DE2748293C3 - Verfahren zur Alkylierung von sekundären aliphatischen Aminen - Google Patents
Verfahren zur Alkylierung von sekundären aliphatischen AminenInfo
- Publication number
- DE2748293C3 DE2748293C3 DE2748293A DE2748293A DE2748293C3 DE 2748293 C3 DE2748293 C3 DE 2748293C3 DE 2748293 A DE2748293 A DE 2748293A DE 2748293 A DE2748293 A DE 2748293A DE 2748293 C3 DE2748293 C3 DE 2748293C3
- Authority
- DE
- Germany
- Prior art keywords
- secondary aliphatic
- aliphatic amines
- alkylation
- anhydrous
- 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
- 150000005619 secondary aliphatic amines Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 6
- 230000029936 alkylation Effects 0.000 title claims description 5
- 238000005804 alkylation reaction Methods 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 229910052758 niobium Inorganic materials 0.000 claims description 2
- 229910052715 tantalum Inorganic materials 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- JINMQTUDKFCYJG-UHFFFAOYSA-N n,2-dimethylhexan-1-amine Chemical compound CCCCC(C)CNC JINMQTUDKFCYJG-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- QKYWADPCTHTJHQ-UHFFFAOYSA-N n,2-dimethylpropan-1-amine Chemical compound CNCC(C)C QKYWADPCTHTJHQ-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- FBYAIWPYHNBQES-UHFFFAOYSA-N n,2-dimethylundecan-1-amine Chemical compound CCCCCCCCCC(C)CNC FBYAIWPYHNBQES-UHFFFAOYSA-N 0.000 description 1
- KFYKZKISJBGVMR-UHFFFAOYSA-N n-ethylbutan-2-amine Chemical compound CCNC(C)CC KFYKZKISJBGVMR-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT28778/76A IT1068433B (it) | 1976-10-28 | 1976-10-28 | Procedimento per l'lachilazione di ammine secondarie alifatiche |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2748293A1 DE2748293A1 (de) | 1978-05-03 |
| DE2748293B2 DE2748293B2 (de) | 1979-06-21 |
| DE2748293C3 true DE2748293C3 (de) | 1980-02-14 |
Family
ID=11224167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2748293A Expired DE2748293C3 (de) | 1976-10-28 | 1977-10-27 | Verfahren zur Alkylierung von sekundären aliphatischen Aminen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4110377A (show.php) |
| JP (1) | JPS5356602A (show.php) |
| BE (1) | BE860281A (show.php) |
| CH (1) | CH626321A5 (show.php) |
| DE (1) | DE2748293C3 (show.php) |
| FR (1) | FR2369243A1 (show.php) |
| GB (1) | GB1578238A (show.php) |
| IT (1) | IT1068433B (show.php) |
| NL (1) | NL7711767A (show.php) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0019365A3 (en) * | 1979-05-11 | 1981-06-10 | Imperial Chemical Industries Plc | Long chain amine derivatives and process for their preparation |
| US4302603A (en) * | 1980-12-18 | 1981-11-24 | Allied Chemical Corporation | Producing alkylamines from olefins with alkali metal amide catalyst |
| JP2005506404A (ja) * | 2001-10-12 | 2005-03-03 | ダウ グローバル テクノロジーズ インコーポレイティド | 金属錯体組成物、及び金属錯体組成物のポリジエン製造用触媒としての使用法 |
| JP2009174638A (ja) | 2008-01-24 | 2009-08-06 | Jtekt Corp | 樹脂製プーリ |
| US8399725B2 (en) | 2008-06-20 | 2013-03-19 | Exxonmobil Chemical Patents Inc. | Functionalized high vinyl terminated propylene based oligomers |
| US8283419B2 (en) | 2008-06-20 | 2012-10-09 | Exxonmobil Chemical Patents Inc. | Olefin functionalization by metathesis reaction |
| US8283428B2 (en) | 2008-06-20 | 2012-10-09 | Exxonmobil Chemical Patents Inc. | Polymacromonomer and process for production thereof |
| US8372930B2 (en) | 2008-06-20 | 2013-02-12 | Exxonmobil Chemical Patents Inc. | High vinyl terminated propylene based oligomers |
| US8802797B2 (en) | 2008-06-20 | 2014-08-12 | Exxonmobil Chemical Patents Inc. | Vinyl-terminated macromonomer oligomerization |
| JP5471629B2 (ja) * | 2010-03-10 | 2014-04-16 | 株式会社島津製作所 | 液体クロマトグラフ用分析システム及び該分析システムの制御プログラム |
| US8623974B2 (en) | 2011-03-25 | 2014-01-07 | Exxonmobil Chemical Patents Inc. | Branched vinyl terminated polymers and methods for production thereof |
| US8940839B2 (en) | 2011-03-25 | 2015-01-27 | Exxonmobil Chemical Patents Inc. | Diblock copolymers prepared by cross metathesis |
| US8426659B2 (en) | 2011-03-25 | 2013-04-23 | Exxonmobil Chemical Patents Inc. | Vinyl terminated higher olefin polymers and methods to produce thereof |
| US8501894B2 (en) | 2011-03-25 | 2013-08-06 | Exxonmobil Chemical Patents Inc. | Hydrosilyation of vinyl macromers with metallocenes |
| US8318998B2 (en) | 2011-03-25 | 2012-11-27 | Exxonmobil Chemical Patents Inc. | Enhanced catalyst performance for production of vinyl terminated propylene and ethylene/propylene macromers |
| US8669330B2 (en) | 2011-03-25 | 2014-03-11 | Exxonmobil Chemical Patents Inc. | Olefin triblock polymers via ring-opening metathesis polymerization |
| WO2012134716A2 (en) | 2011-03-25 | 2012-10-04 | Exxonmobil Chemical Patents Inc., A Corporation Of The State Of Deleware | Block copolymers from silylated vinyl terminated macromers |
| US8399724B2 (en) | 2011-03-25 | 2013-03-19 | Exxonmobil Chemical Patents Inc. | Vinyl terminated higher olefin copolymers and methods to produce thereof |
| US8669326B2 (en) | 2011-03-25 | 2014-03-11 | Exxonmobil Chemical Patents Inc. | Amine functionalized polyolefin and methods for preparation thereof |
| US8835563B2 (en) | 2011-03-25 | 2014-09-16 | Exxonmobil Chemical Patents Inc. | Block copolymers from silylated vinyl terminated macromers |
| ES2750378T3 (es) | 2011-03-25 | 2020-03-25 | Exxonmobil Chemical Patents Inc | Poliolefina funcionalizada con amina y métodos para su preparación |
| US8841397B2 (en) | 2011-03-25 | 2014-09-23 | Exxonmobil Chemical Patents Inc. | Vinyl terminated higher olefin polymers and methods to produce thereof |
| US8785562B2 (en) | 2011-03-25 | 2014-07-22 | Exxonmobil Chemical Patents Inc. | Amphiphilic block polymers prepared by alkene metathesis |
| US8455597B2 (en) | 2011-03-25 | 2013-06-04 | Exxonmobil Chemical Patents Inc. | Catalysts and methods of use thereof to produce vinyl terminated polymers |
| US8604148B2 (en) | 2011-11-29 | 2013-12-10 | Exxonmobil Chemical Patents Inc. | Functionalization of vinyl terminated polymers by ring opening cross metathesis |
| US8796376B2 (en) | 2012-03-26 | 2014-08-05 | Exxonmobil Chemical Patents Inc. | Functionalized polymers and oligomers |
| US9334343B2 (en) | 2012-09-24 | 2016-05-10 | Exxonmobil Chemical Patents Inc. | Hydrohalogenation of vinyl-terminated macromonomers and functionalized derivatives |
| US9376512B2 (en) | 2012-09-24 | 2016-06-28 | Exxonmobil Chemical Patents Inc. | Production of vinyl terminated polyethylene |
| US9273163B2 (en) | 2012-09-24 | 2016-03-01 | Exxonmobil Chemical Patents Inc. | Hydrosilation of vinyl-terminated macromonomers |
| US9388255B2 (en) | 2012-09-24 | 2016-07-12 | Exxonmobil Chemical Patents Inc. | Oxygenation of vinyl-terminated macromonomers |
| WO2014047531A1 (en) | 2012-09-24 | 2014-03-27 | Exxonmobil Chemical Patents Inc. | Hydroamination of aldehyde-containing macromonomers |
| WO2014047256A1 (en) | 2012-09-24 | 2014-03-27 | Exxonmobil Chemical Patents Inc. | Catalytic hydroformylation of vinyl terminated polyolefins |
| US9434795B2 (en) | 2012-09-24 | 2016-09-06 | Exxonmobil Chemical Patents Inc. | Production of vinyl terminated polyethylene using supported catalyst system |
| US9382350B2 (en) | 2012-09-24 | 2016-07-05 | Exxonmobil Chemical Patents Inc. | Friedel crafts alkylation of aromatics using vinyl terminated macromonomers |
| WO2014047248A1 (en) | 2012-09-24 | 2014-03-27 | Exxonmobil Chemical Patents, Inc. | Branched polyethylenes by hydrosilation grafting to improve processability of polyethylene |
| US10882932B2 (en) | 2016-10-05 | 2021-01-05 | Exxonmobil Chemical Patents Inc. | Sterically hindered metallocenes, synthesis and use |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA526875A (en) * | 1956-06-26 | O. Depree David | Alkali metal amides | |
| US2501556A (en) * | 1949-12-16 | 1950-03-21 | Du Pont | Alkali metals and their hydrides as catalysts in amine condensation |
| US2750417A (en) * | 1953-04-14 | 1956-06-12 | Ethyl Corp | Amine alkylation |
| US2814646A (en) * | 1954-04-29 | 1957-11-26 | Ethyl Corp | Amine alkylation using aluminum anilide catalyst |
| US3884833A (en) * | 1965-09-28 | 1975-05-20 | Studiengesellschaft Kohle Mbh | A zero-valent nickel compound-amine catalyst |
| IL27721A (en) * | 1966-04-15 | 1971-03-24 | Sentralinst For Ind Forskning | Process for dimerization,codimerization,polymerization and copolymerization of mono-olefins |
| US3420864A (en) * | 1966-04-18 | 1969-01-07 | Monsanto Co | Phosphorus and arsenic tri-imide metal compounds |
| FR2088610A5 (show.php) * | 1970-04-17 | 1972-01-07 | Commissariat Energie Atomique | |
| US3691095A (en) * | 1970-09-16 | 1972-09-12 | Exxon Research Engineering Co | Catalyst for olefin reactions |
| US3917607A (en) * | 1971-09-22 | 1975-11-04 | Shell Oil Co | Block copolymer adhesive compositions |
| US3794604A (en) * | 1971-09-24 | 1974-02-26 | Goodyear Tire & Rubber | Diolefin polymerization catalyst composition |
-
1976
- 1976-10-28 IT IT28778/76A patent/IT1068433B/it active
-
1977
- 1977-09-07 US US05/831,241 patent/US4110377A/en not_active Expired - Lifetime
- 1977-09-16 CH CH1136877A patent/CH626321A5/it not_active IP Right Cessation
- 1977-09-20 GB GB39218/77A patent/GB1578238A/en not_active Expired
- 1977-10-24 FR FR7731953A patent/FR2369243A1/fr active Granted
- 1977-10-26 NL NL7711767A patent/NL7711767A/xx not_active Application Discontinuation
- 1977-10-27 DE DE2748293A patent/DE2748293C3/de not_active Expired
- 1977-10-27 JP JP12821477A patent/JPS5356602A/ja active Pending
- 1977-10-28 BE BE182192A patent/BE860281A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2369243A1 (fr) | 1978-05-26 |
| DE2748293B2 (de) | 1979-06-21 |
| FR2369243B1 (show.php) | 1980-06-20 |
| US4110377A (en) | 1978-08-29 |
| IT1068433B (it) | 1985-03-21 |
| DE2748293A1 (de) | 1978-05-03 |
| BE860281A (fr) | 1978-04-28 |
| NL7711767A (nl) | 1978-05-03 |
| JPS5356602A (en) | 1978-05-23 |
| CH626321A5 (show.php) | 1981-11-13 |
| GB1578238A (en) | 1980-11-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAP | Request for examination filed | ||
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |