CN101254474A - Catalyst for isocyanate trimerization, preparation and use method - Google Patents
Catalyst for isocyanate trimerization, preparation and use method Download PDFInfo
- Publication number
- CN101254474A CN101254474A CNA2008100199908A CN200810019990A CN101254474A CN 101254474 A CN101254474 A CN 101254474A CN A2008100199908 A CNA2008100199908 A CN A2008100199908A CN 200810019990 A CN200810019990 A CN 200810019990A CN 101254474 A CN101254474 A CN 101254474A
- Authority
- CN
- China
- Prior art keywords
- catalyst
- isocyanate trimerization
- isocyanate
- solvent
- ligand
- 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.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 44
- 239000012948 isocyanate Substances 0.000 title claims abstract description 37
- 238000005829 trimerization reaction Methods 0.000 title claims abstract description 30
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 13
- -1 isocyanate compounds Chemical class 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 229910052751 metal Inorganic materials 0.000 claims abstract description 9
- 239000002184 metal Substances 0.000 claims abstract description 9
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 8
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 7
- 150000002602 lanthanoids Chemical class 0.000 claims abstract description 7
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 34
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 12
- 239000003446 ligand Substances 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 9
- 229910006400 μ-Cl Inorganic materials 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 208000035126 Facies Diseases 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 description 12
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 125000002524 organometallic group Chemical group 0.000 description 5
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 5
- 150000002910 rare earth metals Chemical class 0.000 description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 3
- 239000002879 Lewis base Substances 0.000 description 2
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 2
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- PSXUKPCAIKETHF-UHFFFAOYSA-N 2-[4-[3-[4-(4,5-dihydro-1h-imidazol-2-yl)phenoxy]propoxy]phenyl]-4,5-dihydro-1h-imidazole Chemical compound C=1C=C(C=2NCCN=2)C=CC=1OCCCOC(C=C1)=CC=C1C1=NCCN1 PSXUKPCAIKETHF-UHFFFAOYSA-N 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 102100029579 Diphosphoinositol polyphosphate phosphohydrolase 1 Human genes 0.000 description 1
- 229910052691 Erbium Inorganic materials 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 230000000655 anti-hydrolysis Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 238000010550 living polymerization reaction Methods 0.000 description 1
- 101710153356 mRNA-decapping protein g5R Proteins 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Yield (%) | |
Embodiment 7 | 92 |
Embodiment 8 | 99 |
Embodiment 9 | 99 |
Embodiment 10 | 99 |
Embodiment 11 | 99 |
Yield (%) | |
Embodiment 13 | 99 |
Embodiment 14 | 99 |
Embodiment 15 | 10 |
Embodiment 16 | 11 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2008100199908A CN101254474B (en) | 2008-03-19 | 2008-03-19 | Catalyst for isocyanate trimerization, preparation and use method |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2008100199908A CN101254474B (en) | 2008-03-19 | 2008-03-19 | Catalyst for isocyanate trimerization, preparation and use method |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101254474A true CN101254474A (en) | 2008-09-03 |
CN101254474B CN101254474B (en) | 2010-06-02 |
Family
ID=39889780
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN2008100199908A Expired - Fee Related CN101254474B (en) | 2008-03-19 | 2008-03-19 | Catalyst for isocyanate trimerization, preparation and use method |
Country Status (1)
Country | Link |
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CN (1) | CN101254474B (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104163906A (en) * | 2014-03-07 | 2014-11-26 | 华东理工大学 | Catalyst for use in trimerization of isocyanate and cyclization reaction of isocyanate and epoxy and application thereof |
CN107913730A (en) * | 2017-11-30 | 2018-04-17 | 万华化学集团股份有限公司 | Imine quaternary ammonium salt catalyst, its preparation method and polyisocyantates composition |
CN109012748A (en) * | 2018-07-27 | 2018-12-18 | 安徽师范大学 | Pyridine substituted azole base rare-earth metal catalyst and its preparation method and application |
CN114262302A (en) * | 2022-01-04 | 2022-04-01 | 山东新和成维生素有限公司 | Method for synthesizing diisocyanate trimer, catalyst and preparation method thereof |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2803297B1 (en) * | 1999-12-29 | 2002-10-25 | Rhodia Chimie Sa | PROCESS FOR POLYCONDENSATION OF ISOCYANATES |
DE102005034052A1 (en) * | 2005-07-21 | 2007-01-25 | Goldschmidt Gmbh | trimerization |
-
2008
- 2008-03-19 CN CN2008100199908A patent/CN101254474B/en not_active Expired - Fee Related
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104163906A (en) * | 2014-03-07 | 2014-11-26 | 华东理工大学 | Catalyst for use in trimerization of isocyanate and cyclization reaction of isocyanate and epoxy and application thereof |
CN107913730A (en) * | 2017-11-30 | 2018-04-17 | 万华化学集团股份有限公司 | Imine quaternary ammonium salt catalyst, its preparation method and polyisocyantates composition |
CN109012748A (en) * | 2018-07-27 | 2018-12-18 | 安徽师范大学 | Pyridine substituted azole base rare-earth metal catalyst and its preparation method and application |
CN109012748B (en) * | 2018-07-27 | 2021-03-16 | 安徽师范大学 | Pyridine substituted pyrrole based rare earth metal catalyst and preparation method and application thereof |
CN114262302A (en) * | 2022-01-04 | 2022-04-01 | 山东新和成维生素有限公司 | Method for synthesizing diisocyanate trimer, catalyst and preparation method thereof |
CN114262302B (en) * | 2022-01-04 | 2023-09-29 | 山东新和成维生素有限公司 | Method for synthesizing diisocyanate trimer, catalyst and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
CN101254474B (en) | 2010-06-02 |
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Legal Events
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C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract |
Assignee: Youbang Chemical Co., Ltd., Lishui, Zhejiang Prov. Assignor: Anhui Normal University Contract record no.: 2010330001902 Denomination of invention: Catalyst for isocyanate trimerization, preparation and use method Granted publication date: 20100602 License type: Exclusive License Open date: 20080903 Record date: 20100920 |
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EM01 | Change of recordation of patent licensing contract |
Change date: 20130715 Contract record no.: 2010330001902 Assignee after: UPCHEM (CHINA) CO., LTD. Assignee before: Youbang Chemical Co., Ltd., Lishui, Zhejiang Prov. |
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LICC | Enforcement, change and cancellation of record of contracts on the licence for exploitation of a patent or utility model | ||
CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20100602 Termination date: 20190319 |