KR101783219B1 - Method for recovering byproduct in epoxy manufacturing process using distillation and pervaporation - Google Patents
Method for recovering byproduct in epoxy manufacturing process using distillation and pervaporation Download PDFInfo
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- KR101783219B1 KR101783219B1 KR1020150128518A KR20150128518A KR101783219B1 KR 101783219 B1 KR101783219 B1 KR 101783219B1 KR 1020150128518 A KR1020150128518 A KR 1020150128518A KR 20150128518 A KR20150128518 A KR 20150128518A KR 101783219 B1 KR101783219 B1 KR 101783219B1
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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
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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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/10—Monohydroxylic acyclic alcohols containing three carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Abstract
Disclosed is a method for recovering unreacted by-products resulting from an epoxy production process using distillation and pervaporation.
The method for recovering by-products in an epoxy manufacturing process according to the present invention comprises the steps of: (a) one-step distilling by-product of epoxy production process including IPA, ECH and H 2 O; (b) pervaporating the first stage distillate to recover IPA and ECH; (c) distilling the residue of step (a) in which the first-stage distillate is removed in two stages; And (d) recovering ECH from the two-stage distillate.
Description
The present invention relates to a method for recovering isopropyl alcohol (IPA) and epichlorohydrin (ECH) from a byproduct of an epoxy resin production process, and more particularly, to a method for recovering isopropyl alcohol (IPA) and epichlorohydrin In order to improve the process of recovering the by-products recovered by the distillation method of distillation under reduced pressure and to increase the reaction efficiency, an excess of by-product produced in the process is refined by a distillation and pervaporation membrane process and then an improved epoxy resin And a method for recovering IPA and ECH from process byproducts.
Epoxy resin is a kind of thermosetting resin and has excellent mechanical properties, high strength, high modulus and high glass transition temperature (Tg) due to chemical resistance, dimensional stability and crosslinked microstructure, It has been widely used in almost all industrial fields because it has a wide range of applications to space satellites.
Epoxies used in composite materials are epoxy resins with two or more functional groups. Among them, epoxy resins with four functional groups are excellent in weatherability, heat resistance and tensile strength, and can be used as a matrix or adhesive for composite materials.
An alcohol-based solvent is used in the epoxy production process using epichlorohydrin (ECH) as a raw material, and isopropyl alcohol (IPA) is a typical example. However, excess of IPA and ECH mixture needs to be used in order to combine four ECHs for the production of four-functional epoxy, which increases the amount of IPA and ECH used in the reaction process and affects the final product cost.
In addition, water is used in the water washing process, which causes a problem that the emulsion state remains between the epoxy resin and the water layer, and the state of the emulsion between the oil / water interface is maintained for a long time, thereby increasing the processing time. In addition, the 4-functional epoxy resin is more expensive than the 2-functional or 3-functional epoxy, and water is used in deodorizing and washing processes, and a large amount of wastewater is produced, and the unit price of the 4-functional epoxy resin is sold at a high price in another epoxy.
However, in the case of the 4-functional epoxy production process, the heat generation in the reaction process is more severe than in the 2-functional or 3-functional epoxy production process. Accordingly, in order to manufacture a four-function epoxy resin, a facility for solving the heat generation problem including the cooling water is essential, and energy loss is large.
Therefore, it is required to increase the efficiency of the polyfunctional epoxy resin synthesis reaction process and to separate and purify excess ECH and IPA, which are generated as a byproduct of the epoxy production process, to reuse and shorten the reaction process time.
The present invention relates to a method for recovering excess ECH and IPA that arise as a by-product of the epoxy manufacturing process among these needs.
Figure 1 schematically shows a conventional epoxy resin and by-product recovery process.
Referring to FIG. 1, in the conventional by-product recovery process, the byproducts remaining after the epoxy production are simply distilled under reduced pressure to recover unreacted ECH and IPA, and then reused.
The recovered mixture containing ECH / IPA in the conventional recovered process is called JT-9. In the first vacuum distillation method, JT-9 is initially in a weight ratio of ECH: IPA: H 2 O = 3 to 5.5: 2.5 to 5.5 : It forms a mixture ratio of about 1.5 to 2.0. When the purity is gradually lowered and the impurities other than ECH and IPA are over 20% on the non-gas chromatograph, the epoxy resin is used as the reaction raw material, There arises a problem of lowering the physical properties of the resin.
Since the JT-9 mixture increases the concentration of impurities due to hydrolysis and dimerization and trimerization of ECH or epoxy monomer as the number of times of reuse increases, in the process of recovering ECH and IPA by the first vacuum distillation method, It is the reason for the cost increase due to the loss of raw materials and disposal costs.
A background art related to the present invention is Korean Patent Registration No. 10-0153254 (registered on July 02, 1998), which discloses a method for recovering water-insoluble epoxy alcohol using distillation.
It is an object of the present invention to provide a method for efficiently recovering ECH and IPA from by-products composed of by-products recovered in a vacuum distillation process in an epoxy resin manufacturing process, that is, by-products composed of ECH, IPA, H 2 O and the like.
In order to accomplish the above object, a method for recovering by-products in an epoxy manufacturing process using distillation and pervaporation according to an embodiment of the present invention comprises the steps of: (a) separating isopropyl alcohol (IPA), epichlorohydrin (ECH A step of distilling the by-product of the epoxy production process including water to a first stage; (b) pervaporating the first stage distillate to recover IPA and ECH; (c) distilling the residue of step (a) in which the first-stage distillate is removed in two stages; And (d) recovering ECH from the two-stage distillate.
At this time, in the step (b), a pervaporation layer including a silica separation layer may be used.
On the other hand, the pervaporation membrane may be prepared by providing an a-alumina support, forming an intermediate layer on the a-alumina support, and forming a silica separation layer on the intermediate layer.
In this case, it is preferable that the step of forming the silica separation layer is performed by using a silica sol, and the silica sol is prepared by performing a hydrolysis-condensation reaction of the TEOS precursor using 1.0 to 3.0 wt% hydrochloric acid catalyst.
The one-stage distillation may be performed at 80 to 90 ° C, and the two-stage distillation may be performed at 105 to 115 ° C.
According to the present invention, by using distillation and pervaporation, ECH and IPA, which are unreacted by-products, can be effectively recovered in an epoxy resin manufacturing process.
More specifically, a mixture of ECH and IPA can be obtained by one-step distillation, in which a large amount of water can be removed by pervaporation. Therefore, since ECH and IPA can be supplied as a raw material for producing epoxy resin again with the water which causes the hydrolysis of the raw material to be removed as much as possible in the epoxy resin manufacturing process, the cost reduction effect can be obtained by reducing the amount of the raw material .
In addition, since the ECH obtained through the two-stage distillation is very pure, it can be directly reused as an epoxy resin raw material without a purification process. Furthermore, the purified ECH can be used as a raw material for processes that do not use IPA as a solvent.
Figure 1 schematically shows a conventional epoxy resin and by-product recovery process.
FIGS. 2 and 3 are schematic views of a method for recovering by-products generated in an epoxy manufacturing process according to an embodiment of the present invention.
FIG. 4 schematically shows a process for producing a pervaporation membrane containing a silica separation layer used in the present invention.
5 shows an example of a process for producing a pervaporation membrane containing a silica separation layer.
6 and 7 show the results of FE-SEM observation of the surface and cross section of the pervaporation membrane containing the silica separation layer used in the embodiment of the present invention. 7 shows a silica sol prepared with a 1.5 wt% hydrochloric acid catalyst.
BRIEF DESCRIPTION OF THE DRAWINGS The advantages and features of the present invention and the manner of achieving them will become apparent with reference to the embodiments described in detail below with reference to the accompanying drawings. It should be understood, however, that the invention is not limited to the disclosed embodiments, but is capable of many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, To fully disclose the scope of the invention to those skilled in the art, and the invention is only defined by the scope of the claims. Like reference numerals refer to like elements throughout the specification.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, a method for recovering by-products in an epoxy production process using distillation and pervaporation according to the present invention will be described in detail with reference to the accompanying drawings.
FIGS. 2 and 3 are schematic views of a method for recovering by-products generated in an epoxy manufacturing process according to an embodiment of the present invention.
Referring to FIGS. 2 and 3, the by-product recovery method in the epoxy manufacturing process according to the present invention includes a first stage distillation step S210, a pervaporation step S220, a second distillation step S230, S240).
In the first stage distillation step (S210), an epoxy manufacturing process by-product (so-called JT-9) containing isopropyl alcohol (IPA), epichlorohydrin (ECH) and water is distilled in one step.
As described above, the by-product of the epoxy production process corresponds to a product obtained by simply distilling off the by-product remaining after the epoxy production.
Epoxy production process When heat is applied to the reactor in which the byproduct is injected, distillation occurs actively at a certain temperature, which corresponds to the first stage distillation temperature. As a result of the experiment, the first stage distillation can be carried out at 80 to 90 ° C. Through the first stage distillation, a primary distillate containing IPA and H 2 O is generated. The primary distillate also contains some ECH.
In the pervaporation step (S220), the first distillate is subjected to a pervaporation process to separate water. Through this pervaporation process, the content of water can be lowered to 5 wt% or less, whereby IPA and ECH of high purity can be recovered.
The reason for removing water is that IPA and ECH obtained through pervaporation can be fed back into the reactor as a raw material for producing an epoxy resin. In this case, water causes hydrolysis of the raw material, and the yield of the epoxy resin is lowered Therefore, it is necessary to lower the content as much as possible.
For the pervaporation process in the present invention, a pervaporation membrane comprising a silica separation layer can be used. As a result of the pervaporation process using this silica separation layer, high selectivity for H 2 O was obtained.
FIG. 4 is a schematic view showing a process for producing a pervaporation membrane including a silica separation layer used in the present invention, and FIG. 5 is a view illustrating an example of a process for producing a pervaporation membrane including a silica separation layer.
4 and 5, the illustrated method includes an a-alumina support preparing step (S410), an intermediate layer forming step (S420), and a silica separating layer forming step (S430).
In the step of preparing a-alumina support (S410), a porous a-alumina support is provided.
Next, in the intermediate layer formation step (S420), an intermediate layer is formed on the a-alumina support for surface modification for pore control of the porous a-alumina support.
In the intermediate layer forming step S420 and the silica separating layer forming step S430 described later, the intermediate layer and the silica separating layer can be formed by dipping coating and sintering. In order to increase the layer forming efficiency, Repeat ~ 10 times. In addition, the immersion can be performed for several seconds, and the sintering can be performed at about 550 DEG C for about 30 minutes, and can be performed in an atmospheric environment.
The intermediate layer can be formed as a single layer, preferably a multi-layer, using a silica-zirconia sol in which? -Alumina particles are dispersed. For the formation of the intermediate layer of the multilayer, the silica-zirconia sol in which the? -Alumina particles are dispersed is prepared by, for example, preparing a silica-zirconia sol in an amount of 3 to 4 μm and α- And dispersed by ultrasonic waves for 5 minutes.
Next, in the silica separation layer formation step (S430), a silica separation layer is formed on the intermediate layer. The separation layer coating solution may be a polymeric silica solution. More specifically, a silica sol may be prepared by conducting a hydrolysis-condensation reaction at a temperature of 60 ° C using a hydrochloric acid catalyst, and then the silica sol may be diluted to a concentration of 1.0 wt% and then used for coating.
In the sol-gel method, which is a silica solution preparation method, the hydrolysis rate and the condensation reaction rate differ depending on the pH of the solution. In order to prepare a polymer-type silica solution, a condensation reaction should take place after hydrolysis using an acidic catalyst. This determines the initial rate of hydrolysis. Since the TEOS has to be sufficiently hydrolyzed to prepare the polymer-type silica solution, the concentration of the hydrochloric acid catalyst for accelerating the hydrolysis is preferably 1.0 wt% or more, and more preferably 1.0 to 3.0 wt%. As a result of the experiment, the silica separation layer coating efficiency can be increased and the selectivity can be increased when the concentration of the hydrochloric acid catalyst is 1.5 wt% than that of 0.5 wt%.
In the second distillation step (S230), the residue from which the first-stage distillate has been removed is distilled in two stages at a higher temperature than the first-stage distillation. In this step, ECH is distilled.
As a result of the experiment, the two-stage distillation can be carried out at 105 to 115 ° C.
Next, in the ECH recovery step (S240), ECH is recovered from the two-stage distillate. In this step, the second stage distillate contains 98 wt% or more of ECH. Accordingly, when the epoxy resin raw material is reused, a separate purification process may not be required. In addition, when high purity is required for use in other processes, a separate purification process can be performed.
Example
Hereinafter, the configuration and operation of the present invention will be described in more detail with reference to preferred embodiments of the present invention. It is to be understood, however, that the same is by way of illustration and example only and is not to be construed in a limiting sense. The contents not described here are sufficiently technically inferior to those skilled in the art, and a description thereof will be omitted.
1. Distillation experiment of JT-9 mixture
JT-9, a by-product of the epoxy resin manufacturing process, was poured into a 500 mL flask at a rate of 300 g, and the distillation experiment was conducted by applying heat. As a result of the experiment using JT-9 as a feedstock based on the temperature of the distillation tower, the distillation was first distilled at a temperature of about 80 ° C. for a long period of time, then rapidly increased to about 110 ° C., It showed progress.
The samples were collected before and after distillation, and analyzed by gas chromatography and moisture meter. The results are shown in Table 1 below.
[Table 1] (Unit: wt%)
As a result of analyzing the first stage distillate near 80 ℃ based on the upper temperature of the distillation tower after distillation, the water content was about 15 wt% and IPA was about 51 wt%.
In the two-stage distillation stage, ECH was more than 98 wt% because IPA and H 2 O were removed through one-stage distillation. Therefore, high purity ECH can be purified by removing IPA / H 2 O by one-stage distillation and then using two-stage distillation.
In Table 1, the remaining materials after the two-stage distillation appear to be low-molecular-weight epoxy resins formed by the reaction of ECH at high temperatures.
2. Preparation of a silica separation layer on a porous alumina support
The porous support used in this embodiment is an alumina support of PALL (US) having a diameter of 10 mm and a length of 25 mm and has an average pore size of 1 μm or more. The support was prepared by surface modification using a solution of a-alumina particles dispersed in a porous alumina support and coating the intermediate layer.
The intermediate layer was formed into a multi-layered structure using a silica-zirconia sol in which? -Alumina particles were dispersed.
First,? -Alumina particles having an average particle diameter of about 3 占 퐉 were prepared, put into a silica-zirconia sol at a concentration of 2.0 wt%, and dispersed by ultrasonic wave for 5 minutes. Then, the porous alumina support was immersed in the silica-zirconia sol in which the a-alumina particles were dispersed for about 5 seconds. Thereafter, it was sintered in an atmospheric atmosphere at 550 캜 for 30 minutes. This sintering and immersion was repeated five times.
Then,? -Alumina particles having an average particle diameter of about 150 nm were prepared and put into a silica-zirconia sol at a concentration of 2.0 wt%, and then dispersed by ultrasonic wave for 5 minutes. Then, the porous alumina support was immersed in the silica-zirconia sol in which the a-alumina particles were dispersed for about 5 seconds. Thereafter, it was sintered in an atmospheric atmosphere at 550 캜 for 30 minutes. This immersion and sintering were repeated 5 times.
To form a silica separation layer, a silica solution was prepared from a TEOS solution using 0.5 wt% or 1.5 wt% hydrochloric acid catalyst, and each silica solution prepared was diluted to a concentration of 1.0 wt%.
The support with the intermediate layer was immersed in each diluted silica solution for 5 seconds, then sintered in air atmosphere at 550 캜 for 30 minutes, and dipped and sintered 5 times or 10 times to form a final silica separation layer.
6 and 7 show the results of FE-SEM observation of the surface and cross section of the pervaporation membrane containing the silica separation layer used in the embodiment of the present invention. 7 shows the result of using silica sol prepared with 1.5 wt% hydrochloric acid catalyst. Both sintering temperatures were 550 ℃.
In FIG. 6, it can be seen that the coating is not perfect enough to show the alumina particle layer when the FE-SEM is observed at a high magnification of 5000 times or more. The silica solution was prepared by increasing the concentration of hydrochloric acid catalyst from 0.5 wt% to 1.5 wt% in order to increase the hydrolysis reaction rate so that the silica layer completely covers the alumina / silica - zirconia layer. The prepared silica solution was diluted to 1.0 wt., Coated, and sintered at the same temperature of 550 ° C. to prepare a silica separation layer. In FIG. 7, the low-magnification image shows a rugged surface, but it can be seen that no cracks or pinholes are seen in the 5000-magnified image. The silica separation layer prepared by adjusting the catalyst concentration to 1.5 wt% of HCl appears to be a suitable separation membrane for the present study and the performance was evaluated more specifically through the gas permeation experiment and the pervaporation experiment.
3. Performance evaluation of silica separation layer by pervaporation method
Pervaporation using a silica separation layer was carried out with a pervaporation device with a laboratory scale 1 L feed. The concentrations of feed and permeate were analyzed by gas chromatography. The GC used in the experiment is Agilent's 7890A and the column is Agilent's DB-1 (L .: 50m, D .: 0.320mm).
The silica separating layer prepared with the polymer-type silica solution on the support surface modified with the intermediate layer was pervaporated for 1 to 2 hours at 50 ° C with IPA / H2O = 90/10 (wt% / wt% The results are summarized in Table 2 below. The permeability of the silica coated with 1.0wt% HCl 0.5wt% HCl on the surface - modified support was measured 5 or 10 times for 1 hour or 2 hours. The selectivity was not more than 5. In some cases, the permeation occurs and the feed liquid passes directly to the permeate side, and the selectivity is calculated at around 1.
Isolation layer resulting permeability silica network is a more stable test using a 1.5wt% HCl solution to the separation layer in the solution is 0.6 kg · m -2 · h - was more than 1, the selectivity showed a value of more than 20. When the number of coatings of the separation layer was 5, the selectivity was distributed in the range of 3 to 5, but it was 20 or more when the coating was applied 10 times or more. It has been confirmed that a selective membrane capable of selectively permeating water can be produced at a selectivity value corresponding to the case where the IPA concentration on the permeation side is between 20 and 30 wt%.
It was found that the permeation membranes M-6, M-7 and M-8 produced under the same conditions showed similar reproducibility.
Table 2 shows the experimental results of pervaporation in 85 wt% IPA solution.
[Table 2]
Referring to Table 2, a pervaporation experiment was conducted using a J-9 mixture (16.8 wt% of H 2 O, 34.3 wt% of IPA and 31.3 wt% of ECH) first distilled at 50 ° C using an M-6 separator as a feed solution As a result, the concentration of water on the permeation side was 91.8 wt%, and the concentration of IPA and ECH was 1.0 wt% or less. The overall transmittance was 1.22 kg · m -2 · h -1 and the selectivity was 55.4. The silica separating layer using the surface-modified support is considered to be a separator suitable for removing water from the multi-component JT-9 mixture.
Table 3 shows the area of the M-6 membrane module and the concentration of water at the recovery side according to the change of the pervaporation time.
At this time, the water concentration of the feed mixture was 16.80 wt%.
[Table 3]
Referring to Table 3, it can be seen that the longer the pervaporation time and the larger the module area, the smaller the water concentration. That is, as can be seen from Table 3, the concentration of water in the primary distillate can be lowered to 5% or less by increasing the area of the separation membrane and increasing the pervaporation time.
4. Distillation / Membrane Complex Process Design
Table 1 summarizes the results of the distillation experiments of JT-9 mixed solution of a large amount of unreacted materials and by-products generated in the epoxy resin manufacturing process. In the first distillation, H 2 O is distributed in 13 to 17 wt% In tea distillation, more than 98% of ECH was present.
Therefore, the process of recovering, purifying and reusing ECH / IPA in JT-9 can be designed as follows through distillation and separation membrane experiments.
First, the water contained in the first stage distillation causes the hydrolysis of the raw material in the epoxy resin manufacturing process. Therefore, it is necessary to remove it to 5 wt% or less to increase the number of cycles. Therefore, when distillation takes place in two stages, the first stage distillate is used as the feed liquid, the water is removed through the separation membrane process, and ECH / IPA is recovered and supplied as the epoxy resin raw material.
On the other hand, the second stage distillate can be reused immediately without purification process because the purity of ECH is over 98%. In addition, the purified ECH can be used as a raw material for processes that do not use IPA as a solvent.
While the invention has been described in connection with what is presently considered to be the most practical and preferred embodiment, it is to be understood that the invention is not limited to the disclosed embodiments. Such changes and modifications are intended to fall within the scope of the present invention unless they depart from the scope of the present invention. Accordingly, the scope of the present invention should be determined by the following claims.
Claims (5)
(b) pervaporating the first stage distillate to recover IPA and ECH;
(c) distilling the residue of step (a) in which the first-stage distillate is removed in two stages at 110 to 115 ° C; And
(d) recovering the ECH from the second-stage distillate. < RTI ID = 0.0 > 8. < / RTI >
Wherein the pervaporation membrane comprising a silica separation layer is used in step (b).
The pervaporation membrane
providing an a-alumina support,
Forming an intermediate layer on the a-alumina support,
Forming a silica separation layer on the intermediate layer
And recovering by-product from the epoxy production process.
Wherein the step of forming the silica separation layer comprises preparing a silica sol by using a hydrochloric acid catalyst in an amount of 1.0 to 3.0 wt% to proceed a hydrolysis-condensation reaction of the TEOS precursor By - product recovery method.
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| KR102196707B1 (en) * | 2019-04-12 | 2020-12-30 | 한국화학연구원 | Production process of pervaporation membranes for recovery of by-products from epoxy resin manufacturing process |
| KR102549286B1 (en) * | 2021-03-18 | 2023-06-30 | 한국화학연구원 | Method for Separation and Recovery of By-product in Producing Epoxy Resin |
| CN113248459B (en) * | 2021-06-04 | 2023-03-31 | 江苏扬农化工集团有限公司 | Extraction method of water phase containing epoxy chloropropane |
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| JP2003171437A (en) | 2001-09-28 | 2003-06-20 | Dainippon Ink & Chem Inc | Method for producing epoxy resin |
| JP2010529165A (en) * | 2007-06-12 | 2010-08-26 | ソルヴェイ（ソシエテ アノニム） | Epichlorohydrin, production method and use |
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| JP2003171437A (en) | 2001-09-28 | 2003-06-20 | Dainippon Ink & Chem Inc | Method for producing epoxy resin |
| JP2010529165A (en) * | 2007-06-12 | 2010-08-26 | ソルヴェイ（ソシエテ アノニム） | Epichlorohydrin, production method and use |
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