DE10359434A1 - Verfahren zur Herstellung von Phosphoniumsalzen - Google Patents
Verfahren zur Herstellung von Phosphoniumsalzen Download PDFInfo
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- DE10359434A1 DE10359434A1 DE10359434A DE10359434A DE10359434A1 DE 10359434 A1 DE10359434 A1 DE 10359434A1 DE 10359434 A DE10359434 A DE 10359434A DE 10359434 A DE10359434 A DE 10359434A DE 10359434 A1 DE10359434 A1 DE 10359434A1
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- Germany
- Prior art keywords
- carbon atoms
- aliphatic
- general formula
- acid
- solvent mixture
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 45
- 238000002360 preparation method Methods 0.000 title claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 38
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000011877 solvent mixture Substances 0.000 claims abstract description 32
- 239000012039 electrophile Substances 0.000 claims abstract description 18
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 24
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 19
- -1 aliphatic hydrocarbon radical Chemical class 0.000 claims description 18
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- YLONZHSUBWJZOE-UHFFFAOYSA-N [5-(4-hydroxy-2,6,6-trimethyl-3-oxocyclohexen-1-yl)-3-methylpenta-2,4-dienyl] acetate Chemical compound CC(=O)OCC=C(C)C=CC1=C(C)C(=O)C(O)CC1(C)C YLONZHSUBWJZOE-UHFFFAOYSA-N 0.000 description 1
- UDQCWRFTJTYISL-UHFFFAOYSA-N [5-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3-methylpent-2-en-4-ynyl] acetate Chemical compound CC(=O)OCC=C(C)C#CC1=C(C)CC(O)CC1(C)C UDQCWRFTJTYISL-UHFFFAOYSA-N 0.000 description 1
- HAJVACNQOSWCMQ-UHFFFAOYSA-N [5-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3-methylpenta-2,4-dienyl] acetate Chemical compound CC(=O)OCC=C(C)C=CC1=C(C)CC(O)CC1(C)C HAJVACNQOSWCMQ-UHFFFAOYSA-N 0.000 description 1
- RVPYMELITCITOC-UHFFFAOYSA-N [9-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenyl] acetate Chemical compound CC(=O)OCC=C(C)C=CC=C(C)C=CC1=C(C)CC(O)CC1(C)C RVPYMELITCITOC-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- BBMCPEOFGAIHQK-UHFFFAOYSA-N methyl 4-bromo-3-methylbut-2-enoate Chemical compound COC(=O)C=C(C)CBr BBMCPEOFGAIHQK-UHFFFAOYSA-N 0.000 description 1
- FNSGNNZYMUIWAD-UHFFFAOYSA-N methyl 4-chloro-3-methylbut-2-enoate Chemical compound COC(=O)C=C(C)CCl FNSGNNZYMUIWAD-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000004492 retinoid derivatives Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- IDXDWPWXHTXJMZ-UHFFFAOYSA-N tris(2,4,6-trimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(C)=C1P(C=1C(=CC(C)=CC=1C)C)C1=C(C)C=C(C)C=C1C IDXDWPWXHTXJMZ-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical group CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical group C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5428—Acyclic unsaturated phosphonium compounds
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5442—Aromatic phosphonium compounds (P-C aromatic linkage)
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)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10359434A DE10359434A1 (de) | 2003-12-17 | 2003-12-17 | Verfahren zur Herstellung von Phosphoniumsalzen |
| CN2004800375929A CN1894265B (zh) | 2003-12-17 | 2004-12-14 | 制备*盐的方法 |
| US10/582,912 US7547807B2 (en) | 2003-12-17 | 2004-12-14 | Method for producing phosphonium salts |
| DE502004011432T DE502004011432D1 (de) | 2003-12-17 | 2004-12-14 | Verfahren zur herstellung von phosphoniumsalzen |
| AT04820433T ATE474844T1 (de) | 2003-12-17 | 2004-12-14 | Verfahren zur herstellung von phosphoniumsalzen |
| PCT/EP2004/014207 WO2005058924A1 (de) | 2003-12-17 | 2004-12-14 | Verfahren zur herstellung von phosphoniumsalzen |
| JP2006544306A JP4659757B2 (ja) | 2003-12-17 | 2004-12-14 | ホスホニウム塩の製造方法 |
| CA002546480A CA2546480A1 (en) | 2003-12-17 | 2004-12-14 | Method for producing phosphonium salts |
| EP04820433A EP1697388B1 (de) | 2003-12-17 | 2004-12-14 | Verfahren zur herstellung von phosphoniumsalzen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10359434A DE10359434A1 (de) | 2003-12-17 | 2003-12-17 | Verfahren zur Herstellung von Phosphoniumsalzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10359434A1 true DE10359434A1 (de) | 2005-07-21 |
Family
ID=34683507
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10359434A Withdrawn DE10359434A1 (de) | 2003-12-17 | 2003-12-17 | Verfahren zur Herstellung von Phosphoniumsalzen |
| DE502004011432T Expired - Lifetime DE502004011432D1 (de) | 2003-12-17 | 2004-12-14 | Verfahren zur herstellung von phosphoniumsalzen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE502004011432T Expired - Lifetime DE502004011432D1 (de) | 2003-12-17 | 2004-12-14 | Verfahren zur herstellung von phosphoniumsalzen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7547807B2 (https=) |
| EP (1) | EP1697388B1 (https=) |
| JP (1) | JP4659757B2 (https=) |
| CN (1) | CN1894265B (https=) |
| AT (1) | ATE474844T1 (https=) |
| CA (1) | CA2546480A1 (https=) |
| DE (2) | DE10359434A1 (https=) |
| WO (1) | WO2005058924A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10359433A1 (de) * | 2003-12-17 | 2005-07-21 | Basf Ag | Verfahren zur Herstellung von Vitamin A-Acetat |
| EP2130833A1 (en) * | 2008-06-05 | 2009-12-09 | DSM IP Assets B.V. | Process for the preparation of zeacarotenes |
| JP5803031B2 (ja) * | 2010-10-01 | 2015-11-04 | ディーエスエム アイピー アセッツ ビー．ブイ． | ペレチノインの向上した合成 |
| CN103172673B (zh) * | 2011-12-26 | 2016-04-20 | 南京工业大学 | 3，7，11-三甲基十二碳-2，4，6，10-四烯-1-基膦盐的制备方法 |
| CN103288875A (zh) * | 2013-05-24 | 2013-09-11 | 广州巨元生化有限公司 | 一种维生素a磷盐的制备方法 |
| CN104478930B (zh) * | 2014-11-19 | 2016-05-25 | 上海泰坦科技股份有限公司 | 磷配体类化合物的合成工艺 |
| CN105622376B (zh) * | 2016-03-31 | 2018-10-23 | 广州巨元生化有限公司 | 一种制备阿朴-8’-番茄红素的方法 |
| CN109651150B (zh) * | 2018-12-20 | 2022-02-18 | 万华化学集团股份有限公司 | 一种制备维生素a醋酸酯的方法 |
| CN111499662B (zh) * | 2020-04-26 | 2022-12-20 | 上海新华联制药有限公司 | 一种异维a酸c15-氯化三苯基膦及其制备方法和应用 |
| CN113201016B (zh) * | 2021-05-19 | 2023-09-19 | 万华化学集团股份有限公司 | 一种c15膦盐的制备方法 |
| WO2022241670A1 (zh) * | 2021-05-19 | 2022-11-24 | 万华化学集团股份有限公司 | 一种c15膦盐的制备方法 |
| JP2025511349A (ja) * | 2022-04-12 | 2025-04-15 | エルジー エナジー ソリューション リミテッド | リチウム二次電池 |
| CN114957525B (zh) * | 2022-06-01 | 2023-08-29 | 东营市大舜化工有限责任公司 | 一种用于油田污水处理的杀菌剂及合成方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL124639C (https=) * | 1963-05-24 | |||
| DE2505869C3 (de) | 1975-02-12 | 1978-05-18 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von symmetrischen Carotinoiden |
| DE2727384A1 (de) | 1977-06-18 | 1979-01-04 | Basf Ag | Verfahren zur herstellung von waessrigen loesungen von polyenyltriarylphosphoniumsalzen |
| CA1101431A (en) * | 1977-06-18 | 1981-05-19 | Bernhard Schulz | Preparation of aqueous solutions or fine aqueous dispersions of polyenyltriarylphosphonium salts |
| DE2729974C3 (de) | 1977-07-02 | 1981-09-24 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von wäßrigen Lösungen bzw. feinteiligen wäßrigen Dispersionen von Polyenyltriarylphosphoniumsalzen |
| DE4211140A1 (de) * | 1992-04-03 | 1993-10-07 | Basf Ag | Phosphoniumsalze und ihre Verwendung als Glanzmittel für wäßrig-saure galvanische Nickelbäder |
| US5344995A (en) | 1992-07-14 | 1994-09-06 | Basf Aktiengesellschaft | Preparation of cyclic acetals of 3-formyl-2-butenyltriphenylphosphonium chloride |
| DE19517422A1 (de) * | 1995-05-12 | 1996-11-14 | Basf Ag | Verfahren zur Herstellung von beta-Carotin-Präparaten mit hohem 9(Z)-Gehalt |
-
2003
- 2003-12-17 DE DE10359434A patent/DE10359434A1/de not_active Withdrawn
-
2004
- 2004-12-14 CA CA002546480A patent/CA2546480A1/en not_active Abandoned
- 2004-12-14 CN CN2004800375929A patent/CN1894265B/zh not_active Expired - Lifetime
- 2004-12-14 WO PCT/EP2004/014207 patent/WO2005058924A1/de not_active Ceased
- 2004-12-14 US US10/582,912 patent/US7547807B2/en not_active Expired - Lifetime
- 2004-12-14 EP EP04820433A patent/EP1697388B1/de not_active Expired - Lifetime
- 2004-12-14 DE DE502004011432T patent/DE502004011432D1/de not_active Expired - Lifetime
- 2004-12-14 JP JP2006544306A patent/JP4659757B2/ja not_active Expired - Lifetime
- 2004-12-14 AT AT04820433T patent/ATE474844T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2546480A1 (en) | 2005-06-30 |
| CN1894265A (zh) | 2007-01-10 |
| JP4659757B2 (ja) | 2011-03-30 |
| WO2005058924A1 (de) | 2005-06-30 |
| ATE474844T1 (de) | 2010-08-15 |
| JP2007514679A (ja) | 2007-06-07 |
| DE502004011432D1 (de) | 2010-09-02 |
| US20070123726A1 (en) | 2007-05-31 |
| EP1697388B1 (de) | 2010-07-21 |
| EP1697388A1 (de) | 2006-09-06 |
| US7547807B2 (en) | 2009-06-16 |
| CN1894265B (zh) | 2011-12-28 |
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Legal Events
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| 8130 | Withdrawal |