NL7904648A - Werkwijze om bis-(n,n-dialkylamino)alkylethers te bereiden. - Google Patents
Werkwijze om bis-(n,n-dialkylamino)alkylethers te bereiden. Download PDFInfo
- Publication number
- NL7904648A NL7904648A NL7904648A NL7904648A NL7904648A NL 7904648 A NL7904648 A NL 7904648A NL 7904648 A NL7904648 A NL 7904648A NL 7904648 A NL7904648 A NL 7904648A NL 7904648 A NL7904648 A NL 7904648A
- Authority
- NL
- Netherlands
- Prior art keywords
- sodium
- bis
- dimethylamino
- formula
- ether
- Prior art date
Links
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 41
- 150000005215 alkyl ethers Chemical class 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000011734 sodium Substances 0.000 claims description 55
- 229910052708 sodium Inorganic materials 0.000 claims description 54
- 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 claims description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 41
- 239000003085 diluting agent Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 32
- -1 sodium alkoxide Chemical class 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 150000002170 ethers Chemical class 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 229910052700 potassium Inorganic materials 0.000 claims description 13
- 239000011591 potassium Substances 0.000 claims description 13
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 229960002887 deanol Drugs 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 239000012972 dimethylethanolamine Substances 0.000 claims description 6
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000011496 polyurethane foam Substances 0.000 claims description 5
- 238000011084 recovery Methods 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- YSKPDPSMMRKCND-UHFFFAOYSA-N sodium;2-(dimethylamino)ethanolate Chemical compound [Na+].CN(C)CC[O-] YSKPDPSMMRKCND-UHFFFAOYSA-N 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- WYVFVMUROJPJSS-UHFFFAOYSA-N [2-(dimethylamino)ethoxy]sulfonic acid Chemical compound CN(C)CCOS(O)(=O)=O WYVFVMUROJPJSS-UHFFFAOYSA-N 0.000 claims 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 3
- 101100162210 Aspergillus parasiticus (strain ATCC 56775 / NRRL 5862 / SRRC 143 / SU-1) aflM gene Proteins 0.000 claims 1
- 101100102500 Caenorhabditis elegans ver-1 gene Proteins 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims 1
- 229910000105 potassium hydride Inorganic materials 0.000 claims 1
- NVIIFFZOTKEMRZ-UHFFFAOYSA-N potassium;2-(dimethylamino)ethanolate Chemical compound [K+].CN(C)CC[O-] NVIIFFZOTKEMRZ-UHFFFAOYSA-N 0.000 claims 1
- KLAQPPQAGBYNMU-UHFFFAOYSA-M potassium;2-(dimethylamino)ethyl sulfate Chemical compound [K+].CN(C)CCOS([O-])(=O)=O KLAQPPQAGBYNMU-UHFFFAOYSA-M 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- ZEQWRUGWKKGOAW-UHFFFAOYSA-N sodium;1-(dimethylamino)ethanolate Chemical compound [Na+].CC([O-])N(C)C ZEQWRUGWKKGOAW-UHFFFAOYSA-N 0.000 claims 1
- DERHCNHUULQWAW-UHFFFAOYSA-M sodium;2-(dimethylamino)ethyl sulfate Chemical compound [Na+].CN(C)CCOS([O-])(=O)=O DERHCNHUULQWAW-UHFFFAOYSA-M 0.000 claims 1
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 claims 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 54
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 238000009835 boiling Methods 0.000 description 14
- 239000007789 gas Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 150000004703 alkoxides Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 0 C(CC1)CC*11CCCCC1 Chemical compound C(CC1)CC*11CCCCC1 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- 241001274216 Naso Species 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000006959 Williamson synthesis reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical class [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007373 indentation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2565979A | 1979-03-30 | 1979-03-30 | |
| US2565979 | 1979-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL7904648A true NL7904648A (nl) | 1980-10-02 |
Family
ID=21827342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL7904648A NL7904648A (nl) | 1979-03-30 | 1979-06-13 | Werkwijze om bis-(n,n-dialkylamino)alkylethers te bereiden. |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS55130943A (de) |
| DE (1) | DE2921972A1 (de) |
| FR (1) | FR2452477A1 (de) |
| GB (1) | GB2045237B (de) |
| IT (1) | IT1196398B (de) |
| NL (1) | NL7904648A (de) |
| SE (2) | SE448538B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE3504242A1 (de) * | 1985-02-08 | 1986-08-14 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von tertiaeren etheraminen |
| US5268470A (en) * | 1991-07-12 | 1993-12-07 | Buckman Laboratories Internation, Inc. | Diamine compounds, method of making same, method of use of same and intermediates |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3397238A (en) * | 1965-11-16 | 1968-08-13 | Pfizer & Co C | Process for the preparation of alkyl ethers of amino-alcohols |
| GB2010839B (en) * | 1977-12-27 | 1982-05-12 | Union Carbide Corp | Process for producing bis-(n,n-dialkylamino) alkyl ethers |
-
1979
- 1979-05-25 SE SE7904581A patent/SE448538B/sv not_active IP Right Cessation
- 1979-05-30 DE DE19792921972 patent/DE2921972A1/de not_active Ceased
- 1979-06-13 NL NL7904648A patent/NL7904648A/nl unknown
- 1979-06-22 GB GB7921782A patent/GB2045237B/en not_active Expired
- 1979-06-27 JP JP8028479A patent/JPS55130943A/ja active Granted
- 1979-07-04 IT IT24113/79A patent/IT1196398B/it active
- 1979-10-04 FR FR7924722A patent/FR2452477A1/fr active Granted
-
1986
- 1986-11-05 SE SE8604745A patent/SE463367B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2452477A1 (fr) | 1980-10-24 |
| FR2452477B1 (de) | 1984-10-19 |
| SE7904581L (sv) | 1980-10-01 |
| SE448538B (sv) | 1987-03-02 |
| SE447375B (sv) | 1986-11-10 |
| SE8604745D0 (sv) | 1986-11-05 |
| GB2045237A (en) | 1980-10-29 |
| GB2045237B (en) | 1983-06-15 |
| SE463367B (sv) | 1990-11-12 |
| IT7924113A0 (it) | 1979-07-04 |
| JPS55130943A (en) | 1980-10-11 |
| IT1196398B (it) | 1988-11-16 |
| JPS5755709B2 (de) | 1982-11-25 |
| SE8604745L (sv) | 1986-11-05 |
| DE2921972A1 (de) | 1980-10-02 |
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