JP2006083110A - ラクトン誘導体及びその製造方法 - Google Patents
ラクトン誘導体及びその製造方法 Download PDFInfo
- Publication number
- JP2006083110A JP2006083110A JP2004270577A JP2004270577A JP2006083110A JP 2006083110 A JP2006083110 A JP 2006083110A JP 2004270577 A JP2004270577 A JP 2004270577A JP 2004270577 A JP2004270577 A JP 2004270577A JP 2006083110 A JP2006083110 A JP 2006083110A
- Authority
- JP
- Japan
- Prior art keywords
- deoxy
- lactone derivative
- aldohexose
- sulfuric acid
- producing
- 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.)
- Granted
Links
- 150000002596 lactones Chemical class 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000007858 starting material Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002994 raw material Substances 0.000 description 8
- 239000002028 Biomass Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000002803 fossil fuel Substances 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- -1 2-deoxy-L-mannose Chemical compound 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 238000007865 diluting Methods 0.000 description 4
- 150000002402 hexoses Chemical group 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000003513 alkali Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VRYALKFFQXWPIH-PBXRRBTRSA-N (3r,4s,5r)-3,4,5,6-tetrahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)CC=O VRYALKFFQXWPIH-PBXRRBTRSA-N 0.000 description 2
- VRYALKFFQXWPIH-JKUQZMGJSA-N (3s,4s,5r)-3,4,5,6-tetrahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CC=O VRYALKFFQXWPIH-JKUQZMGJSA-N 0.000 description 2
- VRYALKFFQXWPIH-HSUXUTPPSA-N 2-deoxy-D-galactose Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)CC=O VRYALKFFQXWPIH-HSUXUTPPSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002401 hexose derivatives Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- VRYALKFFQXWPIH-RANCGNPWSA-N (3r,4s,5r)-3,4,5,6-tetrahydroxy-2-tritiohexanal Chemical compound O=CC([3H])[C@@H](O)[C@H](O)[C@H](O)CO VRYALKFFQXWPIH-RANCGNPWSA-N 0.000 description 1
- VRYALKFFQXWPIH-KVQBGUIXSA-N (3s,4r,5r)-3,4,5,6-tetrahydroxyhexanal Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)CC=O VRYALKFFQXWPIH-KVQBGUIXSA-N 0.000 description 1
- VRYALKFFQXWPIH-HCWXCVPCSA-N (3s,4r,5s)-3,4,5,6-tetrahydroxyhexanal Chemical compound OC[C@H](O)[C@H](O)[C@@H](O)CC=O VRYALKFFQXWPIH-HCWXCVPCSA-N 0.000 description 1
- GZCGUPFRVQAUEE-UHFFFAOYSA-N 2,3,4,5,6-pentahydroxyhexanal Chemical compound OCC(O)C(O)C(O)C(O)C=O GZCGUPFRVQAUEE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 1
- CPFWDKHAGLQDFF-UHFFFAOYSA-N OCCC(O1)=CCC1=O Chemical compound OCCC(O1)=CCC1=O CPFWDKHAGLQDFF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- PMMURAAUARKVCB-UHFFFAOYSA-N alpha-D-ara-dHexp Natural products OCC1OC(O)CC(O)C1O PMMURAAUARKVCB-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000422 delta-lactone group Chemical group 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 150000002243 furanoses Chemical group 0.000 description 1
- 125000000457 gamma-lactone group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003214 pyranose derivatives Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/58—One oxygen atom, e.g. butenolide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
Abstract
Description
2−デオキシ−D−グルコース0.164部を、ガラス製反応容器中の31.7%の硫酸3.51部中に添加し、20℃で1時間撹拌した。イオン交換水10部で希釈した後、炭酸カルシウムを添加して、中和した。遠心分離機により、中和により生成した硫酸カルシウムと水溶液とを分離した。水溶液をエバポレータにより濃縮して前記構造式(I)で示される目的物0.142部を得た(収率75.6%)。
溶媒に使用する硫酸を、47.5%の硫酸3.83部とした以外は、実施例1と同様にして反応を行った。前記構造式(I)で示される目的物0.0269部を得た(収率14.3%)。
溶媒に使用する硫酸を、63.3%の硫酸4.22部とした以外は、実施例1と同様にして反応を行った。前記構造式(I)で示される目的物0.0015部を得た(収率0.8%)。
Claims (4)
- 請求項1に記載のラクトン誘導体であって、
前記ラクトン誘導体は、2−デオキシ−アルドヘキソースを出発原料として製造されることを特徴とするラクトン誘導体。 - 請求項1または2に記載のラクトン誘導体であって、
前記ラクトン誘導体は、2−デオキシ−アルドヘキソースを硫酸中で反応させることにより製造されることを特徴とするラクトン誘導体。
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004270577A JP4624045B2 (ja) | 2004-09-16 | 2004-09-16 | ラクトン誘導体の製造方法 |
US11/225,175 US7511160B2 (en) | 2004-09-16 | 2005-09-14 | Lactone derivative and its manufacturing method |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004270577A JP4624045B2 (ja) | 2004-09-16 | 2004-09-16 | ラクトン誘導体の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2006083110A true JP2006083110A (ja) | 2006-03-30 |
JP4624045B2 JP4624045B2 (ja) | 2011-02-02 |
Family
ID=36034981
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2004270577A Expired - Fee Related JP4624045B2 (ja) | 2004-09-16 | 2004-09-16 | ラクトン誘導体の製造方法 |
Country Status (2)
Country | Link |
---|---|
US (1) | US7511160B2 (ja) |
JP (1) | JP4624045B2 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014073987A (ja) * | 2012-10-04 | 2014-04-24 | Fromseeds Corp | シクロペンテノン誘導体の製造方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000035835A1 (fr) * | 1998-12-11 | 2000-06-22 | Daicel Chemical Industries, Ltd. | Procede de preparation de composes organiques au moyen de catalyseurs imide |
US6713639B1 (en) * | 2002-10-28 | 2004-03-30 | Council Of Scientific And Industrial Research | Process for preparing enantiomerically pure (S)-3-hydroxy-gamma-butyrolactone |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8519384D0 (en) | 1985-08-01 | 1985-09-04 | Lucas Ind Plc | Position encoder |
JP3872135B2 (ja) | 1996-05-23 | 2007-01-24 | 第一ファインケミカル株式会社 | 光学活性なγ−ブチロラクトン誘導体の製造法 |
JP2003250592A (ja) | 2002-03-01 | 2003-09-09 | Kanegafuchi Chem Ind Co Ltd | 光学活性4−フェニル−4−ヒドロキシ酪酸誘導体の製造法 |
-
2004
- 2004-09-16 JP JP2004270577A patent/JP4624045B2/ja not_active Expired - Fee Related
-
2005
- 2005-09-14 US US11/225,175 patent/US7511160B2/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000035835A1 (fr) * | 1998-12-11 | 2000-06-22 | Daicel Chemical Industries, Ltd. | Procede de preparation de composes organiques au moyen de catalyseurs imide |
US6713639B1 (en) * | 2002-10-28 | 2004-03-30 | Council Of Scientific And Industrial Research | Process for preparing enantiomerically pure (S)-3-hydroxy-gamma-butyrolactone |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014073987A (ja) * | 2012-10-04 | 2014-04-24 | Fromseeds Corp | シクロペンテノン誘導体の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
US20060058536A1 (en) | 2006-03-16 |
US7511160B2 (en) | 2009-03-31 |
JP4624045B2 (ja) | 2011-02-02 |
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