GB2013180A - Process for Preparing N- Ethylethylenediamine - Google Patents
Process for Preparing N- EthylethylenediamineInfo
- Publication number
- GB2013180A GB2013180A GB7849118A GB7849118A GB2013180A GB 2013180 A GB2013180 A GB 2013180A GB 7849118 A GB7849118 A GB 7849118A GB 7849118 A GB7849118 A GB 7849118A GB 2013180 A GB2013180 A GB 2013180A
- Authority
- GB
- United Kingdom
- Prior art keywords
- eda
- reaction mixture
- hydrocarbon solvent
- weight
- halide
- 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.)
- Granted
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
- C07C209/06—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
Abstract
There are provided processes for preparing N-ethylethylenediamine (NEED) in good yield and purity. In one embodiment the process comprises reacting ethylenediamine (EDA) and an ethyl halide at a mole ratio of EPA to said ethyl halide of about 1-20:1 and a temperature of from about -10 DEG C. to about 120 DEG C. in the presence of about 0-50% by weight of water to obtain an alkylation reaction mixture; neutralizing said reaction mixture by contacting with an aqueous solution containing about 1-2 molecular equivalents of an inorganic alkalizing agent based on the ethyl halide; separating the aqueous layer from the neutralized organic layer and adding to said organic layer about 0.2-100% by weight, based on the weight of said organic layer, of a suitable aliphatic of hydrocarbon solvent; azeotropically fractionally distilling all water and EPA from the resulting mixture; and fractionally distilling the resulting reaction mixture to remove residual hydrocarbon solvent and recover NEED. In a modified embodiment the process comprises (a) reacting an ethyl halide and the ethylenediamine (EDA) at a mole ratio of EDA to said ethyl halide of about 1-20 to 1, and at a temperature of about -10 DEG C to about 120 DEG C under anhydrous conditions to obtain an alkylation reaction mixture; (b) adding to said reaction mixture about 0.2-30% by weight of a suitable aliphatic hydrocarbon solvent, based on the weight of said reaction mixture; (c) fractionally distilling the EDA and said aliphatic hydrocarbon solvent to essentially remove EDA; (d) neutralizing the resulting mixture by contacting it with at least 0.9 molecular equivalent of a suitable alkalizing agent, per mole of said ethyl halide, to form a slurry of an alkali halide precipitate; (e) separating said alkali halide precipitate from said slurry and recovering the resulting mother liquor; (f) washing said separated alkali halide with said aliphatic hydrocarbon solvent; (g) fractionally distilling a combination of said mother liquor from step (e) plus recovered aliphatic hydrocarbon wash liquor from step (f) to remove essentially all water and residual EDA from the resulting mixture; and (h) fractionally distilling said resulting mixture to remove residual aliphatic hydrocarbon solvent and recover said NEED.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87345078A | 1978-01-30 | 1978-01-30 | |
| US96097278A | 1978-11-15 | 1978-11-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2013180A true GB2013180A (en) | 1979-08-08 |
| GB2013180B GB2013180B (en) | 1982-05-12 |
Family
ID=27128297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7849118A Expired GB2013180B (en) | 1978-01-30 | 1978-12-19 | Process for preparing n ethylethylenediamine |
Country Status (17)
| Country | Link |
|---|---|
| AR (1) | AR223161A1 (en) |
| AT (1) | AT364345B (en) |
| AU (1) | AU523012B2 (en) |
| CA (1) | CA1120059A (en) |
| CH (1) | CH642616A5 (en) |
| DD (1) | DD141305A5 (en) |
| DE (1) | DE2900060A1 (en) |
| DK (1) | DK153541C (en) |
| ES (1) | ES477283A1 (en) |
| FI (1) | FI67207C (en) |
| FR (1) | FR2415618A1 (en) |
| GB (1) | GB2013180B (en) |
| HU (1) | HU182922B (en) |
| IL (1) | IL56176A (en) |
| IT (1) | IT1116499B (en) |
| NL (1) | NL190159C (en) |
| SE (1) | SE446628B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0254229A1 (en) * | 1986-07-18 | 1988-01-27 | MITSUI TOATSU CHEMICALS, Inc. | Process for producing N,N'-dialkylalkanediamines |
| WO2000056697A1 (en) * | 1999-03-19 | 2000-09-28 | Mitsui Chemicals, Inc | Novel process for the preparation of n,n'-dialkylalkanediamines |
| CN102816071A (en) * | 2012-08-25 | 2012-12-12 | 太原理工大学 | Synthesis method of N-ethyl ethylene diamine |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2929841A1 (en) * | 1979-06-14 | 1980-12-18 | American Cyanamid Co | METHOD FOR PRODUCING N-ALKYLAETHYLENE DIAMINES |
| CN102260175B (en) * | 2011-06-08 | 2013-11-20 | 浙江大学 | Method for synthesizing 2-aminoethyl(ethyl)amine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1130814B (en) * | 1959-12-03 | 1962-06-07 | Basf Ag | Process for the continuous dewatering of ethylene diamines |
| BE626346A (en) * | 1961-12-21 | |||
| GB1507379A (en) * | 1976-08-05 | 1978-04-12 | Bp Chem Int Ltd | Hydrocarbyl substituted polyamines |
-
1978
- 1978-12-11 IL IL56176A patent/IL56176A/en unknown
- 1978-12-14 AU AU42550/78A patent/AU523012B2/en not_active Expired
- 1978-12-18 FI FI783891A patent/FI67207C/en not_active IP Right Cessation
- 1978-12-19 GB GB7849118A patent/GB2013180B/en not_active Expired
- 1978-12-29 CA CA000318858A patent/CA1120059A/en not_active Expired
-
1979
- 1979-01-02 AR AR275041A patent/AR223161A1/en active
- 1979-01-02 DE DE19792900060 patent/DE2900060A1/en active Granted
- 1979-01-25 FR FR7901952A patent/FR2415618A1/en active Granted
- 1979-01-26 AT AT0060679A patent/AT364345B/en not_active IP Right Cessation
- 1979-01-26 HU HU79AE556A patent/HU182922B/en not_active IP Right Cessation
- 1979-01-26 IT IT47792/79A patent/IT1116499B/en active
- 1979-01-29 CH CH86279A patent/CH642616A5/en not_active IP Right Cessation
- 1979-01-29 DK DK036379A patent/DK153541C/en not_active IP Right Cessation
- 1979-01-29 SE SE7900766A patent/SE446628B/en not_active IP Right Cessation
- 1979-01-30 NL NLAANVRAGE7900746,A patent/NL190159C/en not_active IP Right Cessation
- 1979-01-30 DD DD79210710A patent/DD141305A5/en unknown
- 1979-01-30 ES ES477283A patent/ES477283A1/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0254229A1 (en) * | 1986-07-18 | 1988-01-27 | MITSUI TOATSU CHEMICALS, Inc. | Process for producing N,N'-dialkylalkanediamines |
| WO2000056697A1 (en) * | 1999-03-19 | 2000-09-28 | Mitsui Chemicals, Inc | Novel process for the preparation of n,n'-dialkylalkanediamines |
| US6242651B1 (en) | 1999-03-19 | 2001-06-05 | Mitsui Chemicals, Inc. | Process for the preparation of N,N′-dialkylalkanediamines |
| CN102816071A (en) * | 2012-08-25 | 2012-12-12 | 太原理工大学 | Synthesis method of N-ethyl ethylene diamine |
| CN102816071B (en) * | 2012-08-25 | 2014-05-07 | 太原理工大学 | Synthesis method of N-ethyl ethylene diamine |
Also Published As
| Publication number | Publication date |
|---|---|
| SE7900766L (en) | 1979-07-31 |
| SE446628B (en) | 1986-09-29 |
| AU4255078A (en) | 1979-08-09 |
| IT7947792A0 (en) | 1979-01-26 |
| IL56176A0 (en) | 1979-03-12 |
| IL56176A (en) | 1982-03-31 |
| CH642616A5 (en) | 1984-04-30 |
| FI783891A (en) | 1979-07-31 |
| DK36379A (en) | 1979-07-31 |
| FR2415618A1 (en) | 1979-08-24 |
| DK153541B (en) | 1988-07-25 |
| FI67207B (en) | 1984-10-31 |
| DE2900060C2 (en) | 1988-01-21 |
| CA1120059A (en) | 1982-03-16 |
| GB2013180B (en) | 1982-05-12 |
| AT364345B (en) | 1981-10-12 |
| DK153541C (en) | 1988-12-05 |
| HU182922B (en) | 1984-03-28 |
| NL190159C (en) | 1993-11-16 |
| NL7900746A (en) | 1979-08-01 |
| ATA60679A (en) | 1981-03-15 |
| AU523012B2 (en) | 1982-07-08 |
| DE2900060A1 (en) | 1979-08-09 |
| IT1116499B (en) | 1986-02-10 |
| FR2415618B1 (en) | 1983-09-09 |
| NL190159B (en) | 1993-06-16 |
| AR223161A1 (en) | 1981-07-31 |
| ES477283A1 (en) | 1979-10-16 |
| DD141305A5 (en) | 1980-04-23 |
| FI67207C (en) | 1985-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19981218 |