PL406279A1 - Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and glutamic acid and the method of their preparation - Google Patents
Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and glutamic acid and the method of their preparationInfo
- Publication number
- PL406279A1 PL406279A1 PL406279A PL40627913A PL406279A1 PL 406279 A1 PL406279 A1 PL 406279A1 PL 406279 A PL406279 A PL 406279A PL 40627913 A PL40627913 A PL 40627913A PL 406279 A1 PL406279 A1 PL 406279A1
- Authority
- PL
- Poland
- Prior art keywords
- acid
- glutamic acid
- chiral
- polyampholyte
- derivatives
- Prior art date
Links
- 229920001281 polyalkylene Polymers 0.000 title abstract 7
- 229920000768 polyamine Polymers 0.000 title abstract 7
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 title abstract 6
- 235000013922 glutamic acid Nutrition 0.000 title abstract 6
- 239000004220 glutamic acid Substances 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
- 239000012634 fragment Substances 0.000 abstract 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- 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
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=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
- 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
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyamides (AREA)
Abstract
Wynalazek dotyczy chiralnych poliamfolitów pochodnych kwasu dimetylofosfinowego, polialkilenopoliamin i kwasu glutaminowego, 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 kwasu glutaminowego, 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 kwasu glutaminowego, 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 obejmującej bis(heksametyleno)triaminę, dietylenotriaminę, N-(3-aminopropylo)-1,3-diaminopropan, N-(2-aminoetylo)-1,3-diaminopropan, 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 grup -NH- pochodzących od kwasu glutaminowego, 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 kwasu glutaminowego, 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 kwasu glutaminowego, 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 glutamic acid, which are intended for use as enantioselectors and diastereoselectors, and complexes for the production 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 glutamic acid, represented by the general formula I, in which A is a fragment of the dimethylphosphinic acid structure, x is the number of such fragments in 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 , while q is the number of aminopolyalkene structures and ranges from 2 to 6, y means the number of polyaminopolyalkene fragments in the polymer, while C means a fragment of the glutamic acid structure, and z means the number of such fragments in polyampholyte, which consists in the fact that in the first stage one mole part phosphinic acid is reacted with at least one molar part of formaldehyde 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-diaminopropane, 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 -NH- groups derived from glutamic acid, 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 glutamic acid is formed, which in the second stage is cross-linked with at least one part 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 glutamic acid, which in the third stage is cross-linked with at least 0.5 mole of formaldehyde, and then obtained chiral polyampholyte is separated from the post-reaction mixture.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL406279A PL221869B1 (en) | 2013-11-27 | 2013-11-27 | Chiral polymapholyte derivatives of dimethylphosphinic acid, glutamic acid and polyalkylene polyamines and process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL406279A PL221869B1 (en) | 2013-11-27 | 2013-11-27 | Chiral polymapholyte derivatives of dimethylphosphinic acid, glutamic acid and polyalkylene polyamines and process for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL406279A1 true PL406279A1 (en) | 2014-07-07 |
| PL221869B1 PL221869B1 (en) | 2016-06-30 |
Family
ID=51063167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL406279A PL221869B1 (en) | 2013-11-27 | 2013-11-27 | Chiral polymapholyte derivatives of dimethylphosphinic acid, glutamic acid and polyalkylene polyamines and process for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL221869B1 (en) |
-
2013
- 2013-11-27 PL PL406279A patent/PL221869B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL221869B1 (en) | 2016-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CY1117157T1 (en) | SUBSTITUTED ISOKINOLIN PRODUCTION | |
| MX2018009317A (en) | Process to prepare higher ethylene amines and ethylene amine derivatives. | |
| MX2018009318A (en) | Process to prepare higher ethylene amines and ethylene amine derivatives. | |
| CY1121484T1 (en) | SALT AND CRYSTAL FORMS OF AN SUSPENDER PLK-4 | |
| EA201591381A1 (en) | NEW BIOACTIVE POLYMERS | |
| PL406279A1 (en) | Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and glutamic acid and the method of their preparation | |
| PL406280A1 (en) | Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and aspartic acid and the method of their preparation | |
| PL406276A1 (en) | Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and asparagine and the method of their preparation | |
| BR112015009779A2 (en) | low molecular weight polymers comprising at least one terminal group 1,3-dioxolan-2-one 4-methyl ether | |
| PL406277A1 (en) | Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and proline and the method of their preparation | |
| PL406275A1 (en) | Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and leucine, isoleucine or norleucine and the method of their preparation | |
| PL406278A1 (en) | Polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and iminodiacetic acid and the method of their preparation | |
| PL406273A1 (en) | Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and glutamine and the method of their preparation | |
| PL406274A1 (en) | Chiral polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and valine and the method of their preparation | |
| PL405424A1 (en) | Chiral poliamfolites derivatives of the dimethylphosphinic acid, polyalkylene polyamines and methionine and a method for their preparation | |
| PL409039A1 (en) | Chiral polyampholites, derivatives of dimethyl organophosphorous acid, polyalkylenepolyamines and phenylalanine and method to produce them | |
| PL410355A1 (en) | Quiral polyampholytes derivatives of dimethylphosphinic acid, polyalkylenepolyamines and serines and method for producing them | |
| PL410358A1 (en) | Quiral polyampholytes derivatives of dimethylphosphinic acid, polyalkylenepolyamines and cysteines and method for producing them | |
| PL410360A1 (en) | Quiral polyampholytes derivatives of dimethylphosphinic acid, polyalkylenepolyamines and lysines and method for producing them | |
| PL410353A1 (en) | Quiral polyampholytes derivatives of dimethylphosphinic acid, polyalkylenepolyamines and cystines and method for producing them | |
| PL404705A1 (en) | Polyampholyte derivatives of dimethylphosphinic acid, polyalkylene polyamines and aminomethylphosphonic acid and the method of their preparation | |
| PL409042A1 (en) | Polyampholites derivatives of dimethylphosphonic acid, polyalkyenepolyamines i N-phosphonomethyl glycine and method to produce them | |
| PL409041A1 (en) | Polyampholites derivatives of dimethylphosphonic acid, polyalkyenepolyamines and imino-bis metylphosphonic acid and method to produce them | |
| PL402707A1 (en) | Derivative polyampholyte of dimethylphosphinic acid, polyalkylenepolyamine and taurine and a method for its manufacture | |
| PL415274A1 (en) | Method for producing per(phosphinemethylated) polyalkylene polyamines |