JP2010536799A - エポキシドのイソ選択的重合 - Google Patents
エポキシドのイソ選択的重合 Download PDFInfo
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- JP2010536799A JP2010536799A JP2010521231A JP2010521231A JP2010536799A JP 2010536799 A JP2010536799 A JP 2010536799A JP 2010521231 A JP2010521231 A JP 2010521231A JP 2010521231 A JP2010521231 A JP 2010521231A JP 2010536799 A JP2010536799 A JP 2010536799A
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- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 132
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- 229920000642 polymer Polymers 0.000 claims abstract description 295
- 238000000034 method Methods 0.000 claims abstract description 116
- 239000003054 catalyst Substances 0.000 claims abstract description 84
- 239000000463 material Substances 0.000 claims abstract description 41
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- 239000012501 chromatography medium Substances 0.000 claims abstract description 4
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 345
- 229910052717 sulfur Chemical group 0.000 claims description 247
- 229910052757 nitrogen Inorganic materials 0.000 claims description 203
- 229910052760 oxygen Inorganic materials 0.000 claims description 169
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 168
- 239000001301 oxygen Chemical group 0.000 claims description 168
- 239000011593 sulfur Chemical group 0.000 claims description 165
- 125000005842 heteroatom Chemical group 0.000 claims description 163
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 158
- 125000001931 aliphatic group Chemical group 0.000 claims description 117
- 125000003118 aryl group Chemical group 0.000 claims description 105
- 125000000623 heterocyclic group Chemical group 0.000 claims description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 67
- 125000004429 atom Chemical group 0.000 claims description 58
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 56
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 53
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- 238000000638 solvent extraction Methods 0.000 claims 1
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- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 17
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- 150000002829 nitrogen Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000005545 phthalimidyl group Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- HAMAGKWXRRTWCJ-UHFFFAOYSA-N pyrido[2,3-b][1,4]oxazin-3-one Chemical compound C1=CN=C2OC(=O)C=NC2=C1 HAMAGKWXRRTWCJ-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical group CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
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- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
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- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
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- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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- C07F15/065—Cobalt compounds without a metal-carbon linkage
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/70—Chelates
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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
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- C08G65/10—Saturated oxiranes characterised by the catalysts used
- C08G65/12—Saturated oxiranes characterised by the catalysts used containing organo-metallic compounds or metal hydrides
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- 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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
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- C—CHEMISTRY; METALLURGY
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- C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/266—Metallic elements not covered by group C08G65/2648 - C08G65/2645, or compounds thereof
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/14—Other (co) polymerisation, e.g. of lactides or epoxides
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0202—Polynuclearity
- B01J2531/0205—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93552907P | 2007-08-17 | 2007-08-17 | |
| PCT/US2008/073530 WO2009026261A2 (en) | 2007-08-17 | 2008-08-18 | Isoselective polymerization of epoxides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010536799A true JP2010536799A (ja) | 2010-12-02 |
| JP2010536799A5 JP2010536799A5 (https=) | 2011-09-29 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2010521231A Pending JP2010536799A (ja) | 2007-08-17 | 2008-08-18 | エポキシドのイソ選択的重合 |
Country Status (4)
| Country | Link |
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| US (3) | US20100144969A1 (https=) |
| EP (1) | EP2195305A2 (https=) |
| JP (1) | JP2010536799A (https=) |
| WO (1) | WO2009026261A2 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015038052A (ja) * | 2013-08-19 | 2015-02-26 | 国立大学法人 千葉大学 | ビナフトール骨格を有するビスアミノイミン配位子及び触媒 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2195305A2 (en) | 2007-08-17 | 2010-06-16 | Cornell Research Foundation, Inc. | Isoselective polymerization of epoxides |
| JP5781939B2 (ja) | 2008-12-23 | 2015-09-24 | ノボマー， インコーポレイテッド | 調整可能なポリマー組成物 |
| BRPI1005290A2 (pt) | 2009-02-26 | 2016-03-22 | Dow Global Technologies Inc | composição |
| WO2012166889A2 (en) | 2011-05-31 | 2012-12-06 | Cornell University | Polyethers, methods of making same, and uses thereof |
| MY184782A (en) * | 2011-11-03 | 2021-04-21 | Malaysian Palm Oil Board | A method to produce copolymers of tetrahydrofuran and epoxidized natural oils |
| EP4097169A1 (en) * | 2020-01-31 | 2022-12-07 | Dow Global Technologies LLC | Alkylene oxide polymerization using aluminum compounds and phosphorus-nitrogen bases |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060293501A1 (en) * | 2005-06-21 | 2006-12-28 | Cornell Research Foundation, Inc. | Isotactic specific catalyst for direct production of highly isotactic poly (propylene oxide) or Highly isotactic poly (butylene Oxide) |
| JP2008208348A (ja) * | 2007-01-30 | 2008-09-11 | Sanyo Chem Ind Ltd | ウレタン樹脂組成物 |
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| JP4275795B2 (ja) * | 1999-03-30 | 2009-06-10 | 高砂香料工業株式会社 | ビニル基を有するホスフィン誘導体、それをモノマーとするポリマー及びそれらの遷移金属錯体 |
| WO2006099162A2 (en) * | 2005-03-14 | 2006-09-21 | Georgia Tech Research Corporation | Polymeric salen compounds and methods thereof |
| EP2195305A2 (en) | 2007-08-17 | 2010-06-16 | Cornell Research Foundation, Inc. | Isoselective polymerization of epoxides |
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2008
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2010
- 2010-02-16 US US12/706,077 patent/US20100144969A1/en not_active Abandoned
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2012
- 2012-09-21 US US13/624,187 patent/US8710283B2/en active Active
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2014
- 2014-03-21 US US14/222,471 patent/US20140206829A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060293501A1 (en) * | 2005-06-21 | 2006-12-28 | Cornell Research Foundation, Inc. | Isotactic specific catalyst for direct production of highly isotactic poly (propylene oxide) or Highly isotactic poly (butylene Oxide) |
| JP2008208348A (ja) * | 2007-01-30 | 2008-09-11 | Sanyo Chem Ind Ltd | ウレタン樹脂組成物 |
Non-Patent Citations (2)
| Title |
|---|
| JPN7013002572; Ｊｏｕｒｎａｌ ｏｆ Ｍｏｌｅｃｕｌａｒ Ｓｔｒｕｃｔｕｒｅ ８００, 2006, １-１７ * |
| JPN7013002573; Ｐｏｌｙｍｅｒ Ｊｏｕｒｎａｌ Ｖｏｌ．２５， Ｎｏ．７, 1993, ６８５-６９６ * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015038052A (ja) * | 2013-08-19 | 2015-02-26 | 国立大学法人 千葉大学 | ビナフトール骨格を有するビスアミノイミン配位子及び触媒 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20140206829A1 (en) | 2014-07-24 |
| US20100144969A1 (en) | 2010-06-10 |
| WO2009026261A2 (en) | 2009-02-26 |
| US20130079491A1 (en) | 2013-03-28 |
| US8710283B2 (en) | 2014-04-29 |
| WO2009026261A3 (en) | 2009-04-30 |
| EP2195305A2 (en) | 2010-06-16 |
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