WO2009112349A1 - Procédé de préparation de monoxydes de diphosphine - Google Patents
Procédé de préparation de monoxydes de diphosphine Download PDFInfo
- Publication number
- WO2009112349A1 WO2009112349A1 PCT/EP2009/052053 EP2009052053W WO2009112349A1 WO 2009112349 A1 WO2009112349 A1 WO 2009112349A1 EP 2009052053 W EP2009052053 W EP 2009052053W WO 2009112349 A1 WO2009112349 A1 WO 2009112349A1
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- Prior art keywords
- formula
- compound
- alkyl
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- aryl
- Prior art date
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- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- -1 diaryl phosphine chloride Chemical compound 0.000 abstract description 8
- 239000002904 solvent Substances 0.000 abstract description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- DAPZRBJQPPDZGH-UHFFFAOYSA-N diphenylphosphanyl(diphenyl)phosphane Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 DAPZRBJQPPDZGH-UHFFFAOYSA-N 0.000 description 8
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 5
- 239000003063 flame retardant Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YXFVVABEGXRONW-JGUCLWPXSA-N toluene-d8 Chemical compound [2H]C1=C([2H])C([2H])=C(C([2H])([2H])[2H])C([2H])=C1[2H] YXFVVABEGXRONW-JGUCLWPXSA-N 0.000 description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- JCRCPEDXAHDCAJ-UHFFFAOYSA-N ethoxy(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(OCC)C1=CC=CC=C1 JCRCPEDXAHDCAJ-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- OAADXJFIBNEPLY-UHFFFAOYSA-N methoxy(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(OC)C1=CC=CC=C1 OAADXJFIBNEPLY-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- OTYNBGDFCPCPOU-UHFFFAOYSA-N phosphane sulfane Chemical compound S.P[H] OTYNBGDFCPCPOU-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 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
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5341—Organo-phosphine oxides or thioxides containing a P-P bond
Definitions
- the object of the present invention relates to a process for the preparation of diphosphine monoxides by reaction of dialkyl- or diarylphosphine chloride with alkoxydialkyl- or diarylphosphine without solvent and subsequent removal of the product.
- TPDM 1, 2,2-Tetraphenyldiphosphinmonoxid
- diphosphines are usually carried out by coupling the corresponding halophosphine with an alkoxyphosphine with elimination and simultaneous removal of the haloalkane in an inert solvent.
- TPDM tetraphenyldiphosphine
- metals such as sodium, lithium or magnesium
- subsequent oxidation of the tetraphenyldiphosphine with air or other oxidizing agents as described by A. J Blake, G. P McQuillan, I.A. Oxton, D. Troy, J. Mol. Struct. 1982, 78, at pages 265 to 272.
- a disadvantage of this method is not only the two-step process control, but also the increased safety measures that must be made for the production of tetraphenyldiphosphine, as must be taken to handle the air-sensitive alkali metals and the handling of the air-sensitive products. Furthermore, in the coupling reaction large amounts of heat are released, which must be removed accordingly. Further disadvantages are that the oxidation proceeds only with low selectivity and in the reaction the formation of by-products such as tetraphenyldiphosphine dioxide can not be avoided.
- diphosphine monoxide Another method for preparing diphosphine monoxide is described by Inorg. Nucl. Chem. Letters 1967, Vol.3, at page 313. In this case, diphenylphosphine chloride is reacted in the presence of methoxydiphenylphosphine and benzene as the solvent.
- the procedure of the synthesis of TPDM from E-thoxydiphenylphosphine, which is accessible on an industrial scale, and diphenylch- lorphosphin according to the E. Fluck and H. Binder Inorg. Nucl. Chem. Letters 1967, Vol. 3, at page 313 showed that the resulting product has a purity of ⁇ 90% and that the crystallization does not lead to a reduction in the content of tetraphenyldiphosphine dioxide. Due to this procedure in a solvent, however, because of the dilution (about 1 M) and the low reaction rate, the space-time yield at about 6 g / L * h is low.
- the object of the present invention is therefore to provide a process which makes it possible selectively to produce diphosphine monoxides which produce less than 10% of secondary components, which allows a simplified work-up and also has an improved reaction time.
- R 1 -R 4 are independently selected from the group of C 1 -C 16 -alkyl, C 1 -C 16 -alkenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkyl-NR 2 R 3 , Cs-do -cycloalkyl, C3-C10-cycloalkoxy, C ⁇ -Cio-aryl, C ⁇ -C-io-aryloxy, C ⁇ -Cio-aryl-Ci-Ci ⁇ -alkyl, C6-Cio-aryl-Ci-Ci6- alkoxy, NR 2 R 3 , COR 2 , COOR 2 and CONR 2 R 3 comprising the step
- R 5 is selected from the group of C 2 -C 16 -alkyl, C 1 -C 16 -alkenyl, C 3 -C 10 -cycloalkyl or C ⁇ -do-aryl !.
- radicals R 1 to R 4 are phenyl groups.
- step a) is carried out at a temperature in the range from 110 to 130 ° C.
- the process according to the invention is advantageous if the separation of the compound of the formula I in step c) takes place by filtration or centrifugation.
- radicals R 1 to R 4 are independently selected from the group of C 1 -C 18 -alkyl, C 1 -C 18 -alkenyl, C 1 -C 4 -alkoxy, d-
- Preferred C 1 -C 16 -alkyl groups are methyl, ethyl, n-propyl, i-propyl, n-butyl, tert-butyl, isobutyl, hexyl, octyl, decyl, dodecyl, tetradecyl, 2-ethylhexyl and 2-methyl.
- C ⁇ -Cio-aryl groups are phenyl and naphthyl. Particularly preferred
- radicals R 1 and R 2 and R 3 and R 4 are identical. Especially preferred for R 1 and R 2 is the phenyl group and for R 3 and R 4 is the phenyl, ethyl and allyl group. Especially preferred is especially when R 1 to R 4 are phenyl groups.
- the group R 5 is selected from the group of C 2 -C 16 -alkyl, C 1 -C 16 -alkenyl, C 3 -C 10 -cycloalkyl or C 6 -C 10 -aryl.
- Preferred C2-C16 alkyl groups are selected from the group of ethyl, n-propyl, i-propyl, n-butyl, tert-butyl, i-butyl, decyl, dodecyl, tetradecyl or 2-ethylhexyl.
- the ethyl group is very particularly preferred.
- the preferred C 1 -C 16 -alkenyl group is AIIyI.
- Preferred C 3 -C 10 -cycloalkyl groups are selected from the group of cyclopentyl and cyclohexyl.
- Preferred C ⁇ -C-io-arvl groups are selected from the group of phenyl, naphthyl, ToIyI, dimethylphenyl and methoxyphenyl.
- the group R 5 is selected from the group of ethyl and
- the reaction is carried out in the presence of temperatures in the range from 50 to 180 ° C., more preferably in the range from 80 to 160 ° C., very particularly preferably in the range from 110 to 130 ° C.
- step a an excess of the compound of formula III is added to the compound of formula II.
- the ratio of compounds of the formula II to III is thus 1: 5, more preferably 1: 2.4.
- the process according to the invention can be operated both batchwise, semi-batch and continuously. Preference is given to a semi-batch or continuous procedure. Quite particularly preferred is a continuous mode of operation.
- the product R 5 Cl formed during the reaction in addition to the compound of the formula I is removed from the reaction mixture.
- the removal can be carried out by methods known to those skilled in the art, such as stripping, distillation, extraction or phase separation.
- the process procedure is preferably selected such that the R 5 Cl formed in the reaction is gaseous and is produced in such amounts that it can be distilled off safely during the reaction. This is preferably realized by a controlled addition of the compound of formula II to the compound of formula III.
- the compound of the formula I which is formed by this process is preferably precipitated as a solid. Some compounds of formula I are also oils.
- the compound of formula I is then separated from the reaction solution obtained after step b). The separation can be carried out by the methods known to those skilled in the art, such as filtration, centrifuging, extraction, distillation and sublimation.
- the product obtained by the process according to the invention may, if appropriate, be subjected to a further purification step once more.
- Possible purification steps here are recrystallization, washing of the crystallizate, followed by removal of the wash solution under reduced pressure, distillation, sublimation. Preference is given to washing the crystals under ISb or Ar atmosphere, followed by removal of the washing solution under reduced pressure. All organic solvents selected from the group of toluene, xylene, dibutyl ether, alkanes such as hexane, heptane and petroleum ether or mixtures thereof are suitable for washing the crystals.
- Example 1 (according to the invention) Ethoxydiphenylphosphine (552.6 g, 2.40 mol) is placed in a stirred flask and heated to 120 0 C internal temperature. Within 1 h chlorodiphenylphosphine (220.6 g, 1, 0mol) is added dropwise so that the resulting ethyl chloride can be safely removed. It is stirred for a further hour at reaction temperature and then cooled. The crystals are filtered off and washed with toluene. It is dried at the best possible oil pump vacuum and 100 0 C.
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)
Abstract
L'invention concerne un procédé de préparation de monoxydes de diphosphine par réaction de chlorure de dialkylphosphine ou de diarylphosphine avec une alcoxydialkylphosphine ou une alcoxydiarylphosphine sans solvant et séparation consécutive du produit.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08152559 | 2008-03-11 | ||
EP08152559.4 | 2008-03-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2009112349A1 true WO2009112349A1 (fr) | 2009-09-17 |
Family
ID=40548868
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2009/052053 WO2009112349A1 (fr) | 2008-03-11 | 2009-02-20 | Procédé de préparation de monoxydes de diphosphine |
Country Status (1)
Country | Link |
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WO (1) | WO2009112349A1 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011009876A1 (fr) * | 2009-07-24 | 2011-01-27 | Basf Se | Dérivés de diphosphines en tant quignifugeants dans des résines époxy aromatiques et/ou hétéroaromatiques |
-
2009
- 2009-02-20 WO PCT/EP2009/052053 patent/WO2009112349A1/fr active Application Filing
Non-Patent Citations (3)
Title |
---|
AL'FONSOV, V. A. ET AL: "Ligand exchange reactions in a series of phosphorus(III) derivatives. Characteristics of exchange in a series of phosphinous derivatives", J. GEN. CHEM. USSR, vol. 51, 1981, pages 8 - 15, XP008105745 * |
DEMIK, N. N. ET AL: "Synthesis of diphosphine monoxides", J. GEN. CHEM USSR, vol. 61, 1991, pages 460 - 461, XP008105746 * |
FLUCK ET AL: "Darstellung von verbindungen MIT P---P ? und P---P---P ? gerüsten", INORGANIC AND NUCLEAR CHEMISTRY LETTERS, vol. 3, no. 8, 1967, pages 307 - 313, XP002524721 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011009876A1 (fr) * | 2009-07-24 | 2011-01-27 | Basf Se | Dérivés de diphosphines en tant quignifugeants dans des résines époxy aromatiques et/ou hétéroaromatiques |
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