TW201500352A - 環狀碳酸酯合成用觸媒之製造方法 - Google Patents
環狀碳酸酯合成用觸媒之製造方法 Download PDFInfo
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- TW201500352A TW201500352A TW103114736A TW103114736A TW201500352A TW 201500352 A TW201500352 A TW 201500352A TW 103114736 A TW103114736 A TW 103114736A TW 103114736 A TW103114736 A TW 103114736A TW 201500352 A TW201500352 A TW 201500352A
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- Prior art keywords
- catalyst
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- cyclic carbonate
- reacting
- reaction
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- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
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- IRDQEMSRVZZPED-UHFFFAOYSA-N bis(2-methylpropyl)-phenylphosphane Chemical compound CC(C)CP(CC(C)C)C1=CC=CC=C1 IRDQEMSRVZZPED-UHFFFAOYSA-N 0.000 description 1
- JXGRYJKRTZIVRI-UHFFFAOYSA-N bis(2-methylpropyl)-propylphosphane Chemical compound C(C(C)C)P(CCC)CC(C)C JXGRYJKRTZIVRI-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- ZRTSLXKVIFNEQO-UHFFFAOYSA-N bromo(tributyl)phosphanium Chemical group CCCC[P+](Br)(CCCC)CCCC ZRTSLXKVIFNEQO-UHFFFAOYSA-N 0.000 description 1
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- ROKKESZHFRSLMO-UHFFFAOYSA-N butyl(dioctyl)phosphane Chemical compound CCCCCCCCP(CCCC)CCCCCCCC ROKKESZHFRSLMO-UHFFFAOYSA-N 0.000 description 1
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- FCYPYQPCOBMRAJ-UHFFFAOYSA-N butyl(dipropyl)phosphane Chemical compound CCCCP(CCC)CCC FCYPYQPCOBMRAJ-UHFFFAOYSA-N 0.000 description 1
- ASONLOCMPLDHNU-UHFFFAOYSA-N butyl-bis(2,3-dimethylphenyl)phosphane Chemical compound C=1C=CC(C)=C(C)C=1P(CCCC)C1=CC=CC(C)=C1C ASONLOCMPLDHNU-UHFFFAOYSA-N 0.000 description 1
- MCAWSCRONOWOQI-UHFFFAOYSA-N butyl-bis(2,6-dimethoxyphenyl)phosphane Chemical compound COC=1C=CC=C(OC)C=1P(CCCC)C1=C(OC)C=CC=C1OC MCAWSCRONOWOQI-UHFFFAOYSA-N 0.000 description 1
- XYQDBLYGPQBFDE-UHFFFAOYSA-N butyl-di(propan-2-yl)phosphane Chemical compound CCCCP(C(C)C)C(C)C XYQDBLYGPQBFDE-UHFFFAOYSA-N 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- NTIFKWPEJRPCOU-UHFFFAOYSA-N carbonic acid;hex-1-ene Chemical compound OC(O)=O.CCCCC=C NTIFKWPEJRPCOU-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- CVASMYWHWRNWOX-UHFFFAOYSA-N chloro methyl carbonate Chemical compound COC(=O)OCl CVASMYWHWRNWOX-UHFFFAOYSA-N 0.000 description 1
- 239000000490 cosmetic additive Substances 0.000 description 1
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- 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
- JFGIMJLRFIIMIC-UHFFFAOYSA-N cyclohexyl(diethyl)phosphane Chemical compound CCP(CC)C1CCCCC1 JFGIMJLRFIIMIC-UHFFFAOYSA-N 0.000 description 1
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- RBZGLYZCUOKDSP-UHFFFAOYSA-N cyclohexyl-di(propan-2-yl)phosphane Chemical compound CC(C)P(C(C)C)C1CCCCC1 RBZGLYZCUOKDSP-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical class CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
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- AFFFKBLBDKCYCM-UHFFFAOYSA-N dibutyl(propan-2-yl)phosphane Chemical compound CCCCP(C(C)C)CCCC AFFFKBLBDKCYCM-UHFFFAOYSA-N 0.000 description 1
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- DPOGTJDEMBEUSH-UHFFFAOYSA-N dicyclohexyl(ethyl)phosphane Chemical compound C1CCCCC1P(CC)C1CCCCC1 DPOGTJDEMBEUSH-UHFFFAOYSA-N 0.000 description 1
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- VPLLTGLLUHLIHA-UHFFFAOYSA-N dicyclohexyl(phenyl)phosphane Chemical compound C1CCCCC1P(C=1C=CC=CC=1)C1CCCCC1 VPLLTGLLUHLIHA-UHFFFAOYSA-N 0.000 description 1
