CN115745850B - Method for continuous flow production of sodium dodecyl diphenyl ether sulfonate - Google Patents
Method for continuous flow production of sodium dodecyl diphenyl ether sulfonate Download PDFInfo
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- CN115745850B CN115745850B CN202211472181.9A CN202211472181A CN115745850B CN 115745850 B CN115745850 B CN 115745850B CN 202211472181 A CN202211472181 A CN 202211472181A CN 115745850 B CN115745850 B CN 115745850B
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- diphenyl ether
- dodecyl diphenyl
- reaction
- sulfur trioxide
- sodium dodecyl
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- LGNQGTFARHLQFB-UHFFFAOYSA-N 1-dodecyl-2-phenoxybenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1OC1=CC=CC=C1 LGNQGTFARHLQFB-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 38
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 title claims abstract description 27
- 239000011734 sodium Substances 0.000 title claims abstract description 27
- 229910052708 sodium Inorganic materials 0.000 title claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 title abstract description 10
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims abstract description 60
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- 230000032683 aging Effects 0.000 claims abstract description 25
- 230000008569 process Effects 0.000 claims abstract description 22
- 238000006277 sulfonation reaction Methods 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 239000012295 chemical reaction liquid Substances 0.000 claims description 23
- 238000001816 cooling Methods 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 8
- 238000010924 continuous production Methods 0.000 claims description 8
- 238000006386 neutralization reaction Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 3
- 239000012528 membrane Substances 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 238000007710 freezing Methods 0.000 claims description 2
- 230000008014 freezing Effects 0.000 claims description 2
- 239000000758 substrate Substances 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Abstract
The invention discloses a method for continuously producing sodium dodecyl diphenyl ether sulfonate. The invention adopts sulfur trioxide with strong sulfonation capability as a sulfonating agent, dodecyl diphenyl ether is used as a substrate, the substrate is precooled in a precooling pipe and then is introduced into a micromixer to be uniformly mixed, the reaction of the first stage of the sulfonation process is carried out by utilizing the advantages of controllable residence time, temperature and flow rate of a delay coil microreactor, and the aging reaction of the second stage of the sulfonation process is carried out in an aging kettle. The reaction process for continuously producing sodium dodecyl diphenyl ether sulfonate by using the method has the advantages of high safety, strong operability, high production efficiency, good product selectivity and high conversion rate.
Description
Technical Field
The invention relates to the field of organic synthesis, in particular to a method for continuously producing sodium dodecyl diphenyl ether sulfonate.
Background
The sodium dodecyl diphenyl ether sulfonate is a novel anionic surfactant with a monosulfonate hydrophilic structure, and has strong adsorption capacity, good thermal stability and high stability under strong acid, strong alkali and salt solution due to a unique molecular structure, and has a plurality of advantages compared with the traditional surfactant: excellent solubility, hard water resistance, stability and coupling property. In recent years, the sodium dodecyl diphenyl ether sulfonate has wide application in geological fields such as oil extraction, soil purification and the like, and in aspects such as colloid rheological property, microemulsion, liquid crystal templates and the like.
At present, the production of sodium dodecyl diphenyl ether sulfonate generally adopts an intermittent kettle type production process, the reaction process is completed by dropwise adding SO 3 solution in a reaction kettle with jacket heat exchange at the temperature of-15 ℃, and the reaction temperature is controlled to be 0-10 ℃ in the dropwise adding process. However, the intermittent kettle type production process has the problems of deeper product chromaticity, high sodium sulfate content, long reaction period, difficult control of the reaction process and the like, and is not beneficial to large-scale and continuous production of the process.
Whereas a continuous flow microreactor is a chemical reactor with a channel having a characteristic dimension on the order of micrometers and millimeters. The small characteristic size and the large specific surface area of the continuous flow micro-reactor enable the continuous flow micro-reactor to have good heat and mass transfer performance, and simultaneously can meet the condition of continuous production.
The invention provides a method for preparing sodium dodecyl diphenyl ether sulfonate, which aims to solve the problems of the traditional preparation method of sodium dodecyl diphenyl ether sulfonate.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a method for continuously producing sodium dodecyl diphenyl ether sulfonate. The method combines a continuous flow micro-reactor and a micro-mixer to uniformly mix the reaction system, has high mass and heat transfer efficiency, has the advantages of high production efficiency, low production cost, high product yield, simple operation and the like, and can realize continuous production.
In order to achieve the above object, the present invention provides the following technical solutions:
The invention provides a method for continuously producing sodium dodecyl diphenyl ether sulfonate, which comprises the following steps:
(1) The sulfur trioxide solution is used as a sulfonating agent, dodecyl diphenyl ether is used as a base material, and the flow of a metering pump is regulated to ensure that two materials are respectively and continuously conveyed to a pre-cooling pipe for cooling;
(2) Conveying the cooled sulfur trioxide solution and dodecyl diphenyl ether into a micro-inverse mixer for full contact mixing;
(3) Delivering the fully mixed materials to a time-delay coil microreactor to perform a first-stage reaction in the sulfonation process;
(4) After the reaction liquid finishes the first-stage reaction, the reaction liquid enters an aging kettle for collection; after the ageing kettle collects the reaction liquid with set quality, the reaction liquid is switched to a new ageing kettle for collection; collecting the reaction liquid in the aging kettle, and continuously stirring to enable the reaction liquid to carry out the aging reaction of the second stage of the sulfonation process in the aging kettle;
(5) After the aging reaction is finished, the reaction liquid is subjected to hydrolysis, neutralization and concentration treatment to obtain a sodium dodecyl diphenyl ether sulfonate product; wherein, the neutralization process is to add NaOH to neutralize dodecyl diphenyl ether sulfonic acid to prepare sodium dodecyl diphenyl ether sulfonate.
As a preferred embodiment of the present invention, in the step (1),
The sulfur trioxide solution is a dichloroethane solution of sulfur trioxide, and the mass fraction of the sulfur trioxide in the sulfur trioxide solution is 8% -25%; the flow ratio of the sulfur trioxide solution to the dodecyl diphenyl ether fed into the pre-cooling pipe is 4:3-2:1.
As a preferred embodiment of the present invention, in the step (1), the temperature range at which the sulfur trioxide solution and dodecyl diphenyl ether are required to be cooled in the pre-cooling tube is-15 ℃ to 0 ℃ and the cooling residence time is 5s to 10s.
As a preferred scheme of the invention, in the step (2), the molar ratio of the sulfur trioxide in the sulfur trioxide solution to the dodecyl diphenyl ether in the micro-inverse mixer is 1.8-2.3; the micro-inverse mixer is a membrane dispersion micro-mixer.
As a preferred embodiment of the present invention, in the step (3), the temperature range of the reaction of the sulfur trioxide solution and dodecyl diphenyl ether in the time-lapse coiled-tube microreactor is-15 ℃ to 0 ℃ and the residence time of the reaction is 7s to 20s. In the step (4), the reaction temperature of the reaction liquid in the aging kettle ranges from 0 ℃ to 15 ℃ and the stirring time ranges from 30min to 80min.
As a preferable scheme of the invention, the temperatures of the pre-cooling pipe, the micro-inverse mixer and the time-delay coil microreactor are controlled by a freezing thermostat.
As a preferable scheme of the invention, in the step (1), the diameter of the pre-cooling pipe is in the range of 0.8mm-4mm. As a preferable scheme of the invention, in the step (3), the pipe diameter of the time delay coil microreactor is in the range of 0.8mm-4mm.
The beneficial effects of the invention are as follows:
(1) Sulfur trioxide is used as a sulfonating agent, so that the sulfonating capability is high, the reaction time is greatly shortened, few byproducts are produced, and the product yield is high.
(2) And a membrane dispersion micromixer is adopted, so that the mixing effect of materials is enhanced. The continuous flow microreactor is adopted to carry out the reaction of the first stage of the sulfonation process, the smaller characteristic size of the continuous flow microreactor strengthens the heat and mass transfer effect of the reaction materials, reduces side reactions, improves the product selectivity, realizes continuous production, and has higher production efficiency.
(3) Besides the raw materials do not need to be additionally supplemented with solvent and catalyst, solid waste is avoided, the safety of the reaction process is high, and the operability is strong.
Drawings
FIG. 1 is a schematic flow chart of the continuous production of sodium dodecyl diphenyl ether sulfonate according to the present invention.
Detailed Description
The invention is further described below with reference to the drawings and examples.
Examples: referring to fig. 1, the method for continuously producing sodium dodecyl diphenyl ether sulfonate by adopting the method comprises the following specific steps:
(1) Taking a sulfur trioxide solution with the mass fraction of 12% as a sulfonating agent, taking dodecyl diphenyl ether as a backing material, wherein n (sulfur trioxide) is 2.13, regulating a metering pump to ensure that the sulfur trioxide solution is introduced into a pre-cooling pipe at the flow rate of 27.5mL/min for 5s to be cooled to the temperature of minus 15 ℃, and regulating the metering pump to ensure that the dodecyl diphenyl ether is introduced into the pre-cooling pipe at the flow rate of 33.0mL/min for 5s to be cooled to the temperature of minus 15 ℃.
