CA1050566A - Process for preparing acetoacetamide-n-sulfofluoride - Google Patents
Process for preparing acetoacetamide-n-sulfofluorideInfo
- Publication number
- CA1050566A CA1050566A CA236,881A CA236881A CA1050566A CA 1050566 A CA1050566 A CA 1050566A CA 236881 A CA236881 A CA 236881A CA 1050566 A CA1050566 A CA 1050566A
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- diketene
- sulfofluoride
- acetoacetamide
- asf
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000012442 inert solvent Substances 0.000 claims abstract description 11
- 239000003701 inert diluent Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 16
- 238000010992 reflux Methods 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000009835 boiling Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000036632 reaction speed Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- RQIMPDXRFCFBGC-UHFFFAOYSA-N n-(oxomethylidene)sulfamoyl fluoride Chemical compound FS(=O)(=O)N=C=O RQIMPDXRFCFBGC-UHFFFAOYSA-N 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- YGCFIWIQZPHFLU-UHFFFAOYSA-N acesulfame Chemical compound CC1=CC(=O)NS(=O)(=O)O1 YGCFIWIQZPHFLU-UHFFFAOYSA-N 0.000 description 1
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 229960001701 chloroform Drugs 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- -1 for example Chemical compound 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229940073584 methylene chloride Drugs 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742447201 DE2447201A1 (de) | 1974-10-03 | 1974-10-03 | Verfahren zur herstellung von acetoacetamid-n-sulfofluorid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050566A true CA1050566A (en) | 1979-03-13 |
Family
ID=5927429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA236,881A Expired CA1050566A (en) | 1974-10-03 | 1975-10-02 | Process for preparing acetoacetamide-n-sulfofluoride |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4052453A (OSRAM) |
| JP (1) | JPS5163125A (OSRAM) |
| AT (1) | AT340885B (OSRAM) |
| BE (1) | BE834176A (OSRAM) |
| CA (1) | CA1050566A (OSRAM) |
| CH (1) | CH598207A5 (OSRAM) |
| DE (1) | DE2447201A1 (OSRAM) |
| DK (1) | DK137640C (OSRAM) |
| FR (1) | FR2286816A1 (OSRAM) |
| GB (1) | GB1476101A (OSRAM) |
| IE (1) | IE41742B1 (OSRAM) |
| IT (1) | IT1043042B (OSRAM) |
| LU (1) | LU73492A1 (OSRAM) |
| NL (1) | NL7511450A (OSRAM) |
| ZA (1) | ZA756258B (OSRAM) |
Families Citing this family (2)
| 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 |
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2174239A (en) * | 1936-03-05 | 1939-09-26 | Standard Oil Dev Co | Preparing acetyl acetic acid derivatives |
| US3072724A (en) * | 1960-06-17 | 1963-01-08 | Eastman Kodak Co | Preparation of beta-ketoamide from 2, 2, 4, 4-tetraalkyl-1, 3-cyclobutanedione |
| US3387977A (en) * | 1964-03-31 | 1968-06-11 | Tecnifax Corp | Diazotype layer containing acetoacetamido coupling components |
| US3778474A (en) * | 1970-10-06 | 1973-12-11 | Lonza Ag | Production of acetoacetyl amides |
-
1974
- 1974-10-03 DE DE19742447201 patent/DE2447201A1/de not_active Withdrawn
-
1975
- 1975-09-29 NL NL7511450A patent/NL7511450A/xx not_active Application Discontinuation
- 1975-09-30 AT AT745075A patent/AT340885B/de not_active IP Right Cessation
- 1975-09-30 CH CH1267975A patent/CH598207A5/xx not_active IP Right Cessation
- 1975-10-01 IT IT27858/75A patent/IT1043042B/it active
- 1975-10-01 LU LU73492A patent/LU73492A1/xx unknown
- 1975-10-01 US US05/618,405 patent/US4052453A/en not_active Expired - Lifetime
- 1975-10-01 JP JP50117774A patent/JPS5163125A/ja active Pending
- 1975-10-02 FR FR7530160A patent/FR2286816A1/fr active Granted
- 1975-10-02 CA CA236,881A patent/CA1050566A/en not_active Expired
- 1975-10-02 ZA ZA00756258A patent/ZA756258B/xx unknown
- 1975-10-02 IE IE2153/75A patent/IE41742B1/en unknown
- 1975-10-02 GB GB4031475A patent/GB1476101A/en not_active Expired
- 1975-10-02 DK DK445575A patent/DK137640C/da active
- 1975-10-03 BE BE160673A patent/BE834176A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU8540175A (en) | 1977-04-07 |
| ATA745075A (de) | 1977-05-15 |
| JPS5163125A (en) | 1976-06-01 |
| US4052453A (en) | 1977-10-04 |
| AT340885B (de) | 1978-01-10 |
| CH598207A5 (OSRAM) | 1978-04-28 |
| DK137640C (da) | 1978-10-09 |
| FR2286816A1 (fr) | 1976-04-30 |
| BE834176A (fr) | 1976-04-05 |
| ZA756258B (en) | 1976-09-29 |
| IE41742L (en) | 1976-04-03 |
| IE41742B1 (en) | 1980-03-12 |
| IT1043042B (it) | 1980-02-20 |
| FR2286816B1 (OSRAM) | 1979-10-12 |
| GB1476101A (en) | 1977-06-10 |
| DK445575A (da) | 1976-04-04 |
| NL7511450A (nl) | 1976-04-06 |
| LU73492A1 (OSRAM) | 1977-05-24 |
| DE2447201A1 (de) | 1976-04-08 |
| DK137640B (da) | 1978-04-10 |
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