DE2647499C2 - Verfahren zur kontinuierlichen Herstellung von Acetoacetamiden - Google Patents
Verfahren zur kontinuierlichen Herstellung von AcetoacetamidenInfo
- Publication number
- DE2647499C2 DE2647499C2 DE2647499A DE2647499A DE2647499C2 DE 2647499 C2 DE2647499 C2 DE 2647499C2 DE 2647499 A DE2647499 A DE 2647499A DE 2647499 A DE2647499 A DE 2647499A DE 2647499 C2 DE2647499 C2 DE 2647499C2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- diketene
- acetoacetamides
- parts
- amines
- 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 20
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 title claims description 6
- 238000010924 continuous production Methods 0.000 title claims description 4
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000007795 chemical reaction product Substances 0.000 description 12
- -1 aliphatic amines Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 150000003141 primary amines Chemical class 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- ATWLCPHWYPSRBQ-UHFFFAOYSA-N N-Methylacetoacetamide Chemical compound CNC(=O)CC(C)=O ATWLCPHWYPSRBQ-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000003139 primary aliphatic amines Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- JWDSCUIQYJUHHM-UHFFFAOYSA-N 2-ethylacetoacetic acid Chemical compound CCC(C(C)=O)C(O)=O JWDSCUIQYJUHHM-UHFFFAOYSA-N 0.000 description 1
- ISYYTKAMGZWYBB-UHFFFAOYSA-N 2-ethylhexan-1-amine;hexan-1-amine Chemical compound CCCCCCN.CCCCC(CC)CN ISYYTKAMGZWYBB-UHFFFAOYSA-N 0.000 description 1
- ZXLSKTZECNUVIS-UHFFFAOYSA-N 4-methyl-3-oxopentanoic acid Chemical compound CC(C)C(=O)CC(O)=O ZXLSKTZECNUVIS-UHFFFAOYSA-N 0.000 description 1
- FBOWZEGPOWZYAW-UHFFFAOYSA-N 5-methyl-3-oxo-4-propan-2-ylhexanoic acid Chemical compound CC(C)C(C(C)C)C(=O)CC(=O)O FBOWZEGPOWZYAW-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- PPQMTYWIYORUKZ-UHFFFAOYSA-N N-ethylethanamine 3-oxobutanoic acid Chemical compound CCNCC.CC(=O)CC(O)=O PPQMTYWIYORUKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 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
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HBRNMIYLJIXXEE-UHFFFAOYSA-N dodecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN HBRNMIYLJIXXEE-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- QKYWADPCTHTJHQ-UHFFFAOYSA-N n,2-dimethylpropan-1-amine Chemical compound CNCC(C)C QKYWADPCTHTJHQ-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2647499A DE2647499C2 (de) | 1976-10-21 | 1976-10-21 | Verfahren zur kontinuierlichen Herstellung von Acetoacetamiden |
| NL7710442A NL7710442A (nl) | 1976-10-21 | 1977-09-23 | Werkwijze voor de continue bereiding van acetoaceetamiden. |
| IL53008A IL53008A (en) | 1976-10-21 | 1977-09-28 | Process for the continuous manufacture of acetoacetamides |
| US05/840,709 US4129596A (en) | 1976-10-21 | 1977-10-11 | Process for the continuous preparation of acetoacetamides |
| BE181871A BE859889A (fr) | 1976-10-21 | 1977-10-19 | Procede de preparation en continu d'acetoacetamides |
| IT7751477A IT1090534B (it) | 1976-10-21 | 1977-10-19 | Procedimento per produrre continuamente aceto-acetammidi |
| CH1281277A CH632233A5 (de) | 1976-10-21 | 1977-10-20 | Verfahren zur kontinuierlichen herstellung von acetoacetamiden. |
| FR7731577A FR2368467A1 (fr) | 1976-10-21 | 1977-10-20 | Procede de preparation en continu d'acetoacetamides |
