FR2071278A5 - Tertiary aliphatic amine production by - amination of alkyl halides - Google Patents
Tertiary aliphatic amine production by - amination of alkyl halidesInfo
- Publication number
- FR2071278A5 FR2071278A5 FR6944604A FR6944604A FR2071278A5 FR 2071278 A5 FR2071278 A5 FR 2071278A5 FR 6944604 A FR6944604 A FR 6944604A FR 6944604 A FR6944604 A FR 6944604A FR 2071278 A5 FR2071278 A5 FR 2071278A5
- Authority
- FR
- France
- Prior art keywords
- pref
- amine
- sec
- halide
- alkyl
- 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
- 150000001350 alkyl halides Chemical class 0.000 title abstract 5
- 238000005576 amination reaction Methods 0.000 title abstract 2
- 150000003510 tertiary aliphatic amines Chemical class 0.000 title 1
- 150000001412 amines Chemical class 0.000 abstract 7
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 1
- 150000001347 alkyl bromides Chemical class 0.000 abstract 1
- 150000001348 alkyl chlorides Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 238000005647 hydrohalogenation reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 230000000630 rising effect Effects 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 239000004711 α-olefin Substances 0.000 abstract 1
Classifications
-
- 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
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2415—Tubular reactors
-
- 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
- B01J14/00—Chemical processes in general for reacting liquids with liquids; Apparatus specially adapted therefor
-
- 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
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00076—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements inside the reactor
- B01J2219/00083—Coils
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Tert. aliphatic amine preparation by amination of alkyl halide with an aliphatic sec. amine takes place by preparing a reaction mixture in 2 parts. First consists of least one alkyl halide, predominantly 1-haloalkane, and second of an aliphatic sec. amine in a dipolar aprotic solvent, suitable for dissolving halide and sec. amine but not dissolving the tertiary amine when cold. First part pref. contains >=85 wt.% 1-haloalkane, pref. 4-22 (8-18) C alkyl bromide or -chloride, more pref. prepared by radical hydrohalogenation of alpha-olefins. Pref. each alkyl group of sec. amine NHR'R" has 1-18 (1-4)C atoms. Pref. solvents are DMF, hexamethyl phosphotriamide, THF and N-methyl pyrrolidone, pref. in 0.8-2 wt./wt. alkyl halide. Pref. mole ratio sec. amine : alkyl halide is 2 : 1, excess sec. amine being sufficient to bind hydrogen halide released. Pref. process takes place continuously at 20-150 degrees C., 2 bar. Pref. sec. amine in solvent and first part are charged upwards into vertical pref. glass reactor, heated with superimposed heating elements with temps. rising towards top. Product flows from top into cooler and decanter.
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6944604A FR2071278A5 (en) | 1969-12-23 | 1969-12-23 | Tertiary aliphatic amine production by - amination of alkyl halides |
| DE2062548A DE2062548C3 (en) | 1969-12-23 | 1970-12-18 | Process for the preparation of tertiary aliphatic amines by amination of an alkyl halide with a secondary aliphatic amine |
| GB6049370A GB1337285A (en) | 1969-12-23 | 1970-12-21 | Method of synthesizing tertiary aliphatic amines by amination of alkyl halides |
| US00099853A US3764626A (en) | 1969-12-23 | 1970-12-21 | Method of synthetizing tertiary aliphatic amines by amination of alkyl halides |
| NLAANVRAGE7018610,A NL170728C (en) | 1969-12-23 | 1970-12-21 | PROCESS FOR THE PREPARATION OF TERTIARY ALIPHATIC AMINES. |
| ES386744A ES386744A1 (en) | 1969-12-23 | 1970-12-22 | Method of synthetizing tertiary aliphatic amines by amination of alkyl halides |
| LU62297D LU62297A1 (en) | 1969-12-23 | 1970-12-22 | |
| JP70115229A JPS5339403B1 (en) | 1969-12-23 | 1970-12-22 | |
| SE7017390A SE371814B (en) | 1969-12-23 | 1970-12-22 | |
| CH1898570A CH529095A (en) | 1969-12-23 | 1970-12-22 | Continuous or batch process for the production of tertiary aliphatic amines by amination of alkyl halides |
| BE760696A BE760696A (en) | 1969-12-23 | 1970-12-22 | PROCESS FOR SYNTHESIS OF TERTIARY ALIPHATIC AMINES BY AMINATION OF ALKYL HALOGENIDES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6944604A FR2071278A5 (en) | 1969-12-23 | 1969-12-23 | Tertiary aliphatic amine production by - amination of alkyl halides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2071278A5 true FR2071278A5 (en) | 1971-09-17 |
Family
ID=9045043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR6944604A Expired FR2071278A5 (en) | 1969-12-23 | 1969-12-23 | Tertiary aliphatic amine production by - amination of alkyl halides |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2071278A5 (en) |
-
1969
- 1969-12-23 FR FR6944604A patent/FR2071278A5/en not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CD | Change of name or company name | ||
| TP | Transmission of property | ||
| CD | Change of name or company name | ||
| TP | Transmission of property | ||
| TP | Transmission of property |