CS262439B2 - Process for preparing netoxic salts of 6-methyl-3,4- dihydro-1,2,3-oxathiazin-4-on,2,2-dioxide - Google Patents
Process for preparing netoxic salts of 6-methyl-3,4- dihydro-1,2,3-oxathiazin-4-on,2,2-dioxide Download PDFInfo
- Publication number
- CS262439B2 CS262439B2 CS866323A CS632386A CS262439B2 CS 262439 B2 CS262439 B2 CS 262439B2 CS 866323 A CS866323 A CS 866323A CS 632386 A CS632386 A CS 632386A CS 262439 B2 CS262439 B2 CS 262439B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- dioxide
- dihydro
- oxathiazin
- water
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 43
- 238000004519 manufacturing process Methods 0.000 title description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 78
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 78
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 60
- XLXCHZCQTCBUOX-UHFFFAOYSA-N 1-prop-2-enylimidazole Chemical class C=CCN1C=CN=C1 XLXCHZCQTCBUOX-UHFFFAOYSA-N 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 50
- 239000012074 organic phase Substances 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 41
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 40
- 230000008569 process Effects 0.000 claims description 39
- 239000003960 organic solvent Substances 0.000 claims description 31
- 239000000243 solution Substances 0.000 claims description 28
- 238000007363 ring formation reaction Methods 0.000 claims description 24
- 238000000605 extraction Methods 0.000 claims description 21
- QXBGLCSYJYZBFK-UHFFFAOYSA-N 3-oxobutanoylsulfamic acid Chemical compound CC(=O)CC(=O)NS(O)(=O)=O QXBGLCSYJYZBFK-UHFFFAOYSA-N 0.000 claims description 19
- 230000007062 hydrolysis Effects 0.000 claims description 18
- 238000006460 hydrolysis reaction Methods 0.000 claims description 18
- 238000006386 neutralization reaction Methods 0.000 claims description 18
- 239000012071 phase Substances 0.000 claims description 16
- 231100000252 nontoxic Toxicity 0.000 claims description 15
- 230000003000 nontoxic effect Effects 0.000 claims description 15
- 238000001704 evaporation Methods 0.000 claims description 12
- 229910052700 potassium Inorganic materials 0.000 claims description 12
- 239000011591 potassium Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 claims description 9
- 230000008020 evaporation Effects 0.000 claims description 9
- 239000010409 thin film Substances 0.000 claims description 8
- -1 aliphatic chlorinated hydrocarbon Chemical class 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000003049 inorganic solvent Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000010408 film Substances 0.000 claims description 6
- 229910001867 inorganic solvent Inorganic materials 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- HQTYWLJBELLQCX-UHFFFAOYSA-N 6-methyloxathiazin-4-one Chemical class CC1=CC(=O)NSO1 HQTYWLJBELLQCX-UHFFFAOYSA-N 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 239000002585 base Substances 0.000 description 27
- 235000011118 potassium hydroxide Nutrition 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 16
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 14
- AHRFRRASJMTTQU-UHFFFAOYSA-N 6-methyl-2,2-dioxooxathiazin-4-one;potassium Chemical compound [K].CC1=CC(=O)NS(=O)(=O)O1 AHRFRRASJMTTQU-UHFFFAOYSA-N 0.000 description 11
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 11
- 229910052939 potassium sulfate Inorganic materials 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 10
- 235000011151 potassium sulphates Nutrition 0.000 description 10
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 6
- RQIMPDXRFCFBGC-UHFFFAOYSA-N n-(oxomethylidene)sulfamoyl fluoride Chemical compound FS(=O)(=O)N=C=O RQIMPDXRFCFBGC-UHFFFAOYSA-N 0.000 description 6
- 239000001120 potassium sulphate Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 239000000619 acesulfame-K Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- XIMSTDAFGWROBF-UHFFFAOYSA-N oxathiazine 2-oxide Chemical compound O=S1OC=CC=N1 XIMSTDAFGWROBF-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 description 3
- 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
- 238000009835 boiling Methods 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- LFMIQNJMJJKICW-UHFFFAOYSA-N 1,1,2-trichloro-2-fluoroethene Chemical group FC(Cl)=C(Cl)Cl LFMIQNJMJJKICW-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- YKBIDDXCRFTFKT-UHFFFAOYSA-N 6-ethyl-2,2-dioxooxathiazin-4-one Chemical compound CCC1=CC(=O)NS(=O)(=O)O1 YKBIDDXCRFTFKT-UHFFFAOYSA-N 0.000 description 1
- RRBGLZMKJDYZKT-UHFFFAOYSA-N 6-methyl-3,4-dihydrooxathiazine Chemical compound CC1=CCNSO1 RRBGLZMKJDYZKT-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 229910006136 SO4F Inorganic materials 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 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
- 229960005164 acesulfame Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 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
- 230000001351 cycling effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Chemical group 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 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
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 235000007686 potassium 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
- 238000011403 purification operation Methods 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
- 238000007670 refining Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000001043 yellow dye Substances 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| CS632386A2 CS632386A2 (en) | 1988-07-15 |
| CS262439B2 true CS262439B2 (en) | 1989-03-14 |
Family
ID=6279975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS866323A CS262439B2 (en) | 1985-09-03 | 1986-09-01 | Process for preparing netoxic salts of 6-methyl-3,4- dihydro-1,2,3-oxathiazin-4-on,2,2-dioxide |
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 |
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| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF00 | In force as of 2000-06-30 in czech republic | ||
| MK4A | Patent expired |
Effective date: 20010901 |