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 (enExample) |
| EP (3) | EP1567468B1 (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 (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 |
| 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 |
| US7629484B2 (en) * | 2006-03-17 | 2009-12-08 | Invista North America S.A.R.L. | Method for the purification of triorganophosphites by treatment with a basic additive |
| CN101490065B (zh) * | 2006-07-12 | 2013-06-19 | 巴斯夫欧洲公司 | 制备含卤素的有机磷化合物的方法 |
| US7919646B2 (en) | 2006-07-14 | 2011-04-05 | Invista North America S.A R.L. | Hydrocyanation of 2-pentenenitrile |
| US7659422B2 (en) * | 2006-07-14 | 2010-02-09 | Invista North America S.A.R.L. | Hydrocyanation process with reduced yield losses |
| 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 |
| US7709673B2 (en) * | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| US8088943B2 (en) * | 2008-01-15 | 2012-01-03 | Invista North America S.A R.L. | Hydrocyanation of pentenenitriles |
| 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 |
| JP5563552B2 (ja) * | 2008-03-28 | 2014-07-30 | ユニオン カーバイド ケミカルズ アンド プラスティックス テクノロジー エルエルシー | ホスホロモノクロリダイト合成のためのスラリー法 |
| MX2011007066A (es) * | 2008-12-29 | 2011-12-16 | Dow Global Technologies Llc | Composicion de catalizador con donador a base de fosforo. |
| 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 |
| 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 |
| US9024049B2 (en) | 2010-09-07 | 2015-05-05 | Invista North America S.A.R.L. | Nickel compositions for preparing nickel metal and nickel complexes |
| CN107020150B (zh) | 2011-06-10 | 2019-11-29 | 英威达纺织（英国）有限公司 | 镍金属配体催化剂形成上的改进 |
| EP2718013A2 (en) | 2011-06-10 | 2014-04-16 | Invista Technologies S.à.r.l. | Nickel calcination and reduction process including a fluidizing bed reactor |
| JP5946537B2 (ja) | 2011-10-26 | 2016-07-06 | インヴィスタ テクノロジーズ エスアエルエル | 副生成物レベルを測定してさらなる添加を決定することを特徴とする、ホスホロクロリダイトから有機ジホスファイトを作製するための方法 |
| 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 |
| JP7659787B2 (ja) * | 2021-03-03 | 2025-04-10 | 国立大学法人東京科学大学 | 非対称型リン酸トリエステルの製造方法、対称型リン酸トリエステルの製造方法、リン酸エステルの製造方法、及び、有機リン化合物の製造方法 |
| EP4499303A1 (en) | 2022-05-23 | 2025-02-05 | INVISTA Textiles (U.K.) Limited | Multidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| EP4499302A1 (en) | 2022-05-23 | 2025-02-05 | INVISTA Textiles (U.K.) Limited | Multidentate phosphite ligands, catalytic compositions containing such ligands, and catalytic processes utilizing such catalytic compositions |
| 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 |
| WO2024028722A1 (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 |
| 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 |
| CN119095857A (zh) | 2022-08-02 | 2024-12-06 | 英威达纺织（英国）有限公司 | 双齿亚磷酸酯配体、含有此类配体的催化组合物以及利用此类催化组合物的催化方法 |
| 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 |
| CN119095862A (zh) | 2022-08-02 | 2024-12-06 | 英威达纺织（英国）有限公司 | 双齿亚磷酸酯配体、含有此类配体的催化组合物以及利用此类催化组合物的催化方法 |
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| 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 | |
| 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 ES ES10170500.2T patent/ES2526971T3/es not_active Expired - Lifetime
- 2003-12-02 EP EP03787252A patent/EP1567468B1/en 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 JP JP2004570997A patent/JP2006508177A/ja not_active Ceased
- 2003-12-02 DE DE60336419T patent/DE60336419D1/de not_active Expired - Lifetime
- 2003-12-02 CA CA2508337A patent/CA2508337C/en not_active Expired - Fee Related
- 2003-12-02 AU AU2003294564A patent/AU2003294564A1/en not_active Abandoned
- 2003-12-02 AT AT03787252T patent/ATE501998T1/de not_active IP Right Cessation
- 2003-12-02 WO PCT/US2003/038367 patent/WO2004050588A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP2243763B1 (en) | 2014-10-08 |
| EP2239248B2 (en) | 2021-06-09 |
| AU2003294564A8 (en) | 2004-06-23 |
| EP1567468B1 (en) | 2011-03-16 |
| ES2526971T3 (es) | 2015-01-19 |
| WO2004050588A2 (en) | 2004-06-17 |
| CA2508337A1 (en) | 2004-06-17 |
| EP2243763B2 (en) | 2022-07-06 |
| EP2243763A3 (en) | 2010-12-29 |
| AU2003294564A1 (en) | 2004-06-23 |
| ATE501998T1 (de) | 2011-04-15 |
| JP2006508177A (ja) | 2006-03-09 |
| EP2239248A2 (en) | 2010-10-13 |
| DE60336419D1 (de) | 2011-04-28 |
| EP2239248A3 (en) | 2010-12-29 |
| HK1085194A1 (zh) | 2006-08-18 |
| WO2004050588A3 (en) | 2004-09-23 |
| EP2243763A2 (en) | 2010-10-27 |
| US20040106815A1 (en) | 2004-06-03 |
| EP1567468A4 (en) | 2008-01-23 |
| EP2239248B1 (en) | 2015-09-23 |
| EP1567468A2 (en) | 2005-08-31 |
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