JP5868425B2 - ビフェホスを製造する方法 - Google Patents
ビフェホスを製造する方法 Download PDFInfo
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- JP5868425B2 JP5868425B2 JP2013548772A JP2013548772A JP5868425B2 JP 5868425 B2 JP5868425 B2 JP 5868425B2 JP 2013548772 A JP2013548772 A JP 2013548772A JP 2013548772 A JP2013548772 A JP 2013548772A JP 5868425 B2 JP5868425 B2 JP 5868425B2
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- 238000004519 manufacturing process Methods 0.000 title claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 81
- 239000002904 solvent Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 14
- 239000011877 solvent mixture Substances 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- CBYWHFTZNVZQHV-UHFFFAOYSA-N 2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methoxyphenyl)-4-methoxyphenol Chemical group CC(C)(C)C1=CC(OC)=CC(C=2C(=C(C=C(OC)C=2)C(C)(C)C)O)=C1O CBYWHFTZNVZQHV-UHFFFAOYSA-N 0.000 claims description 8
- AESQDCMZHBUWPN-UHFFFAOYSA-N 4h-1,3,2-dioxaphosphinine Chemical compound C1OPOC=C1 AESQDCMZHBUWPN-UHFFFAOYSA-N 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 239000012267 brine Substances 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 239000000374 eutectic mixture Substances 0.000 claims description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 18
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 18
- 229910052801 chlorine Inorganic materials 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
- -1 3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′diyl Chemical group 0.000 description 5
- 238000007037 hydroformylation reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229940078552 o-xylene Drugs 0.000 description 3
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical group OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000004255 ion exchange chromatography Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RRTJOAHJZQVSSE-UHFFFAOYSA-N 1,3,2-dioxaphosphepine Chemical compound C=1C=COPOC=1 RRTJOAHJZQVSSE-UHFFFAOYSA-N 0.000 description 1
- MRBKEAMVRSLQPH-UHFFFAOYSA-N 3-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1 MRBKEAMVRSLQPH-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009841 combustion method Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- YFWNUYQMEJLXEE-UHFFFAOYSA-N ethyl hexanoate;rhodium Chemical compound [Rh].CCCCCC(=O)OCC YFWNUYQMEJLXEE-UHFFFAOYSA-N 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000005930 hydroaminomethylation reaction Methods 0.000 description 1
- 238000005669 hydrocyanation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
-
- 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
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65744—Esters of oxyacids of phosphorus condensed with carbocyclic or heterocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
・該反応は、通常のブライン冷却を用いて実施可能である、
・80%を超える高い収率を達成することができる、
・ビフェホスは、再結晶せずに3000ppm未満の塩素含有量で得られる、かつ
・水による後処理が行われない。
グローブボックス中で、250mLシュレンクフラスコ中に、アセトニトリル(Fluka社)110mL中の、DE-A 102008043584に従い製造したホスホロクロリジット2 17.5g(0.063モル)を装入した。更に、3,3′−ジ−t−ブチル−2,2′−ジヒドロキシ−5,5′−ジメトキシビフェニル10.4g(0.028モル)を、EP35965に従い調製した。これをピリジン17ml(16.4g、0.204モル)中に溶解させ、100mL滴下漏斗中へ入れた。この滴下漏斗をシュレンクフラスコ上へ載置した。この装置を該グローブボックスから外へ出し、該シュレンクフラスコを−10℃に冷却した。引き続き、強力に撹拌しながら、該ビフェノール/ピリジン溶液を一滴ずつ2.5hかけてゆっくりと計量供給し、その際に固体が沈殿析出した。添加が完了した後に、−10℃で一晩にわたって後撹拌した。その後で、該固体をG3保護ガスガラスフィルターでろ別した。該固体を、引き続き該ガラスフィルター上で保護ガス下にアセトニトリル30ml中に懸濁させ、引き続き改めてろ過した。該無色固体を10-1ミリバールで16時間乾燥させ、引き続き分析した。ビフェホス19.92g(理論の87.3%)が得られた。これは、全塩素2500ppm(±100ppm)を含有していた(分析法:DIN 51408及びDIN EN ISO 10304による、ウイックボルドによる燃焼)。
ホスホロクロリジット2 121g、トルエン中80%を、アセトニトリル530g中に溶解させ、−5℃に冷却した。更に、3,3′−ジ−t−ブチル−2,2′−ジヒドロキシ−5,5′−ジメトキシビフェニル63gを、ピリジン101g中に溶解させ、ゆっくりと該ホスホロクロリジット溶液に計量供給し、その際に該反応溶液を絶えず−5℃に冷却した。計量供給後に、2h後撹拌した。沈殿した生成物を、ヌッチェでろ別し、まず最初にアセトニトリル80mL及び引き続きn−ヘプタン100mLで洗浄し、真空乾燥器中で乾燥させた。1500ppm(±100ppm)の全塩素含有量を有するビフェホス114g(理論の83%)が得られた(分析法:DIN 51408及びDIN EN ISO 10304による、ウイックボルドによる燃焼)。
Claims (7)
- 3,3′−ジ−t−ブチル−2,2′−ジヒドロキシ−5,5′−ジメトキシビフェニルを6−クロロジベンゾ[d,f][1,3,2]−ジオキサホスフェピンと反応させることによりビフェホスを製造する方法であって、
該反応を、塩基としてのピリジンの存在下で、溶剤としてのアセトニトリル中で行う
ことを特徴とする、ビフェホスを製造する方法。 - 該反応を、水及び食塩の共融混合物の晶析温度を上回り+10℃までの温度範囲内で行う、請求項1記載の方法。
- 該反応を−10℃超〜+5℃の温度範囲内で行う、請求項2記載の方法。
- 反応が行われた後に、形成された固体を単離する、請求項1から3までのいずれか1項記載の方法。
- 該固体のろ別後に、この固体を改めて、このために適した溶剤中に懸濁させ、かつろ別する、請求項4記載の方法。
- 反応を行った後に、主にビフェホスからなる固体を、アセトニトリル不含の溶剤又は溶剤混合物中に溶解させ、不溶性成分をろ別し、ビフェホスを該溶剤又は溶剤混合物の冷却により晶出又は沈殿析出させ、引き続き単離する、請求項1から5までのいずれか1項記載の方法。
- ビフェホスの製造方法における溶剤としての、アセトニトリルの使用であって、塩基としてのピリジンの存在下で、該溶剤中で3,3′−ジ−t−ブチル−2,2′−ジヒドロキシ−5,5′−ジメトキシビフェニルを6−クロロジベンゾ[d,f][1,3,2]−ジオキサホスフェピンと反応させる、アセトニトリルの使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102011002639.8 | 2011-01-13 | ||
DE201110002639 DE102011002639A1 (de) | 2011-01-13 | 2011-01-13 | Verfahren zur Herstellung von Biphephos |
PCT/EP2011/073762 WO2012095253A1 (de) | 2011-01-13 | 2011-12-22 | Verfahren zur herstellung von biphephos |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014510028A JP2014510028A (ja) | 2014-04-24 |
JP5868425B2 true JP5868425B2 (ja) | 2016-02-24 |
Family
ID=45476482
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013548772A Active JP5868425B2 (ja) | 2011-01-13 | 2011-12-22 | ビフェホスを製造する方法 |
Country Status (15)
Country | Link |
---|---|
US (1) | US9127030B2 (ja) |
EP (1) | EP2663573B1 (ja) |
JP (1) | JP5868425B2 (ja) |
KR (1) | KR101761455B1 (ja) |
CN (1) | CN103370328B (ja) |
AR (1) | AR084847A1 (ja) |
BR (1) | BR112013017896B1 (ja) |
DE (1) | DE102011002639A1 (ja) |
ES (1) | ES2590154T3 (ja) |
MX (1) | MX336307B (ja) |
MY (1) | MY193184A (ja) |
SG (1) | SG191953A1 (ja) |
TW (1) | TWI542595B (ja) |
WO (1) | WO2012095253A1 (ja) |
ZA (1) | ZA201305972B (ja) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2566069T3 (es) * | 2012-10-12 | 2016-04-08 | Evonik Degussa Gmbh | Procedimiento estable a largo plazo para la preparación de aldehídos de C5 |
DE102014201756A1 (de) | 2014-01-31 | 2015-08-06 | Evonik Degussa Gmbh | Reinigung chlorverschmutzter Organophosphorverbindungen |
DE102014203960A1 (de) | 2014-03-05 | 2015-09-10 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Aldehyden aus Alkanen und Synthesegas |
ES2733102T3 (es) | 2014-12-04 | 2019-11-27 | Evonik Operations Gmbh | Bisfosfitos que presentan un componente central de biarilo asimétrico |
CN105777988B (zh) * | 2014-12-19 | 2018-04-06 | 中国科学院大连化学物理研究所 | 一种含p有机聚合物及其制备方法和应用 |
SG10201601501QA (en) * | 2015-03-05 | 2016-10-28 | Evonik Degussa Gmbh | Preparation of 2,2`-biaryls in the presence of molybdenum(v) chloride |
EP3318570B1 (de) | 2016-11-08 | 2019-08-07 | Evonik Degussa GmbH | Phosphorigsäure-p,p'-[5,5',6,6'-tetramethyl-3,3'-bis(1-methylethyl)[1,1'-biphenyl]-2,2'-diyl] p,p,p',p'-tetrakis(2,4-dimethylphenyl)-ester in der hydroformylierung |
PL3318569T3 (pl) | 2016-11-08 | 2020-03-31 | Evonik Degussa Gmbh | Bisfosfoniany z jednostkami 2,4-tert.-butylofenylu i ich zastosowanie jako ligandów w hydroformylowaniu |
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MY193184A (en) | 2022-09-26 |
CN103370328A (zh) | 2013-10-23 |
WO2012095253A1 (de) | 2012-07-19 |
EP2663573B1 (de) | 2016-06-22 |
CN103370328B (zh) | 2016-06-01 |
EP2663573A1 (de) | 2013-11-20 |
BR112013017896B1 (pt) | 2019-08-20 |
KR101761455B1 (ko) | 2017-07-25 |
US20130324756A1 (en) | 2013-12-05 |
AR084847A1 (es) | 2013-06-26 |
DE102011002639A1 (de) | 2012-07-19 |
BR112013017896A8 (pt) | 2019-06-25 |
ZA201305972B (en) | 2014-04-30 |
MX2013007828A (es) | 2013-09-06 |
ES2590154T3 (es) | 2016-11-18 |
KR20140030127A (ko) | 2014-03-11 |
JP2014510028A (ja) | 2014-04-24 |
MX336307B (es) | 2016-01-14 |
TWI542595B (zh) | 2016-07-21 |
BR112013017896A2 (pt) | 2016-10-11 |
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