JP4297608B2 - フタリドの精製 - Google Patents
フタリドの精製 Download PDFInfo
- Publication number
- JP4297608B2 JP4297608B2 JP2000512822A JP2000512822A JP4297608B2 JP 4297608 B2 JP4297608 B2 JP 4297608B2 JP 2000512822 A JP2000512822 A JP 2000512822A JP 2000512822 A JP2000512822 A JP 2000512822A JP 4297608 B2 JP4297608 B2 JP 4297608B2
- Authority
- JP
- Japan
- Prior art keywords
- phthalide
- recovery method
- crystallization
- reaction mixture
- washing
- 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.)
- Expired - Fee Related
Links
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 title claims description 119
- 238000000746 purification Methods 0.000 title description 6
- 239000013078 crystal Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- 238000002425 crystallisation Methods 0.000 claims description 26
- 230000008025 crystallization Effects 0.000 claims description 24
- 239000011541 reaction mixture Substances 0.000 claims description 20
- 238000001816 cooling Methods 0.000 claims description 18
- 238000005406 washing Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 12
- 239000000725 suspension Substances 0.000 claims description 12
- 238000011084 recovery Methods 0.000 claims description 11
- 238000002386 leaching Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 150000003021 phthalic acid derivatives Chemical class 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 6
- 238000001640 fractional crystallisation Methods 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 claims description 3
- 238000009905 homogeneous catalytic hydrogenation reaction Methods 0.000 claims description 3
- 239000000047 product Substances 0.000 description 18
- 239000003792 electrolyte Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 125000005506 phthalide group Chemical group 0.000 description 12
- 239000012452 mother liquor Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical group OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- -1 ammonium halide Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 0 *c1c(*)c(*)c(*)c(*)c1* Chemical compound *c1c(*)c(*)c(*)c(*)c1* 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- QCWXDVFBZVHKLV-UHFFFAOYSA-N 1-tert-butyl-4-methylbenzene Chemical compound CC1=CC=C(C(C)(C)C)C=C1 QCWXDVFBZVHKLV-UHFFFAOYSA-N 0.000 description 1
- OZCUCQLHGQMOAV-UHFFFAOYSA-N 2-(2-azaniumylethyl)benzoate Chemical compound NCCC1=CC=CC=C1C(O)=O OZCUCQLHGQMOAV-UHFFFAOYSA-N 0.000 description 1
- MGMNPSAERQZUIM-UHFFFAOYSA-N 2-(hydroxymethyl)benzoic acid Chemical compound OCC1=CC=CC=C1C(O)=O MGMNPSAERQZUIM-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- SARKQAUWTBDBIZ-UHFFFAOYSA-N azane;2-carbamoylbenzoic acid Chemical compound [NH4+].NC(=O)C1=CC=CC=C1C([O-])=O SARKQAUWTBDBIZ-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002848 electrochemical method Methods 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000006056 electrooxidation reaction Methods 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000005172 methylbenzenes Chemical class 0.000 description 1
- SDLAKRCBYGZJRW-UHFFFAOYSA-N n-tert-butylformamide Chemical compound CC(C)(C)NC=O SDLAKRCBYGZJRW-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 238000004094 preconcentration Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- HJHUXWBTVVFLQI-UHFFFAOYSA-N tributyl(methyl)azanium Chemical compound CCCC[N+](C)(CCCC)CCCC HJHUXWBTVVFLQI-UHFFFAOYSA-N 0.000 description 1
- SEACXNRNJAXIBM-UHFFFAOYSA-N triethyl(methyl)azanium Chemical compound CC[N+](C)(CC)CC SEACXNRNJAXIBM-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/25—Reduction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19741423A DE19741423A1 (de) | 1997-09-19 | 1997-09-19 | Verfahren zur Herstellung von Phthaliden |
| DE19741423.0 | 1997-09-19 | ||
| DE1997145579 DE19745579A1 (de) | 1997-10-15 | 1997-10-15 | Verfahren zur Reinigung von Phthaliden |
| DE19745579.4 | 1997-10-15 | ||
| PCT/EP1998/005983 WO1999015515A1 (de) | 1997-09-19 | 1998-09-18 | Verfahren zur reinigung von phthaliden |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001517663A JP2001517663A (ja) | 2001-10-09 |
| JP2001517663A5 JP2001517663A5 (enExample) | 2006-01-05 |
| JP4297608B2 true JP4297608B2 (ja) | 2009-07-15 |
Family
ID=26040142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000512822A Expired - Fee Related JP4297608B2 (ja) | 1997-09-19 | 1998-09-18 | フタリドの精製 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6362347B1 (enExample) |
| EP (1) | EP1017689B1 (enExample) |
| JP (1) | JP4297608B2 (enExample) |
| KR (1) | KR100549132B1 (enExample) |
| CN (1) | CN1280282C (enExample) |
| AR (1) | AR018507A1 (enExample) |
| BR (1) | BR9812248A (enExample) |
| CA (1) | CA2303876C (enExample) |
| CO (1) | CO5100970A1 (enExample) |
| DE (1) | DE59807489D1 (enExample) |
| ES (1) | ES2194355T3 (enExample) |
| HU (1) | HUP0003490A3 (enExample) |
| IL (1) | IL135046A0 (enExample) |
| WO (1) | WO1999015515A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016146753A1 (en) * | 2015-03-17 | 2016-09-22 | Purac Biochem Bv | Method for manufacturing furan-2,5-dicarboxylic acid (fdca) from a salt solution |
| EP3545120A1 (en) * | 2016-11-24 | 2019-10-02 | Avantium Knowledge Centre B.v. | Process for treating a furan-2,5-dicarboxylic acid composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2510920A1 (de) * | 1975-03-13 | 1976-09-30 | Basf Ag | Verfahren zur elektrochemischen herstellung von phthalid |
| DE19618854A1 (de) * | 1996-05-10 | 1997-11-13 | Basf Ag | Verfahren zur Herstellung von Phthaliden |
-
1998
- 1998-09-17 AR ARP980104620A patent/AR018507A1/es unknown
- 1998-09-18 ES ES98951436T patent/ES2194355T3/es not_active Expired - Lifetime
- 1998-09-18 CN CNB988112590A patent/CN1280282C/zh not_active Expired - Fee Related
- 1998-09-18 CA CA002303876A patent/CA2303876C/en not_active Expired - Fee Related
- 1998-09-18 EP EP98951436A patent/EP1017689B1/de not_active Expired - Lifetime
- 1998-09-18 HU HU0003490A patent/HUP0003490A3/hu unknown
- 1998-09-18 CO CO98054043A patent/CO5100970A1/es unknown
- 1998-09-18 IL IL13504698A patent/IL135046A0/xx unknown
- 1998-09-18 KR KR1020007002906A patent/KR100549132B1/ko not_active Expired - Fee Related
- 1998-09-18 DE DE59807489T patent/DE59807489D1/de not_active Expired - Fee Related
- 1998-09-18 WO PCT/EP1998/005983 patent/WO1999015515A1/de not_active Ceased
- 1998-09-18 JP JP2000512822A patent/JP4297608B2/ja not_active Expired - Fee Related
- 1998-09-18 BR BR9812248-7A patent/BR9812248A/pt not_active IP Right Cessation
- 1998-09-18 US US09/508,619 patent/US6362347B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CO5100970A1 (es) | 2001-11-27 |
| CN1280282C (zh) | 2006-10-18 |
| KR20010024142A (ko) | 2001-03-26 |
| ES2194355T3 (es) | 2003-11-16 |
| HUP0003490A2 (hu) | 2001-02-28 |
| CN1279678A (zh) | 2001-01-10 |
| IL135046A0 (en) | 2001-05-20 |
| AR018507A1 (es) | 2001-11-28 |
| JP2001517663A (ja) | 2001-10-09 |
| CA2303876A1 (en) | 1999-04-01 |
| EP1017689B1 (de) | 2003-03-12 |
| KR100549132B1 (ko) | 2006-02-03 |
| BR9812248A (pt) | 2000-07-18 |
| HUP0003490A3 (en) | 2001-03-28 |
| DE59807489D1 (de) | 2003-04-17 |
| EP1017689A1 (de) | 2000-07-12 |
| WO1999015515A1 (de) | 1999-04-01 |
| US6362347B1 (en) | 2002-03-26 |
| CA2303876C (en) | 2006-07-11 |
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