GB1588027A - Manufacture of acetoacetamides - Google Patents
Manufacture of acetoacetamides Download PDFInfo
- Publication number
- GB1588027A GB1588027A GB43695/77A GB4369577A GB1588027A GB 1588027 A GB1588027 A GB 1588027A GB 43695/77 A GB43695/77 A GB 43695/77A GB 4369577 A GB4369577 A GB 4369577A GB 1588027 A GB1588027 A GB 1588027A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reaction
- carbon atoms
- denotes
- alkyl radical
- diketene
- 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 claims description 8
- GCPWJFKTWGFEHH-UHFFFAOYSA-N acetoacetamide Chemical class CC(=O)CC(N)=O GCPWJFKTWGFEHH-UHFFFAOYSA-N 0.000 title claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 32
- 230000008569 process Effects 0.000 claims description 29
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000010924 continuous production Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 239000000047 product Substances 0.000 description 12
- -1 alkyl acetate Chemical compound 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 7
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 4
- ATWLCPHWYPSRBQ-UHFFFAOYSA-N N-Methylacetoacetamide Chemical compound CNC(=O)CC(C)=O ATWLCPHWYPSRBQ-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- SAIKULLUBZKPDA-UHFFFAOYSA-N Bis(2-ethylhexyl) amine Chemical compound CCCCC(CC)CNCC(CC)CCCC SAIKULLUBZKPDA-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000003223 protective agent Substances 0.000 description 2
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- YACKQTNFQKTZTH-UHFFFAOYSA-N 3-oxo-n,n-di(propan-2-yl)butanamide Chemical compound CC(C)N(C(C)C)C(=O)CC(C)=O YACKQTNFQKTZTH-UHFFFAOYSA-N 0.000 description 1
- NMRMDDPBAMBJEH-UHFFFAOYSA-N C(CCCCC)NCCCCCC.C(CCCC)NCCCCC.C(CCC)NCCCC Chemical compound C(CCCCC)NCCCCCC.C(CCCC)NCCCCC.C(CCC)NCCCC NMRMDDPBAMBJEH-UHFFFAOYSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QRXXOKQEZONCSX-UHFFFAOYSA-N butan-1-amine;propan-2-amine Chemical compound CC(C)N.CCCCN QRXXOKQEZONCSX-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- ULBJLGYNFGZJDX-UHFFFAOYSA-N n-decyldecan-1-amine;n-nonylnonan-1-amine Chemical compound CCCCCCCCCNCCCCCCCCC.CCCCCCCCCCNCCCCCCCCCC ULBJLGYNFGZJDX-UHFFFAOYSA-N 0.000 description 1
- MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 description 1
- RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000010944 pre-mature reactiony Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 230000035899 viability Effects 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)
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 (1)
| Publication Number | Publication Date |
|---|---|
| GB1588027A true GB1588027A (en) | 1981-04-15 |
Family
ID=5990979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB43695/77A Expired GB1588027A (en) | 1976-10-21 | 1977-10-20 | Manufacture of acetoacetamides |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5523486A (en) * | 1993-10-19 | 1996-06-04 | Hoechst Ag | Preparation of acetoacetarylamides |
Families Citing this family (4)
| 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 |
| 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5523486A (en) * | 1993-10-19 | 1996-06-04 | Hoechst Ag | Preparation of acetoacetarylamides |
Also Published As
| Publication number | Publication date |
|---|---|
| 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 |
| DE2647499C2 (de) | 1982-04-01 |
| 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 |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |