CN110144031B - Method for grafting and modifying lignin by photoinduction organic catalysis - Google Patents
Method for grafting and modifying lignin by photoinduction organic catalysis Download PDFInfo
- Publication number
- CN110144031B CN110144031B CN201910414047.5A CN201910414047A CN110144031B CN 110144031 B CN110144031 B CN 110144031B CN 201910414047 A CN201910414047 A CN 201910414047A CN 110144031 B CN110144031 B CN 110144031B
- Authority
- CN
- China
- Prior art keywords
- lignin
- phenothiazine
- naphthyl
- phenyl
- dihydrophenazine
- 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.)
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- 229920005610 lignin Polymers 0.000 title claims abstract description 91
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000006555 catalytic reaction Methods 0.000 title claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 32
- 229920000642 polymer Polymers 0.000 claims abstract description 31
- 239000000178 monomer Substances 0.000 claims abstract description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 75
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 58
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 29
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 27
- YOCIJWAHRAJQFT-UHFFFAOYSA-N 2-bromo-2-methylpropanoyl bromide Chemical group CC(C)(Br)C(Br)=O YOCIJWAHRAJQFT-UHFFFAOYSA-N 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 19
- -1 1-naphthyl-10H-phenothiazine Chemical compound 0.000 claims description 17
- 229950000688 phenothiazine Drugs 0.000 claims description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 150000002825 nitriles Chemical class 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 13
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 12
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 12
- WSEFYHOJDVVORU-UHFFFAOYSA-N 10-phenylphenothiazine Chemical group C12=CC=CC=C2SC2=CC=CC=C2N1C1=CC=CC=C1 WSEFYHOJDVVORU-UHFFFAOYSA-N 0.000 claims description 11
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 11
- 239000004305 biphenyl Substances 0.000 claims description 11
- 239000003999 initiator Substances 0.000 claims description 11
- 230000003197 catalytic effect Effects 0.000 claims description 10
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 7
- 239000005977 Ethylene Substances 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- 125000005257 alkyl acyl group Chemical group 0.000 claims description 6
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 6
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- JQSNKCDXBDOVMU-UHFFFAOYSA-N 1-naphthalen-1-yl-5,10-dihydrophenazine Chemical compound C1=CC=CC2=C(C=CC=C12)C1=CC=CC=2NC3=CC=CC=C3NC1=2 JQSNKCDXBDOVMU-UHFFFAOYSA-N 0.000 claims description 5
- RLAXVXKHKURYFZ-UHFFFAOYSA-N 1-naphthalen-2-yl-10H-phenoxazine Chemical compound C1=C(C=CC2=CC=CC=C12)C1=CC=CC=2OC3=CC=CC=C3NC12 RLAXVXKHKURYFZ-UHFFFAOYSA-N 0.000 claims description 5
- QXBUYALKJGBACG-UHFFFAOYSA-N 10-methylphenothiazine Chemical compound C1=CC=C2N(C)C3=CC=CC=C3SC2=C1 QXBUYALKJGBACG-UHFFFAOYSA-N 0.000 claims description 5
- NZOYBWLCZWTECI-UHFFFAOYSA-N 4-chloro-10h-phenothiazine Chemical compound N1C2=CC=CC=C2SC2=C1C=CC=C2Cl NZOYBWLCZWTECI-UHFFFAOYSA-N 0.000 claims description 5
- RCBSZGSHSLQLBI-UHFFFAOYSA-N 5,10-diphenylphenazine Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N(C=2C=CC=CC=2)C2=CC=CC=C21 RCBSZGSHSLQLBI-UHFFFAOYSA-N 0.000 claims description 5
- PDEMFFCYEHCCDT-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CC=CC=2NC3=CC=CC=C3NC12 Chemical compound COC1=CC=C(C=C1)C1=CC=CC=2NC3=CC=CC=C3NC12 PDEMFFCYEHCCDT-UHFFFAOYSA-N 0.000 claims description 5
- 229960001701 chloroform Drugs 0.000 claims description 5
- 230000004048 modification Effects 0.000 claims description 5
- 238000012986 modification Methods 0.000 claims description 5
- UOHKISLIYZMUGE-UHFFFAOYSA-N 1-naphthalen-1-yl-10H-phenoxazine Chemical compound C1(=CC=CC2=CC=CC=C12)C1=CC=CC=2OC3=CC=CC=C3NC1=2 UOHKISLIYZMUGE-UHFFFAOYSA-N 0.000 claims description 4
- DMTAVUBDKPDIQZ-UHFFFAOYSA-N 1-phenyl-12H-benzo[b]phenothiazine Chemical compound C1(=CC=CC=C1)C1=CC=CC=2SC=3C=C4C(=CC=3NC1=2)C=CC=C4 DMTAVUBDKPDIQZ-UHFFFAOYSA-N 0.000 claims description 4
