JPS6128658B2 - - Google Patents
Info
- Publication number
- JPS6128658B2 JPS6128658B2 JP6007783A JP6007783A JPS6128658B2 JP S6128658 B2 JPS6128658 B2 JP S6128658B2 JP 6007783 A JP6007783 A JP 6007783A JP 6007783 A JP6007783 A JP 6007783A JP S6128658 B2 JPS6128658 B2 JP S6128658B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- ether
- aliphatic amine
- amine
- dimethylamino
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 67
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 45
- 238000009835 boiling Methods 0.000 claims description 22
- 238000004821 distillation Methods 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 20
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 claims description 18
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 3
- QVYARBLCAHCSFJ-UHFFFAOYSA-N butane-1,1-diamine Chemical compound CCCC(N)N QVYARBLCAHCSFJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006308 propyl amino group Chemical group 0.000 claims 1
- -1 ether amine Chemical class 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 238000000034 method Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- 239000002994 raw material Substances 0.000 description 10
- 239000012649 demethylating agent Substances 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 239000006228 supernatant Substances 0.000 description 8
- 238000006386 neutralization reaction Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000007790 solid phase Substances 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000010520 demethylation reaction Methods 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000010612 desalination reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- UOULCEYHQNCFFH-UHFFFAOYSA-M sodium;hydroxymethanesulfonate Chemical compound [Na+].OCS([O-])(=O)=O UOULCEYHQNCFFH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6007783A JPS59186944A (ja) | 1983-04-07 | 1983-04-07 | ビス〔β−（Ｎ，Ｎ−ジメチルアミノ）エチル〕エ−テルの製造方法 |
| DE8383109583T DE3362615D1 (en) | 1982-09-27 | 1983-09-26 | Method for producing bis(beta-(n,n-dimethylamino)alkyl)ether |
| EP83109583A EP0104641B1 (en) | 1982-09-27 | 1983-09-26 | Method for producing bis(beta-(n,n-dimethylamino)alkyl)ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6007783A JPS59186944A (ja) | 1983-04-07 | 1983-04-07 | ビス〔β−（Ｎ，Ｎ−ジメチルアミノ）エチル〕エ−テルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59186944A JPS59186944A (ja) | 1984-10-23 |
| JPS6128658B2 true JPS6128658B2 (pt) | 1986-07-01 |
Family
ID=13131659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6007783A Granted JPS59186944A (ja) | 1982-09-27 | 1983-04-07 | ビス〔β−（Ｎ，Ｎ−ジメチルアミノ）エチル〕エ−テルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59186944A (pt) |
-
1983
- 1983-04-07 JP JP6007783A patent/JPS59186944A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59186944A (ja) | 1984-10-23 |
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