Acesulfame

Base Information

• Chemical Name: Acesulfame
• CAS No.: 33665-90-6
• Molecular Formula: C4H5NO4S
• Molecular Weight: 163.154
• Hs Code.: 2934999090
• European Community (EC) Number: 259-715-3,251-622-6
• UNII: MA3UYZ6K1H
• DSSTox Substance ID: DTXSID0048006
• Nikkaji Number: J19.735A,J2.157.851G
• Wikipedia: Acesulfame_potassium
• Wikidata: Q2823822
• NCI Thesaurus Code: C76511
• RXCUI: 1310546
• Metabolomics Workbench ID: 46118
• ChEMBL ID: CHEMBL176687
• Mol file: 33665-90-6.mol

Synonyms:acesulfam-K;acesulfame calcium;acesulfame K;acesulfame potassium;acesulfame sodium;acetosulfam;acetosulfam potassium;acetosulfam, potassium salt;acetosulfam, sodium salt;acetosulfame;acetosulfame calcium

Chemical Property of Acesulfame

Chemical Property:

• Melting Point: 123-123.5°
• PKA: -0.28±0.40(Predicted)
• PSA: 80.85000
• Density: 1.512 g/cm³
• LogP: 0.69100
• Water Solubility.: 270 g/L at 20 ºC
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 162.99392881
• Heavy Atom Count: 10
• Complexity: 283

Purity/Quality:

99% ^*data from raw suppliers

Acesulfame K for food analysis, ≥99.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: CC1=CC(=O)NS(=O)(=O)O1
• Recent ClinicalTrials: Effects of Oral Xylitol on Subsequent Energy Intake
• Recent NIPH Clinical Trials: Effects of tastant on salivation flow.
• Description: Acesulfame pottasium (also known as acesulfame K or Ace K) is a calorie free sugar substitute (artificial sweetener). It is ~ 200x sweeter than table sugar and approved for use in food as a non-nutritive sweetener. It is sold under the brand names Sunett? and Sweet One?. FDA approved it as a general purpose sweetener and flavor enhancer in food, except in meat and poultry, under certain conditions of use. It stays sweet even when used at high temperatures during baking, making it suitable as a sugar substitute in baked goods. Acesulfame potassium has been approved for use in a variety of food products including frozen desserts, candies, beverages, baby food, and baked goods. More than 90 studies support its safety. Acesulfame K contains the carcinogen methylene chloride. Long-term exposure to methylene chloride can cause headaches, depression, nausea, mental confusion, liver effects, kidney effects, visual disturbances, and cancer in humans.
• Uses: 1. Non-nutritional sweetener, being able to be widely used in various foods, even in drinks of Ph3.0, it can also be used. 2. For beverages, food, health products and so on 3. Food sweeteners 4. Acesulfame belongs to the fourth generation synthetic sweeteners with single administration accompanied with a certain bitter taste. It has a synergistic effect when being used in combination with aspartame or cyclamate and being able to mask the bitter taste. After intake of the human body, it is not absorbed and does not produce heat, being suitable for patients with diabetes and obesity. It can be used as pastry, jam (excluding canned food), pickles, candy, candied fruit, beverage, ice cream and jelly candy with the maximum dosage of 0.3g/kg; it can also be used as table sweetener (flake or powder) with 40 mg per tablet or per packet. Acesulfame-K is a non-nutritive sweetener also termed acesulfame potassium. it is a white, crystalline product that is 200 times sweeter than sucrose. it is not metabolized in the body. it has some metallic off-tastes. it is readily soluble and heat and acid stable. it provides a synergistic sweetening effect combined with other sweeteners. it is used in beverages, desserts, confectionery, and bakery products.
• Production method: There are many patents on the preparation of acesulfame, here are four methods. Aminosulfonic acid and diketene method Take aminosulfonic acid, triethylamine, diketene and potassium hydroxide as raw material for synthesis. 9.7 g (0.1 mol) of sulfamic acid was added to 16 mL (0.12 mol) of triethylamine and stirred until complete dissolution. 8 mL 0.104 mol of diketene was added drop wise at 0 ° C, and the mixture was stirred at room temperature until completion of the reaction. Add hexane for precipitation and further refinement and the solvent was removed under reduced pressure to obtain 27 to 28 g of a syrup in a yield of 95.7 to 99.0%. The slurry and SO3 were simultaneously added to the container containing CH2Cl2 for stirring continuously of 1-5 hours before the removal of solvent under reduced pressure. The residue was treated with methanol-potassium hydroxide solution under controlling Ph value of 8 to 10. The solvent was removed and dried to give acesulfame potassium salt in 69% yield. This method is easy to obtain raw materials with mild conditions but the process is complex and the yield is not high. Aminosulfonyl fluoride and diketene method. To a solution of 76 g (0.55 mol) of potassium carbonate powder and 500 mL of acetone, 57.8 mL (1.0 mol) of sulfamic acid fluoride was added, and 84.3 mL (1.1 mol) of diketene was added dropwise over 15 min. Stir for reaction at 0 °C for 30 min. The reaction is exothermic with the temperature be controlled below 30℃ until the CO2 is completely released before stopping the reaction. The reaction mixture was suction filtered and washed with a small amount of acetone to give the potassium salt of the colorless crystalline acetoacetylamino-N-sulfonyl fluoride. The crystal was stirred together with 4 to 6 mol of methanol-potassium hydroxide solution to cyclize to obtain the acesulfame potassium salt in a yield of 93% of the theoretical amount. This method is easier to obtain raw materials with mild process conditions. The operation is also not complicated, being the ideal preparation method. Acetoacetamide and fluorinated sulfuryl fluoride method. Take acetoacetamide, potassium carbonate, fluorinated sulfuryl fluoride and potassium hydroxide as raw materials; (0.1 mol) of acetoacetamide and 69 g (0.5 mol) of potassium carbonate were added to 150 mL of acetone and 8 mL of water. After stirring uniformly, 15.3 g (0.15 mol) of fluorinated sulfuryl fluoride gas was introduced at room temperature for reaction at which point the reaction mixture was allowed to warm to 40 ° C and stirred for 2 h before suction filtration. The filter cake was put into an excess of hydrochloric acid solution of ice to dissolve and react. And then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain acesulfame. It will react with methanol-potassium hydroxide solution to obtain acesulfame potassium salt with drying to get 14.1 g finished product with the yield of 86.5% of the theoretical amount. This method is not harsh reaction conditions, the yield is high, but some raw materials are not easy to get. Acetoacetamide and sulfur trioxide method. In an inert organic or inorganic solvent, send through SO3 into acetoacetamide for recycling condensation, generating acetoacetyl sulfamic acid. After separation, it is reacted with potassium hydroxide to derive the products. Dissolve 5.1 g (50 mmol) acetoacetamide in 50mLCH2Cl2; dissolve 8 mL (200 mmo1) liquid SO3 in 50 mL Mlch2Cl2; then at-60 ℃, then drop the former one to the latter for stirring reaction of 2h. Add 50 mL acetoacetamide and water and the organic phase was separated after extraction and further subject to aqueous phase extraction with ethyl acetate for twice and combined into the organic phase. After drying over anhydrous sodium sulfate, ethyl acetate was recovered by evaporation. The residue was dissolved in methanol and neutralized with methanol-potassium hydroxide solution. Acesulfame potassium salt was then precipitated and dried, yielding 3.1 g of product in a yield of 31% of the theoretical amount. This method needs to be carried out at low temperature, and the yield is not high. It can be obtained through the addition reaction of fluorosulfonyl isocyanate (or chlorosulfonyl isocyanate) with various active methylene compounds (including α-unsubstituted ketone, β-diketone, β-keto acid and β-ketoester, etc.) addition . For example, from the addition reaction between tert-butyl acetoacetate and fluorosulfonyl isocyanate.

Technology Process of Acesulfame

There total 10 articles about Acesulfame which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

1,2-bis(6-methyl-2,2-dioxido-4-oxo-1,2,3-oxathiazin-3(4H)-yl)ethane-1,2-dione → carbon dioxide (124-38-9,18923-20-1) + carbon monoxide (201230-82-2) + acetosulfam (33665-90-6)

Guidance literature:

With water; In acetonitrile; at 37 ℃; for 1h;

DOI:10.1039/d1sc02711e

Reference yield: 86.0%

6-methyl-2,3-dihydro-1,3-oxazin-2,4-dione-3-sulfo-fluoride → acetosulfam (33665-90-6)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone;

Reference yield: 58.0%

→ acetosulfam (33665-90-6)

Guidance literature:

upstream raw materials:

Triethylammoniumsalz der Acetoacetamid-N-sulfonsaeure

acetoacetamido

fluorosulfonylchloride

potassium acesulfame

Downstream raw materials:

potassium acesulfame

benzene

C₁₄H₁₃BiN₂O₈S₂

C₁₆H₁₄BiNO₄S

Refernces

• 1、 Baran, Enrique J.,Echeverría, Gustavo A.,Parajón-Costa, Beatriz S.,Piro, Oscar E.. "A new acesulfamato complex: [Cu(acesulfamato)2(H2O)4]. Structural and spectroscopic characterization". . . Retrieved 2020.
• 2、 Surov, Artem O.,Voronin, Alexander P.,Simagina, Anna A.,Churakov, Andrei V.,Perlovich, German L.. "Pharmaceutical salts of biologically active hydrazone compound salinazid: Crystallographic, solubility, and thermodynamic aspects". . p. 2605 - 2617. Retrieved 2016.
• 3、 Echeverria, Gustavo A.,Piro, Oscar E.,Parajon-Costa, Beatriz S.,Baran, Enrique J.. "Synthesis and characterization of ammonium acesulfamate". . p. 737 - 741. Retrieved 2014.
• 4、 Brewer, Maya,Cachuela, Alyssa,De La Cruz, Ladie Kimberly,Gallo, David,Ji, Xingyue,Lu, Wen,Menshikh, Anna,Otterbein, Leo,Tan, Chalet,Wang, Binghe,Wang, Minjia,Wang, Siming,Yang, Haichun,Yang, Xiaoxiao,de Caestecker, Mark. "Adapting decarbonylation chemistry for the development of prodrugs capable ofin vivodelivery of carbon monoxide utilizing sweeteners as carrier molecules". . p. 10649 - 10654. Retrieved 2021/08/20.