(2) And (3) conveying the sulfur trioxide solution cooled in the step (1) and dodecyl diphenyl ether into a micro-inverse mixer for full contact mixing.
(3) And (3) conveying the materials fully mixed in the step (2) into a time-delay coil microreactor, and staying for 12s at the temperature of minus 15 ℃ to carry out the reaction of the first stage of the sulfonation process.
(4) And (3) collecting the reaction liquid after the first-stage reaction in the step (3) into an aging kettle. After 600g of reaction liquid is collected by the aging kettle, the reaction liquid is switched to a new aging kettle for collection; and (3) continuously stirring the reaction liquid in the aging kettle at the water bath temperature of 8 ℃ for 70min, and performing the aging reaction of the second stage of the sulfonation process on the reaction liquid.
(5) And (3) collecting the reaction liquid after the aging reaction in the step (4), and obtaining the sodium dodecyl diphenyl ether sulfonate product through the post-treatment processes of hydrolysis, naOH neutralization and concentration.
Comparative example: the method for producing the sodium dodecyl diphenyl ether sulfonate by adopting the traditional kettle type process comprises the following specific steps:
(1) 275mL of a 12% by mass sulfur trioxide solution and 330mL of dodecyl diphenyl ether, n (sulfur trioxide): n is 2.13, were added to the reaction vessel.
(2) And (3) starting the reaction kettle to stir, starting the water bath to control the temperature, keeping the temperature of the reaction kettle constant at 8 ℃, and continuously carrying out the sulfonation process to react for 70min.
(3) And (3) collecting the reaction liquid after the aging reaction in the step (2), and obtaining the sodium dodecyl diphenyl ether sulfonate product through the post-treatment processes of hydrolysis, naOH neutralization and concentration.
The reaction equations of the two processes are the same, and are as follows:
And detecting products produced by two processes: the color number of the sodium dodecyl diphenyl ether sulfonate product is measured by a pt-co colorimetric method, the concentration of byproduct sodium sulfate in the product is measured by a titration method, the concentration of byproduct sodium chloride in the product is measured by a titration method, the concentration of unsulfonate in the product is measured by a petroleum ether extraction method, and the experimental results are shown in the following table:
| Index (I) | Experimental results of examples | Existing kettle type process |
| Appearance of | Clear and transparent | Clear and transparent |
| Color number | No. 40 | 160 |
| Sodium sulfate | 0.75% Before concentration | 1.0% Before concentration |
| Sodium chloride | 0.18％ | 0.2％ |
| Unsulfonate compounds | 0.34％ | 0.5％ |
According to the experimental result analysis based on the two processes, compared with the traditional kettle-type process, the sodium dodecyl diphenyl ether sulfonate product continuously prepared by the method is clear and transparent in appearance, has lower byproduct concentration, good reaction selectivity and higher product yield.
The foregoing is only one preferred embodiment of the invention, and it is intended that any modifications, equivalents, improvements and others which fall within the spirit and principles of the invention are intended to be included within the scope of the invention.
Claims (4)
1. A method for continuously producing sodium dodecyl diphenyl ether sulfonate, which is characterized by comprising the following steps:
(1) The sulfur trioxide solution is used as a sulfonating agent, dodecyl diphenyl ether is used as a base material, and the flow of a metering pump is regulated to ensure that two materials are respectively and continuously conveyed to a pre-cooling pipe for cooling; the sulfur trioxide solution is a dichloroethane solution of sulfur trioxide, and the mass fraction of the sulfur trioxide in the sulfur trioxide solution is 8% -25%; the flow ratio of the sulfur trioxide solution to the dodecyl diphenyl ether fed into the pre-cooling pipe is 4:3-2:1; the target temperature range of the sulfur trioxide solution and the dodecyl diphenyl ether which need to be cooled in the pre-cooling pipe is-15 ℃ to 0 ℃, and the cooling residence time range is 5s to 10s;
(2) Conveying the cooled sulfur trioxide solution and dodecyl diphenyl ether into a micro-inverse mixer for full contact mixing; the molar ratio of the sulfur trioxide in the sulfur trioxide solution to the dodecyl diphenyl ether in the micro-reaction mixer is 1.8-2.3; the micro-inverse mixer is a membrane dispersion micro-mixer;
(3) Delivering the fully mixed materials to a time-delay coil microreactor to perform a first-stage reaction in the sulfonation process; the temperature range of the reaction of the sulfur trioxide solution and the dodecyl diphenyl ether in the delay coil microreactor is-15-0 ℃, and the residence time of the reaction is 7-20 s;
(4) After the reaction liquid finishes the first-stage reaction, the reaction liquid enters an aging kettle for collection; after the ageing kettle collects the reaction liquid with set quality, the reaction liquid is switched to a new ageing kettle for collection; collecting the reaction liquid in the aging kettle, and continuously stirring to enable the reaction liquid to carry out the aging reaction of the second stage of the sulfonation process in the aging kettle; the reaction temperature of the reaction liquid in the aging kettle ranges from 0 ℃ to 15 ℃ and the stirring time ranges from 30min to 80min;
(5) After the aging reaction is finished, the reaction liquid is subjected to hydrolysis, neutralization and concentration treatment to obtain a sodium dodecyl diphenyl ether sulfonate product; wherein, the neutralization process is to add NaOH to neutralize dodecyl diphenyl ether sulfonic acid to prepare sodium dodecyl diphenyl ether sulfonate.
2. The method for continuous production of sodium dodecyl diphenyl ether sulfonate according to claim 1, wherein the temperature of the pre-cooling tube, the micro-inverse mixer and the time-delay coil micro-reactor are controlled by a freezing thermostat.
3. The method for continuous production of sodium dodecyl diphenyl ether sulfonate according to claim 1, wherein in the step (1), the diameter of the pre-cooling pipe ranges from 0.8mm to 4mm.
4. The method for continuous production of sodium dodecyl diphenyl ether sulfonate according to claim 1, wherein in step (3), the tube diameter of the time delay coil microreactor ranges from 0.8mm to 4mm.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211472181.9A CN115745850B (en) | 2022-11-23 | Method for continuous flow production of sodium dodecyl diphenyl ether sulfonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211472181.9A CN115745850B (en) | 2022-11-23 | Method for continuous flow production of sodium dodecyl diphenyl ether sulfonate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115745850A CN115745850A (en) | 2023-03-07 |
| CN115745850B true CN115745850B (en) | 2024-06-04 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103265461A (en) * | 2013-06-13 | 2013-08-28 | 杨锌荣 | Alkyl (sulfophenoxy) benzenesulfonic acid disodiumsalt and preparation method thereof |
| CN107089932A (en) * | 2017-05-26 | 2017-08-25 | 中国日用化学工业研究院 | The process for sulfonation and device of a kind of alkyl diphenyl ether |
| CN110526840A (en) * | 2019-09-19 | 2019-12-03 | 南雄市汉科化工科技有限公司 | Synthesize the preparation process and reaction unit of dodecyl Biphenyl Ether disulfonic acid sodium salt |
| CN111704561A (en) * | 2020-05-18 | 2020-09-25 | 中国日用化学研究院有限公司 | Method for preparing alkyl diphenyl ether sulfonate by sulfonating liquid-phase sulfur trioxide |
| CN113861082A (en) * | 2021-11-12 | 2021-12-31 | 上海昶法新材料有限公司 | Method for synthesizing alkyl diphenyl ether disulfonic acid sodium by micro-channel reactor |
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103265461A (en) * | 2013-06-13 | 2013-08-28 | 杨锌荣 | Alkyl (sulfophenoxy) benzenesulfonic acid disodiumsalt and preparation method thereof |
| CN107089932A (en) * | 2017-05-26 | 2017-08-25 | 中国日用化学工业研究院 | The process for sulfonation and device of a kind of alkyl diphenyl ether |
| CN110526840A (en) * | 2019-09-19 | 2019-12-03 | 南雄市汉科化工科技有限公司 | Synthesize the preparation process and reaction unit of dodecyl Biphenyl Ether disulfonic acid sodium salt |
| CN111704561A (en) * | 2020-05-18 | 2020-09-25 | 中国日用化学研究院有限公司 | Method for preparing alkyl diphenyl ether sulfonate by sulfonating liquid-phase sulfur trioxide |
| CN113861082A (en) * | 2021-11-12 | 2021-12-31 | 上海昶法新材料有限公司 | Method for synthesizing alkyl diphenyl ether disulfonic acid sodium by micro-channel reactor |
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