DE2900060C2 - - Google Patents
Info
- Publication number
- DE2900060C2 DE2900060C2 DE2900060A DE2900060A DE2900060C2 DE 2900060 C2 DE2900060 C2 DE 2900060C2 DE 2900060 A DE2900060 A DE 2900060A DE 2900060 A DE2900060 A DE 2900060A DE 2900060 C2 DE2900060 C2 DE 2900060C2
- Authority
- DE
- Germany
- Prior art keywords
- eda
- reaction mixture
- heptane
- need
- ethyl
- 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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 120
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 77
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 claims description 48
- 239000011541 reaction mixture Substances 0.000 claims description 43
- 239000002904 solvent Substances 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 31
- 239000007788 liquid Substances 0.000 claims description 26
- -1 ethyl halide Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 19
- 239000010410 layer Substances 0.000 claims description 18
- 239000012044 organic layer Substances 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 12
- 230000003113 alkalizing effect Effects 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 12
- 238000004508 fractional distillation Methods 0.000 claims description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 8
- 238000005804 alkylation reaction Methods 0.000 claims description 8
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- 239000002244 precipitate Substances 0.000 claims description 7
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 claims 1
- 150000008045 alkali metal halides Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 24
- 239000012071 phase Substances 0.000 description 16
- 239000004215 Carbon black (E152) Substances 0.000 description 13
- 229930195733 hydrocarbon Natural products 0.000 description 13
- 150000002430 hydrocarbons Chemical class 0.000 description 13
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 12
- 229960003750 ethyl chloride Drugs 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- 238000000926 separation method Methods 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 239000012452 mother liquor Substances 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
- 238000005194 fractionation Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- IWOVMFQVZYDIKE-UHFFFAOYSA-N [Pb].CCCCCCC Chemical compound [Pb].CCCCCCC IWOVMFQVZYDIKE-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 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
- 239000011521 glass Substances 0.000 description 2
- 238000004064 recycling 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
- 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
- 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
- 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
- 238000004886 process control Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000007704 transition Effects 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 |
|---|---|
| DE2900060A1 DE2900060A1 (de) | 1979-08-09 |
| DE2900060C2 true DE2900060C2 (en, 2012) | 1988-01-21 |
Family
ID=27128297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792900060 Granted DE2900060A1 (de) | 1978-01-30 | 1979-01-02 | 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 |
| 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 |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: LEDERLE PIPERACILLIN, INC., CAROLINA, PUERTO RICO, |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| V448 | Application of spc |
Free format text: PRODUCT NAME: PIPERACILLIN/FLUCLOXACILLIN; REGISTRATION NO/DATE: 6402.00.00, 6402.01.00, 6402.02.00, 6402.03.00; 19890705 Spc suppl protection certif: 193 75 104 Filing date: 19930702 |
|
| V472 | Application for supplementary protection certificate rejected |
Free format text: PRODUCT NAME: PIPERACILLIN/FLUCLOXACILLIN; REGISTRATION NO/DATE: 6402.00.00, 6402.01.00, 6402.02.00, 6402.03.00; 19890705 Spc suppl protection certif: 193 75 104 Filing date: 19930702 |