JPH0323548B2 - - Google Patents
Info
- Publication number
- JPH0323548B2 JPH0323548B2 JP12127882A JP12127882A JPH0323548B2 JP H0323548 B2 JPH0323548 B2 JP H0323548B2 JP 12127882 A JP12127882 A JP 12127882A JP 12127882 A JP12127882 A JP 12127882A JP H0323548 B2 JPH0323548 B2 JP H0323548B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- alcohol
- alkylene
- quaternary phosphonium
- carbonate
- 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.)
- Expired
Links
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 38
- -1 alkylene carbonate Chemical compound 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 34
- 125000002947 alkylene group Chemical group 0.000 claims description 23
- 150000004714 phosphonium salts Chemical group 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000001569 carbon dioxide Substances 0.000 claims description 19
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 59
- 239000000047 product Substances 0.000 description 21
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 10
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- DEQIBPVIPZNOQI-UHFFFAOYSA-N 4,4,4-triphenylbutylphosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1C(C=1C=CC=CC=1)(CCC[PH3+])C1=CC=CC=C1 DEQIBPVIPZNOQI-UHFFFAOYSA-N 0.000 description 1
- BJWMSGRKJIOCNR-UHFFFAOYSA-N 4-ethenyl-1,3-dioxolan-2-one Chemical compound C=CC1COC(=O)O1 BJWMSGRKJIOCNR-UHFFFAOYSA-N 0.000 description 1
- ZKOGUIGAVNCCKH-UHFFFAOYSA-N 4-phenyl-1,3-dioxolan-2-one Chemical compound O1C(=O)OCC1C1=CC=CC=C1 ZKOGUIGAVNCCKH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- VFHDRNQWRHHHOD-UHFFFAOYSA-M butyl(tripropyl)phosphanium;iodide Chemical compound [I-].CCCC[P+](CCC)(CCC)CCC VFHDRNQWRHHHOD-UHFFFAOYSA-M 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- XTUSLLYSMVWGPS-UHFFFAOYSA-N carbonic acid;cyclohexene Chemical compound OC(O)=O.C1CCC=CC1 XTUSLLYSMVWGPS-UHFFFAOYSA-N 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- PPEVHNOHOYGLOT-UHFFFAOYSA-M cyclohexyl(tripropyl)phosphanium;chloride Chemical compound [Cl-].CCC[P+](CCC)(CCC)C1CCCCC1 PPEVHNOHOYGLOT-UHFFFAOYSA-M 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- KYDKTXWTQADWLD-UHFFFAOYSA-M ethyl(tripropyl)phosphanium;chloride Chemical compound [Cl-].CCC[P+](CC)(CCC)CCC KYDKTXWTQADWLD-UHFFFAOYSA-M 0.000 description 1
- CKRRDFVUVGYRGA-UHFFFAOYSA-M ethyl-dimethyl-phenylphosphanium;iodide Chemical compound [I-].CC[P+](C)(C)C1=CC=CC=C1 CKRRDFVUVGYRGA-UHFFFAOYSA-M 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- VBLKCVJGAOUJAL-UHFFFAOYSA-M methyl(tripropyl)phosphanium;iodide Chemical compound [I-].CCC[P+](C)(CCC)CCC VBLKCVJGAOUJAL-UHFFFAOYSA-M 0.000 description 1
- RXTHPQHHNPSSJR-UHFFFAOYSA-M octyl(tripropyl)phosphanium;iodide Chemical compound [I-].CCCCCCCC[P+](CCC)(CCC)CCC RXTHPQHHNPSSJR-UHFFFAOYSA-M 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HWBDDQTXHOVRCJ-UHFFFAOYSA-M phenyl(tripropyl)phosphanium;bromide Chemical compound [Br-].CCC[P+](CCC)(CCC)C1=CC=CC=C1 HWBDDQTXHOVRCJ-UHFFFAOYSA-M 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 1
- AXTXARBFPWQUQA-UHFFFAOYSA-M tetraoctylphosphanium;chloride Chemical compound [Cl-].CCCCCCCC[P+](CCCCCCCC)(CCCCCCCC)CCCCCCCC AXTXARBFPWQUQA-UHFFFAOYSA-M 0.000 description 1
- SMGSPBKMKYMJPQ-UHFFFAOYSA-M tetrapropylphosphanium;bromide Chemical compound [Br-].CCC[P+](CCC)(CCC)CCC SMGSPBKMKYMJPQ-UHFFFAOYSA-M 0.000 description 1
