KR101042664B1 - 디알킬주석 디알콕시드의 제조 방법 - Google Patents
디알킬주석 디알콕시드의 제조 방법 Download PDFInfo
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- KR101042664B1 KR101042664B1 KR1020097002791A KR20097002791A KR101042664B1 KR 101042664 B1 KR101042664 B1 KR 101042664B1 KR 1020097002791 A KR1020097002791 A KR 1020097002791A KR 20097002791 A KR20097002791 A KR 20097002791A KR 101042664 B1 KR101042664 B1 KR 101042664B1
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- South Korea
- Prior art keywords
- isomer
- acid
- tin
- compound
- catalyst
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 276
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 135
- 230000008569 process Effects 0.000 title claims abstract description 119
- 238000006243 chemical reaction Methods 0.000 claims abstract description 401
- 239000000203 mixture Substances 0.000 claims abstract description 390
- -1 ester compound Chemical class 0.000 claims abstract description 388
- 239000003054 catalyst Substances 0.000 claims abstract description 202
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 163
- 150000001875 compounds Chemical class 0.000 claims abstract description 132
- 229910052718 tin Inorganic materials 0.000 claims description 229
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 196
- 239000000243 solution Substances 0.000 claims description 188
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 141
- 150000003606 tin compounds Chemical class 0.000 claims description 134
- 239000002253 acid Substances 0.000 claims description 114
- 239000012974 tin catalyst Substances 0.000 claims description 102
- 238000004821 distillation Methods 0.000 claims description 93
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 64
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 62
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 59
- 150000008065 acid anhydrides Chemical class 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 58
- 239000000126 substance Substances 0.000 claims description 50
- 238000009835 boiling Methods 0.000 claims description 48
- 238000000926 separation method Methods 0.000 claims description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 239000007788 liquid Substances 0.000 claims description 41
- 239000001569 carbon dioxide Substances 0.000 claims description 39
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 39
- 239000012295 chemical reaction liquid Substances 0.000 claims description 38
- 229910020997 Sn-Y Inorganic materials 0.000 claims description 35
- 229910008859 Sn—Y Inorganic materials 0.000 claims description 35
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 32
- 239000007864 aqueous solution Substances 0.000 claims description 32
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 31
- 229910001887 tin oxide Inorganic materials 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000004423 acyloxy group Chemical group 0.000 claims description 17
- 239000011149 active material Substances 0.000 claims description 15
- 239000007789 gas Substances 0.000 claims description 15
- 239000012024 dehydrating agents Substances 0.000 claims description 14
- 238000000605 extraction Methods 0.000 claims description 14
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 14
- 239000012433 hydrogen halide Substances 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000012528 membrane Substances 0.000 claims description 12
- 230000001172 regenerating effect Effects 0.000 claims description 12
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001298 alcohols Chemical class 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 11
- 150000004703 alkoxides Chemical class 0.000 claims description 11
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 11
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 7
- 238000012545 processing Methods 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000006900 dealkylation reaction Methods 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000004064 recycling Methods 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 description 119
- 239000003921 oil Substances 0.000 description 101
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 83
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 76
- 238000012546 transfer Methods 0.000 description 67
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 58
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- 229910052751 metal Inorganic materials 0.000 description 46
- 239000002184 metal Substances 0.000 description 46
- CQQXCSFSYHAZOO-UHFFFAOYSA-L [acetyloxy(dioctyl)stannyl] acetate Chemical compound CCCCCCCC[Sn](OC(C)=O)(OC(C)=O)CCCCCCCC CQQXCSFSYHAZOO-UHFFFAOYSA-L 0.000 description 44
- 238000010926 purge Methods 0.000 description 35
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 32
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- 238000010438 heat treatment Methods 0.000 description 31
- 238000010992 reflux Methods 0.000 description 31
- RZJBYWWPIGNUSQ-UHFFFAOYSA-M CCCCCCCCC(CCCCCCCC)(CCCCCCCC)C(=O)O[Sn] Chemical compound CCCCCCCCC(CCCCCCCC)(CCCCCCCC)C(=O)O[Sn] RZJBYWWPIGNUSQ-UHFFFAOYSA-M 0.000 description 30
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- 235000011054 acetic acid Nutrition 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000010409 thin film Substances 0.000 description 27
- 238000006467 substitution reaction Methods 0.000 description 26
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 25
- 239000002904 solvent Substances 0.000 description 24
- 239000012299 nitrogen atmosphere Substances 0.000 description 20
- 239000002994 raw material Substances 0.000 description 20
- 239000013543 active substance Substances 0.000 description 19
- 238000001816 cooling Methods 0.000 description 19
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 18
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 18
- XXJIFCJOGDHOGM-UHFFFAOYSA-N 3-methylbutoxy(trioctyl)stannane Chemical compound CCCCCCCC[Sn](CCCCCCCC)(CCCCCCCC)OCCC(C)C XXJIFCJOGDHOGM-UHFFFAOYSA-N 0.000 description 16
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 16
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 235000019260 propionic acid Nutrition 0.000 description 16
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound 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 description 16
- 238000011084 recovery Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
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- DEQLXBHDWZKOKG-UHFFFAOYSA-L [dioctyl(propanoyloxy)stannyl] propanoate Chemical compound CCCCCCCC[Sn](OC(=O)CC)(OC(=O)CC)CCCCCCCC DEQLXBHDWZKOKG-UHFFFAOYSA-L 0.000 description 14
- 229910001873 dinitrogen Inorganic materials 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 13
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 13
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 13
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 12
- 125000000753 cycloalkyl group Chemical group 0.000 description 12
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 12
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 11
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- DIVTWACHZOQOBF-UHFFFAOYSA-K diacetyloxy(butyl)stannanylium;acetate Chemical compound CCCC[Sn](OC(C)=O)(OC(C)=O)OC(C)=O DIVTWACHZOQOBF-UHFFFAOYSA-K 0.000 description 10
- 150000002170 ethers Chemical class 0.000 description 10
- XAOGXQMKWQFZEM-UHFFFAOYSA-N isoamyl propanoate Chemical compound CCC(=O)OCCC(C)C XAOGXQMKWQFZEM-UHFFFAOYSA-N 0.000 description 10
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- 238000000746 purification Methods 0.000 description 9
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 8
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 8
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 8
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 8
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- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 8
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- RGCPMRIOBZXXBR-UHFFFAOYSA-N butan-1-olate;dibutyltin(2+) Chemical compound CCCCO[Sn](CCCC)(CCCC)OCCCC RGCPMRIOBZXXBR-UHFFFAOYSA-N 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
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- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 8
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 8
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- 230000009467 reduction Effects 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
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- UBEVTKIXDIYJCB-UHFFFAOYSA-M C(CCCCCCC)C(CC(=O)O[Sn])(CCCCCCCC)CCCCCCCC Chemical compound C(CCCCCCC)C(CC(=O)O[Sn])(CCCCCCCC)CCCCCCCC UBEVTKIXDIYJCB-UHFFFAOYSA-M 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
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- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 7
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 6
- WLAMNBDJUVNPJU-BYPYZUCNSA-N 2-Methylbutanoic acid Natural products CC[C@H](C)C(O)=O WLAMNBDJUVNPJU-BYPYZUCNSA-N 0.000 description 6
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- MNPJJVRGDZLJGN-UHFFFAOYSA-K [octyl-di(propanoyloxy)stannyl] propanoate Chemical compound CCCCCCCC[Sn](OC(=O)CC)(OC(=O)CC)OC(=O)CC MNPJJVRGDZLJGN-UHFFFAOYSA-K 0.000 description 6
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
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- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- 150000002763 monocarboxylic acids Chemical class 0.000 description 6
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical class CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
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- 229940005605 valeric acid Drugs 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000005194 fractionation Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
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- WQSDXGYIZLLSJT-UHFFFAOYSA-N (2,3-dipentylphenyl) N-[6-[(2,3-dipentylphenoxy)carbonylamino]hexyl]carbamate Chemical compound CCCCCC1=CC=CC(OC(=O)NCCCCCCNC(=O)OC=2C(=C(CCCCC)C=CC=2)CCCCC)=C1CCCCC WQSDXGYIZLLSJT-UHFFFAOYSA-N 0.000 description 1
- CAUVZSJOIMWVEN-UHFFFAOYSA-N (2-ethylphenyl) n-[6-[(2-ethylphenoxy)carbonylamino]hexyl]carbamate Chemical compound CCC1=CC=CC=C1OC(=O)NCCCCCCNC(=O)OC1=CC=CC=C1CC CAUVZSJOIMWVEN-UHFFFAOYSA-N 0.000 description 1
- BAYXEUGGWRMYEF-UHFFFAOYSA-N (2-methylphenyl) n-[6-[(2-methylphenoxy)carbonylamino]hexyl]carbamate Chemical compound CC1=CC=CC=C1OC(=O)NCCCCCCNC(=O)OC1=CC=CC=C1C BAYXEUGGWRMYEF-UHFFFAOYSA-N 0.000 description 1
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
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- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- AHIXTTGLRFPWJF-UHFFFAOYSA-M tributylstannyl propanoate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(=O)CC AHIXTTGLRFPWJF-UHFFFAOYSA-M 0.000 description 1
- VCSUQOHFBBQHQV-UHFFFAOYSA-N triethoxy(methyl)stannane Chemical compound CCO[Sn](C)(OCC)OCC VCSUQOHFBBQHQV-UHFFFAOYSA-N 0.000 description 1
- YUBJNHZNELHRED-UHFFFAOYSA-N triethoxy(octyl)stannane Chemical compound CCCCCCCC[Sn](OCC)(OCC)OCC YUBJNHZNELHRED-UHFFFAOYSA-N 0.000 description 1
- LZNVPMCSHYAWCM-UHFFFAOYSA-N triheptoxy(methyl)stannane Chemical compound CCCCCCCO[Sn](C)(OCCCCCCC)OCCCCCCC LZNVPMCSHYAWCM-UHFFFAOYSA-N 0.000 description 1
- NBUGXOPQIVHREY-UHFFFAOYSA-N trihexoxy(methyl)stannane Chemical compound CCCCCCO[Sn](C)(OCCCCCC)OCCCCCC NBUGXOPQIVHREY-UHFFFAOYSA-N 0.000 description 1
- DFGVXJKHJCGQFY-UHFFFAOYSA-N trihexoxy(octyl)stannane Chemical compound CCCCCCCC[Sn](OCCCCCC)(OCCCCCC)OCCCCCC DFGVXJKHJCGQFY-UHFFFAOYSA-N 0.000 description 1
- IGFKMMWLGCUHHR-UHFFFAOYSA-N trimethoxy(methyl)stannane Chemical compound CO[Sn](C)(OC)OC IGFKMMWLGCUHHR-UHFFFAOYSA-N 0.000 description 1
- VJWARDOLCXUDLG-UHFFFAOYSA-N trimethoxy(octyl)stannane Chemical compound CCCCCCCC[Sn](OC)(OC)OC VJWARDOLCXUDLG-UHFFFAOYSA-N 0.000 description 1
- QBHNUXWZXFABQY-UHFFFAOYSA-N trimethyl(octoxy)stannane Chemical compound CCCCCCCCO[Sn](C)(C)C QBHNUXWZXFABQY-UHFFFAOYSA-N 0.000 description 1
- LCQRYBJBTDKLBK-UHFFFAOYSA-N trimethyl(pentoxy)stannane Chemical compound CCCCCO[Sn](C)(C)C LCQRYBJBTDKLBK-UHFFFAOYSA-N 0.000 description 1
- FTPGGCODTXXCPZ-UHFFFAOYSA-N trimethyl(propoxy)stannane Chemical compound CCCO[Sn](C)(C)C FTPGGCODTXXCPZ-UHFFFAOYSA-N 0.000 description 1
- MZGUIAFRJWSYJJ-UHFFFAOYSA-M trimethylstannanylium;bromide Chemical compound C[Sn](C)(C)Br MZGUIAFRJWSYJJ-UHFFFAOYSA-M 0.000 description 1
- XZVPFLCTEMAYFI-UHFFFAOYSA-M trimethylstannyl acetate Chemical compound CC(=O)O[Sn](C)(C)C XZVPFLCTEMAYFI-UHFFFAOYSA-M 0.000 description 1
- VZDFJPLLAYRLHV-UHFFFAOYSA-M trimethylstannyl butanoate Chemical compound CCCC(=O)O[Sn](C)(C)C VZDFJPLLAYRLHV-UHFFFAOYSA-M 0.000 description 1
- PCOUHFKVBMVPCD-UHFFFAOYSA-M trimethylstannyl pentanoate Chemical compound CCCCC(=O)O[Sn](C)(C)C PCOUHFKVBMVPCD-UHFFFAOYSA-M 0.000 description 1
- WYFAXFPVEGZJMO-UHFFFAOYSA-M trimethylstannyl propanoate Chemical compound CCC(=O)O[Sn](C)(C)C WYFAXFPVEGZJMO-UHFFFAOYSA-M 0.000 description 1
- PPVVDBYJRDYGRY-UHFFFAOYSA-N trioctyl(pentoxy)stannane Chemical compound CCCCCCCC[Sn](CCCCCCCC)(CCCCCCCC)OCCCCC PPVVDBYJRDYGRY-UHFFFAOYSA-N 0.000 description 1
- OIJGXZUDLIGCKX-UHFFFAOYSA-N trioctyl(propoxy)stannane Chemical compound CCCCCCCC[Sn](CCCCCCCC)(CCCCCCCC)OCCC OIJGXZUDLIGCKX-UHFFFAOYSA-N 0.000 description 1
- HJNBKKMVQZKRNU-UHFFFAOYSA-M trioctylstannyl acetate Chemical compound CCCCCCCC[Sn](CCCCCCCC)(CCCCCCCC)OC(C)=O HJNBKKMVQZKRNU-UHFFFAOYSA-M 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages
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- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
Description
Claims (39)
- 디알킬주석 화합물의 제조 방법으로서,디알킬주석 촉매를 이용하여 에스테르 화합물을 제조할 때에 생성되는, 디알킬주석 촉매의 실활체 조성물로, 알킬기 재분배 반응 및 탈알킬기 반응 중 하나 이상의 반응을 실시하는 공정을 포함하고,상기 디알킬주석 촉매의 실활체의 주석 원자에 결합하고 있는, 디알킬주석 촉매에서 유래하는 알킬기 이외의 기 중 적어도 하나의 치환기에 대한 공역산의 pKa가 0∼6.8인 경우,상기 알킬기 재분배 반응이, Sn-Y 결합을 갖는 유기 주석 화합물(여기서, Y는 Y에 수소 원자가 부가된 Y의 공역산인 HY의 pKa가 0∼6.8인 Y임)을 가열 처리하는 알킬기 재분배 반응이며,상기 디알킬주석 촉매의 실활체의 주석 원자에 결합하고 있는, 디알킬주석 촉매에서 유래하는 알킬기 이외의 기 중 적어도 하나의 치환기에 대한 공역산의 pKa가 6.8보다 크고 25 이하인 경우,상기 알킬기 재분배 반응이공정 (A): 상기 실활체의 배위자(상기 디알킬주석 촉매에서 유래하고, 주석에 결합하고 있는 알킬기를 제외함)의 일부 또는 전부를 치환기 Y로 치환하여, Sn-Y 결합을 갖는 유기 주석 화합물을 얻는 공정;공정 (B): 공정 (A)에서 얻어진 Sn-Y 결합을 갖는 유기 주석 화합물(여기서 Y는 Y에 수소 원자가 부가된 Y의 공역산인 HY의 pKa가 0∼6.8인 Y임)을 가열 처리하는 공정을 포함하는 것인 제조 방법.
- 제1항에 있어서, 상기 디알킬주석 촉매가 식 (1)로 나타내어지는 디알킬주석 화합물 및 식 (2)로 나타내어지는 테트라알킬디스탄옥산 화합물로 이루어지는 군에서 선택되는 적어도 1종의 화합물인 제조 방법:(식에서, R1 및 R2는 각각 독립적으로 직쇄형 또는 분기쇄형의 탄소수 1∼12의 알킬기를 나타내고,X1 및 X2는 각각 독립적으로 알콕시기, 아실옥실기 및 할로겐 원자로 이루어지는 군에서 선택되는 적어도 1종의 치환기를 나타내고,a 및 b는 각각 0∼2의 정수로, a+b=2이며,c 및 d는 각각 0∼2의 정수로, c+d=2임)(식에서, R3, R4, R5 및 R6은 각각 독립적으로 직쇄형 또는 분기쇄형의 탄소수 1∼12의 알킬기를 나타내고,X3 및 X4는 각각 독립적으로 알콕시기, 아실옥실기 및 할로겐 원자로 이루어지는 군에서 선택되는 적어도 1종의 치환기를 나타내고,e, f, g, h는 각각 0∼2의 정수로, e+f=2, g+h=2임).
- 제2항에 있어서, 상기 식 (1) 및 (2)에 있어서, X1, X2, X3 및 X4를 구성하는 탄소 원자의 수가 O∼12의 정수에서 선택되는 수인 제조 방법.
- 제1항 내지 제3항 중 어느 한 항에 있어서, 상기 에스테르 화합물이 카르복실산에스테르, 카르바민산에스테르 및 이소시안산에스테르로 이루어지는 군에서 선택되는 적어도 1종의 화합물인 제조 방법.
- 제4항에 있어서, 상기 카르복실산에스테르가 탄산에스테르인 제조 방법.
- 제5항에 있어서, 상기 디알킬주석 촉매의 실활체 조성물이, 이산화탄소와 디 알킬주석 촉매로부터 탄산에스테르를 제조하는 과정에서 생성되는 디알킬주석 촉매의 실활체를 함유하는 조성물인 제조 방법.
- 제1항에 있어서, 상기 디알킬주석 촉매의 실활체가 디알킬주석 촉매의 열실활체인 제조 방법.
- 제1항에 있어서, 상기 디알킬주석 촉매의 실활체가 상기 디알킬주석 촉매에서 유래하고, 하나의 주석 원자에 결합하는 알킬기의 수가 디알킬주석 촉매의 하나의 주석 원자에 결합하고 있는 알킬기의 수와 다른, 디알킬주석 촉매의 실활체인 제조 방법.
- 제1항에 있어서, 상기 디알킬주석 촉매의 실활체의 적어도 1종이 트리알킬주석 화합물인 제조 방법.
- 제8항에 있어서, 상기 디알킬주석 촉매의 실활체가, 트리알킬주석 화합물 및 중클로로포름 용액 중에서 119Sn-NMR에 의해 분석했을 때에 테트라메틸주석 기준으로 -220∼-610 ppm에 화학 시프트를 보이는 주석 원자를 함유하는 유기 주석 화합물인 제조 방법.
- 제10항에 있어서, 상기 디알킬주석 촉매의 실활체 조성물로부터, 트리알킬주석 화합물을 포함하는 조성물과, 중클로로포름 용액 중에서 119Sn-NMR에 의해 분석했을 때에 테트라메틸주석 기준으로 -220∼-610 ppm에 화학 시프트를 보이는 주석 원자를 함유하는 화합물을 포함하는 조성물로 분리하는 공정을 더 포함하는 제조 방법.
- 제11항에 있어서, 상기 분리 공정이 증류 분리, 추출 분리, 막 분리로 이루어지는 군에서 선택되는 적어도 하나의 방법에 의해 행해지는 것인 제조 방법.
- 삭제
- 삭제
- 제1항에 있어서, 상기 공정 (A)가상기 디알킬주석 촉매의 실활체 조성물과 하기 식 (3)으로 나타내어지는 산 및 하기 식 (4)로 나타내어지는 산무수물 중 하나 이상을 반응시켜, 1개의 주석 원자에 3개의 알킬기와 1개의 산 또는 산무수물에서 유래하는 기 Y가 결합한 Sn-Y 결합을 갖는 유기 주석 화합물과, 1개의 주석 원자에 1개의 알킬기와 1∼3의 정수에서 선택되는 수의 산 또는 산무수물에서 유래하는 기 Y가 결합한 Sn-Y 결합을 갖는 유기 주석 화합물을 제조하는 공정을 포함하는 것인 제조 방법:(식에서, Y는 Y에 수소 원자가 부가된 Y의 공역산인 HY의 pKa가 0∼6.8인 Y임)(식에서, Y는 Y에 수소 원자가 부가된 Y의 공역산인 HY의 pKa가 0∼6.8인 Y이고, O는 산소 원자를 나타냄).
- 제15항에 있어서, 상기 공정 (A)에서 산을 이용했을 때에 생성되는 물을, 탈수제에 의한 제거, 증류 분리, 막 분리로 이루어지는 군에서 선택되는 적어도 하나의 방법에 의해서 제거하면서 행하는 것인 제조 방법.
- 제1항에 있어서, 상기 탈알킬기 반응이, 디알킬주석 촉매의 실활체로부터 알킬기를 탈리시켜 Sn-Y 결합(여기서, Y는 Y에 수소 원자가 부가된 Y의 공역산인 HY의 pKa가 0∼6.8인 Y임)을 형성하는 공정을 포함하는 것인 제조 방법.
- 제9항에 있어서, 상기 탈알킬기 반응이, 디알킬주석 촉매의 실활체 조성물에 함유되는 트리알킬주석 화합물로부터 1개의 알킬기를 탈리시켜 1개의 Sn-Y 결합을 형성하여, Sn-Y 결합을 갖는 디알킬주석 화합물(여기서, Y는 Y에 수소 원자가 부가된 Y의 공역산인 HY의 pKa가 0∼6.8인 Y임)을 얻는 것인 제조 방법.
- 제15항 또는 제19항에 있어서, 상기 산 또는 산무수물이, 60℃에서 액체 또는 기체인 제조 방법.
- 제20항에 있어서, 상기 산이 할로겐화수소산인 제조 방법.
- 제20항에 있어서, 상기 산이 할로겐화수소인 제조 방법.
- 제20항에 있어서, 상기 산이 유기산인 제조 방법.
- 제23항에 있어서, 상기 유기산이 카르복실산인 제조 방법.
- 제20항에 있어서, 상기 산무수물의 표준 비점이 300℃ 이하인 제조 방법.
- 제25항에 있어서, 상기 산무수물이 무수초산 또는 무수말레산인 제조 방법.
- 제1항에 있어서, 상기 디알킬주석 화합물이, 하나의 주석 원자에 2개의 디알킬주석 촉매에서 유래하는 알킬기가 결합하고, 동시에, 적어도 1개의 Sn-Y 결합(여기서, Y는 Y에 수소 원자가 부가된 Y의 공역산인 HY의 pKa가 0∼6.8인 Y임)을 갖는 것인 제조 방법.
- 제27항에 있어서, 상기 디알킬주석 화합물이, 식 (7)로 나타내어지는 디알킬주석 화합물 및 식 (8)로 나타내어지는 테트라알킬디스탄옥산 화합물로 이루어지는 군에서 선택되는 적어도 1종의 화합물인 제조 방법:(식에서, R7 및 R8은 디알킬주석 촉매에서 유래하는 기이며, 각각 독립적으로 직쇄형 또는 분기형의 탄소수 1∼12의 알킬기를 나타내고,Y는 디알킬주석 촉매에서 유래하는 기, 또는 산(HY) 또는 산무수물(YOY)에서 유래하는 기로서, Y에 수소 원자가 부가된 Y의 공역산인 HY의 pKa가 0∼6.8인 Y이며,i 및 j는 각각 0∼2의 정수로, i+j=2임)(식에서, R9, R10, R11 및 R12는 디알킬주석 촉매에서 유래하는 기이며, 각각 독립적으로 직쇄형 또는 분기형의 탄소수 1∼12의 알킬기를 나타내고,Y는 디알킬주석 촉매에서 유래하는 기, 또는 산(HY) 또는 산무수물(YOY)에서 유래하는 기로서, Y에 수소 원자가 부가된 Y의 공역산인 HY의 pKa가 0∼6.8인 Y이고,k, l, m, n은 각각 0∼2의 정수로, k+l=2, m+n=2임).
- 제1항에 있어서, 상기 공정 (B) 후에공정 (I): Sn-Y 결합을 갖는 디알킬주석 화합물의 치환기 Y를, 알콕시기, 아실옥실기 및 할로겐 원자로 이루어지는 군에서 선택되는 적어도 1종의 치환기로 치환하는 공정을 포함하는 제조 방법.
- 제29항에 있어서, 상기 공정 (I)이공정 (I-1): Sn-Y 결합을 갖는 디알킬주석 화합물에 알칼리 수용액을 가하여 가수분해하여 디알킬산화주석을 함유하는 조성물을 얻는 공정;공정 (I-2): 상기 공정 (I-1)에서 얻어진 디알킬산화주석을 함유하는 조성물 과, 알코올, 카르복실산 및 할로겐화수소로 이루어지는 군에서 선택되는 적어도 1종의 화합물을 반응시켜, 발생하는 물을 함유하는 성분을 반응액으로부터 제거하는 공정을 포함하는 것인 제조 방법.
- 제30항에 있어서, 상기 알칼리 수용액이 수산화나트륨 수용액, 수산화칼륨 수용액, 탄산칼륨 수용액 및 탄산나트륨 수용액으로 이루어지는 군에서 선택되는 적어도 하나의 알칼리 수용액인 제조 방법.
- 제30항에 있어서, 상기 공정 (I-2)에 있어서, 디알킬산화주석을 함유하는 조성물과 반응시키는 화합물이 알코올이며, 디알킬주석알콕시드 화합물을 얻는 공정인 제조 방법.
- 제6항에 있어서, 상기 탄산에스테르를 제조하는 과정이공정 (1): 이산화탄소와 디알킬주석 촉매를 반응시켜, 탄산에스테르를 함유하는 반응액을 얻는 공정;공정 (2): 상기 반응액으로부터 탄산에스테르를 분리하여, 잔류액을 얻는 공정;공정 (3): 상기 잔류액과 알코올을 반응시켜 생성되는 물을 계 밖으로 제거하여 디알킬주석 촉매를 재생하는 공정;공정 (4): 공정 (3)에서 얻어진 디알킬주석 촉매를 공정 (1)로 리사이클하는 공정을 포함하는 것인 제조 방법.
- 제33항에 있어서, 상기 탄산에스테르를 제조하는 과정에서 생성되는 디알킬주석 촉매의 실활체 조성물로부터, 알킬기 재분배 반응 및 탈알킬기 반응 중 하나 이상의 반응을 하여 디알킬주석 촉매를 재생하는 공정을,상기 공정 (2) 및 공정 (3) 중 하나 이상의 공정 후에 실시하여, 재생된 디알킬주석 촉매를 상기 공정 (4) 및 공정 (1) 중 하나 이상의 공정의 디알킬주석 촉매로서 리사이클 사용하는 것을 더 포함하는 것인 제조 방법.
- 제34항에 있어서, 상기 디알킬주석 촉매를 재생하는 공정이, 공정 (I): Sn-Y 결합을 갖는 디알킬주석 화합물의 치환기 Y를 아실옥실기로 치환하는 공정인 제조 방법.
- 제1항에 있어서, 상기 디알킬주석 촉매가 디알킬주석알콕시드 화합물인 제조 방법.
- 제36항에 있어서, 상기 디알킬주석 촉매가 디알킬주석알콕시드 화합물로서, 식 (1) 또는 식 (2)로 나타내어지는 화합물 중 X1, X2, X3 및 X4가 알콕시기인 화합물인 제조 방법:(식에서, R1 및 R2는 각각 독립적으로 직쇄형 또는 분기쇄형의 탄소수 1∼12의 알킬기를 나타내고,X1 및 X2는 각각 독립적으로 알콕시기, 아실옥실기 및 할로겐 원자로 이루어지는 군에서 선택되는 적어도 1종의 치환기를 나타내고,a 및 b는 각각 0∼2의 정수로, a+b=2이며,c 및 d는 각각 0∼2의 정수로, c+d=2임)(식에서, R3, R4, R5 및 R6은 각각 독립적으로 직쇄형 또는 분기쇄형의 탄소수 1∼12의 알킬기를 나타내고,X3 및 X4는 각각 독립적으로 알콕시기, 아실옥실기 및 할로겐 원자로 이루어지는 군에서 선택되는 적어도 1종의 치환기를 나타내고,e, f, g, h는 각각 0∼2의 정수로, e+f=2, g+h=2임).
- 제37항에 있어서, 상기 디알킬주석 촉매가 디알킬주석알콕시드로서, 상기 식 (1) 또는 식 (2)로 나타내어지는 화합물 중 R1, R2, R3, R4, R5 및 R6이 동시에 n-부틸기 또는 n-옥틸기인 제조 방법.
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