CN109593188A - 一种基于强碱性离子液体高效催化制备聚碳酸酯的方法 - Google Patents
一种基于强碱性离子液体高效催化制备聚碳酸酯的方法 Download PDFInfo
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- CN109593188A CN109593188A CN201811299077.8A CN201811299077A CN109593188A CN 109593188 A CN109593188 A CN 109593188A CN 201811299077 A CN201811299077 A CN 201811299077A CN 109593188 A CN109593188 A CN 109593188A
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- polycarbonate
- dihydroxy
- dihydroxy compounds
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- ZPCHCIABIAQKQB-UHFFFAOYSA-M [OH-].C(CCC)[N+](CCCC)(CCCC)CCCC.[P] Chemical compound [OH-].C(CCC)[N+](CCCC)(CCCC)CCCC.[P] ZPCHCIABIAQKQB-UHFFFAOYSA-M 0.000 description 1
- ASNUIRXIDLSZNN-UHFFFAOYSA-N [OH-].[PH4][NH3+] Chemical compound [OH-].[PH4][NH3+] ASNUIRXIDLSZNN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- ITHZDDVSAWDQPZ-UHFFFAOYSA-L barium acetate Chemical compound [Ba+2].CC([O-])=O.CC([O-])=O ITHZDDVSAWDQPZ-UHFFFAOYSA-L 0.000 description 1
- 229940112016 barium acetate Drugs 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- UCVMQZHZWWEPRC-UHFFFAOYSA-L barium(2+);hydrogen carbonate Chemical compound [Ba+2].OC([O-])=O.OC([O-])=O UCVMQZHZWWEPRC-UHFFFAOYSA-L 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- YTEOYNARBVOWSW-UHFFFAOYSA-N hexyl(tetradecyl)phosphanium bromide Chemical compound [Br-].C(CCCCC)[PH2+]CCCCCCCCCCCCCC YTEOYNARBVOWSW-UHFFFAOYSA-N 0.000 description 1
- LVZNJBREDBWRSO-UHFFFAOYSA-N hexyl(tetradecyl)phosphanium hydroxide Chemical class [OH-].C(CCCCC)[PH2+]CCCCCCCCCCCCCC LVZNJBREDBWRSO-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- BDAGIHXWWSANSR-NJFSPNSNSA-N hydroxyformaldehyde Chemical compound O[14CH]=O BDAGIHXWWSANSR-NJFSPNSNSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 229940031993 lithium benzoate Drugs 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- HGPXWXLYXNVULB-UHFFFAOYSA-M lithium stearate Chemical compound [Li+].CCCCCCCCCCCCCCCCCC([O-])=O HGPXWXLYXNVULB-UHFFFAOYSA-M 0.000 description 1
- LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 description 1
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
- 239000002370 magnesium bicarbonate Substances 0.000 description 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- WJMMDJOFTZAHHS-UHFFFAOYSA-L strontium;carbonic acid;carbonate Chemical group [Sr+2].OC([O-])=O.OC([O-])=O WJMMDJOFTZAHHS-UHFFFAOYSA-L 0.000 description 1
- RXSHXLOMRZJCLB-UHFFFAOYSA-L strontium;diacetate Chemical compound [Sr+2].CC([O-])=O.CC([O-])=O RXSHXLOMRZJCLB-UHFFFAOYSA-L 0.000 description 1
- FRKHZXHEZFADLA-UHFFFAOYSA-L strontium;octadecanoate Chemical compound [Sr+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O FRKHZXHEZFADLA-UHFFFAOYSA-L 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical class C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- QPUSETZNLGIEOG-UHFFFAOYSA-N triphenyl(2-triphenylphosphaniumylethyl)phosphanium Chemical class C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 QPUSETZNLGIEOG-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/307—General preparatory processes using carbonates and phenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- 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
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/305—General preparatory processes using carbonates and alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
本发明涉及一种基于强碱性离子液体高效催化制备聚碳酸酯的方法,其特征在于使用由季磷为阳离子、氨基酸根为阴离子构成的离子液体为催化剂,高效催化以二羟基化合物和碳酸二酯为原料的反应制备芳香族或脂肪族聚碳酸酯。离子液体催化剂用量为二羟基化合物质量的1×10‑6~2%,在预聚阶段反应温度为100~200℃、压力为20kPa~常压,反应时间0.5h~6h;在缩聚阶段,反应温度为220~280℃、压力为20Pa~300Pa,反应时间0.1h~5h。本合成方法具有催化剂与原料相溶性好,用量少、活性高,产物聚碳酸酯分子量高的特点。
Description
技术领域
