JP2008512451A - ホスフィン酸アルキルの製造方法 - Google Patents
ホスフィン酸アルキルの製造方法 Download PDFInfo
- Publication number
- JP2008512451A JP2008512451A JP2007531131A JP2007531131A JP2008512451A JP 2008512451 A JP2008512451 A JP 2008512451A JP 2007531131 A JP2007531131 A JP 2007531131A JP 2007531131 A JP2007531131 A JP 2007531131A JP 2008512451 A JP2008512451 A JP 2008512451A
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- acid
- hypophosphite
- mmol
- toluene
- 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.)
- Pending
Links
- -1 alkyl phosphinate Chemical compound 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 44
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- GJYJYFHBOBUTBY-UHFFFAOYSA-N alpha-camphorene Chemical group CC(C)=CCCC(=C)C1CCC(CCC=C(C)C)=CC1 GJYJYFHBOBUTBY-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 9
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 6
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 2
- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical compound COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 claims description 2
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229910001380 potassium hypophosphite Inorganic materials 0.000 claims description 2
- CRGPNLUFHHUKCM-UHFFFAOYSA-M potassium phosphinate Chemical compound [K+].[O-]P=O CRGPNLUFHHUKCM-UHFFFAOYSA-M 0.000 claims description 2
- 229910001379 sodium hypophosphite Inorganic materials 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000002002 slurry Substances 0.000 description 13
- ZKNJRUPWSFSOFM-UHFFFAOYSA-N diethoxymethyl-ethoxy-oxophosphanium Chemical compound CCOC(OCC)[P+](=O)OCC ZKNJRUPWSFSOFM-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 238000005191 phase separation Methods 0.000 description 6
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BMWDUGHMODRTLU-UHFFFAOYSA-N azanium;trifluoromethanesulfonate Chemical compound [NH4+].[O-]S(=O)(=O)C(F)(F)F BMWDUGHMODRTLU-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- VQPHVWQKRYAXFD-UHFFFAOYSA-N methanesulfonic acid trimethoxymethane Chemical compound COC(OC)OC.CS(=O)(=O)O VQPHVWQKRYAXFD-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/4816—Acyclic saturated acids or derivatices which can have further substituents on alkyl
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0402199A SE0402199D0 (sv) | 2004-09-13 | 2004-09-13 | New process I |
| PCT/SE2005/001316 WO2006031180A1 (en) | 2004-09-13 | 2005-09-12 | Process for preparation of alkyl phosphinates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008512451A true JP2008512451A (ja) | 2008-04-24 |
| JP2008512451A5 JP2008512451A5 (enExample) | 2008-10-30 |
Family
ID=33157526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007531131A Pending JP2008512451A (ja) | 2004-09-13 | 2005-09-12 | ホスフィン酸アルキルの製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7557234B2 (enExample) |
| EP (1) | EP1791851B1 (enExample) |
| JP (1) | JP2008512451A (enExample) |
| CN (1) | CN100575355C (enExample) |
| AT (1) | ATE490259T1 (enExample) |
| DE (1) | DE602005025140D1 (enExample) |
| SE (1) | SE0402199D0 (enExample) |
| WO (1) | WO2006031180A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103755605B (zh) * | 2013-12-30 | 2016-08-17 | 中国科学院上海硅酸盐研究所 | 对己硫基苯甲醛的制备方法 |
| CN103980306B (zh) * | 2014-04-28 | 2017-02-15 | 湖南大学 | 一种以含p(o)‑oh类化合物制备次膦酸/亚膦酸/磷酸酯类化合物的方法 |
| TW201840578A (zh) * | 2017-02-22 | 2018-11-16 | 以色列商亞當阿甘公司 | 製備甲基膦酸丁基酯的方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01110693A (ja) * | 1987-09-11 | 1989-04-27 | Ciba Geigy Ag | アリファチルホスフィン酸誘導体の製造方法 |
| JPH01301687A (ja) * | 1987-12-04 | 1989-12-05 | Ciba Geigy Ag | 置換プロパンホスフィン酸化合物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040167330A1 (en) | 2001-07-17 | 2004-08-26 | Ivan Lukes | Novel chelating agents and conjugates thereof, their synthesis and use as diagnois and therapeutic agents |
| ATE422891T1 (de) * | 2004-06-25 | 2009-03-15 | Univ Sydney | Neurologisch aktive verbindungen |
-
2004
- 2004-09-13 SE SE0402199A patent/SE0402199D0/xx unknown
-
2005
- 2005-09-12 EP EP05779058A patent/EP1791851B1/en not_active Expired - Lifetime
- 2005-09-12 CN CN200580030435A patent/CN100575355C/zh not_active Expired - Fee Related
- 2005-09-12 WO PCT/SE2005/001316 patent/WO2006031180A1/en not_active Ceased
- 2005-09-12 DE DE602005025140T patent/DE602005025140D1/de not_active Expired - Lifetime
- 2005-09-12 US US11/575,082 patent/US7557234B2/en not_active Expired - Fee Related
- 2005-09-12 AT AT05779058T patent/ATE490259T1/de not_active IP Right Cessation
- 2005-09-12 JP JP2007531131A patent/JP2008512451A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01110693A (ja) * | 1987-09-11 | 1989-04-27 | Ciba Geigy Ag | アリファチルホスフィン酸誘導体の製造方法 |
| JPH01301687A (ja) * | 1987-12-04 | 1989-12-05 | Ciba Geigy Ag | 置換プロパンホスフィン酸化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1791851B1 (en) | 2010-12-01 |
| ATE490259T1 (de) | 2010-12-15 |
| CN100575355C (zh) | 2009-12-30 |
| EP1791851A4 (en) | 2010-03-10 |
| SE0402199D0 (sv) | 2004-09-13 |
| WO2006031180A1 (en) | 2006-03-23 |
| EP1791851A1 (en) | 2007-06-06 |
| US7557234B2 (en) | 2009-07-07 |
| DE602005025140D1 (de) | 2011-01-13 |
| US20080319231A1 (en) | 2008-12-25 |
| CN101018794A (zh) | 2007-08-15 |
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