CN106146299A - Produce acetas and the method for ethylene glycol - Google Patents
Produce acetas and the method for ethylene glycol Download PDFInfo
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- CN106146299A CN106146299A CN201510172179.3A CN201510172179A CN106146299A CN 106146299 A CN106146299 A CN 106146299A CN 201510172179 A CN201510172179 A CN 201510172179A CN 106146299 A CN106146299 A CN 106146299A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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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
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
- C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
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Abstract
The present invention relates to the co-production of a kind of acetas and ethylene glycol, mainly solve existing acetas production technology generation water and form the technical problem that multiple azeotropic mixture causes flow process complexity, separating energy consumption is high.The present invention, by using under conditions of catalyst exists, adds acetic acid in single reactive distillation column middle and upper part, and bottom adds C1～C5Alcohol, oxirane, acetic acid and alcohol generation esterification generate acetas and water, the water that oxirane and esterification generate reacts coproduction ethylene glycol, reaction distillation tower top obtains acetas, tower reactor obtains ethylene glycol, diethylene glycol, triethylene glycol and Polyethylene Glycol, respectively obtain the technical scheme of the heavy constituents such as ethylene glycol product, diethylene glycol product, triethylene glycol product and Polyethylene Glycol again through rectification, preferably solve this problem, can be used for the coproduction commercial production of acetas and ethylene glycol.
Description
Technical field
The present invention relates to the co-production of a kind of acetas and ethylene glycol.
Background technology
Acetas is important organic solvent, is widely used in coating, adhesive, medicine
Deng numerous areas.Along with reinforcement and the raising of environmental consciousness of environmental requirement, acetas will be by
Gradually substitute the butanone in the product such as coating, adhesive, toluene, benzene etc. to environment and the mankind
Harmful solvent., all there is acid, alcohol, ester and water in most of esterification production technology processes
Separation problem, there is alcohol-water, alcohol-ester, ester-water binary azeotrope, alcohol-water in system
-ester ternary azeotrope, causes traditional acetate esters technological process of production, is with acid mostly
Reacting with alcohol, then experience a series of separation process, long flow path, energy consumption is high.Such as second
Acetoacetic ester is a kind of very important organic chemical industry's raw material, and industrial water requirement increases day by day.
At present, one of main method of domestic preparation ethyl acetate remains alcohol, acetic acid esterification process, especially
It is the place that ethanol production is abundant.It is pure that application response rectification method improves ethyl acetate product
Degree and reduction operating cost always were the focus of research till now from the past.Reaction is utilized to steam
Evaporate technique can break thermodynamical equilibrium limit, improve response speed and conversion ratio, simplification equipment,
Saving equipment investment, and reduction energy resource consumption ([moral] pine De Maheer, Jin Lebian. reaction is steamed
Evaporating [M]. Zhu Jianhua is translated. Beijing: Chemical Industry Press, 2005).But reaction distillation
Technique is the same with traditional handicraft all cannot eliminate water and the reactant converted the most completely and reaction
The most how the azeotropic problem of product, eliminate azeotropic problem, is to simplify the technological process of production,
Reduce the key of energy consumption.
Ethylene glycol is very important Organic Chemicals, is mainly used to produce polyester fiber
(PET), plastics, rubber, Polyester Paint, adhesive, nonionic surfactant, ethanol
Amine and explosive, be used as solvent, lubricant, plasticizer and antifreezing agent etc., wherein the most in a large number
With produce polyester have the call, increase the fastest.Conventional petroleum route uses the direct oxygen of ethylene
Changing EO processed, EO direct hydration EG, water, as nucleopilic reagent, replaces with EO
Ring-opening reaction generates EG, and production technology is mainly by SHELL, SD and DOW tri-the father-in-law
Department's monopolization.The present situation of China's glycol unit at present, hydration ethylene glycol technology path falls behind,
The selectivity of ethylene glycol is low, and device material consumption is high；Water ratio is high, complex manufacturing, long flow path,
Energy consumption is high；Small scale, the market competitiveness is the strongest.The most external advanced ethylene oxide hydration
Device, ethylene glycol yield can reach more than 99%, and the unit consumption of ethylene glycol is lower than China
10% (Zhao Lan, Li Weizhen, Gu Yanli. the present situation of ethylene oxide hydration preparing ethylene glycol, technology
Progress and suggestion [J]. chemical industry is in progress, and 2009, (S1)).
Reaction distillation produces acetas technique and has that technological process is simple, equipment investment and behaviour
Making the advantages such as expense is low, researcher just has begun to from the thirties in 20th century carry out theory
And experimentation.But in addition to methyl formate industrialization, remaining acetate esters there is not yet industry
Change reported success.Acetas production technology generates water and acetas, alcohol shape due to esterification
Multiple azeotropic mixture is become to cause the problems such as separating energy consumption is high, flow process is complicated, discharge of wastewater is many.
Producing glycol by virtue of hydration of ethylene oxide currently mainly uses tubular type or tubular reaction
Device, withdraws rapidly heat with cooling mediums such as water, makes reactor safety and stability long-term operation.
In ethylene oxide hydration reaction production ethylene glycol technique, water is as reaction raw materials, oxirane
Fast with water response speed, after producing ethylene glycol, remove from tower reactor, at reactive distillation column at once
Ethylene oxide concentration is low, and oxirane and ethylene glycol continue reaction and generates diethylene glycol and three sweet
The amount of alcohol is extremely low, for obtaining ethylene glycol high-class product, reactive distillation tower reactor liquid is carried out rectification,
Respectively obtain ethylene glycol product, diethylene glycol product, triethylene glycol product and Polyethylene Glycol etc.
Heavy constituent.Reactive distillation produces acetas reboiler to be needed to provide heat, can make full use of
The reaction heat of ethylene oxide hydration reaction, reduces reboiler, reduces equipment investment simultaneously.
Summary of the invention
The technical problem to be solved is present in tradition acetas production technology
Form multiple azeotropic mixture owing to esterification generates water with acetas, alcohol, cause separating energy consumption
The problems such as high, flow process complexity, discharge of wastewater are many, it is provided that a kind of new acetas and ethylene glycol
Co-production.The method has the advantages such as separating energy consumption is low, flow process is simple.
For solving above-mentioned technical problem, the technical solution used in the present invention is as follows: a kind of acetic acid
Ester and the co-production of ethylene glycol, under conditions of catalyst exists, acetic acid and alcohol generation ester
Changing reaction and generate acetas and water, the water that oxirane and esterification generate reacts coproduction second
Glycol, comprises the steps of
A) adding acetic acid on single reactive distillation column top, bottom adds alcohol and oxirane
Mixture；Acetic acid feed position is rectifying section to tower top, acetic acid feed position and alcohol and ring
It is that the mixture of conversion zone, alcohol and oxirane enters between the mixture feed entrance point of oxidative ethane
Material position is stripping section to tower reactor；
B) rectifying section fills filler, conversion zone catalyst filling and filler, and stripping section is filled
Filler；
C) acetic acid and alcohol generation esterification generate acetas and water, simultaneously oxirane with
The water generation hydration reaction that esterification generates generates ethylene glycol；
D) by the rectifying action of reactive distillation column, reactive distillation tower top obtains acetas and produces
Product, tower reactor obtains ethylene glycol, diethylene glycol, triethylene glycol and Polyethylene Glycol；
E) reactive distillation tower reactor liquid respectively obtains ethylene glycol product, diethylene glycol through rectification
The heavy constituents such as product, triethylene glycol product and Polyethylene Glycol.
