FR2459224A1 - Procede de preparation de n-alcoylethylenediamines - Google Patents
Procede de preparation de n-alcoylethylenediamines Download PDFInfo
- Publication number
- FR2459224A1 FR2459224A1 FR7919187A FR7919187A FR2459224A1 FR 2459224 A1 FR2459224 A1 FR 2459224A1 FR 7919187 A FR7919187 A FR 7919187A FR 7919187 A FR7919187 A FR 7919187A FR 2459224 A1 FR2459224 A1 FR 2459224A1
- Authority
- FR
- France
- Prior art keywords
- eda
- hydrocarbon solvent
- ethylenediamine
- reaction mixture
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 106
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 147
- 239000004215 Carbon black (E152) Substances 0.000 claims description 57
- 229930195733 hydrocarbon Natural products 0.000 claims description 57
- 150000002430 hydrocarbons Chemical class 0.000 claims description 56
- 239000002904 solvent Substances 0.000 claims description 51
- 239000011541 reaction mixture Substances 0.000 claims description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 36
- 150000001350 alkyl halides Chemical class 0.000 claims description 29
- 238000004508 fractional distillation Methods 0.000 claims description 27
- 239000012044 organic layer Substances 0.000 claims description 22
- 238000010533 azeotropic distillation Methods 0.000 claims description 20
- 238000004821 distillation Methods 0.000 claims description 20
- 239000010410 layer Substances 0.000 claims description 19
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 230000003113 alkalizing effect Effects 0.000 claims description 10
- 238000005804 alkylation reaction Methods 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 9
- 239000012452 mother liquor Substances 0.000 claims description 9
- 239000012071 phase Substances 0.000 claims description 9
- 239000000284 extract Substances 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- 239000002244 precipitate Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 4
- 150000001348 alkyl chlorides Chemical class 0.000 claims description 3
- -1 ammonium halide Chemical class 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 235000020094 liqueur Nutrition 0.000 claims description 3
- 235000010755 mineral Nutrition 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 229910001502 inorganic halide Inorganic materials 0.000 claims 3
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 239000002610 basifying agent Substances 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 230000021962 pH elevation Effects 0.000 claims 1
- 229930182555 Penicillin Natural products 0.000 abstract 2
- 150000002960 penicillins Chemical class 0.000 abstract 2
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- 229940124587 cephalosporin Drugs 0.000 abstract 1
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N cephalosporin C Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 abstract 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 11
- 229960003750 ethyl chloride Drugs 0.000 description 11
- 238000004064 recycling Methods 0.000 description 11
- 238000005194 fractionation Methods 0.000 description 10
- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000000926 separation method Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000003756 stirring Methods 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
- 239000007900 aqueous suspension Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 239000000706 filtrate Substances 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
- 239000006227 byproduct Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-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
- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
- 150000008045 alkali metal halides Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000003822 preparative gas chromatography Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- KDRUIMNNZBMLJR-UHFFFAOYSA-N 2-isopropylaminoethylamine Chemical compound CC(C)NCCN KDRUIMNNZBMLJR-UHFFFAOYSA-N 0.000 description 1
- BXSMMAVTEURRGG-UHFFFAOYSA-N 3-chlorohexane Chemical compound CCCC(Cl)CC BXSMMAVTEURRGG-UHFFFAOYSA-N 0.000 description 1
- 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- 125000005192 alkyl ethylene group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 235000013844 butane Nutrition 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000002171 ethylene diamines Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- DFPGBRPWDZFIPP-UHFFFAOYSA-N n'-butylethane-1,2-diamine Chemical compound CCCCNCCN DFPGBRPWDZFIPP-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000011369 resultant mixture 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/048,337 US4217308A (en) | 1978-01-30 | 1979-06-14 | Process for preparing N-alkylethylenediamines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2459224A1 true FR2459224A1 (fr) | 1981-01-09 |
| FR2459224B1 FR2459224B1 (enrdf_load_stackoverflow) | 1984-06-15 |
Family
ID=21954028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7919187A Granted FR2459224A1 (fr) | 1979-06-14 | 1979-07-25 | Procede de preparation de n-alcoylethylenediamines |
Country Status (10)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5001267A (en) * | 1987-12-21 | 1991-03-19 | Texaco Chemical Company | Secondary alkyl amine derivatives of ethylenediamine |
| RU2146244C1 (ru) * | 1998-07-07 | 2000-03-10 | Открытое акционерное общество "Синтез" | Способ получения ингибитора солевой коррозии |
| JP4532083B2 (ja) * | 2003-07-28 | 2010-08-25 | 東ソー株式会社 | Ｎ−モノアルキル置換アルキレンアミンの製造方法 |
| JP4731915B2 (ja) * | 2004-01-07 | 2011-07-27 | 大日本住友製薬株式会社 | メチルウレア化合物の製造方法 |
| WO2010042168A2 (en) * | 2008-10-06 | 2010-04-15 | Dow Global Technologies Inc. | Methods for making ethanolamine(s) and ethyleneamine(s) from ethylene oxide and ammonia, and related methods |
| CN116102429B (zh) * | 2022-12-27 | 2025-01-28 | 沈阳化工研究院有限公司 | 一种连续化合成n-乙基乙二胺的工艺方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2113208A1 (de) * | 1971-03-18 | 1972-09-28 | Goldschmidt Ag Th | Biocide Octylaminderivate |
| FR2415618A1 (fr) * | 1978-01-30 | 1979-08-24 | American Cyanamid Co | Procede de preparation de la n-ethylethylene-diamine par reaction de l'ethylene-diamine avec un halogenure d'ethyle |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1129160B (de) * | 1959-06-04 | 1962-05-10 | Basf Ag | Verfahren zur Trennung von AEthylendiamin und Wasser |
| DE1130814B (de) * | 1959-12-03 | 1962-06-07 | Basf Ag | Verfahren zur kontinuierlichen Entwaesserung von AEthylendiaminen |
| SE381867B (sv) * | 1973-03-07 | 1975-12-22 | Mo Och Domsjoe Ab | Sett att avlegsna vatten fran en blandning av etylendiamin och vatten |
| DE2455678C3 (de) * | 1974-11-25 | 1979-05-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Tetramethyläthylendiamin |
-
1979
- 1979-07-23 DE DE19792929841 patent/DE2929841A1/de active Granted
- 1979-07-25 FR FR7919187A patent/FR2459224A1/fr active Granted
- 1979-07-27 CA CA332,700A patent/CA1128070A/en not_active Expired
- 1979-07-27 NL NL7905836A patent/NL189039C/xx not_active IP Right Cessation
- 1979-07-27 CH CH699179A patent/CH649075A5/de not_active IP Right Cessation
- 1979-07-27 BE BE0/196503A patent/BE877951A/fr not_active IP Right Cessation
- 1979-07-27 GB GB7926360A patent/GB2051040B/en not_active Expired
- 1979-07-27 BR BR7904851A patent/BR7904851A/pt not_active IP Right Cessation
- 1979-08-08 IE IE145179A patent/IE48914B1/en not_active IP Right Cessation
-
1980
- 1980-06-13 JP JP7916380A patent/JPH0228588B2/ja not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2113208A1 (de) * | 1971-03-18 | 1972-09-28 | Goldschmidt Ag Th | Biocide Octylaminderivate |
| FR2415618A1 (fr) * | 1978-01-30 | 1979-08-24 | American Cyanamid Co | Procede de preparation de la n-ethylethylene-diamine par reaction de l'ethylene-diamine avec un halogenure d'ethyle |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/56 * |
Also Published As
| Publication number | Publication date |
|---|---|
| NL189039B (nl) | 1992-07-16 |
| GB2051040B (en) | 1983-10-12 |
| NL7905836A (nl) | 1980-12-16 |
| IE791451L (en) | 1980-12-14 |
| IE48914B1 (en) | 1985-06-12 |
| BE877951A (fr) | 1980-01-28 |
| DE2929841C2 (enrdf_load_stackoverflow) | 1989-11-09 |
| BR7904851A (pt) | 1981-01-27 |
| JPS5645442A (en) | 1981-04-25 |
| CH649075A5 (de) | 1985-04-30 |
| JPH0228588B2 (ja) | 1990-06-25 |
| CA1128070A (en) | 1982-07-20 |
| GB2051040A (en) | 1981-01-14 |
| FR2459224B1 (enrdf_load_stackoverflow) | 1984-06-15 |
| NL189039C (nl) | 1992-12-16 |
| DE2929841A1 (de) | 1980-12-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TP | Transmission of property |