ES2526971T3 - Una síntesis selectiva de organofosfitos - Google Patents
Una síntesis selectiva de organofosfitos Download PDFInfo
- Publication number
- ES2526971T3 ES2526971T3 ES10170500.2T ES10170500T ES2526971T3 ES 2526971 T3 ES2526971 T3 ES 2526971T3 ES 10170500 T ES10170500 T ES 10170500T ES 2526971 T3 ES2526971 T3 ES 2526971T3
- Authority
- ES
- Spain
- Prior art keywords
- triorganoamine
- alcohol
- 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 - Lifetime
Links
- 230000015572 biosynthetic process Effects 0.000 title description 39
- 238000003786 synthesis reaction Methods 0.000 title description 30
- 150000008301 phosphite esters Chemical class 0.000 title description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 187
- 238000007792 addition Methods 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 64
- 238000006243 chemical reaction Methods 0.000 claims abstract description 60
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 166
- 239000000203 mixture Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000000010 aprotic solvent Substances 0.000 claims description 9
- 125000003158 alcohol group Chemical group 0.000 claims description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005270 trialkylamine group Chemical group 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims description 2
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 claims description 2
- VMOWKUTXPNPTEN-UHFFFAOYSA-N n,n-dimethylpropan-2-amine Chemical compound CC(C)N(C)C VMOWKUTXPNPTEN-UHFFFAOYSA-N 0.000 claims description 2
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 309
- 235000019441 ethanol Nutrition 0.000 description 157
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 59
- 238000004679 31P NMR spectroscopy Methods 0.000 description 52
- 230000009466 transformation Effects 0.000 description 43
- 238000004458 analytical method Methods 0.000 description 36
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 32
- -1 aromatic alcohols Chemical class 0.000 description 30
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 27
- 238000003756 stirring Methods 0.000 description 26
- 238000009826 distribution Methods 0.000 description 22
- 230000002572 peristaltic effect Effects 0.000 description 21
- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 description 19
- ZDTQJPVEXIUREJ-UHFFFAOYSA-N dichlorophosphinous acid Chemical class OP(Cl)Cl ZDTQJPVEXIUREJ-UHFFFAOYSA-N 0.000 description 19
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 230000008569 process Effects 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 238000006073 displacement reaction Methods 0.000 description 12
- 230000009977 dual effect Effects 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 229960004756 ethanol Drugs 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 8
- 239000011574 phosphorus Substances 0.000 description 8
- 229910052698 phosphorus Inorganic materials 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
- 150000001412 amines Chemical class 0.000 description 6
- 238000007865 diluting Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 6
- 238000013019 agitation Methods 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000003839 salts Chemical class 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
- 239000002253 acid Substances 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
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 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 4
- 125000001931 aliphatic group Chemical group 0.000 description 3
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 229960003750 ethyl chloride Drugs 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 3
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000009257 reactivity Effects 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
- 239000000725 suspension Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 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
- 230000017105 transposition Effects 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical class P XYFCBTPGUUZFHI-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 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
- 150000005840 aryl radicals Chemical class 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
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic 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
- 239000012467 final product Substances 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 150000002390 heteroarenes Chemical class 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
- 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
- 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
- 238000004064 recycling Methods 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
- 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
- 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US454043 | 1999-12-03 | ||
| US43042602P | 2002-12-02 | 2002-12-02 | |
| US430426P | 2002-12-02 | ||
| US10/454,043 US20040106815A1 (en) | 2002-12-02 | 2003-06-04 | Selective synthesis of organophosphites |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2526971T3 true ES2526971T3 (es) | 2015-01-19 |
Family
ID=32397248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10170500.2T Expired - Lifetime ES2526971T3 (es) | 2002-12-02 | 2003-12-02 | Una síntesis selectiva de organofosfitos |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20040106815A1 (enExample) |
| EP (3) | EP2239248B2 (enExample) |
| JP (1) | JP2006508177A (enExample) |
| AT (1) | ATE501998T1 (enExample) |
| AU (1) | AU2003294564A1 (enExample) |
| CA (1) | CA2508337C (enExample) |
| DE (1) | DE60336419D1 (enExample) |
| ES (1) | ES2526971T3 (enExample) |
| WO (1) | WO2004050588A2 (enExample) |
Families Citing this family (34)
| 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 |
| FR2854892B1 (fr) * | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
| FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
| CA2644961A1 (en) * | 2006-03-17 | 2007-09-27 | Invista Technologies S.A.R.L. | Method for the purification of triorganophosphites by treatment with a basic additive |
| JP2009542766A (ja) * | 2006-07-12 | 2009-12-03 | ビーエーエスエフ ソシエタス・ヨーロピア | ハロゲンを含んだ有機リン化合物を製造する方法 |
| US7880028B2 (en) * | 2006-07-14 | 2011-02-01 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| US7709674B2 (en) * | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L | Hydrocyanation process with reduced yield losses |
| US7919646B2 (en) * | 2006-07-14 | 2011-04-05 | Invista North America S.A R.L. | Hydrocyanation of 2-pentenenitrile |
| US7709673B2 (en) * | 2006-07-14 | 2010-05-04 | 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 |
| US7977502B2 (en) * | 2008-01-15 | 2011-07-12 | Invista North America S.A 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 |
| CN101981042B (zh) * | 2008-03-28 | 2014-02-19 | 联合碳化化学品及塑料技术公司 | 用于单氯代亚磷酸酯合成的淤浆方法 |
| EP2373696A2 (en) * | 2008-12-29 | 2011-10-12 | Dow Global Technologies LLC | Catalyst composition with phosphorus-based donor |
| CN102405226A (zh) | 2009-04-21 | 2012-04-04 | 因温斯特技术公司 | 用于制备有机二亚磷酸酯的高选择性方法 |
| WO2011014405A1 (en) * | 2009-07-31 | 2011-02-03 | Chemtura Corporation | Liquid alkylated trisaryl phosphite compositions having two alkyl groups with different carbon number |
| WO2011075494A1 (en) | 2009-12-18 | 2011-06-23 | Invista Technologies S.A.R.L. | Nickel metal compositions and nickel complexes derived from basic nickel carbonates |
| WO2012033555A1 (en) | 2010-09-07 | 2012-03-15 | Invista Technologies S.A.R.L. | Nickel compositions for preparing nickel metal and nickel complexes |
| EP2718013A2 (en) | 2011-06-10 | 2014-04-16 | Invista Technologies S.à.r.l. | Nickel calcination and reduction process including a fluidizing bed reactor |
| EP2718015A2 (en) | 2011-06-10 | 2014-04-16 | Invista Technologies S.à.r.l. | Improvement in nickel metal-ligand catalyst formation |
| WO2013076569A1 (en) | 2011-10-26 | 2013-05-30 | Invista Technologies S.A R.L. | Methods for producing organodi phosphites 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 |
| US11098197B2 (en) | 2017-08-04 | 2021-08-24 | Wacker Chemie Ag | Silicone compositions crosslinkable by irradiation with UV light |
| EP4303222A4 (en) * | 2021-03-03 | 2025-06-18 | Tokyo Institute of Technology | Method for producing asymmetric phosphoric acid triester, method for producing symmetric phosphoric acid triester, method for producing phosphoric acid ester, and method for producing organophosphorus compound |
| WO2023228075A1 (en) | 2022-05-23 | 2023-11-30 | Inv Nylon Chemicals Americas, Llc | Multidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| WO2023228077A1 (en) | 2022-05-23 | 2023-11-30 | Inv Nylon Chemicals Americas, Llc | Multidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| CN119156371A (zh) | 2022-08-02 | 2024-12-17 | 英威达纺织（英国）有限公司 | 产生腈的方法和用于此类方法的含磷催化剂 |
| WO2024028718A1 (en) | 2022-08-02 | 2024-02-08 | Inv Nylon Chemicals Americas, Llc | Bidfntate phosphite ligands. catalytic compositions containing such ligands. and catalytic processes utilizing such catalytic compositions |
| CN119013248A (zh) | 2022-08-02 | 2024-11-22 | 英威达纺织（英国）有限公司 | 生产腈的方法和用于此类方法的含磷催化剂 |
| US12698299B2 (en) | 2022-08-02 | 2026-08-04 | Inv Nylon Chemicals Americas, Llc | Bidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| EP4499657A1 (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 |
| WO2024028717A1 (en) | 2022-08-02 | 2024-02-08 | Inv Nylon Chemicals Americas, Llc | Arsenic-containing ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
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 (enExample) * | 1991-06-11 | 1993-09-21 | Mitsubishi Chemicals Co Ltd | |
| IN187044B (enExample) | 1995-01-27 | 2002-01-05 | Du Pont | |
| US6031120A (en) * | 1997-07-29 | 2000-02-29 | 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 DE DE60336419T patent/DE60336419D1/de not_active Expired - Lifetime
- 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 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 AT AT03787252T patent/ATE501998T1/de not_active IP Right Cessation
- 2003-12-02 JP JP2004570997A patent/JP2006508177A/ja not_active Ceased
- 2003-12-02 AU AU2003294564A patent/AU2003294564A1/en not_active Abandoned
- 2003-12-02 WO PCT/US2003/038367 patent/WO2004050588A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP2243763B2 (en) | 2022-07-06 |
| EP1567468A4 (en) | 2008-01-23 |
| CA2508337A1 (en) | 2004-06-17 |
| AU2003294564A8 (en) | 2004-06-23 |
| CA2508337C (en) | 2013-01-29 |
| AU2003294564A1 (en) | 2004-06-23 |
| EP2243763B1 (en) | 2014-10-08 |
| EP1567468A2 (en) | 2005-08-31 |
| DE60336419D1 (de) | 2011-04-28 |
| JP2006508177A (ja) | 2006-03-09 |
| EP2239248B1 (en) | 2015-09-23 |
| ATE501998T1 (de) | 2011-04-15 |
| EP2239248B2 (en) | 2021-06-09 |
| EP2243763A2 (en) | 2010-10-27 |
| WO2004050588A3 (en) | 2004-09-23 |
| EP1567468B1 (en) | 2011-03-16 |
| WO2004050588A2 (en) | 2004-06-17 |
| EP2239248A3 (en) | 2010-12-29 |
| HK1085194A1 (zh) | 2006-08-18 |
| EP2243763A3 (en) | 2010-12-29 |
| US20040106815A1 (en) | 2004-06-03 |
| EP2239248A2 (en) | 2010-10-13 |
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