In technique scheme, alcohol is preferably selected from C1～C5Positive structure or isomery alcohol apoplexy due to endogenous wind are extremely
Few one, more preferably at least in ethanol, isopropanol, normal propyl alcohol or n-butyl alcohol
Kind；Alcohol is preferably 1:1～1.20:1 with the mol ratio of acetic acid；Alcohol and the mol ratio of oxirane
It is preferably 1:1～1.20:1；The theoretical cam curve of reactive distillation column is preferably 45～70 pieces, tower
Top operation temperature is preferably 65～140 DEG C, and tower top operation pressure is preferably 100～150kPa,
Tower reactor operation pressure is preferably 120～180kPa, and tower reactor operation temperature is preferably 180～240
DEG C, reflux ratio is preferably 1～5；The theoretical cam curve of reactive distillation column is more preferably 50～65
Block, tower top operation temperature is more preferably 75～125 DEG C, and tower top operation pressure is more preferably
100～120kPa, tower reactor operation pressure is more preferably 130～150kPa, tower reactor operation temperature
More preferably 190～210 DEG C, reflux ratio is more preferably 2～4；Reactive distillation column conversion zone
Theoretical cam curve is preferably 10～20 pieces, and the theoretical cam curve of rectifying section is preferably 10～30
Block, the theoretical cam curve of stripping section is preferably 10～20 pieces.Ethylene glycol high-class product is from ethylene glycol
Treating column side take-off, tower top is ethylene glycol Grade A
Esterification:
R-OH+CH3COOH→CH3COOR+H2O
Hydration reaction:
Overall reaction:
Wherein: R-OH is C1～C5Alcohol, CH3COOR is C1-C5Acetic acid corresponding to alcohol
Ester, esterification is micro-endothermic reaction (ethyl acetate system reaction heat 13.02kJ/mol),
Ethylene oxide hydration reaction is strong exothermal reaction, and reaction heat is 80kJ/mol.
Table 1 is under 1atm, acetas (C4～C6) system azeotropic point temperature and composition.
Table 1
Note: * is dual azeotropic mixture.
As can be seen from Table 1, owing to esterification generates in water, the water of generation and system
Alcohol and acetic acid product ester are respectively formed azeotropic mixture, and aqueous azeotropic mixture causes and the production of acetas
Technique at least needs the rectifying column of 2, and owing to reflux ratio is big, the latent heat of vaporization of water is big, point
High from energy consumption, often produce 1mol acetas, discharge 1mol waste water.
Esterification and ethylene oxide hydration reaction are carried out the most in acid condition, reaction
Temperature and reaction pressure can well be mated.1mol alcohol and 1mol acetic acid occur esterification anti-
Should generate water and the 1mol acetas of 1mol, the water that esterification generates is anti-by hydration in time
Should consume, it is suppressed that water-alcohol, water-acetas-ol, water-acetas azeotropic mixture
Being formed, overhead is acetas product, decreases the energy consumption separating water.
Ethylene oxide hydration reaction can be regarded as irreversible exothermic reaction, at general industry
Under working condition, the conversion ratio of oxirane can be close to 100%, the heat that hydration reaction produces
Amount can be distillated process utilize, further reduce over journey energy consumption.
The ethylene glycol of by-product, diethylene glycol, triethylene glycol can be separated by follow-up rectification
Obtain.In order to ensure that the product quality of ethylene glycol can reach the requirement of top grade product.Ethylene glycol
The thick ethylene glycol product of purifying column T-102 overhead extraction, T-102 side take-off ethylene glycol is excellent
Product.
Using technical scheme, the theoretical cam curve of reactive distillation column is 50 pieces of (towers
Plate number is counted from top to bottom), tower top operation pressure is 100kPa, and tower top operation temperature is
76.8 DEG C, tower reactor operation pressure is 130kPa, and tower reactor operation temperature is 205 DEG C, reflux ratio
Being 3.5, joint production process reactive distillation column reboiler is to individually produce acetas technique again
The 30% of boiling device load.The present invention by the coupling of reaction feed mol ratio, same instead
Esterification and ethylene oxide hydration reaction in rectifying column is answered to be coupled, coproduction acetas and second
Glycol, while reducing equipment investment and process energy consumption, it is also possible to reduces the discharge of waste water
Amount, achieves preferable technique effect.
Accompanying drawing explanation
Fig. 1 is that coproduction of the present invention produces acetas and the process flow diagram of ethylene glycol.
In Fig. 1, T-101 is reactive distillation column, and 1 is acetic acid feed, and 2 is alcohol and epoxy
The mixture charging of ethane, 3 is acetas product, and 4 is the by-products such as ethylene glycol.T-102
For ethylene glycol purifying column, 5 is the thick product of ethylene glycol, and 6 is ethylene glycol product, and 7 is diethyl
Glycol, triethylene glycol mixture.T-103 is diethylene glycol purifying column, and 8 is diethylene glycol
Product, 9 is thick triethylene glycol.T-104 is that triethylene glycol proposes tower, and 10 is triethylene glycol
Product, 11 is the heavy constituents such as high-boiling components.
In Fig. 1, acetic acid feed 1 enters above reactive distillation column T-101 conversion zone, alcohol
Feed 2 with the mixture of oxirane to enter below reactive distillation column T-101 conversion zone,
Logistics 3 containing acetas distillates from tower top, and the logistics 4 containing ethylene glycol distillates from tower reactor
Rear entrance T-102, the thick product of ethylene glycol from the extraction of T-102 top, ethylene glycol product from
T-102 side take-off, thick diethylene glycol product 7 enters T-103, diethylene glycol product from
T-103 overhead extraction, thick triethylene glycol enters T-104, thing after T-103 tower reactor extraction
Stream 10 is that triethylene glycol product is adopted from T-104 tower reactor from the extraction of T-104 top, high-boiling components
Go out..
Below by embodiment, the invention will be further elaborated, but these embodiments
In no case the scope of the present invention is construed as limiting.
Detailed description of the invention
[embodiment 1]
Under conditions of catalyst exists, alcohol and the mixture of oxirane and acetic acidreaction,
Coproduction acetas and ethylene glycol, comprise the steps of
A) adding acetic acid on single reactive distillation column top, bottom adds alcohol and oxirane
Mixture；Acetic acid feed position is rectifying section to tower top, acetic acid feed position and alcohol and ring
It is that the mixture of conversion zone, alcohol and oxirane enters between the mixture feed entrance point of oxidative ethane
Material position is stripping section to tower reactor；
B) rectifying section fills filler, conversion zone catalyst filling and filler, and stripping section is filled
Filler；
C) acetic acid and alcohol generation esterification generate acetas, simultaneously oxirane and esterification
The water generation hydration reaction that reaction generates generates ethylene glycol；
D) by the rectifying action of reactive distillation column, reactive distillation column overhead obtains acetas
Product, tower reactor obtains ethylene glycol product.
The alcohol used is ethanol, wherein ethanol: acetic acid: molar ratio=1:1:1.
The theoretical cam curve of reactive distillation column is 50 pieces (number of plates is counted from top to bottom), tower
Top operation pressure is 100kPa, tower top operation temperature 72 DEG C, and tower reactor operation pressure is
130kPa, tower reactor operation temperature is 207 DEG C, and reflux ratio is 2.4.
The rectifying section theoretical cam curve of reactive distillation column is 20 pieces (the 1st～20 pieces).
The conversion zone theoretical cam curve of reactive distillation column is 20 pieces (the 21st～40 pieces).
The stripping section theoretical cam curve of reactive distillation column is 10 pieces (the 41st～50 pieces).
Ethyl acetate product distillates from tower top, and ethylene glycol product distillates from tower reactor.Tower top,
Tower reactor product quality composition is shown in Table 2.Joint production process reactive distillation column reboiler is independent
Produce the 81.4% of ethyl acetate technique reboiler.
Table 2
[embodiment 2]
Embodiment is same as in Example 1.
The alcohol used is isopropanol, wherein isopropanol: acetic acid: molar ratio
=1.18:0.94:1.
The theoretical cam curve of reactive distillation column is 55 pieces (number of plates is counted from top to bottom), tower
Top operation pressure is 105kPa, and tower top operation temperature is 85 DEG C, and tower reactor operation pressure is
135kPa, tower reactor operation temperature is 206 DEG C, and reflux ratio is 1.
The rectifying section theoretical cam curve of reactive distillation column is 25 pieces (the 1st～25 pieces).
The conversion zone theoretical cam curve of reactive distillation column is 15 pieces (the 26th～40 pieces).
The stripping section theoretical cam curve of reactive distillation column is 15 pieces (the 41st～55 pieces).
Isopropyl acetate product distillates from tower top, and ethylene glycol product distillates from tower reactor.Tower top,
Tower reactor product quality composition is shown in Table 3.Joint production process reactive distillation column reboiler is independent
Produce the 53.3% of isopropyl acetate technique reboiler.
Table 3
[embodiment 3]
Embodiment is same as in Example 1.
The alcohol used is normal propyl alcohol, wherein normal propyl alcohol: acetic acid: molar ratio
=1.1:1.1:1.
The theoretical cam curve of reactive distillation column is 55 pieces (number of plates is counted from top to bottom), tower
Top operation pressure is 110kPa, and tower top operation temperature is 91 DEG C, and tower reactor operation pressure is
140kPa, tower reactor operation temperature is 196 DEG C, and reflux ratio is 5.
The rectifying section theoretical cam curve of reactive distillation column is 25 pieces (the 1st～25 pieces).
The conversion zone theoretical cam curve of reactive distillation column is 15 pieces (the 26th～40 pieces).
The stripping section theoretical cam curve of reactive distillation column is 15 pieces (the 41st～55 pieces).
N-propyl acetate product distillates from tower top, and ethylene glycol product distillates from tower reactor.Tower top,
Tower reactor product quality composition is shown in Table 4.Joint production process reactive distillation column reboiler is independent
Produce the 57.4% of n-propyl acetate technique reboiler.
Table 4
[embodiment 4]
Embodiment is same as in Example 1.
The alcohol used is n-butyl alcohol, wherein n-butyl alcohol: acetic acid: molar ratio
=1.2:1:1.
The theoretical cam curve of reactive distillation column is 70 pieces (number of plates is counted from top to bottom), tower
Top operation pressure is 120kPa, and tower top operation temperature is 121 DEG C, and tower reactor operation pressure is
150kPa, tower reactor operation temperature is 202 DEG C, and reflux ratio is 2.2.
The rectifying section theoretical cam curve of reactive distillation column is 30 pieces (the 1st～30 pieces).
The conversion zone theoretical cam curve of reactive distillation column is 20 pieces (the 31st～50 pieces).
The stripping section theoretical cam curve of reactive distillation column is 20 pieces (the 51st～70 pieces).
N-butyl acetate product distillates from tower top, and ethylene glycol product distillates from tower reactor.Tower top,
Tower reactor product quality composition is shown in Table 5.Joint production process reactive distillation column reboiler is independent
Produce the 69.7% of n-butyl acetate technique reboiler.
Table 5
Claims (11)
1. acetas and a co-production for ethylene glycol, under conditions of catalyst exists, acetic acid and alcohol generation esterification generate acetas and water, and the water that oxirane and esterification generate reacts coproduction ethylene glycol, comprises the steps of
A) adding acetic acid on single reactive distillation column top, bottom adds alcohol and the mixture of oxirane；Acetic acid feed position is rectifying section to tower top, is that the mixture feed entrance point of conversion zone, alcohol and oxirane is stripping section to tower reactor between the mixture feed entrance point of acetic acid feed position and alcohol and oxirane；
B) rectifying section fills filler, conversion zone catalyst filling and filler, and stripping section fills filler；
C) acetic acid and alcohol generation esterification generate acetas and water, and the water generation hydration reaction that oxirane and esterification generate simultaneously generates ethylene glycol；
D) by the rectifying action of reactive distillation column, reactive distillation tower top obtains acetas product, and tower reactor obtains ethylene glycol, diethylene glycol, triethylene glycol and Polyethylene Glycol；
E) reactive distillation tower reactor liquid respectively obtains the heavy constituents such as ethylene glycol product, diethylene glycol product, triethylene glycol product and Polyethylene Glycol through rectification.
Acetas the most according to claim 1 and the co-production of ethylene glycol, it is characterised in that described alcohol is selected from C1～C5At least one of positive structure or isomery alcohol apoplexy due to endogenous wind.
Acetas the most according to claim 2 and the co-production of ethylene glycol, it is characterised in that at least one in ethanol, isopropanol, normal propyl alcohol or n-butyl alcohol of described alcohol.
Acetas the most according to claim 1 and the co-production of ethylene glycol, it is characterised in that alcohol is 1:1～1.20:1 with the mol ratio of acetic acid.
Acetas the most according to claim 1 and the co-production of ethylene glycol, it is characterised in that alcohol is 1:1～1.20:1 with the mol ratio of oxirane.
Acetas the most according to claim 1 and the co-production of ethylene glycol, the theoretical cam curve that it is characterized in that described reactive distillation column is 45～70 pieces, tower top operation pressure is 100～150kPa, tower top operation temperature is 65～140 DEG C, tower reactor operation pressure is 120～180kPa, tower reactor operation temperature is 180～240 DEG C, and reflux ratio is 1～5.
Acetas the most according to claim 6 and the co-production of ethylene glycol, the theoretical cam curve that it is characterized in that described reactive distillation column is 50～65 pieces, tower top operation pressure is 100～120kPa, tower top operation temperature is 75～125 DEG C, tower reactor operation pressure is 130～150kPa, tower reactor operation temperature is 190～210 DEG C, and reflux ratio is 2～4.
Acetas the most according to claim 1 and the co-production of ethylene glycol, it is characterised in that the theoretical cam curve of described reactive distillation column conversion zone is 10～20 pieces.
Acetas the most according to claim 1 and the co-production of ethylene glycol, it is characterised in that the theoretical cam curve of described reactive distillation column rectifying section is 10～30 pieces.
Acetas the most according to claim 1 and the co-production of ethylene glycol, it is characterised in that the theoretical cam curve of described reactive distillation column stripping section is 10～20 pieces.
11. acetass according to claim 1 and the co-production of ethylene glycol, it is characterised in that described ethylene glycol high-class product is from purifying ethylene glycol tower side take-off, and tower top is ethylene glycol Grade A.
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| CN201510172179.3A CN106146299B (en) | 2015-04-13 | 2015-04-13 | The method for producing acetic acid esters and ethylene glycol |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106146298A (en) * | 2015-04-13 | 2016-11-23 | 中国石油化工股份有限公司 | Acetas and the co-production of ethylene glycol |
| CN107602374A (en) * | 2017-10-09 | 2018-01-19 | 福州大学 | A kind of method based on ethylene oxide hydration reactive distillation separation carboxylic acid |
| US11198664B2 (en) | 2017-06-30 | 2021-12-14 | Johnson Matthey Davy Technologies Limited | Process for the purification of ethylene glycol |
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| US4018816A (en) * | 1974-12-19 | 1977-04-19 | Mitsubishi Chemical Industries Ltd. | Preparation of methacrylates |
| CN1657514A (en) * | 2004-02-18 | 2005-08-24 | 中国石油化工股份有限公司 | Method of preparing ethylene glycol |
| CN102875327A (en) * | 2012-10-30 | 2013-01-16 | 中国海洋大学 | Technique for preparing absolute ethanol from near-azeotropic-concentration ethanol-water mixture |
| CN104418701A (en) * | 2013-09-11 | 2015-03-18 | 中国科学院过程工程研究所 | Method for synthesizing diethyl carbonate and coproducing diol by using carbon dioxide |
| CN106146298A (en) * | 2015-04-13 | 2016-11-23 | 中国石油化工股份有限公司 | Acetas and the co-production of ethylene glycol |
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2015
- 2015-04-13 CN CN201510172179.3A patent/CN106146299B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4018816A (en) * | 1974-12-19 | 1977-04-19 | Mitsubishi Chemical Industries Ltd. | Preparation of methacrylates |
| CN1657514A (en) * | 2004-02-18 | 2005-08-24 | 中国石油化工股份有限公司 | Method of preparing ethylene glycol |
| CN102875327A (en) * | 2012-10-30 | 2013-01-16 | 中国海洋大学 | Technique for preparing absolute ethanol from near-azeotropic-concentration ethanol-water mixture |
| CN104418701A (en) * | 2013-09-11 | 2015-03-18 | 中国科学院过程工程研究所 | Method for synthesizing diethyl carbonate and coproducing diol by using carbon dioxide |
| CN106146298A (en) * | 2015-04-13 | 2016-11-23 | 中国石油化工股份有限公司 | Acetas and the co-production of ethylene glycol |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106146298A (en) * | 2015-04-13 | 2016-11-23 | 中国石油化工股份有限公司 | Acetas and the co-production of ethylene glycol |
| US11198664B2 (en) | 2017-06-30 | 2021-12-14 | Johnson Matthey Davy Technologies Limited | Process for the purification of ethylene glycol |
| CN107602374A (en) * | 2017-10-09 | 2018-01-19 | 福州大学 | A kind of method based on ethylene oxide hydration reactive distillation separation carboxylic acid |
| CN107602374B (en) * | 2017-10-09 | 2019-10-15 | 福州大学 | A method of carboxylic acid is separated based on ethylene oxide hydration reactive distillation |
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