CA1228368A - Process for preparing secondary aminoether alcohols - Google Patents
Process for preparing secondary aminoether alcoholsInfo
- Publication number
- CA1228368A CA1228368A CA000465354A CA465354A CA1228368A CA 1228368 A CA1228368 A CA 1228368A CA 000465354 A CA000465354 A CA 000465354A CA 465354 A CA465354 A CA 465354A CA 1228368 A CA1228368 A CA 1228368A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- ranging
- psig
- carried out
- reaction
- 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
- -1 aminoether alcohols Chemical group 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 69
- 238000000034 method Methods 0.000 claims abstract description 43
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 39
- 230000008569 process Effects 0.000 claims abstract description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 28
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims description 41
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- 229910052759 nickel Inorganic materials 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- VDGMIGHRDCJLMN-UHFFFAOYSA-N [Cu].[Co].[Ni] Chemical compound [Cu].[Co].[Ni] VDGMIGHRDCJLMN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000036647 reaction Effects 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical group NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 claims 1
- 238000005201 scrubbing Methods 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 41
- AHXXIYFEJGGBMG-UHFFFAOYSA-N 1-[2-(tert-butylamino)ethoxy]ethanol Chemical compound CC(O)OCCNC(C)(C)C AHXXIYFEJGGBMG-UHFFFAOYSA-N 0.000 description 24
- 238000003475 lamination Methods 0.000 description 24
- 239000000376 reactant Substances 0.000 description 23
- 239000006227 byproduct Substances 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 8
- 230000004913 activation Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 235000009434 Actinidia chinensis Nutrition 0.000 description 5
- 235000009436 Actinidia deliciosa Nutrition 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 229920000180 alkyd Polymers 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 5
- 244000298697 Actinidia deliciosa Species 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910002804 graphite Inorganic materials 0.000 description 4
- 239000010439 graphite Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- OILJIEKQCVHNMM-UHFFFAOYSA-N 4-tert-butylmorpholine Chemical compound CC(C)(C)N1CCOCC1 OILJIEKQCVHNMM-UHFFFAOYSA-N 0.000 description 3
- 206010039509 Scab Diseases 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000201776 Steno Species 0.000 description 2
- 208000010513 Stupor Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052593 corundum Inorganic materials 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910001504 inorganic chloride Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910001845 yogo sapphire Inorganic materials 0.000 description 2
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
- JVKRKMWZYMKVTQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JVKRKMWZYMKVTQ-UHFFFAOYSA-N 0.000 description 1
- LMRKVKPRHROQRR-UHFFFAOYSA-N 4-butylmorpholine Chemical compound CCCCN1CCOCC1 LMRKVKPRHROQRR-UHFFFAOYSA-N 0.000 description 1
- 244000298715 Actinidia chinensis Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910020637 Co-Cu Inorganic materials 0.000 description 1
- 229910017816 Cu—Co Inorganic materials 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- QXZUUHYBWMWJHK-UHFFFAOYSA-N [Co].[Ni] Chemical compound [Co].[Ni] QXZUUHYBWMWJHK-UHFFFAOYSA-N 0.000 description 1
- GXDVEXJTVGRLNW-UHFFFAOYSA-N [Cr].[Cu] Chemical compound [Cr].[Cu] GXDVEXJTVGRLNW-UHFFFAOYSA-N 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVZZPLDJERFENQ-NKTUOASPSA-N bassianolide Chemical compound CC(C)C[C@@H]1N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C(C)C)OC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C(C)C)OC1=O QVZZPLDJERFENQ-NKTUOASPSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical compound [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 239000002241 glass-ceramic Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/565,097 US4487967A (en) | 1983-12-23 | 1983-12-23 | Process for preparing secondary aminoether alcohols |
| US565,097 | 1983-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1228368A true CA1228368A (en) | 1987-10-20 |
Family
ID=24257203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000465354A Expired CA1228368A (en) | 1983-12-23 | 1984-10-12 | Process for preparing secondary aminoether alcohols |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4487967A (forum.php) |
| EP (1) | EP0147990B1 (forum.php) |
| JP (1) | JPS60169450A (forum.php) |
| AR (1) | AR241489A1 (forum.php) |
| AU (1) | AU568708B2 (forum.php) |
| BR (1) | BR8406684A (forum.php) |
| CA (1) | CA1228368A (forum.php) |
| DE (1) | DE3472248D1 (forum.php) |
| MX (1) | MX7317E (forum.php) |
| NO (1) | NO160362C (forum.php) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1229091A (en) * | 1983-12-23 | 1987-11-10 | Win-Sow W. Ho | Process for preparing tertiary polyalkenyl aminoether alcohols |
| US4665195A (en) * | 1983-12-23 | 1987-05-12 | Exxon Research And Engineering Company | Process for preparing di-amino-polyalkenyl ethers |
| US4487967A (en) * | 1983-12-23 | 1984-12-11 | Exxon Research & Engineering Co. | Process for preparing secondary aminoether alcohols |
| US4745190A (en) * | 1984-07-25 | 1988-05-17 | Air Products And Chemicals, Inc. | Selective synthesis of substituted amines |
| US4680393A (en) * | 1986-05-08 | 1987-07-14 | Air Products And Chamicals, Inc. | Process for the selective synthesis of tertiary alkanolamines |
| US4855425A (en) * | 1986-08-27 | 1989-08-08 | Air Products And Chemicals, Inc. | Process for the selective synthesis of ethylene diamines |
| DE3724239A1 (de) * | 1987-07-22 | 1989-02-02 | Basf Ag | Verfahren zur herstellung von aliphatischen n,n-dialkylsubstituierten aminoalkoholen |
| US4894178A (en) * | 1987-10-13 | 1990-01-16 | Exxon Research And Engineering Company | Absorbent composition containing severely-hindered amine mixture for the absorption of H2 S |
| US4895670A (en) * | 1987-10-13 | 1990-01-23 | Exxon Research And Engineering Company | Addition of severely-hindered aminoacids to severely-hindered amines for the absorption of H2 S |
| US4894179A (en) * | 1987-10-13 | 1990-01-16 | Exxon Research And Engineering Company | Absorbent composition containing a tertiary amino azabicyclic alcohol and an amine salt |
| US4892674A (en) * | 1987-10-13 | 1990-01-09 | Exxon Research And Engineering Company | Addition of severely-hindered amine salts and/or aminoacids to non-hindered amine solutions for the absorption of H2 S |
| BR8901452A (pt) * | 1988-03-31 | 1989-11-14 | Union Carbide Corp | Processo para preparar n-(polioxialquil)-n-(alquil)aminas |
| JPH0650138B2 (ja) * | 1988-12-22 | 1994-06-29 | いすゞ自動車株式会社 | 車両用歯車変速機 |
| US7442840B2 (en) * | 2004-02-17 | 2008-10-28 | Exxonmobil Research And Engineering Company | Synthesis of severely sterically hindered amino-ether alcohols and diaminopolyalkenyl ethers using a high activity powder catalyst |
| WO2005082836A1 (en) * | 2004-02-17 | 2005-09-09 | Exxonmobil Research And Engineering Company | Synthesis of severely sterically hindered secondary aminoether alcohols from a ketene and/or carboxylic acid halide and/or carboxylic acid anhydride |
| KR101143065B1 (ko) * | 2004-02-17 | 2012-05-08 | 엑손모빌 리서치 앤드 엔지니어링 컴퍼니 | 입체 장애 2급 아미노에터 알콜의 합성 방법 |
| CA2556766C (en) * | 2004-02-17 | 2012-10-23 | Exxonmobil Research And Engineering Company | Synthesis of sterically hindered secondary aminoether alcohols |
| KR101162160B1 (ko) * | 2004-02-17 | 2012-07-05 | 엑손모빌 리서치 앤드 엔지니어링 컴퍼니 | 산 무수물 및/또는 산 할로겐화물 및 삼산화 황으로부터입체 장애 2급 아미노에터 알콜을 합성하는 방법 |
| WO2005082834A1 (en) | 2004-02-17 | 2005-09-09 | Exxonmobil Research And Engineering Company | Catalytic preparation of severely sterically hindered amino-ether alcohols using a metal loaded catalyst |
| DE102005029932A1 (de) * | 2005-06-28 | 2007-01-11 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur Herstellung von Polyetheraminen |