- PYABLNMWNFFWDQ-UHFFFAOYSA-N dicyclohexyl(propan-2-yl)phosphane Chemical compound C1CCCCC1P(C(C)C)C1CCCCC1 PYABLNMWNFFWDQ-UHFFFAOYSA-N 0.000 description 1
- STLWGOOPIMPZEC-UHFFFAOYSA-N dicyclohexyl-(2,6-dimethoxyphenyl)phosphane Chemical compound COC1=CC=CC(OC)=C1P(C1CCCCC1)C1CCCCC1 STLWGOOPIMPZEC-UHFFFAOYSA-N 0.000 description 1
- NVCCUQKLTNUOTI-UHFFFAOYSA-N dicyclohexyl-(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 NVCCUQKLTNUOTI-UHFFFAOYSA-N 0.000 description 1
- MVJMDUZAQQJRAH-UHFFFAOYSA-N dicyclohexyl-(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C1CCCCC1)C1CCCCC1 MVJMDUZAQQJRAH-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- VIYIKMFRPUAPHN-UHFFFAOYSA-N diethyl(2-methylpropyl)phosphane Chemical compound CCP(CC)CC(C)C VIYIKMFRPUAPHN-UHFFFAOYSA-N 0.000 description 1
- OAQIQXVKEPRDOD-UHFFFAOYSA-N diethyl(heptyl)phosphane Chemical compound CCCCCCCP(CC)CC OAQIQXVKEPRDOD-UHFFFAOYSA-N 0.000 description 1
- JXZYJDIOJKWORY-UHFFFAOYSA-N diethyl(hexyl)phosphane Chemical compound CCCCCCP(CC)CC JXZYJDIOJKWORY-UHFFFAOYSA-N 0.000 description 1
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- ZBGVFVIFMRFLSQ-UHFFFAOYSA-N diethyl(octyl)phosphane Chemical compound CCCCCCCCP(CC)CC ZBGVFVIFMRFLSQ-UHFFFAOYSA-N 0.000 description 1
- VKFXAAKRTKERMI-UHFFFAOYSA-N diethyl(pentyl)phosphane Chemical compound CCCCCP(CC)CC VKFXAAKRTKERMI-UHFFFAOYSA-N 0.000 description 1
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- OWMJFBIZWDNTLY-UHFFFAOYSA-N diethyl(propan-2-yl)phosphane Chemical compound CCP(CC)C(C)C OWMJFBIZWDNTLY-UHFFFAOYSA-N 0.000 description 1
- SHCATAMMUJGPTD-UHFFFAOYSA-N diethyl(propyl)phosphane Chemical compound CCCP(CC)CC SHCATAMMUJGPTD-UHFFFAOYSA-N 0.000 description 1
- KIHNSNGSTARPGW-UHFFFAOYSA-N diethyl-(4-methoxyphenyl)phosphane Chemical compound CCP(CC)C1=CC=C(OC)C=C1 KIHNSNGSTARPGW-UHFFFAOYSA-N 0.000 description 1
- LASVOMFNNIOSAE-UHFFFAOYSA-N diheptyl(methyl)phosphane Chemical compound CCCCCCCP(C)CCCCCCC LASVOMFNNIOSAE-UHFFFAOYSA-N 0.000 description 1
- REKYWQFSUOYXIC-UHFFFAOYSA-N diheptyl(phenyl)phosphane Chemical compound CCCCCCCP(CCCCCCC)C1=CC=CC=C1 REKYWQFSUOYXIC-UHFFFAOYSA-N 0.000 description 1
- DNJWGDRCDNRDIL-UHFFFAOYSA-N diheptyl(propan-2-yl)phosphane Chemical compound CCCCCCCP(C(C)C)CCCCCCC DNJWGDRCDNRDIL-UHFFFAOYSA-N 0.000 description 1
- RXLRDQWFWTWSAH-UHFFFAOYSA-N diheptyl(propyl)phosphane Chemical compound CCCCCCCP(CCC)CCCCCCC RXLRDQWFWTWSAH-UHFFFAOYSA-N 0.000 description 1
- MRCWFLVFFDEGGJ-UHFFFAOYSA-N dihexyl(phenyl)phosphane Chemical compound CCCCCCP(CCCCCC)C1=CC=CC=C1 MRCWFLVFFDEGGJ-UHFFFAOYSA-N 0.000 description 1
- CBGZZRDXDBULAZ-UHFFFAOYSA-N dimethyl(2-methylpropyl)phosphane Chemical compound CC(C)CP(C)C CBGZZRDXDBULAZ-UHFFFAOYSA-N 0.000 description 1
- LFZKSOOXPOYSSJ-UHFFFAOYSA-N dimethyl(octyl)phosphane Chemical compound CCCCCCCCP(C)C LFZKSOOXPOYSSJ-UHFFFAOYSA-N 0.000 description 1
- IAJUXQDITQTUIR-UHFFFAOYSA-N dimethyl(pentyl)phosphane Chemical compound CCCCCP(C)C IAJUXQDITQTUIR-UHFFFAOYSA-N 0.000 description 1
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 description 1
- DDTJHNQEGUTUIJ-UHFFFAOYSA-N dimethyl(propan-2-yl)phosphane Chemical compound CC(C)P(C)C DDTJHNQEGUTUIJ-UHFFFAOYSA-N 0.000 description 1
- QVTPAZHGNYBKHE-UHFFFAOYSA-N dimethyl(propyl)phosphane Chemical compound CCCP(C)C QVTPAZHGNYBKHE-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- ASDULAWDDLZNHN-UHFFFAOYSA-N dioctyl(pentyl)phosphane Chemical compound CCCCCCCCP(CCCCC)CCCCCCCC ASDULAWDDLZNHN-UHFFFAOYSA-N 0.000 description 1
- HXUARCOTWDKZOU-UHFFFAOYSA-N dioctyl(phenyl)phosphane Chemical compound CCCCCCCCP(CCCCCCCC)C1=CC=CC=C1 HXUARCOTWDKZOU-UHFFFAOYSA-N 0.000 description 1
- AZKYRJFAQUTGPQ-UHFFFAOYSA-N dioctyl(propan-2-yl)phosphane Chemical compound CCCCCCCCP(C(C)C)CCCCCCCC AZKYRJFAQUTGPQ-UHFFFAOYSA-N 0.000 description 1
- PRBYIGPVGVDJLI-UHFFFAOYSA-N dioctyl(propyl)phosphane Chemical compound CCCCCCCCP(CCC)CCCCCCCC PRBYIGPVGVDJLI-UHFFFAOYSA-N 0.000 description 1
- BYYQOWAAZOHHFN-UHFFFAOYSA-N dioctylphosphane Chemical compound CCCCCCCCPCCCCCCCC BYYQOWAAZOHHFN-UHFFFAOYSA-N 0.000 description 1
- QDZAKCWPRPKCBW-UHFFFAOYSA-N dipentyl(phenyl)phosphane Chemical compound CCCCCP(CCCCC)C1=CC=CC=C1 QDZAKCWPRPKCBW-UHFFFAOYSA-N 0.000 description 1
- LLZAIAIZAVMQIG-UHFFFAOYSA-N diphenyl(propan-2-yl)phosphane Chemical compound C=1C=CC=CC=1P(C(C)C)C1=CC=CC=C1 LLZAIAIZAVMQIG-UHFFFAOYSA-N 0.000 description 1
- AAXGWYDSLJUQLN-UHFFFAOYSA-N diphenyl(propyl)phosphane Chemical compound C=1C=CC=CC=1P(CCC)C1=CC=CC=C1 AAXGWYDSLJUQLN-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
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- GWYXJFZWIXIPNV-UHFFFAOYSA-N ethyl(diheptyl)phosphane Chemical compound CCCCCCCP(CC)CCCCCCC GWYXJFZWIXIPNV-UHFFFAOYSA-N 0.000 description 1
- LEMQFDHLRUSMPZ-UHFFFAOYSA-N ethyl(dimethyl)phosphane Chemical compound CCP(C)C LEMQFDHLRUSMPZ-UHFFFAOYSA-N 0.000 description 1
- VRROQFXKEVCQBZ-UHFFFAOYSA-N ethyl(dioctyl)phosphane Chemical compound CCCCCCCCP(CC)CCCCCCCC VRROQFXKEVCQBZ-UHFFFAOYSA-N 0.000 description 1
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- GUZQPNDMHDZWCJ-UHFFFAOYSA-N ethyl-di(propan-2-yl)phosphane Chemical compound CCP(C(C)C)C(C)C GUZQPNDMHDZWCJ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000006492 halo alkyl aryl group Chemical group 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
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- WHAFDJWJDDPMDO-UHFFFAOYSA-N trimethyl(phenyl)phosphanium Chemical compound C[P+](C)(C)C1=CC=CC=C1 WHAFDJWJDDPMDO-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
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- DAGQYUCAQQEEJD-UHFFFAOYSA-N tris(2-methylpropyl)phosphane Chemical compound CC(C)CP(CC(C)C)CC(C)C DAGQYUCAQQEEJD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
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- B01J31/0268—Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous
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Abstract
本發明提供一種簡便且以低成本製造用於使環氧化物與二氧化碳反應而合成環狀碳酸酯且具有優異觸媒活性之非均相系觸媒的方法、利用該製造方法所獲得之觸媒、及使用該觸媒之環狀碳酸酯之合成方法。
本發明係一種觸媒之製造方法,其係用於使環氧化物與二氧化碳反應而合成環狀碳酸酯之觸媒之製造方法,且包含下述步驟(a)及(b):(a)使具有鹵烷基或鹵芳基之矽烷化合物與矽膠於二甲苯存在下進行反應,而獲得具有鹵烷基或鹵芳基之觸媒前驅物的步驟;(b)使步驟(a)中所獲得之觸媒前驅物與三級膦反應而獲得環狀碳酸酯合成用觸媒的步驟。
Description
本發明係關於一種環狀碳酸酯合成用觸媒之製造方法、利用該製造方法所獲得之觸媒、及使用該觸媒之環狀碳酸酯之合成方法。
環狀碳酸酯係作為有機溶劑、合成纖維加工劑、醫藥品原料、化妝品添加劑、鋰電池用電解液溶劑,進而作為伸烷基二醇及碳酸二烷基酯合成之中間物而用於廣泛用途之重要化合物之一。
先前,該環狀碳酸酯係藉由於均相系觸媒之存在下,於適當之加壓條件下使環氧化物與二氧化碳反應而合成。作為此種均相系觸媒,先前已知有鹼金屬等之鹵化物(專利文獻1)或四級銨鹽等鎓鹽(專利文獻2),且亦正用於工業。
然而,於使用此種均相系觸媒之情形時,通常必需反應混合物與觸媒之利用蒸餾等之分離操作,不僅製造步驟變複雜,亦有分離步驟中之觸媒之分解或副產物之產生等問題。
[專利文獻1]日本專利特公昭63-17072號公報
[專利文獻2]日本專利特開昭55-145623號公報
[專利文獻3]國際公開第2005/084801號
[專利文獻4]日本專利特開2008-296066號公報
因此,以觸媒分離製程之簡化為目的,而提出有將以鹵化物離子為抗衡離子之四級鏻基固定於矽膠等載體而成之非均相系觸媒(專利文獻3)。該觸媒係藉由使利用共價鍵將鹵烷基鏈固定於矽膠之市售之載體與三烷基膦反應,進行四級鏻化而製造。
然而,專利文獻3所記載之製造方法必須長時間於高溫下進行四級鏻化反應,又,即便長時間反應,大量之鹵烷基鏈亦未與上述膦反應而殘留。
又,利用共價鍵固定有鹵烷基鏈或鹵芳基鏈之矽膠即便不使用市售品,亦可例如藉由使3-溴丙基三乙氧基矽烷等矽烷化合物與矽膠於甲苯中於回流條件下進行反應而獲得,但關於該反應,通常若矽烷化合物之濃度變低,則反應速度變慢。因此,為了導入充分量之鹵烷基鏈,而採用下述方法:使用相對於矽膠為數倍~數十倍量之大為過量之矽烷化合物,或者反覆進行蒸餾反應液而提高矽烷化合物之濃度之操作等。
然而,於上述大量使用矽烷化合物之情形時,不僅有容易產生矽烷化合物彼此之縮合物而降低觸媒活性之情形,而且觸媒製造步驟中之廢棄物增加而降低觸媒之製造效率。又,關於一面將溶劑蒸餾去除一面進行反應之方法,反應裝置變複雜,且步驟數亦變多。
又,作為簡便製造如專利文獻3所記載之將以鹵化物離子為抗衡離子之四級鏻固定化而成之觸媒的方法,提出有預先使3-溴丙基三乙氧基矽烷與二苯基單烷基膦反應而進行四級鏻化,以其為觸媒交聯劑而對載體表面進行修飾之方法(專利文獻4)。
然而,於使用與二苯基單烷基膦反應而四級鏻化之矽烷化合物作為觸媒交聯劑之情形時,由於位阻而限制與矽膠表面鍵結之矽烷化合物之量,因此難以認為可擔載充分量之鹵素或磷。又,於矽膠之存
在下,四級鏻鹽與矽烷化合物進行反應而產生副產物,因此難以製造表現出與四級鏻鹽及矽烷化合物之使用量相稱之活性之觸媒。
因此,本發明提供一種簡便且以低成本製造用於使環氧化物與二氧化碳反應而合成環狀碳酸酯之具有優異觸媒活性之非均相系觸媒的方法、利用該製造方法所獲得之觸媒、及使用該觸媒之環狀碳酸酯之合成方法。
因此,本發明者等人反覆努力研究,結果發現,使具有鹵烷基或鹵芳基之矽烷化合物與矽膠於二甲苯存在下進行反應,獲得具有鹵烷基或鹵芳基之觸媒前驅物,繼而,使該觸媒前驅物與三級膦反應,藉此即便於上述矽烷化合物之使用量為少量之情形或反應時間較短之情形時,亦可簡便且以低成本製造環狀碳酸酯合成用觸媒,且該觸媒表現出優異之觸媒活性,從而完成本發明。
即,本發明提供一種觸媒之製造方法,其係用於使環氧化物與二氧化碳反應而合成環狀碳酸酯之觸媒之製造方法,且包含下述步驟(a)及(b):(a)使具有鹵烷基或鹵芳基之矽烷化合物與矽膠於二甲苯存在下進行反應,而獲得具有鹵烷基或鹵芳基之觸媒前驅物的步驟;(b)使步驟(a)中所獲得之觸媒前驅物與三級膦反應而獲得環狀碳酸酯合成用觸媒的步驟。
又,本發明提供一種觸媒,其係利用上述製造方法所獲得之用於使環氧化物與二氧化碳反應而合成環狀碳酸酯者。
進而,本發明提供一種環狀碳酸酯之合成方法,其係於上述觸媒之存在下使環氧化物與二氧化碳反應。
根據本發明之製造方法,即便於矽烷化合物之使用量為少量之
情形或反應時間較短之情形時,亦可簡便且以低成本製造可以高轉化率及高產率合成環狀碳酸酯且表現出優異觸媒活性的非均相系觸媒。
因此,本發明之觸媒可用作用於使環氧化物與二氧化碳反應而合成環狀碳酸酯之觸媒。又,根據本發明之環狀碳酸酯之合成方法,可以高轉化率及高產率合成環狀碳酸酯。
A‧‧‧高壓流體送液泵
B‧‧‧高壓流體送液泵
C‧‧‧流體混合器
D‧‧‧反應管
E‧‧‧壓力控制裝置
圖1係表示本發明之環狀碳酸酯之合成方法所使用之裝置之一例的示意圖。
<環狀碳酸酯合成用觸媒之製造方法>
本發明之用於使環氧化物與二氧化碳反應而合成環狀碳酸酯之觸媒之製造方法係包含上述步驟(a)及(b)者。
[步驟(a)]
步驟(a)係使具有鹵烷基或鹵芳基之矽烷化合物與矽膠於二甲苯存在下進行反應(矽烷化反應),而獲得具有鹵烷基或鹵芳基之觸媒前驅物的步驟。
藉由於步驟(a)中使用二甲苯作為溶劑,可獲得充分鹵素含量之觸媒前驅物。再者,關於矽膠之矽烷化反應,若矽烷化合物之濃度變低,則反應變慢,因此採用下述方法:於相對於所需之擔載量為數倍~數十倍量之大為過量之矽烷化合物之存在下進行反應;或者反覆進行適當蒸餾反應液,將一部分溶劑蒸餾去除來提高矽烷化合物之濃度之操作而進行反應等,但根據本發明之方法,即便於矽烷化合物之使用量為少量之情形或反應時間較短之情形時,亦可不採用如上所述之方法而獲得充分鹵素含量之觸媒前驅物。
上述二甲苯可為鄰二甲苯、間二甲苯、對二甲苯、混合二甲苯中之任一者。再者,二甲苯亦可與乙基苯等其他溶劑組合使用。
上述二甲苯之使用量並無特別限定,相對於矽膠100質量份,通常為100~1000質量份,較佳為100~750質量份,更佳為100~500質量份,進而較佳為200~300質量份。
又,作為上述步驟(a)中所使用之矽膠之平均細孔徑,就觸媒活性及抑制環狀碳酸酯合成中之副產物之觀點而言,較佳為3.5~50nm之範圍,較佳為3.5~25nm之範圍,更佳為5~20nm之範圍,尤佳為6~15nm之範圍。藉由使用此種範圍之平均細孔徑之矽膠,而變得容易控制觸媒之矽膠含量、磷含量。又,藉由將平均細孔徑設為3.5nm以上,而變得容易將三級膦導入至細孔內,可抑制於表面凝集、堵塞細孔等。
又,上述矽膠之比表面積較佳為80~2000m2/g之範圍,更佳為100~1000m2/g之範圍,進而較佳為150~750m2/g之範圍。
又,就分離回收等之操作性之方面而言,上述矽膠較佳為呈粒子之形態。粒子之形狀並無特別限定,例如可列舉:破碎狀、粒狀、珠粒狀、錠劑狀、顆粒狀、圓筒狀、粉體狀,亦可為不規則之形狀。於矽膠為珠粒狀之情形時,其粒徑較佳為0.1~10mm之範圍,更佳為0.2~8mm之範圍,進而較佳為0.5~5.0mm之範圍。又,於粉體狀之情形時,其粒度較佳為30~5000目,更佳為100~1000目。
再者,上述矽膠之平均細孔徑、比表面積、粒徑可藉由比表面積/細孔分佈測定裝置等進行測定。
又,矽膠較佳為預先進行乾燥者,更佳為吸附水分量為1質量%以下者(將相對於矽膠之吸附水分量調整為1質量%以下者)。藉由將吸附水分量設為1質量%以下,而抑制表面矽烷醇,抑制鹵烷基或鹵芳基之過量擔載,提高觸媒活性。
此處,所謂吸附水分量,係指存在於矽膠細孔內之水分量,可藉由熱重量測定裝置等進行測定。
上述矽膠之乾燥方法並無特別限定,例如可列舉:於減壓下或乾燥空氣(或惰性氣體)流通下進行加熱之方法、使用迪安-斯塔克分離器之回流處理等方法。該回流處理所使用之溶劑只要為可藉由共沸而去除水者,則並無特別限定,但就抑制由溶劑之置換引起之水分之帶入的觀點而言,較佳為將該溶劑直接設為於步驟(a)中使用之溶劑。
進而,矽膠亦可於上述乾燥前利用鹽酸等進行酸處理。
又,作為步驟(a)中所使用之含有鹵烷基或鹵芳基之矽烷化合物,較佳為下述式(1)所表示者。該矽烷化合物可單獨使用1種,或組合2種以上使用。
[化1]X-R1-Si(OR2)3 (1)
[式(1)中,R1表示碳數2~8之直鏈狀或支鏈狀之伸烷基、伸芳基、伸烷芳基(alkarylene)、伸芳基伸烷基或伸烷基伸芳基,R2表示碳數1~4之烷基,X表示鹵素原子]
上述式(1)中,作為R1所表示之碳數2~8之直鏈狀或支鏈狀之伸烷基,例如可列舉:伸乙基、三亞甲基、伸丙基、四亞甲基、五亞甲基、六亞甲基、七亞甲基、八亞甲基等。
又,R1所表示之伸芳基較佳為碳數6~10之伸芳基,例如可列舉:伸苯基、甲伸苯基等。
又,R1所表示之伸烷芳基較佳為碳數8~10之伸烷芳基,例如可列舉:苯二甲基等。
又,R1所表示之伸芳基伸烷基較佳為碳數6~10之伸芳基伸烷基,例如可列舉:伸苯基亞甲基、伸苯基伸乙基等。
又,R1所表示之伸烷基伸芳基較佳為碳數6~10之伸烷基伸芳
基,例如可列舉:亞甲基伸苯基、伸乙基伸苯基等。
該等中,較佳為碳數2~8之直鏈狀或支鏈狀之伸烷基,更佳為碳數2~6之直鏈狀或支鏈狀之伸烷基,尤佳為三亞甲基。
又,式(1)中,作為R2所表示之碳數1~4之烷基,可列舉:甲基、乙基、丙基、丁基,較佳為甲基、乙基,更佳為甲基。
式(1)中,作為X所表示之鹵素原子,可列舉:氯原子、溴原子、碘原子,較佳為溴原子。
作為式(1)所表示之矽烷化合物中之含有鹵烷基者之具體例,可列舉:鹵C2-8烷基三甲氧基矽烷、鹵C2-8烷基三乙氧基矽烷、鹵C2-8烷基三丙氧基矽烷、鹵烷基芳基三甲氧基矽烷、鹵烷基芳基三乙氧基矽烷、鹵烷基芳基三丙氧基矽烷、鹵烷基芳烷基三甲氧基矽烷、鹵烷基芳烷基三乙氧基矽烷、鹵烷基芳烷基三丙氧基矽烷等。
作為上述鹵C2-8烷基三甲氧基矽烷,例如可列舉:2-氯乙基三甲氧基矽烷、2-溴乙基三甲氧基矽烷、2-碘乙基三甲氧基矽烷、3-氯丙基三甲氧基矽烷、3-溴丙基三甲氧基矽烷、3-碘丙基三甲氧基矽烷、4-氯丁基三甲氧基矽烷、4-溴丁基三甲氧基矽烷、4-碘丁基三甲氧基矽烷、5-氯戊基三甲氧基矽烷、5-溴戊基三甲氧基矽烷、5-碘戊基三甲氧基矽烷、6-氯己基三甲氧基矽烷、6-溴己基三甲氧基矽烷、6-碘己基三甲氧基矽烷、7-氯庚基三甲氧基矽烷、7-溴庚基三甲氧基矽烷、7-碘庚基三甲氧基矽烷、8-氯辛基三甲氧基矽烷、8-溴辛基三甲氧基矽烷、8-碘辛基三甲氧基矽烷。
又,作為上述鹵C2-8烷基三乙氧基矽烷,例如可列舉:2-氯乙基三乙氧基矽烷、2-溴乙基三乙氧基矽烷、2-碘乙基三乙氧基矽烷、3-氯丙基三乙氧基矽烷、3-溴丙基三乙氧基矽烷、3-碘丙基三乙氧基矽烷、4-氯丁基三乙氧基矽烷、4-溴丁基三乙氧基矽烷、4-碘丁基三乙氧基矽烷、5-氯戊基三乙氧基矽烷、5-溴戊基三乙氧基矽烷、5-碘戊
基三乙氧基矽烷、6-氯己基三乙氧基矽烷、6-溴己基三乙氧基矽烷、6-碘己基三乙氧基矽烷、7-氯庚基三乙氧基矽烷、7-溴庚基三乙氧基矽烷、7-碘庚基三乙氧基矽烷、8-氯辛基三乙氧基矽烷、8-溴辛基三乙氧基矽烷、8-碘辛基三乙氧基矽烷。
又,作為上述鹵C2-8烷基三丙氧基矽烷,例如可列舉:2-氯乙基三丙氧基矽烷、2-溴乙基三丙氧基矽烷、2-碘乙基三丙氧基矽烷、3-氯丙基三丙氧基矽烷、3-溴丙基三丙氧基矽烷、3-碘丙基三丙氧基矽烷、4-氯丁基三丙氧基矽烷、4-溴丁基三丙氧基矽烷、4-碘丁基三丙氧基矽烷、5-氯戊基三丙氧基矽烷、5-溴戊基三丙氧基矽烷、5-碘戊基三丙氧基矽烷、6-氯己基三丙氧基矽烷、6-溴己基三丙氧基矽烷、6-碘己基三丙氧基矽烷、7-氯庚基三丙氧基矽烷、7-溴庚基三丙氧基矽烷、7-碘庚基三丙氧基矽烷、8-氯辛基三丙氧基矽烷、8-溴辛基三丙氧基矽烷、8-碘辛基三丙氧基矽烷。
又,作為上述鹵烷基芳基三甲氧基矽烷,例如可列舉:對氯甲基苯基三甲氧基矽烷、對(2-氯乙基)苯基三甲氧基矽烷、對溴甲基苯基三甲氧基矽烷、對(2-溴乙基)苯基三甲氧基矽烷、對碘甲基苯基三甲氧基矽烷、對(2-碘乙基)苯基三甲氧基矽烷。
又,作為上述鹵烷基芳基三乙氧基矽烷,例如可列舉:對氯甲基苯基三乙氧基矽烷、對(2-氯乙基)苯基三乙氧基矽烷、對溴甲基苯基三乙氧基矽烷、對(2-溴乙基)苯基三乙氧基矽烷、對碘甲基苯基三乙氧基矽烷、對(2-碘乙基)苯基三乙氧基矽烷。
又,作為上述鹵烷基芳基三丙氧基矽烷,例如可列舉:對氯甲基苯基三丙氧基矽烷、對(2-氯乙基)苯基三丙氧基矽烷、對溴甲基苯基三丙氧基矽烷、對(2-溴乙基)苯基三丙氧基矽烷、對碘甲基苯基三丙氧基矽烷、對(2-碘乙基)苯基三丙氧基矽烷。
又,作為上述鹵烷基芳烷基三甲氧基矽烷,例如可列舉:對氯
甲基苄基三甲氧基矽烷、對溴甲基苄基三甲氧基矽烷、對碘甲基苄基三甲氧基矽烷。
又,作為上述鹵烷基芳烷基三乙氧基矽烷,可列舉:對氯甲基苄基三乙氧基矽烷、對溴甲基苄基三乙氧基矽烷、對碘甲基苄基三乙氧基矽烷。
又,作為上述鹵烷基芳烷基三丙氧基矽烷,可列舉:對氯甲基苄基三丙氧基矽烷、對溴甲基苄基三丙氧基矽烷、對碘甲基苄基三丙氧基矽烷。
又,作為式(1)所表示之矽烷化合物中之含有鹵芳基者之具體例,可列舉:鹵芳基三烷氧基矽烷、鹵芳烷基三烷氧基矽烷等。
作為上述鹵芳基三烷氧基矽烷,可列舉:對氯苯基三甲氧基矽烷、對溴苯基三甲氧基矽烷、對氯苯基三乙氧基矽烷、對溴苯基三乙氧基矽烷、對氯苯基三丙氧基矽烷、對溴苯基三丙氧基矽烷。
又,作為上述鹵芳烷基三烷氧基矽烷,可列舉:對氯苄基三甲氧基矽烷、對溴苄基三甲氧基矽烷、對碘苄基三甲氧基矽烷、對氯苄基三乙氧基矽烷、對溴苄基三乙氧基矽烷、對碘苄基三乙氧基矽烷、對氯苄基三丙氧基矽烷、對溴苄基三丙氧基矽烷、對碘苄基三丙氧基矽烷等。
關於上述矽烷化合物之使用量,就觸媒活性及廉價地製造觸媒之觀點而言,相對於矽膠1莫耳,較佳為0.001~0.5莫耳,更佳為0.01~0.1莫耳,進而較佳為0.02~0.08莫耳,尤佳為0.025~0.06莫耳。
步驟(a)之反應溫度並無特別限定,較佳為50~160℃,更佳為80~150℃,進而較佳為100~140℃,進而較佳為110~140℃,進而較佳為125~140℃之範圍。可藉由將反應溫度設為160℃以下而抑制所擔載之矽烷化合物之分解,另一方面,可藉由設為50℃以上而加快反應速度。
步驟(a)之反應時間並無特別限定,較佳為1~30小時,更佳為3~28小時,尤佳為5~26小時。再者,根據本步驟(a),即便反應時間為5~10小時,亦可獲得充分鹵素含量之觸媒前驅物。
又,作為步驟(a)中所獲得之具有鹵烷基或鹵芳基之觸媒前驅物中之鹵素的含量,就觸媒活性之觀點而言,較佳為相對於每1g觸媒前驅物為1.0mmol以下,更佳為0.1~1.0mmol,進而較佳為0.2~0.95mmol,進而較佳為0.3~0.9mmol,進而較佳為0.3~0.75mmol,尤佳為0.3~0.5mmol。
藉由調整具有鹵烷基或鹵芳基之矽烷化合物之使用量且於二甲苯存在下進行步驟(a),可獲得上述範圍之鹵素含量之觸媒前驅物。又,藉由使用將上述吸附水分量調整為1質量%以下之矽膠,而變得更容易控制鹵素含量。
上述鹵素含量只要以與下述實施例相同之方式進行測定即可。
[步驟(b)]
步驟(b)係使步驟(a)中所獲得之觸媒前驅物與三級膦反應而獲得環狀碳酸酯合成用觸媒的步驟。藉由使觸媒前驅物與三級膦反應,而將觸媒前驅物之鹵烷基或鹵芳基轉換為以鹵化物陰離子為抗衡離子之四級鏻基。因此,環狀碳酸酯合成用觸媒具有以鹵化物陰離子為抗衡離子之四級鏻基。
作為步驟(b)中所使用之三級膦,較佳為下述式(2)所表示者。該三級膦可單獨使用1種或組合2種以上使用。
[式(2)中,R3~R5分別獨立表示碳數1~8之烷基、芳基、芳烷
基、烷氧基烷基、具有烷氧基作為取代基之芳基、或該等基所含有之1個以上之氫原子經包含雜原子之基取代者]
式(2)中,R3~R5所表示之碳數1~8之烷基可為直鏈狀、支鏈狀、環狀中之任一種,例如可列舉:甲基、乙基、丙基、異丙基、丁基、異丁基、戊基、己基、庚基、辛基、環己基等。
又,R3~R5所表示之芳基較佳為碳數6~10之芳基,例如可列舉:苯基、甲苯基、二甲苯基、萘基等。
又,R3~R5所表示之芳烷基較佳為碳數7~12之芳烷基,例如可列舉苄基等。
又,R3~R5所表示之烷氧基烷基較佳為碳數2~8之烷氧基烷基,例如可列舉甲氧基乙基等。
又,R3~R5所表示之具有烷氧基作為取代基之芳基較佳為碳數7~14之烷氧基芳基,例如可列舉:甲氧基苯基、二甲氧基苯基等。又,芳基所具有之烷氧基之個數及位置係任意,但較佳之烷氧基之個數為1~4個,更佳為1或2個。
再者,上述碳數1~8之烷基、芳基、芳烷基、烷氧基烷基、具有烷氧基作為取代基之芳基亦可使該等基所含有之1個以上之氫原子經包含雜原子之基取代。作為雜原子,可列舉:氮、氧、磷、硫、鹵素原子(氟原子等)等。
作為上述包含雜原子之基,可列舉:胺基、肼基、硝基、氰基、異氰基、脒基等含氮基;烷醯基、羧基、烷氧基羰基、羥基等含氧基;膦基、膦醯基、氧膦基等含磷基;磺基、硫基(sulfanyl)、烷基硫基(alkyl sulfanyl)、烷基磺醯基、烷基磺醯基胺基、烷基胺基磺醯基、烷基亞磺醯基、烷基胺基亞磺醯基、烷基亞磺醯基胺基、硫羧基等含硫基等。
如上所述之R3~R5中,較佳為碳數1~8之烷基,更佳為碳數1~8
之直鏈狀或支鏈狀之烷基,進而較佳為碳數1~4之直鏈狀或支鏈狀之烷基,尤佳為丁基。
作為上述式(2)所表示之化合物之具體例,可列舉:三C1-8烷基膦、三芳基膦、二芳基C1-8烷基膦、芳基二C1-8烷基膦、三芳烷基膦、二芳烷基C1-8烷基膦、二芳烷基芳基膦、芳烷基二C1-8烷基膦、芳烷基二芳基膦、三(烷氧基芳基)膦、雙(烷氧基芳基)C1-8烷基膦、雙(烷氧基芳基)芳基膦、雙(烷氧基芳基)芳烷基膦、(烷氧基芳基)二C1-8烷基膦、(二烷氧基芳基)二C1-8烷基膦、烷氧基芳基二芳基膦、(二烷氧基芳基)二芳基膦、烷氧基芳基二芳烷基膦、(二烷氧基芳基)二芳烷基膦。
作為上述三C1-8烷基膦,例如可列舉:三甲基膦、三乙基膦、三丙基膦、三異丙基膦、三正丁基膦、三異丁基膦、三戊基膦、三己基膦、三庚基膦、三辛基膦、三環己基膦、二甲基乙基膦、二甲基丙基膦、二甲基異丙基膦、二甲基正丁基膦、二甲基異丁基膦、二甲基戊基膦、二甲基己基膦、二甲基庚基膦、二甲基辛基膦、二甲基環己基膦、二乙基甲基膦、二乙基丙基膦、二乙基異丙基膦、二乙基正丁基膦、二乙基異丁基膦、二乙基戊基膦、二乙基己基膦、二乙基庚基膦、二乙基辛基膦、二乙基環己基膦、二丙基甲基膦、二丙基乙基膦、二丙基異丙基膦、二丙基正丁基膦、二丙基異丁基膦、二丙基戊基膦、二丙基己基膦、二丙基庚基膦、二丙基辛基膦、二丙基環己基膦、二異丙基甲基膦、二異丙基乙基膦、二異丙基丙基膦、二異丙基正丁基膦、二異丙基異丁基膦、二異丙基戊基膦、二異丙基己基膦、二異丙基庚基膦、二異丙基辛基膦、二異丙基環己基膦、二正丁基甲基膦、二正丁基乙基膦、二正丁基丙基膦、二正丁基異丙基膦、二正丁基異丁基膦、二正丁基戊基膦、二正丁基己基膦、二正丁基庚基膦、二正丁基辛基膦、二正丁基
環己基膦、二異丁基甲基膦、二異丁基乙基膦、二異丁基丙基膦、二異丁基異丙基膦、二異丁基正丁基膦、二異丁基戊基膦、二異丁基己基膦、二異丁基庚基膦、二異丁基辛基膦、二異丁基環己基膦、二戊基甲基膦、二戊基乙基膦、二戊基丙基膦、二戊基異丙基膦、二戊基正丁基膦、二戊基異丁基膦、二戊基己基膦、二戊基庚基膦、二戊基辛基膦、二戊基環己基膦、二己基甲基膦、二己基乙基膦、二己基丙基膦、二己基異丙基膦、二己基正丁基膦、二己基異丁基膦、二己基戊基膦、二己基庚基膦、二己基辛基膦、二己基環己基膦、二庚基甲基膦、二庚基乙基膦、二庚基丙基膦、二庚基異丙基膦、二庚基正丁基膦、二庚基異丁基膦、二庚基戊基膦、二庚基己基膦、二庚基辛基膦、二庚基環己基膦、二辛基甲基膦、二辛基乙基膦、二辛基丙基膦、二辛基異丙基膦、二辛基正丁基膦、二辛基異丁基膦、二辛基戊基膦、二辛基己基膦、二辛基庚基膦、二辛基環己基膦、二環己基甲基膦、二環己基乙基膦、二環己基丙基膦、二環己基異丙基膦、二環己基正丁基膦、二環己基異丁基膦、二環己基戊基膦、二環己基己基膦、二環己基庚基膦、二環己基辛基膦。
作為上述三芳基膦,可列舉:三苯基膦、三甲苯基膦、三-二甲苯基膦。
作為上述二芳基C1-8烷基膦,可列舉:二苯基甲基膦、二苯基乙基膦、二苯基丙基膦、二苯基異丙基膦、二苯基正丁基膦、二苯基異丁基膦、二苯基戊基膦、二苯基己基膦、二苯基庚基膦、二苯基辛基膦、二苯基環己基膦、二-甲苯基甲基膦、二-甲苯基乙基膦、二-甲苯基丙基膦、二-甲苯基異丙基膦、二-甲苯基正丁基膦、二-甲苯基異丁基膦、二-甲苯基戊基膦、二-甲苯基己基膦、二-甲苯基庚基膦、二-甲苯基辛基膦、二-甲苯基環己基膦、二-二甲苯基甲基膦、二-二甲苯
基乙基膦、二-二甲苯基丙基膦、二-二甲苯基異丙基膦、二-二甲苯基正丁基膦、二-二甲苯基異丁基膦、二-二甲苯基戊基膦、二-二甲苯基己基膦、二-二甲苯基庚基膦、二-二甲苯基辛基膦、二-二甲苯基環己基膦。
作為上述芳基二C1-8烷基膦,可列舉:苯基二甲基膦、苯基二乙基膦、苯基二丙基膦、苯基二異丙基膦、苯基二正丁基膦、苯基二異丁基膦、苯基二戊基膦、苯基二己基膦、苯基二庚基膦、苯基二辛基膦、苯基二環己基膦、甲苯基二甲基膦、甲苯基二乙基膦、甲苯基二丙基膦、甲苯基二異丙基膦、甲苯基二正丁基膦、甲苯基二異丁基膦、甲苯基二戊基膦、甲苯基二己基膦、甲苯基二庚基膦、甲苯基二辛基膦、甲苯基二環己基膦、二甲苯基二甲基膦、二甲苯基二乙基膦、二甲苯基二丙基膦、二甲苯基二異丙基膦、二甲苯基二正丁基膦、二甲苯基二異丁基膦、二甲苯基二戊基膦、二甲苯基二己基膦、二甲苯基二庚基膦、二甲苯基二辛基膦、二甲苯基二環己基膦。
作為上述三芳烷基膦,可列舉三苄基膦。
又,作為上述二芳烷基C1-8烷基膦,可列舉:二苄基甲基膦、二苄基乙基膦、二苄基丙基膦、二苄基異丙基膦、二苄基正丁基膦、二苄基異丁基膦、二苄基戊基膦、二苄基己基膦、二苄基庚基膦、二苄基辛基膦、二苄基環己基膦。
作為上述二芳烷基芳基膦,可列舉:二苄基苯基膦、二苄基甲苯基膦、二苄基二甲苯基膦。
作為上述芳烷基二C1-8烷基膦,可列舉:苄基二甲基膦、苄基二乙基膦、苄基二丙基膦、苄基二異丙基膦、苄基二正丁基膦、苄基二異丁基膦、苄基二戊基膦、苄基二己基膦、苄基二庚基膦、苄基二辛基膦、苄基二環己基膦。
作為上述芳烷基二芳基膦,可列舉:苄基二苯基膦、苄基二-甲
苯基膦、苄基二-二甲苯基膦。
作為上述三(烷氧基芳基)膦,可列舉:三(2,6-二甲氧基苯基)膦、三鄰甲氧基苯基膦、三對甲氧基苯基膦。
作為上述雙(烷氧基芳基)C1-8烷基膦,可列舉:雙(2,6-二甲氧基苯基)甲基膦、雙(2,6-二甲氧基苯基)乙基膦、雙(2,6-二甲氧基苯基)丙基膦、雙(2,6-二甲氧基苯基)異丙基膦、雙(2,6-二甲氧基苯基)正丁基膦、雙(2,6-二甲氧基苯基)異丁基膦、雙(2,6-二甲氧基苯基)戊基膦、雙(2,6-二甲氧基苯基)己基膦、雙(2,6-二甲氧基苯基)庚基膦、雙(2,6-二甲氧基苯基)辛基膦、雙(2,6-二甲氧基苯基)環己基膦、二鄰甲氧基苯基甲基膦、二鄰甲氧基苯基乙基膦、二鄰甲氧基苯基丙基膦、二鄰甲氧基苯基異丙基膦、二鄰甲氧基苯基正丁基膦、二鄰甲氧基苯基異丁基膦、二鄰甲氧基苯基戊基膦、二鄰甲氧基苯基己基膦、二鄰甲氧基苯基庚基膦、二鄰甲氧基苯基辛基膦、二鄰甲氧基苯基環己基膦、二對甲氧基苯基甲基膦、二對甲氧基苯基乙基膦、二對甲氧基苯基甲基膦、二對甲氧基苯基乙基膦、二對甲氧基苯基丙基膦、二對甲氧基苯基異丙基膦、二對甲氧基苯基正丁基膦、二對甲氧基苯基異丁基膦、二對甲氧基苯基戊基膦、二對甲氧基苯基己基膦、二對甲氧基苯基庚基膦、二對甲氧基苯基辛基膦、二對甲氧基苯基環己基膦。
作為上述雙(烷氧基芳基)芳基膦,可列舉:雙(2,6-二甲氧基苯基)苯基膦、雙(2,6-二甲氧基苯基)甲苯基膦、雙(2,6-二甲氧基苯基)二甲苯基膦、二鄰甲氧基苯基苯基膦、二鄰甲氧基苯基甲苯基膦、二鄰甲氧基苯基二甲苯基膦、二對甲氧基苯基苯基膦、二對甲氧基苯基甲苯基膦、二對甲氧基苯基二甲苯基膦。
作為上述雙(烷氧基芳基)芳烷基膦,可列舉:雙(2,6-二甲氧基苯基)苄基膦、二鄰甲氧基苯基苄基膦、二對甲氧基苯基苄基膦。
作為上述(烷氧基芳基)二C1-8烷基膦,可列舉:鄰甲氧基苯基二
甲基膦、鄰甲氧基苯基二乙基膦、鄰甲氧基苯基二丙基膦、鄰甲氧基苯基二異丙基膦、鄰甲氧基苯基二正丁基膦、鄰甲氧基苯基二異丁基膦、鄰甲氧基苯基二戊基膦、鄰甲氧基苯基二己基膦、鄰甲氧基苯基二庚基膦、鄰甲氧基苯基二辛基膦、鄰甲氧基苯基二環己基膦、對甲氧基苯基二甲基膦、對甲氧基苯基二乙基膦、對甲氧基苯基二丙基膦、對甲氧基苯基二異丙基膦、對甲氧基苯基二正丁基膦、對甲氧基苯基二異丁基膦、對甲氧基苯基二戊基膦、對甲氧基苯基二己基膦、對甲氧基苯基二庚基膦、對甲氧基苯基二辛基膦、對甲氧基苯基二環己基膦。
作為上述(二烷氧基芳基)二C1-8烷基膦,可列舉:2,6-二甲氧基苯基二甲基膦、2,6-二甲氧基苯基二乙基膦、2,6-二甲氧基苯基二丙基膦、2,6-二甲氧基苯基二異丙基膦、2,6-二甲氧基苯基二正丁基膦、2,6-二甲氧基苯基二異丁基膦、2,6-二甲氧基苯基二戊基膦、2,6-二甲氧基苯基二己基膦、2,6-二甲氧基苯基二庚基膦、2,6-二甲氧基苯基二辛基膦、2,6-二甲氧基苯基二環己基膦。
作為上述烷氧基芳基二芳基膦,可列舉:鄰甲氧基苯基二苯基膦、鄰甲氧基苯基二-甲苯基膦、鄰甲氧基苯基二-二甲苯基膦、對甲氧基苯基二苯基膦、對甲氧基苯基二-甲苯基膦、對甲氧基苯基二-二甲苯基膦。
作為上述(二烷氧基芳基)二芳基膦,可列舉:2,6-二甲氧基苯基二苯基膦、2,6-二甲氧基苯基二-甲苯基膦、2,6-二甲氧基苯基二-二甲苯基膦。
作為上述烷氧基芳基二芳烷基膦,可列舉:鄰甲氧基苯基二苄基膦、對甲氧基苯基二苄基膦。
作為上述(二烷氧基芳基)二芳烷基膦,可列舉:2,6-二甲氧基苯基二苄基膦。
關於三級膦之使用量,相對於步驟(a)中所使用之矽膠1莫耳,較佳為0.001~0.5莫耳,更佳為0.01~0.1莫耳,進而較佳為0.02~0.08莫耳,尤佳為0.025~0.06莫耳。
又,作為步驟(a)中所使用之具有鹵烷基或鹵芳基之矽烷化合物與上述三級膦之使用量的莫耳比[矽烷化合物/三級膦],就觸媒活性之觀點而言,較佳為0.1~15,更佳為0.1~7.5,進而較佳為0.1~1.2,進而較佳為0.2~1.0,進而較佳為0.3~0.9,進而較佳為0.4~0.9,尤佳為0.4~0.8。
又,步驟(b)較佳為於溶劑存在下進行,作為該溶劑,較佳為烴溶劑。
作為上述烴溶劑,可列舉:脂肪族烴溶劑、芳香族烴溶劑、脂環式烴溶劑。再者,脂肪族烴溶劑可為正十二烷等正鏈烷烴系溶劑、異十二烷等異烷烴系溶劑中之任一種。該等溶劑可單獨使用1種,或組合2種以上使用。
該等烴溶劑中,就環狀碳酸酯合成中之副反應抑制及反應速度之觀點而言,較佳為芳香族烴溶劑。作為該芳香族烴溶劑,可列舉:甲苯、二甲苯、乙基苯等,更佳為二甲苯。二甲苯可為鄰二甲苯、間二甲苯、對二甲苯、混合二甲苯中之任一者,亦可為含有乙基苯者。
再者,亦可將上述步驟(a)中所使用之溶劑直接設為步驟(b)之溶劑,藉此無需溶劑之去除或乾燥等程序,而可更簡便地獲得表現出優異觸媒活性之觸媒。
上述溶劑之使用量並無特別限定,相對於三級膦100質量份,通常為100~2000質量份,較佳為100~1750質量份,更佳為500~1500質量份。
又,步驟(b)之反應溫度並無特別限定,就抑制由熱引起之觸媒劣化及反應效率之觀點而言,較佳為60~160℃、更佳為100~
150℃、進而較佳為110~140℃之範圍。
又,步驟(b)之反應時間並無特別限定,就使磷含量變充分且抑制鹵素之脫離量之觀點而言,較佳為10~100小時,更佳為15~50小時。
再者,於上述各步驟中,觸媒前驅物及觸媒之單離只要視需要適當組合過濾、清洗、乾燥等通常之方法進行即可。
又,作為步驟(b)中所獲得之環狀碳酸酯合成用觸媒中之鹵素含量與磷含量之莫耳比[鹵素/磷],就觸媒活性及抑制環狀碳酸酯合成中之副產物之觀點而言,較佳為0.8~1.6,更佳為1.0~1.6。
上述莫耳比[鹵素/磷]係藉由於步驟(a)中使用二甲苯而變得容易調整。又,藉由具有鹵烷基或鹵芳基之矽烷化合物或三級膦之使用量或矽膠之平均細孔徑等而更容易進行控制。
又,作為環狀碳酸酯合成用觸媒中之鹵素含量,就觸媒活性及抑制環狀碳酸酯合成中之副產物之觀點而言,較佳為相對於每1g觸媒為0.25~0.8mmol,更佳為0.3~0.8mmol。
上述鹵素含量係藉由於步驟(a)中使用二甲苯而變得容易調整。又,藉由調整具有鹵烷基或鹵芳基之矽烷化合物之使用量或矽膠之平均細孔徑,或者使用將上述吸附水分量調整為1質量%以下之矽膠而更容易進行控制。
又,作為環狀碳酸酯合成用觸媒中之磷含量,就觸媒活性之觀點而言,較佳為相對於每1g觸媒為0.25~0.6mmol,更佳為0.3~0.6mmol。
上述磷含量係藉由於步驟(a)中使用二甲苯而變得容易調整。又,藉由調整三級膦之使用量或將矽膠之平均細孔徑設為3.5~25nm之範圍而更容易進行控制。
又,環狀碳酸酯合成用觸媒係非均相系觸媒(固體觸媒),且具有
細孔。作為其平均細孔徑,就觸媒活性之觀點而言,較佳為1nm~50nm之範圍,更佳為3~20nm之範圍,進而較佳為3.5~15nm之範圍,進而較佳為5~15nm之範圍,進而較佳為6~15nm之範圍。
又,作為環狀碳酸酯合成用觸媒之比表面積,較佳為80~2000m2/g之範圍,更佳為100~1000m2/g之範圍。
上述鹵素或磷之含量、平均細孔徑、比表面積只要以與下述實施例相同之方式進行測定即可。
並且,根據本發明之製造方法,即便於矽烷化合物之使用量為少量之情形或反應時間較短之情形時,亦可簡便且以低成本製造可以高轉化率、高選擇率且高產率合成環狀碳酸酯且表現出優異觸媒活性的非均相系觸媒。又,於使用利用此種製造方法所獲得之觸媒而合成環狀碳酸酯之情形時,溴丙醇或溴乙醇之類之副產物之產生亦較少。
本發明之觸媒可用作用於使環氧化物與二氧化碳反應而合成環狀碳酸酯之觸媒。
<環狀碳酸酯之合成方法>
本發明之環狀碳酸酯之合成方法係於利用上述製造方法所獲得之觸媒之存在下,使環氧化物與二氧化碳反應者。該合成方法除使用上述觸媒以外,只要依據常法進行即可。
上述觸媒之使用量只要適當調整即可,相對於環氧化物100質量份,通常為0.01~106質量份,較佳為0.1~105質量份,更佳為1~104質量份。
又,作為上述環氧化物,只要為結構式中包含至少1個環氧環(包含2個碳原子與1個氧原子之三員環)之化合物,則並無特別限定,例如可列舉:環氧乙烷、環氧丙烷、環氧丁烷、環氧異丁烷、乙烯基環氧乙烷、三氟甲基環氧乙烷、環氧環己烷、環氧苯乙烷、一氧化丁二烯、二氧化丁二烯、2-甲基-3-苯基環氧丁烷、氧化蒎烯、四氰基環氧
乙烷等。
此種環氧化物中,較佳為下述式(3)所表示者。
[式(3)中,R6及R7分別獨立表示氫原子、碳數1~6之烷基、碳數1~6之鹵烷基、碳數2~6之烯基、或碳數2~6之鹵烯基]
上述R6及R7所表示之烷基、鹵烷基之碳數較佳為1~4。作為該烷基,例如可列舉與上述R2相同者。鹵烷基中之鹵素原子可列舉與上述X相同者。
此種式(3)所表示者中,較佳為環氧乙烷、環氧丙烷。
本發明之環狀碳酸酯之合成方法可於溶劑存在下及不存在下中之任一種情況下進行。於使用溶劑之情形時,除作為目標化合物之環狀碳酸酯外,使用戊烷、己烷、庚烷等脂肪族烴類;苯、甲苯等芳香族烴類;甲醇、乙醇等醇類;丙酮、甲基乙基酮等酮類;二乙醚、甲基第三丁基醚、四氫呋喃、二烷等醚類;二甲基甲醯胺、二甲基乙醯胺等醯胺類;乙酸乙酯等酯類;三乙胺、吡啶、甲基嗒、N,N'-二甲基嗒酮等三級胺類;二丁基硫醚等硫醚類;三丁基膦等膦類等即可,該等可單獨使用1種,或組合2種以上使用。
又,關於本發明之環狀碳酸酯之合成方法之反應溫度,就反應效率之觀點而言,較佳為20~160℃、更佳為50~150℃、進而較佳為80~140℃之範圍。
又,反應壓力並無特別限定,較佳為0.1~100MPa、更佳為0.5~50MPa、進而較佳為1.0~25MPa之範圍。
又,反應時間並無特別限定,通常為0.1~10小時,較佳為0.5~5小時。
又,本發明之環狀碳酸酯之合成方法可採用攪拌式或固定床式等通常所使用之方法作為反應方式,又,可為分批式、半分批式、連續流通式中之任一種方法。
分批式例如可以下述方式進行。於具備攪拌裝置之高壓釜中添加環氧化物及觸媒後,填充二氧化碳並進行密封。其後,一面攪拌高壓釜內一面加熱至特定溫度,進而填充二氧化碳,藉此將內壓調整為特定壓力,反應特定時間後,利用所需方法分離產生之環狀碳酸酯。
關於連續流通式,例如使用如圖1所示之連結高壓流體送液泵(A、B)、流體混合器(C)、反應管(D)、壓力控制裝置(E)、溫度控制裝置(F)等而成之流通反應裝置(圖1),將環氧化物與二氧化碳混合後,於填充有觸媒之反應管內(D)進行加熱,連續進行反應即可。又,亦可使除成為原料之環氧化物與二氧化碳以外之成為溶劑之物質共存並進行流通。
再者,觸媒之前處理並非特別需要,但可藉由於反應前於20~140℃、較佳為50~120℃下於真空排氣下、或於氦氣、氬氣、氮氣、二氧化碳等惰性氣體氣流中進行處理,而提高環狀碳酸酯之產率。
又,根據本發明之環狀碳酸酯之合成方法,可合成上述環氧化物之環氧環被轉換為碳酸酯環(具有O-CO-O鍵之五員環)之環狀碳酸酯。作為此種環狀碳酸酯,例如可列舉:碳酸乙二酯、碳酸丙二酯、碳酸丁二酯、碳酸異丁二酯、碳酸三氟甲基乙二酯、碳酸乙烯基乙二酯、環己烯碳酸酯、苯乙烯碳酸酯、丁二烯單碳酸酯、丁二烯二碳酸酯、碳酸氯甲酯、蒎烯碳酸酯、碳酸四氰基乙二酯等。
並且,根據該等本發明之環狀碳酸酯之合成方法,可以高轉化率、高選擇率且高產率合成環狀碳酸酯。又,關於該合成方法,溴丙
醇或2-溴乙醇之類之副產物之產生亦較少。
以下,列舉實施例,對本發明詳細進行說明,但本發明並不限定於該等實施例。再者,矽膠之平均細孔徑、比表面積及粒徑(或粒度)係製造商之標稱值。
又,於各實施例及比較例中使用之分析方法係如下所述。
(1)於觸媒之製造中,溴及磷修飾量之測定係使用螢光X射線分析(裝置:製品名「System3270」(理學電機工業公司製造),測定條件:Rh球管、管電壓50kV、管電流50mV、真空環境,檢測器:SC(Scintillation Counter,閃爍計數器)、F-PC(Flow Proportional Counter,流氣正比計數器))。
(2)於環狀碳酸酯之合成中,反應液之組成分析係使用氣相層析法。分析條件係如下所述。
裝置:製品名「GC-2010Plus」(島津製作所公司製造)
檢測器:FID(Flame Ionization Detector,火焰離子化檢測器)
INJ溫度:150℃
DET溫度:260℃
樣品量:0.3μL
分流比:5
管柱:DB-624(60m、0.32mmID、1.8μm、Agilent公司製造)
管柱溫度:70℃、3分鐘-5℃/分鐘-120℃-10℃/分鐘-250℃、5分鐘(計31分鐘)
製造例1-1:觸媒前驅物X-1之製造
將珠粒狀矽膠(FUJI SILYSIA CHEMICAL製造之CARiACT Q-10(平均細孔徑10nm、粒徑1.2~2.4mm、比表面積300m2/g))10g與二甲苯25mL添加於具備迪安-斯塔克分離器之50mL燒瓶中,於140℃
回流下,進行2小時二甲苯-水之共沸脫水,而將矽膠中之水分去除。繼而,自50mL燒瓶卸下迪安-斯塔克分離器,將燒瓶內進行氮氣置換後,滴加3-溴丙基三甲氧基矽烷1.1g(4.5mmol,相對於矽膠1g為0.45mmol)。將其直接於135℃下進行7小時加熱回流,藉此進行矽烷化反應。
繼而,藉由過濾而分離獲得之反應物,利用丙酮充分進行清洗。再者,藉由氣相層析儀分析而確認清洗後之液體所含有之3-溴丙基三甲氧基矽烷未達50ppm。將獲得之反應物投入至50mL燒瓶中,於120℃下進行2小時減壓乾燥,而獲得觸媒前驅物X-1(溴丙基化矽膠)。將分析結果示於表1。
製造例1-2:觸媒前驅物X-2之製造
將加熱時間自7小時變更為26小時,除此以外,以與製造例1-1相同之程序製造觸媒前驅物X-2。將分析結果示於表1。
製造例1-3:觸媒前驅物X-3之製造
將加熱溫度自135℃變更為110℃,將加熱時間自7小時變更為8小時,除此以外,以與製造例1-1相同之程序製造觸媒前驅物X-3。將分析結果示於表1。
製造例1-4:觸媒前驅物X-4之製造
將加熱時間自8小時變更為26小時,除此以外,以與製造例1-3相同之程序製造觸媒前驅物X-4。將分析結果示於表1。
製造例2-1:觸媒前驅物T-1之製造
將反應溶劑自二甲苯變更為甲苯,將加熱溫度自135℃變更為110℃(回流),將加熱時間自7小時變更為8小時,除此以外,以與製造例1-1相同之程序製造觸媒前驅物T-1。將分析結果示於表1。
製造例2-2:觸媒前驅物T-2之製造
將加熱時間自8小時變更為26小時,除此以外,以與製造例2-1相
同之程序製造觸媒前驅物T-2。將分析結果示於表1。
製造例2-3:觸媒前驅物T-3之製造
將加熱時間自8小時變更為49小時,除此以外,以與製造例2-1相同之程序製造觸媒前驅物T-3。將分析結果示於表1。
製造例2-4:觸媒前驅物T-4之製造
將3-溴丙基三甲氧基矽烷之滴加量變更為2.4g(9.9mmol,相對於矽膠1g為0.99mmol),除此以外,以與製造例2-1相同之程序製造觸媒前驅物T-4。將分析結果示於表1。
如表1所示,藉由使用二甲苯作為矽烷化反應之溶劑,而即便含鹵烷基或鹵芳基矽烷化合物之使用量為少量且反應時間較短,亦可擔載充分量之鹵素。於使用甲苯作為矽烷化反應之溶劑之情形時,為了以少量之矽烷化合物擔載充分量之鹵素,而必需長時間之反應(製造例2-3),又,為了於短時間內擔載充分量之鹵素,而必須使用與實際所擔載之鹵素量相比大為過量之含鹵烷基或鹵芳基矽烷化合物(製造例2-4)。
實施例1:觸媒XX-1之製造
將9g製造例1-1中所獲得之觸媒前驅物X-1與二甲苯30mL添加於50mL燒瓶中,將燒瓶內進行氮氣置換後,滴加三正丁基膦1.8g。將其直接於135℃下進行24小時加熱回流,藉此進行四級鏻化反應。反應後,藉由過濾而分離反應物,利用丙酮充分進行清洗。再者,藉由氣相層析儀分析而確認清洗後之液體所含有之三正丁基膦未達50ppm。將獲得之反應物投入至50mL燒瓶中,於120℃下進行2小時減壓乾燥,而獲得目標之觸媒XX-1(經溴化三丁基鏻表面修飾之矽膠)。將分析結果示於表2。
實施例2:XX-2之製造
將觸媒前驅物X-1變更為觸媒前驅物X-2,除此以外,以與實施例1相同之程序製造觸媒XX-2。將分析結果示於表2。
比較例1及2:觸媒TX-1、TX-3之製造
將觸媒前驅物X-1分別變更為觸媒前驅物T-1、T-3,除此以外,以與實施例1相同之程序製造觸媒TX-1、TX-3。將分析結果示於表2。
實施例3:碳酸丙二酯之合成
藉由以下之分批式方法而進行碳酸丙二酯之合成,並對觸媒活性進行評價。
於裝有攪拌子之50mL之高壓釜中添加800mg實施例1中所製備之觸媒XX-1,於120℃下進行1小時減壓乾燥。利用氮氣使高壓釜恢復至大氣壓並恢復至室溫後,添加環氧丙烷3.5g(60mmol)。繼而,預填充二氧化碳直至1.5MPa,其後,一面藉由轉子以1000rpm攪拌高壓釜內一面加熱至100℃,進而填充二氧化碳,藉此將內壓調整為3MPa,進行1小時反應。冷卻後,排出殘留之二氧化碳,將高壓釜內釋壓。藉由氣相層析儀對獲得之反應液進行分析。將結果示於表2。
再者,檢測到作為反應雜質之丙二醇、2-溴丙醇及1-溴-2-丙醇。
表2中亦一併表示該等溴丙醇之檢測量。
實施例4:碳酸丙二酯之合成
將觸媒XX-1變更為觸媒XX-2,除此以外,以與實施例3相同之程序,藉由分批式反應而合成碳酸丙二酯,並進行觸媒活性之評價。將結果示於表2。
比較例3及4:碳酸丙二酯之合成
將觸媒XX-1變更為觸媒TX-1、TX-3,除此以外,以與實施例3相同之程序,藉由分批式反應而合成碳酸丙二酯,並進行觸媒活性之評價。將結果示於表2。
實施例5:觸媒XX-5之製造
(觸媒前驅物之製造)
將珠粒狀矽膠(FUJI SILYSIA CHEMICAL製造之CARiACT Q-10(平均細孔徑10nm、粒徑1.2~2.4mm、比表面積300m2/g))2000g與二甲苯5000mL添加於具備迪安-斯塔克分離器之10L附帶攪拌翼之三口燒瓶中,於140℃回流下進行2小時二甲苯-水之共沸脫水,而將矽膠中之水分去除。再者,此時之二甲苯溶劑中之水分量為14ppm。繼而,將迪安-斯塔克分離器卸下,將燒瓶內進行氮氣置換後,滴加3-溴丙基三甲氧基矽烷219g(0.846mol)。將其直接於135℃下進行7小時加熱回流,藉此進行矽烷化反應。
繼而,藉由過濾而分離獲得之反應物,利用二甲苯清洗2次,而獲得含有二甲苯之觸媒前驅物X-5(溴丙基化矽膠)3810g。
再者,藉由氣相層析儀分析而確認清洗2次後之液體所含有之3-溴丙基三甲氧基矽烷未達50ppm。獲得之觸媒前驅物之利用螢光X射線分析所得之Br修飾量測定結果為0.38mmol/g。又,可估算二甲苯之含有率為57質量%,獲得之前驅物為約2170g。
(觸媒之製造)
將獲得之觸媒前驅物X-5與二甲苯5000mL添加於10L附帶攪拌翼之三口燒瓶中,將燒瓶內進行氮氣置換後,滴加三正丁基膦453g。將其直接於120℃下進行25小時加熱,藉此進行四級鏻化反應。反應後,藉由過濾而分離反應物,利用丙酮清洗6次。再者,藉由氣相層析儀分析而確認清洗6次後之液體所含有之三正丁基膦未達50ppm。將獲得之反應物於氮氣氣流下,於120℃下進行5小時減壓乾燥,而獲得目標之觸媒XX-5(經溴化三丁基鏻表面修飾之矽膠)2328g。將觸媒之分析結果示於表3。
實施例6:碳酸乙二酯之合成
藉由以下之分批式方法而進行碳酸乙二酯之合成,並對觸媒XX-5之觸媒活性進行評價。
於裝有攪拌子之50mL之高壓釜中添加800mg實施例5中所製備之觸媒XX-5,於120℃下進行1小時減壓乾燥。繼而,利用氮氣使高壓釜恢復至大氣壓並恢復至室溫,添加環氧乙烷2.8g(60mmol)。預填充二氧化碳直至1.5MPa,其後,一面藉由轉子以1000rpm攪拌高壓釜內一面加熱至100℃,進而填充二氧化碳,藉此將內壓調整為5.0MPa,進行1小時反應。冷卻後,排出殘留之二氧化碳,將高壓釜內釋壓。獲得之碳酸乙二酯之熔點為36℃,因此於高壓釜中加入乙腈溶劑4g,使反應液溶解。藉由氣相層析儀對獲得之反應液進行分析,而求出環氧乙烷轉化率、碳酸乙二酯選擇率、產率及表觀之一級反應速度常數k。將結果示於表4。
再者,表觀之一級反應速度常數k係根據下述式求出。
k=-ln(1-X/100)/t
式中,X係轉化率(%),t係反應時間(hr)。
再者,於氣相層析圖中,檢測到作為反應雜質之乙二醇、二乙二醇、2-溴乙醇。表4中亦一併表示2-溴乙醇之檢測量。
實施例7:碳酸乙二酯之合成
利用研缽粉碎觸媒XX-5,將獲得之粉末過篩並回收粒徑為200-
400目者後加以使用,除此以外,以與實施例6相同之程序,藉由分批式反應而合成碳酸乙二酯,並進行觸媒活性之評價。將結果示於表4。
如上述實施例所示,若使用藉由本發明之製造方法而獲得之觸媒,則可以較高之轉化率及產率合成環狀碳酸酯,又,可抑制溴丙醇或2-溴乙醇等雜質之產生。
Claims (10)
- 一種觸媒之製造方法,其係用於使環氧化物與二氧化碳反應而合成環狀碳酸酯之觸媒之製造方法,且包含下述步驟(a)及(b):(a)使具有鹵烷基或鹵芳基之矽烷化合物與矽膠於二甲苯存在下進行反應,而獲得具有鹵烷基或鹵芳基之觸媒前驅物的步驟;(b)使步驟(a)中所獲得之觸媒前驅物與三級膦反應而獲得環狀碳酸酯合成用觸媒的步驟。
- 如請求項1之製造方法,其中具有鹵烷基或鹵芳基之矽烷化合物之使用量相對於矽膠1莫耳為0.01~0.1莫耳。
- 如請求項1之製造方法,其中步驟(a)之反應時間為1~30小時。
- 如請求項1之製造方法,其中步驟(a)之反應溫度為50~160℃。
- 如請求項1之製造方法,其中步驟(b)係於烴溶劑存在下進行。
- 如請求項5之製造方法,其中烴溶劑為二甲苯。
- 如請求項1之製造方法,其中步驟(a)中所使用之矽膠之吸附水分量為1質量%以下。
- 一種觸媒,其係利用如請求項1至7中任一項之製造方法獲得之用於使環氧化物與二氧化碳反應而合成環狀碳酸酯者。
- 一種環狀碳酸酯之合成方法,其係於如請求項8之觸媒之存在下,使環氧化物與二氧化碳反應。
- 如請求項9之合成方法,其中環氧化物為選自環氧乙烷及環氧丙烷之1種以上。
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