CA2508337C - A selective synthesis of organophosphites - Google Patents
A selective synthesis of organophosphites Download PDFInfo
- Publication number
- CA2508337C CA2508337C CA2508337A CA2508337A CA2508337C CA 2508337 C CA2508337 C CA 2508337C CA 2508337 A CA2508337 A CA 2508337A CA 2508337 A CA2508337 A CA 2508337A CA 2508337 C CA2508337 C CA 2508337C
- Authority
- CA
- Canada
- Prior art keywords
- alcohol
- triorganoamine
- solution
- added
- molar
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract description 38
- 238000003786 synthesis reaction Methods 0.000 title abstract description 29
- 150000008301 phosphite esters Chemical class 0.000 title description 6
- 238000000034 method Methods 0.000 claims abstract description 75
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 185
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 177
- 238000007792 addition Methods 0.000 claims description 68
- 238000006243 chemical reaction Methods 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 40
- -1 cycloalkyl radical Chemical class 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000000010 aprotic solvent Substances 0.000 claims description 9
- 125000005270 trialkylamine group Chemical group 0.000 claims description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 3
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims description 3
- VMOWKUTXPNPTEN-UHFFFAOYSA-N n,n-dimethylpropan-2-amine Chemical compound CC(C)N(C)C VMOWKUTXPNPTEN-UHFFFAOYSA-N 0.000 claims description 3
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 claims 2
- 230000008569 process Effects 0.000 abstract description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 315
- 235000019441 ethanol Nutrition 0.000 description 157
- 239000000243 solution Substances 0.000 description 141
- 238000004679 31P NMR spectroscopy Methods 0.000 description 55
- 238000004458 analytical method Methods 0.000 description 47
- 230000009466 transformation Effects 0.000 description 44
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 36
- 238000003756 stirring Methods 0.000 description 30
- 238000009826 distribution Methods 0.000 description 22
- ZDTQJPVEXIUREJ-UHFFFAOYSA-N dichlorophosphinous acid Chemical class OP(Cl)Cl ZDTQJPVEXIUREJ-UHFFFAOYSA-N 0.000 description 21
- 230000002572 peristaltic effect Effects 0.000 description 21
- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical class OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 description 18
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 13
- 230000009977 dual effect Effects 0.000 description 13
- 238000006073 displacement reaction Methods 0.000 description 12
- 238000002156 mixing Methods 0.000 description 11
- 150000001298 alcohols Chemical class 0.000 description 10
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000007865 diluting Methods 0.000 description 6
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 6
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 5
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 229960003750 ethyl chloride Drugs 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000002277 temperature effect Effects 0.000 description 3
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000006462 rearrangement reaction Methods 0.000 description 2
- 230000003252 repetitive effect Effects 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MUVQKFGNPGZBII-UHFFFAOYSA-N 1-anthrol Chemical class C1=CC=C2C=C3C(O)=CC=CC3=CC2=C1 MUVQKFGNPGZBII-UHFFFAOYSA-N 0.000 description 1
- GTBXZWADMKOZQJ-UHFFFAOYSA-N 1-phenanthrol Chemical class C1=CC2=CC=CC=C2C2=C1C(O)=CC=C2 GTBXZWADMKOZQJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101100229907 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) GPP2 gene Proteins 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 102220254284 rs755928199 Human genes 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/146—Esters of phosphorous acids containing P-halide groups
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/142—Esters of phosphorous acids with hydroxyalkyl compounds without further substituents on alkyl
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/145—Esters of phosphorous acids with hydroxyaryl compounds
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43042602P | 2002-12-02 | 2002-12-02 | |
| US60/430,426 | 2002-12-02 | ||
| US10/454,043 | 2003-06-04 | ||
| US10/454,043 US20040106815A1 (en) | 2002-12-02 | 2003-06-04 | Selective synthesis of organophosphites |
| PCT/US2003/038367 WO2004050588A2 (en) | 2002-12-02 | 2003-12-02 | A selective synthesis of organophosphites |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2508337A1 CA2508337A1 (en) | 2004-06-17 |
| CA2508337C true CA2508337C (en) | 2013-01-29 |
Family
ID=32397248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2508337A Expired - Fee Related CA2508337C (en) | 2002-12-02 | 2003-12-02 | A selective synthesis of organophosphites |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20040106815A1 (OSRAM) |
| EP (3) | EP2239248B2 (OSRAM) |
| JP (1) | JP2006508177A (OSRAM) |
| AT (1) | ATE501998T1 (OSRAM) |
| AU (1) | AU2003294564A1 (OSRAM) |
| CA (1) | CA2508337C (OSRAM) |
| DE (1) | DE60336419D1 (OSRAM) |
| ES (1) | ES2526971T3 (OSRAM) |
| WO (1) | WO2004050588A2 (OSRAM) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2849027B1 (fr) * | 2002-12-23 | 2005-01-21 | Rhodia Polyamide Intermediates | Procede de synthese de composes comprenant des fonctions nitriles a partir de composes a insaturations ethyleniques |
| FR2850966B1 (fr) | 2003-02-10 | 2005-03-18 | Rhodia Polyamide Intermediates | Procede de fabrication de composes dinitriles |
| FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
| FR2854892B1 (fr) * | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
| CZ2008547A3 (cs) * | 2006-03-17 | 2009-06-10 | Invista Technologies S. A. R. L. | Zpusob purifikace triorganofosfitu ošetrením bazickým aditivem |
| EP2044092B1 (de) * | 2006-07-12 | 2011-09-28 | Basf Se | Verfahren zur herstellung von halogene enthaltenden organischen phosphorverbindungen |
| US7709673B2 (en) * | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| US7919646B2 (en) * | 2006-07-14 | 2011-04-05 | Invista North America S.A R.L. | Hydrocyanation of 2-pentenenitrile |
| US7709674B2 (en) * | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L | Hydrocyanation process with reduced yield losses |
| US7880028B2 (en) * | 2006-07-14 | 2011-02-01 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| US7659422B2 (en) * | 2006-07-14 | 2010-02-09 | Invista North America S.A.R.L. | Hydrocyanation process with reduced yield losses |
| EP2229354B1 (en) * | 2008-01-15 | 2013-03-20 | Invista Technologies S.à.r.l. | Process for making and refining 3-pentenenitrile, and for refining 2-methyl-3-butenenitrile |
| EP2229353B1 (en) * | 2008-01-15 | 2018-01-03 | INVISTA Textiles (U.K.) Limited | Hydrocyanation of pentenenitriles |
| US8471066B2 (en) * | 2008-03-28 | 2013-06-25 | Union Carbide Chemicals & Plastics Technology Llc | Slurry process for phosphoromonochloridite synthesis |
| US20100227988A1 (en) * | 2008-12-29 | 2010-09-09 | Coalter Iii Joseph N | Catalyst Composition with Phosphorus-Based Donor and Method |
| WO2010123743A1 (en) | 2009-04-21 | 2010-10-28 | Invista Technologies S.A R.L. | Highly selective process for producing organodiphosphites |
| EP2459577A1 (en) * | 2009-07-31 | 2012-06-06 | Chemtura Corporation | Liquid alkylated trisaryl phosphite compositions having two alkyl groups with different carbon number |
| DK2658651T3 (en) | 2009-12-18 | 2019-01-14 | Invista Textiles Uk Ltd | NICKEL COMPOSITIONS FOR THE MANUFACTURE OF NICKEL METAL AND NICKEL COMPLEXS |
| CN103080119B (zh) | 2010-09-07 | 2015-04-08 | 因温斯特技术公司 | 用于制备镍金属的镍组合物和镍配合物 |
| JP2014522408A (ja) | 2011-06-10 | 2014-09-04 | インヴィスタ テクノロジーズ エスアエルエル | 金属−配位子触媒形成の改善 |
| JP2014523481A (ja) | 2011-06-10 | 2014-09-11 | インヴィスタ テクノロジーズ エスアエルエル | 流動床反応器を含む焼成プロセス及び還元プロセス |
| HK1199035A1 (en) | 2011-10-26 | 2015-06-19 | 因温斯特技术公司 | Methods for producing organodiphosphites from phosphorochloridites characterized by measuring side-product levels to determine further additions |
| CN103739622A (zh) * | 2014-01-06 | 2014-04-23 | 重庆中平紫光科技发展有限公司 | 两步法合成亚磷酸三芳酯的方法 |
| EP3585840B1 (de) | 2017-08-04 | 2020-06-03 | Wacker Chemie AG | Durch bestrahlung mit uv-licht vernetzbare siliconzusammensetzungen |
| CN116917301A (zh) * | 2021-03-03 | 2023-10-20 | 国立大学法人东京工业大学 | 非对称型磷酸三酯的制造方法、对称型磷酸三酯的制造方法、磷酸酯的制造方法、以及有机磷化合物的制造方法 |
| US20250296945A1 (en) | 2022-05-23 | 2025-09-25 | Inv Nylon Chemicals Americas, Llc | Multidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| US20250296076A1 (en) | 2022-05-23 | 2025-09-25 | Inv Nylon Chemicals Americas, Llc | Multidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| EP4499653A1 (en) | 2022-08-02 | 2025-02-05 | INVISTA Textiles (U.K.) Limited | Bidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| EP4499654A1 (en) | 2022-08-02 | 2025-02-05 | INVISTA Textiles (U.K.) Limited | Bidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| WO2024028720A1 (en) | 2022-08-02 | 2024-02-08 | Inv Nylon Chemicals Americas, Llc | Bidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| WO2024028719A2 (en) | 2022-08-02 | 2024-02-08 | Inv Nylon Chemicals Americas, Llc | Bidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| WO2024028716A1 (en) | 2022-08-02 | 2024-02-08 | Inv Nylon Chemicals Americas, Llc | Processes for producing nitriles and phosphorus-containing catalysts for use in such processes |
| EP4499604A1 (en) | 2022-08-02 | 2025-02-05 | INVISTA Textiles (U.K.) Limited | Processes for producing nitriles and phosphorus-containing catalysts for use in such processes |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2533989A (en) * | 1947-08-30 | 1950-12-12 | Standard Oil Dev Co | Antioxidants for greases and similar materials |
| US2877259A (en) * | 1954-09-10 | 1959-03-10 | Us Rubber Co | Di-(alkyl)-mono-(alkylphenyl)-phosphites |
| DE1050746B (de) * | 1956-07-06 | 1959-02-19 | Ciba Aktiengesellschaft, Basel (Schweiz) | Verfahren zur Herstellung von Trialkylphosphiten |
| US3057904A (en) * | 1958-09-04 | 1962-10-09 | Monsanto Chemicals | Preparation of esters of trivalent phosphorus acids |
| US4120917A (en) | 1977-03-28 | 1978-10-17 | Mobil Oil Corporation | Process for preparing tertiary alkylphosphorodichloridites |
| JPS56152863A (en) * | 1980-04-28 | 1981-11-26 | Adeka Argus Chem Co Ltd | Synthetic resin composition |
| US4764634A (en) * | 1986-01-06 | 1988-08-16 | Akzo America Inc. | Preparation of organic phosphinites |
| US5235086A (en) * | 1989-08-15 | 1993-08-10 | Ciba-Geigy Corporation | Process for the preparation of tris(2,4-ditert-butylphenyl)phosphite |
| JPH03123790A (ja) * | 1989-10-05 | 1991-05-27 | Lion Corp | リン酸エステルの製造方法 |
| US5103035A (en) * | 1990-04-05 | 1992-04-07 | Ethyl Corporation | Process for preparing bis(alkylphenyl)pentaerythritol diphosphites |
| TW213465B (OSRAM) * | 1991-06-11 | 1993-09-21 | Mitsubishi Chemicals Co Ltd | |
| IN187044B (OSRAM) | 1995-01-27 | 2002-01-05 | Du Pont | |
| US6069267A (en) * | 1997-07-29 | 2000-05-30 | E. I. Du Pont De Nemours And Company | Selective synthesis of organodiphosphite compounds |
| US6420611B1 (en) * | 1999-09-20 | 2002-07-16 | E. I. Du Pont De Nemours And Company | Composition comprising polymeric phosphite |
| DE19953048A1 (de) | 1999-11-03 | 2001-05-10 | Basf Ag | Verfahren zur Herstellung von Organophosphiten |
| GB0104778D0 (en) | 2001-02-27 | 2001-04-18 | Rhodia Cons Spec Ltd | Production of aromatic phosphites |
| US6653494B2 (en) * | 2001-11-26 | 2003-11-25 | Strides Inc. | Processes for producing triaryl phosphite |
-
2003
- 2003-06-04 US US10/454,043 patent/US20040106815A1/en not_active Abandoned
- 2003-12-02 WO PCT/US2003/038367 patent/WO2004050588A2/en not_active Ceased
- 2003-12-02 AU AU2003294564A patent/AU2003294564A1/en not_active Abandoned
- 2003-12-02 JP JP2004570997A patent/JP2006508177A/ja not_active Ceased
- 2003-12-02 EP EP10170520.0A patent/EP2239248B2/en not_active Expired - Lifetime
- 2003-12-02 EP EP10170500.2A patent/EP2243763B2/en not_active Expired - Lifetime
- 2003-12-02 CA CA2508337A patent/CA2508337C/en not_active Expired - Fee Related
- 2003-12-02 AT AT03787252T patent/ATE501998T1/de not_active IP Right Cessation
- 2003-12-02 EP EP03787252A patent/EP1567468B1/en not_active Expired - Lifetime
- 2003-12-02 ES ES10170500.2T patent/ES2526971T3/es not_active Expired - Lifetime
- 2003-12-02 DE DE60336419T patent/DE60336419D1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2508337A1 (en) | 2004-06-17 |
| JP2006508177A (ja) | 2006-03-09 |
| EP1567468A2 (en) | 2005-08-31 |
| EP2243763A3 (en) | 2010-12-29 |
| AU2003294564A8 (en) | 2004-06-23 |
| EP2243763A2 (en) | 2010-10-27 |
| ATE501998T1 (de) | 2011-04-15 |
| US20040106815A1 (en) | 2004-06-03 |
| EP2239248B2 (en) | 2021-06-09 |
| HK1085194A1 (zh) | 2006-08-18 |
| EP1567468A4 (en) | 2008-01-23 |
| WO2004050588A3 (en) | 2004-09-23 |
| AU2003294564A1 (en) | 2004-06-23 |
| DE60336419D1 (de) | 2011-04-28 |
| EP2239248A3 (en) | 2010-12-29 |
| EP2243763B1 (en) | 2014-10-08 |
| ES2526971T3 (es) | 2015-01-19 |
| WO2004050588A2 (en) | 2004-06-17 |
| EP2243763B2 (en) | 2022-07-06 |
| EP2239248B1 (en) | 2015-09-23 |
| EP1567468B1 (en) | 2011-03-16 |
| EP2239248A2 (en) | 2010-10-13 |
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