CA2255161C - Preparation de monoarylphosphines et de diarylphosphines - Google Patents

Preparation de monoarylphosphines et de diarylphosphines Download PDF

Info

Publication number: CA2255161C
Authority: CA; Canada
Prior art keywords: process according; phosphine; reaction; psig; carried out
Prior art date: 1998-12-03
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.): Expired - Fee Related

Application number

CA 2255161

Other languages

English (en)

Other versions

CA2255161A1 (fr

Inventor

John H. Hillhouse

William Andrew Rickelton

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.)

Cytec Canada Inc

Original Assignee

Cytec Canada Inc

Priority date (The priority date 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 date listed.)

1998-12-03

Filing date

1998-12-03

Publication date

2003-09-16

1998-12-03 Application filed by Cytec Canada Inc filed Critical Cytec Canada Inc

1998-12-03 Priority to CA 2255161 priority Critical patent/CA2255161C/fr

1999-10-12 Priority to US09/856,754 priority patent/US6563005B1/en

1999-10-12 Priority to PCT/US1999/023777 priority patent/WO2000032613A1/fr

1999-10-12 Priority to AU64278/99A priority patent/AU6427899A/en

1999-10-12 Priority to EP99951952A priority patent/EP1140950A1/fr

2000-06-03 Publication of CA2255161A1 publication Critical patent/CA2255161A1/fr

2003-09-16 Application granted granted Critical

2003-09-16 Publication of CA2255161C publication Critical patent/CA2255161C/fr

2018-12-03 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 56
-1 aryl compound Chemical class 0.000 claims abstract description 29
229910000073 phosphorus hydride Inorganic materials 0.000 claims abstract description 28
239000003054 catalyst Substances 0.000 claims abstract description 16
125000003118 aryl group Chemical group 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
229910052751 metal Inorganic materials 0.000 claims abstract description 5
239000002184 metal Substances 0.000 claims abstract description 5
229910052799 carbon Inorganic materials 0.000 claims abstract description 4
238000006243 chemical reaction Methods 0.000 claims description 31
238000000034 method Methods 0.000 claims description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 26
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 claims description 10
SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 8
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 claims description 7
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 7
239000008096 xylene Substances 0.000 claims description 7
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 claims description 6
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
150000001412 amines Chemical group 0.000 claims description 4
239000001099 ammonium carbonate Substances 0.000 claims description 4
125000006575 electron-withdrawing group Chemical group 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
229910000013 Ammonium bicarbonate Inorganic materials 0.000 claims description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
235000012538 ammonium bicarbonate Nutrition 0.000 claims description 2
235000012501 ammonium carbonate Nutrition 0.000 claims description 2
229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
239000000920 calcium hydroxide Substances 0.000 claims description 2
229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 2
239000000292 calcium oxide Substances 0.000 claims description 2
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
239000000347 magnesium hydroxide Substances 0.000 claims description 2
229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
239000000395 magnesium oxide Substances 0.000 claims description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims description 2
150000003222 pyridines Chemical class 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
239000000203 mixture Substances 0.000 description 6
150000002940 palladium Chemical class 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 5
239000012071 phase Substances 0.000 description 5
RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
LFMWZTSOMGDDJU-UHFFFAOYSA-N 1,4-diiodobenzene Chemical compound IC1=CC=C(I)C=C1 LFMWZTSOMGDDJU-UHFFFAOYSA-N 0.000 description 3
ZLMKEENUYIUKKC-UHFFFAOYSA-N 1-iodo-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(I)=C1 ZLMKEENUYIUKKC-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
IGISPMBUGPHLBY-UHFFFAOYSA-N 1-iodo-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(I)=C1 IGISPMBUGPHLBY-UHFFFAOYSA-N 0.000 description 2
ZDZHCHYQNPQSGG-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalene Chemical group C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
150000001502 aryl halides Chemical class 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
230000010354 integration Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
DKFDVEXWZZOMGS-UHFFFAOYSA-N (2-phosphanylphenyl)phosphane Chemical compound PC1=CC=CC=C1P DKFDVEXWZZOMGS-UHFFFAOYSA-N 0.000 description 1
RFXWSCVCWQKXAL-UHFFFAOYSA-N (3,5-dimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(P)=C1 RFXWSCVCWQKXAL-UHFFFAOYSA-N 0.000 description 1
FDQGNUSTPULKCR-UHFFFAOYSA-N (4-iodophenyl)phosphane Chemical compound PC1=CC=C(I)C=C1 FDQGNUSTPULKCR-UHFFFAOYSA-N 0.000 description 1
DXKIVDBWRHJILG-UHFFFAOYSA-N (4-phosphanylphenyl)phosphane Chemical compound PC1=CC=C(P)C=C1 DXKIVDBWRHJILG-UHFFFAOYSA-N 0.000 description 1
QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
BBOLNFYSRZVALD-UHFFFAOYSA-N 1,2-diiodobenzene Chemical compound IC1=CC=CC=C1I BBOLNFYSRZVALD-UHFFFAOYSA-N 0.000 description 1
LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 1
JENANTGGBLOTIB-UHFFFAOYSA-N 1,5-diphenylpentan-3-one Chemical compound C=1C=CC=CC=1CCC(=O)CCC1=CC=CC=C1 JENANTGGBLOTIB-UHFFFAOYSA-N 0.000 description 1
WLPXNBYWDDYJTN-UHFFFAOYSA-N 1-bromo-2,3-dimethylbenzene Chemical class CC1=CC=CC(Br)=C1C WLPXNBYWDDYJTN-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
DANMWBNOPFBJSZ-UHFFFAOYSA-N 1-iodo-2,3-dimethylbenzene Chemical class CC1=CC=CC(I)=C1C DANMWBNOPFBJSZ-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
PZVUZZXBUDKPPH-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]phosphane Chemical compound FC(F)(F)C1=CC=CC(P)=C1 PZVUZZXBUDKPPH-UHFFFAOYSA-N 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
GPFIUEZTNRNFGD-UHFFFAOYSA-N bis(3,5-dimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(PC=2C=C(C)C=C(C)C=2)=C1 GPFIUEZTNRNFGD-UHFFFAOYSA-N 0.000 description 1
AIYZOGFWAYMZJN-UHFFFAOYSA-N bis(4-iodophenyl)phosphane Chemical compound C1=CC(I)=CC=C1PC1=CC=C(I)C=C1 AIYZOGFWAYMZJN-UHFFFAOYSA-N 0.000 description 1
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
SLEAUGLJRCPRES-UHFFFAOYSA-N bis[3-(trifluoromethyl)phenyl]phosphane Chemical compound FC(F)(F)C1=CC=CC(PC=2C=C(C=CC=2)C(F)(F)F)=C1 SLEAUGLJRCPRES-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000001183 hydrocarbyl group Chemical group 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
239000000543 intermediate Substances 0.000 description 1
XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical class ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
XEWVCDMEDQYCHX-UHFFFAOYSA-N n,n-diethylethanamine;hydron;iodide Chemical compound [I-].CC[NH+](CC)CC XEWVCDMEDQYCHX-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
150000002941 palladium compounds Chemical class 0.000 description 1
WXHIJDCHNDBCNY-UHFFFAOYSA-N palladium dihydride Chemical class [PdH2] WXHIJDCHNDBCNY-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
230000036647 reaction Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
FXXWRINCFWGFCV-UHFFFAOYSA-N tris[3-(trifluoromethyl)phenyl]phosphane Chemical compound FC(F)(F)C1=CC=CC(P(C=2C=C(C=CC=2)C(F)(F)F)C=2C=C(C=CC=2)C(F)(F)F)=C1 FXXWRINCFWGFCV-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
125000005023 xylyl group Chemical group 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
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/5063—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds
- C07F9/5072—Preparation; Separation; Purification; Stabilisation from compounds having the structure P-H or P-Heteroatom, in which one or more of such bonds are converted into P-C bonds from starting materials having the structure P-H

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA 2255161 1998-12-03 1998-12-03 Preparation de monoarylphosphines et de diarylphosphines Expired - Fee Related CA2255161C (fr)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
CA 2255161 CA2255161C (fr)	1998-12-03	1998-12-03	Preparation de monoarylphosphines et de diarylphosphines
US09/856,754 US6563005B1 (en)	1998-12-03	1999-10-12	Preparation of mono- and di-arylphosphines
PCT/US1999/023777 WO2000032613A1 (fr)	1998-12-03	1999-10-12	Preparation de monoarylphosphines et de diarylphosphines
AU64278/99A AU6427899A (en)	1998-12-03	1999-10-12	Preparation of mono- and di-arylphosphines
EP99951952A EP1140950A1 (fr)	1998-12-03	1999-10-12	Preparation de monoarylphosphines et de diarylphosphines

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 2255161 CA2255161C (fr)	1998-12-03	1998-12-03	Preparation de monoarylphosphines et de diarylphosphines

Publications (2)

Publication Number	Publication Date
CA2255161A1 CA2255161A1 (fr)	2000-06-03
CA2255161C true CA2255161C (fr)	2003-09-16

Family

ID=4163070

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2255161 Expired - Fee Related CA2255161C (fr)	1998-12-03	1998-12-03	Preparation de monoarylphosphines et de diarylphosphines

Country Status (4)

Country	Link
EP (1)	EP1140950A1 (fr)
AU (1)	AU6427899A (fr)
CA (1)	CA2255161C (fr)
WO (1)	WO2000032613A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2310355A1 (fr) *	2000-05-31	2001-11-30	John H. Hillhouse	Composes aromatiques phosphores et polymeres de ceux-ci
CA2310353A1 (fr) *	2000-05-31	2001-11-30	Cytec Technology Corp.	Synthese de diphosphinoarenes
DE102006013936A1 (de)	2006-03-16	2007-09-20	Valeo Schalter Und Sensoren Gmbh	Verfahren zum Betreiben eines Umgebungserkennungssystems eines Fahrzeugs, insbesondere eines Nahbereichserkennungs- oder Parkhilfesystems und zugehöriges System

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5399771A (en) *	1994-06-01	1995-03-21	Merck & Co., Inc.	Process of synthesizing binaphthyl derivatives
CA2144907A1 (fr) *	1995-03-17	1996-09-18	John H. Hillhouse	Preparation de phosphines, d'oxydes de phosphine et de sulfures de phosphine, arylalkyliques,

1998
- 1998-12-03 CA CA 2255161 patent/CA2255161C/fr not_active Expired - Fee Related
1999
- 1999-10-12 EP EP99951952A patent/EP1140950A1/fr not_active Withdrawn
- 1999-10-12 WO PCT/US1999/023777 patent/WO2000032613A1/fr not_active Ceased
- 1999-10-12 AU AU64278/99A patent/AU6427899A/en not_active Abandoned

Also Published As

Publication number	Publication date
AU6427899A (en)	2000-06-19
CA2255161A1 (fr)	2000-06-03
EP1140950A1 (fr)	2001-10-10
WO2000032613A1 (fr)	2000-06-08

Legal Events

Date	Code	Title	Description
1999-10-06	EEER	Examination request
2005-12-05	MKLA	Lapsed

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