JP2005306820A - α,β−不飽和カルボニル化合物の製造方法及びα,β−不飽和カルボニル化合物 - Google Patents
α,β−不飽和カルボニル化合物の製造方法及びα,β−不飽和カルボニル化合物 Download PDFInfo
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- JP2005306820A JP2005306820A JP2004129605A JP2004129605A JP2005306820A JP 2005306820 A JP2005306820 A JP 2005306820A JP 2004129605 A JP2004129605 A JP 2004129605A JP 2004129605 A JP2004129605 A JP 2004129605A JP 2005306820 A JP2005306820 A JP 2005306820A
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- 150000001728 carbonyl compounds Chemical class 0.000 title claims abstract description 88
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 68
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 238000005882 aldol condensation reaction Methods 0.000 claims abstract description 18
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims description 83
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 claims description 34
- CHCCBPDEADMNCI-UHFFFAOYSA-N 3-Methyl-2-cyclopenten-1-one Chemical compound CC1=CC(=O)CC1 CHCCBPDEADMNCI-UHFFFAOYSA-N 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 abstract description 8
- 239000003054 catalyst Substances 0.000 abstract description 7
- -1 aldehyde compound Chemical class 0.000 description 29
- 230000035484 reaction time Effects 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 14
- 239000004576 sand Substances 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 229910021642 ultra pure water Inorganic materials 0.000 description 7
- 239000012498 ultrapure water Substances 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000004904 shortening Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- VAMUJZGXPJBNCL-UHFFFAOYSA-N 6-oxoheptanal Chemical compound CC(=O)CCCCC=O VAMUJZGXPJBNCL-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 0 *C(C(*)(*1)C1(*)C1(*)*)C1=O Chemical compound *C(C(*)(*1)C1(*)C1(*)*)C1=O 0.000 description 2
- VAIFYHGFLAPCON-UHFFFAOYSA-N 1,3-Diacetylpropane Chemical compound CC(=O)CCCC(C)=O VAIFYHGFLAPCON-UHFFFAOYSA-N 0.000 description 2
- AZRRZGIBBLWSSQ-UHFFFAOYSA-N 4-ethyl-7-phenyl-3,5-diazabicyclo[2.2.2]octane-2,6-dione Chemical class N1C(=O)C2C(=O)NC1(CC)CC2C1=CC=CC=C1 AZRRZGIBBLWSSQ-UHFFFAOYSA-N 0.000 description 2
- KEHNRUNQZGRQHU-UHFFFAOYSA-N 4-oxopentanal Chemical compound CC(=O)CCC=O KEHNRUNQZGRQHU-UHFFFAOYSA-N 0.000 description 2
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- ZRZHAVVBRGELRV-UHFFFAOYSA-N 7-oxooctanal Chemical compound CC(=O)CCCCCC=O ZRZHAVVBRGELRV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 125000004989 dicarbonyl group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
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- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical class CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- APAPZQYXOGNKGH-UHFFFAOYSA-N nonane-2,8-dione Chemical compound CC(=O)CCCCCC(C)=O APAPZQYXOGNKGH-UHFFFAOYSA-N 0.000 description 2
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- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- RDYZEHHXISBFMS-UHFFFAOYSA-N 1-hydroxyheptane-2,6-dione Chemical compound CC(=O)CCCC(=O)CO RDYZEHHXISBFMS-UHFFFAOYSA-N 0.000 description 1
- YXADPHVQSSNJLB-UHFFFAOYSA-N 1-hydroxyhexane-2,5-dione Chemical compound CC(=O)CCC(=O)CO YXADPHVQSSNJLB-UHFFFAOYSA-N 0.000 description 1
- NYLORKCBIYQWAF-UHFFFAOYSA-N 1-methoxyhexane-2,5-dione Chemical compound COCC(=O)CCC(C)=O NYLORKCBIYQWAF-UHFFFAOYSA-N 0.000 description 1
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 1
- KCVSCETUCBKXJI-UHFFFAOYSA-N 1-phenylheptane-2,6-dione Chemical compound CC(=O)CCCC(=O)CC1=CC=CC=C1 KCVSCETUCBKXJI-UHFFFAOYSA-N 0.000 description 1
- UCMOERVVSJLUHT-UHFFFAOYSA-N 1-phenylhexane-2,5-dione Chemical compound CC(=O)CCC(=O)CC1=CC=CC=C1 UCMOERVVSJLUHT-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- IDAHIBMEKOEBRG-UHFFFAOYSA-N 2-methyl-4-oxopentanal Chemical compound O=CC(C)CC(C)=O IDAHIBMEKOEBRG-UHFFFAOYSA-N 0.000 description 1
- MNBADNSBGCNGGB-UHFFFAOYSA-N 2-methyl-5-oxohexanal Chemical compound O=CC(C)CCC(C)=O MNBADNSBGCNGGB-UHFFFAOYSA-N 0.000 description 1
- KPDKSDHXZBWZDL-UHFFFAOYSA-N 2-methyl-6-oxoheptanal Chemical compound O=CC(C)CCCC(C)=O KPDKSDHXZBWZDL-UHFFFAOYSA-N 0.000 description 1
- FDMAFOTXGNYBFG-UHFFFAOYSA-N 2-methylcycloheptan-1-one Chemical compound CC1CCCCCC1=O FDMAFOTXGNYBFG-UHFFFAOYSA-N 0.000 description 1
- LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical compound CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 description 1
- DOPVNVIYCBRHHW-UHFFFAOYSA-N 2-methylcyclononan-1-one Chemical compound CC1CCCCCCCC1=O DOPVNVIYCBRHHW-UHFFFAOYSA-N 0.000 description 1
- MJFJFHJQZCMMKL-UHFFFAOYSA-N 2-methylcyclooctan-1-one Chemical compound CC1CCCCCCC1=O MJFJFHJQZCMMKL-UHFFFAOYSA-N 0.000 description 1
- DLRSDHOEMSSMCY-UHFFFAOYSA-N 2-phenylhexanal Chemical compound CCCCC(C=O)C1=CC=CC=C1 DLRSDHOEMSSMCY-UHFFFAOYSA-N 0.000 description 1
- WUWOZSJWGAXIAD-UHFFFAOYSA-N 3-hydroxyheptane-2,6-dione Chemical compound CC(=O)CCC(O)C(C)=O WUWOZSJWGAXIAD-UHFFFAOYSA-N 0.000 description 1
- MXGSILCFPNVDMX-UHFFFAOYSA-N 3-hydroxyhexane-2,5-dione Chemical compound CC(=O)CC(O)C(C)=O MXGSILCFPNVDMX-UHFFFAOYSA-N 0.000 description 1
- BRLDEYSTUKAWET-UHFFFAOYSA-N 3-hydroxyoctane-2,7-dione Chemical compound CC(=O)CCCC(O)C(C)=O BRLDEYSTUKAWET-UHFFFAOYSA-N 0.000 description 1
- AXJIRRZMWXMFMM-UHFFFAOYSA-N 3-methoxyheptane-2,6-dione Chemical compound CC(=O)CCC(C(=O)C)OC AXJIRRZMWXMFMM-UHFFFAOYSA-N 0.000 description 1
- QFGFRRPRGKYJLY-UHFFFAOYSA-N 3-methoxyhexane-2,5-dione Chemical compound COC(C(C)=O)CC(C)=O QFGFRRPRGKYJLY-UHFFFAOYSA-N 0.000 description 1
- GYMFZWLPVSVKBF-UHFFFAOYSA-N 3-methoxyoctane-2,7-dione Chemical compound COC(C(C)=O)CCCC(C)=O GYMFZWLPVSVKBF-UHFFFAOYSA-N 0.000 description 1
- GQHWESFTVGVFIA-UHFFFAOYSA-N 3-methyl-4-oxopentanal Chemical compound CC(=O)C(C)CC=O GQHWESFTVGVFIA-UHFFFAOYSA-N 0.000 description 1
- YSJGFZKUCZEJSW-UHFFFAOYSA-N 3-methyl-5-oxohexanal Chemical compound O=CCC(C)CC(C)=O YSJGFZKUCZEJSW-UHFFFAOYSA-N 0.000 description 1
- XXMZWYJISVJDBF-UHFFFAOYSA-N 3-methyl-6-oxoheptanal Chemical compound O=CCC(C)CCC(C)=O XXMZWYJISVJDBF-UHFFFAOYSA-N 0.000 description 1
- ODCUSTWYZNMGAI-UHFFFAOYSA-N 3-methyl-7-oxooctanal Chemical compound O=CCC(C)CCCC(C)=O ODCUSTWYZNMGAI-UHFFFAOYSA-N 0.000 description 1
- YLOUWNWIFUFLQS-UHFFFAOYSA-N 3-methylheptane-2,6-dione Chemical compound CC(=O)C(C)CCC(C)=O YLOUWNWIFUFLQS-UHFFFAOYSA-N 0.000 description 1
- NLLILAUVOOREKR-UHFFFAOYSA-N 3-methylhexane-2,5-dione Chemical compound CC(=O)C(C)CC(C)=O NLLILAUVOOREKR-UHFFFAOYSA-N 0.000 description 1
- XAKNPTVPASRQNY-UHFFFAOYSA-N 3-methyloctane-2,7-dione Chemical compound CC(=O)C(C)CCCC(C)=O XAKNPTVPASRQNY-UHFFFAOYSA-N 0.000 description 1
- FXPCGHUTBCPZHN-UHFFFAOYSA-N 3-phenylhexane-2,5-dione Chemical compound CC(=O)CC(C(C)=O)C1=CC=CC=C1 FXPCGHUTBCPZHN-UHFFFAOYSA-N 0.000 description 1
- RZNFTONUJHJTGA-UHFFFAOYSA-N 4-oxo-2-phenylpentanal Chemical compound CC(=O)CC(C=O)C1=CC=CC=C1 RZNFTONUJHJTGA-UHFFFAOYSA-N 0.000 description 1
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- SVUJRGIZGQQCQY-UHFFFAOYSA-N 5-oxo-2-phenylhexanal Chemical compound CC(=O)CCC(C=O)C1=CC=CC=C1 SVUJRGIZGQQCQY-UHFFFAOYSA-N 0.000 description 1
- HSWQVWXDSDEBSP-UHFFFAOYSA-N 5-oxo-6-phenylhexanal Chemical compound O=CCCCC(=O)CC1=CC=CC=C1 HSWQVWXDSDEBSP-UHFFFAOYSA-N 0.000 description 1
- DGCBTMCXHXNPHH-UHFFFAOYSA-N 5-oxoheptanal Chemical compound CCC(=O)CCCC=O DGCBTMCXHXNPHH-UHFFFAOYSA-N 0.000 description 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
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- HGRGPAAXHOTBAM-UHFFFAOYSA-N Heptan-2,5-dione Chemical compound CCC(=O)CCC(C)=O HGRGPAAXHOTBAM-UHFFFAOYSA-N 0.000 description 1
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- 238000011088 calibration curve Methods 0.000 description 1
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
【解決手段】α,β−不飽和カルボニル化合物の製造方法であって、亜臨界または超臨界状態の水を反応溶媒とし、α位に少なくとも1つの水素原子を有するカルボニル化合物のアルドール縮合反応によりα,β−不飽和カルボニル化合物を生成させる。
【選択図】なし
Description
SUS316製回分式反応器(長さ105.7mm、内径12.7mm、厚さ2.1mm、内容積6cm3)に、2,5−ヘキサンジオン、超純水を表1に記載の量を仕込み、アルゴンガス(圧力:大気圧)により系内を置換した。反応は、あらかじめ反応温度に設定した流動砂浴内に回分式反応器を投入することにより開始させた。ここでは、流動砂浴の温度を反応温度とした。続いて、所定の反応時間経過後、流動砂浴から取り出した回分式反応器を、14℃の冷水浴に投入することにより、反応を停止させた。生成物は高速液体クロマトグラフィにより以下の条件で定性、定量を行った。
カラム:Shodex製 KS−811
カラム温度:80℃
HPLCポンプ:日本分光製 MODEL PU−1580
溶媒:10重量%リン酸水溶液
流量:1cm3/min
検出器:RI検出器 ERMA株式会社製 ERC−7512
UV検出器 Shodex製 UV−41型
UV検出波長:210nm
水密度の影響を調べるために、超純水の仕込み量を1.2gとした以外は、実施例3と同様にして反応を行った。
Claims (9)
- α,β−不飽和カルボニル化合物の製造方法であって、
亜臨界または超臨界状態の水を反応溶媒とし、α位に少なくとも1つの水素原子を有するカルボニル化合物のアルドール縮合反応によりα,β−不飽和カルボニル化合物を生成させることを特徴とするα,β−不飽和カルボニル化合物の製造方法。 - 請求項1に記載のα,β−不飽和カルボニル化合物の製造方法であって、
前記カルボニル化合物は、カルボニル基を分子内に少なくとも2つ有することを特徴とするα,β−不飽和カルボニル化合物の製造方法。 - 請求項1または2に記載のα,β−不飽和カルボニル化合物の製造方法であって、
前記α,β−不飽和カルボニル化合物は、2−シクロアルケン−1−オン類であることを特徴とするα,β−不飽和カルボニル化合物の製造方法。 - 請求項1〜3のいずれか1つに記載のα,β−不飽和カルボニル化合物の製造方法であって、
前記カルボニル化合物は、カルボニル基を分子内に少なくとも2つ有し、前記2つのカルボニル基の間の炭素数が2または3であることを特徴とするα,β−不飽和カルボニル化合物の製造方法。 - 請求項1〜4のいずれか1つに記載のα,β−不飽和カルボニル化合物の製造方法であって、
前記カルボニル化合物は、2,5−ヘキサンジオンであり、
前記α,β−不飽和カルボニル化合物は、3−メチル−2−シクロペンテノンであることを特徴とするα,β−不飽和カルボニル化合物の製造方法。 - 請求項1〜5のいずれか1つに記載のα,β−不飽和カルボニル化合物の製造方法であって、
前記反応時の温度は、250℃〜600℃の範囲であることを特徴とするα,β−不飽和カルボニル化合物の製造方法。 - 請求項1〜6のいずれか1つに記載のα,β−不飽和カルボニル化合物の製造方法であって、
前記反応時の圧力は、5MPa〜300MPaの範囲であることを特徴とするα,β−不飽和カルボニル化合物の製造方法。 - 請求項1〜7のいずれか1つに記載のα,β−不飽和カルボニル化合物の製造方法であって、
前記反応時の前記水の密度は、0.1g/cm3〜0.8g/cm3の範囲であることを特徴とするα,β−不飽和カルボニル化合物の製造方法。 - 請求項1〜8のいずれか1つに記載のα,β−不飽和カルボニル化合物の製造方法により製造されることを特徴とするα,β−不飽和カルボニル化合物。
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JP2009143903A (ja) * | 2007-11-22 | 2009-07-02 | Univ Nihon | ポリアセン類の合成方法 |
JP2010202620A (ja) * | 2009-03-06 | 2010-09-16 | Nihon Univ | 1,3,5−トリベンゾイルベンゼンの製造方法 |
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JP2009143903A (ja) * | 2007-11-22 | 2009-07-02 | Univ Nihon | ポリアセン類の合成方法 |
JP2010202620A (ja) * | 2009-03-06 | 2010-09-16 | Nihon Univ | 1,3,5−トリベンゾイルベンゼンの製造方法 |
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