WO2022122030A1 - Procédé et dispositif de purification d'un intermédiaire de procédure de grignard maltol - Google Patents
Procédé et dispositif de purification d'un intermédiaire de procédure de grignard maltol Download PDFInfo
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- WO2022122030A1 WO2022122030A1 PCT/CN2021/137217 CN2021137217W WO2022122030A1 WO 2022122030 A1 WO2022122030 A1 WO 2022122030A1 CN 2021137217 W CN2021137217 W CN 2021137217W WO 2022122030 A1 WO2022122030 A1 WO 2022122030A1
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- flash
- kettle
- temperature
- maltol
- tank
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- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 47
- HYMLWHLQFGRFIY-UHFFFAOYSA-N Maltol Natural products CC1OC=CC(=O)C1=O HYMLWHLQFGRFIY-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 229940043353 maltol Drugs 0.000 title claims abstract description 30
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims abstract description 189
- 239000002904 solvent Substances 0.000 claims abstract description 43
- 238000000926 separation method Methods 0.000 claims abstract description 26
- 238000007701 flash-distillation Methods 0.000 claims abstract description 19
- 239000012530 fluid Substances 0.000 claims abstract 2
- 238000005292 vacuum distillation Methods 0.000 claims description 31
- 238000009833 condensation Methods 0.000 claims description 12
- 230000005494 condensation Effects 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- 238000000746 purification Methods 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 6
- 239000012595 freezing medium Substances 0.000 claims description 6
- 239000002609 medium Substances 0.000 claims 1
- 238000004821 distillation Methods 0.000 abstract description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 27
- 239000000543 intermediate Substances 0.000 description 25
- 239000007788 liquid Substances 0.000 description 19
- 239000012071 phase Substances 0.000 description 19
- 230000008569 process Effects 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000012535 impurity Substances 0.000 description 11
- BJUHFDPHMUCXFC-UHFFFAOYSA-N 1-(furan-2-yl)butan-2-ol Chemical compound CCC(O)CC1=CC=CO1 BJUHFDPHMUCXFC-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000012808 vapor phase Substances 0.000 description 3
- YIKYNHJUKRTCJL-UHFFFAOYSA-N Ethyl maltol Chemical compound CCC=1OC=CC(=O)C=1O YIKYNHJUKRTCJL-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229940093503 ethyl maltol Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
- C07D307/44—Furfuryl alcohol
-
- 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
Definitions
- the invention relates to a method for purifying an intermediate of a maltol Grignard section.
- Chinese patent document CN110790732A discloses a method for refining and purifying furfuryl alcohol in the production of maltol.
- the first tetrahydrofuran tank; a high-concentration furfuryl alcohol solution containing tetrahydrofuran is extracted from the bottom of the rectification tower, and pumped to the distillation kettle to control the temperature at 68 °C-75 °C and vacuum degree -0.095 to -0.099MPa for distillation, and the reduced
- the solvent tetrahydrofuran steamed from the still is pumped to the second tetrahydrofuran tank, and then the tetrahydrofuran is pumped back to the rectifying tower for circulating rectification through pipelines.
- Chinese patent document CN209317065U discloses a vacuum distillation device for ethyl maltol that reduces energy consumption, including a furfuryl propanol dilute solution receiving tank, a vacuum distillation still, a tube condenser, a furfuryl propanol storage tank and a solvent recovery device , the furfuryl propanol dilute solution receiving tank is connected to the vacuum distillation kettle, the liquid outlet end of the vacuum distillation kettle top is connected to the liquid and gas inlet end of the gas-liquid separator, and the gas outlet end of the gas-liquid separator is connected to the liquid inlet end of the tube condenser
- the liquid outlet end of the tube condenser is connected with the liquid inlet end of the solvent recovery device; the liquid outlet of the gas-liquid separator is connected with the top of the vacuum distillation kettle, and the liquid outlet end at the bottom of the vacuum distillation kettle is connected with the furfuryl propanol storage tank.
- the energy consumption of the separation and purification method is relatively high, and the content of the purified furfuryl alcohol is not high, and there are many impurities.
- the recovered solvent also contains more furfuryl alcohol.
- the yield of furfuryl alcohol is low and the quality is not high.
- the technical problem to be solved by the present invention is to provide a method for purifying a maltol Grignard section intermediate, which can improve the content and yield of furfuryl alcohol, solve intermittent repetitive operations, and reduce labor intensity of personnel.
- the present invention provides a method for purifying a maltol Grignard section intermediate, which is characterized in that, comprising the following steps:
- the intermediate enters the rectifying tower at a flow rate of 2 m 3 /h to carry out the rough separation of furfuryl alcohol and the solvent, and the temperature at the bottom of the rectifying tower is 60° C. and the temperature at the top of the tower is 40° C.;
- the extraction flow rate is 1.5 m 3 /h
- the temperature of the first-level flash tank is 85°C
- the gas phase of the first-level flash tank is condensed and then enters the second-level flash tank Flash kettle
- the temperature of the secondary flash kettle is 65°C
- the gas phase of the secondary flash kettle is condensed and then enters the tertiary flash kettle
- the temperature of the third flash kettle is 60°C.
- the freezing medium temperature of above-mentioned gas phase condensation is -5 °C ⁇ -8 °C
- all above-mentioned flashing stills all adopt vacuum distillation, and vacuum degree is -0.08MPa;
- the qualified furfuryl alcohol is extracted from the bottom of the first-stage flash tank according to the flow rate of 0.5 m 3 /h, and the content of the extracted furfuryl alcohol is analyzed every hour.
- step (2) the solvent after the vapor phase condensation of the three-stage flash tank is used for washing magnesium slag in production.
- the present invention realizes continuous production, has strong operability, reduces consumption, and improves the yield and quality of furfuryl alcohol. It plays a decisive role in improving the yield of the whole maltol product.
- FIG. 1 is a flow chart of the equipment of this method.
- the equipment corresponding to this method includes a rectifying tower 1, a first flash tank 41, a second flash tank 42, a third flash tank 43, a first condenser 21, and a second condenser 22 , the third condenser 23, the fourth condenser 24, the first pump 51, the second pump 52, the first solvent tank 31, the second solvent tank 32, the furfuryl alcohol tank 33, and a reboiler 11 is provided on the side of the rectifying tower 1 And connected with the rectification tower 1 through the circulation pipeline, the upper outlet of the rectification tower 1 is connected with the first condenser 21, the other end of the first condenser 21 is connected with the first solvent tank 31, and the lower outlet of the rectification tower 1 is connected with the first condenser 21.
- the first pump 51 is connected to the inlet end of the first flash still 41, the lower outlet of the first flash still is connected to the furfuryl alcohol tank 33, the upper outlet of the first flash still 41 is connected to the second condenser 22, and the second condenser 22
- the other end is connected with the inlet end of the second flash vessel 42, the upper outlet of the second flash vessel 42 is connected with the third condenser 23, the other end of the third condenser 23 is connected with the inlet end of the third flash vessel 43, and the third condenser 23 is connected with the inlet end of the third flash vessel 43.
- the upper outlet of the flash vessel 43 is connected to the fourth condenser 24, the other end of the fourth condenser 24 is connected to the second solvent tank 32, and the lower outlet of the second flash vessel 42 is merged with the lower outlet of the third flash vessel 43 , and is connected to the inlet end of the first flash tank 41 through the second pump 52 .
- the intermediate of the maltol Grignard section is connected to the inlet ends of the first flash tank 41 , the second flash tank 42 and the third flash tank 43 through an atomizing injector.
- the filtrate (that is, the dilute solution of furfuryl propanol) after the hydrolysis reaction is transferred into the vacuum distillation still, and the control temperature is less than or equal to 65°C, and the pressure is less than or equal to -0.088 MPa
- the vacuum distillation still distillate is cooled through the condenser, and the benzene and tetrahydrofuran solvent are separated, and the concentrated solution at the bottom of the vacuum distillation still is the purified furfuryl propanol intermediate. Then the separated solvent is re-distilled, and the temperature is controlled to 100 ° C.
- the residual liquid at the bottom of the still contains furfuryl propanol intermediate, which is then transferred to the vacuum distillation still for secondary distillation, and the residual liquid is separated. of benzene and tetrahydrofuran solvent, and extract the furfuryl propanol inside again.
- the intermediate content of furfuryl propanol extracted by the secondary re-steaming is low, the impurities are many, and the color is dark. The reason is that furfuryl propanol is decomposed and oxidized by secondary heating (high temperature) in the process of atmospheric re-distillation.
- the present invention improves the ordinary vacuum distillation into the distillation in the flash tank.
- the separation of the gas phase and the liquid phase is achieved in a very short time.
- the liquid phase gradually falls into the bottom of the flash vessel, and the gas phase is output from the flash vessel and condensed to continue processing.
- the liquid to be separated is misty when entering the flash tank, so relatively high temperature and relatively low pressure are required to realize solvent distillation in a very short time.
- the inventors of the present invention increased the flash evaporation temperature to 85 degrees Celsius in order to achieve rapid separation, so that the distillation of the solvent can be achieved in a very short time (almost instantaneously).
- the inventor also found that, due to the increase of the flash temperature, the pressure in the flash tank was simultaneously increased (-0.08MPa). The increase of the pressure in the flash tank reduces the requirement of the system on the vacuum device and reduces the energy consumption of the vacuum generating device.
- the material extracted from the bottom of the tower is directly fed into the flashing kettle for flashing; the flashing is also a continuous process.
- the invention does not collect the intermediate until the volume of the intermediate meets the amount of vacuum distillation, and after the rectifying column runs smoothly, the material can be directly extracted from the bottom of the rectifying column and enter the flash kettle for flash distillation; When the substance enters the flash tank, the flash evaporation is completed in a very short speed, which is a continuous working process.
- the present invention adopts such a method, so that the whole reaction process is carried out continuously, changing the two-stage waiting time necessary for the vacuum distillation of the whole still, on the one hand, reducing the time-consuming (with waiting process) of the distillation separation process, and on the other hand, continuous
- the chemical operation improves the operation efficiency of the entire production line. For example, if the whole-pot vacuum distillation method is adopted, the continuous operation of the same rectifying tower requires at least two sets of vacuum distillation kettles to realize the continuous work of the pre-stage and subsequent sections of distillation and separation. , so the present invention reduces the equipment cost.
- furfuryl alcohol After furfuryl alcohol is obtained by separation in the primary flash tank, it can be directly recovered without further separation of the gas phase; however, the gas phase condensation product of the primary flash tank still contains more furfuryl alcohol.
- the second-stage flash evaporation and the third-stage flash evaporation are continued for the vapor-phase condensation product of the first-stage flash tank, so as to finally obtain a solvent with higher purity; due to the flash treatment, the side reaction of the solvent There is also a corresponding reduction. Calculated at an initial flow rate of 2 m 3 /h, about 13 liters of solvent can be recovered per hour.
- the intermediate enters the rectifying tower at a flow rate of 2 m 3 /h to carry out the rough separation of furfuryl alcohol and the solvent.
- the temperature at the bottom of the rectifying tower is 60° C. and the temperature at the top of the tower is 40° C. In this process, about 25%
- the liquid collected at the top of the tower, the main component of this part of the liquid is solvent, and also contains a part of furfuryl alcohol; about 75% of the liquid is collected at the bottom of the tower, and this part of the liquid contains more furfuryl alcohol.
- the extraction flow rate is 1.5m 3 /h
- the intermediate is sprayed into the first-level flash using a pump using an atomizing injector, such as a venturi tube.
- the temperature of the primary flash kettle is 85°C
- the gas phase of the primary flash kettle enters the secondary flash kettle after condensation
- the temperature of the secondary flash kettle is 65°C
- the gas phase of the secondary flash kettle is condensed.
- the temperature of the three-stage flash distillation still is 60 °C
- the collection after the gas phase condensation of the three-stage flash distillation still the freezing medium temperature of the above-mentioned vapor phase condensation is -5 to -8 °C
- all the above-mentioned flash stills are Using vacuum distillation, the vacuum degree is -0.08MPa;
- the qualified furfuryl alcohol is extracted from the bottom of the first-stage flash tank according to the flow rate of 0.5 m 3 /h, and the content of the extracted furfuryl alcohol is analyzed every hour.
- a method for purifying a maltol Grignard section intermediate comprising the following steps:
- the intermediate enters the rectifying tower at a flow rate of 2 m 3 /h to carry out the rough separation of furfuryl alcohol and the solvent, and the temperature at the bottom of the rectifying tower is 60° C. and the temperature at the top of the tower is 40° C.;
- the extraction flow rate is 1.5 m 3 /h
- the temperature of the first-level flash tank is 85°C
- the gas phase of the first-level flash tank is condensed and then enters the second-level flash tank Flash kettle
- the temperature of the secondary flash kettle is 65°C
- the gas phase of the secondary flash kettle is condensed and then enters the tertiary flash kettle
- the temperature of the third flash kettle is 60°C.
- the freezing medium temperature of above-mentioned gas phase condensation is -5 °C
- all above-mentioned flashing stills all adopt vacuum distillation, and vacuum degree is -0.08MPa;
- the qualified furfuryl alcohol is extracted from the bottom of the first-stage flash tank according to the flow rate of 0.5 m 3 /h, and the content of the extracted furfuryl alcohol is analyzed every hour.
- Embodiment 2 is a diagrammatic representation of Embodiment 1:
- a method for purifying a maltol Grignard section intermediate comprising the following steps:
- the intermediate enters the rectifying tower at the flow rate of 2m 3 /h to carry out the rough separation of furfuryl alcohol and the solvent, and the temperature at the bottom of the rectifying tower is 60° C.
- the extraction flow rate is 1.5 m 3 /h
- the temperature of the first-level flash tank is 85°C
- the gas phase of the first-level flash tank is condensed and then enters the second-level flash tank Flash kettle
- the temperature of the secondary flash kettle is 65°C
- the gas phase of the secondary flash kettle is condensed and then enters the tertiary flash kettle
- the temperature of the third flash kettle is 60°C.
- the freezing medium temperature of above-mentioned gas phase condensation is -6.5 °C
- all above-mentioned flashing stills all adopt vacuum distillation, and vacuum degree is -0.08MPa;
- the qualified furfuryl alcohol is extracted from the bottom of the first-stage flash tank according to the flow rate of 0.5 m 3 /h, and the content of the extracted furfuryl alcohol is analyzed every hour.
- a method for purifying a maltol Grignard section intermediate comprising the following steps:
- the intermediate enters the rectifying tower at a flow rate of 2 m 3 /h to carry out the rough separation of furfuryl alcohol and the solvent, and the temperature at the bottom of the rectifying tower is 60° C. and the temperature at the top of the tower is 40° C.;
- the extraction flow rate is 1.5 m 3 /h
- the temperature of the first-level flash tank is 85°C
- the gas phase of the first-level flash tank is condensed and then enters the second-level flash tank Flash kettle
- the temperature of the secondary flash kettle is 65°C
- the gas phase of the secondary flash kettle is condensed and then enters the tertiary flash kettle
- the temperature of the third flash kettle is 60°C.
- the freezing medium temperature of above-mentioned gas phase condensation is -8 °C
- all above-mentioned flashing stills all adopt vacuum distillation, and vacuum degree is -0.08MPa;
- the qualified furfuryl alcohol is extracted from the bottom of the first-stage flash tank according to the flow rate of 0.5 m 3 /h, and the content of the extracted furfuryl alcohol is analyzed every hour.
- the intermediate enters the rectifying tower at a flow rate of 2 m 3 /h to carry out the rough separation of furfuryl alcohol and the solvent, and the temperature at the bottom of the rectifying tower is 60° C. and the temperature at the top of the tower is 40° C.;
- the data of three consecutive vacuum distillation kettles were collected, and the furfuryl alcohol content was analyzed.
- the furfuryl alcohol content of the liquid separated from the top of the rectification column is 1.26%, 1.28% and 1.31%.
- the time of distillation and separation is reduced, and the utilization rate of equipment is improved; because the heating time of distillation and separation is reduced, the content of impurities contained in furfuryl alcohol is obviously reduced, and the cost of separation of impurities in the subsequent process is reduced; at the same time,
- the reduction of the impurity amount of furfuryl alcohol conversion increases the output of furfuryl alcohol, as in still kettle volume 4m , according to the present invention about 2 hours of reaction can complete the amount of a kettle, with the above impurity quantity calculation, single kettle output by the original 960kg increased to 980kg; using multi-stage flash evaporation, the solvent can be recovered by about 300 liters per day.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Vaporization, Distillation, Condensation, Sublimation, And Cold Traps (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Est divulgué un procédé de purification d'un intermédiaire de procédure de Grignard maltol caractérisé en ce qu'il comprend les étapes suivantes : étape 1 : introduction d'un intermédiaire dans une tour de distillation pour séparation grossière d'alcool furfurylique et d'un solvant, la température au fond de la tour de distillation étant supérieure à la température au sommet de la tour ; étape 2 : introduction d'un fluide provenant du fond de la tour de distillation dans une chaudière de distillation flash de premier étage, la température de la chaudière de distillation flash de premier étage étant supérieure à la température au fond de la tour de distillation, et la condensation d'une phase gazeuse de la chaudière de distillation flash de premier étage puis l'introduction dans une chaudière de distillation flash de second étage ; étape 3 : la température de la chaudière de distillation flash de second étage étant inférieure à la température de la chaudière de distillation flash de premier étage, et condensation d'une phase gazeuse de la chaudière de distillation flash de deuxième étage puis introduction dans la chaudière de distillation flash de troisième étage ; étape 4 : la température de la chaudière de distillation flash de troisième étage étant inférieure à la température de la chaudière de distillation flash de deuxième étage, et condensation d'une phase gazeuse de la chaudière de distillation flash de troisième étage puis collecte. Est divulgué également un dispositif de purification d'un intermédiaire de procédure de Grignard maltol. Le procédé et le dispositif selon la divulgation peuvent augmenter la teneur et le rendement de l'alcool furfurylique.
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AU758889B2 (en) * | 1998-11-24 | 2003-04-03 | University Of Melbourne, The | Process for the recovery of low molecular weight phenols, furfural, furfuryl alcohol and/or cellulose or cellulose-rich residues |
CN100551920C (zh) * | 2007-06-06 | 2009-10-21 | 济南圣泉集团股份有限公司 | 糠醇精制方法及其装置 |
JP2009269062A (ja) * | 2008-05-08 | 2009-11-19 | Gun Ei Chem Ind Co Ltd | 鋳型造型用粘結剤組成物、鋳型造型用砂組成物および鋳型の製造方法 |
CN207024668U (zh) * | 2017-03-02 | 2018-02-23 | 山东一诺生物质材料有限公司 | 一种糠醇生产中的节能降耗装置 |
CN109020929B (zh) * | 2018-07-30 | 2023-11-17 | 河南心连心化学工业集团股份有限公司 | 一种粗糠醇分离装置及其分离工艺 |
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2020
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US4305790A (en) * | 1980-01-31 | 1981-12-15 | Kramer Sr Edward F | Multiple effect distillation method and apparatus |
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