CN112592255B - Method for removing 3-chloropropene in epoxy chloropropane water layer - Google Patents
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Abstract
The invention aims to provide a method for removing 3-chloropropene from an epichlorohydrin reaction water layer. The method takes an epichlorohydrin reaction water layer as a raw material, takes a molecular sieve as an adsorbent, adsorbs 3-chloropropene therein, recovers the 3-chloropropene by thermal desorption after saturation adsorption, and regenerates the adsorbent. The molecular sieve selected by the invention has excellent adsorption effect on 3-chloropropene, and a reaction water layer after adsorption can be directly rectified to recover methanol.
Description
Technical Field
The invention belongs to the technical field of adsorption separation, and particularly relates to a method for removing 3-chloropropene from an epichlorohydrin reaction water layer.
Background
Epichlorohydrin (ECH) is an organic synthetic intermediate with extremely strong functionality and is mainly used for preparing epoxy resin. At present, the industrial production methods of epichlorohydrin mainly comprise two methods: the chlorohydrin process and the glycerol process. The chlorohydrin process comprises three steps of preparing 3-chloropropene by high-temperature chlorination of propylene, preparing dichloropropanol by hypochlorination of the 3-chloropropene, and synthesizing epichlorohydrin by saponification of the dichloropropanol. The chlorohydrin process has the disadvantages of severe corrosion of equipment and environmental pollution, and produces about 40 tons of salt-containing wastewater per 1 ton of epichlorohydrin. The glycerol method process consists of two steps of chlorination and saponification, the glycerol method has fewer byproducts and mild operation conditions, but the production capacity of the epichlorohydrin is greatly limited by the raw material glycerol. Catalyzing 3-chloropropene and H by adopting titanium silicalite molecular sieve (TS-1) 2 O 2 The method for preparing the epoxy chloropropane by direct epoxidation has the advantages of mild reaction conditions, simple process, high selectivity, less wastewater and the like, and is a green process for producing the epoxy chloropropane.
In the process of synthesizing epichlorohydrin by catalyzing epoxidation of 3-chloropropene by using a titanium silicalite molecular sieve, methanol is used as a solvent and needs to be rectified and recycled, a small amount of 3-chloropropene (0.2-2%) exists in a reaction water layer, and the 3-chloropropene is hydrolyzed or reacts with the methanol to generate impurities in the rectification process, so that the quality of the recovered methanol is influenced, and therefore the 3-chloropropene is removed before the methanol is rectified and recovered. Patent CN201110026568.7 discloses an integrated restoring system for chlorinated hydrocarbon polluted water, which adopts granular activated carbon to adsorb chlorinated hydrocarbon in water, wherein the activated carbon is easy to adsorb to be saturated and difficult to regenerate. Patent CN201210118537.9 reports a treatment method for dichloroethane production wastewater, in which part of chlorinated hydrocarbons are stripped and then discharged after passing through an adsorbent, wherein the adsorbent is activated carbon and macroporous resin. So far, no published report of adsorbing 3-chloropropene in water by using a molecular sieve as an adsorbent is seen.
Disclosure of Invention
The invention aims to provide a method for removing 3-chloropropene from an epichlorohydrin reaction water layer. The method takes an epichlorohydrin reaction water layer (the methanol content is 10-30%, the 3-chloropropene content is 0.2-2%, the epichlorohydrin content is 1-3%, the 1-chloro-3-methoxy-2-propanol content is 0.1-1%, and the balance is water) as a raw material, takes a molecular sieve as an adsorbent to adsorb the 3-chloropropene, recovers the 3-chloropropene by thermal desorption after saturated adsorption, and regenerates the adsorbent. The molecular sieve selected by the invention has excellent adsorption effect on 3-chloropropene, and the reaction water layer after adsorption can be directly rectified to recover methanol.
The technical scheme takes a molecular sieve as an adsorbent to physically adsorb 3-chloropropene in an epoxy chloropropane reaction water layer to remove the 3-chloropropene, and comprises the following steps:
(1) Weighing a certain amount of activated molecular sieve and placing the molecular sieve in an adsorption tube of a fixed bed;
(2) Pumping a reaction water layer by a metering pump under a certain temperature condition, setting a sampling point at an outlet of a fixed bed, periodically detecting the content of 3-chloropropene in the adsorbed reaction water layer, when the content is more than or equal to 0.05 percent, introducing the reaction water layer to be treated into another adsorption tube filled with an activated molecular sieve for continuous adsorption, desorbing the adsorption tube with saturated adsorption at high temperature by using air, nitrogen or other inert gases, collecting condensate by using a condensing tube after desorption, and recovering the 3-chloropropene.
The adsorbent is naturally formed or artificially prepared aluminosilicate with a specific three-dimensional pore structure or a layered structure, and comprises an A-type molecular sieve, an X-type molecular sieve, a Y-type molecular sieve, a ZSM-5 molecular sieve, mordenite, pillared montmorillonite and the like.
The effective aperture of the A-type molecular sieve is 0.3-1.5nm; the effective aperture of the Y-shaped molecular sieve is 0.7-1.6nm, and the Y-shaped molecular sieve is provided with a super cage with the aperture of 1.0-2.0nm; the effective aperture of the X-type molecular sieve is 1.0-2.0nm; the effective aperture of the ZSM-5 molecular sieve is 0.5-1.2nm; the effective aperture of the mordenite is 0.3-1.0nm; the effective aperture of the pillared montmorillonite is 2.0-4.0nm.
The adsorption separation temperature is 0-60 ℃, preferably 10-30 ℃;
the adsorption separation pressure is 0.1-1MPa, preferably 0.2-0.6MPa;
the space velocity of the adsorption separation volume is 0.5-5h -1 Preferably 1-4h -1 ；
The desorption separation temperature is 120-260 ℃, and preferably 140-200 ℃;
the space velocity of the desorption separation volume is 0.1-1h -1 Preferably 0.2 to 0.8h -1 。
The invention has the following advantages:
(1) The molecular sieve has obvious adsorption effect and can remove 3-chloropropene from an aqueous solution containing organic matters such as methanol, epichlorohydrin and the like; by utilizing the special electrostatic force of the 3-chloropropene, a proper adsorbent is screened out through a large number of experiments, and different pore diameters are designed to further realize the adsorption of the 3-chloropropene in the epoxy chloropropane reaction water layer.
(2) After 3-chloropropene is removed from the water layer, the content of recovered methanol is more than 99.5 percent;
(3) After the adsorbent is regenerated, the adsorbent still has remarkable adsorption effect on 3-chloropropene.
The particularity of the invention lies in the structure of the molecular sieve adsorbent, and the different silicon-aluminum ratios, different balancing cations and stronger electrostatic field determine that the molecular sieve adsorbent keeps higher adsorption capacity on the adsorbate, particularly 3-chloropropene under the condition of low-concentration adsorption. After the molecular sieve is activated at high temperature and loses crystal water, a plurality of holes are formed in the crystal, the size of the hole diameter is similar to the diameter of 3-chloropropene, the hole diameter is very uniform, different substance molecules are adsorbed or rejected according to the size of the hole in the crystal, and meanwhile, the specific adsorption of the 3-chloropropene is determined according to the polarity or the polarizability of the 3-chloropropene molecules, so that the separation effect is achieved.
Drawings
FIG. 1 is a diagram of an adsorption device for an epichlorohydrin reaction water layer.
Detailed Description
The following examples are only intended to illustrate the technical solution of the present invention, but the scope of the present invention is not limited thereto:
example 1
Loading activated adsorbent (5A type molecular sieve with effective pore diameter of 0.6 nm) into 1L fixed bed adsorption tube, and separating at 40 deg.CThe pressure is 0.4MPa, the volume space velocity is 1h -1 Under the condition of (1), inputting an epichlorohydrin reaction water layer (the content of 3-chloropropene is 0.5%) to the top end of an adsorption tube by using a metering pump, obtaining an adsorbed water layer from the bottom, quantitatively analyzing that the content of 3-chloropropene is 0-0.05%, and the adsorption rate of a 5A type molecular sieve on 3-chloropropene>95 percent. When the content of 3-chloropropene is detected to be more than or equal to 0.05 percent, the adsorption tube is considered to be penetrated, then a reaction water layer to be treated is introduced into another adsorption tube filled with the activated molecular sieve for continuous adsorption, the adsorption tube with saturated adsorption is desorbed by air at the temperature of 120 ℃, wherein the volume space velocity is 0.1h -1 And collecting condensate by using a condensing tube after desorption, and recovering the 3-chloropropene (99.3%).
Example 2
Loading activated adsorbent (3A type molecular sieve with effective pore diameter of 0.3 nm) into 1L fixed bed adsorption tube, and adsorbing at 30 deg.C under 0.1MPa and volume space velocity of 0.5h -1 Under the condition of (1), inputting an epichlorohydrin reaction water layer (the content of 3-chloropropene is 0.2%) to the top end of an adsorption tube by using a metering pump, obtaining an adsorbed water layer from the bottom, quantitatively analyzing that the content of 3-chloropropene is 0-0.05%, and the adsorption rate of a 3A type molecular sieve on 3-chloropropene>95 percent. When the content of 3-chloropropene is detected to be more than or equal to 0.05 percent, the adsorption tube is considered to be penetrated, then a reaction water layer to be treated is introduced into another adsorption tube filled with the activated molecular sieve for continuous adsorption, the adsorption tube with saturated adsorption is desorbed by air at the temperature of 140 ℃, wherein the volume space velocity is 0.2h -1 And collecting condensate by using a condensing tube after desorption, and recovering the 3-chloropropene (99.4%).
Example 3
Loading activated adsorbent (4A type molecular sieve with effective pore diameter of 0.4 nm) into 1L fixed bed adsorption tube, and adsorbing at 50 deg.C under 0.2MPa and volume space velocity of 2h -1 Under the condition of (1), inputting an epichlorohydrin reaction water layer (the content of 3-chloropropene is 0.6%) to the top end of the adsorption tube by using a metering pump, obtaining an adsorbed water layer from the bottom, quantitatively analyzing that the content of 3-chloropropene is 0-0.05%, and the adsorption rate of a 4A type molecular sieve on 3-chloropropene>96 percent. When the content of 3-chloropropene is detected to be more than or equal toWhen the concentration is 0.05%, the adsorption tube is penetrated, then the reaction water layer to be treated is introduced into another adsorption tube filled with activated molecular sieve for continuous adsorption, the adsorption tube with saturated adsorption is desorbed by argon gas under the condition of 160 ℃, wherein the volume space velocity is 0.3h -1 And after desorption, a condensate is collected by a condensing tube, and 3-chloropropene (99.4%) is recovered.
Example 4
Loading activated adsorbent (13X type molecular sieve with effective pore diameter of 1.3 nm) into 1L fixed bed adsorption tube, and adsorbing at 60 deg.C under 0.3MPa and volume space velocity of 3 hr -1 Under the condition of (1%) introducing epoxy chloropropane reaction water layer (3-chloropropene content is 1%) into top end of adsorption tube by using metering pump, obtaining adsorbed water layer from bottom, quantitatively analyzing that 3-chloropropene content is 0-0.05%, and adsorption rate of 13X type molecular sieve to 3-chloropropene>96 percent. When the content of 3-chloropropene is detected to be more than or equal to 0.05 percent, the adsorption tube is considered to be penetrated, then a reaction water layer to be treated is introduced into another adsorption tube filled with the activated molecular sieve for continuous adsorption, the adsorption tube with saturated adsorption is desorbed by air at 180 ℃, wherein the volume space velocity is 0.4h -1 And collecting condensate by using a condensing tube after desorption, and recovering the 3-chloropropene (99.5%).
Example 5
Loading activated adsorbent (10X type molecular sieve with effective pore diameter of 1.0 nm) into 1L fixed bed adsorption tube, and adsorbing at 80 deg.C under 0.6MPa and 4 hr at volume space velocity -1 Under the condition of (1.4%) of epoxy chloropropane reaction water layer is fed into top end of adsorption tube by using metering pump, and the adsorbed water layer is obtained from bottom portion, and the 3-chloropropene content is 0-0.01%, and the adsorption rate of 10X type molecular sieve to 3-chloropropene is quantitatively analyzed>96 percent. When the content of 3-chloropropene is detected to be more than or equal to 0.05 percent, the adsorption tube is considered to be penetrated, then a reaction water layer to be treated is introduced into another adsorption tube filled with the activated molecular sieve for continuous adsorption, the adsorption tube with saturated adsorption is desorbed by nitrogen at the temperature of 200 ℃, wherein the volume space velocity is 0.6h -1 And collecting condensate by using a condensing tube after desorption, and recovering the 3-chloropropene (99.6%).
Example 6
Loading activated adsorbent (NaY type molecular sieve with effective pore diameter of 0.8 nm) into 1L fixed bed adsorption tube, and adsorbing at 100 deg.C under 0.8MPa and volume space velocity of 5 hr -1 Under the condition of (1), using a metering pump to feed an epichlorohydrin reaction water layer (3-chloropropene content is 1.6%) into the top end of an adsorption tube, obtaining an adsorbed water layer from the bottom, quantitatively analyzing that the 3-chloropropene content is 0-0.05%, and removing rate of 3-chloropropene by using a NaY type molecular sieve>97 percent. When the content of 3-chloropropene is detected to be more than or equal to 0.05 percent, the adsorption tube is considered to be penetrated, then a reaction water layer to be treated is introduced into another adsorption tube filled with the activated molecular sieve for continuous adsorption, the adsorption tube with saturated adsorption is desorbed by nitrogen at the temperature of 220 ℃, wherein the volume space velocity is 0.8h -1 And collecting condensate by using a condensing tube after desorption, and recovering the 3-chloropropene (99.6%).
Example 7
Loading activated adsorbent (ZSM-5 molecular sieve with effective pore diameter of 0.9 nm) into 1L fixed bed adsorption tube, and adsorbing at 60 deg.C under 1MPa and 3 hr at volume space velocity -1 Under the conditions of (1), introducing an epichlorohydrin reaction water layer (with 3-chloropropene content of 1.8%) to the top end of the adsorption tube by using a metering pump, obtaining an adsorbed water layer from the bottom, quantitatively analyzing that the 3-chloropropene content is 0-0.05%, and the removal rate of 3-chloropropene by using a ZSM-5 molecular sieve>97 percent. When the content of 3-chloropropene is detected to be more than or equal to 0.05 percent, the adsorption tube is considered to be penetrated, then a reaction water layer to be treated is introduced into another adsorption tube filled with the activated molecular sieve for continuous adsorption, the adsorption tube with saturated adsorption is desorbed by air at the temperature of 240 ℃, wherein the volume space velocity is 1h -1 And collecting condensate by using a condensing tube after desorption, and recovering the 3-chloropropene (99.6%).
Example 8
Loading activated adsorbent (mordenite with effective pore diameter of 0.6 nm) into 1L fixed bed adsorption tube, and adsorbing at 40 deg.C under 0.8MPa and 3h at a volume space velocity -1 Under the condition of (1), feeding epoxy to the top end of the adsorption tube by using a metering pumpChloropropane reaction water layer (3-chloropropene content is 2%), obtaining adsorbed water layer from bottom, quantitatively analyzing 3-chloropropene content at 0-0.05%, and removing 3-chloropropene by mordenite>97 percent. When the content of 3-chloropropene is detected to be more than or equal to 0.05 percent, the adsorption tube is considered to be penetrated, then a reaction water layer to be treated is introduced into another adsorption tube filled with an activated molecular sieve for continuous adsorption, the adsorption tube with saturated adsorption is desorbed by air at the temperature of 260 ℃, wherein the volume space velocity is 1h -1 And collecting condensate by using a condensing tube after desorption, and recovering the 3-chloropropene (99.5%).
