JP6943770B2 - 6,6’−[[3,3’,5,5’−テトラキス(1,1−ジメチルエチル)−[1,1’−ビフェニル]−2,2’−ジイル]ビス(オキシ)]ビスジベンゾ[d,f][1,3,2]−ジオキサホスフェピンの結晶配位子 - Google Patents
6,6’−[[3,3’,5,5’−テトラキス(1,1−ジメチルエチル)−[1,1’−ビフェニル]−2,2’−ジイル]ビス(オキシ)]ビスジベンゾ[d,f][1,3,2]−ジオキサホスフェピンの結晶配位子 Download PDFInfo
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- 239000013078 crystal Substances 0.000 title claims description 21
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title claims description 12
- 235000010290 biphenyl Nutrition 0.000 title claims description 6
- 239000003446 ligand Substances 0.000 title description 76
- PKAUJJPTOIWMDM-UHFFFAOYSA-N 3h-dioxaphosphepine Chemical compound C=1C=CPOOC=1 PKAUJJPTOIWMDM-UHFFFAOYSA-N 0.000 title description 2
- 239000002904 solvent Substances 0.000 claims description 20
- 230000007704 transition Effects 0.000 claims description 8
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- 238000004817 gas chromatography Methods 0.000 claims description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 5
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 238000004949 mass spectrometry Methods 0.000 claims description 3
- 229910017488 Cu K Inorganic materials 0.000 claims 1
- 229910017541 Cu-K Inorganic materials 0.000 claims 1
- 239000012453 solvate Substances 0.000 description 53
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
- 238000000034 method Methods 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000002002 slurry Substances 0.000 description 18
- 238000002441 X-ray diffraction Methods 0.000 description 17
- 239000007787 solid Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000000113 differential scanning calorimetry Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 9
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- 238000002474 experimental method Methods 0.000 description 9
- 238000002411 thermogravimetry Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 238000007037 hydroformylation reaction Methods 0.000 description 7
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- 239000000126 substance Substances 0.000 description 7
- 239000013557 residual solvent Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- -1 isopropanol Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000001665 trituration Methods 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 150000003333 secondary alcohols Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 238000010977 unit operation Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000004807 desolvation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229940090181 propyl acetate Drugs 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- RRTJOAHJZQVSSE-UHFFFAOYSA-N 1,3,2-dioxaphosphepine Chemical compound C=1C=COPOC=1 RRTJOAHJZQVSSE-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012685 metal catalyst precursor Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2419—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65744—Esters of oxyacids of phosphorus condensed with carbocyclic or heterocyclic rings or ring systems
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Description
以下の実施例における全ての部及びパーセンテージは、他に示さない限り重量による。
出発物質は、US2014/0288322の実施例1の方法に従って調製された配位子Aの酢酸エチル溶媒和物であり、8.25重量%の酢酸エチルを含有する。その配位子(2g)を30mLのイソプロパノールで、N2下、45℃で、約1時間スラリー化する。固体を45℃で濾過し、15mLのイソプロパノールで洗浄し、室温で一晩真空乾燥させる。残留溶媒含有量は0.5重量%未満である。この物質のXRDを図2に示す。
配位子を23℃でスラリー化する以外は、実施例1の手順を繰り返す。残留溶媒含有量は0.5重量%未満である。この物質のXRDは、図2に示すものと同じである。
配位子を75℃で3時間スラリー化する以外は実施例1を繰り返す。混合物を約1時間周囲温度に冷却する。固体を収集し、周囲温度で一晩真空乾燥させる。XRDによって確認されるように、非溶媒和物が観察される。図3を参照されたい。
スラリーを週末にわたって撹拌する以外は実施例2を繰り返す。乾燥生成物の残留溶媒のGC分析は、酢酸エチル及びイソプロパノールが0.5重量%未満であり、XRDディフラクトグラムが実施例1の生成物に匹敵することを示す。
配位子A(3.2g)を70℃でトルエン(30g)に溶解させ、次いで45℃でイソプロパノール中でスラリー化する前に、45重量%のトルエンを真空下で濃縮する。得られた物質を濾過するが、その後のイソプロパノールのすすぎをせずに、乾燥させる。得られた物質は0.3%の残留溶媒を含有するが、溶媒和物形態と一致するXRDパターンを与える(例えば、以下C.E.C、及びUS8,796,481の図1のものと同一)。XRDデータと合わせた溶媒含量の欠如は、その物質が脱溶媒和化同形体であることを示す。この物質は、図6に示されている比較的特徴のないDSCパターンを有し、このパターンはUS2013/0225849の図2で観察されたものと同様であり、この物質は非溶媒和物の融点を欠いている(図4参照)。
US2014/0288322の実施例1の方法に従って調製した配位子A 15.1gの溶液を脱気した酢酸エチル230mLに70℃で溶解し、次いで数時間かけて周囲温度に冷却する。得られた酢酸エチル溶媒和物結晶を濾過し、2日間減圧下で乾燥させる。得られた物質は、図7に示す酢酸エチル溶媒和物のXRDディフラクトグラムを示す。
(態様)
(態様1)
Cu−Kα線による25℃で測定した粉末X線ディフラクトグラムにおいて7.8±0.2°及び19.7±0.2°に2θ値で示される2つの最強の反射を提示する、6,6’−[[3,3’,5,5’−テトラキス(1,1−ジメチルエチル)−[1,1’−ビフェニル]−2,2’−ジイル]ビス(オキシ)]ビスジベンゾ[d,f][1,3,2]−ジオキサホスフェピンの結晶形態。
(態様2)
前記ディフラクトグラムが、以下の反射のうちの少なくとも3つを示す、態様1に記載の結晶形態。
溶媒を含まない、態様1または2のいずれかに記載の結晶形態。
(態様4)
Cu−Kα線による25℃で測定した粉末X線ディフラクトグラムにおいて、8.5±0.2°の2θに有意な反射を欠く、態様1〜3のいずれか1項に記載の結晶形態。
(態様5)
DSCによって測定される際、202〜208℃の融点を有する、態様1〜4のいずれか1項に記載の結晶形態。
(態様6)
206℃でのピークを有する初期吸熱遷移を示すDSCプロットを有する、態様5に記載の結晶形態。
(態様7)
図2のXRDディフラクトグラムを有する、態様1〜6のいずれか1項に記載の結晶形態。
(態様8)
図9の線BのTGAプロットを有する、態様1〜7のいずれか1項に記載の結晶形態。
Claims (4)
- Cu−Kα線による25℃で測定した粉末X線ディフラクトグラムにおいて7.8±0.2°及び19.7±0.2°に2θ値で示される2つのピークを提示し、そのうちの一方のピークがもう一方の最も高いピークの最大強度の60%より大きい、6,6’−[[3,3’,5,5’−テトラキス(1,1−ジメチルエチル)−[1,1’−ビフェニル]−2,2’−ジイル]ビス(オキシ)]ビスジベンゾ[d,f][1,3,2]−ジオキサホスフェピンの結晶形態であって、
内部標準としてデカンを使用したガスクロマトグラフィー(GC)/質量分析(MS)によって測定した溶媒含量が0.5重量%未満であり、
DSCによって測定される際、202〜208℃の融点を有し、
前記ディフラクトグラムが、以下のピークのうちの少なくとも3つを示す、結晶形態。
- Cu−Kα線による25℃で測定した粉末X線ディフラクトグラムにおいて、8.5±0.2°の2θに最も高いピークの最大強度の5%を超えるバックグラウンド補正された強度を有するピークがない、請求項1に記載の結晶形態。
- 206℃でのピークを有する初期吸熱遷移を示すDSCプロットを有する、請求項1〜2のいずれか一項に記載の結晶形態。
- 請求項1の表中のピークのうちの少なくとも5つを示す、請求項1〜3のいずれか1項に記載の結晶形態。
Applications Claiming Priority (3)
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US201562182017P | 2015-06-19 | 2015-06-19 | |
US62/182,017 | 2015-06-19 | ||
PCT/US2016/037474 WO2016205264A1 (en) | 2015-06-19 | 2016-06-15 | Crystalline ligand 6,6'-[[3,3',5,5'-tetrakis(1,1 -dimethylethyl)-[1,1 '-biphenyl]-2,2'-diyl]bis(oxy)]bisdibenzo[d,f][1,3,2]-dioxaphos phepin |
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EP (1) | EP3310798B1 (ja) |
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CN (2) | CN107690435A (ja) |
BR (1) | BR112017025337B1 (ja) |
CA (1) | CA2990035A1 (ja) |
MX (1) | MX2017015818A (ja) |
MY (1) | MY191012A (ja) |
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RU2770753C2 (ru) | 2017-06-19 | 2022-04-21 | Дау Текнолоджи Инвестментс Ллк | Способы очистки лигандов |
CN113845547A (zh) * | 2021-10-29 | 2021-12-28 | 山东京博石油化工有限公司 | 一种Biphephos的结晶溶剂化物和非溶剂化结晶形式及其制备方法和应用 |
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US4668651A (en) | 1985-09-05 | 1987-05-26 | Union Carbide Corporation | Transition metal complex catalyzed processes |
US5312996A (en) | 1992-06-29 | 1994-05-17 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process for producing 1,6-hexanedials |
US5326802A (en) * | 1992-11-30 | 1994-07-05 | Ciba-Geigy Corporation | Beta crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-buytl-1,1'-biphenyl-2,2'-diyl)phosphite] |
US6653494B2 (en) * | 2001-11-26 | 2003-11-25 | Strides Inc. | Processes for producing triaryl phosphite |
CN1986055B (zh) | 2006-12-22 | 2012-06-27 | 中国科学院上海有机化学研究所 | 一种丙烯氢甲酰化催化体系和方法 |
CN101684130B (zh) * | 2008-09-25 | 2013-05-01 | 上海焦化有限公司 | 一种亚磷酸酯的制备方法 |
CN102432638B (zh) * | 2010-09-29 | 2015-03-11 | 中国石油化工股份有限公司 | 一种双亚磷酸酯配位体的合成方法 |
DE102011002640B4 (de) * | 2011-01-13 | 2021-10-07 | Evonik Operations Gmbh | Verfahren zur Aufreinigung von Biphephos |
EP2773649B1 (en) * | 2011-10-31 | 2017-07-12 | Dow Technology Investments LLC | Preventing solvent of crystallization in production of polyphosphite ligands |
MY164954A (en) * | 2011-12-30 | 2018-02-28 | Basf Se | Method for purifying organic diphosphite compounds |
BR112014016137B1 (pt) * | 2011-12-30 | 2021-02-09 | Basf Se | forma cristalina não solvatada, monossolvato de tolueno cristalino, solvato de acetona cristalino, composição, processo para a preparação do monossolvato de tolueno cristalino, processo para a preparação de uma forma cristalina não solvatada, processo para a preparação do solvato de acetona cristalino, método para obter o solvato de acetona cristalino, uso de uma forma cristalina, e, método para produzir um catalisador de metal de transição |
US9108988B2 (en) | 2011-12-30 | 2015-08-18 | Basf Se | Method of purifying organic diphosphite compounds |
US8796481B2 (en) | 2011-12-30 | 2014-08-05 | Basf Se | Crystalline solvate and non-solvated forms of 6,6′-[[3,3′,5,5′-tetrakis(1,1-dimethylethyl)-[1,1′biphenyl]-2,2′-diyl]bis(oxy)]bis-dibenzo [d,f] [1,3,2]-dioxaphosphepine |
US10501486B2 (en) | 2014-05-14 | 2019-12-10 | Dow Technology Investments Llc | Stabilized organophosphorous compounds |
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TW201700488A (zh) | 2017-01-01 |
KR102643851B1 (ko) | 2024-03-07 |
ZA201800038B (en) | 2019-07-31 |
EP3310798A1 (en) | 2018-04-25 |
CA2990035A1 (en) | 2016-12-22 |
US10077281B2 (en) | 2018-09-18 |
RU2017145927A (ru) | 2019-06-27 |
BR112017025337A2 (pt) | 2018-07-31 |
MY191012A (en) | 2022-05-28 |
RU2735683C2 (ru) | 2020-11-05 |
RU2017145927A3 (ja) | 2019-12-19 |
BR112017025337B1 (pt) | 2021-01-19 |
CN116396333A (zh) | 2023-07-07 |
JP2018517694A (ja) | 2018-07-05 |
WO2016205264A1 (en) | 2016-12-22 |
MX2017015818A (es) | 2018-05-28 |
TWI695009B (zh) | 2020-06-01 |
EP3310798B1 (en) | 2019-08-21 |
KR20180019647A (ko) | 2018-02-26 |
US20180141968A1 (en) | 2018-05-24 |
CN107690435A (zh) | 2018-02-13 |
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