DE2049045B2 - Verfahren zur Herstellung von Monochloracetoacetamiden - Google Patents
Verfahren zur Herstellung von MonochloracetoacetamidenInfo
- Publication number
- DE2049045B2 DE2049045B2 DE19702049045 DE2049045A DE2049045B2 DE 2049045 B2 DE2049045 B2 DE 2049045B2 DE 19702049045 DE19702049045 DE 19702049045 DE 2049045 A DE2049045 A DE 2049045A DE 2049045 B2 DE2049045 B2 DE 2049045B2
- Authority
- DE
- Germany
- Prior art keywords
- mmaa
- chlorination
- water
- selectivity
- chlorine
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 27
- 230000008569 process Effects 0.000 title claims description 15
- VCPNLOMAQUZMBY-UHFFFAOYSA-N 4-chloro-3-oxobutanamide Chemical class NC(=O)CC(=O)CCl VCPNLOMAQUZMBY-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- ITFHDLJYTOXTOZ-UHFFFAOYSA-N 2,2-dichloro-3-oxobutanamide Chemical class CC(=O)C(Cl)(Cl)C(N)=O ITFHDLJYTOXTOZ-UHFFFAOYSA-N 0.000 claims description 4
- AOOLFYMBFIGYDE-UHFFFAOYSA-N 2-chloro-3-oxobutanamide Chemical class CC(=O)C(Cl)C(N)=O AOOLFYMBFIGYDE-UHFFFAOYSA-N 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000000460 chlorine Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 238000005660 chlorination reaction Methods 0.000 description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 18
- 229910052801 chlorine Inorganic materials 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical compound CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000003963 dichloro group Chemical group Cl* 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- ATWLCPHWYPSRBQ-UHFFFAOYSA-N N-Methylacetoacetamide Chemical compound CNC(=O)CC(C)=O ATWLCPHWYPSRBQ-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XIWMZCRVSYHMER-UHFFFAOYSA-N 2-chloro-n-methyl-3-oxobutanamide Chemical compound CNC(=O)C(Cl)C(C)=O XIWMZCRVSYHMER-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NVPCGXUWUBHZBD-IHWYPQMZSA-N (z)-3-hydroxybut-2-enoic acid Chemical compound C\C(O)=C\C(O)=O NVPCGXUWUBHZBD-IHWYPQMZSA-N 0.000 description 1
- BLQDAFLFPNDCMJ-UHFFFAOYSA-N 2,2-dichloro-n-methylacetamide Chemical compound CNC(=O)C(Cl)Cl BLQDAFLFPNDCMJ-UHFFFAOYSA-N 0.000 description 1
- FGCTYLRDRKTVRR-UHFFFAOYSA-N 4,4-dichloro-3-oxobutanamide Chemical compound NC(=O)CC(=O)C(Cl)Cl FGCTYLRDRKTVRR-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241000238633 Odonata Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WYWQQSUGCKUJJJ-UHFFFAOYSA-N n-ethyl-n-methyl-3-oxobutanamide Chemical compound CCN(C)C(=O)CC(C)=O WYWQQSUGCKUJJJ-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
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 |
|---|---|---|---|
| US86490169A | 1969-10-08 | 1969-10-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2049045A1 DE2049045A1 (https=) | 1971-04-22 |
| DE2049045B2 true DE2049045B2 (de) | 1979-03-01 |
Family
ID=25344316
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702049045 Ceased DE2049045B2 (de) | 1969-10-08 | 1970-10-06 | Verfahren zur Herstellung von Monochloracetoacetamiden |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH535205A (https=) |
| DE (1) | DE2049045B2 (https=) |
| FR (1) | FR2065067A5 (https=) |
| GB (1) | GB1319650A (https=) |
| NL (1) | NL169734C (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4235818A (en) * | 1977-06-30 | 1980-11-25 | Ciba-Geigy Corporation | Process for producing alpha-monochloroacetoacetic acid monomethylamide |
| DE2824046A1 (de) * | 1978-06-01 | 1979-12-06 | Wacker Chemie Gmbh | Verfahren zur herstellung von alpha- chloracetoacetamiden |
-
1970
- 1970-10-06 CH CH1477870A patent/CH535205A/de not_active IP Right Cessation
- 1970-10-06 FR FR7036030A patent/FR2065067A5/fr not_active Expired
- 1970-10-06 DE DE19702049045 patent/DE2049045B2/de not_active Ceased
- 1970-10-06 NL NL7014636A patent/NL169734C/xx not_active IP Right Cessation
- 1970-10-06 GB GB4747170A patent/GB1319650A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2049045A1 (https=) | 1971-04-22 |
| CH535205A (de) | 1973-03-31 |
| NL7014636A (https=) | 1971-04-14 |
| GB1319650A (en) | 1973-06-06 |
| NL169734B (nl) | 1982-03-16 |
| NL169734C (nl) | 1982-08-16 |
| FR2065067A5 (https=) | 1971-07-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8235 | Patent refused |