CN113454095A - 酰基膦氧类化合物及其制备方法 - Google Patents
酰基膦氧类化合物及其制备方法 Download PDFInfo
- Publication number
- CN113454095A CN113454095A CN201880099925.2A CN201880099925A CN113454095A CN 113454095 A CN113454095 A CN 113454095A CN 201880099925 A CN201880099925 A CN 201880099925A CN 113454095 A CN113454095 A CN 113454095A
- Authority
- CN
- China
- Prior art keywords
- compound
- organic solvent
- hours
- phenyl
- grignard reagent
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 80
- 238000002360 preparation method Methods 0.000 title abstract description 18
- -1 acyl phosphine oxide compound Chemical class 0.000 claims abstract description 117
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims abstract description 70
- 239000003960 organic solvent Substances 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 34
- 239000000126 substance Substances 0.000 claims abstract description 33
- 238000006467 substitution reaction Methods 0.000 claims abstract description 22
- 239000003999 initiator Substances 0.000 claims abstract description 15
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 183
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 94
- 239000000203 mixture Substances 0.000 claims description 75
- 239000000243 solution Substances 0.000 claims description 75
- 238000006243 chemical reaction Methods 0.000 claims description 68
- 239000011259 mixed solution Substances 0.000 claims description 59
- 239000007818 Grignard reagent Substances 0.000 claims description 55
- 150000004795 grignard reagents Chemical class 0.000 claims description 55
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 47
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 claims description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 39
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 36
- 150000007530 organic bases Chemical class 0.000 claims description 33
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 32
- 239000002841 Lewis acid Substances 0.000 claims description 20
- 150000007517 lewis acids Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 14
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052740 iodine Chemical group 0.000 claims description 10
- 239000011630 iodine Chemical group 0.000 claims description 10
- 238000010791 quenching Methods 0.000 claims description 10
- 230000000171 quenching effect Effects 0.000 claims description 10
- 230000035484 reaction time Effects 0.000 claims description 10
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 8
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 7
- 239000005051 trimethylchlorosilane Substances 0.000 claims description 7
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 6
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims description 6
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 claims description 5
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 claims description 4
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- QCEPCNPORJNRJB-UHFFFAOYSA-N [tert-butyl(dimethyl)silyl] methanesulfonate Chemical compound CC(C)(C)[Si](C)(C)OS(C)(=O)=O QCEPCNPORJNRJB-UHFFFAOYSA-N 0.000 claims description 3
- WLLIXJBWWFGEHT-UHFFFAOYSA-N [tert-butyl(dimethyl)silyl] trifluoromethanesulfonate Chemical compound CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F WLLIXJBWWFGEHT-UHFFFAOYSA-N 0.000 claims description 3
- ACTAPAGNZPZLEF-UHFFFAOYSA-N chloro(tripropyl)silane Chemical compound CCC[Si](Cl)(CCC)CCC ACTAPAGNZPZLEF-UHFFFAOYSA-N 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 229940071870 hydroiodic acid Drugs 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- ZWFWUUVCEPVZOW-UHFFFAOYSA-M sodium;chloro(trimethyl)silane;bromide Chemical compound [Na+].[Br-].C[Si](C)(C)Cl ZWFWUUVCEPVZOW-UHFFFAOYSA-M 0.000 claims description 3
- GVQPSSGWDYNZQT-UHFFFAOYSA-M sodium;chloro(trimethyl)silane;iodide Chemical compound [Na+].[I-].C[Si](C)(C)Cl GVQPSSGWDYNZQT-UHFFFAOYSA-M 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 claims description 3
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 claims description 3
- JSQJUDVTRRCSRU-UHFFFAOYSA-N tributyl(chloro)silane Chemical compound CCCC[Si](Cl)(CCCC)CCCC JSQJUDVTRRCSRU-UHFFFAOYSA-N 0.000 claims description 3
- NTJPIRDYMVYFNP-UHFFFAOYSA-M trimethylsilylmethanesulfonate Chemical compound C[Si](C)(C)CS([O-])(=O)=O NTJPIRDYMVYFNP-UHFFFAOYSA-M 0.000 claims description 3
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 2
- 238000007867 post-reaction treatment Methods 0.000 claims 1
- 239000003513 alkali Substances 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 78
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 36
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 30
- 239000012074 organic phase Substances 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 239000012065 filter cake Substances 0.000 description 14
- 238000004537 pulping Methods 0.000 description 14
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 12
- 230000009286 beneficial effect Effects 0.000 description 10
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000012535 impurity Substances 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 238000013517 stratification Methods 0.000 description 7
- 238000000967 suction filtration Methods 0.000 description 7
- 239000003039 volatile agent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000009776 industrial production Methods 0.000 description 6
- UDWYGCUCFWUHOL-UHFFFAOYSA-N C1(=C(C=CC=C1)C1=CC=C(C(=O)P(C2=CC=CC=C2)(C2=CC=CC=C2)=O)C=C1)C Chemical compound C1(=C(C=CC=C1)C1=CC=C(C(=O)P(C2=CC=CC=C2)(C2=CC=CC=C2)=O)C=C1)C UDWYGCUCFWUHOL-UHFFFAOYSA-N 0.000 description 4
- ZHIPXAFNKGZMSC-UHFFFAOYSA-N bis(4-methylphenyl)-oxophosphanium Chemical compound C1=CC(C)=CC=C1[P+](=O)C1=CC=C(C)C=C1 ZHIPXAFNKGZMSC-UHFFFAOYSA-N 0.000 description 4
- DIJAKAWXMZJVED-UHFFFAOYSA-N diphenylphosphoryl-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 DIJAKAWXMZJVED-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UKRQMDIFLKHCRO-UHFFFAOYSA-N 2,4,6-trimethylbenzoyl chloride Chemical compound CC1=CC(C)=C(C(Cl)=O)C(C)=C1 UKRQMDIFLKHCRO-UHFFFAOYSA-N 0.000 description 3
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ATYJNUPYAOFIAK-UHFFFAOYSA-N [4-(dimethylamino)phenyl]-diphenylphosphorylmethanone Chemical compound CN(C)c1ccc(cc1)C(=O)P(=O)(c1ccccc1)c1ccccc1 ATYJNUPYAOFIAK-UHFFFAOYSA-N 0.000 description 3
- DZHSVSBJDNJICY-UHFFFAOYSA-N bis(4-methylphenyl)phosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound C1=CC(C)=CC=C1P(=O)(C=1C=CC(C)=CC=1)C(=O)C1=C(C)C=C(C)C=C1C DZHSVSBJDNJICY-UHFFFAOYSA-N 0.000 description 3
