PL225597B1 - 3,3,5,5-Tetra(dihydroxy phosphoryl)biphenyl and method of manufacturing it - Google Patents
3,3,5,5-Tetra(dihydroxy phosphoryl)biphenyl and method of manufacturing itInfo
- Publication number
- PL225597B1 PL225597B1 PL407781A PL40778114A PL225597B1 PL 225597 B1 PL225597 B1 PL 225597B1 PL 407781 A PL407781 A PL 407781A PL 40778114 A PL40778114 A PL 40778114A PL 225597 B1 PL225597 B1 PL 225597B1
- Authority
- PL
- Poland
- Prior art keywords
- biphenyl
- tetra
- dihydroxyphosphoryl
- tetrabromobiphenyl
- mol
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- NNPMHVXPDNEIPN-UHFFFAOYSA-N (3-phenyl-1,5,5-triphosphonocyclohex-2-en-1-yl)phosphonic acid Chemical group OP(=O)(O)C1(CC(=CC(C1)(P(=O)(O)O)P(=O)(O)O)C1=CC=CC=C1)P(=O)(O)O NNPMHVXPDNEIPN-UHFFFAOYSA-N 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- FXJXZYWFJAXIJX-UHFFFAOYSA-N 1,3-dibromo-5-(3,5-dibromophenyl)benzene Chemical group BrC1=CC(Br)=CC(C=2C=C(Br)C=C(Br)C=2)=C1 FXJXZYWFJAXIJX-UHFFFAOYSA-N 0.000 claims description 7
- MIYVPKNLWJFPGU-UHFFFAOYSA-N [3-(3,5-diphosphonophenyl)-5-phosphonophenyl]phosphonic acid Chemical group C1(=CC(=CC(=C1)P(O)(O)=O)P(O)(O)=O)C1=CC(=CC(=C1)P(O)(O)=O)P(O)(O)=O MIYVPKNLWJFPGU-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- MQYFWRJEFAZXHE-UHFFFAOYSA-N (2-phenylphenyl)phosphonic acid Chemical group OP(O)(=O)C1=CC=CC=C1C1=CC=CC=C1 MQYFWRJEFAZXHE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 3
- NDEHYSJCDSTVKK-UHFFFAOYSA-N CC(C)OP(C1=CC(C2=CC(P(OC(C)C)(OC(C)C)=O)=CC(P(OC(C)C)(OC(C)C)=O)=C2)=CC(P(OC(C)C)(OC(C)C)=O)=C1)(OC(C)C)=O Chemical group CC(C)OP(C1=CC(C2=CC(P(OC(C)C)(OC(C)C)=O)=CC(P(OC(C)C)(OC(C)C)=O)=C2)=CC(P(OC(C)C)(OC(C)C)=O)=C1)(OC(C)C)=O NDEHYSJCDSTVKK-UHFFFAOYSA-N 0.000 claims description 3
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 claims description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- -1 3,3', 5,5'-tetrabromobiphenyl phosphite Chemical compound 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest 3,3’,5,5’-tetra(dihydroksyfosforylo)bifenyl oraz sposób jego wytwarzania znajdujący zastosowanie jako substrat do otrzymywania materiałów hybrydowych wykorzyst ywanych jako katalizatory reakcji heterogenicznych, sensory chemiczne, wymieniacze jonowe, materiały optyki nieliniowej czy adsorbenty gazów.The subject of the invention is 3.3 ', 5.5' -tetra (dihydroxyphosphoryl) biphenyl and a method of its production that can be used as a substrate for the preparation of hybrid materials used as catalysts for heterogeneous reactions, chemical sensors, ion exchangers, nonlinear optics materials and gas adsorbents.
3,3’,5,5’-Tetra(dihydroksyfosforylo)bifenyl o wzorze 1 ma określoną, jednoznaczną budowę przestrzenną i nie został dotychczas opisany w literaturze naukowej i patentowej.The 3.3 ', 5.5' -Tetra (dihydroxyphosphoryl) biphenyl of the formula 1 has a specific, unique three-dimensional structure and has not been described in the scientific and patent literature so far.
Istotą wynalazku jest 3,3’,5,5’-tetra(dihydroksyfosforylo)bifenyl o wzorze 1.The essence of the invention is 3.3 ', 5.5'-tetra (dihydroxyphosphoryl) biphenyl of formula 1.
