JPS60169450A - 第二アミノエ−テルアルコ−ルの製造法 - Google Patents
第二アミノエ−テルアルコ−ルの製造法Info
- Publication number
- JPS60169450A JPS60169450A JP59270550A JP27055084A JPS60169450A JP S60169450 A JPS60169450 A JP S60169450A JP 59270550 A JP59270550 A JP 59270550A JP 27055084 A JP27055084 A JP 27055084A JP S60169450 A JPS60169450 A JP S60169450A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- catalyst
- range
- pressure
- carried out
- 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
- -1 secondary amino ether alcohol Chemical compound 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims description 64
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 14
- 238000005984 hydrogenation reaction Methods 0.000 claims description 14
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- VDGMIGHRDCJLMN-UHFFFAOYSA-N [Cu].[Co].[Ni] Chemical compound [Cu].[Co].[Ni] VDGMIGHRDCJLMN-UHFFFAOYSA-N 0.000 claims 1
- 125000004965 chloroalkyl group Chemical group 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 49
- 238000005576 amination reaction Methods 0.000 description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
- 239000006227 byproduct Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- AHXXIYFEJGGBMG-UHFFFAOYSA-N 1-[2-(tert-butylamino)ethoxy]ethanol Chemical compound CC(O)OCCNC(C)(C)C AHXXIYFEJGGBMG-UHFFFAOYSA-N 0.000 description 8
- 230000004913 activation Effects 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- OILJIEKQCVHNMM-UHFFFAOYSA-N 4-tert-butylmorpholine Chemical compound CC(C)(C)N1CCOCC1 OILJIEKQCVHNMM-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000005909 Kieselgur Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical group NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 230000035484 reaction time Effects 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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910001504 inorganic chloride Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PVXVWWANJIWJOO-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-N-ethylpropan-2-amine Chemical compound CCNC(C)CC1=CC=C2OCOC2=C1 PVXVWWANJIWJOO-UHFFFAOYSA-N 0.000 description 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- IUXYVKZUDNLISR-UHFFFAOYSA-N 2-(tert-butylamino)ethanol Chemical compound CC(C)(C)NCCO IUXYVKZUDNLISR-UHFFFAOYSA-N 0.000 description 1
- AKNQPXWJRBJXQR-UHFFFAOYSA-N 2-methylpropan-2-amine;toluene Chemical compound CC(C)(C)N.CC1=CC=CC=C1 AKNQPXWJRBJXQR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QMMZSJPSPRTHGB-UHFFFAOYSA-N MDEA Natural products CC(C)CCCCC=CCC=CC(O)=O QMMZSJPSPRTHGB-UHFFFAOYSA-N 0.000 description 1
- 229910018106 Ni—C Inorganic materials 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 241000219315 Spinacia Species 0.000 description 1
- 235000009337 Spinacia oleracea Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QXZUUHYBWMWJHK-UHFFFAOYSA-N [Co].[Ni] Chemical compound [Co].[Ni] QXZUUHYBWMWJHK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 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
- 230000001771 impaired effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 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
- 239000012263 liquid product Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 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
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 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
- 238000005201 scrubbing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
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 |
| US565097 | 1983-12-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60169450A true JPS60169450A (ja) | 1985-09-02 |
| JPH0481978B2 JPH0481978B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-12-25 |
Family
ID=24257203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59270550A Granted JPS60169450A (ja) | 1983-12-23 | 1984-12-21 | 第二アミノエ−テルアルコ−ルの製造法 |
Country Status (10)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5085092A (en) * | 1988-12-22 | 1992-02-04 | Isuzu Motors Limited | Gear transmission for vehicle |
| JP2007523082A (ja) * | 2004-02-17 | 2007-08-16 | 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 | 金属装填触媒を用いた立体障害の大きなアミノ−エーテルアルコール類の触媒的調製 |
| JP2007523085A (ja) * | 2004-02-17 | 2007-08-16 | 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 | 高活性粉末触媒を用いる高度立体障害アミノ−エーテルアルコールおよびジアミノポリアルケニルエーテルの改良合成 |
| JP2008543955A (ja) * | 2005-06-28 | 2008-12-04 | クラリアント・プロドゥクテ・（ドイチュラント）・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | ポリエーテルアミン製造方法 |
