DE3429039A1 - Verfahren zur herstellung von6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nichttoxischen salzen - Google Patents
Verfahren zur herstellung von6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nichttoxischen salzenInfo
- Publication number
- DE3429039A1 DE3429039A1 DE19843429039 DE3429039A DE3429039A1 DE 3429039 A1 DE3429039 A1 DE 3429039A1 DE 19843429039 DE19843429039 DE 19843429039 DE 3429039 A DE3429039 A DE 3429039A DE 3429039 A1 DE3429039 A1 DE 3429039A1
- Authority
- DE
- Germany
- Prior art keywords
- acetoacetamide
- methyl
- dioxide
- bases
- dihydro
- 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.)
- Withdrawn
Links
- 150000003839 salts Chemical class 0.000 title claims description 15
- 231100000252 nontoxic Toxicity 0.000 title claims description 8
- 230000003000 nontoxic effect Effects 0.000 title claims description 8
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 claims description 21
- 239000002585 base Substances 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 5
- 150000004679 hydroxides Chemical class 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 239000003701 inert diluent Substances 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- XLXCHZCQTCBUOX-UHFFFAOYSA-N 1-prop-2-enylimidazole Chemical compound C=CCN1C=CN=C1 XLXCHZCQTCBUOX-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- WBZFUFAFFUEMEI-UHFFFAOYSA-M Acesulfame k Chemical compound [K+].CC1=CC(=O)[N-]S(=O)(=O)O1 WBZFUFAFFUEMEI-UHFFFAOYSA-M 0.000 description 7
- 239000005935 Sulfuryl fluoride Substances 0.000 description 7
- 239000000619 acesulfame-K Substances 0.000 description 7
- -1 amidosulfonic acid halide Chemical class 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- RQIMPDXRFCFBGC-UHFFFAOYSA-N n-(oxomethylidene)sulfamoyl fluoride Chemical compound FS(=O)(=O)N=C=O RQIMPDXRFCFBGC-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-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
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- MBIWGMSRIYVQHE-UHFFFAOYSA-N S(=O)(=O)(N=C=O)N=C=O.[F] Chemical compound S(=O)(=O)(N=C=O)N=C=O.[F] MBIWGMSRIYVQHE-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960005164 acesulfame Drugs 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 2
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 239000003049 inorganic solvent Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XIMSTDAFGWROBF-UHFFFAOYSA-N oxathiazine 2-oxide Chemical compound O=S1OC=CC=N1 XIMSTDAFGWROBF-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- IXPAAHZTOUOJJM-UHFFFAOYSA-N sulfuryl chloride fluoride Chemical compound FS(Cl)(=O)=O IXPAAHZTOUOJJM-UHFFFAOYSA-N 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- SNDGLCYYBKJSOT-UHFFFAOYSA-N 1,1,3,3-tetrabutylurea Chemical compound CCCCN(CCCC)C(=O)N(CCCC)CCCC SNDGLCYYBKJSOT-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 1
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 1
- AXWKFRWLYPZEFQ-UHFFFAOYSA-N 3-oxobutanoyl chloride Chemical compound CC(=O)CC(Cl)=O AXWKFRWLYPZEFQ-UHFFFAOYSA-N 0.000 description 1
- QXBGLCSYJYZBFK-UHFFFAOYSA-N 3-oxobutanoylsulfamic acid Chemical compound CC(=O)CC(=O)NS(O)(=O)=O QXBGLCSYJYZBFK-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
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 229910006024 SO2Cl2 Inorganic materials 0.000 description 1
- 229910006095 SO2F Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 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
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000004049 embossing Methods 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 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 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000004321 preservation Methods 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003672 ureas Chemical class 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)
- Plural Heterocyclic Compounds (AREA)
- Seasonings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843429039 DE3429039A1 (de) | 1984-08-07 | 1984-08-07 | Verfahren zur herstellung von6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nichttoxischen salzen |
| AT85109376T ATE36851T1 (de) | 1984-08-07 | 1985-07-25 | Verfahren zur herstellung von 6-methyl-3,4dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nicht-toxischen salzen. |
| EP85109376A EP0173082B1 (de) | 1984-08-07 | 1985-07-25 | Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nicht-toxischen Salzen |
| DE8585109376T DE3564682D1 (en) | 1984-08-07 | 1985-07-25 | Process for the preparation of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide and its non-toxic salts |
| HU852963A HU197889B (en) | 1984-08-07 | 1985-08-02 | Process for preparing 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxide and its alkali metal or trialkyl ammonium salts |
| FI853008A FI81790C (fi) | 1984-08-07 | 1985-08-05 | Foerfarande foer framstaellning av 6-metyl-3,4-dihydro-1,2,3-oxatiazin-4-on-2,2-dioxid och dess icke-toxiska salter. |
| AR301184A AR240454A1 (es) | 1984-08-07 | 1985-08-05 | Procedimiento para la preparacion de 6-metil-3,4-dihidro-1,2,3-oxatiazin-4-on-2,2-dioxido y de sus sales no toxicas. |
| US06/762,563 US4625024A (en) | 1984-08-07 | 1985-08-05 | Process for the preparation of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide and its non-toxic salts |
| SU853933056A SU1491338A3 (ru) | 1984-08-07 | 1985-08-05 | Способ получени 6-метил-3,4-дигидро-1,2,3-оксатиазин-4-он-2,2-диоксида или его калиевой соли |
| ES545878A ES8604186A1 (es) | 1984-08-07 | 1985-08-05 | Procedimiento para la preparacion de 6-metil-3,4-dihidro- 1,2,3-oxatiazin-4-on-2,2-dioxido y de sus sales no toxicas |
| DD85279371A DD246298A5 (de) | 1984-08-07 | 1985-08-05 | Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nicht-toxischen salzen |
| KR1019850005654A KR920008617B1 (ko) | 1984-08-07 | 1985-08-06 | 6-메틸-3,4-디하이드로-1,2,3-옥사티아진-4-온2,2-디옥사이드 및 이의 무독성 염의 제조방법 |
| DK358285A DK167976B1 (da) | 1984-08-07 | 1985-08-06 | Fremgangsmaade til fremstilling af 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid eller dettes ikke-toksiske salte |
| AU45835/85A AU575669B2 (en) | 1984-08-07 | 1985-08-06 | Process for the preparation of 6-methyl-3,4-dihydro-1,2,3- oxathiazin-4-one 2,2-dioxide |
| IE194085A IE58482B1 (en) | 1984-08-07 | 1985-08-06 | Process for the preparation of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide and its non-toxic salts |
| ZA855921A ZA855921B (en) | 1984-08-07 | 1985-08-06 | Process for the preparation of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide and its non-toxic salts |
| NO853103A NO163772C (no) | 1984-08-07 | 1985-08-06 | Fremgangsmaate til fremstilling av 6-metyl-3,4-dihydro-1,2,3-oksatiazin-4-on-2,2-dioksyd og dets ikke-toksiske salter |
| IL76027A IL76027A (en) | 1984-08-07 | 1985-08-06 | Process for the preparation of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide and its non-toxic salts |
| BR8503715A BR8503715A (pt) | 1984-08-07 | 1985-08-06 | Processo para a preparacao de 2,2-dioxido de 6-metil-3,4-dihiro-1,2,3-oxatizin-4-ona e seus sais atoxicos |
| JP60171936A JPS6147473A (ja) | 1984-08-07 | 1985-08-06 | ６―メチル―３，４―ジヒドロ―１，２，３―オキサチアジン―４―オン―２，２―ジオキシド及びその無毒の塩の製法 |
| CA000488177A CA1241955A (en) | 1984-08-07 | 1985-08-06 | Process for the preparation of 6-methyl-3,4-dihydro-1, 2,3-oxathiazin-4-one 2,2-dioxide and its non-toxic salts |
| MX206223A MX160726A (es) | 1984-08-07 | 1985-08-07 | Procedimiento para la preparacion de 6-metil-3,4-dihidro-1,2,3-oxatiazin-4-on-2,2-di oxido y sus sales no toxicas |
| CN85106284A CN1007979B (zh) | 1984-08-07 | 1985-08-20 | 2，2-二氧化6-甲基-3，4-二氢-1，2，3-噻嗪-4-酮及其无毒盐的制法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843429039 DE3429039A1 (de) | 1984-08-07 | 1984-08-07 | Verfahren zur herstellung von6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nichttoxischen salzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3429039A1 true DE3429039A1 (de) | 1986-02-20 |
Family
ID=6242506
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843429039 Withdrawn DE3429039A1 (de) | 1984-08-07 | 1984-08-07 | Verfahren zur herstellung von6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nichttoxischen salzen |
| DE8585109376T Expired DE3564682D1 (en) | 1984-08-07 | 1985-07-25 | Process for the preparation of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide and its non-toxic salts |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8585109376T Expired DE3564682D1 (en) | 1984-08-07 | 1985-07-25 | Process for the preparation of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide and its non-toxic salts |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4625024A (https=) |
| EP (1) | EP0173082B1 (https=) |
| JP (1) | JPS6147473A (https=) |
| KR (1) | KR920008617B1 (https=) |
| AR (1) | AR240454A1 (https=) |
| AT (1) | ATE36851T1 (https=) |
| AU (1) | AU575669B2 (https=) |
| BR (1) | BR8503715A (https=) |
| CA (1) | CA1241955A (https=) |
| DD (1) | DD246298A5 (https=) |
| DE (2) | DE3429039A1 (https=) |
| DK (1) | DK167976B1 (https=) |
| ES (1) | ES8604186A1 (https=) |
| FI (1) | FI81790C (https=) |
| HU (1) | HU197889B (https=) |
| IE (1) | IE58482B1 (https=) |
| IL (1) | IL76027A (https=) |
| MX (1) | MX160726A (https=) |
| NO (1) | NO163772C (https=) |
| SU (1) | SU1491338A3 (https=) |
| ZA (1) | ZA855921B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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) |
| HUE051396T2 (hu) | 2016-09-21 | 2021-03-01 | Celanese Int Corp | Aceszulfám-kálium kompozíciók és az elõállításukra szolgáló eljárások |
| LT3319948T (lt) | 2016-09-21 | 2021-10-11 | Celanese International Corporation | Kalio acesulfamo kompozicijos ir jų gamybos būdai |
| US10030000B2 (en) | 2016-09-21 | 2018-07-24 | Celanese International Corporation | Acesulfame potassium compositions and processes for producing same |
| EP3623363A1 (en) | 2016-09-21 | 2020-03-18 | Celanese International Corporation | Acesulfame potassium compositions and processes for producing same |
Family Cites Families (9)
| 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 |
| 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 |
| DE2434549A1 (de) * | 1974-07-18 | 1976-01-29 | Hoechst Ag | Verfahren zur herstellung des suesstoffes 6-methyl-3,4-dihydro-1,2,3-oxathiazin4-on-2,2-dioxid |
| DE2447201A1 (de) * | 1974-10-03 | 1976-04-08 | Hoechst Ag | Verfahren zur herstellung von acetoacetamid-n-sulfofluorid |
| 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 |
| DE3527070A1 (de) * | 1985-07-29 | 1987-01-29 | Hoechst Ag | Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid |
| 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 |
| 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 |
-
1984
- 1984-08-07 DE DE19843429039 patent/DE3429039A1/de not_active Withdrawn
-
1985
- 1985-07-25 DE DE8585109376T patent/DE3564682D1/de not_active Expired
- 1985-07-25 EP EP85109376A patent/EP0173082B1/de not_active Expired
- 1985-07-25 AT AT85109376T patent/ATE36851T1/de not_active IP Right Cessation
- 1985-08-02 HU HU852963A patent/HU197889B/hu unknown
- 1985-08-05 ES ES545878A patent/ES8604186A1/es not_active Expired
- 1985-08-05 SU SU853933056A patent/SU1491338A3/ru active
- 1985-08-05 FI FI853008A patent/FI81790C/fi not_active IP Right Cessation
- 1985-08-05 US US06/762,563 patent/US4625024A/en not_active Expired - Lifetime
- 1985-08-05 AR AR301184A patent/AR240454A1/es active
- 1985-08-05 DD DD85279371A patent/DD246298A5/de not_active IP Right Cessation
- 1985-08-06 NO NO853103A patent/NO163772C/no unknown
- 1985-08-06 IL IL76027A patent/IL76027A/xx not_active IP Right Cessation
- 1985-08-06 AU AU45835/85A patent/AU575669B2/en not_active Expired
- 1985-08-06 JP JP60171936A patent/JPS6147473A/ja active Granted
- 1985-08-06 BR BR8503715A patent/BR8503715A/pt unknown
- 1985-08-06 CA CA000488177A patent/CA1241955A/en not_active Expired
- 1985-08-06 DK DK358285A patent/DK167976B1/da not_active IP Right Cessation
- 1985-08-06 KR KR1019850005654A patent/KR920008617B1/ko not_active Expired
- 1985-08-06 ZA ZA855921A patent/ZA855921B/xx unknown
- 1985-08-06 IE IE194085A patent/IE58482B1/en not_active IP Right Cessation
- 1985-08-07 MX MX206223A patent/MX160726A/es unknown
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