SE446628B - Forfarande for framstellning av n-etylenetylendiamin - Google Patents
Forfarande for framstellning av n-etylenetylendiaminInfo
- Publication number
- SE446628B SE446628B SE7900766A SE7900766A SE446628B SE 446628 B SE446628 B SE 446628B SE 7900766 A SE7900766 A SE 7900766A SE 7900766 A SE7900766 A SE 7900766A SE 446628 B SE446628 B SE 446628B
- Authority
- SE
- Sweden
- Prior art keywords
- aliphatic hydrocarbon
- reaction mixture
- ethylenediamine
- process according
- heptane
- Prior art date
Links
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims 2
- 239000005977 Ethylene Substances 0.000 title 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 66
- 239000011541 reaction mixture Substances 0.000 claims description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 20
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- -1 ethyl halide Chemical class 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 claims description 7
- 239000012452 mother liquor Substances 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 238000004064 recycling Methods 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 5
- 229960003750 ethyl chloride Drugs 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000003113 alkalizing effect Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 238000003822 preparative gas chromatography Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002171 ethylene diamines Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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 |
|---|---|
| SE7900766L SE7900766L (sv) | 1979-07-31 |
| SE446628B true SE446628B (sv) | 1986-09-29 |
Family
ID=27128297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7900766A SE446628B (sv) | 1978-01-30 | 1979-01-29 | Forfarande for framstellning av n-etylenetylendiamin |
Country Status (17)
| Country | Link |
|---|---|
| AR (1) | AR223161A1 (en, 2012) |
| AT (1) | AT364345B (en, 2012) |
| AU (1) | AU523012B2 (en, 2012) |
| CA (1) | CA1120059A (en, 2012) |
| CH (1) | CH642616A5 (en, 2012) |
| DD (1) | DD141305A5 (en, 2012) |
| DE (1) | DE2900060A1 (en, 2012) |
| DK (1) | DK153541C (en, 2012) |
| ES (1) | ES477283A1 (en, 2012) |
| FI (1) | FI67207C (en, 2012) |
| FR (1) | FR2415618A1 (en, 2012) |
| GB (1) | GB2013180B (en, 2012) |
| HU (1) | HU182922B (en, 2012) |
| IL (1) | IL56176A (en, 2012) |
| IT (1) | IT1116499B (en, 2012) |
| NL (1) | NL190159C (en, 2012) |
| SE (1) | SE446628B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2929841A1 (de) * | 1979-06-14 | 1980-12-18 | American Cyanamid Co | Verfahren zur herstellung von n-alkylaethylendiaminen |
| JP2501562B2 (ja) * | 1986-07-18 | 1996-05-29 | 三井東圧化学株式会社 | Ｎ，ｎ▲’▼−ジアルキルアルカンジアミン類の製造方法 |
| EP1081127B1 (en) * | 1999-03-19 | 2005-12-28 | Mitsui Chemicals, Inc. | Novel process for the preparation of n,n'-dialkylalkanediamines |
| CN102260175B (zh) * | 2011-06-08 | 2013-11-20 | 浙江大学 | N-乙基乙二胺的合成方法 |
| CN102816071B (zh) * | 2012-08-25 | 2014-05-07 | 太原理工大学 | 一种n-乙基乙二胺的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1130814B (de) * | 1959-12-03 | 1962-06-07 | Basf Ag | Verfahren zur kontinuierlichen Entwaesserung von AEthylendiaminen |
| NL286808A (en, 2012) * | 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/xx unknown
- 1978-12-14 AU AU42550/78A patent/AU523012B2/en not_active Expired
- 1978-12-18 FI FI783891A patent/FI67207C/fi 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 DE DE19792900060 patent/DE2900060A1/de active Granted
- 1979-01-02 AR AR275041A patent/AR223161A1/es active
- 1979-01-25 FR FR7901952A patent/FR2415618A1/fr active Granted
- 1979-01-26 IT IT47792/79A patent/IT1116499B/it active
- 1979-01-26 AT AT0060679A patent/AT364345B/de not_active IP Right Cessation
- 1979-01-26 HU HU79AE556A patent/HU182922B/hu not_active IP Right Cessation
- 1979-01-29 SE SE7900766A patent/SE446628B/sv not_active IP Right Cessation
- 1979-01-29 DK DK036379A patent/DK153541C/da not_active IP Right Cessation
- 1979-01-29 CH CH86279A patent/CH642616A5/de not_active IP Right Cessation
- 1979-01-30 DD DD79210710A patent/DD141305A5/de unknown
- 1979-01-30 ES ES477283A patent/ES477283A1/es not_active Expired
- 1979-01-30 NL NLAANVRAGE7900746,A patent/NL190159C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7900746A (nl) | 1979-08-01 |
| IL56176A (en) | 1982-03-31 |
| DE2900060A1 (de) | 1979-08-09 |
| DK153541C (da) | 1988-12-05 |
| FI67207B (fi) | 1984-10-31 |
| DE2900060C2 (en, 2012) | 1988-01-21 |
| HU182922B (en) | 1984-03-28 |
| ES477283A1 (es) | 1979-10-16 |
| FR2415618A1 (fr) | 1979-08-24 |
| DD141305A5 (de) | 1980-04-23 |
| ATA60679A (de) | 1981-03-15 |
| IT1116499B (it) | 1986-02-10 |
| FI783891A7 (fi) | 1979-07-31 |
| AR223161A1 (es) | 1981-07-31 |
| IT7947792A0 (it) | 1979-01-26 |
| AU523012B2 (en) | 1982-07-08 |
| NL190159C (nl) | 1993-11-16 |
| DK36379A (da) | 1979-07-31 |
| AU4255078A (en) | 1979-08-09 |
| FR2415618B1 (en, 2012) | 1983-09-09 |
| CH642616A5 (de) | 1984-04-30 |
| AT364345B (de) | 1981-10-12 |
| FI67207C (fi) | 1985-02-11 |
| CA1120059A (en) | 1982-03-16 |
| DK153541B (da) | 1988-07-25 |
| IL56176A0 (en) | 1979-03-12 |
| GB2013180B (en) | 1982-05-12 |
| SE7900766L (sv) | 1979-07-31 |
| GB2013180A (en) | 1979-08-08 |
| NL190159B (nl) | 1993-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
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| NUG | Patent has lapsed |
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