CN115894202A - Method for treating distillation still residue of photoinitiator 1173 - Google Patents
Method for treating distillation still residue of photoinitiator 1173 Download PDFInfo
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- CN115894202A CN115894202A CN202211555063.4A CN202211555063A CN115894202A CN 115894202 A CN115894202 A CN 115894202A CN 202211555063 A CN202211555063 A CN 202211555063A CN 115894202 A CN115894202 A CN 115894202A
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- photoinitiator
- distillation
- distillation still
- still residue
- residue
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- 238000004821 distillation Methods 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000002904 solvent Substances 0.000 claims abstract description 22
- 239000012456 homogeneous solution Substances 0.000 claims abstract description 9
- 239000006228 supernatant Substances 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 7
- 239000000047 product Substances 0.000 abstract description 22
- 239000012535 impurity Substances 0.000 abstract description 17
- 238000011084 recovery Methods 0.000 abstract description 8
- 238000005406 washing Methods 0.000 abstract description 6
- 238000004064 recycling Methods 0.000 abstract description 2
- 239000012043 crude product Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 4
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000002920 hazardous waste Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- -1 2-hydroxy-2-methylphenyl Chemical group 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Abstract
The invention relates to a method for treating a photoinitiator 1173 distillation still residue, which comprises the steps of dissolving the distillation still residue by using a specific solvent to obtain a homogeneous solution, adding water to separate out part of impurities, separating to obtain a supernatant, then desolventizing, washing with water, separating to obtain a lower oil phase, and distilling and recycling to obtain the photoinitiator 1173; the method can realize the recovery of the photoinitiator 1173 in the distillation still residue, the purity of the obtained photoinitiator 1173 can reach more than 90 percent, and the mass of the obtained photoinitiator product can account for 25 to 40 percent of the mass of the distillation still residue.
Description
Technical Field
The invention belongs to the field of photoinitiators, and relates to a method for treating distillation still residues of a photoinitiator 1173.
Background
Alpha-hydroxyisobutyrophenone, also known as photoinitiator 1173, is a free radical type I photoinitiator; can be used in ultraviolet light curing varnish of acrylate series on the surfaces of paper, metal and plastic.
CN108863769A discloses a preparation method of a photoinitiator 2-hydroxy-2-methylphenyl propane-1-ketone, which comprises an acylation reaction, a Friedel-crafts reaction, a chlorination reaction and an alkaline hydrolysis reaction to obtain a crude product of the photoinitiator 1173, and the crude product is put into a rectifying still for reduced pressure rectification and fraction collection to obtain the photoinitiator 1173; the distillation process can generate kettle residues which contain the photoinitiator 1173, and the kettle residues are generally treated as hazardous wastes and are not recycled in the prior art due to the high difficulty in further distillation and recycling.
Therefore, it is still of great significance to develop a distillation still residue treatment method capable of realizing recovery of photoinitiator 1173 in distillation still residue.
Disclosure of Invention
The invention aims to provide a method for treating the residue of a distillation kettle of a photoinitiator 1173, which comprises the steps of dissolving the residue of the distillation kettle by using a specific solvent to obtain a homogeneous solution, adding water to precipitate part of impurities, separating liquid to obtain a supernatant, then performing desolventizing, washing with water, separating liquid to obtain a lower-layer oil phase, and distilling and recovering to obtain the photoinitiator 1173; the method can realize the recovery of the photoinitiator 1173 in the distillation still residue, the purity of the obtained photoinitiator 1173 can reach more than 90 percent, and the mass of the obtained photoinitiator product can account for 25 to 40 percent of the mass of the distillation still residue.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a method for treating a photoinitiator 1173 distillation still residue, which comprises the following steps:
(1) Mixing the distillation still residue and a solvent to obtain a homogeneous solution, wherein the solvent is selected from at least one of methanol, ethanol, acetone and acetonitrile;
(2) Adding water into the homogeneous solution in the step (1), mixing, and separating to obtain a supernatant;
(3) Desolventizing the supernatant obtained in the step (2), adding water, mixing, and separating to obtain a lower oil phase;
(4) Distilling the lower oil phase obtained in the step (3) to obtain a photoinitiator 1173.
