DD141305A5 - Verfahren zur herstellung von n-aethylaethylendiamin - Google Patents
Verfahren zur herstellung von n-aethylaethylendiamin Download PDFInfo
- Publication number
- DD141305A5 DD141305A5 DD79210710A DD21071079A DD141305A5 DD 141305 A5 DD141305 A5 DD 141305A5 DD 79210710 A DD79210710 A DD 79210710A DD 21071079 A DD21071079 A DD 21071079A DD 141305 A5 DD141305 A5 DD 141305A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- eda
- hydrocarbon solvent
- aliphatic hydrocarbon
- reaction mixture
- need
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 118
- 239000002904 solvent Substances 0.000 claims description 46
- 239000011541 reaction mixture Substances 0.000 claims description 44
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 43
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 35
- 239000010410 layer Substances 0.000 claims description 23
- 239000004215 Carbon black (E152) Substances 0.000 claims description 21
- 229930195733 hydrocarbon Natural products 0.000 claims description 21
- 150000002430 hydrocarbons Chemical class 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 20
- 238000004821 distillation Methods 0.000 claims description 17
- -1 ethyl halide Chemical class 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 230000003113 alkalizing effect Effects 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 238000004508 fractional distillation Methods 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 8
- 239000012452 mother liquor Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000002002 slurry Substances 0.000 claims description 7
- 238000005804 alkylation reaction Methods 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 6
- 239000000284 extract Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000005201 scrubbing Methods 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 12
- 229960003750 ethyl chloride Drugs 0.000 description 12
- 239000012071 phase Substances 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000011521 glass Substances 0.000 description 8
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000002051 biphasic effect Effects 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 4
- 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
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 150000002171 ethylene diamines Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010626 work up procedure Methods 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 (1)
| Publication Number | Publication Date |
|---|---|
| DD141305A5 true DD141305A5 (de) | 1980-04-23 |
Family
ID=27128297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79210710A DD141305A5 (de) | 1978-01-30 | 1979-01-30 | Verfahren zur herstellung von n-aethylaethylendiamin |
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 |
| SE446628B (sv) | 1986-09-29 |
| 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 |
| 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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