SU1342418A3 - Способ получени 6-метил-3,4-дигидро-1,2,3-оксатиазин-4-он-2,2-диоксида или его калиевой соли и способ получени аммоний ацетоацетамид-N-сульфонатов - Google Patents
Способ получени 6-метил-3,4-дигидро-1,2,3-оксатиазин-4-он-2,2-диоксида или его калиевой соли и способ получени аммоний ацетоацетамид-N-сульфонатов Download PDFInfo
- Publication number
- SU1342418A3 SU1342418A3 SU853867759A SU3867759A SU1342418A3 SU 1342418 A3 SU1342418 A3 SU 1342418A3 SU 853867759 A SU853867759 A SU 853867759A SU 3867759 A SU3867759 A SU 3867759A SU 1342418 A3 SU1342418 A3 SU 1342418A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mol
- lower alkyl
- acetoacetamide
- sulfonate
- acid
- Prior art date
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 8
- 238000000034 method Methods 0.000 title claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 title claims description 7
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 title 1
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- 150000001412 amines Chemical class 0.000 claims abstract 3
- 239000003054 catalyst Substances 0.000 claims abstract 3
- 239000003960 organic solvent Substances 0.000 claims abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 69
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 14
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000003863 ammonium salts Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001261 hydroxy acids Chemical class 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims 1
- 235000010269 sulphur dioxide Nutrition 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- XLXCHZCQTCBUOX-UHFFFAOYSA-N 1-prop-2-enylimidazole Chemical compound C=CCN1C=CN=C1 XLXCHZCQTCBUOX-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 1
- 235000003599 food sweetener Nutrition 0.000 abstract 1
- 239000003049 inorganic solvent Substances 0.000 abstract 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 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- 239000003765 sweetening agent Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000006188 syrup Substances 0.000 description 7
- 235000020357 syrup Nutrition 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- -1 dimethylethyl Chemical group 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
- RCBVKHVDFMLDNI-UHFFFAOYSA-N CC(CC(N)=O)=O.N Chemical compound CC(CC(N)=O)=O.N RCBVKHVDFMLDNI-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical group CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000001665 trituration Methods 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cephalosporin Compounds (AREA)
- Seasonings (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843410439 DE3410439A1 (de) | 1984-03-22 | 1984-03-22 | 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) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1342418A3 true SU1342418A3 (ru) | 1987-09-30 |
Family
ID=6231216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU853867759A SU1342418A3 (ru) | 1984-03-22 | 1985-03-21 | Способ получени 6-метил-3,4-дигидро-1,2,3-оксатиазин-4-он-2,2-диоксида или его калиевой соли и способ получени аммоний ацетоацетамид-N-сульфонатов |
Country Status (21)
| Country | Link |
|---|---|
| US (4) | US4607100A (https=) |
| EP (1) | EP0155634B1 (https=) |
| JP (2) | JPS60209578A (https=) |
| KR (1) | KR930000806B1 (https=) |
| AT (1) | ATE53579T1 (https=) |
| AU (2) | AU587970B2 (https=) |
| BR (1) | BR8501306A (https=) |
| CA (1) | CA1273923A (https=) |
| CS (3) | CS249540B2 (https=) |
| DD (3) | DD234007A5 (https=) |
| DE (2) | DE3410439A1 (https=) |
| DK (2) | DK170401B1 (https=) |
| ES (2) | ES8606315A1 (https=) |
| FI (1) | FI83076C (https=) |
| HU (2) | HU196976B (https=) |
| IE (1) | IE58342B1 (https=) |
| IL (1) | IL74676A (https=) |
| MX (1) | MX162880B (https=) |
| NO (3) | NO163771C (https=) |
| SU (1) | SU1342418A3 (https=) |
| ZA (1) | ZA852116B (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3410233A1 (de) * | 1984-03-21 | 1985-09-26 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung kristalliner salze des acetoacetamid-n-sulfofluorids |
| 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 |
| 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 |
| 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 (https=) * | 1992-03-17 | 1994-05-01 | Hoechst Ag | |
| DE10013259A1 (de) | 2000-03-17 | 2001-09-20 | Nutrinova Gmbh | Acesulfam-Metall-Komplexe Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10130298A1 (de) | 2001-06-22 | 2003-01-23 | Nutrinova Gmbh | Antimikrobiell wirksame Acesulfam-Komplexe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10130504B4 (de) | 2001-06-25 | 2005-02-03 | Nutrinova Nutrition Specialties & Food Ingredients Gmbh | Xanthin- und Phenazon-Acesulfam-H-Komplexe mit verbessertem Geschmack, Verfahren zu ihrer Herstellung und ihre Verwendung |
| JP2003026671A (ja) * | 2001-07-13 | 2003-01-29 | Daicel Chem Ind Ltd | オキサチアジン類の製造方法 |
| CN1336363A (zh) | 2001-07-25 | 2002-02-20 | 张元宾 | 乙酰磺胺酸钾的合成制备方法 |
| DE10253773B3 (de) * | 2002-11-19 | 2004-06-24 | Nutrinova Nutrition Specialties & Food Ingredients Gmbh | Verwendung von Acesulfamsäure zur pH-Wert-Absenkung |
| JP2006525791A (ja) | 2002-11-19 | 2006-11-16 | ニュートリノヴァ ニュートリション スペシャリティーズ アンド フード イングリーディエンツ ゲゼルシャフト ミット ベシュレンクテル ハフツング | 食品、化粧品製品、消費財（ｃｏｎｓｕｍｅｒｇｏｏｄｓ）および医薬品における微生物学的安定化のために甘味料酸（ｓｗｅｅｔｅｎｅｒａｃｉｄｓ）を使用する方法。 |
| US8043647B1 (en) | 2003-03-10 | 2011-10-25 | Perry Stephen C | Sugar replacement |
| DE10330025A1 (de) * | 2003-07-03 | 2005-01-20 | Nutrinova Nutrition Specialties & Food Ingredients Gmbh | Verfahren zur Herstellung eines Süßstoffsalzes basierend auf Aspartam und Acesulfam |
| 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 |
| US7599592B2 (en) | 2006-08-30 | 2009-10-06 | 3M Innovative Properties Company | Polymer fiber polarizers with aligned fibers |
| CN100410246C (zh) * | 2006-09-24 | 2008-08-13 | 张家港浩波化学品有限公司 | 一种合成乙酰磺胺酸钾过程中的水解工艺及该工艺的专用设备 |
| CN100516054C (zh) * | 2006-09-24 | 2009-07-22 | 张家港浩波化学品有限公司 | 一种合成乙酰磺胺酸钾过程中的磺化环合工艺及该工艺的专用设备 |
| NZ590372A (en) | 2008-07-08 | 2012-09-28 | Univ Texas | Novel inhibitors of proliferation and activation of signal transducer and activator of transcription (stats) |
| US20110257368A1 (en) | 2008-12-23 | 2011-10-20 | Schering Corporation | Purification of recombinantly produced interferon |
| EP2407146A1 (en) | 2010-07-15 | 2012-01-18 | Nutrinova Nutrition Specialties & Food Ingredients GmbH | Use of acesulfame K as a flavour modulator |
| US9024016B2 (en) * | 2012-06-08 | 2015-05-05 | Nutrinova Nutrition Specialists & Food Ingredients GmbH | Process for producing acesulfame potassium |
| CN103450114B (zh) * | 2013-08-19 | 2015-09-02 | 苏州浩波科技股份有限公司 | 5-氯-6-甲基-1,2,3-氧噁嗪-4(3h)-酮-2,2-二氧化物的合成方法 |
| CN104292181B (zh) * | 2014-09-27 | 2016-10-26 | 安徽金禾实业股份有限公司 | 一种mvr系统浓缩安赛蜜母液的方法 |
| 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 |
| LT3319948T (lt) * | 2016-09-21 | 2021-10-11 | Celanese International Corporation | Kalio acesulfamo kompozicijos ir jų gamybos būdai |
| HUE051396T2 (hu) * | 2016-09-21 | 2021-03-01 | Celanese Int Corp | Aceszulfám-kálium kompozíciók és az elõállításukra szolgáló eljárások |
| AU2021237818A1 (en) | 2020-03-19 | 2022-09-29 | Ferring Ventures Ltd. | Temperature-responsive virus storage system |
| TW202203962A (zh) | 2020-03-30 | 2022-02-01 | 英商崔澤爾有限公司 | 用於治療癌症之組合物及方法 |
| CN113454056B (zh) * | 2021-05-28 | 2022-11-04 | 安徽金禾实业股份有限公司 | 乙酰乙酰胺-n-磺酸三乙胺盐的制备方法 |
| CN113454075A (zh) * | 2021-05-28 | 2021-09-28 | 安徽金禾实业股份有限公司 | 乙酰磺胺酸钾的制备方法 |
| CN113454060B (zh) * | 2021-05-28 | 2022-11-25 | 安徽金禾实业股份有限公司 | 乙酰乙酰胺-n-磺酸三乙胺盐的制备方法 |
| JP7507993B1 (ja) * | 2024-03-11 | 2024-06-28 | 東京応化工業株式会社 | レジスト組成物、レジストパターン形成方法、化合物、及び酸発生剤 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL157304B (nl) * | 1970-01-10 | 1978-07-17 | Hoechst Ag | Werkwijze voor het bereiden van zoetmiddelen, onder toepassing van deze werkwijze verkregen gevormd voortbrengsel, alsmede werkwijze voor het bereiden van zoetsmakende verbindingen. |
| 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 |
| DE2228423C3 (de) * | 1972-06-10 | 1982-05-13 | Hoechst Ag, 6000 Frankfurt | 3,4-Dihydro-1,2,3-oxathiazin-4-one und Verfahren zu ihrer Herstellung |
| DE2434564A1 (de) * | 1974-07-18 | 1976-01-29 | Hoechst Ag | Verfahren zur herstellung von 6-methyl3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und seine verwendung als suesstoff |
| 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 |
| DE2453063A1 (de) * | 1974-11-08 | 1976-05-13 | 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 |
| 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 |
| 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 |
-
1984
- 1984-03-22 DE DE19843410439 patent/DE3410439A1/de not_active Withdrawn
-
1985
- 1985-03-13 DE DE8585102885T patent/DE3578174D1/de not_active Expired - Lifetime
- 1985-03-13 AT AT85102885T patent/ATE53579T1/de not_active IP Right Cessation
- 1985-03-13 EP EP85102885A patent/EP0155634B1/de not_active Expired - Lifetime
- 1985-03-15 HU HU85958A patent/HU196976B/hu unknown
- 1985-03-15 HU HU854514A patent/HU196954B/hu unknown
- 1985-03-20 FI FI851104A patent/FI83076C/fi not_active IP Right Cessation
- 1985-03-20 JP JP60054717A patent/JPS60209578A/ja active Granted
- 1985-03-20 CS CS851948A patent/CS249540B2/cs unknown
- 1985-03-20 CS CS859205A patent/CS249550B2/cs unknown
- 1985-03-20 US US06/714,177 patent/US4607100A/en not_active Expired - Lifetime
- 1985-03-20 ES ES541417A patent/ES8606315A1/es not_active Expired
- 1985-03-20 CS CS859204A patent/CS249549B2/cs unknown
- 1985-03-21 IE IE72385A patent/IE58342B1/en not_active IP Right Cessation
- 1985-03-21 DD DD85274325A patent/DD234007A5/de not_active IP Right Cessation
- 1985-03-21 DD DD85289447A patent/DD244554A5/de not_active IP Right Cessation
- 1985-03-21 NO NO851143A patent/NO163771C/no not_active IP Right Cessation
- 1985-03-21 DK DK129185A patent/DK170401B1/da not_active IP Right Cessation
- 1985-03-21 CA CA000477148A patent/CA1273923A/en not_active Expired - Lifetime
- 1985-03-21 ZA ZA852116A patent/ZA852116B/xx unknown
- 1985-03-21 DD DD85289450A patent/DD244551A5/de not_active IP Right Cessation
- 1985-03-21 SU SU853867759A patent/SU1342418A3/ru active
- 1985-03-21 AU AU40210/85A patent/AU587970B2/en not_active Expired
- 1985-03-21 KR KR1019850001853A patent/KR930000806B1/ko not_active Expired - Lifetime
- 1985-03-21 IL IL74676A patent/IL74676A/xx not_active IP Right Cessation
- 1985-03-22 MX MX204703A patent/MX162880B/es unknown
- 1985-03-22 BR BR8501306A patent/BR8501306A/pt not_active Application Discontinuation
- 1985-11-18 NO NO85854605A patent/NO163773C/no not_active IP Right Cessation
- 1985-11-18 NO NO85854604A patent/NO166364C/no not_active IP Right Cessation
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1986
- 1986-01-28 ES ES551338A patent/ES8701743A1/es not_active Expired
- 1986-06-03 US US06/870,078 patent/US4695629A/en not_active Expired - Lifetime
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1988
- 1988-09-16 AU AU22372/88A patent/AU598698B2/en not_active Expired
-
1990
- 1990-04-16 US US07/512,021 patent/US5011982A/en not_active Expired - Lifetime
- 1990-11-30 JP JP2336913A patent/JPH0647571B2/ja not_active Expired - Lifetime
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1991
- 1991-01-29 US US07/648,313 patent/US5103046A/en not_active Expired - Lifetime
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1994
- 1994-04-13 DK DK042394A patent/DK171986B1/da not_active IP Right Cessation
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| Title |
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| Выложенна за вка DE № 2453063, кл. С 07 С 143/86, опублик. 1976. * |
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