CA1072117A - Process for the preparation of acetoacetylaryl-amides - Google Patents
Process for the preparation of acetoacetylaryl-amidesInfo
- Publication number
- CA1072117A CA1072117A CA251,319A CA251319A CA1072117A CA 1072117 A CA1072117 A CA 1072117A CA 251319 A CA251319 A CA 251319A CA 1072117 A CA1072117 A CA 1072117A
- Authority
- CA
- Canada
- Prior art keywords
- diketene
- reaction
- acetic acid
- product
- temperature
- 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 abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 42
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 12
- 239000000839 emulsion Substances 0.000 claims abstract description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 71
- 239000000047 product Substances 0.000 claims description 31
- 239000000243 solution Substances 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000001816 cooling Methods 0.000 claims description 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000012429 reaction media Substances 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- -1 methoxy, ethoxy Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000004986 phenylenediamines Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 239000007787 solid Substances 0.000 abstract description 4
- 239000007900 aqueous suspension Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000000203 mixture Substances 0.000 description 21
- 229960000583 acetic acid Drugs 0.000 description 20
- 206010001497 Agitation Diseases 0.000 description 15
- 238000013019 agitation Methods 0.000 description 15
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 239000012452 mother liquor Substances 0.000 description 8
- 239000000376 reactant Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 3
- BFVHBHKMLIBQNN-UHFFFAOYSA-N n-(2-chlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1Cl BFVHBHKMLIBQNN-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 2
- WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 230000000332 continued effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- HGVIAKXYAZRSEG-UHFFFAOYSA-N n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(C)C=C1C HGVIAKXYAZRSEG-UHFFFAOYSA-N 0.000 description 2
- PJFIAKRRJLGWMD-UHFFFAOYSA-N n-(2,5-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=C(OC)C(NC(=O)CC(C)=O)=C1 PJFIAKRRJLGWMD-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation 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
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FSUMZUVANZAHBW-UHFFFAOYSA-N n,n-dimethoxyaniline Chemical class CON(OC)C1=CC=CC=C1 FSUMZUVANZAHBW-UHFFFAOYSA-N 0.000 description 1
- AJDFNQRIAVDGQT-UHFFFAOYSA-N n-chloro-4-[4-(chloroamino)phenyl]aniline Chemical class C1=CC(NCl)=CC=C1C1=CC=C(NCl)C=C1 AJDFNQRIAVDGQT-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- JGGQWILNAAODRS-UHFFFAOYSA-N n-methyl-4-[4-(methylamino)phenyl]aniline Chemical class C1=CC(NC)=CC=C1C1=CC=C(NC)C=C1 JGGQWILNAAODRS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752519036 DE2519036A1 (de) | 1975-04-29 | 1975-04-29 | Verfahren zur herstellung von acetoacetylarylamiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1072117A true CA1072117A (en) | 1980-02-19 |
Family
ID=5945309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA251,319A Expired CA1072117A (en) | 1975-04-29 | 1976-04-28 | Process for the preparation of acetoacetylaryl-amides |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS51131836A (enExample) |
| BE (1) | BE841285A (enExample) |
| BR (1) | BR7602624A (enExample) |
| CA (1) | CA1072117A (enExample) |
| CH (1) | CH608786A5 (enExample) |
| DE (1) | DE2519036A1 (enExample) |
| FR (1) | FR2309514A1 (enExample) |
| GB (1) | GB1541460A (enExample) |
| IN (1) | IN143520B (enExample) |
| IT (1) | IT1058978B (enExample) |
| NL (1) | NL7604350A (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2749327A1 (de) * | 1977-11-04 | 1979-05-17 | Hoechst Ag | Verfahren zur herstellung von acetoacetylaminobenzolen |
| DE3046367A1 (de) * | 1980-12-09 | 1982-07-08 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von 1-acetoacetylamino-4-chlor-2,5-dimethoxybenzol |
| DE3731912A1 (de) * | 1987-02-25 | 1988-09-08 | Hoechst Ag | Verfahren zur herstellung von acetoacetylarylamiden bzw. -heteroarylamiden desaktivierter aromaten |
| DE4335613A1 (de) * | 1993-10-19 | 1995-04-20 | Hoechst Ag | Verfahren zur Herstellung von Acetoacetarylamiden |
| IN190321B (enExample) | 1998-03-25 | 2003-07-19 | Lonza Ag | |
| US7144993B2 (en) | 2001-12-11 | 2006-12-05 | Ciba Specialty Chemicals Corp. | Process for the preparation of 4-methyl-7-aminoquinolones |
| EP1712544A1 (de) * | 2005-04-12 | 2006-10-18 | Lonza Ag | Verfahren zur Herstellung von Acetessigsäurearylamiden |
| CN103224455B (zh) * | 2013-04-19 | 2014-10-29 | 南通醋酸化工股份有限公司 | 一种n-乙酰乙酰苯胺的制备方法 |
| CN104292121B (zh) * | 2014-09-05 | 2016-08-31 | 南通醋酸化工股份有限公司 | 一种减少邻甲基-n-乙酰乙酰苯胺生产中副产物的方法 |
| CN105418422A (zh) * | 2015-12-21 | 2016-03-23 | 常熟市柏伦精细化工有限公司 | 一种新型的色酚as-irg的制备工艺 |
| CN113979883A (zh) * | 2021-12-08 | 2022-01-28 | 新华制药（寿光）有限公司 | 一种乙酰乙酰苯胺高效精制工艺及其设备 |
-
1975
- 1975-04-29 DE DE19752519036 patent/DE2519036A1/de active Pending
-
1976
- 1976-04-23 CH CH765155A patent/CH608786A5/xx not_active IP Right Cessation
- 1976-04-23 NL NL7604350A patent/NL7604350A/xx not_active Application Discontinuation
- 1976-04-27 IT IT2273676A patent/IT1058978B/it active
- 1976-04-27 IN IN734/CAL/1976A patent/IN143520B/en unknown
- 1976-04-28 BR BR7602624A patent/BR7602624A/pt unknown
- 1976-04-28 JP JP4793176A patent/JPS51131836A/ja active Pending
- 1976-04-28 CA CA251,319A patent/CA1072117A/en not_active Expired
- 1976-04-29 GB GB1748376A patent/GB1541460A/en not_active Expired
- 1976-04-29 BE BE166576A patent/BE841285A/xx unknown
- 1976-04-29 FR FR7612717A patent/FR2309514A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1541460A (en) | 1979-02-28 |
| BR7602624A (pt) | 1976-11-23 |
| IT1058978B (it) | 1982-05-10 |
| FR2309514B1 (enExample) | 1980-08-14 |
| DE2519036A1 (de) | 1976-11-11 |
| JPS51131836A (en) | 1976-11-16 |
| IN143520B (enExample) | 1977-12-17 |
| BE841285A (fr) | 1976-10-29 |
| CH608786A5 (en) | 1979-01-31 |
| FR2309514A1 (fr) | 1976-11-26 |
| NL7604350A (nl) | 1976-11-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 19970219 |