The preparation process of the photoinitiator 1173 generally comprises acylation reaction, friedel-crafts reaction, halogenation reaction, alkaline hydrolysis reaction, washing and liquid separation to obtain a crude product of the photoinitiator 1173, wherein the crude product comprises the photoinitiator 1173 and byproduct impurities, part of the byproduct impurities are high-boiling-point impurities, and kettle residues exist in the crude product rectification process; the residue in the kettle contains photoinitiator 1173 and high-boiling-point impurities, the separation difficulty of the photoinitiator 1173 and the high-boiling-point impurities is high, rectification is difficult to evaporate, and the organic solvent has solubility to both the photoinitiator and the high-boiling-point impurities, so that extraction difficulty is high; the distillation kettle residue is not recycled conventionally and is directly treated as hazardous waste, so that product waste is caused; based on the above-described problem, the present invention provides a method for treating still residue capable of effectively recovering the photoinitiator 1173 by screening a solvent.
The distillation still residue refers to the still residue obtained after the crude product of the photoinitiator 1173 is rectified.
The residue of the distillation kettle of the photoinitiator 1173 is black tar-like, and the invention discovers that the residue is black tar-like by research, the residue is completely dissolved by adopting a specific solvent to obtain a homogeneous solution, water is slowly dripped in the homogeneous solution under stirring, a black semi-solid semi-liquid paste, namely an impurity phase, can be gradually separated out from the homogeneous solution, after standing, the impurity phase is at the lower layer, the upper product phase is a clear solution, after desolventizing the upper clear solution, washing with water and separating the solution to obtain a lower oil phase, namely a product phase, and then the product phase is distilled to obtain a photoinitiator 1173 product with higher purity; the purity of the 1173 product obtained by the method can reach more than 90 percent, the mass of the obtained photoinitiator 1173 product can account for 25 to 40 percent of the mass of the distillation still residue of the raw material, and the effective recovery of the product in the distillation still residue is realized.
The method provided by the invention has the advantages that the kettle residue is dissolved by a specific solvent to obtain a homogeneous solution, water is added to separate out high-boiling-point impurities, the photoinitiator 1173 and the high-boiling-point impurities are effectively separated, the product recovery ratio and the purity are high, and the industrial application requirements are met.
Preferably, the solvent in step (1) is methanol and/or ethanol.
The solvent is preferably adopted for dissolving the distillation still residue through dissolving and screening, so that the method is favorable for realizing higher recovery ratio and product purity.
Preferably, the mass ratio of the distillation still residue to the solvent in step (1) is 0.8 to 1.1, for example 0.85, 0.9, 0.95, 1 or 1.05, etc.
Preferably, the temperature of mixing in step (1) is from 30 ℃ to 40 ℃, for example 35 ℃.
The treatment method provided by the invention adopts the proportion and the dissolution temperature, so that the dissolution efficiency is improved, and higher recovery ratio and product purity are obtained.
Preferably, the water is added in step (2) in a dropwise manner.
The treatment method provided by the invention adopts the feeding mode, and is beneficial to precipitation of high-boiling-point impurities.
Preferably, the mixing in step (2) is performed by stirring, preferably by rapid stirring.
Preferably, the ratio of the mass of water added in step (2) to the mass of the distillation still residue in step (1) is 0.3 to 0.6, for example 0.35, 0.4, 0.45, 0.5 or 0.55; the water addition amount is adopted to be beneficial to fully separating out high-boiling-point impurities.
Preferably, the mass of solvent desolventized in step (3) is 0.7 to 0.85, such as 0.71, 0.72, 0.73, 0.74, 0.75, 0.76, 0.77, 0.78, 0.79, 0.8, 0.81, 0.82, 0.83, or 0.84, etc., of the mass of solvent added in step (1).
Preferably, the ratio of the mass of water added in step (3) to the mass of the distillation still residue in step (1) is 0.4 to 0.8, for example 0.45, 0.5, 0.55, 0.6, 0.65, 0.7 or 0.75.
In the treatment method of the invention, water is continuously added for water washing after desolventizing is finished, the aim is to wash away the solvent by water, so that the solvent and 1173 products are separated, and the distilled 1173 distillate does not contain the solvent.
Preferably, the method of desolventizing in step (3) is atmospheric distillation.
Preferably, the distillation method in step (4) is vacuum distillation.
Compared with the prior art, the invention has the following beneficial effects:
according to the method for treating the distillation still residue, a specific solvent is used for dissolving the distillation still residue to obtain a homogeneous phase solution, water is added to precipitate high-boiling-point impurities, supernatant liquid is subjected to desolventizing, water washing and lower oil phase distillation are carried out, so that the effective separation of the photoinitiator 1173 and the high-boiling-point impurities is realized, the ratio of the photoinitiator 1173 product to the raw material distillation still residue is high, the product purity is high, and the effective recovery of the product in the distillation still residue is realized.
Detailed Description
The technical solution of the present invention is further described below by way of specific embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
The embodiment provides a method for treating a photoinitiator 1173 distillation still residue, which comprises the following steps:
(1) Dissolving: 172g of black tarry 1173 distillation still residue and 178g of methanol are added into a four-port bottle, and the mixture is put into a water bath at 35 ℃ and stirred for 15 minutes, and all the components are dissolved into a homogeneous phase.
(2) And (3) impurity precipitation: slowly dripping water into the homogeneous phase in the step (1) under stirring, observing the precipitation phenomenon, adding 70g of water in total, rapidly stirring uniformly, precipitating black semi-solid semi-liquid paste, standing and separating to obtain 375.8g of supernatant;
(3) Concentration: carrying out normal-pressure desolventizing on the supernatant obtained in the step (2), evaporating 141g of methanol, continuously adding 93g of water into a bottle, uniformly stirring, and then carrying out liquid separation to obtain 118g of a lower-layer oil phase;
(4) Distillation recovery 1173: the lower oil phase obtained in step (3) was distilled under reduced pressure to obtain 54g of a distilled product (GC-detected 1173 content: 91.1%) and 34.6g of a distillation residue.
The black tarry 1173 still bottoms from step (1) of this example were obtained by a process comprising: and carrying out reduced pressure distillation on 300g of crude product obtained by the alkaline hydrolysis reaction of the photoinitiator 1173, collecting fractions with the overhead temperature of 100-110 ℃ under the vacuum degree of 2mmHg, obtaining 10g of distillation still residue in a distillation flask after the distillation is finished, and repeating the operation to obtain the distillation still residue required by the experiment.
Example 2
This example is different from example 1 only in that methanol and the like in step (1) are replaced by ethanol, and other parameters and conditions are exactly the same as those in example 1.
In this example, 53.4g of a distilled product (content: 91.7% by GC analysis) and 35.8g of a distillation residue were obtained by distillation under reduced pressure in the step (4).
Example 3
This example is different from example 1 only in that acetone is substituted for methanol and the like in step (1) in quality, and other parameters and conditions are exactly the same as those in example 1.
In this example, 45.2g of a distilled product obtained in the step (4) of the present example was distilled under reduced pressure, (GC-based detection 1173 content: 90.5%), and 39.2g of a distillation residue were obtained.
Example 4
This example is different from example 1 only in that methanol and the like were replaced by acetonitrile in step (1), and other parameters and conditions were exactly the same as those in example 1.
In this example, in the step (4), 46.8g of a distilled product was obtained by distillation under reduced pressure, (content: 90.2% by GC-based detection 1173), and 42g of a distillation residue was obtained.
As can be seen from the results of comparative examples 1-4, the solvent for dissolving the distillation still residue in step (1) of the present invention is preferably methanol or ethanol, which has the advantage of dissolving 1173 in the residue to the maximum extent compared with other solvents, so that more distillation products can be recovered, the product purity is higher, the boiling point of methanol is low, the temperature required for distillation is low, and the cost for treating the residue is low.
The applicant declares that the above description is only a specific embodiment of the present invention, but the scope of the present invention is not limited thereto, and it should be understood by those skilled in the art that any changes or substitutions that can be easily conceived by those skilled in the art within the technical scope of the present invention are within the scope and disclosure of the present invention.
Claims (10)
1. A method for treating distillation still residue of a photoinitiator 1173 is characterized by comprising the following steps:
(1) Mixing the distillation kettle residue and a solvent to obtain a homogeneous phase solution; the solvent is selected from at least one of methanol, ethanol, acetone and acetonitrile;
(2) Adding water into the homogeneous solution obtained in the step (1), mixing, and separating to obtain a supernatant;
(3) Desolventizing the supernatant obtained in the step (2), adding water, mixing, and separating to obtain a lower oil phase;
(4) Distilling the lower oil phase obtained in the step (3) to obtain a photoinitiator 1173.
2. The process of claim 1, wherein the solvent of step (1) is methanol or ethanol.
3. The process according to claim 1 or 2, wherein the mass ratio of the distillation still residue to the solvent in the step (1) is 0.8 to 1.1.
4. The process according to any one of claims 1 to 3, wherein the temperature of mixing in step (1) is from 30 ℃ to 40 ℃.
5. The process according to any one of claims 1 to 4, wherein the water is added dropwise in the step (2).
6. The process according to any one of claims 1 to 5, wherein the mixing in step (2) is carried out by stirring.
7. The process according to any one of claims 1 to 6, wherein the ratio of the mass of water added in step (2) to the mass of the distillation still residue in step (1) is from 0.3 to 0.6.
8. The process according to any one of claims 1 to 7, wherein the ratio of the mass of water added in step (3) to the mass of the distillation still residue in step (1) is from 0.4 to 0.8.
9. The process according to any one of claims 1 to 8, wherein the desolventizing in step (3) is atmospheric distillation.
10. The process according to any one of claims 1 to 9, wherein the distillation in step (4) is carried out under reduced pressure.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202211555063.4A CN115894202A (en) | 2022-12-06 | 2022-12-06 | Method for treating distillation still residue of photoinitiator 1173 |
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| CN202211555063.4A CN115894202A (en) | 2022-12-06 | 2022-12-06 | Method for treating distillation still residue of photoinitiator 1173 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS635050A (en) * | 1986-06-26 | 1988-01-11 | Daicel Chem Ind Ltd | Production of alpha-hydroxyketone compound |
| US20050004249A1 (en) * | 2001-11-08 | 2005-01-06 | Andre Fuchs | Novel disfunctional photoinitiators |
| CN101225029A (en) * | 2008-02-21 | 2008-07-23 | 长沙新宇化工实业有限公司 | Method for synthesizing aromatic alpha-hydroxyacetone compounds |
| CN102241580A (en) * | 2011-01-07 | 2011-11-16 | 长春工业大学 | Method for recovering organic carboxylic acids from corn chemical alcohol reaction kettle residues by utilizing complex extraction |
| JP2016145198A (en) * | 2015-01-30 | 2016-08-12 | 東ソー株式会社 | N-vinylimidazolidone compound, and polymer thereof |
| CN107739303A (en) * | 2017-10-27 | 2018-02-27 | 天津久日新材料股份有限公司 | A kind of preparation method of α hydroxyls ketone-type photoinitiators |
| CN109467250A (en) * | 2018-12-28 | 2019-03-15 | 湖南久日新材料有限公司 | A kind of 1173 and 184 technique waste water administering method of photoinitiator |
| CN109651134A (en) * | 2019-02-13 | 2019-04-19 | 天津城建大学 | A kind of preparation method of photoinitiator 2- methyl -2- hydroxyl -1- phenylacetone |
| CN111269336A (en) * | 2020-03-22 | 2020-06-12 | 胥彩虹 | Polymerizable photoinitiator and preparation method thereof |
| CN112159365A (en) * | 2020-10-13 | 2021-01-01 | 大连百傲化学股份有限公司 | Method for co-producing OIT and DCOIT |
| CN113735764A (en) * | 2021-09-04 | 2021-12-03 | 内蒙古佳瑞米精细化工有限公司 | Method for recovering 2-cyano-3-chloro-5-trifluoromethylpyridine rectifying still residue |
| CN113979872A (en) * | 2021-11-09 | 2022-01-28 | 国药集团威奇达药业有限公司 | Comprehensive recovery method of effective components in potassium clavulanate kettle residual liquid |
-
2022
- 2022-12-06 CN CN202211555063.4A patent/CN115894202A/en active Pending
Patent Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS635050A (en) * | 1986-06-26 | 1988-01-11 | Daicel Chem Ind Ltd | Production of alpha-hydroxyketone compound |
| US20050004249A1 (en) * | 2001-11-08 | 2005-01-06 | Andre Fuchs | Novel disfunctional photoinitiators |
| CN101225029A (en) * | 2008-02-21 | 2008-07-23 | 长沙新宇化工实业有限公司 | Method for synthesizing aromatic alpha-hydroxyacetone compounds |
| CN102241580A (en) * | 2011-01-07 | 2011-11-16 | 长春工业大学 | Method for recovering organic carboxylic acids from corn chemical alcohol reaction kettle residues by utilizing complex extraction |
| JP2016145198A (en) * | 2015-01-30 | 2016-08-12 | 東ソー株式会社 | N-vinylimidazolidone compound, and polymer thereof |
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| CN113735764A (en) * | 2021-09-04 | 2021-12-03 | 内蒙古佳瑞米精细化工有限公司 | Method for recovering 2-cyano-3-chloro-5-trifluoromethylpyridine rectifying still residue |
| CN113979872A (en) * | 2021-11-09 | 2022-01-28 | 国药集团威奇达药业有限公司 | Comprehensive recovery method of effective components in potassium clavulanate kettle residual liquid |
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