ES2562226T3 - Procedimiento para la preparación de ácidos dialquil-fosfínicos mono-funcionalizados y de sus ésteres y sales, y su utilización - Google Patents

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Publication number

ES2562226T3

ES2562226T3 ES09778844.2T ES09778844T ES2562226T3 ES 2562226 T3 ES2562226 T3 ES 2562226T3 ES 09778844 T ES09778844 T ES 09778844T ES 2562226 T3 ES2562226 T3 ES 2562226T3

Authority

ES

Spain

Prior art keywords

acid

salts

catalyst

mono

methyl

Prior art date

2008-12-19

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.)

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• 150000003839 salts Chemical class 0.000 title claims abstract description 81
• 238000000034 method Methods 0.000 title claims abstract description 66
• 230000008569 process Effects 0.000 title claims abstract description 57
• 150000002148 esters Chemical class 0.000 title claims abstract description 55
• 238000002360 preparation method Methods 0.000 title claims abstract description 21
• 150000003009 phosphonic acids Chemical class 0.000 title claims description 12
• -1 pentyl glycol Chemical compound 0.000 claims abstract description 164
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 70
• 239000003054 catalyst Substances 0.000 claims abstract description 59
• 150000001875 compounds Chemical class 0.000 claims abstract description 53
• 239000002253 acid Substances 0.000 claims abstract description 46
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 42
• 229910052723 transition metal Inorganic materials 0.000 claims abstract description 38
• 150000003624 transition metals Chemical class 0.000 claims abstract description 38
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical group OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 28
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 28
• 229910052782 aluminium Inorganic materials 0.000 claims abstract description 25
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 24
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 24
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical group OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 24
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 21
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 20
• 229910052700 potassium Inorganic materials 0.000 claims abstract description 20
• 229910052725 zinc Inorganic materials 0.000 claims abstract description 20
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
• 239000011734 sodium Substances 0.000 claims abstract description 19
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 18
• 229910052708 sodium Inorganic materials 0.000 claims abstract description 18
• 229910052742 iron Inorganic materials 0.000 claims abstract description 17
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 16
• 229910052791 calcium Inorganic materials 0.000 claims abstract description 16
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical group CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims abstract description 15
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 15
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims abstract description 15
• 239000011591 potassium Substances 0.000 claims abstract description 15
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Chemical group OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 15
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical group OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 14
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical group OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract description 14
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 14
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 14
• 229910052749 magnesium Inorganic materials 0.000 claims abstract description 14
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Chemical group OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 14
• 229910052719 titanium Inorganic materials 0.000 claims abstract description 14
• 239000003446 ligand Substances 0.000 claims abstract description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
• IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical group CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims abstract description 12
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 12
• 229910052684 Cerium Inorganic materials 0.000 claims abstract description 11
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 11
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 11
• 229910052744 lithium Inorganic materials 0.000 claims abstract description 11
• 150000003623 transition metal compounds Chemical class 0.000 claims abstract description 10
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical group OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims abstract description 9
• 125000003118 aryl group Chemical group 0.000 claims abstract description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 9
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims abstract description 9
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims abstract description 8
• 235000011054 acetic acid Nutrition 0.000 claims abstract description 8
• 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 8
• 235000015165 citric acid Nutrition 0.000 claims abstract description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 8
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims abstract description 8
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical group OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 8
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 8
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 7
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 7
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical group O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 7
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 7
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Chemical group [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims abstract description 7
• 235000010323 ascorbic acid Nutrition 0.000 claims abstract description 7
• 239000011668 ascorbic acid Chemical group 0.000 claims abstract description 7
• 229960005070 ascorbic acid Drugs 0.000 claims abstract description 7
• 235000019253 formic acid Nutrition 0.000 claims abstract description 7
• 239000001530 fumaric acid Chemical group 0.000 claims abstract description 7
• 235000011087 fumaric acid Nutrition 0.000 claims abstract description 7
• 239000004310 lactic acid Chemical group 0.000 claims abstract description 7
• 235000014655 lactic acid Nutrition 0.000 claims abstract description 7
• 239000011976 maleic acid Chemical group 0.000 claims abstract description 7
• 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 7
• BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims abstract description 7
• 235000019260 propionic acid Nutrition 0.000 claims abstract description 7
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical group O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims abstract description 7
• SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 claims abstract description 7
• 239000011975 tartaric acid Chemical group 0.000 claims abstract description 7
• 235000002906 tartaric acid Nutrition 0.000 claims abstract description 7
• MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 claims abstract description 7
• POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims abstract description 6
• 235000021314 Palmitic acid Nutrition 0.000 claims abstract description 6
• 235000021355 Stearic acid Nutrition 0.000 claims abstract description 6
• WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Chemical group CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims abstract description 6
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims abstract description 6
• 239000008117 stearic acid Chemical group 0.000 claims abstract description 6
• CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical group CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 claims abstract description 6
• LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 claims abstract description 6
• WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 claims abstract description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 5
• 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 5
• 229910000103 lithium hydride Inorganic materials 0.000 claims abstract description 5
• DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims abstract description 5
• 239000012279 sodium borohydride Substances 0.000 claims abstract description 5
• 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 5
• 239000012312 sodium hydride Substances 0.000 claims abstract description 5
• 229910000104 sodium hydride Inorganic materials 0.000 claims abstract description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 5
• YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 claims abstract description 4
• BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 claims abstract description 4
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 4
• UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims abstract description 4
• RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims abstract description 4
• 239000012280 lithium aluminium hydride Substances 0.000 claims abstract 2
• 238000006243 chemical reaction Methods 0.000 claims description 70
• 229910052751 metal Inorganic materials 0.000 claims description 49
• 239000002184 metal Substances 0.000 claims description 49
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
• 229920000642 polymer Polymers 0.000 claims description 33
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 28
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 28
• 150000003003 phosphines Chemical class 0.000 claims description 28
• 239000003063 flame retardant Substances 0.000 claims description 27
• 239000004952 Polyamide Substances 0.000 claims description 25
• 229920002647 polyamide Polymers 0.000 claims description 25
• 229920000728 polyester Polymers 0.000 claims description 25
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 20
• 239000003795 chemical substances by application Substances 0.000 claims description 19
• RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 18
• XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
• 150000002739 metals Chemical class 0.000 claims description 18
• 150000001298 alcohols Chemical class 0.000 claims description 15
• 229910052759 nickel Inorganic materials 0.000 claims description 15
• 238000000465 moulding Methods 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
• 239000000654 additive Substances 0.000 claims description 13
• 125000002947 alkylene group Chemical group 0.000 claims description 13
• 229910052718 tin Inorganic materials 0.000 claims description 13
• 229910052726 zirconium Inorganic materials 0.000 claims description 13
• 241000132092 Aster Species 0.000 claims description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 12
• 239000000835 fiber Substances 0.000 claims description 11
• 150000002736 metal compounds Chemical class 0.000 claims description 11
• 229910052763 palladium Inorganic materials 0.000 claims description 11
• 239000012757 flame retardant agent Substances 0.000 claims description 10
• 229910052697 platinum Inorganic materials 0.000 claims description 10
• 239000003381 stabilizer Substances 0.000 claims description 8
• 229920002678 cellulose Polymers 0.000 claims description 6
• 235000010980 cellulose Nutrition 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 229910052787 antimony Inorganic materials 0.000 claims description 5
• 229910052703 rhodium Inorganic materials 0.000 claims description 5
• 239000010948 rhodium Substances 0.000 claims description 5
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 5
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
• 239000003822 epoxy resin Substances 0.000 claims description 4
• 229910052732 germanium Inorganic materials 0.000 claims description 4
• LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 4
• 229910052748 manganese Inorganic materials 0.000 claims description 4
• 229920000647 polyepoxide Polymers 0.000 claims description 4
• 229920002635 polyurethane Polymers 0.000 claims description 4
• 239000004814 polyurethane Substances 0.000 claims description 4
• 229920006395 saturated elastomer Polymers 0.000 claims description 4
• 229910052712 strontium Inorganic materials 0.000 claims description 4
• 239000001913 cellulose Substances 0.000 claims description 3
• 239000003431 cross linking reagent Substances 0.000 claims description 3
• 229910017464 nitrogen compound Inorganic materials 0.000 claims description 3
• 150000002830 nitrogen compounds Chemical class 0.000 claims description 3
• 238000006116 polymerization reaction Methods 0.000 claims description 3
• 229920006337 unsaturated polyester resin Polymers 0.000 claims description 3
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
• 230000000996 additive effect Effects 0.000 claims description 2
• 239000011230 binding agent Substances 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 238000004140 cleaning Methods 0.000 claims description 2
• 238000000576 coating method Methods 0.000 claims description 2
• 230000007797 corrosion Effects 0.000 claims description 2
• 238000005260 corrosion Methods 0.000 claims description 2
• 239000004744 fabric Substances 0.000 claims description 2
• 238000005470 impregnation Methods 0.000 claims description 2
• 239000002480 mineral oil Substances 0.000 claims description 2
• 230000004048 modification Effects 0.000 claims description 2
• 238000012986 modification Methods 0.000 claims description 2
• 150000002829 nitrogen Chemical class 0.000 claims description 2
• 150000003008 phosphonic acid esters Chemical class 0.000 claims description 2
• 229920006149 polyester-amide block copolymer Polymers 0.000 claims description 2
• 229910052707 ruthenium Inorganic materials 0.000 claims description 2
• 239000003352 sequestering agent Substances 0.000 claims description 2
• 230000007704 transition Effects 0.000 claims description 2
• 239000002966 varnish Substances 0.000 claims description 2
• 238000005406 washing Methods 0.000 claims description 2
• 239000002023 wood Substances 0.000 claims description 2
• 239000003223 protective agent Substances 0.000 claims 1
• 150000001336 alkenes Chemical class 0.000 abstract description 13
• ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 abstract description 13
• 150000007513 acids Chemical class 0.000 abstract description 12
• 229910052760 oxygen Inorganic materials 0.000 abstract description 6
• 125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract description 2
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 52
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
• 239000002904 solvent Substances 0.000 description 32
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 25
• 229910000073 phosphorus hydride Inorganic materials 0.000 description 24
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 19
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
• 239000000203 mixture Substances 0.000 description 18
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
• 239000011701 zinc Substances 0.000 description 17
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 239000007983 Tris buffer Substances 0.000 description 14
• 239000011575 calcium Substances 0.000 description 14
• 239000000243 solution Substances 0.000 description 14
• 229910052698 phosphorus Inorganic materials 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• 229910052739 hydrogen Inorganic materials 0.000 description 12
• 239000011777 magnesium Substances 0.000 description 12
• 239000000463 material Substances 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• 229940083542 sodium Drugs 0.000 description 12
• 239000011135 tin Substances 0.000 description 12
• 239000005062 Polybutadiene Substances 0.000 description 11
• 239000012752 auxiliary agent Substances 0.000 description 11
• 239000012071 phase Substances 0.000 description 11
• 239000011574 phosphorus Substances 0.000 description 11
• 229920002857 polybutadiene Polymers 0.000 description 11
• 238000010992 reflux Methods 0.000 description 11
• 239000010936 titanium Substances 0.000 description 11
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 10
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
• ZRUWFKRETRELPY-UHFFFAOYSA-N azane;nickel(2+) Chemical compound N.[Ni+2] ZRUWFKRETRELPY-UHFFFAOYSA-N 0.000 description 10
• WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
• LYYXRDZATAMURV-UHFFFAOYSA-N ethylphosphonous acid Chemical compound CCP(O)O LYYXRDZATAMURV-UHFFFAOYSA-N 0.000 description 10
• 150000007522 mineralic acids Chemical class 0.000 description 10
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
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