本发明属于绿色高效催化技术领域,涉及一种基于强碱性离子液体高效催化制备聚碳酸酯的方法,具体地说,使用由季磷为阳离子、氨基酸根为阴离子构成的离子液体为催化剂,催化以二羟基化合物和碳酸二酯为原料的反应制备聚碳酸酯。
背景技术
聚碳酸酯(PC)是分子链中含有碳酸酯基的一类高分子化合物的总称。聚碳酸酯具有优良的透光性、较高的玻璃化转变温度、理想的可化学修饰性、易于物理改性,以及良好的冲击韧性、电绝缘性、抗蠕变性、生理惰性、耐候性等一系列优点,使其成为工程塑料中发展最快的品种,受到了世界各工业大国的极大关注。
聚碳酸酯的合成有光气法和非光气法两种方法,光气法由于使用了剧毒的光气为原料,不符合现代绿色化工发展的需求,而非光气法一般由碳酸二酯与二羟基化合物在催化剂的作用下通过熔融缩聚而得。非光气法制备聚碳酸酯的催化剂一般为碱性化合物,包括无机碱、有机碱以及离子液体等。如CN1053246公开了以碱金属、碱土金属化合物,含氮有机物以及硼酸酯等催化剂制备聚碳酸酯,包括碱金属化合物:氢氧化钠、氢氧化钾、氢氧化锂、碳酸氢钠、碳酸氢钾、碳酸氢锂、碳酸钠、碳酸钾、碳酸锂、乙酸钠、乙酸钾、乙酸锂、硬脂酸钠、硬脂酸钾、硬脂酸锂、硼氢化钠、硼氢化锂、硼酸钠、苯甲酸钠、苯甲酸钾、苯甲酸锂、磷酸氢二钠、磷酸氢二钾、磷酸氢二锂、双酚A的二钠、二钾和二锂盐以及苯酚的钠钾锂盐;碱土金属化合物:氢氧化钙、氢氧化钡、氢氧化镁、氢氧化锶、碳酸氢钙、碳酸氢钡、碳酸氢镁、碳酸氢锶、碳酸钙、碳酸钡、碳酸镁、碳酸锶、乙酸钙、乙酸钡、乙酸镁、乙酸锶、硬脂酸钙、硬脂酸钡、硬脂酸镁、硬脂酸锶;高温下容易分解或挥发的含氮化合物,具体为含有烷基、芳基或芳烷基的氢氧化铵:四甲基氢氧化铵、四乙基氢氧化铵、四丁基氢氧化铵、三甲基苄基氢氧化铵;叔胺:三甲胺、三乙胺、二甲基苄胺、三苯胺;由R2NH(其中R是烷基,例如甲基或乙基,或芳基,例如苯基或甲苯基)所代表的仲胺;由RNH2所代表的伯胺;咪唑:α-甲基咪唑,2-苯基咪唑;碱性盐:氨水,硼氢化四甲铵,硼氢化四丁铵、四苯基硼酸四丁铵、四苯基硼酸四甲铵。硼酸化合物:硼酸酯由通式B(OR)n(OH)3-n(其中R是烷基,n是1、2或3)所代表的那些:硼酸三甲酯、硼酸三乙酯、硼酸三丁酯、硼酸三己酯、硼酸三庚酯、硼酸三苯酯、硼酸三甲苯酯、硼酸三萘酯。CN1088946公开了制备聚碳酸酯的催化剂:碱性含氮化合物,碱金属化合物,碱土金属化合物,硼酸盐或选自给电子胺及其盐的化合物。CN1127265公开了以季鏻盐化合物或其与碱金属化合物的混合物为催化剂制备聚碳酸酯。CN1172490公开了以季鏻盐,如2,2-双(4-羟基苯基)丙烷的二(四苯基)鏻盐、二溴化亚乙基双(三苯基鏻)、双(四苯基硼酸)三亚甲基双(三苯基鏻)为催化剂制备聚碳酸酯。CN1286710公开了含磷碱性化合物,包括三价磷化合物如R93P或(R9O)3P(R9表示氢原子或有机基团)为催化剂制备聚碳酸酯。CN1694915公开了具有芳烷基基团的正膦基氢氧化铵为催化剂制备聚碳酸酯。CN101125917公开了由乙酰丙酮基金属配合物和含氮碱性化合物组成的复合催化剂制备聚碳酸酯。CN107573497A公开了酯交换过程使用咪唑类离子液体催化剂,其中R1,R2,R3可以相同也可以不相同,为H,CnH2n+1,CnH2n,CnH2n-1,CnH2nOH,CnH2nCOOH,CnH2nNH2,CnH2nCl,CnH2nBr,CnH2nI中的至少一种且n=1~20;X为四氟硼酸根,六氟磷酸根,硫酸氢根,硫酸根,对甲基苯磺酸根,磷酸二氢根,硝酸根,双三氟甲烷磺酰)亚胺根,三氟甲磺酸根,氢氧根,F-,Cl-,Br-,双氰胺根,硫氰酸根,甲酸根,醋酸根,脂肪酸根,软脂酸根,硬脂酸根,乙醇酸根,乳酸根,苯甲酸根,水杨酸根,柠檬酸根,酒石酸根,高氯酸根中至少一种。CN105949451B公开了以季胺类(1),(2)离子液体和季磷类(3)、(4)离子液体为催化剂制备聚碳酸酯,R1,R2,R3,R4为C1~C20的烷基,C4~C20的环烷基,和C4~C20的芳基中任一种;(1)和(3)中的阴离子X为二氰胺根阴离子、乳酸根阴离子、咪唑阴离子、1,2,4-三氮唑阴离子中的任一种;(2)和(4)中的阴离子X为二氰胺根阴离子、乳酸根阴离子、咪唑阴离子、1,2,4-三氮唑阴离子、苯甲酸根阴离子、磷酸二氢根、氢氧根阴离子、醋酸根阴离子、碳酸氢根阴离子中的任一种。CN107082878A公开了机碱类催化剂和碱性离子液体组成的复合催化剂制备聚碳酸酯,R1为烷基,R2为烷基、胺基、酰胺基或双酰胺基;X-为OH-,HCOO-,CH3COO-或H2PO4 -。CN107163240A公开了将固载化离子液体催化剂用于制备聚碳酸酯,固载化离子液体催化剂包括酸性离子液体和接枝有链转移剂的过渡金属化合物。
尽管报道的催化剂种类很多,但仍存在与原料、产物相溶性差(无机催化剂),催化剂稳定性差高温下易挥发、分解(有机催化剂),反应活性低、选择性不高等问题。因此,开发高活性、高选择性、高稳定性的催化剂体系还是很有必要的。
发明内容
本发明目的在于,提供一种高活性、高选择性、高稳定性的催化剂体系以用于制备聚碳酸酯过程。
发明人在制备聚碳酸酯过程中发现,无机碱性化合物在碳酸二酯与二羟基化合物的反应过程中相溶性不好,易发生Fries重排副反应,影响聚碳酸酯的品质。有机胺类催化剂在高温下易挥发、分解,反应活性不高。离子液体因其几乎不挥发、宽液程、结构可设计性等特点,在反应催化、材料制备、分离纯化等领域显示了良好的应用的前景。离子液体是由阴、阳离子两部分组成的离子型化合物,在结构和性质上与传统的溶剂分子存在明显区别,因此其碱性的调控策略和分子结构-碱性的构效关系,对于聚碳酸酯的合成具有重要意义。
发明人发现由季磷为阳离子、氨基酸根为阴离子组成的季磷氨基酸盐离子液体具有很强的碱性,其氢键碱性β达到1.0以上,其催化碳酸二酯与二羟基化合物反应的活性、选择性都非常高,产品聚碳酸酯的分子量高、品质好,用量也比普通的催化剂要少很多,体现了很好的应用价值。
本发明合成芳香族聚碳酸酯的反应通式为:
式中R1为甲基、乙基、丙基、丁基、苯基中的任意一种;X’为H、F、Cl、Br中的任意一种;选自,,,,,,,,,,,,,中的任意一种。
本发明合成脂肪族聚碳酸酯的反应通式为:
式中R1为甲基、乙基、丙基、丁基、苯基中的任意一种;R’为亚烷基,亚环烷基中的任意一种,x1/y1=300/0~0/300(摩尔比)。
具体地说,碳酸二酯为碳酸二甲酯、碳酸二乙酯、碳酸二丙酯、碳酸二丁酯和碳酸二苯酯中的任意一种。二羟基化合物选自异山梨醇、脂肪族二羟基化合物和芳香族二羟基化合物中的至少一种。其中,脂肪族二羟基化合物选自1,4-丁二醇,1,5-戊二醇,1,6-己二醇,1,7-庚二醇,1,8-辛二醇,1,4-环己二醇中的一种;芳香族二羟基化合物选自双酚A(学名2,2-双(4-羟基苯基)丙烷),四溴双酚A,四氯双酚A,环己烷双酚A,4,4'-二羟基二苯醚,1,1-双(4-羟基苯基)苯基乙烷,1,1-双(4-羟基苯基)苯基甲烷,1,1-双(4-羟基苯基)二苯基甲烷,酚酞,4,4'-二羟基二苯亚砜,双酚S(4,4'-二羟基二苯砜),4,4'-二羟基二苯硫醚,N,N'-二羟基二苯基硫脲,4,4'-二羟基二苯基二甲基硅烷,四溴双酚S(3,5,3',5'-四溴-4,4’-二羟基基二苯砜)中的任意一种。
本发明涉及一种基于强碱性离子液体高效催化制备聚碳酸酯的方法,其特征在于,使用由季磷为阳离子、氨基酸根为阴离子构成的离子液体为催化剂,催化以二羟基化合物和碳酸二酯为原料的反应制备聚碳酸酯。所述的制备聚碳酸酯包括预聚和缩聚两个步骤,在预聚阶段反应温度为100~200℃、压力为20kPa~常压,反应时间0.5h~6h;在缩聚阶段,反应温度为220~280℃、压力为20Pa~300Pa,反应时间0.1h~5h。
本发明碳酸二酯与二羟基化合物的摩尔比为1.0~5.0。所述的离子液体催化剂用量为二羟基化合物质量的1×10-6~2%。
本发明所述的离子液体结构式如下:
其中R1,R2,R3,R4为C1~C20的烷基,C4~C20的环烷基和C4~C20的芳基中的任一种;R1,R2,R3,R4的结构可以相同,也可以不同;X-为氨基酸根阴离子。
本发明所用的季磷氨基酸盐离子液体合成范例如下:
(1)合成四丁基膦丙氨酸盐
采用四丁基氢氧化磷(商品,40%水溶液)与丙氨酸发生酸碱中和反应,室温下搅拌24小时生成含目标离子液体的水溶液,然后将此水溶液在60℃下减压旋蒸除水分,最后离子液体至于55 ℃条件下高真空度干燥48小时。所有的离子液体在使用前均经过干燥,并用卡尔费休滴定仪进行检测其水含量(质量比),均在0.7%之下,离子液体产率95%以上。
(2)合成三己基十四烷基膦甘氨酸盐
将三己基十四烷基溴化磷(以下简称[P66614]Br)配成乙醇溶液,倒入已经用乙醇冲洗过的Dowex Monosphere 550A UPW(OH)型强碱阴离子交换树脂,用乙醇冲洗并以0.8 mL/min流速过柱,收集可得三己基十四烷基氢氧化磷(简称[P66614][OH])乙醇溶液,经过AgNO3+HCl溶液检验无沉淀。用0.1mol/L的HCl溶液标定[P66614][OH]溶液浓度,即得[P66614][OH]乙醇溶液。
选用甘氨酸与等摩尔量的[P66614][OH]乙醇溶液在圆底烧瓶中于45℃温度下搅拌反应24小时。反应完后,反应混合液在50℃下经过减压旋蒸除去乙醇和水后再用高压真空泵除去残余溶剂48 h,即得离子液体三己基十四烷基膦甘氨酸盐。离子液体使用前用高真空泵除水,水含量由卡尔费休滴定仪进行检测,其水含量(质量比)均在0.5%以下。
具体实施方式
以下结合实施例对本发明作进一步阐述,其目的仅在于更好理解本发明的内容而非限制本发明的保护范围。在不脱离前后所述宗旨的范围下,变化实施都包含于本发明的技术范围内。
实施例1
168.525g碳酸二苯酯(DPC)和171g双酚A(BPA)(DPC/BPA=1.05:1,摩尔比)加入反应釜中,在氮气保护下升温熔融至130℃,加入四丁基膦丙氨酸盐离子液体0.0114g(双酚A质量的6.7×10-5 %),抽真空,将釜内压强调至2500Pa,继续升温至165℃,反应35min后,压强降到130Pa,升温至260℃,停留10min即停止反应。用氮气压出产物,得到双酚A型聚碳酸酯,数均分子量为2.8×104 g/mol。
实施例2
同实例1,加入三己基十四烷基膦甘氨酸盐离子液体0.0114g(双酚A质量的6.7×10-5 %)。制备得到的双酚A型聚碳酸酯的数均分子量为3.2×104 g/mol。
实施例3
116.7g异山梨醇(IS)和171.05g碳酸二苯酯(DPC)(IS/DPC=1.0:1,摩尔比)加入反应釜中,在氮气保护下升温至100℃熔融,加入四丁基膦丙氨酸盐离子液体0.00782g(异山梨醇质量的6.7×10-5 %),抽真空,将釜内压强调至30kPa,继续升温至165℃,反应2h后,压强降到200Pa,升温至245℃,停留1h即停止反应。用氮气压出产物,得到异山梨醇型聚碳酸酯,数均分子量为2.3×104 g/mol。
实施例4
同实例3,加入三己基十四烷基膦甘氨酸盐离子液体0.00782g(异山梨醇质量的6.7×10-5 %)。制备得到的异山梨醇型聚碳酸酯的数均分子量为2.6×104 g/mol。
实施例5
58.35g(0.3995mol)异山梨醇(IS)、57.53g(0.3995mol)1,4-环己烷二甲醇和171.05g碳酸二苯酯(DPC)加入反应釜中,在氮气保护下升温至100℃熔融,加入四丁基膦丙氨酸盐离子液体0.0388g(异山梨醇+1,4-环己烷二甲醇质量的3.35×10-4%),抽真空,将釜内压强调至30kPa,继续升温至165℃,反应2h后,压强降到200Pa,升温至245℃,停留1h即停止反应。用氮气压出产物,得到共聚型聚碳酸酯,数均分子量为3.3×104 g/mol。
实施例6
同实例5,加入三己基十四烷基膦甘氨酸盐离子液体0.0388g(异山梨醇质量的3.35×10-4 %)。制备得到的共聚型聚碳酸酯的数均分子量为4.6×104 g/mol。
实施例7
116.7g(0.799mol)异山梨醇(IS)、143.82g(1.598mol)碳酸二甲酯(DMC)加入带有精馏塔的反应釜中,加入四丁基膦甘氨酸盐离子液体0.117g(异山梨醇质量的0.1%)。酯交换反应:在氮气保护下,将反应物和催化剂搅拌并升温至98℃,反应4h,逐步升高温度至180℃,并在该温度反应1h以除去副产物甲醇和未反应掉的DMC。在整个酯交换过程中,精馏塔塔顶温度保持在64~66℃范围,防止DMC过量蒸出。然后,升温降压,进行缩聚反应,釜内压力50Pa,温度220~260℃,反应4h后停止反应。用氮气压出产物,得到异山梨醇型聚碳酸酯PIC,数均分子量为3.2×104 g/mol。
实施例8
59g(0.2mol)异山梨醇(IS)、53.92g(0.5992mol)1,4-丁二醇、143.82g(1.598mol)碳酸二甲酯(DMC)加入带有精馏塔的反应釜中,加入四丁基膦甘氨酸盐离子液体0.083g(异山梨醇和1,4-丁二醇质量之和的0.1%)。其它同实例7。反应后用氮气压出产物,得到聚(异山梨醇-丁二醇)碳酸酯PBIC25(注:下标25代表异山梨醇在二羟基化合物中的摩尔百分含量),数均分子量为4.92×104 g/mol。
实施例9
58.4g(0.4mol)异山梨醇(IS)、36.0g(0.4mol)1,4-丁二醇、143.82g(1.598mol)碳酸二甲酯(DMC)加入带有精馏塔的反应釜中,加入四丁基膦甘氨酸盐离子液体0.0944g(异山梨醇和1,4-丁二醇质量之和的0.1%)。其它同实例7。反应后用氮气压出产物,得到聚(异山梨醇-丁二醇)碳酸酯PBIC50(注:下标50代表异山梨醇在二羟基化合物中的摩尔百分含量),数均分子量为3.64×104 g/mol。
实施例10
168.525g碳酸二苯酯(DPC)和408g(0.75mol)四溴双酚A(TBBPA)(DPC/TBBPA=1.05:1,摩尔比)加入反应釜中,在氮气保护下升温熔融至150℃,加入四丁基膦缬氨酸盐离子液体0.010408g(四溴双酚A质量的1×10-4 %),抽真空,将釜内压强调至2500Pa,继续升温至185℃,反应50min后,压强降到50Pa,升温至270℃,停留60min即停止反应。用氮气压出产物,得到四溴双酚A型聚碳酸酯TBPC,数均分子量为11.4×104 g/mol。
Claims (10)
1.一种基于强碱性离子液体高效催化制备聚碳酸酯的方法,其特征在于,使用由季磷为阳离子、氨基酸根为阴离子构成的离子液体为催化剂,催化以二羟基化合物和碳酸二酯为原料的反应制备聚碳酸酯;所述的离子液体结构式如下:
其中R1,R2,R3,R4为C1~C20的烷基,C4~C20的环烷基和C4~C20的芳基中的任一种;R1,R2,R3,R4的结构可以相同,也可以不同;X-为氨基酸根阴离子。
2.如权利要求1所述的方法,其特征在于,所述的聚碳酸酯为芳香族聚碳酸酯或者脂肪族聚碳酸酯,具有如下结构式:
,
(1) (2)
其中式(1)中X’为H、F、Cl、Br中的任意一种;选自,,,,,,,,,,,,,中的任意一种;式(2)中R’为亚烷基,亚环烷基中的任意一种,x1/y1=300/0~0/300(摩尔比)。
3.如权利要求1所述的方法,其特征在于,所述的氨基酸为甘氨酸Gly、丙氨酸Ala、缬氨酸Val、亮氨酸Leu、异亮氨酸Ile、苯丙氨酸Phe、色氨酸Trp、,酪氨酸Tyr、天冬氨酸Asp、天冬酰胺Asn、谷氨酸Glu、赖氨酸Lys、谷氨酰胺Gln、甲硫氨酸Met、丝氨酸Ser、苏氨酸Thr、半胱氨酸Cys、脯氨酸Pro、组氨酸His和精氨酸Arg中的任意一种。
4.如权利要求1所述的方法,其特征在于,所述的二羟基化合物选自异山梨醇、脂肪族二羟基化合物和芳香族二羟基化合物中的至少一种。
5.如权利要求1、4所述的方法,其特征在于,所述的脂肪族二羟基化合物选自1,4-丁二醇,1,5-戊二醇,1,6-己二醇,1,7-庚二醇,1,8-辛二醇,1,4-环己烷二甲醇中的一种。
6.如权利要求1、4所述的方法,其特征在于,所述的芳香族二羟基化合物选自双酚A(学名2,2-双(4-羟基苯基)丙烷),四溴双酚A,四氯双酚A,环己烷双酚A,4,4'-二羟基二苯醚,1,1-双(4-羟基苯基)苯基乙烷,1,1-双(4-羟基苯基)苯基甲烷,1,1-双(4-羟基苯基)二苯基甲烷,酚酞,4,4'-二羟基二苯亚砜,双酚S(4,4'-二羟基二苯砜),4,4'-二羟基二苯硫醚,N,N'-二羟基二苯基硫脲,4,4'-二羟基二苯基二甲基硅烷,四溴双酚S(3,5,3',5'-四溴-4,4’-二羟基基二苯砜)中的任意一种。
7.如权利要求1所述的方法,其特征在于,所述的碳酸二酯为碳酸二甲酯、碳酸二乙酯、碳酸二丙酯、碳酸二丁酯和碳酸二苯酯中的任意一种。
8.如权利要求1所述的方法,其特征在于,所述的原料碳酸二酯与二羟基化合物的摩尔比为1.0~5.0。
9.如权利要求1所述的方法,其特征在于,所述的离子液体催化剂用量为二羟基化合物质量的1×10-6~2%。
10.如权利要求1所述的方法,其特征在于,所述的制备聚碳酸酯包括预聚和缩聚两个步骤,在预聚阶段反应温度为100~200℃、压力为20kPa~常压,反应时间0.5h~6h;在缩聚阶段,反应温度为220~280℃、压力为20Pa~300Pa,反应时间0.1h~5h。
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