CA1120059A - Process for preparing n-ethylethylenediamine - Google Patents
Process for preparing n-ethylethylenediamineInfo
- Publication number
- CA1120059A CA1120059A CA000318858A CA318858A CA1120059A CA 1120059 A CA1120059 A CA 1120059A CA 000318858 A CA000318858 A CA 000318858A CA 318858 A CA318858 A CA 318858A CA 1120059 A CA1120059 A CA 1120059A
- Authority
- CA
- Canada
- Prior art keywords
- eda
- weight
- reaction mixture
- heptane
- process according
- 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
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 79
- -1 ethyl halide Chemical class 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 24
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 134
- 239000002904 solvent Substances 0.000 claims description 46
- 239000011541 reaction mixture Substances 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 40
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 31
- 239000012044 organic layer Substances 0.000 claims description 24
- 239000010410 layer Substances 0.000 claims description 21
- 239000004215 Carbon black (E152) Substances 0.000 claims description 20
- 229930195733 hydrocarbon Natural products 0.000 claims description 20
- 150000002430 hydrocarbons Chemical class 0.000 claims description 20
- 238000004821 distillation Methods 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 12
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 12
- 230000003113 alkalizing effect Effects 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 10
- 239000012452 mother liquor Substances 0.000 claims description 9
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 8
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 8
- 238000005804 alkylation reaction Methods 0.000 claims description 7
- 239000002244 precipitate Substances 0.000 claims description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 6
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 5
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000284 extract Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 238000004508 fractional distillation Methods 0.000 claims description 4
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 230000002730 additional effect Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 238000011084 recovery Methods 0.000 abstract description 2
- IVBHGBMCVLDMKU-GXNBUGAJSA-N piperacillin Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 IVBHGBMCVLDMKU-GXNBUGAJSA-N 0.000 abstract 2
- 229960002292 piperacillin Drugs 0.000 abstract 2
- 229930182555 Penicillin Natural products 0.000 abstract 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 229940012017 ethylenediamine Drugs 0.000 description 20
- 239000012071 phase Substances 0.000 description 15
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 13
- 229960003750 ethyl chloride Drugs 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000003822 preparative gas chromatography Methods 0.000 description 6
- 238000005194 fractionation Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-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
- 238000009835 boiling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- XPYQFIISZQCINN-QVXDJYSKSA-N 4-amino-1-[(2r,3e,4s,5r)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrate Chemical compound O.O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 XPYQFIISZQCINN-QVXDJYSKSA-N 0.000 description 2
- 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 2
- 230000029936 alkylation Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 150000002171 ethylene diamines Chemical class 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 229940093932 potassium hydroxide Drugs 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- GRYSXUXXBDSYRT-WOUKDFQISA-N (2r,3r,4r,5r)-2-(hydroxymethyl)-4-methoxy-5-[6-(methylamino)purin-9-yl]oxolan-3-ol Chemical compound C1=NC=2C(NC)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1OC GRYSXUXXBDSYRT-WOUKDFQISA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 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
- 238000007865 diluting Methods 0.000 description 1
- 125000003916 ethylene diamine group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005843 halogen group Chemical group 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
- HDCAZTXEZQWTIJ-UHFFFAOYSA-N n,n',n'-triethylethane-1,2-diamine Chemical compound CCNCCN(CC)CC HDCAZTXEZQWTIJ-UHFFFAOYSA-N 0.000 description 1
- DIHKMUNUGQVFES-UHFFFAOYSA-N n,n,n',n'-tetraethylethane-1,2-diamine Chemical compound CCN(CC)CCN(CC)CC DIHKMUNUGQVFES-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87345078A | 1978-01-30 | 1978-01-30 | |
| US873,450 | 1978-01-30 | ||
| US96097278A | 1978-11-15 | 1978-11-15 | |
| US960,972 | 1992-10-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1120059A true CA1120059A (en) | 1982-03-16 |
Family
ID=27128297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000318858A Expired CA1120059A (en) | 1978-01-30 | 1978-12-29 | Process for preparing n-ethylethylenediamine |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102260175A (zh) * | 2011-06-08 | 2011-11-30 | 浙江大学 | N-乙基乙二胺的合成方法 |
Families Citing this family (4)
| 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 |
| 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
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102260175A (zh) * | 2011-06-08 | 2011-11-30 | 浙江大学 | N-乙基乙二胺的合成方法 |
| CN102260175B (zh) * | 2011-06-08 | 2013-11-20 | 浙江大学 | N-乙基乙二胺的合成方法 |
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 |
| 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 |
| 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 |
|---|---|---|---|
| MKEX | Expiry |