CN112358382A - Novel method for continuously increasing yield of triethylene glycol - Google Patents
Novel method for continuously increasing yield of triethylene glycol Download PDFInfo
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- CN112358382A CN112358382A CN202011120985.3A CN202011120985A CN112358382A CN 112358382 A CN112358382 A CN 112358382A CN 202011120985 A CN202011120985 A CN 202011120985A CN 112358382 A CN112358382 A CN 112358382A
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- glycol
- triethylene glycol
- diethylene glycol
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 title claims abstract description 87
- 238000000034 method Methods 0.000 title claims abstract description 23
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 244
- 230000036571 hydration Effects 0.000 claims abstract description 30
- 238000006703 hydration reaction Methods 0.000 claims abstract description 30
- 239000007788 liquid Substances 0.000 claims abstract description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 58
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000012295 chemical reaction liquid Substances 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000001704 evaporation Methods 0.000 claims description 15
- 230000008020 evaporation Effects 0.000 claims description 15
- 239000011259 mixed solution Substances 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims description 3
- 238000011144 upstream manufacturing Methods 0.000 claims description 3
- 238000010924 continuous production Methods 0.000 claims 1
- 230000000638 stimulation Effects 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 20
- GAPFINWZKMCSBG-UHFFFAOYSA-N 2-(2-sulfanylethyl)guanidine Chemical compound NC(=N)NCCS GAPFINWZKMCSBG-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003345 natural gas Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002760 rocket fuel Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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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
-
- 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
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
-
- 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
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
- C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a novel method for continuously increasing the yield of triethylene glycol, which circularly applies diethylene glycol or a mixed liquid of crude diethylene glycol and triethylene glycol circularly, enters a hydration reactor and a triethylene glycol reactor, and is hydrated with EO to generate triethylene glycol, so that the concentration of diethylene glycol in the hydration reactor is improved, the yield of TEG can be regulated, the aim of increasing the yield of triethylene glycol is fulfilled, and the problem of low yield of triethylene glycol (TEG) in the conventional EOEG device is solved.
Description
Technical Field
The invention relates to the technical field of triethylene glycol production, in particular to a novel method for continuously increasing the yield of triethylene glycol.
Background
Triethylene glycol (also known as triethylene glycol, abbreviated as TEG) can be used as a solvent for extracting aromatic hydrocarbon, a solvent for rubber and nitrocellulose, a diesel additive and rocket fuel. In addition, the dye has wide application in the industries of medicine, coating, textile, printing and dyeing, food, paper making, cosmetics, leather making, photography, printing, metal processing and the like. It is commonly used as a plasticizer for textile auxiliary, solvent, rubber and resin, a viscosity improver for lubricating oil and an aromatic hydrocarbon extractant for reformate. With the development of natural gas chemical industry, triethylene glycol is mainly used for natural gas dehydration, and compared with other solvents, triethylene glycol solvent has a series of advantages of good thermal stability and the like, and is not in demand in the market.
Domestic TEG products are mainly derived from ethylene glycol plants as by-products of the ethylene glycol plants. The production technology of ethylene oxide glycol (EO/EG) devices is mature, the prior art mainly comprises DOW, SD, Shell and other technologies, and the production experience has been many years at home and abroad. Ethylene Oxide (EO) is mixed with water and fed into an Ethylene Glycol (EG) reactor where the acetaldehyde-containing ethylene oxide reacts with water and is completely converted to ethylene glycol (M EG). Since the moles of water in the reaction feed are much higher than ethylene oxide, very small amounts of diethylene glycol (DEG), triethylene glycol (TEG) and polyethylene glycol are produced. The reaction solution is subjected to multiple-effect evaporation, rectification, drying and dehydration to obtain the ethylene glycol product. And a small amount of diethylene glycol, triethylene glycol and polyethylene glycol are produced as byproducts. In the prior art, the triethylene glycol yield of an EOEG device is the minimum, and is about 0.4% of the monoethylene glycol yield and 5% of the diethylene glycol yield. The EOEG product has a diethylene glycol market price of 4600 yuan and an industrial grade triethylene glycol market price of 10300 yuan. The existing EOEG device products, namely monoethylene glycol and diethylene glycol, are at profit and loss edges, triethylene glycol has strong profit and profit capacity, and if diethylene glycol with low additional value can be converted into triethylene glycol, the economic benefit of the device can be obviously increased, and the competitiveness of the EOEG device is enhanced. The triethylene glycol mainly comes from byproducts produced in the process of preparing ethylene glycol by hydrating ethylene oxide, has low yield and can not meet the market demand.
Patent CN201610903407.4 discloses a method for continuously producing high-purity triethylene glycol, which uses a high-vacuum wiped-film evaporator, but does not fundamentally solve the problem of low yield of triethylene glycol.
Disclosure of Invention
The invention provides a novel method for continuously increasing the yield of triethylene glycol aiming at the problems in the prior art, and the method can be used for continuously increasing the yield of TEG of an EOEG device.
In order to achieve the purpose, the invention adopts the technical scheme that:
the invention provides a new method for continuously increasing the yield of triethylene glycol, which comprises the following process flows:
reacting ethylene oxide with water in an ethylene oxide hydration reactor, and feeding the reacted components into a multi-effect evaporation unit, a monoethylene glycol rectifying tower and a diethylene glycol rectifying tower;
after the pressure of diethylene glycol extracted from the top of the diethylene glycol rectifying tower or the mixed liquid of crude diethylene glycol and triethylene glycol extracted from the bottom of the monoethylene glycol rectifying tower is increased by a pump, all or part of the mixed liquid is divided into two parts, wherein one part of the mixed liquid is sent back to the ethylene oxide hydration reactor to take part in reaction, and the reaction liquid enters the multi-effect evaporation unit; the other part is sent into a triethylene glycol reactor to react with the ethylene oxide, and the reaction liquid is also sent into the multi-effect evaporation unit;
and after excessive water is evaporated from the reaction liquid by the multi-effect evaporation unit, removing monoethylene glycol by the monoethylene glycol rectifying tower, and removing diethylene glycol by the diethylene glycol rectifying tower, wherein the tower bottom liquid obtained after the monoethylene glycol is removed by the monoethylene glycol rectifying tower or the diethylene glycol removed by the diethylene glycol rectifying tower is completely or partially recycled, the tower bottom component of the diethylene glycol rectifying tower enters the triethylene glycol rectifying tower, and a triethylene glycol product is obtained at the tower top.
Further, the proportion of the diethylene glycol in recycling is 10-90%.
Further, the diethylene glycol or crude diethylene glycol and triethylene glycol mixed solution returned to the ethylene oxide hydration reactor accounts for 0-100% of the total return amount.
Further, diethylene glycol is fed back to the ethylene oxide hydration reactor either upstream or downstream of the ethylene oxide hydration feed pump.
Further, the inlet temperature of the ethylene oxide hydration reactor is 120-200 ℃ and the operating pressure is 10-25 barg.
Further, the reaction temperature of the triethylene glycol reactor is 60-250 ℃, and the reaction pressure is 5-25 barg.
Further preferably, the reaction temperature of the triethylene glycol reactor is 140 ℃ and the reaction pressure is 15-20 barg.
Furthermore, the triethylene glycol reactor adopts a tubular reactor, and the residence time of the tubular reactor is 0.1-10 h.
Further preferably, the residence time is 0.167 h.
By adopting the technical scheme, compared with the prior art, the invention has the following technical effects:
the novel method for continuously increasing the yield of the triethylene glycol circularly applies the diethylene glycol or the mixed liquid of the crude diethylene glycol and the triethylene glycol circularly, enters the hydration reactor and the triethylene glycol reactor, and is hydrated with EO to generate the triethylene glycol, so that the concentration of the diethylene glycol in the hydration reactor is improved, and the yield of TEG can be regulated and controlled to achieve the purpose of increasing the yield of the triethylene glycol.
Drawings
FIG. 1 is a process flow diagram of examples 1-4 of the present invention.
Detailed Description
The present invention is further illustrated by the following examples, which are not to be construed as limiting the invention.
It should be noted that the embodiments and features of the embodiments may be combined with each other without conflict.
Example 1
In a certain 10 kiloton/year ethylene glycol device, a DEG rectifying tower produces 116kg/hr of diethylene glycol, wherein 46kg/hr of diethylene glycol is taken as a product, the rest 70kg/hr of diethylene glycol is subjected to temperature 60 ℃, the temperature is increased by a pump and then divided into two parts, the first part 35kg/hr is mixed with 4000g/h of EO aqueous solution (EO concentration is 10%) conveyed by a hydration feeding pump, the mixture is preheated to 160 ℃ and then enters an EO hydration reactor, the reactor stays for 9min, the reaction pressure is 21barg, and the reaction liquid enters a multi-effect evaporation unit. And the other stream of 35kg/hr diethylene glycol is mixed with 5kg/hr pure EO and then directly enters a TEG reactor, the reaction inlet temperature of the TEG reactor is 55 ℃, the reaction pressure is 15bar, the outlet temperature is 105 ℃, and the reaction liquid enters a multi-effect evaporation unit after being decompressed. The multi-effect evaporation unit is heated by steam, water in the reaction liquid is removed, a mixture of MEG, DEG and TEG which does not contain water is discharged from a tower kettle and is pumped into an MEG rectifying tower, 375kg/hr of MEG is obtained at the tower top, 136kg of mixed liquid of DEG and TEG in the tower kettle enters the DEG tower, 116kg/hr of DEG product is obtained at the tower top, 70kg/hr of DEG product is pumped and then returned to an EO hydration reactor for circulation, the tower kettle liquid is sent into the TEG rectifying tower, 19kg/hr of TEG product is obtained at the tower top, and 1kg/hr of heavy component is contained in the tower kettle.
Example 2
In a certain 10 kiloton/year ethylene glycol device, a DEG rectifying tower produces 110kg/hr diethylene glycol, wherein 40kg/hr diethylene glycol is taken as a product, the rest 70kg/hr diethylene glycol is subjected to pump pressure boosting and then is mixed with 7550g/h EO aqueous solution (EO concentration is 10%) conveyed by a hydration feed pump, the mixture is preheated to 160 ℃ and then enters an EO hydration reactor, the reactor stays for 9min, the reaction pressure is 21barg, the reaction liquid enters a multi-effect evaporation unit (heated by steam), water in the reaction liquid is removed, a mixture of MEG, DEG and TEG without water is discharged from a tower bottom and is conveyed into the MEG rectifying tower through a pump, 875kg/hr of MEG is obtained at the tower top, 130kg of mixed liquid of DEG and TEG enters the DEG rectifying tower, 110kg/hr DEG is obtained at the tower top, 70kg/hr of DEG is returned to the EO hydration reactor for circulation after being subjected to pump pressure boosting, the bottom of the column is fed into a TEG rectifying column, 19kg/hr of TEG product is obtained at the top of the column, and 1kg/hr of heavy component is obtained at the bottom of the column.
Example 3
In a certain 10 kiloton/year ethylene glycol device, a DEG rectifying tower produces 110kg/hr of diethylene glycol, wherein 40kg/hr of diethylene glycol is taken as a product, 40kg/hr of diethylene glycol in the rest 70kg/hr of diethylene glycol is mixed with 5550g/h of EO aqueous solution (EO concentration is 10%) conveyed by a hydration feeding pump after being pumped and pressurized, preheated to 160 ℃, and then enters an EO hydration reactor, the reactor stays for 9min, and the reaction pressure is 21 barg.
The rest 30kg/hr of diethylene glycol is pumped up to 16barg and 2000kg/hr of EO (EO concentration 10%, pumped up to 16barg by an EO feed pump) are mixed in a static mixer (SK type static mixer), and the mixture is preheated to 140 ℃ by a preheater (heated by 10barg steam) after being uniformly mixed, and then enters a TEG reactor; the reaction pressure of the TEG reactor is 15barg, the retention time is 10min, the temperature is raised to 175 ℃ after the reaction, and the reaction liquid enters a multi-effect evaporation unit after being mixed with the reaction liquid of the hydration reactor. Removing water in the reaction liquid, discharging a mixture of MEG, DEG and TEG without water from a tower kettle, pumping the mixture into an MEG rectifying tower to obtain 875kg/hr of MEG at the tower top, feeding 130kg of a mixed solution of DEG and TEG from the tower kettle into the DEG rectifying tower to obtain 110kg/hr of DEG product at the tower top, wherein 70kg/hr of DEG product is pumped and then returned to the EO hydration reactor for recycling, feeding the tower kettle into the TEG rectifying tower to obtain 19kg/hr of TEG product at the tower top, and the tower kettle is 1kg/hr of heavy component.
Example 4
In a certain 10 kiloton/year ethylene glycol device, a DEG rectifying tower produces 110kg/hr diethylene glycol, wherein 40kg/hr diethylene glycol is taken as a product, the rest 70kg/hr diethylene glycol directly enters an EO hydration upstream buffer tank, is mixed with 7550g/h EO aqueous solution (with the concentration of 10%) in the tank, is subjected to pressure rise and preheating to 160 ℃, then enters an EO hydration reactor, stays for 9min at the reactor pressure of 21barg, the reaction liquid enters a multi-effect evaporation unit (heated by steam), water in the reaction liquid is removed, a mixture of MEG, DEG and TEG which does not contain water is discharged from a tower bottom, is pumped into the MEG rectifying tower, 875kg/hr MEG is obtained at the tower top, 130kg DEG mixed liquid of the DEG and the TEG enters a DEG tower, 110kg/hr DEG product is obtained at the tower top, 65kg/hr DEG is returned to the EO hydration reactor for circulation after being subjected to pressure rise by a pump, the bottom of the column is fed into a TEG rectifying column, 19kg/hr of TEG product is obtained at the top of the column, and 1kg/hr of heavy component is obtained at the bottom of the column.
Comparative example
In a certain 10 kiloton/year ethylene glycol device, 8000g/h of EO aqueous solution (with the concentration of 10%) is pumped and boosted, sent into a preheater for preheating and raising the temperature to 160 ℃, then sent into an EO hydration reactor, the reactor stays for 9min, the reaction pressure is 21barg, the reaction liquid enters a dehydration tower after reaction, the dehydration tower is heated by steam to remove water in the reaction liquid, a mixture of MEG, DEG and TEG which does not contain water is discharged from a tower bottom, sent into an MEG rectifying tower through a pump, 875kg/hr of MEG is obtained at the tower top, 140kg of mixed liquid of DEG and TEG enters the DEG tower, 65kg/hr of DEG product is obtained at the tower top, the TEG rectifying tower is sent into the tower bottom, 0.56kg/hr of TEG product is obtained at the tower top, and the tower bottom is 1kg/hr of heavy component.
It can be seen that the method of the present invention enables a continuous increase in TEG production.
While the invention has been described with reference to a preferred embodiment, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the spirit and scope of the invention.
Claims (8)
1. A new method for continuously increasing the yield of triethylene glycol is characterized by comprising the following process flows:
reacting ethylene oxide with water in an ethylene oxide hydration reactor, and feeding the reacted components into a multi-effect evaporation unit, a monoethylene glycol rectifying tower and a diethylene glycol rectifying tower;
after the pressure of diethylene glycol extracted from the top of the diethylene glycol rectifying tower or the mixed liquid of crude diethylene glycol and triethylene glycol extracted from the bottom of the monoethylene glycol rectifying tower is increased by a pump, all or part of the mixed liquid is divided into two parts, wherein one part of the mixed liquid is sent back to the ethylene oxide hydration reactor to take part in reaction, and the reaction liquid enters the multi-effect evaporation unit; the other part is sent into a triethylene glycol reactor to react with the ethylene oxide, and the reaction liquid is also sent into the multi-effect evaporation unit;
and after excessive water is evaporated from the reaction liquid by the multi-effect evaporation unit, removing monoethylene glycol by the monoethylene glycol rectifying tower, and removing diethylene glycol by the diethylene glycol rectifying tower, wherein the tower bottom liquid obtained after the monoethylene glycol is removed by the monoethylene glycol rectifying tower or the diethylene glycol removed by the diethylene glycol rectifying tower is completely or partially recycled, the tower bottom component of the diethylene glycol rectifying tower enters the triethylene glycol rectifying tower, and a triethylene glycol product is obtained at the tower top.
2. A novel method for continuously increasing yield of triethylene glycol as claimed in claim 1, wherein the proportion of diethylene glycol used in the process of recycling is 10-90%.
3. A novel method for continuously increasing yield of triethylene glycol according to claim 1, wherein the mixed solution of diethylene glycol or crude diethylene glycol and triethylene glycol returned to the ethylene oxide hydration reactor accounts for 0-100% of the total return amount.
4. A novel process for continuous production stimulation of triethylene glycol according to claim 1, characterized in that diethylene glycol is fed back to the ethylene oxide hydration reactor upstream or downstream of an ethylene oxide hydration feed pump.
5. The novel method for continuously increasing yield of triethylene glycol as claimed in claim 1, wherein the inlet temperature of the ethylene oxide hydration reactor is 120-200 ℃ and the operating pressure is 10-25 barg.
6. A novel method for continuously increasing yield of triethylene glycol according to claim 1, wherein the reaction temperature of the triethylene glycol reactor is 60-250 ℃ and the reaction pressure is 5-25 barg.
7. A novel method for continuously increasing yield of triethylene glycol according to claim 6, wherein the reaction temperature of the triethylene glycol reactor is 140 ℃ and the reaction pressure is 15-20 barg.
8. A novel method for continuously increasing yield of triethylene glycol according to claim 1, wherein the triethylene glycol reactor is a tubular reactor, and the residence time of the triethylene glycol reactor is 0.1-10 h.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60126241A (en) * | 1983-12-13 | 1985-07-05 | Mitsui Toatsu Chem Inc | Production of triethylene glycol |
| US20050119510A1 (en) * | 2003-09-26 | 2005-06-02 | Boons Petrus J.G. | Process of preparing an alkylene glycol |
| KR20120091594A (en) * | 2011-02-09 | 2012-08-20 | 삼성토탈 주식회사 | A method for producing diethylene glycol from ethylene oxide with high yield |
| JP2013129613A (en) * | 2011-12-20 | 2013-07-04 | Mitsubishi Chemicals Corp | Method of producing trialkylene glycol |
| CN106542975A (en) * | 2016-10-17 | 2017-03-29 | 中石化上海工程有限公司 | The method of continuous production high-purity triethylene glycol |
-
2020
- 2020-10-19 CN CN202011120985.3A patent/CN112358382A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60126241A (en) * | 1983-12-13 | 1985-07-05 | Mitsui Toatsu Chem Inc | Production of triethylene glycol |
| US20050119510A1 (en) * | 2003-09-26 | 2005-06-02 | Boons Petrus J.G. | Process of preparing an alkylene glycol |
| KR20120091594A (en) * | 2011-02-09 | 2012-08-20 | 삼성토탈 주식회사 | A method for producing diethylene glycol from ethylene oxide with high yield |
| JP2013129613A (en) * | 2011-12-20 | 2013-07-04 | Mitsubishi Chemicals Corp | Method of producing trialkylene glycol |
| CN106542975A (en) * | 2016-10-17 | 2017-03-29 | 中石化上海工程有限公司 | The method of continuous production high-purity triethylene glycol |
Non-Patent Citations (2)
| Title |
|---|
| 《化工百科全书》编辑部: "《化工百科全书 第18卷 锌和锌合金-硬质合金》", 30 September 1998 * |
| 吕百龄: "《实用工业助剂全书》", 31 August 2001, 化学工业出版社 * |
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