CA1283913C - Process for the preparation of 6-methyl-3,4-dihydro-1, 2,3-oxathiazin-4-one 2,2-dioxide and for the purification thereof - Google Patents
Process for the preparation of 6-methyl-3,4-dihydro-1, 2,3-oxathiazin-4-one 2,2-dioxide and for the purification thereofInfo
- Publication number
- CA1283913C CA1283913C CA000517246A CA517246A CA1283913C CA 1283913 C CA1283913 C CA 1283913C CA 000517246 A CA000517246 A CA 000517246A CA 517246 A CA517246 A CA 517246A CA 1283913 C CA1283913 C CA 1283913C
- Authority
- CA
- Canada
- Prior art keywords
- dihydro
- methyl
- dioxide
- oxathiazin
- aqueous
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 64
- 230000008569 process Effects 0.000 title claims abstract description 61
- XLXCHZCQTCBUOX-UHFFFAOYSA-N 1-prop-2-enylimidazole Chemical compound C=CCN1C=CN=C1 XLXCHZCQTCBUOX-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 238000000746 purification Methods 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 53
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 49
- 239000012074 organic phase Substances 0.000 claims abstract description 46
- 229910001868 water Inorganic materials 0.000 claims abstract description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000003960 organic solvent Substances 0.000 claims abstract description 37
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 24
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 20
- 238000000605 extraction Methods 0.000 claims abstract description 17
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 17
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 17
- QXBGLCSYJYZBFK-UHFFFAOYSA-N 3-oxobutanoylsulfamic acid Chemical compound CC(=O)CC(=O)NS(O)(=O)=O QXBGLCSYJYZBFK-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003049 inorganic solvent Substances 0.000 claims abstract description 7
- 229910001867 inorganic solvent Inorganic materials 0.000 claims abstract description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 61
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 56
- 239000000243 solution Substances 0.000 claims description 31
- 239000012071 phase Substances 0.000 claims description 29
- 229940032330 sulfuric acid Drugs 0.000 claims description 23
- 230000007062 hydrolysis Effects 0.000 claims description 22
- 238000006460 hydrolysis reaction Methods 0.000 claims description 22
- 238000001704 evaporation Methods 0.000 claims description 13
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 claims description 12
- -1 aliphatic chlorinated hydrocarbon Chemical class 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000010409 thin film Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229910052700 potassium Inorganic materials 0.000 claims description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
- 230000003472 neutralizing effect Effects 0.000 claims description 8
- 239000011591 potassium Substances 0.000 claims description 8
- 238000007792 addition Methods 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 230000008020 evaporation Effects 0.000 claims description 6
- 239000011552 falling film Substances 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 4
- 230000002226 simultaneous effect Effects 0.000 claims 1
- HQTYWLJBELLQCX-UHFFFAOYSA-N 6-methyloxathiazin-4-one Chemical compound CC1=CC(=O)NSO1 HQTYWLJBELLQCX-UHFFFAOYSA-N 0.000 abstract description 8
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 abstract description 2
- 235000003599 food sweetener Nutrition 0.000 abstract description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract description 2
- 239000003765 sweetening agent Substances 0.000 abstract description 2
- 239000002585 base Substances 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 229940073584 methylene chloride Drugs 0.000 description 16
- 239000000047 product Substances 0.000 description 12
- 235000011118 potassium hydroxide Nutrition 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 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 10
- 239000007858 starting material Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229910052939 potassium sulfate Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- RQIMPDXRFCFBGC-UHFFFAOYSA-N n-(oxomethylidene)sulfamoyl fluoride Chemical compound FS(=O)(=O)N=C=O RQIMPDXRFCFBGC-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RRBGLZMKJDYZKT-UHFFFAOYSA-N 6-methyl-3,4-dihydrooxathiazine Chemical compound CC1=CCNSO1 RRBGLZMKJDYZKT-UHFFFAOYSA-N 0.000 description 4
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- USPTVMVRNZEXCP-UHFFFAOYSA-N sulfamoyl fluoride Chemical compound NS(F)(=O)=O USPTVMVRNZEXCP-UHFFFAOYSA-N 0.000 description 3
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 2
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DINUECIUIXLUTO-UHFFFAOYSA-O C[S+](N1)OC=CC1=O Chemical compound C[S+](N1)OC=CC1=O DINUECIUIXLUTO-UHFFFAOYSA-O 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000011403 purification operation Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 2
- 235000019605 sweet taste sensations Nutrition 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical group ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000003631 expected effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- JELWTDFYWODDQR-UHFFFAOYSA-N oxathiazin-4-one Chemical compound O=C1NSOC=C1 JELWTDFYWODDQR-UHFFFAOYSA-N 0.000 description 1
- XIMSTDAFGWROBF-UHFFFAOYSA-N oxathiazine 2-oxide Chemical class O=S1OC=CC=N1 XIMSTDAFGWROBF-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 239000001120 potassium sulphate Substances 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- QARNHIBOPBXNSX-UHFFFAOYSA-N prop-1-enoxymethylbenzene Chemical compound CC=COCC1=CC=CC=C1 QARNHIBOPBXNSX-UHFFFAOYSA-N 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Seasonings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3531358.7 | 1985-09-03 | ||
| DE19853531358 DE3531358A1 (de) | 1985-09-03 | 1985-09-03 | Verfahren zur herstellung der nicht-toxischen salze des 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1283913C true CA1283913C (en) | 1991-05-07 |
Family
ID=6279975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000517246A Expired - Lifetime CA1283913C (en) | 1985-09-03 | 1986-08-29 | Process for the preparation of 6-methyl-3,4-dihydro-1, 2,3-oxathiazin-4-one 2,2-dioxide and for the purification thereof |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4804755A (Direct) |
| EP (1) | EP0218076B1 (Direct) |
| JP (1) | JPS6256481A (Direct) |
| KR (1) | KR940008749B1 (Direct) |
| CN (1) | CN1008736B (Direct) |
| AR (1) | AR248016A1 (Direct) |
| AT (1) | ATE49201T1 (Direct) |
| AU (1) | AU587855B2 (Direct) |
| BR (1) | BR8604201A (Direct) |
| CA (1) | CA1283913C (Direct) |
| CS (1) | CS262439B2 (Direct) |
| DD (1) | DD249272A5 (Direct) |
| DE (2) | DE3531358A1 (Direct) |
| DK (1) | DK168045B1 (Direct) |
| ES (1) | ES2000617A6 (Direct) |
| FI (1) | FI83077C (Direct) |
| HU (1) | HU200758B (Direct) |
| IE (1) | IE59132B1 (Direct) |
| IL (1) | IL79894A (Direct) |
| MX (1) | MX173526B (Direct) |
| NO (1) | NO163856C (Direct) |
| SU (1) | SU1582988A3 (Direct) |
| ZA (1) | ZA866647B (Direct) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE3531359A1 (de) * | 1985-09-03 | 1987-03-12 | Hoechst Ag | Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid sowie zu dessen reinigung |
| TW223067B (Direct) * | 1992-03-17 | 1994-05-01 | Hoechst Ag | |
| DE10253773B3 (de) * | 2002-11-19 | 2004-06-24 | Nutrinova Nutrition Specialties & Food Ingredients Gmbh | Verwendung von Acesulfamsäure zur pH-Wert-Absenkung |
| JP2005263779A (ja) * | 2004-02-17 | 2005-09-29 | 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又はその塩の製造法 |
| JP2008037778A (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又はその塩の製造法 |
| 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 |
| US9024016B2 (en) | 2012-06-08 | 2015-05-05 | Nutrinova Nutrition Specialists & Food Ingredients GmbH | Process for producing acesulfame potassium |
| JP6912582B2 (ja) | 2016-09-21 | 2021-08-04 | 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 |
| EP3623363A1 (en) | 2016-09-21 | 2020-03-18 | Celanese International Corporation | Acesulfame potassium compositions and processes for producing same |
| CN119192099A (zh) | 2016-09-21 | 2024-12-27 | 国际人造丝公司 | 乙酰舒泛钾组合物和用于生产其的方法 |
| SI3319949T1 (sl) * | 2016-09-21 | 2020-11-30 | Celanese International Corporation, | Sestavki kalijevega acesulfama in postopki za njihovo izdelavo |
| CN109369572A (zh) * | 2018-10-25 | 2019-02-22 | 苏州浩波科技股份有限公司 | 一种安赛蜜的纯化工艺 |
| CN109593071A (zh) * | 2018-12-10 | 2019-04-09 | 安徽金禾实业股份有限公司 | 一种连续可控的安赛蜜重结晶离心装置及方法 |
| CN112424176A (zh) * | 2020-09-21 | 2021-02-26 | 安徽金禾实业股份有限公司 | 安赛蜜的精制方法 |
| CN116568674A (zh) * | 2021-12-31 | 2023-08-08 | 安徽金禾实业股份有限公司 | 一种对含有乙酰磺胺酸的水解反应产物的处理方法和装置 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2327804C3 (de) * | 1973-06-01 | 1980-08-14 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von 3,4-Dihydro-l,23-oxathiazin-4-onen |
| DE2434548C2 (de) * | 1974-07-18 | 1982-11-18 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Fluoridarmem 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid-kalium |
| DE2453063A1 (de) * | 1974-11-08 | 1976-05-13 | Hoechst Ag | Verfahren zur herstellung von acetoacetamid-n-sulfofluorid |
| DE3410439A1 (de) * | 1984-03-22 | 1985-09-26 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nichttoxischen salzen sowie der dabei als zwischenprodukt(e) auftretenden acetoacetamind-n-sulfonsaeure(salze) |
| DE3410440A1 (de) * | 1984-03-22 | 1985-09-26 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nichttoxischen salzen |
| DE3531359A1 (de) * | 1985-09-03 | 1987-03-12 | Hoechst Ag | Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid sowie zu dessen reinigung |
-
1985
- 1985-09-03 DE DE19853531358 patent/DE3531358A1/de not_active Withdrawn
-
1986
- 1986-08-27 AT AT86111841T patent/ATE49201T1/de not_active IP Right Cessation
- 1986-08-27 EP EP86111841A patent/EP0218076B1/de not_active Expired - Lifetime
- 1986-08-27 DE DE8686111841T patent/DE3667972D1/de not_active Expired - Lifetime
- 1986-08-29 CA CA000517246A patent/CA1283913C/en not_active Expired - Lifetime
- 1986-08-29 US US06/902,427 patent/US4804755A/en not_active Expired - Lifetime
- 1986-09-01 HU HU863764A patent/HU200758B/hu not_active IP Right Cessation
- 1986-09-01 ES ES8601536A patent/ES2000617A6/es not_active Expired
- 1986-09-01 IL IL79894A patent/IL79894A/xx not_active IP Right Cessation
- 1986-09-01 CS CS866323A patent/CS262439B2/cs not_active IP Right Cessation
- 1986-09-01 DD DD86294054A patent/DD249272A5/de not_active IP Right Cessation
- 1986-09-01 FI FI863523A patent/FI83077C/fi not_active IP Right Cessation
- 1986-09-01 SU SU864028038A patent/SU1582988A3/ru active
- 1986-09-02 ZA ZA866647A patent/ZA866647B/xx unknown
- 1986-09-02 AU AU62173/86A patent/AU587855B2/en not_active Expired
- 1986-09-02 BR BR8604201A patent/BR8604201A/pt not_active IP Right Cessation
- 1986-09-02 IE IE234486A patent/IE59132B1/en not_active IP Right Cessation
- 1986-09-02 NO NO863504A patent/NO163856C/no not_active IP Right Cessation
- 1986-09-02 CN CN86105877A patent/CN1008736B/zh not_active Expired
- 1986-09-02 JP JP61205245A patent/JPS6256481A/ja active Granted
- 1986-09-02 DK DK418186A patent/DK168045B1/da not_active IP Right Cessation
- 1986-09-03 MX MX003636A patent/MX173526B/es unknown
- 1986-09-03 KR KR1019860007363A patent/KR940008749B1/ko not_active Expired - Lifetime
- 1986-09-11 AR AR86305109A patent/AR248016A1/es active
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