- XOTZDSWJKMKAMT-UHFFFAOYSA-M tributyl(ethyl)phosphanium;bromide Chemical compound [Br-].CCCC[P+](CC)(CCCC)CCCC XOTZDSWJKMKAMT-UHFFFAOYSA-M 0.000 description 1
- AEMACIJBXGZKLE-UHFFFAOYSA-M tributyl(hexyl)phosphanium;chloride Chemical compound [Cl-].CCCCCC[P+](CCCC)(CCCC)CCCC AEMACIJBXGZKLE-UHFFFAOYSA-M 0.000 description 1
- XKFPGUWSSPXXMF-UHFFFAOYSA-N tributyl(methyl)phosphanium Chemical compound CCCC[P+](C)(CCCC)CCCC XKFPGUWSSPXXMF-UHFFFAOYSA-N 0.000 description 1
- RLZMYANQLOCZOB-UHFFFAOYSA-M tributyl(methyl)phosphanium;iodide Chemical compound [I-].CCCC[P+](C)(CCCC)CCCC RLZMYANQLOCZOB-UHFFFAOYSA-M 0.000 description 1
- WJLSOXBTGDOFOQ-UHFFFAOYSA-N tributyl(propyl)phosphanium Chemical compound CCCC[P+](CCC)(CCCC)CCCC WJLSOXBTGDOFOQ-UHFFFAOYSA-N 0.000 description 1
- DFMBSBCYSILJJK-UHFFFAOYSA-N tricyclohexylmethylphosphanium;iodide Chemical compound [I-].C1CCCCC1C(C1CCCCC1)([PH3+])C1CCCCC1 DFMBSBCYSILJJK-UHFFFAOYSA-N 0.000 description 1
- BDJIGLJMZADFCA-UHFFFAOYSA-M tricyclopentyl(2-methylpropyl)phosphanium;chloride Chemical compound [Cl-].C1CCCC1[P+](C1CCCC1)(CC(C)C)C1CCCC1 BDJIGLJMZADFCA-UHFFFAOYSA-M 0.000 description 1
- HEHKYZZEWNRUFC-UHFFFAOYSA-M trihexyl(octyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC HEHKYZZEWNRUFC-UHFFFAOYSA-M 0.000 description 1
- XMQSELBBYSAURN-UHFFFAOYSA-M triphenyl(propyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC)C1=CC=CC=C1 XMQSELBBYSAURN-UHFFFAOYSA-M 0.000 description 1
- IZYFBZDLXRHRLF-UHFFFAOYSA-N tritylphosphane;hydroiodide Chemical compound [I-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 IZYFBZDLXRHRLF-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12127882A JPS5913776A (ja) | 1982-07-14 | 1982-07-14 | アルキレンカ−ボネ−トの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12127882A JPS5913776A (ja) | 1982-07-14 | 1982-07-14 | アルキレンカ−ボネ−トの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5913776A JPS5913776A (ja) | 1984-01-24 |
| JPH0323548B2 true JPH0323548B2 (ko) | 1991-03-29 |
Family
ID=14807290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12127882A Granted JPS5913776A (ja) | 1982-07-14 | 1982-07-14 | アルキレンカ−ボネ−トの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5913776A (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3529263A1 (de) * | 1985-08-16 | 1987-02-19 | Hoechst Ag | Verfahren zur herstellung von 2-oxo-1,3-dioxolanen |
| CN1053393C (zh) * | 1996-01-03 | 2000-06-14 | 南开大学 | 用于二氧化碳合成碳酸酯的催化剂 |
| KR100391845B1 (ko) | 2000-02-11 | 2003-07-16 | 한국과학기술연구원 | 금속할로겐 화합물과 피리딘 리간드로 구성된 촉매에 의한알킬렌카보네이트의 합성 |
| KR100359874B1 (ko) | 2000-02-11 | 2002-11-07 | 한국과학기술연구원 | 알킬렌카보네이트 합성용 고활성 촉매 |
| JP4984139B2 (ja) * | 2007-05-29 | 2012-07-25 | 国立大学法人 岡山大学 | 環状炭酸エステルの合成のための固定化触媒に用いる触媒架橋剤の製造方法、及びその固定化触媒の製造方法、及びその固定化触媒に用いる触媒架橋剤、及びその固定化触媒 |
| KR101821987B1 (ko) | 2015-09-18 | 2018-01-26 | 한국과학기술원 | 고리형 카보네이트 제조용 금속 촉매, 이를 이용한 고리형 카보네이트의 제조방법 및 제조된 고리형 카보네이트의 용도 |
| KR102100611B1 (ko) | 2018-08-17 | 2020-04-14 | 충남대학교산학협력단 | 고리형 카보네이트 제조용 금속 착화합물 촉매 및 이를 이용한 고리형 카보네이트의 제조방법 |
| KR102127112B1 (ko) | 2018-08-17 | 2020-06-26 | 충남대학교산학협력단 | 초가교 바이페닐 중합체를 이용한 고리형 카보네이트의 제조방법 및 초가교 바이페닐 중합체 |
| KR20200094400A (ko) | 2019-01-30 | 2020-08-07 | 대케미칼 주식회사 | 고리형 카보네이트계 화합물의 제조방법 |
-
1982
- 1982-07-14 JP JP12127882A patent/JPS5913776A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5913776A (ja) | 1984-01-24 |
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