JPH0312049B2 - - Google Patents

Info

Publication number: JPH0312049B2
Authority: JP; Japan
Prior art keywords: cis; muconic acid; acid; resin; ion exchange
Prior art date: 1988-11-29
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.): Expired

Application number

JP29958788A

Other languages

English (en)

Japanese (ja)

Other versions

JPH02145537A (ja

Inventor

Nobuji Yoshikawa

Kunihiko Oota

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.)

National Institute of Advanced Industrial Science and Technology AIST

Original Assignee

Agency of Industrial Science and Technology

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.)

1988-11-29

Filing date

1988-11-29

Publication date

1991-02-19

1988-11-29 Application filed by Agency of Industrial Science and Technology filed Critical Agency of Industrial Science and Technology

1988-11-29 Priority to JP29958788A priority Critical patent/JPH02145537A/ja

1990-06-05 Publication of JPH02145537A publication Critical patent/JPH02145537A/ja

1991-02-19 Publication of JPH0312049B2 publication Critical patent/JPH0312049B2/ja

Status Granted legal-status Critical Current

Links

TXXHDPDFNKHHGW-CCAGOZQPSA-N cis,cis-muconic acid Chemical compound OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 73
TXXHDPDFNKHHGW-UHFFFAOYSA-N (2E,4E)-2,4-hexadienedioic acid Natural products OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 41
239000011347 resin Substances 0.000 description 28
229920005989 resin Polymers 0.000 description 28
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 17
238000000034 method Methods 0.000 description 14
239000003456 ion exchange resin Substances 0.000 description 13
229920003303 ion-exchange polymer Polymers 0.000 description 13
239000005711 Benzoic acid Substances 0.000 description 12
235000010233 benzoic acid Nutrition 0.000 description 12
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000001179 sorption measurement Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000002994 raw material Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
229920001429 chelating resin Polymers 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
230000001580 bacterial effect Effects 0.000 description 4
239000012535 impurity Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000001888 Peptone Substances 0.000 description 3
108010080698 Peptones Proteins 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
229940041514 candida albicans extract Drugs 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000010828 elution Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
235000019319 peptone Nutrition 0.000 description 3
239000012138 yeast extract Substances 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000723353 Chrysanthemum Species 0.000 description 2
235000007516 Chrysanthemum Nutrition 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
239000012670 alkaline solution Substances 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical class C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
241000186063 Arthrobacter Species 0.000 description 1
241000186073 Arthrobacter sp. Species 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
241000186226 Corynebacterium glutamicum Species 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
241000589776 Pseudomonas putida Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
238000003916 acid precipitation Methods 0.000 description 1
238000005273 aeration Methods 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
TXXHDPDFNKHHGW-HSFFGMMNSA-N cis,trans-muconic acid Chemical compound OC(=O)\C=C\C=C/C(O)=O TXXHDPDFNKHHGW-HSFFGMMNSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
239000008213 purified water Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000004448 titration Methods 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
-1 well Chemical compound 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

JP29958788A 1988-11-29 1988-11-29 シス，シス−ムコン酸の精製法 Granted JPH02145537A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP29958788A JPH02145537A (ja)	1988-11-29	1988-11-29	シス，シス−ムコン酸の精製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP29958788A JPH02145537A (ja)	1988-11-29	1988-11-29	シス，シス−ムコン酸の精製法

Publications (2)

Publication Number	Publication Date
JPH02145537A JPH02145537A (ja)	1990-06-05
JPH0312049B2 true JPH0312049B2 (fr)	1991-02-19

Family

ID=17874563

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP29958788A Granted JPH02145537A (ja)	1988-11-29	1988-11-29	シス，シス−ムコン酸の精製法

Country Status (1)

Country	Link
JP (1)	JPH02145537A (fr)

1988
- 1988-11-29 JP JP29958788A patent/JPH02145537A/ja active Granted

Also Published As

Publication number	Publication date
JPH02145537A (ja)	1990-06-05

Legal Events

Date	Code	Title	Description
2008-11-29	EXPY	Cancellation because of completion of term

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