CN115926031B - Method for preparing hydrogenated petroleum resin - Google Patents
Method for preparing hydrogenated petroleum resin Download PDFInfo
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- CN115926031B CN115926031B CN202211544451.2A CN202211544451A CN115926031B CN 115926031 B CN115926031 B CN 115926031B CN 202211544451 A CN202211544451 A CN 202211544451A CN 115926031 B CN115926031 B CN 115926031B
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- 229920005989 resin Polymers 0.000 title claims abstract description 126
- 239000011347 resin Substances 0.000 title claims abstract description 126
- 239000003208 petroleum Substances 0.000 title claims abstract description 113
- 238000000034 method Methods 0.000 title claims abstract description 11
- 239000011259 mixed solution Substances 0.000 claims abstract description 30
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 26
- 239000007788 liquid Substances 0.000 claims abstract description 17
- 239000002245 particle Substances 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims description 21
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 238000005984 hydrogenation reaction Methods 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 230000035484 reaction time Effects 0.000 claims description 10
- 238000001704 evaporation Methods 0.000 claims description 6
- 230000008020 evaporation Effects 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 abstract description 8
- 239000000243 solution Substances 0.000 abstract description 6
- 229920000642 polymer Polymers 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000002952 polymeric resin Substances 0.000 description 7
- 229920003002 synthetic resin Polymers 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical class 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XPVIQPQOGTVMSU-UHFFFAOYSA-N (4-acetamidophenyl)arsenic Chemical compound CC(=O)NC1=CC=C([As])C=C1 XPVIQPQOGTVMSU-UHFFFAOYSA-N 0.000 description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
- 229920013640 amorphous poly alpha olefin Polymers 0.000 description 3
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004262 Ethyl gallate Substances 0.000 description 1
- ULFUTCYGWMQVIO-PCVRPHSVSA-N [(6s,8r,9s,10r,13s,14s,17r)-17-acetyl-6,10,13-trimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-yl] acetate;[(8r,9s,13s,14s,17s)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] pentano Chemical compound C1CC2=CC(O)=CC=C2[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCC)[C@@]1(C)CC2.C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 ULFUTCYGWMQVIO-PCVRPHSVSA-N 0.000 description 1
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
The invention discloses a method for preparing hydrogenated petroleum resin, which comprises the following steps: preparing petroleum resin polymer solution a; and a second step of: separating the petroleum resin polymerization liquid a to obtain petroleum resin mixed liquid c; and a third step of: separating the petroleum resin mixed solution c to obtain polymerized petroleum resin d; fourth step: preparing hydrogenated petroleum resin mixed solution e; fifth step: separating the hydrogenated petroleum resin mixed solution e to obtain hydrogenated petroleum resin mixed solution g; sixth step: separating the hydrogenated petroleum resin mixed solution g to obtain hydrogenated petroleum resin h; seventh step: hydrogenated petroleum resin particles are prepared. The hydrogenated petroleum resin prepared by the preparation method has good compatibility, and the hydrogenated petroleum resin with proper softening point and melt viscosity can be obtained through corresponding raw material formula, operation condition and two-step desolventizing and steam stripping, so that the catalyst consumption is reduced, and the properties of chromaticity, wax fog point, compatibility and the like of the hydrogenated petroleum resin are obviously improved.
Description
Technical Field
The invention relates to the field of petroleum resin modification, in particular to a method for preparing hydrogenated petroleum resin.
Background
The petroleum resin is named as petroleum derivative, and has the features of low acid value, high miscibility, high water resistance, high alcohol resistance, high chemical resistance, high acid and alkali resistance, high viscosity regulation and high heat stability.
The petroleum resin can be well compatible with other compounds after being prepared by modification, but the existing petroleum resin can not be well compatible with EVA, IR, APAO, rosin, wax, SBS and SIS after being modified, so that the existing petroleum resin can not realize multiple purposes, the softening point and the melt viscosity of the existing petroleum resin are properly adjusted to be troublesome, more catalysts are needed to be consumed when the existing petroleum resin is compatible with other substances, and the waste of the catalysts is caused.
Disclosure of Invention
The invention aims to provide a method for preparing hydrogenated petroleum resin, which aims to solve the problems in the background technology.
In order to achieve the above purpose, the present invention provides the following technical solutions: a process for the preparation of hydrogenated petroleum resins, said process comprising the steps of;
the first step: preparing petroleum resin polymerization liquid a, namely adding dicyclopentadiene and an organic solvent into a reaction kettle through a metering pump, and carrying out polymerization under a pressurized condition;
and a second step of: separating the petroleum resin polymerization liquid a, and separating the petroleum resin polymerization liquid a obtained in the first step by a flash evaporation desolventizing tower to obtain an organic solvent b and petroleum resin mixed liquid c after separation;
and a third step of: separating the petroleum resin mixed solution c, and separating the petroleum resin mixed solution c obtained in the second step through a superheated steam stripping tower to obtain a polymerized oligomer and polymerized petroleum resin d after separation;
fourth step: preparing hydrogenated petroleum resin mixed solution e, namely adding the polymerized petroleum resin d obtained in the third step and an organic solvent into a hydrogenation reaction kettle through a metering pump, and then adding a nickel catalyst accounting for 1-5% of the mass of the polymerized petroleum resin to prepare hydrogenated petroleum resin mixed solution e;
fifth step: separating the hydrogenated petroleum resin mixed solution e, and separating the hydrogenated petroleum resin mixed solution e obtained in the fourth step through a flash evaporation desolventizing tower to obtain an organic solvent f and a hydrogenated petroleum resin mixed solution g;
sixth step: separating hydrogenated petroleum resin mixed liquor g, and separating the hydrogenated petroleum resin mixed liquor g obtained in the fifth step through a superheated steam stripping tower to obtain hydrogenated oligomer and hydrogenated petroleum resin h;
seventh step: preparing hydrogenated petroleum resin particles, and granulating the hydrogenated petroleum resin h obtained in the sixth step to obtain the hydrogenated petroleum resin particles.
Preferably, the dicyclopentadiene accounts for 84-85%, and the mass ratio of dicyclopentadiene to the organic solvent is 3: 7-6: 4, the pressure of the polymerization reaction is 1-4MPa, the reaction temperature is 220-280 and the reaction time is 150-300 min.
Preferably, the production temperature of the flash desolventizing tower in the second step is set to 150-190 at the top of the tower and 210-230 at the bottom of the tower.
Preferably, the production temperature of the superheated steam stripper in the third step is set to 190-210 at the top and 220-250 at the bottom.
Preferably, the mass ratio of the reaction of the polymerized petroleum resin d and the organic solvent is 3: 7-6: 4, the reaction condition of the hydrogenation reaction kettle is that the hydrogen pressure is 3-8MPa and the mass airspeed is 2-10 hr -1 The reaction temperature is 220-270 and the reaction time is 150-300 min.
Preferably, the production temperature of the flash desolventizing tower in the fifth step is set to be 150-190 at the top of the tower and 210-230 at the bottom of the tower.
Preferably, the production temperature of the superheated steam stripper in the sixth step is set to 190-210 at the top and 220-250 at the bottom.
The invention has the technical effects and advantages that:
the hydrogenated petroleum resin obtained through seven steps of preparation operation is a polymer with lower molecular weight and polymer dispersibility index, so the hydrogenated petroleum resin prepared by the preparation method has good compatibility with EVA, IR, APAO, rosin, wax, SBS and SIS, the hydrogenated petroleum resin with proper softening point and melt viscosity can be obtained through corresponding raw material formula, operation condition and two steps of desolventizing and steam stripping, the molecular weight is more concentrated, the catalyst consumption is reduced, and the chromaticity, wax fog point, compatibility and other performances of the hydrogenated petroleum resin are obviously improved.
Drawings
FIG. 1 is a flow chart of the operational steps of the present invention.
Fig. 2 is a process flow diagram of the present invention.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The invention provides a method for preparing hydrogenated petroleum resin, which is shown in figures 1-2, and comprises the following steps of;
the first step: preparing petroleum resin polymerization liquid a, namely adding dicyclopentadiene and an organic solvent into a reaction kettle through a metering pump, and carrying out polymerization under a pressurized condition;
the dicyclopentadiene accounts for 84-85%, and the mass ratio of dicyclopentadiene to organic solvent is 3: 7-6: 4, the pressure of the polymerization reaction is 1-4MPa, the reaction temperature is 220-280 and the reaction time is 150-300 min.
And a second step of: separating the petroleum resin polymerization liquid a, and separating the petroleum resin polymerization liquid a obtained in the first step by a flash evaporation desolventizing tower to obtain an organic solvent b and petroleum resin mixed liquid c after separation;
the production temperature of the flash desolventizing tower in the second step is set to be 150-190 at the top of the tower and 210-230 at the bottom of the tower.
And a third step of: separating the petroleum resin mixed solution c, and separating the petroleum resin mixed solution c obtained in the second step through a superheated steam stripping tower to obtain a polymerized oligomer and polymerized petroleum resin d after separation;
the production temperature of the superheated steam stripping column in the third step is set to be 190-210 at the top of the column and 220-250 at the bottom of the column.
Fourth step: preparing hydrogenated petroleum resin mixed solution e, namely adding the polymerized petroleum resin d obtained in the third step and an organic solvent into a hydrogenation reaction kettle through a metering pump, and then adding a nickel catalyst accounting for 1-5% of the mass of the polymerized petroleum resin to prepare hydrogenated petroleum resin mixed solution e;
the mass ratio of the polymerized petroleum resin d to the organic solvent is 3: 7-6: 4, the reaction condition of the hydrogenation reaction kettle is that the hydrogen pressure is 3-8MPa and the mass airspeed is 2-10 hr -1 The reaction temperature is 220-270 and the reaction time is 150-300 min.
Fifth step: separating the hydrogenated petroleum resin mixed solution e, and separating the hydrogenated petroleum resin mixed solution e obtained in the fourth step through a flash evaporation desolventizing tower to obtain an organic solvent f and a hydrogenated petroleum resin mixed solution g;
the production temperature of the flash desolventizing tower in the fifth step is set to be 150-190 at the top of the tower and 210-230 at the bottom of the tower.
Sixth step: separating hydrogenated petroleum resin mixed liquor g, and separating the hydrogenated petroleum resin mixed liquor g obtained in the fifth step through a superheated steam stripping tower to obtain hydrogenated oligomer and hydrogenated petroleum resin h;
the production temperature of the superheated steam stripping column in the sixth step is set to 190-210 at the top and 220-250 at the bottom.
Seventh step: preparing hydrogenated petroleum resin particles, and granulating the hydrogenated petroleum resin h obtained in the sixth step to obtain the hydrogenated petroleum resin particles.
In the first embodiment, the softening point of the resin is measured according to GB/T2294-2019, the melt viscosity of the resin is measured according to ASTM D2336 by using a Brinell rotary viscometer at 200 , the bromine number is analyzed according to GB/T24138-2009, the color of the resin is measured according to ASTM E313, the molecular weight distribution index (mw, mn, pd) of the resin product is measured by using a gel chromatography, the insoluble content in the resin is measured, the wax haze point of the hydrogenated petroleum resin of the dicyclopentadiene is measured according to Q/LMXT101-2021, and the resin compatibility is measured according to Q/LMXT 103-2021;
the main components of the raw material dicyclopentadiene are shown in table 1;
| project | Unit (B) | Measured data | Remarks |
| Appearance of | - | No mechanical impurity, transparent liquid | |
| Platinum-cobalt chromaticity | (m/m) | 50 | |
| Cyclopentadiene | (m/m) | 1.14 | |
| Benzene | (m/m) | 0.01 | |
| Toluene (toluene) | (m/m) | 0.16 | |
| Dicyclopentadiene | (m/m) | 85.18 | |
| Light component with six carbon atoms and less than six carbon atoms | (m/m) | 0.52 | |
| More than ten carbon components | (m/m) | 0.15 | |
| Water content | (m/m) | 0.01 |
TABLE 1
Example two, m hydrogenated carbon nine solvent: m dicyclopentadiene 1:1, carrying out hydrogenation reaction on the prepared polymer resin without desolventizing and stripping under the pressure of 1-4MPa, the reaction temperature of 220-280 and the reaction time of 150-300 mi to obtain hydrogenated resin h.
Example three, m hydrogenated carbon nine solvent: m dicyclopentadiene 6:4, carrying out hydrogenation reaction on the prepared polymer resin without desolventizing and stripping under the pressure of 1-4MPa, the reaction temperature of 220-280 and the reaction time of 150-300 mi to obtain hydrogenated resin h.
Example four, m hydrogenated carbon nine solvent: m dicyclopentadiene is 1:1, under the pressure of 1-4MPa, the reaction temperature of 220-280 and the reaction time of 150-300 mi, the prepared polymer resin liquid is desolventized and stripped to obtain polymer resin, and then hydrogenation reaction is carried out to obtain hydrogenated resin h.
Example five, m hydrogenated carbon nine solvent: m dicyclopentadiene in the ratio of 6 to 4, under the pressure of 1-4MPa, the reaction temperature of 220-280 and the reaction time of 150-300 mi, the prepared polymer resin liquid is desolventized and stripped to obtain polymer resin, and then hydrogenation reaction is carried out to obtain hydrogenated resin h.
Wherein, the catalyst is applied mechanically and is always in the hydrogenation reaction kettle after the catalyst is added, and the catalyst is not discharged, and the same batch of equal amount of polymeric resin hydrogenation reaction is repeatedly carried out.
The molecular weight and polymer dispersibility index comparisons of hydrogenated resins h prepared in examples two, three, four and five are shown in Table 2;
TABLE 2
The catalyst consumption, the application times and the bromine number comparison of the hydrogenated resins prepared in the second, third, fourth and fifth examples are shown in Table 3;
TABLE 3 Table 3
Hydrogenated resin wax foggy spots prepared in examples two, three, four and five, and compatibility comparisons with EVA, IR, APAO, rosin, wax, SBS and SIS are shown in Table 4;
TABLE 4 Table 4
Note that: the second and fourth embodiments operate as follows;
1) Adding dicyclopentadiene and an organic solvent into a polymerization reaction kettle to perform polymerization reaction to obtain petroleum resin polymerization solution a;
2) Adding the petroleum resin polymerization solution a obtained in the step 1) into a hydrogenation reaction kettle, adding a nickel catalyst and hydrogen, and carrying out hydrogenation reaction under corresponding conditions to obtain hydrogenated petroleum resin mixed solution e;
3) And (3) desolventizing and stripping the hydrogenated petroleum resin mixed solution e obtained in the step (2) to obtain hydrogenated petroleum resin h.
The third and fifth embodiments operate as follows;
1) Adding dicyclopentadiene and an organic solvent into a polymerization reaction kettle to perform polymerization reaction to obtain petroleum resin polymerization solution a;
2) The petroleum resin polymerization solution a obtained in the step 1) is desolventized and stripped to obtain a polymerization oligomer and a polymerization petroleum resin d;
3) Adding the polymerized petroleum resin d obtained in the step 2) and an organic solvent into a hydrogenation reaction kettle according to a proportion, and carrying out hydrogenation reaction under corresponding conditions in the presence of a nickel catalyst and hydrogen to obtain a hydrogenated petroleum resin mixed solution e;
4) And (3) desolventizing and stripping the hydrogenated petroleum resin mixed solution e obtained in the step (3) to obtain hydrogenated petroleum resin h.
Finally, it should be noted that: the foregoing description is only illustrative of the preferred embodiments of the present invention, and although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that modifications may be made to the embodiments described, or equivalents may be substituted for elements thereof, and any modifications, equivalents, improvements or changes may be made without departing from the spirit and principles of the present invention.
Claims (5)
1. A method for preparing hydrogenated petroleum resin, which is characterized by comprising the following steps of;
the first step: preparing petroleum resin polymerization liquid a, namely adding dicyclopentadiene and an organic solvent into a reaction kettle through a metering pump, and carrying out polymerization under a pressurized condition;
and a second step of: separating the petroleum resin polymerization liquid a, and separating the petroleum resin polymerization liquid a obtained in the first step by a flash evaporation desolventizing tower to obtain an organic solvent b and petroleum resin mixed liquid c after separation;
and a third step of: separating the petroleum resin mixed solution c, and separating the petroleum resin mixed solution c obtained in the second step through a superheated steam stripping tower to obtain a polymerized oligomer and polymerized petroleum resin d after separation;
fourth step: preparing hydrogenated petroleum resin mixed solution e, namely adding the polymerized petroleum resin d obtained in the third step and an organic solvent into a hydrogenation reaction kettle through a metering pump, and then adding a nickel catalyst accounting for 1-5% of the mass of the polymerized petroleum resin to prepare hydrogenated petroleum resin mixed solution e;
fifth step: separating the hydrogenated petroleum resin mixed solution e, and separating the hydrogenated petroleum resin mixed solution e obtained in the fourth step through a flash evaporation desolventizing tower to obtain an organic solvent f and a hydrogenated petroleum resin mixed solution g;
sixth step: separating hydrogenated petroleum resin mixed liquor g, and separating the hydrogenated petroleum resin mixed liquor g obtained in the fifth step through a superheated steam stripping tower to obtain hydrogenated oligomer and hydrogenated petroleum resin h;
seventh step: preparing hydrogenated petroleum resin particles, and granulating the hydrogenated petroleum resin h obtained in the sixth step to obtain hydrogenated petroleum resin particles;
the dicyclopentadiene accounts for 84-85%, and the mass ratio of dicyclopentadiene to organic solvent is 3: 7-6: 4, the pressure of the polymerization reaction is 1-4MPa, the reaction temperature is 220-280 and the reaction time is 150-300 min;
the production temperature of the flash desolventizing tower in the second step is set to be 150-190 at the top of the tower and 210-230 at the bottom of the tower.
2. The method for producing hydrogenated petroleum resin according to claim 1, wherein the production temperature of the superheated steam stripping column in the third step is set to 190 to 210at the top and 220 to 250at the bottom.
3. The method for preparing hydrogenated petroleum resin according to claim 1, wherein the mass ratio of the polymerized petroleum resin d to the organic solvent is 3: 7-6: 4, the reaction condition of the hydrogenation reaction kettle is that the hydrogen pressure is 3-8MPa and the mass airspeed is 2-10 hr -1 The reaction temperature is 220-270 and the reaction time is 150-300 min.
4. The method for producing a hydrogenated petroleum resin according to claim 1, wherein the production temperature of said flash desolventizing column in said fifth step is set to 150 to 190at the top and 210 to 230at the bottom.
5. The method for producing hydrogenated petroleum resin according to claim 1, wherein the production temperature of the superheated steam stripper in the sixth step is set to 190 to 210at the top and 220 to 250at the bottom.
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