CN115260124A - Acesulfame potassium composition and method for producing the same - Google Patents
Acesulfame potassium composition and method for producing the same Download PDFInfo
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- 229960004998 acesulfame potassium Drugs 0.000 title claims abstract description 123
- 239000000619 acesulfame-K Substances 0.000 title claims abstract description 123
- 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 115
- 235000010358 acesulfame potassium Nutrition 0.000 title claims abstract description 115
- 239000000203 mixture Substances 0.000 title claims abstract description 114
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 27
- -1 alkali metal salt Chemical class 0.000 claims abstract description 20
- 239000012535 impurity Substances 0.000 claims abstract description 20
- 229960002673 sulfacetamide Drugs 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 44
- 239000000243 solution Substances 0.000 claims description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 25
- 229960005164 acesulfame Drugs 0.000 claims description 22
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 claims description 17
- 239000003513 alkali Substances 0.000 claims description 17
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 claims description 16
- 229910052700 potassium Inorganic materials 0.000 claims description 16
- 239000011591 potassium Substances 0.000 claims description 16
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 15
- GEHMBYLTCISYNY-UHFFFAOYSA-N Ammonium sulfamate Chemical compound [NH4+].NS([O-])(=O)=O GEHMBYLTCISYNY-UHFFFAOYSA-N 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- LNVGRTNYNVXJOP-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-3-oxobutanamide Chemical class CCN(CC)CCNC(=O)CC(C)=O LNVGRTNYNVXJOP-UHFFFAOYSA-N 0.000 claims description 12
- 239000012266 salt solution Substances 0.000 claims description 10
- FNXIDRUUVHQLHR-UHFFFAOYSA-N C(C)(=O)OS(=O)(C1=CC=C(C=C1)N)=O.[K] Chemical compound C(C)(=O)OS(=O)(C1=CC=C(C=C1)N)=O.[K] FNXIDRUUVHQLHR-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- SKIVFJLNDNKQPD-UHFFFAOYSA-N sulfacetamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 SKIVFJLNDNKQPD-UHFFFAOYSA-N 0.000 claims description 9
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 7
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- XCVWCSLKKQOBGY-UHFFFAOYSA-N 2-acetyl-4-aminobenzenesulfonic acid Chemical compound CC(=O)C1=CC(N)=CC=C1S(O)(=O)=O XCVWCSLKKQOBGY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 6
- 239000013078 crystal Substances 0.000 abstract description 4
- 239000012452 mother liquor Substances 0.000 abstract description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 61
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000007864 aqueous solution Substances 0.000 description 9
- YVZOKLTZSNJEQX-UHFFFAOYSA-N 5-chloro-6-methyl-2,2-dioxooxathiazin-4-one Chemical compound CC1=C(Cl)C(=O)NS(=O)(=O)O1 YVZOKLTZSNJEQX-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 6
- 239000012458 free base Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 235000003599 food sweetener Nutrition 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000003765 sweetening agent Substances 0.000 description 3
- ZFUVRGUVFYSKBW-UHFFFAOYSA-N CCN(CC)C(C)CCCNC(CC(C)=O)=O Chemical class CCN(CC)C(C)CCCNC(CC(C)=O)=O ZFUVRGUVFYSKBW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 2
- 229960004306 sulfadiazine Drugs 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VZJMWXOCFUFYSF-UHFFFAOYSA-N CCN(CC)CCNS(C(CC(C)=O)=O)(=O)=O Chemical class CCN(CC)CCNS(C(CC(C)=O)=O)(=O)=O VZJMWXOCFUFYSF-UHFFFAOYSA-N 0.000 description 1
- VFDKGXYVBDLFOS-UHFFFAOYSA-N CCN(CC)CCSC(CC(C)=O)=O Chemical class CCN(CC)CCSC(CC(C)=O)=O VFDKGXYVBDLFOS-UHFFFAOYSA-N 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QQAAKLIAQBPTIG-UHFFFAOYSA-N n,n-diethylethanamine;3-oxobutanamide Chemical compound CCN(CC)CC.CC(=O)CC(N)=O QQAAKLIAQBPTIG-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium peroxide Inorganic materials [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- DQMFXGQHSPWNOA-UHFFFAOYSA-N triethylazanium;sulfamate Chemical compound NS([O-])(=O)=O.CC[NH+](CC)CC DQMFXGQHSPWNOA-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
- C07D291/06—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a acesulfame potassium composition and a method for producing the same, which enables acetoacetyl-sulfacetamide triethylamine salt in a crude acesulfame potassium composition to react under a strong alkaline condition to generate organic alkali metal salt which is easy to dissolve in water, and a small amount of organic alkali metal salt is dissolved in mother liquor in the process of separating out acesulfame potassium crystal, thereby reducing the content of organic impurities in the finished product of acesulfame potassium and improving the product quality.
Description
Technical Field
The invention relates to the technical field of chemical industry, in particular to a potassium sulfacetamide composition and a method for producing the same.
Background
Acesulfame potassium, chemical name 6-methyl-1, 2, 3-thiazine-4 (3) -ketone-2, 2-potassium dioxide, commonly known as Acesulfame potassium, AK sugar (Acesulfame-K). Because the acesulfame potassium has the advantages of safety, no toxicity, stable property, sweet taste, no bad aftertaste, proper price and the like, the acesulfame potassium is one of the sweeteners with the best stability in the world at present and is used as a sweetener in the aspects of food, medicine and the like.
In a conventional acesulfame potassium production process, sulfamic acid is reacted with an amine (e.g., triethylamine) to form an ammonium sulfamate. The ammonium sulfamate is then reacted with diketene to form the acetoacetamidotriethylamine salt. The acesulfame triethylamine salt is cyclized, hydrolyzed and neutralized to form acesulfame potassium. The patent with the application number of 201780001641.0 specifically discloses a production method of acesulfame potassium.
Generally, the acetoacetylsulfanyltriethylamine salt is cyclized by reaction with sulfur trioxide in an inorganic or organic solvent to form a cyclic sulfur trioxide adduct, and the solvent used for the reaction is an organic solvent. The adduct formed by this reaction is then hydrolyzed and then neutralized with potassium hydroxide to form acesulfame potassium.
The acesulfame potassium and intermediate compositions produced by conventional processes contain undesirable impurities, such as acetoacetanilide triethylamine salt that has not reacted with sulfur trioxide, which can be carried into the aqueous acesulfame potassium solution, and during the subsequent crystallization of acesulfame potassium, the residual acetoacetanilide triethylamine salt can wrap on the surface of acesulfame potassium crystals, resulting in high content of organic impurities in the finished acesulfame potassium product, which affects the product quality. For these impurities that are difficult to remove using standard purification procedures such as evaporation, crystallization or filtration, there is a need for a process that further improves the impurity content for producing high purity acesulfame potassium compositions.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a acesulfame potassium composition and a method for producing the same, so that the acesulfame potassium triethylamine salt in the crude acesulfame potassium composition reacts under the strong alkaline condition to generate organic alkali metal salt which is easy to dissolve in water, and a small amount of organic alkali metal salt is dissolved in mother liquor in the process of separating out acesulfame potassium crystals, thereby reducing the content of organic impurities in acesulfame potassium finished products and improving the product quality.
In order to solve the technical problems, the invention adopts a technical scheme that:
a process for producing a potassium sulfacetamide composition comprising the steps of:
(1) Providing a crude acesulfame potassium composition comprising acesulfame potassium, acetoacetanilide triethylamine salt, and water;
(2) Reacting the crude acesulfame potassium composition under alkaline conditions to form a acesulfame potassium composition;
(3) Concentrating and separating the intermediate acesulfame potassium composition to form a refined acesulfame potassium composition comprising acesulfame potassium and less than 15ppm of acetoacetamide;
wherein, the content of free alkali in the step (2) is adjusted to be 0.01-1 moL/L.
Preferably, the free base content of the crude acesulfame potassium composition in step (1) is 10-5～10-4.5moL/L。
Further preferably, the crude acesulfame potassium composition in step (2) is reacted with a KOH solution to form a acesulfame potassium composition.
Preferably, the weight percentage of the KOH solution is 6 to 10 percent.
More preferably, the mass percentage of the KOH solution is 7 to 9 percent.
Preferably, the reaction temperature of the step (2) is 20-30 ℃.
Preferably, the reaction residence time in the step (2) is 1-30 min.
Preferably, the refined acesulfame potassium composition further comprises less than 10ppm of 5-chloro-acesulfame potassium.
Preferably, the refined acesulfame potassium composition contains less than 25ppm of organic impurities.
Preferably, the color value of the refined acesulfame potassium composition is less than 0.5Hazen.
Preferably, the crude acesulfame potassium composition is connected to the mixer sequentially through a pump a and a mass flow meter a; the KOH solution passes through a pump b and a mass flow meter b in sequence and is connected with a mixer.
Further preferably, the mixer comprises a tank reactor, a tube reactor or a microchannel reactor.
Preferably, the content of free base in step (2) is adjusted to 0.1 to 1moL/L.
Preferably, step (1) comprises:
reacting sulfamic acid with triethylamine to form an ammonium sulfamate solution;
reacting an ammonium sulfamate solution with diketene to form an acetoacetamidotriethylamine salt solution;
reacting the acetoacetamidotriethylamine salt solution with sulfur trioxide in the cyclizing agent composition to form a cyclic sulfur trioxide adduct;
hydrolyzing the cyclic sulfur trioxide adduct to form an acesulfame H composition;
reacting the acesulfame H in the acesulfame H composition with a base to form a crude acesulfame potassium composition.
Preferably, the process for the production of the acesulfame potassium composition comprises the steps of:
(1) Reacting sulfamic acid with triethylamine to form an ammonium sulfamate solution;
(2) Reacting an ammonium sulfamate solution with diketene to form an acetoacetamidotriethylamine salt solution;
(3) Reacting the acetoacetamidotriethylamine salt solution with sulfur trioxide in the cyclizing agent composition to form a cyclic sulfur trioxide adduct;
(4) Hydrolyzing the cyclic sulfur trioxide adduct to form an acetyl sulfanilic acid H composition;
(5) Reacting the acesulfame H in the acesulfame H composition with a base to form a crude acesulfame potassium composition comprising acesulfame potassium, acesulfame triethylamine salt, and water;
(6) Reacting the crude acesulfame potassium composition with KOH solution to form an acesulfame potassium composition, and adjusting the content of free alkali to 0.01-1 moL/L;
(7) The intermediate acesulfame potassium composition is concentrated and isolated to form a refined acesulfame potassium composition comprising acesulfame potassium and less than 15ppm of acetoacetamide.
Further preferably, the free base content of the crude acesulfame potassium composition in step (5) is 10-5～10- 4.5moL/L。
Preferably, the content of free base in the step (6) is adjusted to 0.1 to 1moL/L.
Preferably, the mass percentage of the KOH solution is 6 to 10 percent.
More preferably, the mass percentage of the KOH solution is 7 to 9 percent.
Preferably, the reaction temperature of the step (2) is 20-30 ℃.
Preferably, the reaction residence time in step (2) is 1 to 30min.
Preferably, the refined acesulfame potassium composition further comprises less than 10ppm of 5-chloro-acesulfame potassium.
Preferably, the refined acesulfame potassium composition contains less than 25ppm of organic impurities.
Preferably, the color value of the refined acesulfame potassium composition is less than 0.5Hazen.
The invention also provides a refined acesulfame potassium composition produced by the above method.
Preferably, it comprises acesulfame potassium and less than 15ppm of acetoacetamide.
Preferably, it comprises less than 10ppm of acetoacetamide.
Preferably, it comprises less than 10ppm of 5-chloro-acesulfame potassium.
Preferably, it contains less than 25ppm of organic impurities.
Preferably, the chroma value is less than 0.5Hazen.
Due to the adoption of the technical scheme, compared with the prior art, the invention has the following advantages:
the invention makes the acetyl sulfacetamide triethylamine salt in the crude potassium sulfacetamide composition react under the strong alkaline condition to generate the organic alkali metal salt which is easy to dissolve in water, and a small amount of the organic alkali metal salt is dissolved in the mother liquor in the process of precipitating the potassium sulfacetamide crystal, thereby reducing the content of organic impurities in the finished product of the potassium sulfacetamide and improving the product quality.
Drawings
FIG. 1 is a flow diagram of the dosing of a crude acesulfame potassium composition with KOH solution.
Detailed Description
The invention is further described in detail below with reference to the drawings and specific embodiments.
A process for producing a potassium sulfacetamide composition comprising the steps of:
ammonium sulfamate formation reaction
In a first reaction step, sulfamic acid is reacted with an amine to form an ammonium sulfamate. An exemplary reaction mechanism using triethylamine as the amine and producing triethylammonium sulfamate is shown in reaction (1) below.
The amine may also be selected from the group consisting of trimethylamine, tri-n-butylamine, triisobutylamine, triisopropylamine and mixtures thereof.
Acetylsulfacetamide salt formation reaction
The ammonium sulfamate is reacted with an acetoacetylating agent to form acetoacetamidotriethylamine salt, preferably acetoacetamide-N-sulfonic acid triethylammonium salt. The acetoacetylating agent comprises diketene.
An exemplary reaction mechanism for forming acetoacetamidotriethylamine salt uses acetoacetamide-N-sulfonate triethylammonium salt and diketene as reactants and produces acetoacetamide triethylammonium salt, which is shown in reaction (2) below.
The ammonium sulfamate-forming reaction and the acetoacetamidotriethylamine salt-forming reaction may use an organic solvent, preferably dichloromethane, chloroform, trichloroethylene, acetone, glacial acetic acid, and a mixture thereof.
Cyclization and hydrolysis
Reacting acetoacetanilide triethylamine salt with a cyclizing agent in the presence of a solvent to form a cyclic sulfur trioxide adduct composition comprising a cyclic sulfur trioxide adduct and in some cases impurities, e.g., not with SO3Acetyl sulfacetamide triethylamine salt which generates cyclization reaction.
An exemplary cyclization reaction using sulfur trioxide as a cyclizing agent is shown in the following reaction (3).
The solvent used for the cyclization reaction is preferably dichloromethane, acetone, glacial acetic acid, trichloroethylene and mixtures thereof.
The cyclic sulfur trioxide adduct can be hydrolyzed via conventional means (e.g., using water). Hydrolyzing the cyclic sulfur trioxide adduct to form the acesulfame H composition. An exemplary hydrolysis reaction mechanism is shown in reaction (4) below.
The addition of water results in phase separation. The majority of the sweetener acid is present in the organic phase.
Neutralization
Neutralization of the acesulfame H with a base in the acesulfame H composition produces a crude acesulfame potassium composition. The base is preferably KOH, KHCO3，K2CO3And potassium alkoxides. An exemplary reaction mechanism using potassium hydroxide as a neutralizing agent is shown in the following reaction (5).
The crude acesulfame potassium composition comprises acesulfame potassium, water and unreacted SO3Acetyl sulfadoxyl triethylamine salt which has cyclization reaction. To reduce or eliminate unwanted impurities, such as acetoacetamidopropyl triethylamine salt, the acetoacetamidopropyl triethylamine salt in the crude acesulfame potassium composition is reacted under strongly basic conditions to form the acesulfame potassium composition. The potassium mesosulfacetamide composition comprises acetoacetamide-N-sulfonate. The base is preferably KOH. An exemplary reaction mechanism of acetoacetylsulfonamido triethylamine salt with potassium hydroxide is shown in the following reaction (5).
FIG. 1 shows a flow diagram of the formulation of a crude acesulfame potassium composition with KOH solution. The crude acesulfame potassium composition is connected with a mixer through a pump a and a mass flow meter a in sequence; the KOH solution sequentially passes through a pump b and a mass flow meter b to be connected with the mixer, and the mesosulfacetamide potassium composition flows out of the outlet of the mixer to enter the next step.
Preferably, the crude acesulfame potassium composition has a free base content of 10-5～10-4.5moL/L, 6-10% of KOH solution, 0.1-1 moL/L of free alkali content when the two solutions react, 20-30 ℃ of reaction temperature and 1-30 min of reaction residence time.
Concentrating and separating
The intermediate acesulfame potassium composition is concentrated, decolorized, and recrystallized via evaporation to form a refined acesulfame potassium composition comprising acesulfame potassium and less than 25ppm of organic impurities, further comprising less than 15ppm of acetoacetamide and less than 10ppm of acetoacetamide. The color value of the refined acesulfame potassium composition is less than 0.5Hazen.
The crude acesulfame potassium composition is formed by taking dichloromethane as a solvent, performing neutralization reaction on sulfamic acid and triethylamine, and performing acylation reaction on a neutralized solution and diketene to prepare an acesulfame triethylamine salt solution. The acetyl sulfanilic triethylamine salt solution and methylene dichloride solution of sulfur trioxide are subjected to cyclization, and then hydrolysis reaction is carried out on the product and water. The acid layer after hydrolysis is extracted by dichloromethane, extracted dichloromethane containing 3-5% of acesulfame H is neutralized by 6-10% of potassium hydroxide solution at 20-30 ℃, the free alkali content of the neutralized solution is controlled, and after delamination, crude acesulfame potassium composition aqueous solution with the free alkali content of 10-5-10-4.5 moL/L is obtained.
Example 1
Mixing the crude potassium acetylsulfanilate composition aqueous solution with 7 percent by mass of KOH solution in a microchannel mixer, wherein the reaction temperature is 20 ℃, and the retention time is 1min. After being uniformly mixed, the content of free alkali in the acesulfame potassium aqueous solution is 0.1moL/L, after evaporation concentration, decoloration and recrystallization, the chromatic value of the refined acesulfame potassium composition is 0.2Hazen, the content of acesulfame potassium is 99.45 percent, the content of acetoacetamide is 9.2ppm, the content of 5-chloro-acesulfame potassium is 5.5ppm, and the content of organic impurities is 18ppm.
Example 2
Mixing the crude potassium acetylsulfanilate composition aqueous solution with 9 percent by mass of KOH solution in a tubular mixer, wherein the reaction temperature is 30 ℃, and the retention time is 30min. After being uniformly mixed, the content of free alkali in the acesulfame potassium aqueous solution is 1moL/L, after evaporation concentration, decoloration and recrystallization, the chromatic value of the refined acesulfame potassium composition is 0.1Hazen, the content of acesulfame potassium is 99.5 percent, the content of acetoacetamide is 8.6ppm, the content of 5-chloro-acesulfame potassium is 4.8ppm, and the content of organic impurities is 16ppm.
Example 3
Mixing the crude potassium acetylsulfanilate composition aqueous solution with 8 percent of KOH solution by mass percent in a kettle type mixer, reacting at the temperature of 25 ℃, and stoppingThe retention time is 15min. After being mixed evenly, the content of free alkali in the potassium acetylsulfanilate aqueous solution is 10-0.5moL/L, evaporating, concentrating, decolorizing and recrystallizing, wherein the chroma value of the refined acesulfame potassium composition is 0.1Hazen, the content of acesulfame potassium is 99.47 percent, the content of acetoacetamide is 8.9ppm, the content of 5-chloro-acesulfame potassium is 5.1ppm, and the content of organic impurities is 17ppm.
Comparative example 1
The extracted methylene chloride containing 3% of acesulfame H from the previous step was mixed with 10% potassium hydroxide solution in a tubular mixer at 30 ℃ for 15min. After layering, the content of free alkali in the acesulfame potassium water solution is 10-4.5moL/L, after evaporation concentration, decoloration and recrystallization, the chromatic value of the refined potassium acetylsulfanilate composition is 10Hazen, the content of the potassium acetylsulfanilate is 99.24 percent, the content of the acetoacetamide is 53.2ppm, the content of the 5-chloro-acesulfame potassium is 4.8ppm, and the content of organic impurities is 87ppm.
Comparative example 2
The extracted dichloromethane containing 5% acesulfame H from the previous step was mixed with 6% potassium hydroxide solution in a kettle mixer at 25 deg.C for 20min. After layering, the content of free alkali in the potassium sulfadiazine aqueous solution is 10-5moL/L, after evaporation concentration, decoloration and recrystallization, the chromatic value of the refined potassium acetylsulfanilate composition is 20Hazen, the content of the potassium acetylsulfanilate is 99.03 percent, the content of the acetoacetamide is 97.1ppm, the content of the 5-chloro-acesulfame potassium is 5.5ppm, and the content of organic impurities is 134ppm.
Comparative example 3
The extracted dichloromethane containing 4% acesulfame H from the previous step was mixed with 8% potassium hydroxide solution in a kettle mixer at 25 deg.C for 5min. After layering, the content of free alkali in the potassium sulfadiazine aqueous solution is 10-4.8moL/L, evaporating, concentrating, decolorizing, recrystallizing to obtain refined acesulfame potassium composition with chroma value of 15Hazen, acesulfame potassium content of 99.12%, acetoacetamide content of 79.1ppm, 5-chloro-acetoacetylThe content of potassium is 5.9ppm and the content of organic impurities is 120ppm.
The present invention has been described in detail, and the embodiments are only used for understanding the method and the core idea of the present invention, and the purpose of the present invention is to enable those skilled in the art to understand the content of the present invention and to implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (19)
1. A process for producing a potassium sulfacetamide composition characterized by: the method comprises the following steps:
(1) Providing a crude acesulfame potassium composition comprising acesulfame potassium, acesulfame triethylamine salt and water;
(2) Reacting the crude acesulfame potassium composition under alkaline conditions to form an acesulfame potassium composition;
(3) Concentrating and isolating the potassium mesosulfacetamide composition to form a refined potassium sulfacetamide composition comprising potassium sulfacetamide and less than 15ppm of acetoacetamide;
wherein, the content of free alkali in the step (2) is adjusted to be 0.01-1 moL/L.
2. The process for the production of acesulfame potassium composition according to claim 1, characterized in that: the content of free alkali in the crude acesulfame potassium composition in the step (1) is 10-5～10-4.5moL/L。
3. The process for the production of acesulfame potassium composition according to claim 2, characterized in that: reacting the crude acesulfame potassium composition in step (2) with a KOH solution to form a acesulfame potassium composition.
4. The process for the production of acesulfame potassium composition according to claim 3, characterized in that: the KOH solution accounts for 6 to 10 percent by mass.
5. The process for the production of acesulfame potassium composition according to claim 4, characterized in that: the KOH solution accounts for 7 to 9 percent by mass.
6. The process for the production of acesulfame potassium composition according to claim 3, characterized in that: the crude potassium acetylsulfanilate composition sequentially passes through a pump a and a mass flow meter a and is connected with a mixer; and the KOH solution sequentially passes through a pump b and a mass flow meter b and is connected with the mixer.
7. The process for the production of acesulfame potassium composition according to claim 6, characterized in that: the mixer comprises a tank reactor, a tubular reactor or a microchannel reactor.
8. The process for the production of acesulfame potassium composition according to claim 1, characterized in that: in the step (2), the content of free alkali is adjusted to be 0.1-1 moL/L.
9. The process for the production of acesulfame potassium composition according to claim 1, characterized in that: the step (1) comprises the following steps:
reacting sulfamic acid with triethylamine to form an ammonium sulfamate solution;
reacting the ammonium sulfamate solution with diketene to form an acetoacetamidotriethylamine salt solution;
reacting the acetoacetamidotriethylamine salt solution with sulfur trioxide in a cyclizing agent composition to form a cyclic sulfur trioxide adduct;
hydrolyzing the cyclic sulfur trioxide adduct to form an acetyl sulfanilic acid H composition;
reacting the acesulfame H in the acesulfame H composition with a base to form a crude acesulfame potassium composition.
10. The process for the production of acesulfame potassium composition according to claim 1, characterized in that: the method comprises the following steps:
(1) Reacting sulfamic acid with triethylamine to form an ammonium sulfamate solution;
(2) Reacting the ammonium sulfamate solution with diketene to form an acetoacetamidotriethylamine salt solution;
(3) Reacting the acetoacetamidotriethylamine salt solution with sulfur trioxide in a cyclizing agent composition to form a cyclic sulfur trioxide adduct;
(4) Hydrolyzing the cyclic sulfur trioxide adduct to form an acesulfame H composition;
(5) Reacting acesulfame H in the acesulfame H composition with a base to form a crude acesulfame potassium composition comprising acesulfame potassium, acesulfame triethylamine salt and water;
(6) Reacting the crude acesulfame potassium composition with a KOH solution to form an acesulfame potassium composition, and adjusting the content of free alkali to 0.01-1 moL/L;
(7) Concentrating and separating the intermediate acesulfame potassium composition to form a refined acesulfame potassium composition comprising acesulfame potassium and less than 15ppm of acetoacetamide.
11. The process for the production of acesulfame potassium composition according to claim 10, characterized in that: the content of free alkali in the crude acesulfame potassium composition in the step (5) is 10-5～10-4.5moL/L。
12. The process for the production of acesulfame potassium composition according to claim 10, characterized in that: in the step (6), the content of free alkali is adjusted to be 0.1-1 moL/L.
13. The process for the production of acesulfame potassium composition according to claim 10, characterized in that: the KOH solution accounts for 6 to 10 percent by mass.
14. The process for the production of acesulfame potassium composition according to claim 13, characterized in that: the KOH solution accounts for 7 to 9 percent by mass.
15. The refined acesulfame potassium composition produced by the process of claim 10.
16. The acesulfame potassium composition of claim 15, wherein: comprising acesulfame potassium and less than 15ppm of acetoacetamide.
17. The acesulfame potassium composition of claim 16, wherein: comprising less than 10ppm of acetoacetamide.
18. The acesulfame potassium composition of claim 15, where: contains less than 25ppm of organic impurities.
19. The acesulfame potassium composition of claim 15, wherein: the chroma value is less than 0.5Hazen.
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