WO2022246864A1 - Procédé de traitement d'un liquide résiduaire d'acésulfame de potassium - Google Patents
Procédé de traitement d'un liquide résiduaire d'acésulfame de potassium Download PDFInfo
- Publication number
- WO2022246864A1 WO2022246864A1 PCT/CN2021/097012 CN2021097012W WO2022246864A1 WO 2022246864 A1 WO2022246864 A1 WO 2022246864A1 CN 2021097012 W CN2021097012 W CN 2021097012W WO 2022246864 A1 WO2022246864 A1 WO 2022246864A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- waste liquid
- liquid
- reaction
- triethylamine
- acesulfame potassium
- Prior art date
Links
- 239000007788 liquid Substances 0.000 title claims abstract description 108
- 239000002699 waste material Substances 0.000 title claims abstract description 75
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 title claims abstract description 51
- 235000010358 acesulfame potassium Nutrition 0.000 title claims abstract description 51
- 239000000619 acesulfame-K Substances 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 51
- 229960004998 acesulfame potassium Drugs 0.000 title claims abstract description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 168
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 85
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 60
- 239000000463 material Substances 0.000 claims abstract description 46
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 36
- 239000000047 product Substances 0.000 claims abstract description 33
- 239000012074 organic phase Substances 0.000 claims abstract description 30
- 238000000926 separation method Methods 0.000 claims abstract description 27
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims abstract description 24
- 235000011130 ammonium sulphate Nutrition 0.000 claims abstract description 24
- 239000012043 crude product Substances 0.000 claims abstract description 23
- 239000012071 phase Substances 0.000 claims abstract description 21
- 238000001704 evaporation Methods 0.000 claims abstract description 20
- 230000008020 evaporation Effects 0.000 claims abstract description 15
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 57
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 32
- 239000008346 aqueous phase Substances 0.000 claims description 23
- 238000011084 recovery Methods 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 18
- 229960005164 acesulfame Drugs 0.000 claims description 15
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 claims description 15
- 230000035484 reaction time Effects 0.000 claims description 11
- 239000012535 impurity Substances 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 238000003672 processing method Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 238000002360 preparation method Methods 0.000 abstract description 3
- 238000004064 recycling Methods 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 22
- 229910021529 ammonia Inorganic materials 0.000 description 12
- JNONJXMVMJSMTC-UHFFFAOYSA-N hydron;triethylazanium;sulfate Chemical compound OS(O)(=O)=O.CCN(CC)CC JNONJXMVMJSMTC-UHFFFAOYSA-N 0.000 description 9
- 230000008569 process Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000005416 organic matter Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- -1 form amine sulfamic acid salt Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 2
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- 241001391944 Commicarpus scandens Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004060 metabolic process Effects 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
- 239000010815 organic waste Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000021092 sugar substitutes Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C1/00—Ammonia; Compounds thereof
- C01C1/24—Sulfates of ammonium
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
- C01C1/00—Ammonia; Compounds thereof
- C01C1/24—Sulfates of ammonium
- C01C1/242—Preparation from ammonia and sulfuric acid or sulfur trioxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/86—Separation
Definitions
- the remaining waste water mainly contains amine sulfate, sulfuric acid, impurities Organic matter, including a small amount of triethylamine, solvents, by-products, etc., this part of the wastewater can be discharged after treatment; but on the one hand, this will generate a lot of treatment costs, on the other hand, the amines in the wastewater have high economic value, and are discharged Caused a waste of resources.
- acesulfame potassium waste liquid is the waste liquid produced by adopting diketene-sulfur trioxide method to prepare acesulfame potassium, comprising:
- the above method also includes:
- Residual liquid recovery step mix the residual liquid generated in the product separation step into the waste liquid of acesulfame potassium.
- the beneficial effects of the present application are: firstly, by heating, the content of water in the acesulfame waste liquid is controlled, and then the liquid ammonia is reacted with the sulfate and sulfuric acid of the amine in the waste liquid in a closed environment. The reaction is completed quickly. Compared with other methods of using ammonia to recover amine, the conversion rate of triethylamine sulfate is high, and the reaction is carried out more thoroughly. After the reaction, the crude amine product, crude ammonium sulfate product and the aqueous phase containing complex components are subsequently The treatment is convenient; the acesulfame potassium waste liquid treatment process is greatly simplified, the treatment time is shortened, and the recovery efficiency of amine is significantly improved.
- Water evaporating step S110 Evaporating the acesulfame potassium waste liquid at a first preset temperature until the water content reaches the preset water content to obtain the first material.
- the acesulfame potassium waste liquid in this application is the waste liquid produced by the preparation of acesulfame potassium by diketene-sulfur trioxide method. Taking triethylamine as a catalyst, there is a sulfate of triethylamine in the acesulfame potassium waste liquid , sulfuric acid, impurity organics (such as triethylamine, solvents, by-products), and water.
- triethylamine exists as a catalyst. In the whole preparation process, the amount of triethylamine is not consumed. At the end of the reaction, triethylamine is almost completely converted into triethylamine sulfate, and there is A small amount of triethylamine remains in the impurity organic matter.
- the application does not limit the water evaporation temperature.
- the acesulfame potassium waste liquid in order to evaporate the water as soon as possible, can be evaporated in a boiling state.
- Neutralization reaction step S120 adding liquid ammonia to the first material, and performing a neutralization reaction in a closed reactor to obtain a second material.
- liquid ammonia is used to neutralize the acesulfame-K waste liquid in a closed reactor, and there are sulfates of triethylamine, sulfuric acid, impurity organic matter and water in the first material. Liquid ammonia reacts with triethylamine sulfate to generate triethylamine and ammonium sulfate, and reacts with sulfuric acid to generate ammonium sulfate.
- the present application adopts airtight container to carry out the reaction.
- the reaction there are gas phase and liquid phase reaction at the same time, which is beneficial to increase the reaction rate, the amine conversion rate is high, and the reaction proceeds more thoroughly.
- step S130 separating the second material into an organic phase and an aqueous phase; performing solid-liquid separation on the aqueous phase to obtain a crude ammonium sulfate product and residual liquid; recovering the organic phase as a crude triethylamine product.
- the product is separated, that is, the second material is separated into an organic phase and an aqueous phase.
- the separation process can adopt any one of the prior art, such as static separation.
- the organic phase mainly contains triethylamine and solvent, and the solvent can be evaporated to obtain triethylamine with higher purity.
- a solvent distillation step can be performed before the water evaporation step: at the second preset temperature, distill the acesulfame potassium waste liquid to remove the solvent therein; and A preset temperature is lower than a second preset temperature.
- the solvent is removed before the water evaporates.
- the reaction rate is increased.
- the organic phase obtained after the waste liquid treatment is completed does not contain solvent, which reduces the trouble of post-treatment.
- the second preset temperature may be lower than the first preset temperature.
- the second preset temperature may be set according to the type of solvent.
- the water phase product mainly includes ammonium sulfate and the residual liquid. There is a small amount of triethylamine dissolved in the residual liquid, and some other impurities. Ammonium sulfate is solid, so the aqueous phase is separated from the solid and liquid, and then Ammonium sulfate crude product and residual liquid were obtained.
- the application first controls the content of water in the acesulfame waste liquid by heating, then reacts the sulphate and sulfuric acid of the amine in the liquid ammonia and the waste liquid in a closed environment, due to the gas phase Liquid phase reaction exists at the same time, so that the reaction is completed quickly.
- the conversion rate of triethylamine sulfate is high, and the reaction is carried out more thoroughly.
- the crude amine product, ammonium sulfate crude product and The subsequent treatment of the aqueous phase of complex components is convenient; the treatment process of acesulfame potassium waste liquid is greatly simplified, the treatment time is shortened, and the recovery efficiency of amines is significantly improved.
- the source of acesulfame-K waste liquid is that the factory adopts the diketene-sulfur trioxide method in the prior art to prepare acesulfame-K.
- the acesulfame potassium waste liquid includes 10-30wt% sulfuric acid, 5-20wt% triethylamine sulfate and 3-5wt% impurity organic matter, and the rest is water.
- the organic phase can be cooled to 80-85°C in a closed reactor and then distilled at atmospheric pressure, and the distillate can be used as the crude product of triethylamine Recycle.
- acesulfame potassium is prepared by diketene-sulfur trioxide method, and the aqueous phase and organic phase are separated after the salt-forming step, wherein the aqueous phase is the waste liquid that needs to be treated in this application.
- the mass of sulfuric acid The fraction is 10-30%
- the mass fraction of triethylamine sulfate is 5-20%
- the mass fraction of impurity organic components is 3-5%
- the balance is water, wherein the triethylamine:sulfate molar ratio is 2:4 -1.
- the waste acesulfame potassium used was obtained by this method, and if otherwise specified, it was obtained according to the instructions.
- Embodiment 2 (including embodiment 2A, embodiment 2B, embodiment 2C, embodiment 2D, embodiment 2E)
- Product separation step after the neutralization reaction, cool to normal temperature, distill the second material under normal pressure, distill off excess ammonia and the solvent remaining in the second material; then separate the second material into organic phase and water phase; wherein, the organic phase is recovered as a crude product of triethylamine; the aqueous phase is filtered to separate the solid and liquid to obtain the crude ammonium sulfate product and residual liquid.
- Product separation step after the neutralization reaction, cool to normal temperature, distill the second material under normal pressure, distill off excess ammonia and the solvent remaining in the second material; then separate the second material into organic phase and water phase; wherein, the organic phase is recovered as a crude product of triethylamine; the aqueous phase is filtered to separate the solid and liquid to obtain the crude ammonium sulfate product and residual liquid.
- Product separation step after the neutralization reaction, cool to normal temperature, distill the second material under normal pressure, distill off excess ammonia and the solvent remaining in the second material; then separate the second material into organic phase and water phase; wherein, the organic phase is recovered as a crude product of triethylamine; the aqueous phase is filtered to separate the solid and liquid to obtain the crude ammonium sulfate product and residual liquid.
- the calculation method of the recovery rate of triethylamine the percentage of the molar amount of recovered triethylamine to the molar amount of triethylamine in the acesulfame waste liquid measured before treatment.
- the reaction time of feeding liquid ammonia at room temperature is long, and the conversion rate of reaction products is relatively low.
- Heating under airtight conditions has fast reaction speed and high conversion rate, and can effectively recover triethylamine.
- the recovery of triethylamine reflects a high economic value, and on the other hand, it reduces the difficulty of subsequent treatment of organic waste; after the separation of triethylamine, the remaining waste liquid continues to be recycled, reducing the final waste liquid discharge.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La présente invention concerne un procédé de traitement d'un liquide résiduaire d'acésulfame de potassium, c'est-à-dire un liquide résiduaire produit pendant la préparation de l'acésulfame de potassium par un procédé dicétène-trioxyde de soufre, et le procédé comprend les étapes suivantes : une étape d'évaporation de l'humidité : à une première température prédéfinie, l'évaporation du liquide résiduaire d'acésulfame de potassium jusqu'à ce que la teneur en eau atteigne une teneur en eau prédéfinie, de façon à obtenir une première substance ; une étape de réaction de neutralisation : l'ajout d'ammoniac liquide à la première substance, puis sa soumission à une réaction de neutralisation dans un réacteur fermé, de façon à obtenir une seconde substance ; une étape de séparation de produit : la séparation de la seconde substance en une phase organique et en une phase aqueuse, et la soumission de la phase aqueuse à une séparation solide-liquide, de façon à obtenir un produit brut de sulfate d'ammonium et un liquide résiduel ; et le recyclage de la phase organique en tant que produit brut de triéthylamine.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2021/097012 WO2022246864A1 (fr) | 2021-05-28 | 2021-05-28 | Procédé de traitement d'un liquide résiduaire d'acésulfame de potassium |
| CN202180001423.3A CN113614062B (zh) | 2021-05-28 | 2021-05-28 | 安赛蜜废液的处理方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2021/097012 WO2022246864A1 (fr) | 2021-05-28 | 2021-05-28 | Procédé de traitement d'un liquide résiduaire d'acésulfame de potassium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2022246864A1 true WO2022246864A1 (fr) | 2022-12-01 |
Family
ID=78310956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CN2021/097012 WO2022246864A1 (fr) | 2021-05-28 | 2021-05-28 | Procédé de traitement d'un liquide résiduaire d'acésulfame de potassium |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN113614062B (fr) |
| WO (1) | WO2022246864A1 (fr) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102822139A (zh) * | 2010-04-19 | 2012-12-12 | 国际人造丝公司 | 采用活塞流反应器从废硫酸回收有机叔胺的方法 |
| CN103097297A (zh) * | 2010-04-19 | 2013-05-08 | 国际人造丝公司 | 制备铵盐的方法 |
| CN112010758A (zh) * | 2020-09-26 | 2020-12-01 | 安徽金禾实业股份有限公司 | 一种三乙胺回收方法 |
| CN112142602A (zh) * | 2019-06-27 | 2020-12-29 | 南通醋酸化工股份有限公司 | 一种乙酰磺胺酸钾废酸连续处理方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2377813B1 (fr) * | 2010-04-19 | 2014-12-31 | Celanese International Corporation | Procédé de fabrication d'une composition de sulfure d'ammonium |
| CN112194293A (zh) * | 2020-09-26 | 2021-01-08 | 安徽金禾实业股份有限公司 | 一种安赛蜜生产中外排母液的回收利用方法 |
-
2021
- 2021-05-28 CN CN202180001423.3A patent/CN113614062B/zh active Active
- 2021-05-28 WO PCT/CN2021/097012 patent/WO2022246864A1/fr active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102822139A (zh) * | 2010-04-19 | 2012-12-12 | 国际人造丝公司 | 采用活塞流反应器从废硫酸回收有机叔胺的方法 |
| CN103097297A (zh) * | 2010-04-19 | 2013-05-08 | 国际人造丝公司 | 制备铵盐的方法 |
| CN112142602A (zh) * | 2019-06-27 | 2020-12-29 | 南通醋酸化工股份有限公司 | 一种乙酰磺胺酸钾废酸连续处理方法 |
| CN112010758A (zh) * | 2020-09-26 | 2020-12-01 | 安徽金禾实业股份有限公司 | 一种三乙胺回收方法 |
Non-Patent Citations (1)
| Title |
|---|
| XUE ZHANGHUI, YONG LI, XIAOPING CHEN, WEILI SONG, WEIYI HUANG: "The Operation Evaluation and Optimization on Wastewater Treatment Process of Acesulfame-K", GUANGDONG CHEMICAL INDUSTRY, GUANGDONG-SHENG ZHONGHUA GONGYETING,, CN, 31 December 2010 (2010-12-31), CN , XP093009223, ISSN: 1007-1865 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113614062B (zh) | 2023-12-08 |
| CN113614062A (zh) | 2021-11-05 |
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