JP2013155134A - 1−アルキルイミダゾール化合物の製造法 - Google Patents
1−アルキルイミダゾール化合物の製造法 Download PDFInfo
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- JP2013155134A JP2013155134A JP2012016830A JP2012016830A JP2013155134A JP 2013155134 A JP2013155134 A JP 2013155134A JP 2012016830 A JP2012016830 A JP 2012016830A JP 2012016830 A JP2012016830 A JP 2012016830A JP 2013155134 A JP2013155134 A JP 2013155134A
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- Prior art keywords
- alkylimidazole
- reaction
- glyoxal
- compound
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims abstract description 38
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229940015043 glyoxal Drugs 0.000 claims abstract description 19
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 13
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 9
- -1 primary amine compound Chemical class 0.000 claims abstract description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 23
- 239000012808 vapor phase Substances 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- GRSDFNBEEJUAFT-UHFFFAOYSA-N 1-(2,2-dimethylpropyl)imidazole Chemical compound CC(C)(C)CN1C=CN=C1 GRSDFNBEEJUAFT-UHFFFAOYSA-N 0.000 description 1
- NPOZBHCPELPGKW-UHFFFAOYSA-N 1-(2-methylpropyl)imidazole Chemical compound CC(C)CN1C=CN=C1 NPOZBHCPELPGKW-UHFFFAOYSA-N 0.000 description 1
- CECNZZAKLLEZQO-UHFFFAOYSA-N 1-(3-methylbutyl)imidazole Chemical compound CC(C)CCN1C=CN=C1 CECNZZAKLLEZQO-UHFFFAOYSA-N 0.000 description 1
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 description 1
- YEXVVXDMRKHBKQ-UHFFFAOYSA-N 1-cycloheptylimidazole Chemical compound C1CCCCCC1N1C=NC=C1 YEXVVXDMRKHBKQ-UHFFFAOYSA-N 0.000 description 1
- VGZINEPOBWTUEH-UHFFFAOYSA-N 1-cyclohexylimidazole Chemical compound C1CCCCC1N1C=NC=C1 VGZINEPOBWTUEH-UHFFFAOYSA-N 0.000 description 1
- KMSLKJVJKLQNBB-UHFFFAOYSA-N 1-cyclooctylimidazole Chemical compound C1CCCCCCC1N1C=NC=C1 KMSLKJVJKLQNBB-UHFFFAOYSA-N 0.000 description 1
- MRXUDQKHRDLLHV-UHFFFAOYSA-N 1-cyclopentylimidazole Chemical compound C1CCCC1N1C=NC=C1 MRXUDQKHRDLLHV-UHFFFAOYSA-N 0.000 description 1
- IWDFHWZHHOSSGR-UHFFFAOYSA-N 1-ethylimidazole Chemical compound CCN1C=CN=C1 IWDFHWZHHOSSGR-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- KGWVFQAPOGAVRF-UHFFFAOYSA-N 1-hexylimidazole Chemical compound CCCCCCN1C=CN=C1 KGWVFQAPOGAVRF-UHFFFAOYSA-N 0.000 description 1
- KLMZKZJCMDOKFE-UHFFFAOYSA-N 1-octylimidazole Chemical compound CCCCCCCCN1C=CN=C1 KLMZKZJCMDOKFE-UHFFFAOYSA-N 0.000 description 1
- UPYVYJSWGZMBOU-UHFFFAOYSA-N 1-pentylimidazole Chemical compound CCCCCN1C=CN=C1 UPYVYJSWGZMBOU-UHFFFAOYSA-N 0.000 description 1
- IPIORGCOGQZEHO-UHFFFAOYSA-N 1-propan-2-ylimidazole Chemical compound CC(C)N1C=CN=C1 IPIORGCOGQZEHO-UHFFFAOYSA-N 0.000 description 1
- IYVYLVCVXXCYRI-UHFFFAOYSA-N 1-propylimidazole Chemical compound CCCN1C=CN=C1 IYVYLVCVXXCYRI-UHFFFAOYSA-N 0.000 description 1
- XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 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 description 1
- HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000012495 reaction gas Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
【解決手段】 グリオキサール、ホルムアルデヒド、アンモニア及び一級アミン化合物を気相反応させることを特徴とする1−アルキルイミダゾール化合物の製造法。
【選択図】なし
Description
1−アルキルイミダゾール化合物は、医薬、農薬、機能性材料等の中間体として有用な化合物である。
1−アルキルイミダゾール化合物を製造する方法としては、グリオキサール、ホルムアルデヒド、アンモニア及びメチルアミンを液相バッチ反応させる方法により、収率70%で1−メチルイミダゾールを得る方法が知られている(特許文献1参照)。
転化率(%)=反応したグリオキサール(モル)/供給したグリオキサール(モル)×100
収率(%)=反応により生成した1−アルキルイミダゾール(4)(モル)/供給したグリオキサール(モル)×100
ガスクロマトグラフ:島津製作所製GC−2010
カラム:J&W社製、DB−WAX、30m、内径0.32mm,膜厚0.25μm
温度:50℃(3min)→(15℃/min)→200℃(0min)→(20℃/min)→250℃(9.5min)
内径19mmのパイレックス(登録商標)製のガラス管にカーボランダムを85ml充填した。この充填層を200℃に保ち、ここに、グリオキサール(40%水溶液):ホルムアルデヒド(37%水溶液):アンモニア:メチルアミン(40%水溶液)=1:1.2:3.9:1.2(モル比)の混合物を、グリオキサール基準で滞留時間=7.8(秒)で上部から通過させた。生成物は100mlの水に吸収させて捕集した。反応開始後30分で充填層を250℃に昇温し、その後30分が経過した時点で充填層の温度が250℃で安定していることを確認後、生成物をガスクロマトグラフィーで分析した結果、1−メチルイミダゾールの収率は85%であった。
反応管上部から流すガスの組成をグリオキサール:ホルムアルデヒド:アンモニア:メチルアミン=1:1.5:4.1:1.5(モル比)に変えた以外は、実施例1と同様の方法で反応を実施した。1−メチルイミダゾールの収率は84%であった。
Claims (2)
- グリオキサール、ホルムアルデヒド、アンモニア及び一級アミン化合物を気相反応させることを特徴とする1−アルキルイミダゾール化合物の製造法。
- 一級アミン化合物がメチルアミンである請求項1に記載の1−アルキルイミダゾール化合物の製造法。
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Publications (2)
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JP2013155134A true JP2013155134A (ja) | 2013-08-15 |
JP5912584B2 JP5912584B2 (ja) | 2016-04-27 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106432086A (zh) * | 2016-08-12 | 2017-02-22 | 江苏康乐新材料科技有限公司 | 一种制备1‑甲基咪唑的方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5661359A (en) * | 1979-10-08 | 1981-05-26 | Basf Ag | Manufacture of 11substituted imidazole |
JPH03169865A (ja) * | 1989-11-29 | 1991-07-23 | Mitsui Toatsu Chem Inc | 1―置換イミダゾール類の製造法 |
JP2002255941A (ja) * | 2001-03-02 | 2002-09-11 | Koei Chem Co Ltd | イミダゾール化合物の製造法 |
CN101633642A (zh) * | 2009-08-12 | 2010-01-27 | 曾舟华 | N-烷基咪唑的制备方法 |
-
2012
- 2012-01-30 JP JP2012016830A patent/JP5912584B2/ja active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5661359A (en) * | 1979-10-08 | 1981-05-26 | Basf Ag | Manufacture of 11substituted imidazole |
JPH03169865A (ja) * | 1989-11-29 | 1991-07-23 | Mitsui Toatsu Chem Inc | 1―置換イミダゾール類の製造法 |
JP2002255941A (ja) * | 2001-03-02 | 2002-09-11 | Koei Chem Co Ltd | イミダゾール化合物の製造法 |
CN101633642A (zh) * | 2009-08-12 | 2010-01-27 | 曾舟华 | N-烷基咪唑的制备方法 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106432086A (zh) * | 2016-08-12 | 2017-02-22 | 江苏康乐新材料科技有限公司 | 一种制备1‑甲基咪唑的方法 |
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |