DE2504333A1 - Substituierte cyclische phosphinoxide - Google Patents
Substituierte cyclische phosphinoxideInfo
- Publication number
- DE2504333A1 DE2504333A1 DE19752504333 DE2504333A DE2504333A1 DE 2504333 A1 DE2504333 A1 DE 2504333A1 DE 19752504333 DE19752504333 DE 19752504333 DE 2504333 A DE2504333 A DE 2504333A DE 2504333 A1 DE2504333 A1 DE 2504333A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- acid
- radical
- oxophospholine
- oxophospholanephosphonic
- 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.)
- Pending
Links
- 150000003004 phosphinoxides Chemical class 0.000 title 1
- -1 Cyclic phosphine oxides Chemical class 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 11
- 150000005840 aryl radicals Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003999 initiator Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 239000002253 acid Substances 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000243 solution Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- IUUONVQOMMQAEH-UHFFFAOYSA-N 1-methyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CP1(=O)CCC=C1 IUUONVQOMMQAEH-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 150000001718 carbodiimides Chemical class 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- LVFUWJLIDMSANU-UHFFFAOYSA-N methoxy(methylsulfanyl)phosphinous acid Chemical compound COP(O)SC LVFUWJLIDMSANU-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- ANNACVSWAGJSRF-UHFFFAOYSA-N 1-methyl-2h-phosphol-3-one Chemical compound CP1CC(=O)C=C1 ANNACVSWAGJSRF-UHFFFAOYSA-N 0.000 description 2
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- WQAWEUZTDVWTDB-UHFFFAOYSA-N dimethyl(oxo)phosphanium Chemical compound C[P+](C)=O WQAWEUZTDVWTDB-UHFFFAOYSA-N 0.000 description 2
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
- KZFJYCRQWKWYJE-UHFFFAOYSA-N 1,4-dimethyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CC1=CP(C)(=O)CC1 KZFJYCRQWKWYJE-UHFFFAOYSA-N 0.000 description 1
- VLBFSRWBQYDYRF-UHFFFAOYSA-N 1,5-dimethyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CC1=CCCP1(C)=O VLBFSRWBQYDYRF-UHFFFAOYSA-N 0.000 description 1
- PSJDLMQWVMBPQE-UHFFFAOYSA-N 1-(1-chlorocyclohexa-2,4-dien-1-yl)-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound C1CC=CP1(=O)C1(Cl)CC=CC=C1 PSJDLMQWVMBPQE-UHFFFAOYSA-N 0.000 description 1
- IFDPMEFUHWICTP-UHFFFAOYSA-N 1-(2-chloroethyl)-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound ClCCP1(=O)CCC=C1 IFDPMEFUHWICTP-UHFFFAOYSA-N 0.000 description 1
- KXGNTBFJKWTSHU-UHFFFAOYSA-N 1-(2-ethylhexyl)-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CCCCC(CC)CP1(=O)CCC=C1 KXGNTBFJKWTSHU-UHFFFAOYSA-N 0.000 description 1
- ZOXNTBWGHDEDOM-UHFFFAOYSA-N 1-(4-methylphenyl)-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound C1=CC(C)=CC=C1P1(=O)C=CCC1 ZOXNTBWGHDEDOM-UHFFFAOYSA-N 0.000 description 1
- DMJIDUJBGLRWNY-UHFFFAOYSA-N 1-(chloromethyl)-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound ClCP1(=O)CCC=C1 DMJIDUJBGLRWNY-UHFFFAOYSA-N 0.000 description 1
- JSGWRKKVZHFMPZ-UHFFFAOYSA-N 1-butyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CCCCP1(=O)CCC=C1 JSGWRKKVZHFMPZ-UHFFFAOYSA-N 0.000 description 1
- YUQUHJGNZFFDAA-UHFFFAOYSA-N 1-phenyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound C=1C=CC=CC=1P1(=O)CCC=C1 YUQUHJGNZFFDAA-UHFFFAOYSA-N 0.000 description 1
- FFBJLRMDGWQPLJ-UHFFFAOYSA-N 2-dimethylphosphoryl-1-methyl-1$l^{5}-phospholane 1-oxide Chemical compound CP(C)(=O)C1CCCP1(C)=O FFBJLRMDGWQPLJ-UHFFFAOYSA-N 0.000 description 1
- MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-UHFFFAOYSA-N 0.000 description 1
- MHVLDPQOAUNEHN-UHFFFAOYSA-N COP(=O)CC1P(CCC1)(=O)C Chemical compound COP(=O)CC1P(CCC1)(=O)C MHVLDPQOAUNEHN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- OLXJCGHCKVKDLL-UHFFFAOYSA-N N=C=N.N=C=O Chemical compound N=C=N.N=C=O OLXJCGHCKVKDLL-UHFFFAOYSA-N 0.000 description 1
- ZBVOEVQTNYNNMY-UHFFFAOYSA-N O=P1=CCCC1 Chemical compound O=P1=CCCC1 ZBVOEVQTNYNNMY-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010953 base metal Substances 0.000 description 1
- QPKOILOWXGLVJS-UHFFFAOYSA-N bis(2-methylpropoxy)-oxophosphanium Chemical compound CC(C)CO[P+](=O)OCC(C)C QPKOILOWXGLVJS-UHFFFAOYSA-N 0.000 description 1
- GXVWJQNUQYSLNR-UHFFFAOYSA-N butoxy(butylsulfanyl)phosphinous acid Chemical compound P(SCCCC)(OCCCC)O GXVWJQNUQYSLNR-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- UZEFVQBWJSFOFE-UHFFFAOYSA-N dibutyl hydrogen phosphite Chemical compound CCCCOP(O)OCCCC UZEFVQBWJSFOFE-UHFFFAOYSA-N 0.000 description 1
- JMCNGFNJWDJIIV-UHFFFAOYSA-N dibutyl(oxo)phosphanium Chemical compound CCCC[P+](=O)CCCC JMCNGFNJWDJIIV-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- RJODUASCKGDMQK-UHFFFAOYSA-N diethoxy(sulfanylidene)phosphanium Chemical compound CCO[P+](=S)OCC RJODUASCKGDMQK-UHFFFAOYSA-N 0.000 description 1
- VZZJVOCVAZHETD-UHFFFAOYSA-N diethylphosphane Chemical compound CCPCC VZZJVOCVAZHETD-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- YOTZYFSGUCFUKA-UHFFFAOYSA-N dimethylphosphine Chemical compound CPC YOTZYFSGUCFUKA-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 229960002017 echothiophate Drugs 0.000 description 1
- BJOLKYGKSZKIGU-UHFFFAOYSA-N ecothiopate Chemical compound CCOP(=O)(OCC)SCC[N+](C)(C)C BJOLKYGKSZKIGU-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- DWHMMGGJCLDORC-UHFFFAOYSA-N methoxy(methyl)phosphinic acid Chemical compound COP(C)(O)=O DWHMMGGJCLDORC-UHFFFAOYSA-N 0.000 description 1
- MHERPFVRWOTBSF-UHFFFAOYSA-N methyl(phenyl)phosphane Chemical compound CPC1=CC=CC=C1 MHERPFVRWOTBSF-UHFFFAOYSA-N 0.000 description 1
- SAWKFRBJGLMMES-UHFFFAOYSA-N methylphosphine Chemical compound PC SAWKFRBJGLMMES-UHFFFAOYSA-N 0.000 description 1
- ATPGNTDARNWVLL-UHFFFAOYSA-N methylphosphonoylbenzene Chemical compound CP(=O)C1=CC=CC=C1 ATPGNTDARNWVLL-UHFFFAOYSA-N 0.000 description 1
- FEZFGASTIQVZSC-UHFFFAOYSA-N nonanoyl nonaneperoxoate Chemical compound CCCCCCCCC(=O)OOC(=O)CCCCCCCC FEZFGASTIQVZSC-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- RVZJVYCTFGOEHX-UHFFFAOYSA-N phosphetane Chemical compound C1CPC1 RVZJVYCTFGOEHX-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- GWLJTAJEHRYMCA-UHFFFAOYSA-N phospholane Chemical group C1CCPC1 GWLJTAJEHRYMCA-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide
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)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752504333 DE2504333A1 (de) | 1975-02-01 | 1975-02-01 | Substituierte cyclische phosphinoxide |
| US05/648,710 US4052484A (en) | 1975-02-01 | 1976-01-13 | Substituted cyclic phosphine oxides |
| GB3269/76A GB1536479A (en) | 1975-02-01 | 1976-01-28 | Substituted cyclic phosphine oxides and sulphides |
| BE2054787A BE838016A (fr) | 1975-02-01 | 1976-01-29 | Oxydes et sulfures de phosphines cycliques substitues et leur procede de preparation |
| JP51008029A JPS51100080A (en) | 1975-02-01 | 1976-01-29 | Chikansaretakanshikihosufuinokishido |
| FR7602655A FR2299341A1 (fr) | 1975-02-01 | 1976-01-30 | Oxydes et sulfures de phosphines cycliques substitues et leur procede de preparation |
| BR7600601A BR7600601A (pt) | 1975-02-01 | 1976-01-30 | Processo para a preparacao de oxidos de fosfina ciclicos |
| ES444779A ES444779A1 (es) | 1975-02-01 | 1976-01-30 | Procedimiento para la obtencion de oxidos de fosfinas cicli-cos. |
| DD191040A DD125574A5 (enExample) | 1975-02-01 | 1976-01-30 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752504333 DE2504333A1 (de) | 1975-02-01 | 1975-02-01 | Substituierte cyclische phosphinoxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2504333A1 true DE2504333A1 (de) | 1976-08-05 |
Family
ID=5937928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752504333 Pending DE2504333A1 (de) | 1975-02-01 | 1975-02-01 | Substituierte cyclische phosphinoxide |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4052484A (enExample) |
| JP (1) | JPS51100080A (enExample) |
| BE (1) | BE838016A (enExample) |
| BR (1) | BR7600601A (enExample) |
| DD (1) | DD125574A5 (enExample) |
| DE (1) | DE2504333A1 (enExample) |
| ES (1) | ES444779A1 (enExample) |
| FR (1) | FR2299341A1 (enExample) |
| GB (1) | GB1536479A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2927916A1 (de) * | 1979-07-11 | 1981-01-29 | Hoechst Ag | Verfahren zur herstellung von 1-oxophospholanen-chlor-hydrinen sowie einige spezielle dieser verbindungen |
| DE3319850C2 (de) * | 1983-06-01 | 1985-05-09 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung von phosphorhaltigen Cyanhydrinderivaten |
| CA1311496C (en) * | 1988-03-28 | 1992-12-15 | Allan James Robertson | 1,4-disubstituted-2,3,5,6-tetrahydroxy-1, 4-diphosphorinanes and their oxides or sulfides |
| GB2317177A (en) * | 1996-09-13 | 1998-03-18 | British Steel Plc | Organic phosphonates and metal complexes thereof for use as coating agents and especially for pretreating steel |
| WO2014140353A1 (en) * | 2013-03-14 | 2014-09-18 | Dublin City University | Methods for phosphine oxide reduction in catalytic wittig reactions |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3725466A (en) * | 1970-04-06 | 1973-04-03 | Stauffer Chemical Co | Process for the preparation of phosphorus compounds having an alkyl ether substituent and intermediates therefor |
-
1975
- 1975-02-01 DE DE19752504333 patent/DE2504333A1/de active Pending
-
1976
- 1976-01-13 US US05/648,710 patent/US4052484A/en not_active Expired - Lifetime
- 1976-01-28 GB GB3269/76A patent/GB1536479A/en not_active Expired
- 1976-01-29 BE BE2054787A patent/BE838016A/xx unknown
- 1976-01-29 JP JP51008029A patent/JPS51100080A/ja active Pending
- 1976-01-30 BR BR7600601A patent/BR7600601A/pt unknown
- 1976-01-30 ES ES444779A patent/ES444779A1/es not_active Expired
- 1976-01-30 DD DD191040A patent/DD125574A5/xx unknown
- 1976-01-30 FR FR7602655A patent/FR2299341A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| BE838016A (fr) | 1976-07-29 |
| FR2299341A1 (fr) | 1976-08-27 |
| DD125574A5 (enExample) | 1977-05-04 |
| BR7600601A (pt) | 1976-08-31 |
| US4052484A (en) | 1977-10-04 |
| ES444779A1 (es) | 1977-05-16 |
| GB1536479A (en) | 1978-12-20 |
| JPS51100080A (en) | 1976-09-03 |
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