GB673433A - Improvements in and relating to the production of secondary cyclic amines - Google Patents
Improvements in and relating to the production of secondary cyclic aminesInfo
- Publication number
- GB673433A GB673433A GB8665/50A GB866550A GB673433A GB 673433 A GB673433 A GB 673433A GB 8665/50 A GB8665/50 A GB 8665/50A GB 866550 A GB866550 A GB 866550A GB 673433 A GB673433 A GB 673433A
- Authority
- GB
- United Kingdom
- Prior art keywords
- copper
- catalyst
- alumina
- amines
- amine
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/18—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/72—Copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Secondary cyclic amines are prepared by treating a primary cyclic amine with an aliphatic carbinol in the presence of a catalyst comprising a mixture of metallic copper, alumina, and one or more difficulty reducible metal oxides. The alumina is preferably activated alumina. The other difficulty reducible metal oxide used acts as an activator and for this the metals of Group II are specially advantageous. Examples of suitable oxides in decreasing order of preference are the oxides of calcium, zinc, chromium, magnesium, ferrous iron, cadmium, and potassium. Preferred amounts of copper in the catalyst comprises from 2-20 per cent. The molar ratio of activating difficulty reducible oxide to copper is from 0.2 : 1 to 4 : 1. The catalyst is prepared by impregnating alumina with a salt of copper and of the difficulty reducible metal oxide selected, and calcining at 250-400 DEG C. If desired the catalyst may be supported on a carrier. The reaction of the amine with the alcohol takes place at 200-275 DEG C., preferably as a continuous process. It is stated that by the use of the special catalysts according to the invention, and by the use of an excess of alcohol, the substantial total suppression of the formation of tertiary amines is possible. Amines mentioned which may be produced according to the invention include N-methylaniline, other N-alkylanilines, N-alkyltoluidines, N - alkylnaphthylamines, N - alkylcyclohexylamines, and secondary heterocyclic amines. When unsaturated alcohols are used such as allyl and methallyl alcohols, the product is a saturated amine if the treatment is carried out in the presence of hydrogen. Polyhydroxy alcohols, such as glycol and diethylene glycol may also be used. Examples of varying reaction conditions and different catalysts are given.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US673433XA | 1949-04-11 | 1949-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB673433A true GB673433A (en) | 1952-06-04 |
Family
ID=22075369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8665/50A Expired GB673433A (en) | 1949-04-11 | 1950-04-06 | Improvements in and relating to the production of secondary cyclic amines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB673433A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5159115A (en) * | 1989-08-18 | 1992-10-27 | Amoco Corporation | Catalyzed gas-phase mono N-alkylation of aromatic primary amines |
| CN113061091A (en) * | 2021-03-16 | 2021-07-02 | 南京林业大学 | Preparation method of N-alkylated derivative of primary amine compound |
-
1950
- 1950-04-06 GB GB8665/50A patent/GB673433A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5159115A (en) * | 1989-08-18 | 1992-10-27 | Amoco Corporation | Catalyzed gas-phase mono N-alkylation of aromatic primary amines |
| CN113061091A (en) * | 2021-03-16 | 2021-07-02 | 南京林业大学 | Preparation method of N-alkylated derivative of primary amine compound |
| CN113061091B (en) * | 2021-03-16 | 2023-12-05 | 南京林业大学 | Preparation method of N-alkylated derivative of primary amine compound |
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