Sposób wytwarzania 3,3’,5,5’-tetra(dihydroksyfosforylo)bifenylu o wzorze 1 polega na tym, że do otrzymanego znaną metodą 3,3’,5,5’-tetrabromobifenylu dodaje się fosforyn diizopropylowy w stosunku molowym 4,8:1 względem 3,3’,5,5’-tetrabromobifenylu, diizopropyloetyloaminę w stosunku molowym 5,2:1 względem 3,3’,5,5’-tetrabromobifenylu oraz katalizator palladowy i toluen jako rozpuszczalnik i otrzymuje się 3,3’,5,5’-tetrakis(diizopropyloksyfosforylo)bifenyl, po czym w wyniku hydrolizy kwasowej za pomocą stężonego kwasu solnego otrzymuje się 3,3’,5,5’-tetra(dihydroksyfosforylo)bifenyl.The method of producing 3,3 ', 5,5'-tetra (dihydroxyphosphoryl) biphenyl of formula 1 consists in adding diisopropyl phosphite in a molar ratio of 4.8 to the known method of 3,3', 5,5'-tetrabromobiphenyl. : 1 relative to 3,3 ', 5,5'-tetrabromobiphenyl, diisopropylethylamine in a molar ratio of 5,2: 1 relative to 3,3', 5,5'-tetrabromobiphenyl and a palladium catalyst and toluene as solvent to give 3.3 ' , 5,5'-tetrakis (diisopropyloxyphosphoryl) biphenyl followed by acid hydrolysis with concentrated hydrochloric acid to give 3,3 ', 5,5'-tetra (dihydroxyphosphoryl) biphenyl.
Korzystnie jako katalizator palladowy stosuje się kompleks powstały in situ z octanu palladu 4% molowego - i 1,1'-bis(difenylofosfino)ferrocenu - 4,4% molowego.Preferably, the palladium catalyst used is a complex formed in situ from palladium acetate 4 mol% - and 1,1'-bis (diphenylphosphino) ferrocene - 4.4 mol%.
Otrzymany związek w postaci 3,3’,5,5’-tetra(dihydroksyfosforylo)bifenyl został zaprojektowany w taki sposób, aby miał grupy funkcyjne przyłączone do pierścieni w pozycjach 3 i 5. Grupy funkcyjne - fosfonowe mają możliwość przyjmowania dwóch stanów uprotonowania, a każdy z tych stanów ma wiele modów koordynacyjnych. Aromatyczny szkielet bifenylu zapewnia termiczną stabilność i wytrzymałość. Cząsteczka kwasu nie jest płaska, posiada grupy funkcyjne tworzące ze sobą kąt 120°. Taki kształt cząsteczki uprawdopodabnia otrzymywanie trójwymiarowych sieci supramolekularnych.The obtained compound in the form of 3,3 ', 5,5'-tetra (dihydroxyphosphoryl) biphenyl was designed in such a way that it had functional groups attached to the rings at the 3 and 5 positions. each of these states has multiple coordination modes. The aromatic biphenyl backbone provides thermal stability and durability. The acid molecule is not flat, it has functional groups forming an angle of 120 ° with each other. Such a shape of the molecule makes it possible to obtain three-dimensional supramolecular networks.
Przedmiot wynalazku przedstawiony jest bliżej w przykładach wykonania oraz na schemacie reakcji. P r z y k ł a d 1The subject of the invention is presented in more detail in the working examples and in the reaction scheme. P r z k ł a d 1
Etap pierwszy - synteza 3,3’,5,5’-tetrabromobifenyluFirst stage - synthesis of 3.3 ', 5.5'-tetrabromobiphenyl
W trójszyjnej kolbie okrągłodennej o pojemności 500 cm umieszcza się 1,3,5-tribromobenzen 3 (6.00 g, 0.019 mol), rozpuszcza się go w eterze dietylowem (150 cm ). Roztwór ochłodzą się do tem3 peratury -70°C i wkrapla ze strzykawki 1.6M roztwór n-butylolitu w heksanie (18 cm , 0.025 mol). Mieszaninę reakcyjną miesza się magnetycznie przez 1 godzinę w temperaturze -70°C. Następnie dodaje się bezwodny chlorek miedzi(II) (3.38 g, 0.025 mol) i ponownie miesza przez 1 godzinę w temperaturze -70°C. Mieszaninę reakcyjną pozostawia się w temperaturze pokojowej przez noc, po czym dodaje się eter dietylowy (120 cm ) i 10% (m/m) roztwór wodny amoniaku (210 cm ). Rozdziela się fazy, fazę 3 wodną ekstrahuje się eterem dietylowym (120 cm3), a połączone fazy organiczne przemywa solanką 3 (160 cm3) i suszy bezwodnym MgSO4. Po odsączeniu środka suszącego i odparowaniu rozpuszczalnika pozostałość ogrzewa się pod chłodnicą zwrotną z etanolem (25 ml), odsącza część nierozpuszczalną i rekrystalizuje ją z benzenu otrzymując 3,3’,5,5’-tetrabromobifenyl (1.28 g, 29%), t.top. 191-195°C (lit. 190-191°C [Kirai N., Yamamoto Y., Eur. J. Org. Chem., 2009, 12, 1864-1867]); 1H NMR (CDCfe) δ: 7.69 (t, J = 1.69 Hz, 2H, arom. H), 7.59 (d, J = 1.70 Hz, 4H, arom. H). 1,3,5-tribromobenzene 3 (6.00 g, 0.019 mol) is placed in a 500 cm 3-neck round bottom flask and dissolved in diethyl ether (150 cm3). The solution was cooled down to 3 tem perature -70 ° C and added dropwise via syringe 1.6M n-butyllithium in hexane (18 cm, 0.025 mol). The reaction mixture is magnetically stirred for 1 hour at -70 ° C. Anhydrous copper (II) chloride (3.38 g, 0.025 mol) was then added and stirred again for 1 hour at -70 ° C. The reaction mixture is allowed to stand at room temperature overnight, then diethyl ether (120 cm) and a 10% (m / m) aqueous ammonia solution (210 cm) are added. The phases are separated, the aqueous phase is extracted 3 with diethyl ether (120 cm 3) and the combined organic phases were washed with brine 3 (160 cm 3) and dried over anhydrous MgSO4. After filtering off the drying agent and evaporating the solvent, the residue is refluxed with ethanol (25 ml), the insoluble matter is filtered off and recrystallized from benzene to give 3,3 ', 5,5'-tetrabromobiphenyl (1.28 g, 29%), m.p. top. 191-195 ° C (lit. 190-191 ° C [Kirai N., Yamamoto Y., Eur. J. Org. Chem., 2009, 12, 1864-1867]); 1 H NMR (CDCfe) δ: 7.69 (t, J = 1.69 Hz, 2H, arom. H), 7.59 (d, J = 1.70 Hz, 4H, arom. H).
Etap drugi - synteza 3,3’,5,5’-tetrakis(diizopropyloksyfosforylo)bifenylu 3 Second step - synthesis of 3,3 ', 5,5'-tetrakis (diisopropyloxyphosphoryl) biphenyl 3
W kolbie okrągłodennej o pojemności 50 cm umieszcza się 3,3’,5,5’-tetrabromobifenyl (0.50 g, 3 In a 50 cm round bottom flask is placed 3,3 ', 5,5'-tetrabromobiphenyl (0.50 g, 3