Example 9
Loading activated adsorbent (pillared montmorillonite with effective pore diameter of 3 nm) into 1L fixed bed adsorption tube, and adsorbing at 40 deg.C under 0.6MPa and at a volume space velocity of 2 hr -1 Under the conditions of (1%) introducing epoxy chloropropane reaction water layer (3-chloropropene content is 1%) into top end of adsorption tube by using metering pump, obtaining adsorbed water layer from bottom, quantitatively analyzing that 3-chloropropene content is 0-0.05%, and removing rate of 3-chloropropene by pillared montmorillonite>95 percent. When the content of 3-chloropropene is detected to be more than or equal to 0.05 percent, the adsorption tube is considered to be penetrated, then a reaction water layer to be treated is introduced into another adsorption tube filled with the activated molecular sieve for continuous adsorption, the adsorption tube with saturated adsorption is desorbed by air at the temperature of 240 ℃, wherein the volume space velocity is 0.8h -1 And collecting condensate by using a condensing tube after desorption, and recovering the 3-chloropropene (99.5%).
Examples 10 to 18
The adsorption capacity of the regenerated molecular sieve on 3-chloropropene in the reaction water layer was examined, the method and experimental conditions were the same as those in example 3, and the results are shown in the following table.
| Example numbering | Molecular sieve type | 3-chloropropene adsorption (%) |
| 10 | 5A type molecular sieve | >95 |
| 11 | 3A type molecular sieve | >95 |
| 12 | 4A type molecular sieve | >96 |
| 13 | 13X type molecular sieve | >96 |
| 14 | 10X type molecular sieve | >96 |
| 15 | NaY type molecular sieve | >97 |
| 16 | ZSM-5 molecular sieve | >96 |
| 17 | Mordenite zeolite | >94 |
| 18 | Pillared montmorillonite | >95 |
Comparative example 1
Loading activated adsorbent (MCH-41) into 1L fixed bed adsorption tube, and separating at 40 deg.C under 0.8MPa and 3 hr -1 Under the condition, an epichlorohydrin reaction water layer (the chloropropene content is 2%) is input to the top end of the adsorption tube by a metering pump, an adsorbed water layer is obtained from the bottom, the AC content in the adsorbed epichlorohydrin reaction water layer is quantitatively analyzed to be 1.7-2.0%, and MCH-41 has no adsorption effect on chloropropene in the epichlorohydrin reaction water layer.
Comparative example 2
Loading activated adsorbent (ZSM-14) into 1L fixed bed adsorption tube, and adsorbing at 30 deg.C under 0.8MPa and 2 hr at a volume space velocity -1 Under the condition of (1), inputting an epichlorohydrin reaction water layer (the chloropropene content is 2%) to the top end of the adsorption tube by using a metering pump, obtaining an adsorbed water layer from the bottom, quantitatively analyzing that the AC content in the adsorbed epichlorohydrin reaction water layer is 1.0-1.8%, and the removal rate of chloropropene by using a ZSM-14 type molecular sieve is 56%.
Comparative example 3
Loading activated adsorbent (VPI-5) into 1L fixed bed adsorption tube, and adsorbing at 50 deg.C under 0.3MPa and 3 hr at volume space velocity -1 Under the condition of (1), inputting an epichlorohydrin reaction water layer (the chloropropene content is 2%) to the top end of the adsorption tube by using a metering pump, obtaining an adsorbed water layer from the bottom, quantitatively analyzing that the AC content in the adsorbed epichlorohydrin reaction water layer is 1.2-1.7%, and the removal rate of chloropropene by using a VPI-5 type molecular sieve is 48%.
Claims (12)
1. A method for removing 3-chloropropene from an epichlorohydrin reaction water layer is characterized by comprising the following steps:
(1) Weighing a certain amount of activated molecular sieve and placing the molecular sieve in an adsorption tube of a fixed bed;
(2) Pumping an epichlorohydrin reaction water layer by using a metering pump under the conditions of certain temperature and pressure, arranging a sampling point at an outlet of a fixed bed, periodically detecting the content of 3-chloropropene in the adsorbed reaction water layer, introducing the reaction water layer to be treated into another adsorption tube filled with an activated adsorbent to continuously adsorb when the content is more than or equal to 0.05%, desorbing the adsorption tube with saturated adsorption at high temperature by using air, nitrogen or other inert gases, collecting condensate by using a condenser tube after desorption, and recovering the 3-chloropropene, wherein the adsorbent is an A-type molecular sieve, an X-type molecular sieve, a Y-type molecular sieve, a ZSM-5 molecular sieve, mordenite or pillared montmorillonite, and the effective pore diameter of the A-type molecular sieve is 0.3-1.5nm; the effective aperture of the Y-shaped molecular sieve is 0.7-1.6nm, and the Y-shaped molecular sieve is provided with a super cage with the aperture of 1.0-2.0nm; the effective aperture of the X-type molecular sieve is 1.0-2.0nm; the effective aperture of the ZSM-5 molecular sieve is 0.5-1.2nm; the effective aperture of the mordenite is 0.3-1.0nm; the effective aperture of the pillared montmorillonite is 2.0-4.0nm.
2. The process for removing 3-chloropropene from an epichlorohydrin reaction water layer according to claim 1, characterized in that the adsorption separation temperature is 0-60 ℃.
3. The process for removing 3-chloropropene from an aqueous epichlorohydrin reaction layer according to claim 2, wherein the adsorption separation temperature is 10-30 ℃.
4. The process for removing 3-chloropropene from an epichlorohydrin reaction water layer according to claim 1, characterized in that the adsorption separation pressure is 0.1-1MPa.
5. The process for removing 3-chloropropene from an aqueous epichlorohydrin reaction layer according to claim 4, wherein the adsorption separation pressure is 0.2-0.6MPa.
6. A process of manufacture of epichlorohydrin according to claim 1The method for removing 3-chloropropene from a reaction water layer is characterized in that the space velocity of the adsorption separation volume is 0.5-5h -1 。
7. The method for removing 3-chloropropene from an epichlorohydrin reaction water layer according to claim 6, wherein the adsorption separation volume space velocity is 1-4h -1 。
8. The process for removing 3-chloropropene from an aqueous epichlorohydrin reaction layer according to claim 1, wherein the desorption separation temperature is 120-260 ℃.
9. The process for removing 3-chloropropene from an aqueous epichlorohydrin reaction layer according to claim 8, wherein the desorption separation temperature is 140-200 ℃.
10. The method for removing 3-chloropropene from an epichlorohydrin reaction water layer according to claim 1, wherein the desorption separation volume space velocity is 0.1-1h -1 。
11. The method for removing 3-chloropropene from an epichlorohydrin reaction water layer according to claim 10, wherein the desorption separation volume space velocity is 0.2-0.8h -1 。
12. The method for removing 3-chloropropene from an epichlorohydrin reaction water layer according to claim 1, wherein the epichlorohydrin reaction water layer contains 10-30% of methanol, 0.2-2% of 3-chloropropene, 1-3% of epichlorohydrin, 0.1-1% of 1-chloro-3-methoxy-2-propanol and the balance of water.
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| CN111960921A (en) * | 2020-09-09 | 2020-11-20 | 江苏扬农化工集团有限公司 | Method and device for recovering chloropropene and methanol from epoxy chloropropane process water layer by hydrogen peroxide method |
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| CN86108612A (en) * | 1985-12-27 | 1987-09-23 | 埃克森化学专利公司 | From hydrocarbon solvent, remove Organohalogen compounds |
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| CN108129256A (en) * | 2017-12-29 | 2018-06-08 | 山东华安新材料有限公司 | The method that alkenyl halide impurity is detached from the chloro- 1,1,1,2- tetrafluoropropanes of 2- |
| CN111960921A (en) * | 2020-09-09 | 2020-11-20 | 江苏扬农化工集团有限公司 | Method and device for recovering chloropropene and methanol from epoxy chloropropane process water layer by hydrogen peroxide method |
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