CA1043786A - Process for the manufacture of the potassium salt of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide - Google Patents
Process for the manufacture of the potassium salt of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxideInfo
- Publication number
- CA1043786A CA1043786A CA231,605A CA231605A CA1043786A CA 1043786 A CA1043786 A CA 1043786A CA 231605 A CA231605 A CA 231605A CA 1043786 A CA1043786 A CA 1043786A
- Authority
- CA
- Canada
- Prior art keywords
- potassium
- dioxide
- methanol
- sulfofluoride
- potassium salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims abstract description 12
- XLXCHZCQTCBUOX-UHFFFAOYSA-N 1-prop-2-enylimidazole Chemical compound C=CCN1C=CN=C1 XLXCHZCQTCBUOX-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 87
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims abstract description 8
- XIMSTDAFGWROBF-UHFFFAOYSA-N oxathiazine 2-oxide Chemical compound O=S1OC=CC=N1 XIMSTDAFGWROBF-UHFFFAOYSA-N 0.000 claims abstract description 7
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 10
- 239000011698 potassium fluoride Substances 0.000 claims description 6
- 235000003270 potassium fluoride Nutrition 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 229940057952 methanol Drugs 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract description 4
- 238000007363 ring formation reaction Methods 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000019605 sweet taste sensations Nutrition 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 235000003599 food sweetener Nutrition 0.000 description 7
- 239000003765 sweetening agent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 235000011118 potassium hydroxide Nutrition 0.000 description 6
- 229940093932 potassium hydroxide Drugs 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229960003975 potassium Drugs 0.000 description 4
- 235000007686 potassium Nutrition 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 2
- 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 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Seasonings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2434548A DE2434548C2 (de) | 1974-07-18 | 1974-07-18 | Verfahren zur Herstellung von Fluoridarmem 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid-kalium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1043786A true CA1043786A (en) | 1978-12-05 |
Family
ID=5920894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA231,605A Expired CA1043786A (en) | 1974-07-18 | 1975-07-16 | Process for the manufacture of the potassium salt of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3969347A (enExample) |
| JP (1) | JPS597711B2 (enExample) |
| AT (1) | AT344718B (enExample) |
| BE (1) | BE831524R (enExample) |
| CA (1) | CA1043786A (enExample) |
| CH (1) | CH581643A5 (enExample) |
| DE (1) | DE2434548C2 (enExample) |
| DK (1) | DK134644C (enExample) |
| FR (1) | FR2278692A2 (enExample) |
| GB (1) | GB1460540A (enExample) |
| IE (1) | IE41268B1 (enExample) |
| IT (1) | IT1049563B (enExample) |
| LU (1) | LU72994A1 (enExample) |
| NL (1) | NL179730C (enExample) |
| ZA (1) | ZA754390B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4256730A (en) * | 1978-08-24 | 1981-03-17 | The Procter & Gamble Company | Oral compositions |
| JPS59154957A (ja) * | 1983-02-21 | 1984-09-04 | Takeda Chem Ind Ltd | 甘味料組成物および甘味付与方法 |
| DE3429039A1 (de) * | 1984-08-07 | 1986-02-20 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nichttoxischen salzen |
| DE3531358A1 (de) * | 1985-09-03 | 1987-03-12 | Hoechst Ag | Verfahren zur herstellung der nicht-toxischen salze des 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxids |
| JP2008037777A (ja) * | 2006-08-03 | 2008-02-21 | Daicel Chem Ind Ltd | ３，４−ジヒドロ−１，２，３−オキサチアジン−４−オン−２，２−ジオキサイド化合物のカリウム塩の製造方法 |
| SI3322695T2 (sl) | 2016-09-21 | 2025-08-29 | Celanese International Corporation | Sestavki kalijevega acesulfama in postopki za njihovo izdelavo |
| EP3319948B1 (en) | 2016-09-21 | 2021-06-30 | Celanese International Corporation | Acesulfame potassium compositions and processes for producing same |
| JP6818896B2 (ja) | 2016-09-21 | 2021-01-27 | セラニーズ・インターナショナル・コーポレーション | アセスルファムカリウム組成物及びその製造方法 |
| HUE051396T2 (hu) | 2016-09-21 | 2021-03-01 | Celanese Int Corp | Aceszulfám-kálium kompozíciók és az elõállításukra szolgáló eljárások |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2001017C3 (de) * | 1970-01-10 | 1978-05-18 | Hoechst Ag, 6000 Frankfurt | 3,4-Dihydro-1,23-oxathiazin-4on-2,2-dioxide, ihre Herstellung und Verwendung |
| DE2264235C3 (de) * | 1972-12-30 | 1980-09-11 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-l,23-oxa thiazin-4-on-2,2-dioxid |
-
1974
- 1974-07-18 DE DE2434548A patent/DE2434548C2/de not_active Expired
-
1975
- 1975-07-09 ZA ZA00754390A patent/ZA754390B/xx unknown
- 1975-07-14 NL NLAANVRAGE7508390,A patent/NL179730C/xx not_active IP Right Cessation
- 1975-07-15 CH CH924775A patent/CH581643A5/xx not_active IP Right Cessation
- 1975-07-16 IT IT25480/75A patent/IT1049563B/it active
- 1975-07-16 AT AT548875A patent/AT344718B/de not_active IP Right Cessation
- 1975-07-16 CA CA231,605A patent/CA1043786A/en not_active Expired
- 1975-07-16 JP JP50086253A patent/JPS597711B2/ja not_active Expired
- 1975-07-16 US US05/596,217 patent/US3969347A/en not_active Expired - Lifetime
- 1975-07-16 LU LU72994A patent/LU72994A1/xx unknown
- 1975-07-17 IE IE1590/75A patent/IE41268B1/xx unknown
- 1975-07-17 DK DK326875A patent/DK134644C/da active
- 1975-07-17 GB GB3002275A patent/GB1460540A/en not_active Expired
- 1975-07-17 FR FR7522317A patent/FR2278692A2/fr active Granted
- 1975-07-18 BE BE158431A patent/BE831524R/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| DK134644C (da) | 1977-05-16 |
| CH581643A5 (enExample) | 1976-11-15 |
| JPS5134182A (en) | 1976-03-23 |
| IE41268B1 (en) | 1979-11-21 |
| DK134644B (da) | 1976-12-13 |
| FR2278692A2 (fr) | 1976-02-13 |
| ATA548875A (de) | 1977-12-15 |
| AU8315675A (en) | 1977-01-20 |
| NL179730C (nl) | 1986-11-03 |
| NL179730B (nl) | 1986-06-02 |
| US3969347A (en) | 1976-07-13 |
| DE2434548C2 (de) | 1982-11-18 |
| FR2278692B2 (enExample) | 1978-10-13 |
| BE831524R (fr) | 1976-01-19 |
| NL7508390A (nl) | 1976-01-20 |
| JPS597711B2 (ja) | 1984-02-20 |
| DK326875A (da) | 1976-01-19 |
| ZA754390B (en) | 1976-06-30 |
| DE2434548A1 (de) | 1976-01-29 |
| LU72994A1 (enExample) | 1977-03-21 |
| GB1460540A (en) | 1977-01-06 |
| AT344718B (de) | 1978-08-10 |
| IE41268L (en) | 1976-01-18 |
| IT1049563B (it) | 1981-02-10 |
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