1.06 mmol), toluen (5 cm), fosforyn diizopropylowy (0.845 g, 5.09 mmol) i diizopropyloetyloaminę (0.712 g, 5.51 mmol). Kolbę płucze się argonem przez 15 minut, następnie dodaje się octan palladu (0.009 g, 0.040 mmol) i 1,1'-(difenylofosfino)ferrocen (dppf, 0.026 g, 0.05 mmol). Kolbę z mieszaniną reakcyjną zanurza się w łaźni olejowej o temperaturze 90°C i utrzymuje się tę temperaturę przez 24 godziny. Mieszaninę reakcyjną chłodzi się i odsącza osad bromowodorku aminy. Przesącz odparowuje się na wyparce obrotowej a pozostałość poddaje się chromatografii kolumnowej (żel krzemionkowy, eluent: octan etylu/etanol 10:1 (v/v)) aby otrzymać 3,3’,5,5’-tetrakis(diizopropyloksyfosforylo)bifenyl: 0.766 g, 89%, t.top. 48-50°C; 1H NMR (CDCI3) δ: 8.26-8.15 (m, 6H, arom. H), 4.75 (m, J = 6.75 Hz, 8H, CH), 1.39 (d, J = 6.12 Hz, 24H, CH3), 1.25 (d, J = 6.13 Hz, 24H, CH3); 31P{1H} (CDCfe) δ: 14.93 (s).1.06 mmol), toluene (5 cm), diisopropyl phosphite (0.845 g, 5.09 mmol) and diisopropylethylamine (0.712 g, 5.51 mmol). The flask is purged with argon for 15 minutes, then palladium acetate (0.009 g, 0.040 mmol) and 1.1 '- (diphenylphosphino) ferrocene (dppf, 0.026 g, 0.05 mmol) are added. The reaction flask was immersed in a 90 ° C oil bath and kept at this temperature for 24 hours. The reaction mixture is cooled and the precipitate of the amine hydrobromide is filtered off. The filtrate is evaporated on a rotary evaporator and the residue is subjected to column chromatography (silica gel, eluent: ethyl acetate / ethanol 10: 1 (v / v)) to obtain 3,3 ', 5,5'-tetrakis (diisopropyloxyphosphoryl) biphenyl: 0.766 g, 89% mp. 48-50 ° C; 1 H NMR (CDCl3) δ: 8.26-8.15 (m, 6H, arom. H), 4.75 (m, J = 6.75 Hz, 8 H, CH), 1.39 (d, J = 6.12 Hz, 24H, CH 3), 1.25 (d, J = 6.13Hz, 24H, CH3); 31 P {1 H} (CDCfe) δ: 14.93 (s).
Etap trzeci - synteza 3,3’,5,5’-tetra(dihydroksyfosforylo)bifenylu 3 Stage three - synthesis of 3,3 ', 5,5'-tetra (dihydroxyphosphoryl) biphenyl 3
W kolbie okrągłodennej o pojemności 25 cm umieszcza się 3,3’,5,5’-tetrakis(diizo33 propyloksyfosforylo)bifenyl (0.55 g, 0.68 mmol), wodę (2 cm3) i stężony kwas solny (2 cm3). Mieszaninę reakcyjną ogrzewa się w temperaturze wrzenia pod chłodnicą zwrotną przez 20 godzin. Mieszan iPL 225 597 B1 nę reakcyjną ochładza się do temperatury pokojowej i odsącza wytrącony osad 3,3’,5,5’-tetra(dihydroksyfosforylo)bifenylu: 0.22 g, 69%, t.top > 360°C; 1H NMR (D2O) δ: 8.04-7.96 (m, 6H, arom.In a 25 cm round bottom flask is placed 3,3 ', 5,5'-tetrakis (diiso33 propyloxyphosphoryl) biphenyl (0.55 g, 0.68 mmol), water (2 cm 3 ) and concentrated hydrochloric acid (2 cm 3 ). The reaction mixture is refluxed for 20 hours. The reaction mixture iPL 225 597 B1 is cooled to room temperature and the 3,3 ', 5,5'-tetra (dihydroxyphosphoryl) biphenyl precipitate is filtered off: 0.22 g, 69%, mp> 360 ° C; 1 H NMR (D 2 O) δ: 8.04-7.96 (m, 6H, arom.
H); IR (KBr) 3486.60, 3115.68, 3029.27, 1604.14, 1557.68, 1514.95, 1438.15, 1145.69, 1022.75,H); IR (KBr) 3486.60, 3115.68, 3029.27, 1604.14, 1557.68, 1514.95, 1438.15, 1145.69, 1022.75,
812.65 cm-1.812.65 cm -1 .
Claims (3)
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| PL407781A PL225597B1 (en) | 2014-04-03 | 2014-04-03 | 3,3,5,5-Tetra(dihydroxy phosphoryl)biphenyl and method of manufacturing it |
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| Application Number | Priority Date | Filing Date | Title |
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| PL407781A PL225597B1 (en) | 2014-04-03 | 2014-04-03 | 3,3,5,5-Tetra(dihydroxy phosphoryl)biphenyl and method of manufacturing it |
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| Publication Number | Publication Date |
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| PL407781A1 PL407781A1 (en) | 2015-02-16 |
| PL225597B1 true PL225597B1 (en) | 2017-04-28 |
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| Publication number | Publication date |
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