| JP5271708B2 (ja) | 2005-08-09 | 2013-08-21 | エクソンモービル リサーチ アンド エンジニアリング カンパニー | 酸性ガス洗浄プロセスのためのアルキルアミノアルキルオキシ（アルコール）モノアルキルエーテル |
| CA2617610C (en) * | 2005-08-09 | 2013-04-02 | Exxonmobil Research And Engineering Company | Polyalkyleneacrylamide salt for acid gas scrubbing process |
| EP2099738B1 (de) * | 2006-12-06 | 2017-02-01 | Clariant International Ltd | Verfahren zur herstellung von polyetheraminen |
| US8524184B2 (en) * | 2009-07-08 | 2013-09-03 | Exxonmobil Research And Engineering Company | Sulfur recovery plant tail gas treatment process |
| CN102884039B (zh) * | 2010-04-07 | 2014-11-26 | 巴斯夫欧洲公司 | 在气相中制备不对称叔丁基仲胺的方法 |
| CA2798971C (en) * | 2010-05-21 | 2018-07-24 | Basf Se | Process for preparing 2-(2-tert-butylaminoethoxy)ethanol (tert-butylaminodiglycol, tbadg) |
| US8455693B2 (en) | 2010-05-21 | 2013-06-04 | Basf Se | Process for preparing 2-(2-tert-butylaminoethoxy)ethanol (tert-butylaminodiglycol, TBADG) |
| CA3153809A1 (en) | 2019-09-10 | 2021-03-18 | Basf Se | Process for removal of acid gases from a fluid stream |
| CN119330841B (zh) * | 2024-11-11 | 2025-06-03 | 山东达民化工股份有限公司 | 催化合成叔丁胺基乙氧基乙醇的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2355337A (en) * | 1942-08-28 | 1944-08-08 | Rohm & Haas | Preparation of ether amines |
| US2928877A (en) * | 1957-05-10 | 1960-03-15 | Wyandotte Chemicals Corp | Process for preparing oxyalkyleneamines |
| US3070552A (en) * | 1957-06-17 | 1962-12-25 | Onyx Oil & Chemical Company | Polyamines |
| GB1287181A (en) * | 1969-03-03 | 1972-08-31 | Jefferson Chem Co Inc | Tertiary polyoxyalkylenepolyamines |
| US3708539A (en) * | 1970-02-06 | 1973-01-02 | Union Oil Co | Condensation of ammonia or a primary or secondary amine with an alcohol |
| US3708534A (en) * | 1970-03-19 | 1973-01-02 | Teijin Ltd | Process for the preparation of omega-hydroxy saturated aliphatic monocarboxylic acids of 4 to 12 carbon atoms |
| US3654370A (en) * | 1970-08-28 | 1972-04-04 | Jefferson Chem Co Inc | Process for preparing polyoxyalkylene polyamines |
| US3660319A (en) * | 1970-12-08 | 1972-05-02 | Jefferson Chem Co Inc | Tertiary polyoxyalkylenepolyamines |
| GB1530570A (en) * | 1977-09-30 | 1978-11-01 | Texaco Development Corp | Process for the simultaneous production of 2-(2-aminoalkoxy)alkanol and morpholine |
| DE2824908A1 (de) * | 1978-06-07 | 1979-12-20 | Basf Ag | Verfahren zur herstellung von omega, omega'-bis-dialkylaminoalkanen |
| DE3362219D1 (en) * | 1982-01-18 | 1986-04-03 | Exxon Research Engineering Co | A process for the removal of h2s from gaseous mixtures using diaminoethers |
| EP0084943B2 (en) * | 1982-01-18 | 1989-08-02 | Exxon Research And Engineering Company | Secondary and tertiary amino alcohols |
| US4487967A (en) * | 1983-12-23 | 1984-12-11 | Exxon Research & Engineering Co. | Process for preparing secondary aminoether alcohols |
-
1983
- 1983-12-23 US US06/565,097 patent/US4487967A/en not_active Expired - Fee Related
-
1984
- 1984-10-12 CA CA000465354A patent/CA1228368A/en not_active Expired
- 1984-10-23 AR AR84298345A patent/AR241489A1/es active
- 1984-11-05 NO NO844388A patent/NO160362C/no unknown
- 1984-11-23 MX MX8411367U patent/MX7317E/es unknown
- 1984-12-17 EP EP84308791A patent/EP0147990B1/en not_active Expired
- 1984-12-17 DE DE8484308791T patent/DE3472248D1/de not_active Expired
- 1984-12-21 BR BR8406684A patent/BR8406684A/pt not_active IP Right Cessation
- 1984-12-21 JP JP59270550A patent/JPS60169450A/ja active Granted
- 1984-12-21 AU AU37096/84A patent/AU568708B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| NO844388L (no) | 1985-06-24 |
| EP0147990B1 (en) | 1988-06-22 |
| US4487967A (en) | 1984-12-11 |
| NO160362B (no) | 1989-01-02 |
| BR8406684A (pt) | 1985-10-22 |
| MX7317E (es) | 1988-05-12 |
| JPH0481978B2 (forum.php) | 1992-12-25 |
| AU568708B2 (en) | 1988-01-07 |
| JPS60169450A (ja) | 1985-09-02 |
| EP0147990A1 (en) | 1985-07-10 |
| DE3472248D1 (en) | 1988-07-28 |
| NO160362C (no) | 1989-04-12 |
| AU3709684A (en) | 1985-07-04 |
| AR241489A1 (es) | 1992-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |