DD244551A5 - Verfahren zur herstellung von acetoacetamid-n-sulfonsaeure - Google Patents

Verfahren zur herstellung von acetoacetamid-n-sulfonsaeure Download PDF

Info

Publication number: DD244551A5
Authority: DD; German Democratic Republic
Prior art keywords: acid; acetoacetamide; items; atoms; aliphatic
Prior art date: 1984-03-22

Application number

DD85289450A

Other languages

German (de)

English (en)

Inventor

Karl Claus

Adolf Linkies

Dieter Reuschling

Original Assignee

��@��k��

Priority date (The priority date 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 date listed.)

1984-03-22

Filing date

1985-03-21

Publication date

1987-04-08

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6231216&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DD244551(A5) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1985-03-21 Application filed by ��@��k�� filed Critical ��@��k��

1987-04-08 Publication of DD244551A5 publication Critical patent/DD244551A5/de

Links

QXBGLCSYJYZBFK-UHFFFAOYSA-N 3-oxobutanoylsulfamic acid Chemical compound CC(=O)CC(=O)NS(O)(=O)=O QXBGLCSYJYZBFK-UHFFFAOYSA-N 0.000 title claims description 9
238000004519 manufacturing process Methods 0.000 title description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
238000000034 method Methods 0.000 claims description 26
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 16
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 15
230000008569 process Effects 0.000 claims description 15
-1 aliphatic ketones Chemical class 0.000 claims description 13
239000003054 catalyst 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 11
150000001412 amines Chemical class 0.000 claims description 11
239000003960 organic solvent Substances 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 9
229960000583 acetic acid Drugs 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
239000012362 glacial acetic acid Substances 0.000 claims description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 5
150000003512 tertiary amines Chemical class 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
229910052744 lithium Inorganic materials 0.000 claims description 2
230000000269 nucleophilic effect Effects 0.000 claims description 2
125000004437 phosphorous atom Chemical group 0.000 claims description 2
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
150000003865 secondary ammonium salts Chemical class 0.000 claims description 2
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
150000003866 tertiary ammonium salts Chemical class 0.000 claims description 2
150000004292 cyclic ethers Chemical class 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000007795 chemical reaction product Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
239000000460 chlorine Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 7
239000006188 syrup Substances 0.000 description 7
235000020357 syrup Nutrition 0.000 description 7
RQIMPDXRFCFBGC-UHFFFAOYSA-N n-(oxomethylidene)sulfamoyl fluoride Chemical compound FS(=O)(=O)N=C=O RQIMPDXRFCFBGC-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000002585 base Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
238000001816 cooling Methods 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
XLXCHZCQTCBUOX-UHFFFAOYSA-N 1-prop-2-enylimidazole Chemical compound C=CCN1C=CN=C1 XLXCHZCQTCBUOX-UHFFFAOYSA-N 0.000 description 4
GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
150000003003 phosphines Chemical class 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-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
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-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
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
XIMSTDAFGWROBF-UHFFFAOYSA-N oxathiazine 2-oxide Chemical compound O=S1OC=CC=N1 XIMSTDAFGWROBF-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
LFMIQNJMJJKICW-UHFFFAOYSA-N 1,1,2-trichloro-2-fluoroethene Chemical group FC(Cl)=C(Cl)Cl LFMIQNJMJJKICW-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
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JUXXCHAGQCBNTI-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetramethylpropane-1,2-diamine Chemical compound CN(C)C(C)CN(C)C JUXXCHAGQCBNTI-UHFFFAOYSA-N 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
FTKZKUSQFCXEEL-UHFFFAOYSA-N 2-ethyl-3-methylpyridine Chemical class CCC1=NC=CC=C1C FTKZKUSQFCXEEL-UHFFFAOYSA-N 0.000 description 1
IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-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
QRQKCMFVJWNKQI-UHFFFAOYSA-N 4-(2-morpholin-4-ylethyl)morpholine Chemical compound C1COCCN1CCN1CCOCC1 QRQKCMFVJWNKQI-UHFFFAOYSA-N 0.000 description 1
GAVPOWTXUZVFML-UHFFFAOYSA-M 4-nitrobenzenediazonium;chloride Chemical compound [Cl-].[O-][N+](=O)C1=CC=C([N+]#N)C=C1 GAVPOWTXUZVFML-UHFFFAOYSA-M 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
GEHMBYLTCISYNY-UHFFFAOYSA-N Ammonium sulfamate Chemical compound [NH4+].NS([O-])(=O)=O GEHMBYLTCISYNY-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-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
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-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
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-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
230000009471 action Effects 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000007805 chemical reaction reactant Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000010411 cooking Methods 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
239000013078 crystal Substances 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
229940043279 diisopropylamine Drugs 0.000 description 1
239000012971 dimethylpiperazine Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
238000003541 multi-stage reaction Methods 0.000 description 1
LIGIARLVFBHRJF-UHFFFAOYSA-N n'-[2-(diethylamino)ethyl]-n,n,n'-triethylethane-1,2-diamine Chemical compound CCN(CC)CCN(CC)CCN(CC)CC LIGIARLVFBHRJF-UHFFFAOYSA-N 0.000 description 1
VEAZEPMQWHPHAG-UHFFFAOYSA-N n,n,n',n'-tetramethylbutane-1,4-diamine Chemical compound CN(C)CCCCN(C)C VEAZEPMQWHPHAG-UHFFFAOYSA-N 0.000 description 1
FRQONEWDWWHIPM-UHFFFAOYSA-N n,n-dicyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)C1CCCCC1 FRQONEWDWWHIPM-UHFFFAOYSA-N 0.000 description 1
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 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
XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
150000003864 primary ammonium salts Chemical class 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
QARNHIBOPBXNSX-UHFFFAOYSA-N prop-1-enoxymethylbenzene Chemical compound CC=COCC1=CC=CC=C1 QARNHIBOPBXNSX-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent 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
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
DQMFXGQHSPWNOA-UHFFFAOYSA-N triethylazanium;sulfamate Chemical compound NS([O-])(=O)=O.CC[NH+](CC)CC DQMFXGQHSPWNOA-UHFFFAOYSA-N 0.000 description 1
RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 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)
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)
Catalysts (AREA)
Seasonings (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD85289450A 1984-03-22 1985-03-21 Verfahren zur herstellung von acetoacetamid-n-sulfonsaeure DD244551A5 (de)

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
DD244551A5 true DD244551A5 (de)	1987-04-08

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ID=6231216

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
DD85274325A DD234007A5 (de)	1984-03-22	1985-03-21	Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-diaxid und deren nicht toxischen salzen
DD85289450A DD244551A5 (de)	1984-03-22	1985-03-21	Verfahren zur herstellung von acetoacetamid-n-sulfonsaeure
DD85289447A DD244554A5 (de)	1984-03-22	1985-03-21	Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nicht-toxischen salzen

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Application Number	Title	Priority Date	Filing Date
DD85274325A DD234007A5 (de)	1984-03-22	1985-03-21	Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-diaxid und deren nicht toxischen salzen

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Application Number	Title	Priority Date	Filing Date
DD85289447A DD244554A5 (de)	1984-03-22	1985-03-21	Verfahren zur herstellung von 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nicht-toxischen salzen

Country Status (21)

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US (4)	US4607100A (ja)
EP (1)	EP0155634B1 (ja)
JP (2)	JPS60209578A (ja)
KR (1)	KR930000806B1 (ja)
AT (1)	ATE53579T1 (ja)
AU (2)	AU587970B2 (ja)
BR (1)	BR8501306A (ja)
CA (1)	CA1273923A (ja)
CS (3)	CS249540B2 (ja)
DD (3)	DD234007A5 (ja)
DE (2)	DE3410439A1 (ja)
DK (2)	DK170401B1 (ja)
ES (2)	ES8606315A1 (ja)
FI (1)	FI83076C (ja)
HU (2)	HU196976B (ja)
IE (1)	IE58342B1 (ja)
IL (1)	IL74676A (ja)
MX (1)	MX162880B (ja)
NO (3)	NO163771C (ja)
SU (1)	SU1342418A3 (ja)
ZA (1)	ZA852116B (ja)

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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
AU2009268841B2 (en)	2008-07-08	2014-02-06	Board Of Regents, The University Of Texas System	Novel inhibitors of proliferation and activation of signal transducer and activator of transcription (STATS)
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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
EP3753930A1 (en)	2016-09-21	2020-12-23	Celanese International Corporation	Acesulfame potassium compositions and processes for producing same
EP3744716A1 (en)	2016-09-21	2020-12-02	Celanese International Corporation	Acesulfame potassium compositions and processes for producing same
SMT202100565T1 (it)	2016-09-21	2021-11-12	Celanese Int Corp	Composizioni di acesulfame potassico e processi per la loro preparazione
HRP20192165T4 (hr) *	2016-09-21	2025-07-18	Celanese International Corporation	Acesulfam-kalij-pripravci i postupci njihove proizvodnje
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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
WO2022246871A1 (zh) *	2021-05-28	2022-12-01	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
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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 CS CS851948A patent/CS249540B2/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 CS859205A patent/CS249550B2/cs unknown
- 1985-03-20 JP JP60054717A patent/JPS60209578A/ja active Granted
- 1985-03-20 FI FI851104A patent/FI83076C/fi not_active IP Right Cessation
- 1985-03-20 CS CS859204A patent/CS249549B2/cs unknown
- 1985-03-21 CA CA000477148A patent/CA1273923A/en not_active Expired - Lifetime
- 1985-03-21 SU SU853867759A patent/SU1342418A3/ru active
- 1985-03-21 DD DD85274325A patent/DD234007A5/de not_active IP Right Cessation
- 1985-03-21 AU AU40210/85A patent/AU587970B2/en not_active Expired
- 1985-03-21 DD DD85289450A patent/DD244551A5/de not_active IP Right Cessation
- 1985-03-21 DK DK129185A patent/DK170401B1/da not_active IP Right Cessation
- 1985-03-21 ZA ZA852116A patent/ZA852116B/xx unknown
- 1985-03-21 NO NO851143A patent/NO163771C/no not_active IP Right Cessation
- 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
- 1985-03-21 IE IE72385A patent/IE58342B1/en not_active IP Right Cessation
- 1985-03-21 DD DD85289447A patent/DD244554A5/de 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
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
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
1991
- 1991-01-29 US US07/648,313 patent/US5103046A/en not_active Expired - Lifetime
1994
- 1994-04-13 DK DK042394A patent/DK171986B1/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU2237288A (en)	1988-12-22
NO163771C (no)	1990-07-18
DK171986B1 (da)	1997-09-08
US4695629A (en)	1987-09-22
AU598698B2 (en)	1990-06-28
IE850723L (en)	1985-09-22
MX162880B (es)	1991-07-02
HU196954B (en)	1989-02-28
FI851104A0 (fi)	1985-03-20
US5011982A (en)	1991-04-30
NO854604L (no)	1985-09-23
IL74676A (en)	1988-12-30
NO163773B (no)	1990-04-09
DE3410439A1 (de)	1985-09-26
ZA852116B (en)	1985-11-27
CA1273923A (en)	1990-09-11
US5103046A (en)	1992-04-07
AU587970B2 (en)	1989-09-07
NO163773C (no)	1990-07-18
DD244554A5 (de)	1987-04-08
EP0155634A3 (en)	1987-03-04
DK42394A (da)	1994-04-13
SU1342418A3 (ru)	1987-09-30
NO166364B (no)	1991-04-02
JPS60209578A (ja)	1985-10-22
NO854605L (no)	1985-09-23
JPH03184948A (ja)	1991-08-12
AU4021085A (en)	1985-09-26
DD234007A5 (de)	1986-03-19
BR8501306A (pt)	1985-11-19
ES8701743A1 (es)	1986-12-16
DK129185D0 (da)	1985-03-21
ES551338A0 (es)	1986-12-16
HU196976B (en)	1989-02-28
US4607100A (en)	1986-08-19
NO163771B (no)	1990-04-09
DK170401B1 (da)	1995-08-21
FI851104L (fi)	1985-09-23
JPH0570627B2 (ja)	1993-10-05
KR930000806B1 (ko)	1993-02-05
ES8606315A1 (es)	1986-04-16
EP0155634A2 (de)	1985-09-25
IE58342B1 (en)	1993-09-08
KR850006192A (ko)	1985-10-02
FI83076C (fi)	1991-05-27
ES541417A0 (es)	1986-04-16
IL74676A0 (en)	1985-06-30
NO166364C (no)	1991-07-10
ATE53579T1 (de)	1990-06-15
CS249550B2 (en)	1987-03-12
NO851143L (no)	1985-09-23
DE3578174D1 (de)	1990-07-19
FI83076B (fi)	1991-02-15
HUT36467A (en)	1985-09-30
EP0155634B1 (de)	1990-06-13
CS249540B2 (en)	1987-03-12
JPH0647571B2 (ja)	1994-06-22
DK129185A (da)	1985-09-23
CS249549B2 (en)	1987-03-12

Legal Events

Date	Code	Title	Description
1995-08-03	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD244551A5 (de)	1987-04-08	Verfahren zur herstellung von acetoacetamid-n-sulfonsaeure
EP0215347B1 (de)	1990-01-24	Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxid sowie zu dessen Reinigung
EP0217024B1 (de)	1990-04-25	Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid
DE1795763A1 (de)	1974-11-21	Verfahren zur herstellung von desacylierten vielkernigen indolverbindungen sowie deren estern
EP0218076B1 (de)	1990-01-03	Verfahren zur Herstellung der nicht-toxischen Salze des 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxids
DE2416449A1 (de)	1974-10-24	Penicilline, ihre salze, verfahren zu ihrer herstellung und arzneimittel
EP0159516B1 (de)	1988-01-20	Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nicht-toxischen Salzen
DE2434549A1 (de)	1976-01-29	Verfahren zur herstellung des suesstoffes 6-methyl-3,4-dihydro-1,2,3-oxathiazin4-on-2,2-dioxid
DE2156761C3 (de)	1975-01-02	Verfahren zur Herstellung von Isocyanaten
EP0173082B1 (de)	1988-08-31	Verfahren zur Herstellung von 6-Methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxid und dessen nicht-toxischen Salzen
DE3531357A1 (de)	1987-03-12	Verfahren zur herstellung der nicht-toxischen salze des 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-on-2,2-dioxids
DE2357097A1 (de)	1974-05-22	Cephalosporine und verfahren zu deren herstellung
DE887816C (de)	1953-08-27	Verfahren zur Herstellung von 1-Nitrophenyl-2-amino-propan-1, 3-diolderivaten
DE3021566C2 (ja)	1990-05-03
DE1795413B2 (de)	1977-08-11	Verfahren zur herstellung von penicillin- oder penicellinsulfoxidestern
DE4331223A1 (de)	1994-06-30	Verfahren zur Herstellung von 2-Ethoxy-4,6-dihydroxypyrimidin oder dessen Alkalisalz
CH649993A5 (de)	1985-06-28	Verfahren zur herstellung von uracilen.
DE2235377A1 (de)	1973-02-08	2,4-thiazol-dimethanol-carbamat und verfahren zu dessen herstellung
DE896984C (de)	1953-11-16	Verfahren zur Herstellung von reinen Alkalisalzen, insbesondere Natriumsalzen, von Penicillin
DE3431009A1 (de)	1985-03-21	Verfahren zur herstellung von 6-demethyl-6-desoxy-6-methylen-5-oxytetracyclin und dessen 11a-chlorderivat
DE2447201A1 (de)	1976-04-08	Verfahren zur herstellung von acetoacetamid-n-sulfofluorid
DE3705084A1 (de)	1988-09-01	Verfahren zur herstellung von pyrimidinen
DE2434547A1 (de)	1976-01-29	Beta-acyloxy-crotonsaeureamid-nsulfohalogenide, verfahren zu ihrer herstellung und ihre ueberfuehrung in suesstoffe
DD283992A5 (de)	1990-10-31	Verfahren zur herstellung von n-sulfomethyl-glycinat-verbindungen
DE1670091B2 (de)	1975-06-26	Derivate der 6-Aminopenicillansäure und Verfahren zu ihrer Herstellung