HU204279B - Process for producing phosphine derivatives - Google Patents
Process for producing phosphine derivatives Download PDFInfo
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- HU204279B HU204279B HU908099A HU809987A HU204279B HU 204279 B HU204279 B HU 204279B HU 908099 A HU908099 A HU 908099A HU 809987 A HU809987 A HU 809987A HU 204279 B HU204279 B HU 204279B
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- 238000000034 method Methods 0.000 title claims description 12
- 150000003003 phosphines Chemical class 0.000 title description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 8
- -1 magnesium halide Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 6
- 239000003054 catalyst Substances 0.000 abstract description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 2
- 239000011574 phosphorus Substances 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 2
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 150000002941 palladium compounds Chemical class 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000003747 Grignard reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HTDQSWDEWGSAMN-UHFFFAOYSA-N 1-bromo-2-methoxybenzene Chemical compound COC1=CC=CC=C1Br HTDQSWDEWGSAMN-UHFFFAOYSA-N 0.000 description 2
- VPJKUEQDABDUJU-UHFFFAOYSA-N 3-bis(2,4-dimethoxyphenyl)phosphanylpropyl-bis(2,4-dimethoxyphenyl)phosphane Chemical compound COC1=CC(OC)=CC=C1P(C=1C(=CC(OC)=CC=1)OC)CCCP(C=1C(=CC(OC)=CC=1)OC)C1=CC=C(OC)C=C1OC VPJKUEQDABDUJU-UHFFFAOYSA-N 0.000 description 2
- SXXPTCXIFIOPQF-UHFFFAOYSA-N 3-bis(2-methoxyphenyl)phosphanylpropyl-bis(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)CCCP(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC SXXPTCXIFIOPQF-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910001868 water Inorganic materials 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- NIUZVSQOXJIHBL-UHFFFAOYSA-N 1-bromo-2,4-dimethoxybenzene Chemical compound COC1=CC=C(Br)C(OC)=C1 NIUZVSQOXJIHBL-UHFFFAOYSA-N 0.000 description 1
- RJQXUDISZWMFQR-UHFFFAOYSA-N 3-bis(2,4,6-trimethoxyphenyl)phosphanylpropyl-bis(2,4,6-trimethoxyphenyl)phosphane Chemical compound COC1=CC(OC)=CC(OC)=C1P(C=1C(=CC(OC)=CC=1OC)OC)CCCP(C=1C(=CC(OC)=CC=1OC)OC)C1=C(OC)C=C(OC)C=C1OC RJQXUDISZWMFQR-UHFFFAOYSA-N 0.000 description 1
- WUXOLZRWJZLXBJ-UHFFFAOYSA-N 3-bis(2,6-dimethoxyphenyl)phosphanylpropyl-bis(2,6-dimethoxyphenyl)phosphane Chemical compound COC1=CC=CC(OC)=C1P(C=1C(=CC=CC=1OC)OC)CCCP(C=1C(=CC=CC=1OC)OC)C1=C(OC)C=CC=C1OC WUXOLZRWJZLXBJ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000004792 aryl magnesium halides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- KIUIKWRHWKNTBP-UHFFFAOYSA-N dichloro(3-dichlorophosphanylpropyl)phosphane Chemical compound ClP(Cl)CCCP(Cl)Cl KIUIKWRHWKNTBP-UHFFFAOYSA-N 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- ZKCZXVODRKOWIY-UHFFFAOYSA-N diphenylstannane Chemical compound C=1C=CC=CC=1[SnH2]C1=CC=CC=C1 ZKCZXVODRKOWIY-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
-
- 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
-
- 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
- B01J31/0201—Oxygen-containing compounds
- B01J31/0205—Oxygen-containing compounds comprising carbonyl groups or oxygen-containing derivatives, e.g. acetals, ketals, cyclic peroxides
- B01J31/0208—Ketones or ketals
-
- 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
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
-
- 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
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- 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
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
-
- 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
-
- 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
- C07F9/5027—Polyphosphines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
- C08G67/02—Copolymers of carbon monoxide and aliphatic unsaturated compounds
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- 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
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
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- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
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- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Description
A találmány tárgya eljárás új biszfoszfin-számazékok előállítására, amelyek olefinek és szén-monoxid kopolimerizálási eljárásában alkalmazott katalizátorkészítmény komponenseként használhatók.
A találmány szerinti eljárás közelebbről az RP(Ri)2]z (I) általános képletú vegyületek - a képletben
R jelentése alkilén összekötő csoport, amely a hídban 3 szénatomot tartalmaz, és
Rt jelentése fenilcsoport, amely legalább egy 1-4 szénatomos alkoxicsoport-szubsztituenst tartalmaz a foszforatomhoz képest ortohelyzetben előállítására vonatkozik.
A fenti (I) általános képletú vegyületek a HU 202
772 lajstromszámú magyar szabadalmi leírásban ismertetett katalizátorkészítmények komponenseként használhatók olefinek és szén-monoxid kopolimerizálására.
Előnyösek azok az (I) általános képletű vegyületek, amelyek képletében az Rí jelentésére megadott fenilcsoport 1-4 szénatomos alkoxicsoport-szubsztituense metilcsoportot jelent. A fenilcsoport a foszforatomhoz képest ortohelyzetben lévő 1-4 szénatomos alkoxicsoporton kívül további 1-4 szénatomos alkoxicsoportszubsztituenseket is tartalmazhat, amelyek az ortohelyzetben lévő szubsztituenssel azonosak, vagy attól eltérőek lehetnek.
A katalizátorkészítmények komponenseként igen előnyösek az alábbi (I) általános képletű biszfoszfínok:
1.3- bisz[di(2-metoxi-fenil)-foszfíno]-propán,
1.3- bisz[di(2,4-dimetoxi-fenil)-foszfíno]-propán,
1.3- bisz[di(2,6-dimetoxi-fenil)-foszfíno]-propánés
1.3- bisz[di(2,4,6-trimetoxi-fenil)-foszfino]-propán.
Az R[P(Ri)2]a általános képletű foszfinok előállítása egy R(PX2)tt általános képletű dihalogén- foszfin és egy í RíMgY általános képletű megnézrum-halogenid reagáltatásával - a képletekben
R jelentése kétértékű alkiléncsoport,
Rí jelentése finilcsoport, amely legalább egy 1-4 szénatomos alkoxicsoport-szubsztituenst tartalmaz a i foszforatomhoz képest ortohelyzetben,
X és Y jelentése azonos vagy eltérő halogénatom, és n értéke 2 a szakirodalomból ismert (Houben-Weyl, „Methoden dér otganischen Chemie, 12/1 kötet, 34-38. oldal, 1963). z Az (I) általános képletű új vegyületeket a diaril-alkil-foszfinok előállítására alkalmas eljárásokkal állíthatjuk elő, például úgy, hogy egy bisz(dihalogén-foszfíno)-alkánt egy arü-magnézium-halogeniddel reagáltatunk, a Grignard-reakció feltételei között. 5
Szakember számára nyilvánvaló, hogy a Grignardreakciót oxigén, víz és szén-dioxid kizárásával kell végrehajtani. A Grignard-reakciőt általában éteroldőszerben játszatjuk le, például dietil-éterben vagy tetrahidrofuránban. Az aril-megnézium-halogenidet (Grig- 5 nard-vegyületet) rendszerint frissen állítjuk elő, magnézium-forgácsból és a megfelelő magnézium-halogenidből, éteroldószerben, a Grignard-reagens képződését elősegíthetjük kis mennyiségű dibrom- vagy dijődalkán hozzáadásával. 6l
A találmány szerinti eljárás kiindulási vegyületeként használt bisz(dihalogén-foszfino)-alkánokat például az alábbi reakcióvázlat szerinti eljárással állíthatjuk elő:
R(Hai)2 -4 RffO(OC2H5)2]2 -> R(PH2)2 -> R(PX2)2 5 A fenti eljárás szerint dihalogén-alkánt trietil-foszfinnal reagáltatunk, a kapott alkilén-bisz(dietil-foszfonát)-ot difenü-ón-hidriddel redukáljuk, és az így kapott difoszfino-alkánt egy COX2 általános képletű vegyülettel - például foszgénnel - reagáltatva bisz(dihalo10 gén-foszfino)-alkánná alakítjuk.
A találmány szerinti eljárást közelebbről az alábbi példákkal kívánjuk - a korlátozás szándéka nélkül ismertetni.
1. példa
A reakciókat és a termék izolálását nitrogénatmoszférában hajtjuk végre. A dietil-étert nitrogénatmoszférában, Iítium-alummium-hidridről desztillálva szántjuk. Az összes többi reaktánst használat előtt gázmen) tesítjük.
4,7 g (0,193 mól) magnézium-forgácshoz lassan, keverés közben, szobahőmérsékleten hozzáadjuk 30,71 g (0,164 mól) 2-brőm-anizol 250 ml dietil-éterrel készült oldatát. A Grignard-reagens képződésének iniciálására 2 i csepp 1,2-dibróm-etánt adunk az elegyhez, és enyhén melegítjük. A beadagolás befejezése után a reakcióelegyet 1 órán keresztül visszafolyató hűtő alatt forraljuk. A Grignard-reagens-oldatot szúrjuk és keverés közben, cseppenként hozzáadjuk 6,10 g (24,8 mmól) 1,3bisz(diklőr-foszfino)-propán 300 ml dietil-éteirel készük, -30 - -20 °C-ra hűtött oldatához, A reakcióelegyet ezután 25 ’C-ra melegítjük, és ezen a hőmérsékleten 16 órán keresztül keveq'ük. A reakcióelegyet ezután további két órán keresztül visszafolyató hűtő alatt forraljuk, majd szobahőmérsékletre hűtjük. Jeges fürdőn való hűtés közben a reakcióelegyhez cseppenként 300 ml telített, vizes ammónium-klorid-oldatot adunk. Akapott elegyet 2 órán keresztül keveq'ük. A dietil-éter egy részét desztillálással eltávolítjuk. A maradékhoz 200 ml vizet adunk és a kapott szuszpenziót három részre osztott 700 ml kloroformmal extraháljuk. Az egyesített kloroformos oldatokat ezután desztilláljuk, és a kloroform nyomait vákuumban eltávolítjuk. A kapott viszkózus olajat etanolból kristályosítjuk.
5,93 g (11,1 mól, 45%) l,3-bisz[di(2-metoxi-fenil)foszfíno]-propánt kapunk, olvadáspontja etanolból végzett átkristályosítás után: 151-152 ’C.
31P-NMR-spektrumában (deutero-klorofonnban) a kémiai eltolódás -37,9 ppm. Tömegspektrometriás analízise a várt törzsiont és fragmentumokat mutatja.
2. példa
Az 1. példában leírtak szerint járunk el, azzal az eltéréssel, hogy 2-bróm-anizol helyett l-bróm-2,4-dimetoxi-benzolt használunk.
l,3-bisz[di(2,4-dimetoxi-fenü)-foszfino]-propánt kapunk, a hozam 23%. Kémiai eltolódás 31P-NMRspektrumban (deutero- kloroformban): -38,9 ppm. Tőmegspektrometriás analízise a várt törzsíont és fragmentumokat mutatja.
Claims (5)
- SZABADALMI IGÉNYPONTOK1. Eljárás azR[P(Ri)2h (D általános képletű biszfoszfin-származékok - a képletbenR jelentése alkilén összekötő csoport, amely a hídban 3 szénatomot tartalmaz, ésRí jelentése fenilcsoport, amely legalább egy 1-4 szénatomos alkoxicsoport szubsztituenst tartalmaz a foszforatomhoz képest ortohelyzetben előállítására, azzal jellemezve, hogy egy R(PX2)2 általános képletű dihalogén-foszfint egy RíMgY általános képletű magnézium-halogeniddel - a képletekben R és Rí jelentése a tárgyi körben megadott és X és Y jelentése egymástól függetlenül halogénatom reagáltatunk.
- 2. Az 1. igénypont szerinti eljárás olyan (I) általános képletű vegyületek előállítására, amelyek képletében az 1-4 szénatomos alkoxicsoport metoxicsoportot jelent, azzal jellemezve, hogy a megfelelő kiindulási vegyületeket használjuk.
- 3. Az 1. vagy 2. igénypont szerinti eljárás olyan (I) általános képletű vegyületek előállítására, amelyek képletébenRí jelentése 2-metoxi-fenil- vagy 2,4-dimetoxi-fenilcsoport, azzal jellemezve, hogy a megfelelő kiindulási vegyületeket használjuk.
- 4. Az 1-3. igénypontok bármelyike szerinti eljárás, azzal jellemezve, hogy a reagáltatást éteroldószerben, -40 és 60 °C közötti hőmérsékleten végezzük.
- 5. A 4. igénypont szerinti eljárás, azzal jellemezve, hogy oldószerként dietil-étert használunk, és a reagáltatást -30 és 40 °C közötti hőmérsékleten végezzük.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8602164A NL8602164A (nl) | 1986-08-26 | 1986-08-26 | Katalysatorcomposities. |
| NL8602163A NL8602163A (nl) | 1986-08-26 | 1986-08-26 | Nieuwe bisfosfinen. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HU908099D0 HU908099D0 (en) | 1991-06-28 |
| HU204279B true HU204279B (en) | 1991-12-30 |
Family
ID=26646152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU908099A HU204279B (en) | 1986-08-26 | 1987-05-13 | Process for producing phosphine derivatives |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0257663B1 (hu) |
| JP (2) | JPH0822914B2 (hu) |
| KR (1) | KR960010252B1 (hu) |
| CN (1) | CN1012438B (hu) |
| AT (1) | ATE71639T1 (hu) |
| AU (1) | AU597360B2 (hu) |
| BR (1) | BR8702449A (hu) |
| CA (1) | CA1333810C (hu) |
| DE (1) | DE3776033D1 (hu) |
| DK (1) | DK233887A (hu) |
| ES (1) | ES2028048T3 (hu) |
| FI (1) | FI90557C (hu) |
| GR (1) | GR3004209T3 (hu) |
| HU (1) | HU204279B (hu) |
| IE (1) | IE60429B1 (hu) |
| IL (1) | IL82449A (hu) |
| IN (1) | IN171627B (hu) |
| NO (1) | NO169235C (hu) |
| NZ (1) | NZ220290A (hu) |
| PL (1) | PL151697B1 (hu) |
Families Citing this family (101)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1331201C (en) * | 1987-04-08 | 1994-08-02 | Johannes Adrianus Van Doorn | Preparation of substituted diaryl phosphides |
| NL8701799A (nl) * | 1987-07-30 | 1989-02-16 | Shell Int Research | Bereiding van polymeren. |
| AU612173B2 (en) * | 1987-08-28 | 1991-07-04 | Shell Internationale Research Maatschappij B.V. | Preparation of olefin/CO copolymers |
| US5227420A (en) * | 1987-09-04 | 1993-07-13 | Shell Oil Company | Polyketone compositions |
| NL8702317A (nl) * | 1987-09-29 | 1989-04-17 | Shell Int Research | Katalysatorcomposities. |
| EP0315266B1 (en) * | 1987-11-02 | 1994-01-26 | Shell Internationale Researchmaatschappij B.V. | Polyketone polymers |
| CA1329858C (en) * | 1987-11-04 | 1994-05-24 | Eit Drent | Preparation of polymers of carbon monoxide |
| CA1330132C (en) * | 1987-11-12 | 1994-06-07 | Eit Drent | Polyketone polymers |
| EP0319083A3 (en) * | 1987-11-30 | 1990-11-07 | Shell Internationale Researchmaatschappij B.V. | Polyketone polymer preparation |
| US4916208A (en) * | 1987-12-18 | 1990-04-10 | Shell Oil Company | Novel polymers |
| GB8827400D0 (en) * | 1988-11-25 | 1988-12-29 | Shell Int Research | Process for preparation of reinforced thermoplastic composites |
| GB8801756D0 (en) * | 1988-01-27 | 1988-02-24 | Shell Int Research | Copolymer composition |
| GB8804726D0 (en) * | 1988-02-29 | 1988-03-30 | Shell Int Research | Thermostabilized copolymer composition |
| US5229445A (en) * | 1988-02-10 | 1993-07-20 | Shell Oil Company | Stabilized olefin/carbon monoxide copolymers |
| CA1338576C (en) * | 1988-02-10 | 1996-09-03 | Maarten Marinus Geuze | Polyketone polymer preparation |
| US4929701A (en) * | 1988-03-21 | 1990-05-29 | Shell Oil Company | Hydrogenation of CO/olefin copolymer |
| CA1338577C (en) * | 1988-04-27 | 1996-09-03 | Jacobus Adrianus Bakkum | Process for the preparation of polymers of carbon monoxide with unsaturated compounds |
| CA1338578C (en) * | 1988-04-29 | 1996-09-03 | Gerrit Gerardus Rosenbrand | Process for the preparation of polymers of carbon monoxide with unsaturated compounds |
| US4965341A (en) * | 1988-06-08 | 1990-10-23 | Shell Oil Company | Polymerization of co/olefin with catalyst comprising sulfur bidentate ligand |
| US4904744A (en) * | 1988-06-08 | 1990-02-27 | Shell Oil Company | Polymer blends of carbon monoxide/olefin copolymer and poly(arylsulfone) polymer and oligomer |
| US4904716A (en) * | 1988-06-08 | 1990-02-27 | Shell Oil Company | Polymer blend of carbon monoxide/olefin copolymer and poly(arylsulfone)oligomer |
| US5096965A (en) * | 1988-06-27 | 1992-03-17 | Shell Oil Company | Polymeric compositions |
| US4940775A (en) * | 1988-07-13 | 1990-07-10 | Shell Oil Company | Polyketone from carbon monoxide/monoethylenically unsaturated hydrocarbon/non-conjugated alkadiene |
| US5001221A (en) * | 1988-09-19 | 1991-03-19 | Shell Oil Company | Polymerization of carbon monoxide/olefin with catalyst/diluent recycle |
| US5010171A (en) * | 1988-09-22 | 1991-04-23 | Shell Oil Company | Carbon monoxide/olefin polymerization with catalyst comprising p. bidentate ligand having non-hydrocarbyl substituent |
| NL8802391A (nl) * | 1988-09-29 | 1990-04-17 | Shell Int Research | Bereiding van polymeren. |
| EP0364046A3 (en) * | 1988-10-12 | 1991-03-27 | Shell Internationale Researchmaatschappij B.V. | Preparation of tetraaryldiphosphines |
| NL8802611A (nl) * | 1988-10-24 | 1990-05-16 | Shell Int Research | Katalysatorcomposities. |
| GB8826324D0 (en) * | 1988-11-10 | 1988-12-14 | Shell Int Research | Thermosetting resin compositions |
| ES2028434T3 (es) * | 1988-11-11 | 1992-07-01 | Shell Internationale Research Maatschappij B.V. | Composiciones cataliticas. |
| US5169928A (en) * | 1988-11-28 | 1992-12-08 | Shell Oil Company | Preparation of regio-regular copolymer of CO/olefin of at least three carbon atoms in the presence of tetraalkyl diphosphine |
| ATE135023T1 (de) * | 1988-11-28 | 1996-03-15 | Shell Int Research | Polymere von carbonmonoxid mit einem oder mehreren alphaolefinen |
| US5010172A (en) * | 1989-01-20 | 1991-04-23 | Shell Oil Company | Polymerization of carbon monoxide/olefin with tertiary monophosphine or secondary monophosphine oxide |
| EP0380162B1 (en) * | 1989-01-26 | 1995-04-12 | Shell Internationale Researchmaatschappij B.V. | Catalyst compositions |
| NL8900629A (nl) * | 1989-03-15 | 1990-10-01 | Shell Int Research | Complexe palladiumverbindingen. |
| US5061785A (en) * | 1989-03-29 | 1991-10-29 | Shell Oil Company | Polymerization of carbon monoxide/olefin with tertiary aliphatic monophosphine catalyst |
| US4885318A (en) * | 1989-03-31 | 1989-12-05 | Shell Oil Company | Polyketone flame retardant composition |
| US4921897A (en) * | 1989-03-31 | 1990-05-01 | Shell Oil Company | Flame retardant composition containing zinc borate |
| US4885328A (en) * | 1989-03-31 | 1989-12-05 | Shell Oil Company | Flame retardant compositions |
| CN1025039C (zh) * | 1989-04-19 | 1994-06-15 | 国际壳牌研究有限公司 | 制备一氧化碳与烯烃的共聚物的方法 |
| US5225386A (en) * | 1989-04-19 | 1993-07-06 | Shell Oil Company | Polymerization of carbon monoxide/olefin with polyalkoxyalkane |
| US4954548A (en) * | 1989-04-27 | 1990-09-04 | Shell Oil Company | Ethylene-carbon monoxide copolymer stabilization |
| US5149733A (en) * | 1989-07-20 | 1992-09-22 | Shell Oil Company | Stabilized polymers |
| US4954552A (en) * | 1989-05-15 | 1990-09-04 | Shell Oil Company | Stabilized carbon monoxide-olefin copolymer compositions |
| US4960807A (en) * | 1989-05-15 | 1990-10-02 | Shell Oil Company | Stabilized carbon monoxide olefin copolymer compositions |
| US4983649A (en) * | 1989-05-15 | 1991-01-08 | Shell Oil Company | Stabilized polyketone blend |
| US5106952A (en) * | 1989-05-24 | 1992-04-21 | Shell Oil Company | Carbon monoxide/norbornene copolymer having spiroketal structural units |
| US4954555A (en) * | 1989-05-30 | 1990-09-04 | Shell Oil Company | Stabilized carbon monoxide-olefin copolymer compositions |
| US5055552A (en) * | 1989-06-14 | 1991-10-08 | Shell Oil Company | Polymerization of co/olefin with phosphorus bidentate ligand-solid support reaction product |
| US4988754A (en) * | 1989-06-27 | 1991-01-29 | Shell Oil Company | Stabilized compositions |
| US5057599A (en) * | 1989-07-14 | 1991-10-15 | Shell Oil Company | Polymerization of carbon monoxide/olefin with aromatic tetradentate phosphorus ligand |
| US5210311A (en) * | 1989-07-14 | 1993-05-11 | Shell Oil Company | Aromatic tetradentate phosphine |
| US5064901A (en) * | 1989-07-20 | 1991-11-12 | Shell Oil Company | Blends of polyketones and carboxylated, hydrogenated block copolymers |
| USH917H (en) | 1989-07-28 | 1991-05-07 | Shell Oil Company | Polymer blend |
| USH889H (en) * | 1989-08-07 | 1991-02-05 | Shell Oil Company | Stabilized compositions |
| US5021547A (en) * | 1989-08-07 | 1991-06-04 | Shell Oil Company | Continuous polymerization of Co/olefin in plurality of reactors in series |
| US5177185A (en) * | 1989-08-17 | 1993-01-05 | Shell Oil Company | Polymerization of co/olefin with sets of temperature/pressure conditions |
| US5077384A (en) * | 1989-08-17 | 1991-12-31 | Shell Oil Company | Carbon monoxide/olefin copolymer having wide molecular weight distribution |
| US5039743A (en) * | 1989-09-25 | 1991-08-13 | Shell Oil Company | Polymer blends of polyketones, polyamides and carboxylated block copolymers |
| US5073327A (en) * | 1989-09-25 | 1991-12-17 | Shell Oil Company | Process for producing mono- or biaxially drawn polyketone films |
| US5059676A (en) * | 1989-09-25 | 1991-10-22 | Shell Oil Company | Polymers of carbon monoxide and bicyclic unsaturated carboxylic acid compound |
| US4960865A (en) * | 1989-09-25 | 1990-10-02 | Shell Oil Company | Water wash of olefin/carbon monoxide polymer |
| US5091506A (en) * | 1989-10-11 | 1992-02-25 | Shell Oil Compnay | Polymerization of carbon monoxide/norbornene with p bidentate ligand |
| US5059678A (en) * | 1989-10-26 | 1991-10-22 | Shell Oil Company | Polymerization of olefin/carbon monoxide with palladium salt, bidentate ligand and carboxylic acid ester or anhydride |
| US5043389A (en) * | 1989-10-31 | 1991-08-27 | Shell Oil Company | Blends of linear alternating polyketones, polyamides and olefin-carboxylic acid copolymers |
| US5068289A (en) * | 1989-11-06 | 1991-11-26 | Shell Oil Company | Reinforced polymer compositions |
| US5095091A (en) * | 1989-11-15 | 1992-03-10 | Shell Oil Company | Polymerization of co/olefin with two distinct temperatures |
| US5102942A (en) * | 1989-12-18 | 1992-04-07 | Shell Oil Company | Polyketone polymer blend |
| US4999399A (en) * | 1990-01-29 | 1991-03-12 | Shell Oil Company | Polymer compositions |
| US5028652A (en) * | 1990-02-05 | 1991-07-02 | Shell Oil Company | Stabilized polymer compositions of linear alternating polyketones and zinc aluminate |
| US5049630A (en) * | 1990-01-29 | 1991-09-17 | Shell Oil Company | Blends of polyketones and acidic polymers stabilized with salts |
| US5115094A (en) * | 1990-01-30 | 1992-05-19 | Shell Oil Company | Polymerization of co/olefin with molar ratio of non hydrohalogenic acid to palladium compound |
| US5082885A (en) * | 1990-02-08 | 1992-01-21 | Shell Oil Company | Stabilized ethylene-carbon monoxide copolymer compositions |
| US5122591A (en) * | 1990-03-22 | 1992-06-16 | Shell Oil Company | Polymerization of co/olefin with increased catalyst composition concentration during polymerization start up |
| GB2242189A (en) * | 1990-03-23 | 1991-09-25 | Shell Int Research | Bidentate ligands and their precursors |
| GB9007432D0 (en) * | 1990-04-03 | 1990-05-30 | Shell Int Research | Copolymer compositions |
| NL9000812A (nl) * | 1990-04-06 | 1991-11-01 | Shell Int Research | Bereiding van polymeren. |
| US5229343A (en) * | 1990-04-27 | 1993-07-20 | Shell Oil Company | Polymerization process |
| US5171832A (en) * | 1990-04-27 | 1992-12-15 | Shell Oil Company | Polymerization of carbon monoxide/olefin with p bidentate ligand having (1) alkoxy phenyl p group and (2) monosubstituted divalent bridging group |
| NL9001114A (nl) * | 1990-05-10 | 1991-12-02 | Shell Int Research | Katalysatorcomposities. |
| NL9001229A (nl) * | 1990-05-29 | 1991-12-16 | Shell Int Research | Katalysatorcomposities. |
| NL9001255A (nl) * | 1990-06-01 | 1992-01-02 | Shell Int Research | Bereiding van polymeren. |
| US5079285A (en) * | 1990-08-08 | 1992-01-07 | Shell Oil Company | Stabilized compositions |
| GB9020976D0 (en) * | 1990-09-26 | 1990-11-07 | British Petroleum Co Plc | Process for preparing polyketones |
| EP0490452B1 (en) * | 1990-12-13 | 1996-09-11 | Shell Internationale Researchmaatschappij B.V. | Catalyst compositions and process for the preparation of polymers |
| US5175210A (en) * | 1991-06-14 | 1992-12-29 | Shell Oil Company | Polymer blends |
| US5128402A (en) * | 1991-07-31 | 1992-07-07 | Shell Oil Company | Melt stabilized polyketone blend containing a mixture of magnesium oxide and titanium oxide |
| US5126496A (en) * | 1991-07-31 | 1992-06-30 | Shell Oil Company | Melt stabilized polyketone blend containing a mixture of magnesium oxide and alumina |
| US5247064A (en) * | 1991-08-06 | 1993-09-21 | Shell Oil Company | Polymerization of co/olefin with p bidentate ligand |
| CA2091413A1 (en) * | 1992-03-11 | 1993-09-12 | Anna Sommazzi | Homogeneous catalytic system and process for copolymerizing olefins with carbon monoxide |
| CA2091412A1 (en) * | 1992-03-11 | 1993-09-12 | Anna Sommazzi | Catalytic system and process for copolymerizing carbon monoxide with one or more olefins |
| US5644023A (en) * | 1992-04-21 | 1997-07-01 | Union Carbide Chemicals & Plastics Technology Corporation | Process for the manufacture of copolymers of ethylene and carbon monoxide |
| WO1994000623A1 (en) * | 1992-06-26 | 1994-01-06 | Akzo Nobel N.V. | Polyketone yarn and a method of manufacturing same |
| US5820806A (en) * | 1993-01-13 | 1998-10-13 | Akzo Nobel Nv | Process for the preparation of polyketone fibers |
| GB9307702D0 (en) * | 1993-04-14 | 1993-06-02 | Shell Int Research | Preparation of co-polymers |
| IT1265364B1 (it) * | 1993-12-03 | 1996-11-22 | Enichem Spa | Sistema catalittico e processo per la copolimerizzazione di olefine con ossido di carbonio |
| EP0743336A3 (en) * | 1995-05-18 | 1997-04-23 | Shell Int Research | Process for the preparation of linear, alternating copolymers from carbon monoxide and ethene and another olefinically unsaturated compound |
| EP0774479A3 (en) | 1995-11-17 | 1998-01-14 | ENICHEM S.p.A. | Process for the preparation of copolymers based on carbon monoxide and at least one compound containing an alkenyl unsaturation |
| KR20010040916A (ko) | 1998-02-12 | 2001-05-15 | 스무크 제이. | 폴리케톤 섬유의 제조방법 |
| ES2676498T3 (es) | 2015-11-13 | 2018-07-20 | Ems-Patent Ag | Materiales policetónicos alifáticos ignífugos, cuerpos de moldeo derivados de ellas así como procedimientos para su producción |
| EP3168252B1 (de) | 2015-11-13 | 2019-01-09 | Ems-Patent Ag | Polyketon-formmassen mit verbesserten eigenschaften, hieraus hergestellter formkörper sowie verfahren zu dessen herstellung |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3480845D1 (de) * | 1983-04-06 | 1990-02-01 | Shell Int Research | Verfahren zur herstellung von polyketonen. |
| NL8403035A (nl) * | 1984-10-05 | 1986-05-01 | Shell Int Research | Werkwijze ter bereiding van polyketonen. |
| IN168306B (hu) * | 1986-03-05 | 1991-03-09 | Shell Int Research | |
| CA1324456C (en) * | 1986-03-05 | 1993-11-16 | Johannes A. M. Van Broekhoven | Catalyst compositions |
| CA1316624C (en) * | 1986-06-20 | 1993-04-20 | Eit Drent | Polymers |
| US4804739A (en) * | 1986-07-01 | 1989-02-14 | Shell Oil Company | Process for preparing carbon monoxide polymer with quaternary phosphonium compound bidentate ligand |
-
1987
- 1987-05-04 IN IN384/DEL/87A patent/IN171627B/en unknown
- 1987-05-05 DE DE8787200826T patent/DE3776033D1/de not_active Expired - Fee Related
- 1987-05-05 EP EP87200826A patent/EP0257663B1/en not_active Expired - Lifetime
- 1987-05-05 ES ES198787200826T patent/ES2028048T3/es not_active Expired - Lifetime
- 1987-05-05 AT AT87200826T patent/ATE71639T1/de not_active IP Right Cessation
- 1987-05-07 DK DK233887A patent/DK233887A/da not_active Application Discontinuation
- 1987-05-07 IL IL82449A patent/IL82449A/xx unknown
- 1987-05-11 IE IE118487A patent/IE60429B1/en not_active IP Right Cessation
- 1987-05-13 HU HU908099A patent/HU204279B/hu not_active IP Right Cessation
- 1987-05-13 PL PL1987265671A patent/PL151697B1/pl unknown
- 1987-05-13 KR KR1019870004772A patent/KR960010252B1/ko not_active IP Right Cessation
- 1987-05-13 NO NO871981A patent/NO169235C/no unknown
- 1987-05-13 NZ NZ220290A patent/NZ220290A/xx unknown
- 1987-05-13 FI FI872118A patent/FI90557C/fi not_active IP Right Cessation
- 1987-05-13 CN CN87104306A patent/CN1012438B/zh not_active Expired
- 1987-05-13 CA CA000537047A patent/CA1333810C/en not_active Expired - Fee Related
- 1987-05-13 BR BR8702449A patent/BR8702449A/pt not_active IP Right Cessation
- 1987-05-13 AU AU72763/87A patent/AU597360B2/en not_active Ceased
- 1987-05-14 JP JP62116047A patent/JPH0822914B2/ja not_active Expired - Lifetime
-
1992
- 1992-03-31 GR GR920400580T patent/GR3004209T3/el unknown
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- 1995-09-12 JP JP7258315A patent/JP2863997B2/ja not_active Expired - Lifetime
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