PL406273A1 - Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and glutamine and the method of their preparation - Google Patents
Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and glutamine and the method of their preparationInfo
- Publication number
- PL406273A1 PL406273A1 PL406273A PL40627313A PL406273A1 PL 406273 A1 PL406273 A1 PL 406273A1 PL 406273 A PL406273 A PL 406273A PL 40627313 A PL40627313 A PL 40627313A PL 406273 A1 PL406273 A1 PL 406273A1
- Authority
- PL
- Poland
- Prior art keywords
- glutamine
- chiral
- polyampholyte
- derivatives
- acid
- Prior art date
Links
- 229920001281 polyalkylene Polymers 0.000 title abstract 7
- 229920000768 polyamine Polymers 0.000 title abstract 7
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 title abstract 6
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 9
- 239000012634 fragment Substances 0.000 abstract 7
- 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
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 abstract 1
- 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
- 125000003277 amino group Chemical group 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
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 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
- 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
- 229920002866 paraformaldehyde Polymers 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
- 239000000126 substance Substances 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
Abstract
Wynalazek dotyczy chiralnych poliamfolitów pochodnych kwasu dimetylofosfinowego, polialkilenopoliamin i glutaminy, które są przeznaczone do stosowania jako enancjoselektory i diastereoselektory, oraz kompleksony do wytwarzania chiralnych katalizatorów homogennych i heterogennych, przedstawionych wzorem ogólnym I. Sposób wytwarzania chiralnych poliamfolitów pochodnych kwasu dimetylofosfinowego, polialkilenopoliamin i glutaminy o wzorze 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, a y oznacza liczbę fragmentów poliaminopolialkenowych w polimerze, natomiast C oznacza fragment struktury glutaminy, a z oznacza takich fragmentów w poliamfolicie, charakteryzuje się tym, że w pierwszym etapie jedną część molową kwasu fosfinowego poddaje się reakcji z co najmniej jedną częścią molową formaldehydu zawartego w substancji wybranej z grupy formalina, trioksan, paraform, i co najmniej dwiema częściami molowymi grup -NH-, na które składa się suma grup -NH- pochodzących od polialkilenopoliaminy wybranej z grupy obejmującej bis(heksametyleno)triaminę, dietylenotriaminę, N-(3-aminopropylo)-1,3-diaminopropan, N-(2-aminoetylo)-1,3-diammopropan, N,N'-bis(3-aminopropylo)etylenodiaminę, trietylenotetraminę, tetraetylenopentaminę, pentaetylenoheksaminę, 1,2-diaminoetan, 1,3-diaminopropan, 1,4-diaminobutan, 1,5-diaminopentan, 1,6-diaminoheksan, 2-metylo-1,5-diaminopentan i 1,2-diaminocykloheksan, i aminowych grup -NH- pochodzących od glutaminy, 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 glutaminy, 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 glutaminy, 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 glutamine, 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. A method for preparing chiral polyampholytes derivatives of dimethylphosphinic acid, polyalkylene polyamines and glutamine of the formula general I, in which A is a fragment of the dimethylphosphinic acid structure, x is the number of such fragments in the polyampholyte, and B is a fragment of the polyalkylene polyamine structure, in which n and p may be the same or different and represent integers from 2 to 12, and q is the number of structures aminopolyalkenes and ranges from 2 to 6, and y denotes the number of polyaminopolyalkene fragments in the polymer, while C denotes a fragment of the glutamine structure, and z denotes such fragments in polyampholyte, characterized by the fact that in the first step one mole part of phosphinic acid is reacted with at least one a molar part of formaldehyde contained in a substance selected from the group formalin, trioxane, paraform, and at least two molar parts of -NH- groups consisting of the sum of -NH- groups derived from a polyalkylene polyamine selected from the group consisting of bis(hexamethylene)triamine, diethylenetriamine, N-(3-aminopropyl)-1,3-diaminopropane, N-(2-aminoethyl)-1,3-diammopropane, N,N'-bis(3-aminopropyl)ethylenediamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, 1,2 -diaminoethane, 1,3-diaminopropane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 2-methyl-1,5-diaminopentane and 1,2-diaminocyclohexane, and amino groups -NH- derived from glutamine, 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 glutamine is formed, which in the second stage is cross-linked at least one mole of formaldehyde in the presence of an 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 glutamine, which in the third step is cross-linked with at least 0.5 mole of formaldehyde, and then the obtained chiral polyampholyte is separated from the post-reaction mixture.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL406273A PL221470B1 (en) | 2013-11-27 | 2013-11-27 | Chiral polymapholyte derivatives of dimethylphosphinic acid, glutamine and polyalkylene polyamines and a process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL406273A PL221470B1 (en) | 2013-11-27 | 2013-11-27 | Chiral polymapholyte derivatives of dimethylphosphinic acid, glutamine and polyalkylene polyamines and a process for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL406273A1 true PL406273A1 (en) | 2014-07-07 |
| PL221470B1 PL221470B1 (en) | 2016-04-29 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL406273A PL221470B1 (en) | 2013-11-27 | 2013-11-27 | Chiral polymapholyte derivatives of dimethylphosphinic acid, glutamine and polyalkylene polyamines and a process for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL221470B1 (en) |
-
2013
- 2013-11-27 PL PL406273A patent/PL221470B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL221470B1 (en) | 2016-04-29 |
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