DE1643555C3 - dimethyl-amino)-alkyl] -äthern - Google Patents
dimethyl-amino)-alkyl] -äthernInfo
- Publication number
- DE1643555C3 DE1643555C3 DE1643555A DEU0014267A DE1643555C3 DE 1643555 C3 DE1643555 C3 DE 1643555C3 DE 1643555 A DE1643555 A DE 1643555A DE U0014267 A DEU0014267 A DE U0014267A DE 1643555 C3 DE1643555 C3 DE 1643555C3
- Authority
- DE
- Germany
- Prior art keywords
- bis
- ether
- dimethylamino
- alkyl
- amine
- 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
- 150000002170 ethers Chemical class 0.000 title claims description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 title 1
- -1 N, N-dimethylamino Chemical group 0.000 claims description 32
- 150000001412 amines Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 230000017858 demethylation Effects 0.000 claims description 2
- 238000010520 demethylation reaction Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 10
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical class CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 150000003141 primary amines Chemical class 0.000 description 6
- 150000003512 tertiary amines Chemical class 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012380 dealkylating agent Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- AQGNVWRYTKPRMR-UHFFFAOYSA-N n'-[2-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCNCCN AQGNVWRYTKPRMR-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- CURCMGVZNYCRNY-UHFFFAOYSA-N trimethylazanium;iodide Chemical group I.CN(C)C CURCMGVZNYCRNY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1833—Catalysts containing secondary or tertiary amines or salts thereof having ether, acetal, or orthoester groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB44164/67A GB1154418A (en) | 1967-09-28 | 1967-09-28 | Preparation of Amine Ethers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1643555A1 DE1643555A1 (de) | 1972-03-16 |
| DE1643555B2 DE1643555B2 (de) | 1977-11-03 |
| DE1643555C3 true DE1643555C3 (de) | 1978-06-22 |
Family
ID=10432076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1643555A Expired DE1643555C3 (de) | 1967-09-28 | 1967-09-28 | dimethyl-amino)-alkyl] -äthern |
Country Status (5)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1117552A (en) * | 1977-12-27 | 1982-02-02 | Fedor Poppelsdorf | Process for producing bis(n,n-dialkylamino) alkyl ethers |
| DE3362615D1 (en) * | 1982-09-27 | 1986-04-24 | Toyo Soda Mfg Co Ltd | Method for producing bis(beta-(n,n-dimethylamino)alkyl)ether |
| JPS5970650A (ja) * | 1982-10-18 | 1984-04-21 | Toyo Soda Mfg Co Ltd | ビス〔β−（Ｎ，Ｎ−ジメチルアミノ）エチル〕エ−テルの製造法 |
| US4474988A (en) * | 1982-12-27 | 1984-10-02 | Union Carbide Corporation | Process for the production of bis-(N,N,-dialkylamino)alkyl ether |
| JPS59186943A (ja) * | 1983-04-07 | 1984-10-23 | Toyo Soda Mfg Co Ltd | ビス〔β−（Ｎ，Ｎ−ジメチルアミノ）エチル〕エ−テルの製造法 |
| US4504279A (en) * | 1984-07-09 | 1985-03-12 | Texaco Inc | Corrosion inhibited motor fuel |
| US5214142A (en) * | 1990-09-20 | 1993-05-25 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for the preparation of aminoethers |
| DE10055497A1 (de) | 2000-11-09 | 2002-05-29 | Bayer Ag | Modifizierungsmittel für die anionische Polymerisation |
| US8507704B2 (en) * | 2009-09-08 | 2013-08-13 | Air Products And Chemicals, Inc. | Liquid composition containing aminoether for deposition of metal-containing films |
| CN102452946B (zh) * | 2010-10-25 | 2014-07-30 | 中国石油化工股份有限公司 | 一种双(2-二甲氨基乙基)醚的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1919301A (en) * | 1930-07-25 | 1933-07-25 | Harold A Morton | Age resisting vulcanized rubber and antioxidant agent |
-
1966
- 1966-08-17 US US572918A patent/US3426072A/en not_active Expired - Lifetime
-
1967
- 1967-09-28 DE DE1643555A patent/DE1643555C3/de not_active Expired
- 1967-09-28 GB GB44164/67A patent/GB1154418A/en not_active Expired
- 1967-10-10 NL NL676713737A patent/NL145219B/xx not_active IP Right Cessation
- 1967-10-11 BE BE704945D patent/BE704945A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE1643555B2 (de) | 1977-11-03 |
| US3426072A (en) | 1969-02-04 |
| GB1154418A (en) | 1969-06-11 |
| BE704945A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-04-11 |
| DE1643555A1 (de) | 1972-03-16 |
| NL145219B (nl) | 1975-03-17 |
| NL6713737A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-04-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: UNION CARBIDE CORP., 06817 DANBURY, CONN., US |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: DANNENBERG, G., DIPL.-ING., 6000 FRANKFURT SCHMIED-KOWARZIK, V., DR. WEINHOLD, P., DIPL.-CHEM. DR.,PAT.-ANW., 8000 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |