JPS6047693A - グルコノデルタラクトンの製法 - Google Patents

グルコノデルタラクトンの製法

Info

Publication number: JPS6047693A
Authority: JP; Japan
Prior art keywords: lactone; glucose; reaction; organic solvent; delta
Prior art date: 1983-08-24
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

Application number

JP15306383A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0433438B2 (de

Inventor

Nobumi Kunishige

国重　悦己

Kimitoshi Kawai

河合　公利

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Daicel Corp

Original Assignee

Daicel Chemical Industries Ltd

Priority date (The priority date 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 date listed.)

1983-08-24

Filing date

1983-08-24

Publication date

1985-03-15

1983-08-24 Application filed by Daicel Chemical Industries Ltd filed Critical Daicel Chemical Industries Ltd

1983-08-24 Priority to JP15306383A priority Critical patent/JPS6047693A/ja

1985-03-15 Publication of JPS6047693A publication Critical patent/JPS6047693A/ja

1992-06-03 Publication of JPH0433438B2 publication Critical patent/JPH0433438B2/ja

Status Granted legal-status Critical Current

Links

PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 title claims abstract description 43
235000012209 glucono delta-lactone Nutrition 0.000 title claims abstract description 43
239000000182 glucono-delta-lactone Substances 0.000 title claims abstract description 43
229960003681 gluconolactone Drugs 0.000 title claims abstract description 43
238000004519 manufacturing process Methods 0.000 title claims description 16
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 28
239000008103 glucose Substances 0.000 claims abstract description 28
239000003960 organic solvent Substances 0.000 claims abstract description 28
239000004366 Glucose oxidase Substances 0.000 claims abstract description 18
108010015776 Glucose oxidase Proteins 0.000 claims abstract description 18
229940116332 glucose oxidase Drugs 0.000 claims abstract description 18
235000019420 glucose oxidase Nutrition 0.000 claims abstract description 18
230000007935 neutral effect Effects 0.000 claims abstract description 4
238000007254 oxidation reaction Methods 0.000 claims abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 19
238000006911 enzymatic reaction Methods 0.000 abstract description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 12
239000001301 oxygen Substances 0.000 abstract description 12
229910052760 oxygen Inorganic materials 0.000 abstract description 12
239000007789 gas Substances 0.000 abstract description 9
102000016938 Catalase Human genes 0.000 abstract description 7
108010053835 Catalase Proteins 0.000 abstract description 7
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract description 4
239000003054 catalyst Substances 0.000 abstract description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
238000006243 chemical reaction Methods 0.000 description 47
239000000243 solution Substances 0.000 description 28
102000004190 Enzymes Human genes 0.000 description 21
108090000790 Enzymes Proteins 0.000 description 21
229940088598 enzyme Drugs 0.000 description 21
RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 17
239000000174 gluconic acid Substances 0.000 description 17
235000012208 gluconic acid Nutrition 0.000 description 17
238000000034 method Methods 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000007864 aqueous solution Substances 0.000 description 13
230000000694 effects Effects 0.000 description 10
239000002904 solvent Substances 0.000 description 10
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
150000002596 lactones Chemical class 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
230000001580 bacterial effect Effects 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
238000007273 lactonization reaction Methods 0.000 description 4
238000000926 separation method Methods 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000003513 alkali Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
230000009849 deactivation Effects 0.000 description 3
238000000855 fermentation Methods 0.000 description 3
230000004151 fermentation Effects 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
241000228245 Aspergillus niger Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
230000007423 decrease Effects 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
150000005846 sugar alcohols Polymers 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
241000228212 Aspergillus Species 0.000 description 1
241000233866 Fungi Species 0.000 description 1
108010093096 Immobilized Enzymes Proteins 0.000 description 1
241000228143 Penicillium Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000005273 aeration Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
235000013527 bean curd Nutrition 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000000701 coagulant Substances 0.000 description 1
238000010276 construction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000003599 detergent Substances 0.000 description 1
229910001882 dioxygen Inorganic materials 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000013373 food additive Nutrition 0.000 description 1
239000002778 food additive Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
-1 gluconate alkali salt Chemical class 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000012528 membrane Substances 0.000 description 1
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
UNYNVICDCJHOPO-UHFFFAOYSA-N quabalactone III Natural products CC1OC(=O)C(O)=C1C UNYNVICDCJHOPO-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)

JP15306383A 1983-08-24 1983-08-24 グルコノデルタラクトンの製法 Granted JPS6047693A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP15306383A JPS6047693A (ja)	1983-08-24	1983-08-24	グルコノデルタラクトンの製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP15306383A JPS6047693A (ja)	1983-08-24	1983-08-24	グルコノデルタラクトンの製法

Publications (2)

Publication Number	Publication Date
JPS6047693A true JPS6047693A (ja)	1985-03-15
JPH0433438B2 JPH0433438B2 (de)	1992-06-03

Family

ID=15554169

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP15306383A Granted JPS6047693A (ja)	1983-08-24	1983-08-24	グルコノデルタラクトンの製法

Country Status (1)

Country	Link
JP (1)	JPS6047693A (de)

1983
- 1983-08-24 JP JP15306383A patent/JPS6047693A/ja active Granted

Also Published As

Publication number	Publication date
JPH0433438B2 (de)	1992-06-03

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