PL406277A1 - Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and proline and the method of their preparation - Google Patents
Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and proline and the method of their preparationInfo
- Publication number
- PL406277A1 PL406277A1 PL406277A PL40627713A PL406277A1 PL 406277 A1 PL406277 A1 PL 406277A1 PL 406277 A PL406277 A PL 406277A PL 40627713 A PL40627713 A PL 40627713A PL 406277 A1 PL406277 A1 PL 406277A1
- Authority
- PL
- Poland
- Prior art keywords
- proline
- chiral
- mole
- polyampholyte
- derivatives
- Prior art date
Links
- 229920001281 polyalkylene Polymers 0.000 title abstract 7
- 229920000768 polyamine Polymers 0.000 title abstract 7
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 title abstract 5
- GOJNABIZVJCYFL-UHFFFAOYSA-N dimethylphosphinic acid Chemical class CP(C)(O)=O GOJNABIZVJCYFL-UHFFFAOYSA-N 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 2
- 239000012634 fragment Substances 0.000 abstract 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- 235000013930 proline Nutrition 0.000 abstract 5
- OTBHHUPVCYLGQO-UHFFFAOYSA-N 1,7-diamino-4-aza-heptane Natural products NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 abstract 2
- 239000007848 Bronsted acid Substances 0.000 abstract 2
- 239000012190 activator Substances 0.000 abstract 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 abstract 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 abstract 2
- 239000000758 substrate Substances 0.000 abstract 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 abstract 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 abstract 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 abstract 1
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 abstract 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- OHWRASKXEUIFFB-UHFFFAOYSA-N NCP(O)=O Chemical class NCP(O)=O OHWRASKXEUIFFB-UHFFFAOYSA-N 0.000 abstract 1
- 239000005700 Putrescine Substances 0.000 abstract 1
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 abstract 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 abstract 1
- 239000002638 heterogeneous catalyst Substances 0.000 abstract 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002815 homogeneous catalyst Substances 0.000 abstract 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- DTSDBGVDESRKKD-UHFFFAOYSA-N n'-(2-aminoethyl)propane-1,3-diamine Chemical compound NCCCNCCN DTSDBGVDESRKKD-UHFFFAOYSA-N 0.000 abstract 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 abstract 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000012451 post-reaction mixture Substances 0.000 abstract 1
- 150000003148 prolines Chemical class 0.000 abstract 1
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Wynalazek dotyczy chiralnych poliamfolitów pochodnych kwasu dimetylofosfinowego, polialkilenopoliamin i proliny, które są przeznaczone do stosowania jako enancjoselektory i diastereoselektory, oraz kompleksony do wytwarzania chiralnych katalizatorów homogennych i heterogennych, przedstawionych wzorem ogólnym I. Wynalazek dotyczy również sposobu wytwarzania chiralnych poliamfolitów pochodnych kwasu dimetylofosfinowego, polialkilenopoliamin i proliny, przedstawionych wzorem ogólnym I, w którym A oznacza fragment struktury kwasu dimetylofosfinowego, x oznacza liczbę takich fragmentów w poliamfolicie, natomiast B oznacza fragment struktury polialkilenopoliaminy, w którym n i p mogą być takie same lub różne i oznaczają liczby całkowite od 2 do 12, natomiast q jest liczbą struktur aminopolialkenowych i wynosi od 2 do 6, y oznacza liczbę fragmentów poliaminopolialkenowych w polimerze, natomiast C oznacza fragment struktury proliny, a z oznacza liczbę takich fragmentów w poliamfolicie, który polega na tym, że w pierwszym etapie jedną część molową kwasu fosfinowego poddaje się reakcji z co najmniej jedną częścią molową formaldehydu i co najmniej dwiema częściami molowymi grup -NH-, na które składa się suma grup -NH- pochodzących od polialkilenopoliaminy wybranej z grupy zawierającej: 1,2-diaminoetan, 1,3- diaminopropan, 1,4-diaminobutan, 1,5-diaminopentan, 1,6-diaminoheksan, 2-metylo-1,5-diaminopentan, 1,2-diaminocykloheksan, bis(heksametyleno)triaminę, dietylenotriaminę, N-(3- aminopropylo)-1,3-diaminopropan, N-(2-aminoetylo)-1,3-diaminopropan, N,N'-bis(3-aminopropylo)etylenodiaminę, trietylenotetraminę, tetraetylenopentaminę i pentaetylenoheksaminę, i grup -NH- pochodzących od proliny, a reakcję prowadzi się w temperaturze 273-373K, w wodzie, w obecności aktywatora w postaci dowolnego kwasu Bronsteda, aż do przereagowania substratów i utworzenia się mieszaniny kwasów aminometylofosfinowych, pochodnych polialkilenopoliamin i proliny, którą w drugim etapie poddaje się usieciowaniu co najmniej jedną częścią molową formaldehydu w obecności aktywatora w postaci dowolnego kwasu Bronsteda aż do przereagowania substratów i utworzenia się chiralnego poliamfolitu zawierającego fragmenty strukturalne kwasu dimetylofosfinowego, polialkilenopoliaminy i proliny, który w trzecim etapie poddaje się dosieciowaniu co najmniej 0,5 części molowej formaldehydu, po czym tak otrzymany chiralny poliamfolit wydziela się z mieszaniny poreakcyjnej.The invention relates to chiral polyampholytes derivatives of dimethylphosphinic acid, polyalkylene polyamines and proline, which are intended for use as enantioselectors and diastereoselectors, and complexes for the preparation of chiral homogeneous and heterogeneous catalysts, represented by the general formula I. The invention also relates to a method for preparing chiral polyampholytes derivatives of dimethylphosphinic acid, polyalkylene polyamines and prolines, represented by the general formula I, in which A denotes a fragment of the dimethylphosphinic acid structure, x denotes the number of such fragments in polyampholyte, and B denotes a fragment of the polyalkylene polyamine structure, in which n and p may be the same or different and denote integers from 2 to 12, while q is the number of aminopolyalkene structures and ranges from 2 to 6, y is the number of polyaminopolyalkene fragments in the polymer, while C is a fragment of the proline structure, and z is the number of such fragments in polyampholyte, which consists in the fact that in the first step one mole of phosphinic acid is subjected to consisting of reaction with at least one mole part of formaldehyde and at least two mole parts of -NH- groups, which consist of the sum of -NH- groups derived from a polyalkylene polyamine selected from the group containing: 1,2-diaminoethane, 1,3-diaminopropane, 1 ,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 2-methyl-1,5-diaminopentane, 1,2-diaminocyclohexane, bis(hexamethylene)triamine, diethylenetriamine, N-(3-aminopropyl)-1 ,3-diaminopropane, N-(2-aminoethyl)-1,3-diaminopropane, N,N'-bis(3-aminopropyl)ethylenediamine, triethylenetetramine, tetraethylenepentamine and pentaethylenehexamine, and -NH- groups derived from proline, and the reaction is carried out at a temperature of 273-373K, in water, in the presence of an activator in the form of any Bronsted acid, until the substrates are reacted and a mixture of aminomethylphosphinic acids, polyalkylene polyamine derivatives and proline is formed, which in the second step is cross-linked with at least one mole of formaldehyde in the presence of activator in the form of any Bronsted acid until the substrates are reacted and a chiral polyampholyte is formed containing structural fragments of dimethylphosphinic acid, polyalkylene polyamine and proline, which in the third stage is cross-linked with at least 0.5 mole of formaldehyde, after which the chiral polyampholyte thus obtained is isolated from post-reaction mixture.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL406277A PL221871B1 (en) | 2013-11-27 | 2013-11-27 | Chiral polymapholyte derivatives of dimethylphosphinic acid, proline and polyalkylene polyamines and a process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL406277A PL221871B1 (en) | 2013-11-27 | 2013-11-27 | Chiral polymapholyte derivatives of dimethylphosphinic acid, proline and polyalkylene polyamines and a process for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL406277A1 true PL406277A1 (en) | 2014-07-07 |
| PL221871B1 PL221871B1 (en) | 2016-06-30 |
Family
ID=51063165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL406277A PL221871B1 (en) | 2013-11-27 | 2013-11-27 | Chiral polymapholyte derivatives of dimethylphosphinic acid, proline and polyalkylene polyamines and a process for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL221871B1 (en) |
-
2013
- 2013-11-27 PL PL406277A patent/PL221871B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL221871B1 (en) | 2016-06-30 |
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