hydroxypropyl first producing wastewater treatment |
| US11180436B2 (en) * | 2019-09-25 | 2021-11-23 | Nan Ya Plastics Corporation | Method for purifying by-product ethylene glycol of polyester in converting plasticizer |
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Application publication date: 20150225 |