CA2280592A1 - Dicarboxylic acid crystallizates - Google Patents
Dicarboxylic acid crystallizates Download PDFInfo
- Publication number
- CA2280592A1 CA2280592A1 CA002280592A CA2280592A CA2280592A1 CA 2280592 A1 CA2280592 A1 CA 2280592A1 CA 002280592 A CA002280592 A CA 002280592A CA 2280592 A CA2280592 A CA 2280592A CA 2280592 A1 CA2280592 A1 CA 2280592A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- dicarboxylic acid
- crystals
- anionic polyelectrolyte
- anionic
- 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.)
- Abandoned
Links
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 38
- 229920001448 anionic polyelectrolyte Polymers 0.000 claims abstract description 36
- 238000002425 crystallisation Methods 0.000 claims abstract description 32
- 230000008025 crystallization Effects 0.000 claims abstract description 32
- 239000002253 acid Substances 0.000 claims abstract description 11
- 239000013078 crystal Substances 0.000 claims description 66
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 44
- 230000008569 process Effects 0.000 claims description 27
- 235000011037 adipic acid Nutrition 0.000 claims description 23
- 239000001361 adipic acid Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 15
- 239000000178 monomer Substances 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 229920002125 Sokalan® Polymers 0.000 claims description 3
- 239000004584 polyacrylic acid Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002015 acyclic group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000000243 solution Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 125000000129 anionic group Chemical group 0.000 description 15
- 229920000867 polyelectrolyte Polymers 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 10
- 150000001991 dicarboxylic acids Chemical class 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 239000000470 constituent Substances 0.000 description 4
- 238000011109 contamination Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- -1 quaternary ammonium ions Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000011549 crystallization solution Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/50—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19705329A DE19705329A1 (de) | 1997-02-12 | 1997-02-12 | Dicarbonsäurekristallisate |
| DE19705329.7 | 1997-02-12 | ||
| PCT/EP1998/000703 WO1998035929A1 (de) | 1997-02-12 | 1998-02-09 | Dicarbonsäurekristallisate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2280592A1 true CA2280592A1 (en) | 1998-08-20 |
Family
ID=7820011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002280592A Abandoned CA2280592A1 (en) | 1997-02-12 | 1998-02-09 | Dicarboxylic acid crystallizates |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6534680B1 (https=) |
| EP (1) | EP0968167B1 (https=) |
| JP (1) | JP3984297B2 (https=) |
| KR (1) | KR100509312B1 (https=) |
| CN (1) | CN1093115C (https=) |
| AU (1) | AU6296198A (https=) |
| BR (1) | BR9807326A (https=) |
| CA (1) | CA2280592A1 (https=) |
| DE (2) | DE19705329A1 (https=) |
| PL (1) | PL189983B1 (https=) |
| RU (1) | RU2195442C2 (https=) |
| UA (1) | UA54494C2 (https=) |
| WO (1) | WO1998035929A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW460452B (en) * | 1998-09-14 | 2001-10-21 | Rhodia Fiber & Amp Resin Inter | Process for the crystallization of carboxylic acid and process for manufacturing crystalline carboxylic acid |
| FR2795720B1 (fr) * | 1999-06-29 | 2003-05-02 | Rhone Poulenc Fibres | Procede de cristallisation d'acide carboxylique et procede de fabrication d'acide carboxylique cristallise |
| FR2795721B1 (fr) * | 1999-06-29 | 2003-04-18 | Rhone Poulenc Fibres | Procede de fabrication d'acide adipique |
| EP1198444A1 (en) * | 1999-07-23 | 2002-04-24 | Chemintel (India) Private Limited | Process for crystallization of dicarboxylic acids |
| DE10043610A1 (de) * | 2000-09-05 | 2002-03-14 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| JP2006321996A (ja) * | 2005-04-22 | 2006-11-30 | Mitsubishi Chemicals Corp | ポリエステルの製造方法 |
| US20120021473A1 (en) * | 2010-04-01 | 2012-01-26 | Bioamber S.A.S. | Processes for producing carboxylic acids from fermentation broths containing their ammonium salts |
| WO2014140276A1 (de) | 2013-03-15 | 2014-09-18 | Basf Se | Verfahren zur herstellung von rieselfähigen dicarbonsäure-kristallisaten |
| WO2016016375A1 (de) * | 2014-07-30 | 2016-02-04 | Basf Se | Verfahren zur herstellung von rieselfähigen und lagerstabilen dicarbonsäure-kristallen |
| FR3028864B1 (fr) * | 2014-11-26 | 2018-05-18 | Roquette Freres | Procede de recuperation de cristaux d'acide succinique avec mise en œuvre de tensioactifs au cours de la cristallisation, cristaux obtenus et leurs utilisations |
| JP7458147B2 (ja) | 2016-01-13 | 2024-03-29 | ストラ エンソ オーユーイー | ２，５－フランジカルボン酸ならびにその中間体および誘導体の製造方法 |
| JP6944746B2 (ja) * | 2016-09-09 | 2021-10-06 | 花王株式会社 | ジカルボン酸結晶及びその製造方法 |
| KR102341902B1 (ko) | 2016-09-09 | 2021-12-21 | 카오카부시키가이샤 | 디카르복실산 결정 및 그 제조 방법 |
| JP7053220B2 (ja) | 2017-06-15 | 2022-04-12 | 花王株式会社 | ジカルボン酸結晶の製造方法 |
| WO2018230011A1 (ja) * | 2017-06-15 | 2018-12-20 | 花王株式会社 | ジカルボン酸結晶の製造方法 |
| WO2019014393A1 (en) | 2017-07-12 | 2019-01-17 | Stora Enso Oyj | NOVEL PROCESSES FOR PREPARING 2,5-FURANDICARBOXYLIC ACID |
| CA3069521A1 (en) | 2017-07-12 | 2019-01-17 | Stora Enso Oyj | Purified 2,5-furandicarboxylic acid pathway products |
| JP7081946B2 (ja) * | 2018-03-13 | 2022-06-07 | 花王株式会社 | フマル酸結晶の製造方法 |
| CN113979860B (zh) * | 2021-11-11 | 2022-11-29 | 天津大学 | 一种2，4-二氯苯氧乙酸晶体及其制备方法和应用 |
| JP2023084097A (ja) * | 2021-12-06 | 2023-06-16 | 花王株式会社 | 芳香族ヒドロキシカルボン酸結晶の製造方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL273696A (https=) * | 1961-01-18 | |||
| US3330665A (en) * | 1964-03-17 | 1967-07-11 | Monsanto Co | Cold water soluble acid compositions |
| GB1143800A (https=) * | 1966-06-23 | |||
| US3770390A (en) * | 1971-02-26 | 1973-11-06 | Dow Chemical Co | Crystal habit modification of inorganic salts using polymeric sulfonates or sulfates |
| GB1373167A (en) | 1972-01-26 | 1974-11-06 | Ici Ltd | Manufacture of dyestuff powder |
| BE794539A (fr) * | 1972-01-26 | 1973-07-25 | Ici Ltd | Persels |
| US4254283A (en) * | 1979-06-07 | 1981-03-03 | Monsanto Company | Process for preparing adipic acid with recovery of glutaric and succinic acids |
| JPS60169436A (ja) * | 1984-02-14 | 1985-09-02 | Nippon Shokubai Kagaku Kogyo Co Ltd | 速溶性フマ−ル酸組成物 |
| DE3434918A1 (de) * | 1984-09-22 | 1986-04-03 | Hüls AG, 4370 Marl | Verfahren zur gewinnung von l-aepfelsaeure |
| US5149867A (en) * | 1987-07-28 | 1992-09-22 | Hatco Corporation | Crystallization of water-insoluble dicarboxylic acid |
| US5034105A (en) * | 1989-07-27 | 1991-07-23 | Michigan Biotechnology Institute | Carboxylic acid purification and crystallization process |
| US5104492A (en) * | 1990-07-11 | 1992-04-14 | The Regents Of The University Of California | Recovery of carboxylic acids from water by precipitation from organic solutions |
| US5296639A (en) * | 1992-12-18 | 1994-03-22 | E. I. Du Pont De Nemours And Company | Adipic acid purification |
-
1997
- 1997-02-12 DE DE19705329A patent/DE19705329A1/de not_active Withdrawn
-
1998
- 1998-02-09 JP JP53531798A patent/JP3984297B2/ja not_active Expired - Fee Related
- 1998-02-09 EP EP98906938A patent/EP0968167B1/de not_active Expired - Lifetime
- 1998-02-09 WO PCT/EP1998/000703 patent/WO1998035929A1/de not_active Ceased
- 1998-02-09 BR BR9807326-5A patent/BR9807326A/pt not_active Application Discontinuation
- 1998-02-09 US US09/367,233 patent/US6534680B1/en not_active Expired - Lifetime
- 1998-02-09 CN CN98804115A patent/CN1093115C/zh not_active Expired - Fee Related
- 1998-02-09 RU RU99119595/04A patent/RU2195442C2/ru not_active IP Right Cessation
- 1998-02-09 CA CA002280592A patent/CA2280592A1/en not_active Abandoned
- 1998-02-09 KR KR10-1999-7007230A patent/KR100509312B1/ko not_active Expired - Fee Related
- 1998-02-09 AU AU62961/98A patent/AU6296198A/en not_active Abandoned
- 1998-02-09 DE DE59805697T patent/DE59805697D1/de not_active Expired - Lifetime
- 1998-02-09 PL PL98335023A patent/PL189983B1/pl not_active IP Right Cessation
- 1998-09-02 UA UA99095051A patent/UA54494C2/uk unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE59805697D1 (de) | 2002-10-31 |
| AU6296198A (en) | 1998-09-08 |
| KR100509312B1 (ko) | 2005-08-22 |
| CN1093115C (zh) | 2002-10-23 |
| CN1252048A (zh) | 2000-05-03 |
| WO1998035929A1 (de) | 1998-08-20 |
| JP2001511791A (ja) | 2001-08-14 |
| EP0968167B1 (de) | 2002-09-25 |
| EP0968167A1 (de) | 2000-01-05 |
| JP3984297B2 (ja) | 2007-10-03 |
| BR9807326A (pt) | 2000-04-18 |
| UA54494C2 (uk) | 2003-03-17 |
| DE19705329A1 (de) | 1998-08-13 |
| PL189983B1 (pl) | 2005-10-31 |
| US6534680B1 (en) | 2003-03-18 |
| KR20000070964A (ko) | 2000-11-25 |
| PL335023A1 (en) | 2000-03-27 |
| RU2195442C2 (ru) | 2002-12-27 |
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