CN104093729B - 防止多亚磷酸酯配体生产中的溶剂结晶 - Google Patents
防止多亚磷酸酯配体生产中的溶剂结晶 Download PDFInfo
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- CN104093729B CN104093729B CN201280053359.4A CN201280053359A CN104093729B CN 104093729 B CN104093729 B CN 104093729B CN 201280053359 A CN201280053359 A CN 201280053359A CN 104093729 B CN104093729 B CN 104093729B
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- crystal
- polyphosphite
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- solvent
- cleaning solvent
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- 239000002904 solvent Substances 0.000 title claims abstract description 86
- 238000002425 crystallisation Methods 0.000 title description 9
- 230000008025 crystallization Effects 0.000 title description 9
- 239000013078 crystal Substances 0.000 claims abstract description 58
- 238000004140 cleaning Methods 0.000 claims abstract description 42
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 26
- 150000003333 secondary alcohols Chemical class 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 15
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 125000003158 alcohol group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229940090181 propyl acetate Drugs 0.000 claims description 5
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 78
- 238000002156 mixing Methods 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 69
- 239000000463 material Substances 0.000 description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- -1 isopropanol (IPA)) Chemical class 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- 239000002585 base Substances 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000012535 impurity Substances 0.000 description 12
- 238000004679 31P NMR spectroscopy Methods 0.000 description 11
- 239000004305 biphenyl Substances 0.000 description 11
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 10
- 238000006482 condensation reaction Methods 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000007872 degassing Methods 0.000 description 5
- 239000013557 residual solvent Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004957 naphthylene group Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 241001550224 Apha Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000006136 alcoholysis reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- ZDTQJPVEXIUREJ-UHFFFAOYSA-N dichlorophosphinous acid Chemical class OP(Cl)Cl ZDTQJPVEXIUREJ-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZNELGKMVOGFPME-UHFFFAOYSA-N 3H-dioxaphosphepine hepta-1,3-diene Chemical compound O1OPC=CC=C1.C=CC=CCCC ZNELGKMVOGFPME-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- CFSHHEIMVJOLDA-UHFFFAOYSA-N CCC(C)(C(C)=C)N Chemical compound CCC(C)(C(C)=C)N CFSHHEIMVJOLDA-UHFFFAOYSA-N 0.000 description 1
- 206010015856 Extrasystoles Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NQNAVUBSCYWOPD-UHFFFAOYSA-N P(O)(O)Cl.P(O)(O)(O)=O Chemical compound P(O)(O)Cl.P(O)(O)(O)=O NQNAVUBSCYWOPD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000002023 wood Substances 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
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3721/CHE/2011 | 2011-10-31 | ||
| IN3721CH2011 | 2011-10-31 | ||
| PCT/US2012/061874 WO2013066712A1 (en) | 2011-10-31 | 2012-10-25 | Preventing solvent of crystallization in production of polyphosphite ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104093729A CN104093729A (zh) | 2014-10-08 |
| CN104093729B true CN104093729B (zh) | 2016-09-07 |
Family
ID=47144151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201280053359.4A Active CN104093729B (zh) | 2011-10-31 | 2012-10-25 | 防止多亚磷酸酯配体生产中的溶剂结晶 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10227365B2 (enExample) |
| EP (1) | EP2773649B1 (enExample) |
| JP (2) | JP6170059B2 (enExample) |
| CN (1) | CN104093729B (enExample) |
| IN (1) | IN2014CN03131A (enExample) |
| WO (1) | WO2013066712A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013098370A1 (en) * | 2011-12-30 | 2013-07-04 | 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 |
| 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 |
| US9108988B2 (en) | 2011-12-30 | 2015-08-18 | Basf Se | Method of purifying organic diphosphite compounds |
| US10501486B2 (en) | 2014-05-14 | 2019-12-10 | Dow Technology Investments Llc | Stabilized organophosphorous compounds |
| MX2017015818A (es) * | 2015-06-19 | 2018-05-28 | Dow Technology Investments Llc | Ligando cristalino de 6,6'-[[3,3',5,5'-tetraquis(1,1-dimetiletil)- [1,1'-bifenil]-2,2'-diil]bis(oxi)]bisdibenzo[d,f][1,3,2]-dioxafos fepina. |
| TWI709568B (zh) * | 2015-09-30 | 2020-11-11 | 美商陶氏科技投資公司 | 用於製造有機磷化合物的方法 |
| TWI709566B (zh) * | 2015-09-30 | 2020-11-11 | 美商陶氏科技投資公司 | 用於製造有機磷化合物的方法 |
| JP7324147B2 (ja) * | 2017-06-19 | 2023-08-09 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | リガンドを精製するためのプロセス |
| CN118843652A (zh) | 2022-04-13 | 2024-10-25 | 陶氏环球技术有限责任公司 | 制备聚醚官能有机硅化合物 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4318845A (en) * | 1980-11-24 | 1982-03-09 | Ciba-Geigy Corporation | Alkanolamine esters of 1,1'-biphenyl-2,2'-diyl-and alkylidene-1,1'-biphenyl-2,2'-diyl-cyclic phosphites |
| US5334739A (en) * | 1992-11-30 | 1994-08-02 | Ciba-Geigy Corporation | Process an alpha monoclinic crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl)phosphite] |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4182704A (en) * | 1976-07-30 | 1980-01-08 | Ciba-Geigy Corporation | Hindered phenyl phosphites |
| DE2733796A1 (de) * | 1976-07-30 | 1978-02-02 | Ciba Geigy Ag | Neue gehinderte phosphite |
| US4196117A (en) * | 1978-01-03 | 1980-04-01 | Ciba-Geigy Corporation | Alkylated 1,1'-biphenyl-2,2'-diyl phosphites and stabilized compositions |
| US4351759A (en) * | 1978-01-03 | 1982-09-28 | Ciba-Geigy Corporation | Alkylated 2,2'-biphenylene phosphites and stabilized compositions |
| DE2940548A1 (de) | 1979-10-06 | 1981-04-16 | Hoechst Ag, 6000 Frankfurt | Kristallisiertes tris-(2-tert.-butylphenyl)-phosphit und verfahren zu seiner herstellung |
| JPS58103537A (ja) * | 1981-12-15 | 1983-06-20 | Adeka Argus Chem Co Ltd | 安定化された合成樹脂組成物 |
| US4668651A (en) | 1985-09-05 | 1987-05-26 | Union Carbide Corporation | Transition metal complex catalyzed processes |
| US4835299A (en) * | 1987-03-31 | 1989-05-30 | Union Carbide Corporation | Process for purifying tertiary organophosphites |
| JPH01121368A (ja) * | 1987-11-06 | 1989-05-15 | Adeka Argus Chem Co Ltd | 安定化された合成樹脂組成物 |
| ES2059113T3 (es) * | 1989-12-08 | 1994-11-01 | Uniroyal Chem Co Inc | Metodo para preparar aril-fosfitos estericamente impedidos. |
| JP3416956B2 (ja) * | 1991-06-11 | 2003-06-16 | 三菱化学株式会社 | ヒドロホルミル化法およびビスホスファイト化合物 |
| TW213465B (enExample) * | 1991-06-11 | 1993-09-21 | Mitsubishi Chemicals Co Ltd | |
| US5360938A (en) | 1991-08-21 | 1994-11-01 | Union Carbide Chemicals & Plastics Technology Corporation | Asymmetric syntheses |
| US5288918A (en) | 1992-09-29 | 1994-02-22 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process |
| DE4238567A1 (de) * | 1992-11-16 | 1994-05-19 | Henkel Kgaa | Stabilisatormischungen für Polymerisate mit Granaten |
| DK0730574T3 (da) | 1993-11-23 | 1999-05-25 | Du Pont | Fremgangsmåder og katalysatorsammensætninger til hydrocyanering af monoolefiner |
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| JPH1053595A (ja) * | 1996-05-10 | 1998-02-24 | Sumitomo Chem Co Ltd | アリールホスファイト類及びその製造方法 |
| US6031120A (en) | 1997-07-29 | 2000-02-29 | E. I. Du Pont De Nemours And Company | Selective synthesis of organodiphosphite compounds |
| DE10360771A1 (de) | 2003-12-23 | 2005-07-28 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von dreiwertigen Organophosphor-Verbindungen |
| CN102177171B (zh) * | 2008-10-08 | 2014-02-12 | 陶氏技术投资有限公司 | 合成二亚磷酸酯的淤浆方法 |
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- 2012-10-25 EP EP12783477.8A patent/EP2773649B1/en active Active
- 2012-10-25 WO PCT/US2012/061874 patent/WO2013066712A1/en not_active Ceased
- 2012-10-25 US US14/355,392 patent/US10227365B2/en active Active
- 2012-10-25 CN CN201280053359.4A patent/CN104093729B/zh active Active
- 2012-10-25 JP JP2014538998A patent/JP6170059B2/ja active Active
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2017
- 2017-02-10 JP JP2017022824A patent/JP6420385B2/ja active Active
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| US4318845A (en) * | 1980-11-24 | 1982-03-09 | Ciba-Geigy Corporation | Alkanolamine esters of 1,1'-biphenyl-2,2'-diyl-and alkylidene-1,1'-biphenyl-2,2'-diyl-cyclic phosphites |
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Also Published As
| Publication number | Publication date |
|---|---|
| US10227365B2 (en) | 2019-03-12 |
| JP2017114881A (ja) | 2017-06-29 |
| CN104093729A (zh) | 2014-10-08 |
| JP6170059B2 (ja) | 2017-07-26 |
| JP6420385B2 (ja) | 2018-11-07 |
| EP2773649A1 (en) | 2014-09-10 |
| EP2773649B1 (en) | 2017-07-12 |
| IN2014CN03131A (enExample) | 2015-07-03 |
| WO2013066712A1 (en) | 2013-05-10 |
| JP2014532653A (ja) | 2014-12-08 |
| US20140288322A1 (en) | 2014-09-25 |
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