JP7233439B2 - 環状カーボネートを連続的に調製する方法 - Google Patents
環状カーボネートを連続的に調製する方法 Download PDFInfo
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- JP7233439B2 JP7233439B2 JP2020555003A JP2020555003A JP7233439B2 JP 7233439 B2 JP7233439 B2 JP 7233439B2 JP 2020555003 A JP2020555003 A JP 2020555003A JP 2020555003 A JP2020555003 A JP 2020555003A JP 7233439 B2 JP7233439 B2 JP 7233439B2
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- 150000005676 cyclic carbonates Chemical class 0.000 title claims description 54
- 238000000034 method Methods 0.000 title claims description 46
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 82
- 150000001875 compounds Chemical class 0.000 claims description 50
- -1 epoxide compound Chemical class 0.000 claims description 45
- 229910052782 aluminium Inorganic materials 0.000 claims description 42
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 claims description 41
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 41
- 239000001569 carbon dioxide Substances 0.000 claims description 41
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 36
- 239000000539 dimer Substances 0.000 claims description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 19
- 238000004821 distillation Methods 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 18
- 150000002924 oxiranes Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical group BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 11
- 239000000725 suspension Substances 0.000 claims description 11
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 239000000377 silicon dioxide Substances 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical compound CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000047 product Substances 0.000 description 28
- 239000003054 catalyst Substances 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000010926 purge Methods 0.000 description 8
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 230000008929 regeneration Effects 0.000 description 7
- 238000011069 regeneration method Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 5
- 238000009825 accumulation Methods 0.000 description 5
- 230000007420 reactivation Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910001868 water Inorganic materials 0.000 description 3
- 239000010457 zeolite Substances 0.000 description 3
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000012465 retentate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910008051 Si-OH Inorganic materials 0.000 description 1
- 229910006358 Si—OH Inorganic materials 0.000 description 1
- 229910000611 Zinc aluminium Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- HXFVOUUOTHJFPX-UHFFFAOYSA-N alumane;zinc Chemical compound [AlH3].[Zn] HXFVOUUOTHJFPX-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940094522 laponite Drugs 0.000 description 1
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—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
- C07D317/10—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
- 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
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
- C07D317/38—Ethylene carbonate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—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
- C07D317/10—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
- C07D317/14—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
(a)二酸化炭素を、液体環状カーボネート、及びハロゲン化化合物によって活性化される、担持された二量体アルミニウムサレン錯体の懸濁液中で、エポキシド化合物と接触させ、ここで、エポキシド化合物は二酸化炭素と反応して環状カーボネート生成物となり、担持された二量体サレン錯体の一部は失活する工程、
(b)環状カーボネート生成物の一部を、担持された二量体アルミニウムサレン錯体から分離して、環状カーボネート生成物、二酸化炭素、エポキシド化合物及びハロゲン化化合物を含む混合物を得る工程、
(c)ハロゲン化化合物を環状カーボネート生成物から分離して、精製された環状カーボネート生成物を得る工程、及び、
(d)工程(c)で得られたハロゲン化化合物の全部又は一部を用いて、失活した、担持された二量体サレン錯体を活性化する工程、
を含む方法。
Claims (20)
- ハロゲン化化合物によって活性化される、担持された二量体アルミニウムサレン錯体の存在下で、エポキシド化合物を二酸化炭素と反応させることによって、環状カーボネート生成物を連続的に調製する方法であって、以下の工程、
(a)二酸化炭素を、液体環状カーボネート、及びハロゲン化化合物によって活性化される、担持された二量体アルミニウムサレン錯体の懸濁液中で、エポキシド化合物と接触させ、ここで、エポキシド化合物は二酸化炭素と反応して環状カーボネート生成物となり、担持された二量体サレン錯体の一部は失活する工程、
(b)環状カーボネート生成物の一部を、担持された二量体アルミニウムサレン錯体から分離して、環状カーボネート生成物、二酸化炭素、エポキシド化合物及びハロゲン化化合物を含む混合物を得る工程、
(c)ハロゲン化化合物を環状カーボネート生成物から分離して、精製された環状カーボネート生成物を得る工程、及び
(d)工程(c)で得られたハロゲン化化合物の全部又は一部を用いて、失活した、担持された二量体サレン錯体を活性化する工程
を含む方法。 - 前記工程(a)の温度が20~150℃の間であり、圧力が0.1~0.5MPaの間であり、温度が選択された圧力での前記生成物の沸点より低い、請求項1に記載の方法。
- 前記工程(a)が、二酸化炭素及びエポキシド化合物が連続的に反応器に供給され、環状カーボネート生成物の一部が液体流の一部として連続的に抜き取られる、連続的に操作される攪拌反応器において実施される、請求項1又は2に記載の方法。
- 前記エポキシド化合物が2~8個の炭素原子を有する、請求項1~3のいずれか一項記載の方法。
- 前記エポキシド化合物が、エチレンオキシド、プロピレンオキシド、ブチレンオキシド、ペンテンオキシド、グリシドール又はスチレンオキシドである、請求項4に記載の方法。
- 前記工程(b)の分離が、環状カーボネートと担持された二量体アルミニウムサレン錯体との間の異なる質量密度及び/又はサイズを利用する、請求項1~5のいずれか一項に記載の方法。
- 前記工程(b)の分離がフィルターによって行われる、請求項6に記載の方法。
- 前記工程(b)の分離が遠心力を用いて行われる、請求項6に記載の方法。
- 前記工程(c)が蒸留によって行われ、蒸留工程において、二酸化炭素、ハロゲン化化合物、エポキシド化合物及び環状カーボネート生成物を含む混合物が、二酸化炭素、ハロゲン化化合物、エポキシド化合物及び環状カーボネート生成物の別々の流れに分離される、請求項1~8のいずれか一項に記載の方法。
- 前記工程(b)で得られた混合物中のエポキシド化合物の含有率を減少させて、エポキシド含有率が低下した混合物を得て、得られた混合物が蒸留工程(c)で分離される、請求項9に記載の方法。
- 前記エポキシド化合物の減少が、第2の反応工程において、担持された二量体アルミニウムサレン錯体の存在下で、エポキシド化合物を二酸化炭素と接触させることによって達成される、請求項10に記載の方法。
- 前記失活した、担持された二量体アルミニウムサレン錯体が、工程(a)を実施しながらハロゲン化化合物と接触させることによって活性化される、請求項1~11のいずれか一項に記載の方法。
- 前記失活した、担持された二量体アルミニウムサレン錯体が、失活した、担持された二量体アルミニウムサレン錯体を、環状カーボネート生成物の存在下で、ハロゲン化化合物と接触させることにより、工程(a)とは別の工程(e)で活性化される、請求項1~11のいずれか一項に記載の方法。
- 前記ハロゲン化化合物と担持された二量体アルミニウムサレン錯体のモル比が、工程(e)において5:1より大きい、請求項13に記載の方法。
- 工程(a)及び(e)が2つ以上の並列運転される反応器で実施され、工程(e)が1つ以上の反応器で実施される場合に、工程(a)が残りの反応器の少なくとも1つで実施される、請求項13又は14に記載の方法。
- 前記担体Sが、10~2000μmの間の平均直径を有する粒子から構成される、請求項16に記載の方法。
- 前記担体Sが、シリカ、アルミナ、チタニア、シリカ質MCM-41又はシリカ質MCM-48からなる群から選択される粒子である、請求項17に記載の方法。
- 前記ハロゲン化物がハロゲン化ベンジルである、請求項1~18のいずれか一項に記載の方法。
- 前記ハロゲン化ベンジルが臭化ベンジルである、請求項19に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL2020163 | 2017-12-22 | ||
NL2020163A NL2020163B1 (en) | 2017-12-22 | 2017-12-22 | Process to continuously prepare a cyclic carbonate |
PCT/NL2018/050854 WO2019125151A1 (en) | 2017-12-22 | 2018-12-18 | Process to continuously prepare a cyclic carbonate |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2021508736A JP2021508736A (ja) | 2021-03-11 |
JPWO2019125151A5 JPWO2019125151A5 (ja) | 2023-01-19 |
JP7233439B2 true JP7233439B2 (ja) | 2023-03-06 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2020555003A Active JP7233439B2 (ja) | 2017-12-22 | 2018-12-18 | 環状カーボネートを連続的に調製する方法 |
Country Status (12)
Country | Link |
---|---|
US (1) | US11053210B2 (ja) |
EP (1) | EP3728213B1 (ja) |
JP (1) | JP7233439B2 (ja) |
KR (1) | KR102452490B1 (ja) |
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CN110684005A (zh) * | 2019-10-31 | 2020-01-14 | 大连理工大学 | 一种制备环状碳酸酯的循环喷射式连续反应工艺 |
KR102505184B1 (ko) * | 2019-08-21 | 2023-03-02 | 주식회사 엘지화학 | 폴리알킬렌 카보네이트의 제조방법 |
NL2024243B1 (en) | 2019-11-15 | 2021-07-29 | New Green World B V | Process to continuously prepare a cyclic carbonate |
US20220388973A1 (en) * | 2019-11-15 | 2022-12-08 | New Green World B.V. | Process to continuously prepare a cyclic carbonate |
NL2024242B1 (en) | 2019-11-15 | 2021-07-29 | New Green World B V | Process to continuously prepare a cyclic carbonate |
JP2023549793A (ja) | 2020-11-12 | 2023-11-29 | ニュー・グリーン・ワールド・ベー・フェー | 環状炭酸塩を調製する方法 |
KR102383931B1 (ko) * | 2021-04-08 | 2022-04-08 | 아사히 가세이 가부시키가이샤 | 환상 알킬렌카보네이트의 공업적 제조 방법 |
WO2022171906A2 (en) | 2021-04-28 | 2022-08-18 | Torrgas Technology B.V. | Process to prepare lower olefins |
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WO2009109765A1 (en) | 2008-03-07 | 2009-09-11 | University Of Newcastle Upon Tyne | Synthesis of cyclic carbonates |
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TWI636980B (zh) * | 2013-07-19 | 2018-10-01 | 獨立行政法人產業技術綜合研究所 | Method for producing cyclic carbonate |
CN105381819B (zh) * | 2015-12-09 | 2018-04-10 | 大连理工大学 | 负载型双季铵盐催化剂及其制备方法和环状碳酸酯的制备方法 |
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NL2020163B1 (en) | 2019-05-22 |
KR102452490B1 (ko) | 2022-10-07 |
EP3728213A1 (en) | 2020-10-28 |
CA3084335A1 (en) | 2019-06-27 |
SA520412275B1 (ar) | 2023-02-12 |
US20200399239A1 (en) | 2020-12-24 |
ES2903541T3 (es) | 2022-04-04 |
BR112020012638A2 (pt) | 2020-12-01 |
CN111615510A (zh) | 2020-09-01 |
CN111615510B (zh) | 2023-08-01 |
KR20200091433A (ko) | 2020-07-30 |
WO2019125151A1 (en) | 2019-06-27 |
US11053210B2 (en) | 2021-07-06 |
EP3728213B1 (en) | 2021-10-27 |
PL3728213T3 (pl) | 2022-05-02 |
JP2021508736A (ja) | 2021-03-11 |
SG11202005008TA (en) | 2020-06-29 |
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