EP1597220A2 - Phosphazeniumsalz-mischungen enthaltend hexakis(amino)diphosphazenium, tetrakis(amino)-phosphonium und polyaminophospazenium-salze - Google Patents

Phosphazeniumsalz-mischungen enthaltend hexakis(amino)diphosphazenium, tetrakis(amino)-phosphonium und polyaminophospazenium-salze

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Publication number
EP1597220A2
EP1597220A2 EP04709990A EP04709990A EP1597220A2 EP 1597220 A2 EP1597220 A2 EP 1597220A2 EP 04709990 A EP04709990 A EP 04709990A EP 04709990 A EP04709990 A EP 04709990A EP 1597220 A2 EP1597220 A2 EP 1597220A2
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
reaction
formula
compound
mixtures
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.)
Withdrawn
Application number
EP04709990A
Other languages
German (de)
English (en)
French (fr)
Inventor
Thomas Wessel
Daniel Decker
Thomas Sommer
Hagen HÜNIG
Reinhard Schwesinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant Produkte Deutschland GmbH
Clariant GmbH
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Filing date
Publication date
Application filed by Clariant Produkte Deutschland GmbH, Clariant GmbH filed Critical Clariant Produkte Deutschland GmbH
Publication of EP1597220A2 publication Critical patent/EP1597220A2/de
Withdrawn legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0255—Phosphorus containing compounds
    • B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
    • B01J31/0268—Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0239—Quaternary ammonium compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0255—Phosphorus containing compounds
    • B01J31/0264—Phosphorus acid amides
    • B01J31/0265—Phosphazenes, oligomers thereof or the corresponding phosphazenium salts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B39/00—Halogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
    • C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
    • C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
    • 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/59—Hydrogenated pyridine rings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions

Definitions

  • the present invention relates to aminophosphazenium salt mixtures, a process for their preparation and their use as catalysts for phase transfer reactions, nucleophilic substitution reactions or halogen-fluorine exchange reactions.
  • the variant described relates to the synthesis of hexakis (dimethylamino) diphosphazenium tetrafluoroborate (Angew. Chem. 103 (1991), 1376 or Angew. Chem. 104 (1992), 864) and includes the reaction of phosphorus pentachloride with ammonium chloride and subsequent reaction with dimethylamine and sodium tetrafluoroborate in nitromethane (CH 3 NO 2 ) or phosphorus oxychloride (POCI 3 ).
  • the higher homologous polyaminophosphazenium salts are produced via multi-stage syntheses (cf. R. Schwesinger et al., Liebigs Ann. 1996, 1055-1081), for example by converting from phosphorus pentachloride with a secondary amine, adding ammonia and subsequent treatment with Potassium methylate in methanol first synthesized an iminotrisaminophosphorane and then reacted it with an alkyliminophosphorus trichloride, which was previously prepared from the corresponding alkylammonium chloride with a mixture of PCI 5 and PCI 3 .
  • the object is achieved by a process for the preparation of aminophosphazenium mixtures which contain 5 to 99.5% by weight, in particular 10 to 95% by weight, preferably 20 to 80% by weight of a compound of the formula (I) 95 to 0.5% by weight, in particular 90 to 5% by weight, preferably 80 to 20% by weight of a compound of the formula (II) and at most 10% by weight, preferably at most 8% by weight, particularly preferably contain at most 5% by weight of one or more compounds of the general formula (III a),
  • a 1 to A 32 are, independently of one another, the same or different, and are a straight-chain or branched alkyl or alkenyl having 1 to 12 carbon atoms, cycloalkyl having 4-8 carbon atoms, an aryl having 6 to 12 carbon atoms Aralkyl having 7-12 carbon atoms, or A 1 -A 2 , A 3 -A 4 , A 5 -A 6 etc.
  • a 31 - A 32 are independently of one another, identical or different and directly or via O or NA 33 with one another are connected to a ring having 3 to 7 ring members and
  • a 33 represents an alkyl having 1 to 4 carbon atoms, where Xi and / or X 2 and / or X 3 independently of one another are radicals of the formula (III b), or the radicals Xi and / or X 2 and / or X 3 also represent a straight-chain or branched alkyl or alkenyl having 1 to 12 carbon atoms, cycloalkyl having 4 to 8 carbon atoms, an aryl having 6 to 12 carbon atoms, an aralkyl having 7 to 12 carbon atoms, or in each case the radicals which are located on an identically bound nitrogen atom, for example A 1 and A 2 , A 3 and A 4 ,
  • a 5 and A 6 etc. to A 31 and A 32 are independently of one another, identical or different and are bonded to one another directly or via O or NA 33 to form a ring having 3 to 7 ring members,
  • a 33 for an alkyl having 1 to 4 carbon atoms and B "represents a monovalent organic or inorganic acid residue or the equivalent of a polyvalent acid residue,
  • a phosphorus pentahalide is first reacted with ammonia or an ammonium halide in an inert solvent with removal of hydrogen halide and then with one or more amines of the general formula HNA 1 A 2 , HNA 3 A 4 , etc. to HNA 31 A 32 , in which A 1 to A 32 means the above-mentioned radicals are reacted, the reaction product obtained is adjusted to pH 7 to 15 with aqueous alkali, the organic and aqueous phases are separated and the organic phase is concentrated by distillation or the reaction product is isolated as a solid by completely removing the solvent becomes.
  • the present invention further relates to the mixtures themselves and their use as catalysts and co-catalysts for phase transfer reactions, nucleophilic substitution reactions or halogen-fluorine exchange reactions.
  • phosphorus pentahalide (PHal 5 ) with ammonia or a Implemented ammonium halide, the ratio PHals to ammonia or ammonium halide being 0.5: 1 to 5: 1.
  • the reaction is carried out at a temperature around the range of 25 ° C to 200 ° C in an inert solvent with removal of hydrogen halide.
  • the reaction mixture obtained is then in a second reaction step with one or more amines of the general formula HNA 1 A 2 , HNA 3 A 4 , etc.
  • HNA 31 A 32 in which A 1 to A 32 are the radicals mentioned above, in a ratio of 6 : 1 to 50: 1, based on the phosphorus pentahalide reacted at -20 to 200 ° C, the reaction product obtained at 0 to 80 ° C with aqueous alkali to a pH of 7 to 15, the organic and the aqueous Phase separated and the organic phase concentrated by distillation.
  • the product obtained is used directly as a solution or isolated as a solid by completely distilling off the solvent. If desired, the composition of the reaction product can be changed with respect to the individual components by recrystallization.
  • the primary reaction product is a dispersion of various intermediates, to which the amine is usually metered in.
  • the reverse order of addition is also possible.
  • the ratio of the individual phosphazene structures can be determined by choosing the ratio of phosphorus pentahalide to ammonia or ammonium halide. A low ratio leads to an increased proportion of the components of the formulas purple in the product mixture. Height
  • the reaction product is treated at 0 to 80 ° C. with aqueous alkali.
  • the lye is used in such amounts that a pH of 7 to 15 is maintained during the treatment.
  • hydrolyzable constituents of the reaction product are released and the amine used in excess is released from the hydrohalides of the amine formed during the reaction.
  • the recovered amine can be used again in the reaction.
  • the aqueous phase is separated from the organic phase, which contains the desired reaction product, the solvent, excess and the amine liberated from the hydrohalides of the amine.
  • the organic phase is then concentrated, e.g. by vacuum distillation and uses the residue directly or completely distills off the solvent and isolates the product as a solid. Precipitation with a second solvent and filtering the precipitate gives a product that is different
  • Product composition has as a product which is obtained by completely distilling off the solvent.
  • the solvent used for the precipitation is used in an amount of 500 to 5% by weight. If desired, the ratio of the individual components I, II and purple in the mixtures can be changed by recrystallizing the reaction product with a further solvent.
  • the reaction of the phosphorus pentahalide with ammonia or the ammonium halide is carried out at 25 ° C. to 200 ° C., preferably at 50 to 150 ° C., the hydrogen halide formed being removed during the reaction.
  • the halides used are preferably phosphorus pentachloride, phosphorus pentabromide, ammonium chloride and ammonium bromide. It is also possible to produce the phosphorus pentahalide in a preceding reaction step from the corresponding phosphorus trihalide with the halogen.
  • the phosphorus pentahalide is reacted with ammonia or the ammonium halide in a ratio of 0.5: 1 to 5: 1, in particular 1: 1 to 4: 1, preferably 1.5: 1 to 3: 1.
  • the inert solvent used is phosphorus oxychloride (POCI 3 ), an aliphatic, cycloaliphatic or aromatic hydrocarbon or a single or multiply chlorinated aliphatic, cycloaliphatic or aromatic hydrocarbon.
  • Suitable as solvents are, for example, phosphorus oxychloride, methylcyclohexane, heptane, octane, toluene, ethylbenzene, mesitylene, o-xylene, m-xylene, p-xylene, industrial mixtures of isomeric xylenes, tetrachloroethane, chlorobenzene, chlorotoluene, dichlorobenzene, dichlorotoluene, especially POCl 3 , Toluene, chlorobenzene and dichlorobenzene. Mixtures of solvents can also be used.
  • the implementation of the reaction product is, for example, phosphorus oxychloride, methylcyclohexane, heptane, octane, toluene, ethylbenzene, mesitylene, o-xylene, m-xylene, p-x
  • Phosphorus penta-halide with ammonia or ammonium halide with the amine or amines, the solvents mentioned above are suitable with the exception of phosphorus oxychloride, which is not stable under these conditions.
  • the hydrogen halide formed during the reaction is continuously removed by letting it escape from the apparatus, supporting the removal of the hydrogen halide through the apparatus with an inert gas stream or by applying a slight vacuum.
  • reaction product with the amine is reacted in a ratio of 6: 1 to 50: 1, in particular 7: 1 to 30: 1, preferably 8: 1 to 25: 1, based on the phosphorus pentahalide used ,
  • the amine is added and the reaction is continued at from -20 to 200 ° C., in particular at 0 to 180 ° C., preferably at 20 to 160 ° C.
  • the reaction is usually operated without pressure, but the reaction can take place under
  • Pressure are carried out so that solvents can be used whose boiling point is below the temperature range mentioned above.
  • the reaction product is treated at 0 to 80 ° C., in particular 10 to 70 ° C., preferably 25 to 50 ° C., with aqueous alkali, so that a pH of 7 to 15, in particular of 8 to 14.5, preferably 9 to 14.
  • aqueous alkali so that a pH of 7 to 15, in particular of 8 to 14.5, preferably 9 to 14.
  • Suitable aqueous lye is, for example, 5 to 50, in particular 15 to 30, preferably 20 to 25% by weight alkali metal or alkaline earth metal hydroxide solution. It is particularly easy to use an appropriate aqueous NaOH or KOH solution.
  • the aqueous phase is separated from the organic phase.
  • the mixtures of the compounds of the formulas I, II and lilac are in the organic phase.
  • R 1 is an alkyl radical having 1 to 9 carbon atoms, a phenyl radical, benzyl radical or naphthyl radical, R 2 -SO 3 ", wherein R 2 is an alkyl radical having 1 to 18 carbon atoms, a phenyl radical, tolyl radical or naphthyl radical, HCO 3" "A CO3 2” , AC 6 H 4 (COO " ) 2, CN “ , R 1 O " , where R 1 has the meaning given above.
  • B “ in particular means F “ , CI “ , Br “ , J “ , BF 4 “ , PF 6 “ or ⁇ SO 2” , preferably F ' , CI “ , Br “ for use as Halex catalysts.
  • the invention further relates to the use of the abovementioned mixtures, which contain the compounds of the formulas I, II and lilac, as catalysts or cocatalysts for phase transfer reactions, nucleophilic substitutions or halex reactions, in particular for phase transfer reactions and halex reactions, preferably for halex reactions.
  • the mixture is then cooled to 20 ° C. and 1920 g (22.5 mol) of piperidine are metered in with cooling so that the internal temperature does not exceed 50 ° C.
  • the mixture is heated to reflux and followed for 22 hours.
  • the mixture is cooled to 40 ° C. and 700 g of a 20% strength aqueous sodium hydroxide solution are added.
  • the organic phase is separated off and evaporated to dryness on a rotary evaporator.
  • Piperidine is redistilled from the distillate and used again.
  • the isolated solid is dried and examined by 31 P NMR spectroscopy.
  • the mixture consists of 1, 1, 1, 3,3,3-hexakis (piperidino) diphosphazenium chloride (P 2 PipCI) and tetrakis (piperidino) phosphonium chloride (PiPipCI) in a ratio of 1: 8.
  • Example 3 1000 ml of POCI 3 are placed in a 41 flat-bottomed flask under argon and 208.3 g (1 mol) of PCI 5 and 17.65 g (0.33 mol) of NH 4 CI are introduced in succession. The reaction mixture is slowly heated to reflux and stirred until the evolution of gas has ended. The hydrogen chloride released during the reaction is continuously removed via an exhaust pipe. The POCI3 used is then distilled off as completely as possible and replaced by 2000 ml of chlorobenzene. The reaction mixture is cooled to 20 ° C., 1277 g (15 mol) of piperidine are added while cooling with ice and the mixture is stirred at 40 ° C. for 4.5 days.
  • Tetrakis (piperidino) phosphonium chloride 92.1 g of potassium fluoride (1.57 mol) and 39.5 g of chlorobenzene were added.
  • the reaction mixture is dried azeotropically by distillation at reduced pressure. Then bring to 190 ° C and Held for 24 hours. Gas chromatographic analysis of the reaction mixture shows 24.6% 2-chloro-6-fluorobenzaldehyde and 75.2% 2,6-difluorobenzaldehyde.
  • Comparative Example 4a Preparation of 2,6-difluorobenzaldehyde from 2-chloro-6-fluorobenzaldehyde by means of a chlorine-fluorine exchange reaction using tetrakis (piperidino) phosphonium chloride (PiPipCI) or 1, 1, 1, 3,3,3-hexakis (piperidino) diphosphazenium chloride (P 2 PipCI) as catalyst:
  • DCTFPy CTFPy PFPy 11 mmol of catalyst 38.3 g of potassium fluoride (0.66 mol) and 50 g of chlorobenzene are successively added to 135 g of molten sulfolane.
  • the reaction mixture is dried azeotropically by distillation at reduced pressure.
  • 44.4 g of 3,5-dichloro-2,4,6-trifluoropyridine are added and the mixture is heated to 190 ° C. in a closed stirred autoclave and held for 24 hours in this reaction.
  • the reaction mixture is analyzed by gas chromatography. The following sales were obtained

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
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  • Life Sciences & Earth Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
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  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP04709990A 2003-02-21 2004-02-11 Phosphazeniumsalz-mischungen enthaltend hexakis(amino)diphosphazenium, tetrakis(amino)-phosphonium und polyaminophospazenium-salze Withdrawn EP1597220A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10307558A DE10307558A1 (de) 2003-02-21 2003-02-21 Phosphazeniumsalz-Mischungen enthaltend Hexakis(amino)diphosphazenium Tetrakis(amino)-phosphonium und Polyaminophosphazenium-Salze
DE10307558 2003-02-21
PCT/EP2004/001253 WO2004074296A2 (de) 2003-02-21 2004-02-11 Phosphazeniumsalz-mischungen enthaltend hexakis(amino)diphosphazenium, tetrakis(amino)-phosphonium und polyaminophospazenium-salze

Publications (1)

Publication Number Publication Date
EP1597220A2 true EP1597220A2 (de) 2005-11-23

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EP04709990A Withdrawn EP1597220A2 (de) 2003-02-21 2004-02-11 Phosphazeniumsalz-mischungen enthaltend hexakis(amino)diphosphazenium, tetrakis(amino)-phosphonium und polyaminophospazenium-salze

Country Status (5)

Country Link
US (1) US20060241300A1 (ja)
EP (1) EP1597220A2 (ja)
JP (1) JP2006518273A (ja)
DE (1) DE10307558A1 (ja)
WO (1) WO2004074296A2 (ja)

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Publication number Priority date Publication date Assignee Title
US20060069291A1 (en) * 2004-09-24 2006-03-30 General Electric Company Phosphazenium salt phase transfer catalysts
HUE039602T2 (hu) * 2014-02-18 2019-01-28 Covestro Deutschland Ag Eljárás izocianátok módosítására N-P-N-szekvenciájú katalizátorok alkalmazásával

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US5824827A (en) * 1996-11-22 1998-10-20 Albemarle Corporation Halogen exchange reactions
US6322502B1 (en) * 1996-12-30 2001-11-27 Imd Soft Ltd. Medical information system
DE19702282C2 (de) * 1997-01-23 1998-11-19 Hoechst Ag Katalysator für Halex-Reaktionen
EP1064323B1 (en) * 1998-03-16 2005-03-02 Dow Global Technologies Inc. Method of preparing polyolefin nanocomposites
DE19934595A1 (de) * 1999-07-23 2001-01-25 Clariant Gmbh Neue Aminophosphoniumverbindungen
DE19934594A1 (de) * 1999-07-23 2001-01-25 Clariant Gmbh Tetrakis(pyrrolidino/piperidino) phosphoniumsalze enthaltende Mischungen
TWI295986B (ja) * 2000-04-20 2008-04-21 Mitsui Chemicals Inc
JP3370972B2 (ja) * 2000-06-20 2003-01-27 川崎重工業株式会社 流動層セメントクリンカ焼成装置における気密排出装置
DE10129057A1 (de) * 2001-06-15 2002-12-19 Bayer Ag Verbessertes Verfahren zur Herstellung kernfluorierter Aromaten

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Title
See references of WO2004074296A2 *

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WO2004074296A2 (de) 2004-09-02
DE10307558A1 (de) 2004-09-02
JP2006518273A (ja) 2006-08-10
US20060241300A1 (en) 2006-10-26

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