| JP2013523797A (ja) * | 2010-04-07 | 2013-06-17 | ビーエーエスエフ ソシエタス・ヨーロピア | 気相中での不斉第二級ｔｅｒｔ−ブチルアミンの製造方法 |
| JP2015057406A (ja) * | 2006-12-06 | 2015-03-26 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | ポリエーテルアミンの製造方法 |
Families Citing this family (23)
| 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 |
| US4487967A (en) * | 1983-12-23 | 1984-12-11 | Exxon Research & Engineering Co. | Process for preparing secondary aminoether alcohols |
| US4665195A (en) * | 1983-12-23 | 1987-05-12 | Exxon Research And Engineering Company | Process for preparing di-amino-polyalkenyl ethers |
| 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 |
| 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 |
| 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 |
| BR8901452A (pt) * | 1988-03-31 | 1989-11-14 | Union Carbide Corp | Processo para preparar n-(polioxialquil)-n-(alquil)aminas |
| JP4604053B2 (ja) * | 2004-02-17 | 2010-12-22 | 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 | 酸無水物および／または酸ハロゲン化物、並びに三酸化硫黄からの立体障害第二級アミノエーテルアルコールの合成 |
| CA2556508C (en) * | 2004-02-17 | 2012-10-02 | Exxonmobil Research And Engineering Company | Synthesis of sterically hindered secondary aminoether alcohols |
| JP4604049B2 (ja) * | 2004-02-17 | 2010-12-22 | 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 | 立体障害第二級アミノエーテルアルコールの合成 |
| CN1922132B (zh) * | 2004-02-17 | 2010-05-26 | 埃克森美孚研究工程公司 | 由烯酮和/或酰卤和/或羧酸酐合成强空间位阻仲氨基醚醇 |
| EP1919855B1 (en) * | 2005-08-09 | 2014-08-20 | ExxonMobil Research and Engineering Company | Alkylamino alkyloxy (alcohol) monoalkyl ether for acid gas scrubbing process |
| JP5061108B2 (ja) * | 2005-08-09 | 2012-10-31 | 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 | 酸性ガススクラビング法のためのポリアルキレンアクリルアミド塩 |
| US8524184B2 (en) * | 2009-07-08 | 2013-09-03 | Exxonmobil Research And Engineering Company | Sulfur recovery plant tail gas treatment process |
| PL2571845T3 (pl) * | 2010-05-21 | 2015-03-31 | Basf Se | Sposób wytwarzania 2-(2-tert-butyloaminoetoksy)etanolu (tertbutyloaminodiglikolu, TBADG) |
| US8455693B2 (en) | 2010-05-21 | 2013-06-04 | Basf Se | Process for preparing 2-(2-tert-butylaminoethoxy)ethanol (tert-butylaminodiglycol, TBADG) |
| JP7731347B2 (ja) | 2019-09-10 | 2025-08-29 | ビーエーエスエフ ソシエタス・ヨーロピア | 酸性ガスを流体ストリームから除去する方法 |
| 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 |
| JPS5276B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1969-03-03 | 1977-01-05 | ||
| 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 |
| EP0084943B2 (en) * | 1982-01-18 | 1989-08-02 | Exxon Research And Engineering Company | Secondary and tertiary amino alcohols |
| EP0087856B1 (en) * | 1982-01-18 | 1986-02-26 | Exxon Research And Engineering Company | A process for the removal of h2s from gaseous mixtures using diaminoethers |
| 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 DE DE8484308791T patent/DE3472248D1/de not_active Expired
- 1984-12-17 EP EP84308791A patent/EP0147990B1/en not_active Expired
- 1984-12-21 JP JP59270550A patent/JPS60169450A/ja active Granted
- 1984-12-21 AU AU37096/84A patent/AU568708B2/en not_active Ceased
- 1984-12-21 BR BR8406684A patent/BR8406684A/pt not_active IP Right Cessation
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5085092A (en) * | 1988-12-22 | 1992-02-04 | Isuzu Motors Limited | Gear transmission for vehicle |
| JP2007523082A (ja) * | 2004-02-17 | 2007-08-16 | 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 | 金属装填触媒を用いた立体障害の大きなアミノ−エーテルアルコール類の触媒的調製 |
| JP2007523085A (ja) * | 2004-02-17 | 2007-08-16 | 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 | 高活性粉末触媒を用いる高度立体障害アミノ−エーテルアルコールおよびジアミノポリアルケニルエーテルの改良合成 |
| JP2008543955A (ja) * | 2005-06-28 | 2008-12-04 | クラリアント・プロドゥクテ・（ドイチュラント）・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | ポリエーテルアミン製造方法 |
| JP2015057406A (ja) * | 2006-12-06 | 2015-03-26 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | ポリエーテルアミンの製造方法 |
| JP2013523797A (ja) * | 2010-04-07 | 2013-06-17 | ビーエーエスエフ ソシエタス・ヨーロピア | 気相中での不斉第二級ｔｅｒｔ−ブチルアミンの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| MX7317E (es) | 1988-05-12 |
| EP0147990B1 (en) | 1988-06-22 |
| NO160362B (no) | 1989-01-02 |
| AU568708B2 (en) | 1988-01-07 |
| CA1228368A (en) | 1987-10-20 |
| DE3472248D1 (en) | 1988-07-28 |
| NO160362C (no) | 1989-04-12 |
| AR241489A1 (es) | 1992-07-31 |
| NO844388L (no) | 1985-06-24 |
| BR8406684A (pt) | 1985-10-22 |
| US4487967A (en) | 1984-12-11 |
| JPH0481978B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-12-25 |
| EP0147990A1 (en) | 1985-07-10 |
| AU3709684A (en) | 1985-07-04 |
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