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
-
- 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 |
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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 |
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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 |
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HU908099A HU204279B (en) | 1986-08-26 | 1987-05-13 | Process for producing phosphine derivatives |
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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) |
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DE3480845D1 (de) * | 1983-04-06 | 1990-02-01 | Shell Int Research | Verfahren zur herstellung von polyketonen. |
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1987
- 1987-05-04 IN IN384/DEL/87A patent/IN171627B/en unknown
- 1987-05-05 AT AT87200826T patent/ATE71639T1/de not_active IP Right Cessation
- 1987-05-05 ES ES198787200826T patent/ES2028048T3/es not_active Expired - Lifetime
- 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
- 1987-05-07 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 AU AU72763/87A patent/AU597360B2/en not_active Ceased
- 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 HU HU908099A patent/HU204279B/hu not_active IP Right Cessation
- 1987-05-13 BR BR8702449A patent/BR8702449A/pt not_active IP Right Cessation
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