CN114349621A - Method suitable for small-sized continuous rectification of acylation reaction liquid - Google Patents
Method suitable for small-sized continuous rectification of acylation reaction liquid Download PDFInfo
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- CN114349621A CN114349621A CN202111638859.1A CN202111638859A CN114349621A CN 114349621 A CN114349621 A CN 114349621A CN 202111638859 A CN202111638859 A CN 202111638859A CN 114349621 A CN114349621 A CN 114349621A
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- 238000005917 acylation reaction Methods 0.000 title claims abstract description 31
- 239000012295 chemical reaction liquid Substances 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000007788 liquid Substances 0.000 claims abstract description 41
- 238000003860 storage Methods 0.000 claims abstract description 18
- 238000005086 pumping Methods 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 238000001704 evaporation Methods 0.000 claims abstract description 3
- 238000010992 reflux Methods 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 7
- 230000005494 condensation Effects 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000012856 packing Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 abstract description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 34
- 239000000047 product Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 11
- QIMMUPPBPVKWKM-UHFFFAOYSA-N 2-methylnaphthalene Chemical compound C1=CC=CC2=CC(C)=CC=C21 QIMMUPPBPVKWKM-UHFFFAOYSA-N 0.000 description 10
- WEBCKNDFLRJODL-UHFFFAOYSA-N 1-(6-methylnaphthalen-2-yl)propan-1-one Chemical compound C1=C(C)C=CC2=CC(C(=O)CC)=CC=C21 WEBCKNDFLRJODL-UHFFFAOYSA-N 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 7
- 239000002994 raw material Substances 0.000 description 6
- SPAYGOAEIJHIDE-UHFFFAOYSA-N 1-(6-methylnaphthalen-2-yl)ethanone Chemical compound C1=C(C)C=CC2=CC(C(=O)C)=CC=C21 SPAYGOAEIJHIDE-UHFFFAOYSA-N 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- KRVWMPNTAYTOGS-UHFFFAOYSA-N 2-methyl-6-propan-2-ylnaphthalene Chemical compound C1=C(C)C=CC2=CC(C(C)C)=CC=C21 KRVWMPNTAYTOGS-UHFFFAOYSA-N 0.000 description 1
- WWIKFXPBGKBXLZ-UHFFFAOYSA-N 6-methylnaphthalene-2-carbaldehyde Chemical group C1=C(C=O)C=CC2=CC(C)=CC=C21 WWIKFXPBGKBXLZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229920000106 Liquid crystal polymer Polymers 0.000 description 1
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
Images
Abstract
The invention provides a method suitable for small-sized continuous rectification of acylation reaction liquid, which comprises the following steps: (1) feeding an acylation reaction liquid for preparing 2-methyl-6-acylnaphthalene from the middle part of a first rectifying tower into the first rectifying tower for rectification, evaporating light fractions from the top of the tower, condensing and recovering the light fractions, and pumping a kettle bottom liquid into a liquid storage tank for storage while the kettle bottom liquid is hot; (2) heating the bottom liquid accumulated in the liquid storage tank, pumping the heated bottom liquid into a second rectifying tower, carrying out intermittent reduced pressure rectification, and collecting light fractions from the tower top; after the light fraction is extracted, the valve on the light fraction collecting pipeline is closed, the valve on the product collecting pipeline is opened, and the product is received; and (4) the heavy component in the tower bottom enters the tower bottom, and the hot heavy component is pumped into a material collecting tank in the tower bottom. The method is simple to operate, is suitable for small-scale purification of acylation reaction liquid containing 2-methyl-6-acylnaphthalene, and the purity of the prepared product can reach more than 99.5 percent.
Description
Technical Field
The invention belongs to the technical field of coal chemical industry, and particularly relates to a method suitable for small continuous rectification of acylation reaction liquid.
Background
The coal reserves in China are abundant, and at present, the method has important significance for developing a high added value route of naphthalene as a measure for increasing the comprehensive utilization of heavy components in energy such as coal, petroleum and the like under the condition of increasingly tense energy. The 2, 6-naphthalene dicarboxylic acid is an important intermediate for preparing polyester fibers and F-grade insulating materials with high strength and excellent dyeing property, is also an important monomer for synthesizing high-performance PEN, PBN, liquid crystal polymers and polyurethane resin, and has wide application prospect in the fields of fibers, films, packaging containers, electronic components and the like.
2-methyl-6-acyl naphthalene is an important raw material for preparing 2, 6-naphthalene dicarboxylic acid, and 2, 6-naphthalene dicarboxylic acid can be prepared after oxidation. The 2-methylnaphthalene is widely available, cheap and easily available (coal tar, ethylene tar and the like are rich in a considerable amount of 2-methylnaphthalene), and 2-methyl-6-acylnaphthalene can be prepared by taking 2-methylnaphthalene as a raw material through acylation reaction, hydrolysis and purification. At present, the research of preparing 2-methyl-6-acyl naphthalene by taking 2-methylnaphthalene as a raw material, propionyl chloride as an acylating agent, aluminum trichloride as a catalyst and nitrobenzene as a solvent and carrying out Friedel-crafts acylation reaction at normal temperature and normal pressure is carried out in China. After the acylation reaction is finished, the reaction hydrolysis is quenched, the pH value of an organic phase is hydrolyzed to 6-7, and the 2-methyl-6-propionyl naphthalene is obtained by methods such as reduced pressure distillation, recrystallization and the like.
CN112876359A discloses a method for preparing dimethyl 2, 6-naphthalene dicarboxylate, in which the reaction solution is added into ethanol aqueous solution to quench, the obtained nitrobenzene phase is separated by layers and vacuum distilled to recover solvent nitrobenzene, and crude product 2-methyl-6-acetyl naphthalene (containing isomer by-product) is obtained, wherein the purity of 2-methyl-6-acetyl naphthalene is only 79.0%. The boiling point of the 2-methyl-6-acyl naphthalene is close to that of the isomer thereof, complete purification is difficult to realize by reduced pressure distillation in the industrial process, and the energy consumption is high.
Disclosure of Invention
The invention aims to provide a method suitable for small-sized continuous rectification of acylation reaction liquid, which is simple to operate, has the product purity of over 99.5 percent, is suitable for small-scale purification of acylation reaction liquid containing 2-methyl-6-acylnaphthalene, can recycle a recovered nitrobenzene solvent and saves economic cost.
The technical scheme of the invention is as follows:
the invention provides a method suitable for small-sized continuous rectification of acylation reaction liquid, which comprises the following steps:
(1) feeding an acylation reaction liquid for preparing 2-methyl-6-acylnaphthalene from the middle part of a first rectifying tower into the first rectifying tower for rectification, evaporating light fractions from the top of the tower, condensing and recovering the light fractions, and pumping a kettle bottom liquid into a liquid storage tank for storage while the kettle bottom liquid is hot;
(2) heating the bottom liquid accumulated in the liquid storage tank, pumping the heated bottom liquid into a second rectifying tower, carrying out intermittent reduced pressure rectification, and collecting light fractions from the tower top; after the light fraction is extracted, the valve on the light fraction collecting pipeline is closed, the valve on the product collecting pipeline is opened, and the product is received; and (4) the heavy component in the tower bottom enters the tower bottom, and the hot heavy component is pumped into a material collecting tank in the tower bottom.
In some embodiments, the packing used for the first rectification column and the second rectification column is in the shape of a spring, a theta ring, or a combination thereof.
In some embodiments, the pressure of the first rectification column is from 0.05KPa to 10KPa, preferably from 0.1KPa to 2 KPa; the reflux ratio is (1-2): 1.
in some embodiments, the pressure of the second rectification column is from 0.05KPa to 10KPa, preferably from 0.1KPa to 2 KPa; the reflux ratio is (5-10): 1.
in some embodiments, the condensation temperature of the first rectification column is 10 to 20 ℃.
In some embodiments, the condensation temperature of the second rectification column is 50 to 90 ℃.
In some embodiments, the volume of the still bottoms accumulated in the liquid storage tank is 1/4-3/4 of the volume of the liquid storage tank.
In some embodiments, a valve controller is further disposed at the rear end of the condenser at the top of the second distillation column, and is configured to control a valve on the light fraction collecting line and a valve on the product collecting line, so that once the temperature reaches a set value, the valve on the light fraction collecting line is closed, and the valve on the product collecting line is opened to receive the product.
In some embodiments, the acyl group of the 2-methyl-6-acylnaphthalene is one of methyl, ethyl, propyl, or isopropyl, i.e., the product 2-methyl-6-acylnaphthalene is 2-methyl-6-formylnaphthalene, 2-methyl-6-acetylnaphthalene, 2-methyl-6-propionylnaphthalene, or 2-methyl-6-isopropylnaphthalene.
In some embodiments, the acyl group of the 2-methyl-6-acylnaphthalene is propyl, i.e., the product is 2-methyl-6-propionylnaphthalene.
The invention has the advantages and beneficial effects that:
(1) the method for purifying the 2-methyl-6-acylnaphthalene is simple to operate, low in cost and suitable for purifying small-scale acylation reaction liquid (the annual treatment capacity of the acylation reaction liquid is below 1000 tons, and the annual running time is calculated by 7200 hours), and the purity of the finally obtained product can reach more than 99.5%.
(2) When the feeding amount of the acylation reaction liquid is less, the bottom liquid of the first rectifying tower is not enough to supply to the second rectifying tower for a long-time and stable continuous rectifying process, the bottom liquid of the kettle can be accumulated in the liquid storage tank for many times, and after reaching a certain degree, the bottom liquid is sent to the second rectifying tower for further rectification, and finally a relatively pure 2-methyl-6-acylnaphthalene product is obtained.
(3) The invention can recover nitrobenzene solvent through the first rectifying tower, and the yield is more than 99 percent. If in the industrial continuous production process, the recovered nitrobenzene can be returned to the acylation reaction stage for reuse, so that the economic cost is saved.
(4) The rear end of the condenser at the top of the second rectifying tower is also provided with a valve controller which is used for controlling a valve on a light fraction collecting pipeline and a valve on a product collecting pipeline, once the temperature reaches a set value, the valve on the light fraction collecting pipeline can be automatically closed, and meanwhile, the valve on the product collecting pipeline can be automatically opened to receive a product, so that the operation error of personnel can be avoided, and a high-purity product can be accurately controlled and obtained.
Drawings
FIG. 1 is a process flow diagram of the present invention.
Detailed Description
The following detailed description of embodiments of the invention is intended to be illustrative, and not to be construed as limiting the invention.
The acylation reaction liquid is obtained by taking 2-methylnaphthalene as a raw material, propionyl chloride as an acylating agent, aluminum trichloride as a catalyst and nitrobenzene as a solvent and carrying out Friedel-crafts acylation reaction at normal temperature and normal pressure to prepare 2-methyl-6-acylnaphthalene.
Example 1
A method suitable for small-scale continuous rectification of acylation reaction liquid comprises the following steps:
(1) feeding the acylation reaction liquid A from the middle part of the first rectifying tower into the first rectifying tower for rectification, wherein the acylation reaction liquid A contains 78 wt% of nitrobenzene solvent and 22 wt% of 2-methyl-6-propionyl naphthalene crude fraction. The pressure of the first rectifying tower is 0.1kPa, the rectifying temperature is 45-130 ℃, nitrobenzene is evaporated from the top of the tower at 67 ℃, the reflux ratio is 1:1, the condensing temperature of the top of the tower is 15 ℃, gas-phase nitrobenzene at the top of the tower is condensed, then nitrobenzene solvent C is recovered from the top of the tower, the temperature of bottom liquid B of the kettle is 130 ℃, and the bottom liquid B is pumped into a liquid storage tank for storage while the bottom liquid B is hot. After the distillation in the first rectifying tower, 99% of nitrobenzene solvent C is recovered, and the bottom liquid B contains 80% of crude 2-methyl-6-propionyl naphthalene.
(2) Heating the bottom liquid accumulated in the liquid storage tank at 100 ℃, directly pumping the heated bottom liquid into a second rectifying tower for intermittent reduced pressure rectification, wherein the pressure of the second rectifying tower is 0.1kPa, the reflux ratio is 5:1, the condensation temperature is 50 ℃, and collecting a light fraction D at 55-130 ℃ from the top of the tower; after the light fraction is extracted and the temperature is stabilized at 135 ℃, the valve on the light fraction collecting pipeline is automatically closed, and meanwhile, the valve on the product collecting pipeline is automatically opened to stably receive the product E2-methyl-6-propionyl naphthalene; and (4) feeding the heavy component F in the tower bottom into the tower bottom, and pumping the heavy component F into a material collecting tank in the tower bottom while the heavy component F is hot.
The theoretical plate number of the first rectifying tower is 30, and the feeding position is positioned on the 15 th theoretical plate; the theoretical plate number of the second rectifying column was 40, and the feed position was located at the 20 th theoretical plate.
The purity of 2-methyl-6-propionyl naphthalene prepared by the method of example 1 can reach 99.5%.
Example 2
A method suitable for small-scale continuous rectification of acylation reaction liquid comprises the following steps:
(1) feeding an acylation reaction liquid A from the middle part of the first rectifying tower into the first rectifying tower for rectification, wherein the acylation reaction liquid A contains 83 wt% of nitrobenzene solvent and 17 wt% of raw material A of 2-methyl-6-propionyl naphthalene crude fraction. The pressure of the first rectifying tower is 1kPa, the heating temperature of the tower kettle is 170 ℃, nitrobenzene is evaporated from the top of the tower at the temperature of 80 ℃, the reflux ratio is 1.1:1, the condensation temperature of the top of the tower is 15 ℃, gas-phase nitrobenzene at the top of the tower is condensed, then nitrobenzene solvent C is recovered from the top of the tower, the temperature of bottom liquid B of the tower is 160 ℃, and the bottom liquid B is pumped into a liquid storage tank for storage while the bottom liquid B is hot. After the distillation in the first rectifying tower, 99.5% of nitrobenzene solvent C is recovered, and the purity of the crude 2-methyl-6-propionyl naphthalene in the bottom liquid B is 78%.
(2) Heating kettle bottom liquid accumulated in a liquid storage tank at 167 ℃, directly pumping the kettle bottom liquid into a second rectifying tower for intermittent reduced pressure rectification when the kettle bottom liquid is hot, collecting light fraction D at 80-175 ℃ from the tower top when the pressure of the second rectifying tower is 1kPa, the reflux ratio is 6:1, the condensation temperature is 75 ℃, automatically closing a valve on a light fraction collecting pipeline after the light fraction is collected and the temperature is stabilized at 180 ℃, automatically opening a valve on a product collecting pipeline simultaneously, stably receiving a product E2-methyl-6-propionyl naphthalene, and enabling a kettle heavy component F to enter the tower bottom and pump the heavy component F to a kettle material collecting tank when the kettle is hot.
The theoretical plate number of the first rectifying tower is 30, and the raw material feeding position is located on the 15 th theoretical plate; the theoretical plate number of the second rectifying column was 40, and the feed position was located at the 20 th theoretical plate.
The purity of 2-methyl-6-propionyl naphthalene prepared by the method of example 2 can reach 99.5%.
In the present disclosure, the terms "one embodiment," "some embodiments," "an example," "a specific example," or "some examples" and the like mean that a specific feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the present disclosure. In this specification, the schematic representations of the terms used above are not necessarily intended to refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples. Furthermore, various embodiments or examples and features of different embodiments or examples described in this specification can be combined and combined by one skilled in the art without contradiction.
Although embodiments of the present invention have been shown and described above, it is understood that the above embodiments are exemplary and should not be construed as limiting the present invention, and that variations, modifications, substitutions and alterations can be made to the above embodiments by those of ordinary skill in the art within the scope of the present invention.
Claims (8)
1. A method for continuously rectifying acylation reaction liquid is characterized by comprising the following steps:
(1) feeding an acylation reaction liquid for preparing 2-methyl-6-acylnaphthalene from the middle part of a first rectifying tower into the first rectifying tower for rectification, evaporating light fractions from the top of the tower, condensing and recovering the light fractions, and pumping a kettle bottom liquid into a liquid storage tank for storage while the kettle bottom liquid is hot;
(2) heating the bottom liquid accumulated in the liquid storage tank, pumping the heated bottom liquid into a second rectifying tower, carrying out intermittent reduced pressure rectification, and collecting light fractions from the tower top; after the light fraction is extracted, the valve on the light fraction collecting pipeline is closed, the valve on the product collecting pipeline is opened, and the product is received; and (4) the heavy component in the tower bottom enters the tower bottom, and the hot heavy component is pumped into a material collecting tank in the tower bottom.
2. The method of claim 1, wherein the packing material used in the first distillation column and the second distillation column is in the form of a spring, a theta ring or a combination thereof.
3. The method for continuously rectifying acylation reaction liquid according to claim 1, wherein the pressure of the first rectifying tower is 0.05KPa to 10 KPa; the reflux ratio is (1-2): 1.
4. the method for continuously rectifying acylation reaction liquid according to claim 1 or 3, wherein the condensation temperature of the first rectifying tower is 10-20 ℃.
5. The method for continuously rectifying acylation reaction liquid according to claim 1, wherein the pressure of the second rectifying tower is 0.05KPa to 10 KPa; the reflux ratio is (5-10): 1.
6. the method for continuously rectifying acylation reaction liquid according to claim 1 or 5, wherein the condensation temperature of the second rectifying tower is 50-90 ℃.
7. The method for continuously rectifying acylation reaction liquid according to claim 6, wherein a valve controller is further provided at the rear end of the condenser of the second rectifying tower.
8. A method for continuously rectifying an acylation reaction liquid according to any one of claims 1 to 7, wherein the acyl group of the 2-methyl-6-acylnaphthalene is one of methyl, ethyl, propyl or isopropyl.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114874086A (en) * | 2022-05-10 | 2022-08-09 | 开滦（集团）有限责任公司 | Method for treating alkyl naphthoyl reaction liquid |
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| US4021495A (en) * | 1974-06-19 | 1977-05-03 | Sumitomo Chemical Company, Limited | Purification of β-naphthol |
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2021
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| CN114874086A (en) * | 2022-05-10 | 2022-08-09 | 开滦（集团）有限责任公司 | Method for treating alkyl naphthoyl reaction liquid |
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