HU182922B - Process for preparing n-ethyl-ethylene-diamine - Google Patents
Process for preparing n-ethyl-ethylene-diamine Download PDFInfo
- Publication number
- HU182922B HU182922B HU79AE556A HUAE000556A HU182922B HU 182922 B HU182922 B HU 182922B HU 79AE556 A HU79AE556 A HU 79AE556A HU AE000556 A HUAE000556 A HU AE000556A HU 182922 B HU182922 B HU 182922B
- Authority
- HU
- Hungary
- Prior art keywords
- weight
- ethylenediamine
- hydrocarbon solvent
- reaction mixture
- ethyl
- Prior art date
Links
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000004519 manufacturing process Methods 0.000 title 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 76
- 239000011541 reaction mixture Substances 0.000 claims abstract description 47
- 239000002904 solvent Substances 0.000 claims abstract description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 31
- -1 ethyl halide Chemical class 0.000 claims abstract description 29
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 17
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 17
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 239000012452 mother liquor Substances 0.000 claims abstract description 11
- 238000005406 washing Methods 0.000 claims abstract description 11
- 239000003513 alkali Substances 0.000 claims abstract description 10
- 150000004820 halides Chemical class 0.000 claims abstract description 9
- 239000002244 precipitate Substances 0.000 claims abstract description 8
- 239000002002 slurry Substances 0.000 claims abstract description 7
- 230000003472 neutralizing effect Effects 0.000 claims abstract 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 127
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 40
- 238000010533 azeotropic distillation Methods 0.000 claims description 24
- 239000012074 organic phase Substances 0.000 claims description 20
- 239000008346 aqueous phase Substances 0.000 claims description 16
- 238000004821 distillation Methods 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000000284 extract Substances 0.000 claims description 5
- 238000004508 fractional distillation Methods 0.000 claims description 4
- 238000005194 fractionation Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- 229940012017 ethylenediamine Drugs 0.000 claims 5
- 150000004985 diamines Chemical class 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 abstract description 6
- 238000005804 alkylation reaction Methods 0.000 abstract description 5
- 239000012044 organic layer Substances 0.000 abstract 3
- 230000003113 alkalizing effect Effects 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 239000010410 layer Substances 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 11
- 229960003750 ethyl chloride Drugs 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 238000000926 separation method Methods 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000012455 biphasic mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000002051 biphasic effect Effects 0.000 description 5
- 239000000047 product Substances 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
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 3
- 229940081974 saccharin Drugs 0.000 description 3
- 235000019204 saccharin Nutrition 0.000 description 3
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YYOJQGJHQWBTCW-UHFFFAOYSA-N 2-(ethylsulfamoyl)benzoic acid Chemical compound CCNS(=O)(=O)C1=CC=CC=C1C(O)=O YYOJQGJHQWBTCW-UHFFFAOYSA-N 0.000 description 1
- IZQAUUVBKYXMET-UHFFFAOYSA-N 2-bromoethanamine Chemical compound NCCBr IZQAUUVBKYXMET-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- QLHFEAUVHPDXSC-UHFFFAOYSA-N Cl.Cl.CCNCCN Chemical compound Cl.Cl.CCNCCN QLHFEAUVHPDXSC-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- XZUAPPXGIFNDRA-UHFFFAOYSA-N ethane-1,2-diamine;hydrate Chemical compound O.NCCN XZUAPPXGIFNDRA-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 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
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction 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 |
|---|---|
| HU182922B true HU182922B (en) | 1984-03-28 |
Family
ID=27128297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79AE556A HU182922B (en) | 1978-01-30 | 1979-01-26 | Process for preparing n-ethyl-ethylene-diamine |
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 |
| 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 |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee | ||
| HRH9 | Withdrawal of annulment decision |