- NSKCIYCOJUZRKT-UHFFFAOYSA-N 10-[4-(trifluoromethyl)phenyl]phenothiazine Chemical compound C1=CC(C(F)(F)F)=CC=C1N1C2=CC=CC=C2SC2=CC=CC=C21 NSKCIYCOJUZRKT-UHFFFAOYSA-N 0.000 claims description 4
- PYNYHMRMZOGVML-UHFFFAOYSA-N 2-bromopropanenitrile Chemical compound CC(Br)C#N PYNYHMRMZOGVML-UHFFFAOYSA-N 0.000 claims description 4
- CVKBLFQXQAXSAQ-UHFFFAOYSA-N C1=C(C=CC2=CC=CC=C12)C1=CC=CC=2SC3=CC=CC=C3NC1=2 Chemical compound C1=C(C=CC2=CC=CC=C12)C1=CC=CC=2SC3=CC=CC=C3NC1=2 CVKBLFQXQAXSAQ-UHFFFAOYSA-N 0.000 claims description 4
- 229920001732 Lignosulfonate Polymers 0.000 claims description 4
- OQROAIRCEOBYJA-UHFFFAOYSA-N bromodiphenylmethane Chemical compound C=1C=CC=CC=1C(Br)C1=CC=CC=C1 OQROAIRCEOBYJA-UHFFFAOYSA-N 0.000 claims description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 4
- NVVCZYAGESORQR-UHFFFAOYSA-N 1-[4-(trifluoromethyl)phenyl]-10H-phenoxazine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC2=C1NC1=CC=CC=C1O2 NVVCZYAGESORQR-UHFFFAOYSA-N 0.000 claims description 3
- LAVLDGSVWFEKJG-UHFFFAOYSA-N 10-phenylphenoxazine Chemical compound C12=CC=CC=C2OC2=CC=CC=C2N1C1=CC=CC=C1 LAVLDGSVWFEKJG-UHFFFAOYSA-N 0.000 claims description 3
- UZDMSTZDTLPULS-UHFFFAOYSA-N 10-pyridin-2-ylphenothiazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1C1=CC=CC=N1 UZDMSTZDTLPULS-UHFFFAOYSA-N 0.000 claims description 3
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 3
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 3
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 3
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- BKORERVNQPDBNW-UHFFFAOYSA-N 10-[4-(trifluoromethyl)phenyl]phenoxazine Chemical compound FC(C1=CC=C(C=C1)N1C2=CC=CC=C2OC=2C=CC=CC1=2)(F)F BKORERVNQPDBNW-UHFFFAOYSA-N 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- JTPUMZTWMWIVPA-UHFFFAOYSA-O Isopropamide Chemical compound C=1C=CC=CC=1C(C(N)=O)(CC[N+](C)(C(C)C)C(C)C)C1=CC=CC=C1 JTPUMZTWMWIVPA-UHFFFAOYSA-O 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 229960001737 isopropamide Drugs 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 239000002184 metal Substances 0.000 abstract description 5
- 238000010559 graft polymerization reaction Methods 0.000 abstract 1
- 238000010526 radical polymerization reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 238000001291 vacuum drying Methods 0.000 description 24
- 238000003756 stirring Methods 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- 238000007865 diluting Methods 0.000 description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 230000001376 precipitating effect Effects 0.000 description 11
- 238000010791 quenching Methods 0.000 description 11
- 230000000171 quenching effect Effects 0.000 description 11
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 11
- 229920005611 kraft lignin Polymers 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- MXFYYFVVIIWKFE-UHFFFAOYSA-N dicyclohexyl-[2-[2,6-di(propan-2-yloxy)phenyl]phenyl]phosphane Chemical compound CC(C)OC1=CC=CC(OC(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 MXFYYFVVIIWKFE-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
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- 238000006116 polymerization reaction Methods 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- JGGSOWGJMBNDHS-UHFFFAOYSA-N 10-phenyl-5h-phenazine Chemical compound C12=CC=CC=C2NC2=CC=CC=C2N1C1=CC=CC=C1 JGGSOWGJMBNDHS-UHFFFAOYSA-N 0.000 description 3
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
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- 230000002194 synthesizing effect Effects 0.000 description 3
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 2
- IVURTNNWJAPOML-UHFFFAOYSA-N 5,10-dihydrophenazine Chemical compound C1=CC=C2NC3=CC=CC=C3NC2=C1 IVURTNNWJAPOML-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Effective date of registration: 20220309 Address after: 100000 22 Chaoyangmen North Street, Chaoyang District, Beijing. Patentee after: CHINA PETROLEUM & CHEMICAL Corp. Address before: 210000 Puzhu South Road, Pukou District, Nanjing, Jiangsu 30 Patentee before: Nanjing Tech University |