DE2264235C3 - Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-l,23-oxa thiazin-4-on-2,2-dioxid - Google Patents
Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-l,23-oxa thiazin-4-on-2,2-dioxidInfo
- Publication number
- DE2264235C3 DE2264235C3 DE2264235A DE2264235A DE2264235C3 DE 2264235 C3 DE2264235 C3 DE 2264235C3 DE 2264235 A DE2264235 A DE 2264235A DE 2264235 A DE2264235 A DE 2264235A DE 2264235 C3 DE2264235 C3 DE 2264235C3
- Authority
- DE
- Germany
- Prior art keywords
- dioxide
- reaction
- dihydro
- tert
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 claims description 8
- 238000003776 cleavage reaction Methods 0.000 claims description 8
- 230000007017 scission Effects 0.000 claims description 8
- 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 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 6
- RQIMPDXRFCFBGC-UHFFFAOYSA-N n-(oxomethylidene)sulfamoyl fluoride Chemical compound FS(=O)(=O)N=C=O RQIMPDXRFCFBGC-UHFFFAOYSA-N 0.000 claims description 5
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 4
- -1 halogen sulfonyl isocyanates Chemical class 0.000 claims description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
- BVRSFVRSIRIGNR-UHFFFAOYSA-N 3,4-dihydrooxathiazine 2-oxide Chemical compound O=S1NCC=CO1 BVRSFVRSIRIGNR-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 235000003599 food sweetener Nutrition 0.000 claims description 2
- 239000003765 sweetening agent Substances 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XMPNAVKOVWQFKJ-UHFFFAOYSA-N CC1=CCNS(O1)=O Chemical compound CC1=CCNS(O1)=O XMPNAVKOVWQFKJ-UHFFFAOYSA-N 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XLXCHZCQTCBUOX-UHFFFAOYSA-N 1-prop-2-enylimidazole Chemical compound C=CCN1C=CN=C1 XLXCHZCQTCBUOX-UHFFFAOYSA-N 0.000 description 1
- PLSMHHUFDLYURK-UHFFFAOYSA-N 2,3,4-trimethyl-3-pentanol Chemical compound CC(C)C(C)(O)C(C)C PLSMHHUFDLYURK-UHFFFAOYSA-N 0.000 description 1
- IKECULIHBUCAKR-UHFFFAOYSA-N 2,3-dimethylbutan-2-ol Chemical compound CC(C)C(C)(C)O IKECULIHBUCAKR-UHFFFAOYSA-N 0.000 description 1
- HRHFUHGNTSSIFS-UHFFFAOYSA-N 2h-thiazine 1-oxide Chemical class O=S1NC=CC=C1 HRHFUHGNTSSIFS-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical class CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 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
- 239000006227 byproduct Substances 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 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
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000010626 work up procedure 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2264235A DE2264235C3 (de) | 1972-12-30 | 1972-12-30 | Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-l,23-oxa thiazin-4-on-2,2-dioxid |
| ZA739560A ZA739560B (en) | 1972-12-30 | 1973-12-19 | Process for the manufacture of 6-methyl-3,4-dihydro-1,2,3-oxathiazine-4-one-2,2-dioxidea |
| CH1810873A CH593958A5 (OSRAM) | 1972-12-30 | 1973-12-21 | |
| GB5964273A GB1452099A (en) | 1972-12-30 | 1973-12-21 | Process for the manufacture of 6-methyl-3,4-dihydro-1,2,3- oxathiazin-4-one-2,2-dioxide |
| NL737317601A NL153870B (nl) | 1972-12-30 | 1973-12-21 | Werkwijze voor het bereiden van 6-methyl-3,4 dihydro-1,2,3-oxathiazin-4-on-2,2-dioxyde. |
| JP14458673A JPS572711B2 (OSRAM) | 1972-12-30 | 1973-12-27 | |
| IT32320/73A IT1006681B (it) | 1972-12-30 | 1973-12-27 | Processo per la produzione di 6 metil 3 4 diidro 1 2 3 ossatiazin 4 on 2 2 diossido |
| CA189,108A CA1006517A (en) | 1972-12-30 | 1973-12-28 | Process for the manufacture of 6-methyl-3,4-dihydro-1,2,3-oxathiazine-4-one-2,2-dioxide |
| FR7346798A FR2212337B1 (OSRAM) | 1972-12-30 | 1973-12-28 | |
| AT1085873A AT341536B (de) | 1972-12-30 | 1973-12-28 | Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid |
| US429628A US3917589A (en) | 1972-12-30 | 1973-12-28 | Process for the manufacture of 6-methyl-3,4-dihydro-1,2,3-oxathiazine-4-one-2,2-dioxide |
| AU64031/73A AU465124B2 (en) | 1972-12-30 | 1973-12-28 | Process forthe manufacture of 6-methyl-3, 4 dihydro-1, 2, 3-oxathiazine-4-one-2, 2-dioxide |
| BE139480A BE809349A (fr) | 1972-12-30 | 1974-01-02 | Procede de preparation d'une oxathiazinone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2264235A DE2264235C3 (de) | 1972-12-30 | 1972-12-30 | Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-l,23-oxa thiazin-4-on-2,2-dioxid |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2264235A1 DE2264235A1 (de) | 1974-07-11 |
| DE2264235B2 DE2264235B2 (de) | 1980-01-17 |
| DE2264235C3 true DE2264235C3 (de) | 1980-09-11 |
Family
ID=5865822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2264235A Expired DE2264235C3 (de) | 1972-12-30 | 1972-12-30 | Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-l,23-oxa thiazin-4-on-2,2-dioxid |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3917589A (OSRAM) |
| JP (1) | JPS572711B2 (OSRAM) |
| AT (1) | AT341536B (OSRAM) |
| AU (1) | AU465124B2 (OSRAM) |
| BE (1) | BE809349A (OSRAM) |
| CA (1) | CA1006517A (OSRAM) |
| CH (1) | CH593958A5 (OSRAM) |
| DE (1) | DE2264235C3 (OSRAM) |
| FR (1) | FR2212337B1 (OSRAM) |
| GB (1) | GB1452099A (OSRAM) |
| IT (1) | IT1006681B (OSRAM) |
| NL (1) | NL153870B (OSRAM) |
| ZA (1) | ZA739560B (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| 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 |
| SMT202000051T1 (it) | 2016-09-21 | 2020-03-13 | Celanese Int Corp | Composizione di acesulfame potassio e procedimenti per la produzione delle stesse |
| DK3319949T3 (da) | 2016-09-21 | 2020-09-28 | Celanese Int Corp | Acesulfam-kalium-sammensætninger og fremgangsmåder til fremstilling af disse |
| WO2018057387A1 (en) | 2016-09-21 | 2018-03-29 | Celanese International Corporation | Acesulfame potassium compositions and processes for producing same |
| ES2824812T5 (en) | 2016-09-21 | 2025-04-08 | Celanese Int Corp | Acesulfame potassium compositions and processes for producing same |
Family Cites Families (1)
| 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 |
-
1972
- 1972-12-30 DE DE2264235A patent/DE2264235C3/de not_active Expired
-
1973
- 1973-12-19 ZA ZA739560A patent/ZA739560B/xx unknown
- 1973-12-21 GB GB5964273A patent/GB1452099A/en not_active Expired
- 1973-12-21 NL NL737317601A patent/NL153870B/xx not_active IP Right Cessation
- 1973-12-21 CH CH1810873A patent/CH593958A5/xx not_active IP Right Cessation
- 1973-12-27 IT IT32320/73A patent/IT1006681B/it active
- 1973-12-27 JP JP14458673A patent/JPS572711B2/ja not_active Expired
- 1973-12-28 US US429628A patent/US3917589A/en not_active Expired - Lifetime
- 1973-12-28 AT AT1085873A patent/AT341536B/de not_active IP Right Cessation
- 1973-12-28 FR FR7346798A patent/FR2212337B1/fr not_active Expired
- 1973-12-28 AU AU64031/73A patent/AU465124B2/en not_active Expired
- 1973-12-28 CA CA189,108A patent/CA1006517A/en not_active Expired
-
1974
- 1974-01-02 BE BE139480A patent/BE809349A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2264235A1 (de) | 1974-07-11 |
| FR2212337B1 (OSRAM) | 1977-06-10 |
| US3917589A (en) | 1975-11-04 |
| AU6403173A (en) | 1975-07-03 |
| CA1006517A (en) | 1977-03-08 |
| CH593958A5 (OSRAM) | 1977-12-30 |
| IT1006681B (it) | 1976-10-20 |
| NL7317601A (OSRAM) | 1974-07-02 |
| AT341536B (de) | 1978-02-10 |
| NL153870B (nl) | 1977-07-15 |
| JPS572711B2 (OSRAM) | 1982-01-18 |
| ATA1085873A (de) | 1977-06-15 |
| AU465124B2 (en) | 1975-09-18 |
| BE809349A (fr) | 1974-07-02 |
| ZA739560B (en) | 1974-11-27 |
| DE2264235B2 (de) | 1980-01-17 |
| JPS4994690A (OSRAM) | 1974-09-09 |
| GB1452099A (en) | 1976-10-06 |
| FR2212337A1 (OSRAM) | 1974-07-26 |
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