- QNAQDZUDDRKNEX-UHFFFAOYSA-N diphenylphosphoryl-(4-methylphenyl)methanethione Chemical compound CC1=CC=C(C=C1)C(=S)P(=O)(C2=CC=CC=C2)C3=CC=CC=C3 QNAQDZUDDRKNEX-UHFFFAOYSA-N 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- HIKRJHFHGKZKRI-UHFFFAOYSA-N 2,4,6-trimethylbenzaldehyde Chemical compound CC1=CC(C)=C(C=O)C(C)=C1 HIKRJHFHGKZKRI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- OAADXJFIBNEPLY-UHFFFAOYSA-N methoxy(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(OC)C1=CC=CC=C1 OAADXJFIBNEPLY-UHFFFAOYSA-N 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 238000000016 photochemical curing Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- UGJDXRVQCYBXAJ-UHFFFAOYSA-N 4-(dimethylamino)benzoyl chloride Chemical compound CN(C)C1=CC=C(C(Cl)=O)C=C1 UGJDXRVQCYBXAJ-UHFFFAOYSA-N 0.000 description 1
- NWPBFGWVZQGAHM-UHFFFAOYSA-N 4-methylbenzenecarbothioyl chloride Chemical compound CC1=CC=C(C(Cl)=S)C=C1 NWPBFGWVZQGAHM-UHFFFAOYSA-N 0.000 description 1
- JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- AZAQDXJWNHXLOG-UHFFFAOYSA-N phenylphosphanium;chloride Chemical compound [Cl-].[PH3+]C1=CC=CC=C1 AZAQDXJWNHXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5337—Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
-
- 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
- C07F9/5022—Aromatic phosphines (P-C aromatic linkage)
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
PCT国内申请,说明书已公开。
Claims (19)
- PCT国内申请,权利要求书已公开。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/CN2018/119922 WO2020113585A1 (zh) | 2018-12-07 | 2018-12-07 | 酰基膦氧类化合物及其制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113454095A true CN113454095A (zh) | 2021-09-28 |
CN113454095B CN113454095B (zh) | 2023-08-22 |
Family
ID=70974025
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201880099925.2A Active CN113454095B (zh) | 2018-12-07 | 2018-12-07 | 酰基膦氧类化合物及其制备方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20220106340A1 (zh) |
EP (1) | EP3892625A4 (zh) |
JP (1) | JP7432616B2 (zh) |
KR (1) | KR20210105377A (zh) |
CN (1) | CN113454095B (zh) |
WO (1) | WO2020113585A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113929795A (zh) * | 2021-11-16 | 2022-01-14 | 上海墨之炫科技有限公司 | 一种酰基氧化膦类光引发剂 |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112194682A (zh) * | 2020-08-12 | 2021-01-08 | 广州理文科技有限公司 | 一种新型光引发剂及其制备方法 |
CN112547122A (zh) * | 2020-12-18 | 2021-03-26 | 商河知济新材料技术中心 | 叔丁醇盐和吡啶盐在制备一种光引发剂中的用途 |
CN112940034A (zh) * | 2021-02-05 | 2021-06-11 | 大连和源化学科技开发有限公司 | 一种催化合成苯甲酰基膦氧类化合物的方法 |
CN114163477A (zh) * | 2021-12-17 | 2022-03-11 | 长沙新宇高分子科技有限公司 | 一种苯甲酰基二苯基氧化膦衍生物的连续制备工艺 |
CN114835755B (zh) * | 2022-06-08 | 2023-08-18 | 常州德能新材料有限公司 | 催化聚合的双次膦酰胺金属配合物催化剂及其制备方法 |
CN115160362B (zh) * | 2022-09-05 | 2022-12-02 | 天津久日新材料股份有限公司 | 一种2,4,6-三甲基苯甲酰基二苯基氧化膦的制备方法 |
CN117209168B (zh) * | 2023-05-12 | 2024-03-15 | 上海飞凯材料科技股份有限公司 | 一种光纤涂覆组合物、光纤及其制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1328564A (zh) * | 1998-11-30 | 2001-12-26 | 西巴特殊化学品控股有限公司 | 酰基膦和其衍生物的制备方法 |
CN103333206A (zh) * | 2013-07-04 | 2013-10-02 | 南通泰通化学科技有限公司 | Tpo光引发剂的制备方法 |
CN105198927A (zh) * | 2015-10-27 | 2015-12-30 | 青岛富斯林化工科技有限公司 | 一种苯甲酰基二苯基氧化膦类衍生物的制备方法 |
CN105238000A (zh) * | 2014-07-10 | 2016-01-13 | 中山台光电子材料有限公司 | 一种低介电复合材料及其积层板和电路板 |
CN106496268A (zh) * | 2016-09-09 | 2017-03-15 | 苏州大学 | 一种膦酰基取代甲醇衍生物及其制备方法与应用 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2830928A1 (de) * | 1978-07-14 | 1980-01-31 | Basf Ag | Lichthaertbare form-, traenk- und ueberzugsmassen |
DE3133419A1 (de) * | 1981-08-24 | 1983-03-10 | Basf Ag, 6700 Ludwigshafen | Acylphosphinoxidverbindungen und ihre verwendung |
JP5513794B2 (ja) | 2009-07-14 | 2014-06-04 | パナソニック株式会社 | 物干し装置 |
CN102875598B (zh) * | 2011-07-11 | 2016-09-07 | 深圳市有为化学技术有限公司 | (二苯膦氧基)(均三甲苯基)甲酮和(苯膦氧基)双(均三甲苯基甲酮)的制备方法 |
CN103073658A (zh) | 2011-10-26 | 2013-05-01 | 深圳市有为化学技术有限公司 | 新型芳香羟基酮和膦酰氧化物的光引发剂混合物及其与光吸收剂的复合体系 |
CN103880882A (zh) * | 2014-03-17 | 2014-06-25 | 襄阳市科民化工科技有限公司 | 一种光引发剂tpo的制备方法 |
JP5877890B2 (ja) | 2014-07-18 | 2016-03-08 | Thk株式会社 | ねじ装置用冷却ノズル及び運動案内装置用冷却ノズル |
CN107304220B (zh) * | 2016-04-22 | 2020-03-31 | 江苏英力科技发展有限公司 | 一种“一锅法”合成2,4,6-三甲基苯甲酰基-二苯基氧化膦的方法 |
CN106083928A (zh) * | 2016-08-04 | 2016-11-09 | 长沙优阳机电设备有限公司 | 一种有机磷化合物 |
-
2018
- 2018-12-07 EP EP18942325.4A patent/EP3892625A4/en active Pending
- 2018-12-07 KR KR1020217021263A patent/KR20210105377A/ko not_active Application Discontinuation
- 2018-12-07 CN CN201880099925.2A patent/CN113454095B/zh active Active
- 2018-12-07 WO PCT/CN2018/119922 patent/WO2020113585A1/zh unknown
- 2018-12-07 JP JP2021554784A patent/JP7432616B2/ja active Active
- 2018-12-07 US US17/311,649 patent/US20220106340A1/en active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1328564A (zh) * | 1998-11-30 | 2001-12-26 | 西巴特殊化学品控股有限公司 | 酰基膦和其衍生物的制备方法 |
CN103333206A (zh) * | 2013-07-04 | 2013-10-02 | 南通泰通化学科技有限公司 | Tpo光引发剂的制备方法 |
CN105238000A (zh) * | 2014-07-10 | 2016-01-13 | 中山台光电子材料有限公司 | 一种低介电复合材料及其积层板和电路板 |
CN105198927A (zh) * | 2015-10-27 | 2015-12-30 | 青岛富斯林化工科技有限公司 | 一种苯甲酰基二苯基氧化膦类衍生物的制备方法 |
CN106496268A (zh) * | 2016-09-09 | 2017-03-15 | 苏州大学 | 一种膦酰基取代甲醇衍生物及其制备方法与应用 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113929795A (zh) * | 2021-11-16 | 2022-01-14 | 上海墨之炫科技有限公司 | 一种酰基氧化膦类光引发剂 |
Also Published As
Publication number | Publication date |
---|---|
JP2022520286A (ja) | 2022-03-29 |
EP3892625A4 (en) | 2021-11-24 |
KR20210105377A (ko) | 2021-08-26 |
WO2020113585A1 (zh) | 2020-06-11 |
EP3892625A1 (en) | 2021-10-13 |
JP7432616B2 (ja) | 2024-02-16 |
US20220106340A1 (en) | 2022-04-07 |
CN113454095B (zh) | 2023-08-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN113454095A (zh) | 酰基膦氧类化合物及其制备方法 | |
TW309523B (zh) | ||
CN113387954A (zh) | 一种瑞德西韦中间体的制备方法 | |
CN112174989B (zh) | 一种克立硼罗的制备方法 | |
CN103435653B (zh) | 一种六苯氧基环三磷腈的制备方法 | |
CN105175346B (zh) | 一种合成瑞舒伐他汀钙中间体的方法 | |
TWI790442B (zh) | 醯基膦氧類化合物及其製備方法 | |
CN102190581A (zh) | 用于制备4'-卤烷基联苯基-2-羧酸的方法 | |
CN100366595C (zh) | 一种经由中间体2-氟-6-卤代苯酚制备1,2-二烷氧基-3-氟苯的方法 | |
CN113801045A (zh) | 2-硝基-4-甲砜基苯甲酸的制备方法 | |
CN113979834B (zh) | 一种光固化引发剂及其制备方法、包含其的光固化组合物 | |
JP4695742B2 (ja) | 塩素化されたピリジンスルホン酸クロリドの製造方法 | |
JPS6049170B2 (ja) | β−アルコキシエトキシメチルハライドの製造方法 | |
JPH0588891B2 (zh) | ||
CN114805435B (zh) | 联芳基膦化合物的制备方法 | |
CN116135865A (zh) | 光引发剂tpo的制备方法 | |
KR20030062591A (ko) | 디알콕시트리틸할라이드의 새로운 제조방법 | |
US3577482A (en) | Process for the preparation of thionophosphonates | |
CN109942406A (zh) | 一种2-(3,5-双-三氟甲基-苯基)-2-甲基-丙酸的制备方法 | |
CN117777198A (zh) | 一种基于磷杂芴结构的三芳基膦化合物及其制备方法 | |
CN117886971A (zh) | 一种原位实现光引发的方法 | |
CN117105977A (zh) | 一种邻羰基磷酸酯类化合物的便捷合成方法 | |
US20230151030A1 (en) | Process for producing a biphenyl metallocene complex | |
CN116063348A (zh) | 一种基于新型磷-碳键偶联反应合成芳基磷化合物的方法 | |
CN116947917A (zh) | 一种阻燃剂磷酸三苯酯的制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |