JP2012501360A5 - - Google Patents
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- Publication number
- JP2012501360A5 JP2012501360A5 JP2011524173A JP2011524173A JP2012501360A5 JP 2012501360 A5 JP2012501360 A5 JP 2012501360A5 JP 2011524173 A JP2011524173 A JP 2011524173A JP 2011524173 A JP2011524173 A JP 2011524173A JP 2012501360 A5 JP2012501360 A5 JP 2012501360A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon dioxide
- carbon atoms
- polylactic acid
- dioxide compound
- 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
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- -1 carbene carbon dioxide compound Chemical class 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims description 9
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 5
- JJTUDXZGHPGLLC-ZXZARUISSA-N (3r,6s)-3,6-dimethyl-1,4-dioxane-2,5-dione Chemical compound C[C@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-ZXZARUISSA-N 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 3
- 235000011054 acetic acid Nutrition 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000012662 bulk polymerization Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Natural products O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 35
- 239000001569 carbon dioxide Substances 0.000 claims 34
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 34
- 125000004432 carbon atom Chemical group C* 0.000 claims 31
- 229920000747 poly(lactic acid) Polymers 0.000 claims 28
- 239000004626 polylactic acid Substances 0.000 claims 28
- 238000004519 manufacturing process Methods 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 22
- 125000005843 halogen group Chemical group 0.000 claims 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 125000001424 substituent group Chemical group 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical group C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 239000011261 inert gas Substances 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 229910052786 argon Inorganic materials 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 2
- 229910001873 dinitrogen Inorganic materials 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 230000035484 reaction time Effects 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001722 carbon compounds Chemical class 0.000 claims 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 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 0 CC1C(*)C(C)=C(C(O)=O)N(*)C(*)C1C Chemical compound CC1C(*)C(C)=C(C(O)=O)N(*)C(*)C1C 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810146617.9 | 2008-09-01 | ||
| CN2008101466179A CN101665565B (zh) | 2008-09-01 | 2008-09-01 | 一种用卡宾衍生物催化制备聚乳酸的方法 |
| PCT/CN2009/073677 WO2010022685A1 (zh) | 2008-09-01 | 2009-09-02 | 用卡宾衍生物催化制备聚乳酸的方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012501360A JP2012501360A (ja) | 2012-01-19 |
| JP2012501360A5 true JP2012501360A5 (enExample) | 2014-02-13 |
| JP5481483B2 JP5481483B2 (ja) | 2014-04-23 |
Family
ID=41720855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011524173A Expired - Fee Related JP5481483B2 (ja) | 2008-09-01 | 2009-09-02 | カルベン誘導体を用いたポリ乳酸の製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9029497B2 (enExample) |
| EP (1) | EP2392606B1 (enExample) |
| JP (1) | JP5481483B2 (enExample) |
| CN (1) | CN101665565B (enExample) |
| WO (1) | WO2010022685A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20140029373A (ko) * | 2010-12-10 | 2014-03-10 | 클라리언트 파이넌스 (비브이아이)리미티드 | 락톤 개환 중합에 사용하기 위한 ｎ-헤테로사이클릭 카르벤 기반 지르코늄 착물 |
| CN102167802A (zh) * | 2011-01-13 | 2011-08-31 | 南京工业大学 | 一种用N-杂环卡宾催化制备聚α-羟基酸的方法 |
| EP2644636A1 (de) * | 2012-03-26 | 2013-10-02 | Basf Se | Verfahren zur herstellung von polyetherpolyolen |
| CN103160380A (zh) * | 2013-03-28 | 2013-06-19 | 南京工业大学 | 一种1,2,3-三唑卡宾二氧化碳加合物催化制备生物柴油的方法 |
| CN104892916B (zh) * | 2015-06-11 | 2017-01-11 | 南京大学 | 有机胍—无毒醇催化丙交酯活性开环聚合受控合成聚乳酸的工艺 |
| CN105273175B (zh) * | 2015-10-21 | 2017-06-13 | 南京工业大学 | 有机小分子催化剂调控的聚丙交酯制备方法 |
| CN105327713B (zh) * | 2015-11-16 | 2017-06-16 | 湖北大学 | 一种金刚烷支撑NHC‑Pd催化剂及其制备方法和用途 |
| CN105218793A (zh) * | 2015-11-17 | 2016-01-06 | 南京工业大学 | 一种用卡宾衍生物催化制备聚酯多元醇的方法 |
| US10570252B2 (en) | 2017-03-08 | 2020-02-25 | International Business Machines Corporation | Flame retardant lactide monomors for polylactide synthesis |
| US10072121B1 (en) | 2017-03-08 | 2018-09-11 | International Business Machines Corporation | Bottlebrush polymers derived from poly(methylidenelactide) |
| US10202489B2 (en) | 2017-03-08 | 2019-02-12 | International Business Machines Corporation | Lactide copolymers and ring-opened lactide copolymers |
| US10035877B1 (en) | 2017-03-08 | 2018-07-31 | International Business Machines Corporation | Matrix-bondable lactide monomors for polylactide synthesis |
| CN106947067B (zh) * | 2017-04-28 | 2022-01-04 | 南京工业大学 | 一种聚酯的制备方法 |
| JP7090487B2 (ja) * | 2018-06-25 | 2022-06-24 | 株式会社クラレ | ポリエステル重合用触媒、並びにポリエステル樹脂及びその製造方法 |
| CN111548480B (zh) * | 2019-12-08 | 2022-04-22 | 南京工业大学 | 一种含呋喃环的聚合物的合成方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3736646A (en) | 1971-10-18 | 1973-06-05 | American Cyanamid Co | Method of attaching surgical needles to multifilament polyglycolic acid absorbable sutures |
| US4057537A (en) | 1975-01-28 | 1977-11-08 | Gulf Oil Corporation | Copolymers of L-(-)-lactide and epsilon caprolactone |
| US4045418A (en) | 1975-01-28 | 1977-08-30 | Gulf Oil Corporation | Copolymers of D,L-lactide and epsilon caprolactone |
| US5235031A (en) | 1992-03-13 | 1993-08-10 | E. I. Du Pont De Nemours And Company | Polymerization of lactide |
| US5357034A (en) | 1992-09-08 | 1994-10-18 | Camelot Technologies Inc. | Lactide polymerization |
| JP2621813B2 (ja) * | 1994-01-21 | 1997-06-18 | 株式会社島津製作所 | ポリ乳酸の製造法 |
| EP0664309B1 (en) * | 1994-01-21 | 1999-06-02 | Shimadzu Corporation | Method for producing polylactic acid |
| US5574129A (en) * | 1994-05-10 | 1996-11-12 | The Japan Steel Works, Ltd. | Process for producing lactic acid polymers and a process for the direct production of shaped articles from lactic acid polymers |
| JP2847617B2 (ja) | 1994-05-10 | 1999-01-20 | 株式会社日本製鋼所 | 高分子量ポリ乳酸及びその成形体の製造方法 |
| JP2850101B2 (ja) | 1994-09-09 | 1999-01-27 | 株式会社日本製鋼所 | ポリ乳酸の製造方法 |
| US5696219A (en) * | 1997-01-21 | 1997-12-09 | Dow Corning Corporation | Silyl ester initiators for cyclosiloxane ring opening polymerization |
| DE10020898B4 (de) * | 2000-04-20 | 2004-02-05 | Inventa-Fischer Gmbh | Verfahren zur Herstellung von Polymilchsäure und Vorrichtung hierzu |
| WO2002060891A1 (fr) * | 2001-01-31 | 2002-08-08 | Toyota Jidosha Kabushiki Kaisha | Procédé de production de lactide et procédé de production d'acide polylactique à partir d'acide lactique fermenté |
| JP4048764B2 (ja) | 2001-01-31 | 2008-02-20 | トヨタ自動車株式会社 | 発酵乳酸を原料とするラクチドの製造方法及びポリ乳酸の製造方法 |
| CN1164639C (zh) | 2001-06-29 | 2004-09-01 | 武汉大学 | 一种制备聚乳酸的方法 |
| CN1212343C (zh) | 2003-11-27 | 2005-07-27 | 中国科学院长春应用化学研究所 | 环酯开环聚合催化剂及制备方法 |
| FR2864543B1 (fr) * | 2003-12-30 | 2006-03-03 | Rhodia Chimie Sa | Procede de preparation de polyorganosiloxanes (pos) par polymerisation par ouverture de cycle(s) et/ou redistribution de pos, en presence de carbene(s) et compositions de pos mises en oeuvre dans ce procede |
| WO2006053071A2 (en) * | 2004-11-09 | 2006-05-18 | E.I. Dupont De Nemours And Company | Ring opening polymerization of cyclic amides using n-heterocyclic carbene catalysts |
| US7622543B2 (en) * | 2004-11-09 | 2009-11-24 | E.I. Du Pont De Nemours And Company | Polymerization of macrocyclic polyester oligomers using N-heterocyclic carbene catalysts |
| JP4368289B2 (ja) * | 2004-11-15 | 2009-11-18 | 独立行政法人科学技術振興機構 | α−アルキリデン−１，３−ジオキソラン−２−オン類の製造方法 |
| CN1277859C (zh) * | 2005-04-15 | 2006-10-04 | 浙江大学 | 一种脂肪族聚酯的制备方法 |
| CN1706878A (zh) * | 2005-04-15 | 2005-12-14 | 浙江大学 | 无金属n－杂环卡宾催化剂及其制备方法 |
| CN100393771C (zh) | 2006-03-03 | 2008-06-11 | 中国科学院长春应用化学研究所 | 用于丙交酯开环聚合的席夫碱铝催化剂及制备方法和用法 |
| CN100406491C (zh) | 2006-03-03 | 2008-07-30 | 中国科学院长春应用化学研究所 | 一种烯醇式丙交酯开环聚合催化剂及制备方法和其用法 |
| DE102006038934A1 (de) * | 2006-08-18 | 2008-02-21 | Evonik Degussa Gmbh | Herstellung von α-Hydroxyketonen über Carbenkatalysierte Umpolungsreaktion von Aldehyden |
| FR2910004A1 (fr) * | 2006-12-14 | 2008-06-20 | Rhodia Recherches & Tech | Procede d'oligomerisation et/ou polymerisation du composes insatures |
| CN101230076A (zh) * | 2007-09-30 | 2008-07-30 | 赢创德固赛有限责任公司 | 含有n杂环卡宾配体的钌的同核双金属和异核双金属亚烷基配合物及其用途 |
| CN101205242A (zh) * | 2007-09-30 | 2008-06-25 | 埃沃尼克德古萨有限责任公司 | 含有n-杂环卡宾配体的钌的亚烷基络合物及其在烯烃复分解反应中作为高活性高选择性催化剂的用途 |
| CN101665567B (zh) * | 2008-09-01 | 2011-11-23 | 南京工业大学 | 卡宾衍生物催化的环状化合物可调控开环聚合方法 |
-
2008
- 2008-09-01 CN CN2008101466179A patent/CN101665565B/zh active Active
-
2009
- 2009-09-02 JP JP2011524173A patent/JP5481483B2/ja not_active Expired - Fee Related
- 2009-09-02 EP EP09809270.3A patent/EP2392606B1/en not_active Not-in-force
- 2009-09-02 WO PCT/CN2009/073677 patent/WO2010022685A1/zh not_active Ceased
-
2011
- 2011-02-24 US US13/034,119 patent/US9029497B2/en active Active
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