PL410360A1 - Quiral polyampholytes derivatives of dimethylphosphinic acid, polyalkylenepolyamines and lysines and method for producing them - Google Patents
Quiral polyampholytes derivatives of dimethylphosphinic acid, polyalkylenepolyamines and lysines and method for producing themInfo
- Publication number
- PL410360A1 PL410360A1 PL410360A PL41036014A PL410360A1 PL 410360 A1 PL410360 A1 PL 410360A1 PL 410360 A PL410360 A PL 410360A PL 41036014 A PL41036014 A PL 41036014A PL 410360 A1 PL410360 A1 PL 410360A1
- Authority
- PL
- Poland
- Prior art keywords
- lysine
- chiral
- fragment
- polyampholyte
- fragments
- Prior art date
Links
- GOJNABIZVJCYFL-UHFFFAOYSA-N dimethylphosphinic acid Chemical class CP(C)(O)=O GOJNABIZVJCYFL-UHFFFAOYSA-N 0.000 title abstract 5
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 235000018977 lysine Nutrition 0.000 title 1
- 150000002669 lysines Chemical class 0.000 title 1
- 239000012634 fragment Substances 0.000 abstract 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 abstract 6
- 239000004472 Lysine Substances 0.000 abstract 6
- 229920001281 polyalkylene Polymers 0.000 abstract 5
- 229920000768 polyamine Polymers 0.000 abstract 5
- OTBHHUPVCYLGQO-UHFFFAOYSA-N 1,7-diamino-4-aza-heptane Natural products NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 abstract 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 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
- 239000007848 Bronsted acid Substances 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
- 239000005700 Putrescine Substances 0.000 abstract 1
- 239000012190 activator Substances 0.000 abstract 1
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 abstract 1
- 238000005119 centrifugation Methods 0.000 abstract 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 abstract 1
- 238000010908 decantation Methods 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001914 filtration Methods 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
- 239000003446 ligand Substances 0.000 abstract 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 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
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000000758 substrate 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Wynalazek dotyczy chiralnych poliamfolitów pochodnych kwasu dimetylofosfinowego, polialkilenopoliamin i lizyny, które są przeznaczone do stosowania jako lizyno specyficzne diastereoselektory, oraz ligandy do wytwarzania chiralnych katalizatorów homogennych i heterogennych, w których w centrum aktywnym jest lizyna. Chiralne poliamfolity 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, y oznacza liczbę fragmentów poliaminopolialkenowych w polimerze, natomiast C oznacza fragment struktury lizyny, a z oznacza liczbę takich fragmentów w poliamfolicie, przy czym wolne miejsca fragmentu A mogą się wiązać tylko z wolnymi miejscami we fragmencie B i C. Ujawniono również sposób wytwarzania chiralnych poliamfolitów pochodnych kwasu dimetylofosfinowego, polialkilenopoliamin i lizyny, przedstawionych wzorem ogólnym I. Sposób 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 lizyny, 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 chiralnego poliamfolitu zawierającego fragmenty strukturalne kwasu dimetylofosfinowego, polialkilenopoliaminy i lizyny, który w trzecim etapie poddaje się dosieciowaniu co najmniej 0,5 części molowej formaldehydu. Otrzymany w wyniku chiralny poliamfolit wydziela się z mieszaniny poreakcyjnej przez dekantację, sączenie lub wirowanie, ewentualnie przez odparowanie lotnych składników pod zmniejszonym ciśnieniem.The invention concerns chiral polyampholytes derived from dimethylphosphinic acid, polyalkylene polyamines and lysine, which are intended for use as lysine-specific diastereoselectors, and ligands for the production of chiral homogeneous and heterogeneous catalysts in which lysine is the active center. Chiral polyampholytes of the general formula I, in which A denotes a fragment of the dimethylphosphinic acid structure, x denotes the number of such fragments in the 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, and 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 lysine structure, and z is the number of such fragments in the polyampholyte, where the free sites of fragment A can only bind to the free sites in the fragment B and C. A method for preparing chiral polyampholytes derived from dimethylphosphinic acid, polyalkylene polyamines and lysine, represented by the general formula I, is also disclosed. The method consists in reacting, in the first step, one mole of phosphinic acid with at least one mole of formaldehyde and at least two molar 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 groups - NH- derived from lysine, 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 chiral polyampholyte is formed containing structural fragments of dimethylphosphinic acid, polyalkylene polyamine and lysine, which in the third At this stage, at least 0.5 mole of formaldehyde is cross-linked. The resulting chiral polyampholyte is isolated from the reaction mixture by decantation, filtration or centrifugation, optionally by evaporation of the volatile components under reduced pressure.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL410360A PL410360A1 (en) | 2014-12-04 | 2014-12-04 | Quiral polyampholytes derivatives of dimethylphosphinic acid, polyalkylenepolyamines and lysines and method for producing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL410360A PL410360A1 (en) | 2014-12-04 | 2014-12-04 | Quiral polyampholytes derivatives of dimethylphosphinic acid, polyalkylenepolyamines and lysines and method for producing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL410360A1 true PL410360A1 (en) | 2015-09-14 |
Family
ID=54065031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL410360A PL410360A1 (en) | 2014-12-04 | 2014-12-04 | Quiral polyampholytes derivatives of dimethylphosphinic acid, polyalkylenepolyamines and lysines and method for producing them |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL410360A1 (en) |
-
2014
- 2014-12-04 PL PL410360A patent/PL410360A1/en unknown
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