| GB43695/77A GB1588027A (en) | 1976-10-21 | 1977-10-20 | Manufacture of acetoacetamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2647499A DE2647499C2 (de) | 1976-10-21 | 1976-10-21 | Verfahren zur kontinuierlichen Herstellung von Acetoacetamiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2647499A1 DE2647499A1 (de) | 1978-04-27 |
| DE2647499C2 true DE2647499C2 (de) | 1982-04-01 |
Family
ID=5990979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2647499A Expired DE2647499C2 (de) | 1976-10-21 | 1976-10-21 | Verfahren zur kontinuierlichen Herstellung von Acetoacetamiden |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4129596A (enExample) |
| BE (1) | BE859889A (enExample) |
| CH (1) | CH632233A5 (enExample) |
| DE (1) | DE2647499C2 (enExample) |
| FR (1) | FR2368467A1 (enExample) |
| GB (1) | GB1588027A (enExample) |
| IL (1) | IL53008A (enExample) |
| IT (1) | IT1090534B (enExample) |
| NL (1) | NL7710442A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2853887A1 (de) * | 1978-12-14 | 1980-07-03 | Consortium Elektrochem Ind | Verfahren zur herstellung von beta -isobutyrylaminocrotonsaeureamid |
| US5025106A (en) * | 1990-10-22 | 1991-06-18 | Eastman Kodak Company | Preparation of aqueous solutions of acetoacetamide |
| DE4335613A1 (de) * | 1993-10-19 | 1995-04-20 | Hoechst Ag | Verfahren zur Herstellung von Acetoacetarylamiden |
| US5569318A (en) * | 1994-06-24 | 1996-10-29 | Applied Research, Inc. | Frictionizing composition |
| ATE186554T1 (de) * | 1996-02-23 | 1999-11-15 | Basf Ag | Kraft- und schmierstoffadditive |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3065268A (en) * | 1962-11-20 | Preparation of concentrated aceto | ||
| FR1202705A (fr) * | 1957-10-03 | 1960-01-12 | Lonza Ag | Procédé de préparation de solutions concentrées d'amide acétylacétique |
| DE1142859B (de) * | 1960-05-27 | 1963-01-31 | Lonza Ag | Verfahren zur Herstellung von Acetessigsaeureamiden |
| CH395051A (de) * | 1960-05-27 | 1965-07-15 | Lonza Ag | Verfahren zur Herstellung von Acetessigamiden |
| US3778474A (en) * | 1970-10-06 | 1973-12-11 | Lonza Ag | Production of acetoacetyl amides |
| NL7201363A (enExample) * | 1971-02-12 | 1972-08-15 |
-
1976
- 1976-10-21 DE DE2647499A patent/DE2647499C2/de not_active Expired
-
1977
- 1977-09-23 NL NL7710442A patent/NL7710442A/xx not_active Application Discontinuation
- 1977-09-28 IL IL53008A patent/IL53008A/xx unknown
- 1977-10-11 US US05/840,709 patent/US4129596A/en not_active Expired - Lifetime
- 1977-10-19 BE BE181871A patent/BE859889A/xx not_active IP Right Cessation
- 1977-10-19 IT IT7751477A patent/IT1090534B/it active
- 1977-10-20 CH CH1281277A patent/CH632233A5/de not_active IP Right Cessation
- 1977-10-20 GB GB43695/77A patent/GB1588027A/en not_active Expired
- 1977-10-20 FR FR7731577A patent/FR2368467A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1588027A (en) | 1981-04-15 |
| IL53008A (en) | 1981-03-31 |
| IT1090534B (it) | 1985-06-26 |
| FR2368467A1 (fr) | 1978-05-19 |
| BE859889A (fr) | 1978-04-19 |
| DE2647499A1 (de) | 1978-04-27 |
| NL7710442A (nl) | 1978-04-25 |
| FR2368467B1 (enExample) | 1979-03-02 |
| IL53008A0 (en) | 1977-11-30 |
| CH632233A5 (de) | 1982-09-30 |
| US4129596A (en) | 1978-12-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8126 | Change of the secondary classification |
Ipc: C07C102/02 |
|
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |