CA2396300A1 - Improved fermentation process - Google Patents
Improved fermentation process Download PDFInfo
- Publication number
- CA2396300A1 CA2396300A1 CA002396300A CA2396300A CA2396300A1 CA 2396300 A1 CA2396300 A1 CA 2396300A1 CA 002396300 A CA002396300 A CA 002396300A CA 2396300 A CA2396300 A CA 2396300A CA 2396300 A1 CA2396300 A1 CA 2396300A1
- Authority
- CA
- Canada
- Prior art keywords
- dicarboxylic acid
- aqueous suspension
- suspension containing
- fatty
- acid according
- 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
- 238000000855 fermentation Methods 0.000 title claims abstract description 90
- 230000004151 fermentation Effects 0.000 title claims abstract description 90
- 239000007900 aqueous suspension Substances 0.000 claims abstract description 45
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 40
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims abstract description 34
- 239000000463 material Substances 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 32
- 239000000725 suspension Substances 0.000 claims abstract description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 20
- 235000020958 biotin Nutrition 0.000 claims abstract description 17
- 239000011616 biotin Substances 0.000 claims abstract description 17
- 229960002685 biotin Drugs 0.000 claims abstract description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 16
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims abstract description 16
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 15
- 239000010452 phosphate Substances 0.000 claims abstract description 15
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 15
- 229910052751 metal Inorganic materials 0.000 claims abstract description 14
- 239000002184 metal Substances 0.000 claims abstract description 14
- 239000013618 particulate matter Substances 0.000 claims abstract description 11
- 241000894006 Bacteria Species 0.000 claims abstract description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 8
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 8
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 6
- 150000003624 transition metals Chemical class 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 61
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 56
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 45
- 239000000194 fatty acid Substances 0.000 claims description 45
- 229930195729 fatty acid Natural products 0.000 claims description 45
- 239000002245 particle Substances 0.000 claims description 41
- 150000004665 fatty acids Chemical class 0.000 claims description 30
- -1 fatty acid ester Chemical class 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- 125000004492 methyl ester group Chemical group 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 description 50
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- 239000002609 medium Substances 0.000 description 46
- 239000008103 glucose Substances 0.000 description 44
- 230000012010 growth Effects 0.000 description 43
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- 235000010633 broth Nutrition 0.000 description 41
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 31
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 30
- 150000001991 dicarboxylic acids Chemical class 0.000 description 29
- 239000005642 Oleic acid Substances 0.000 description 28
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- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 27
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 27
- 239000002253 acid Substances 0.000 description 25
- 238000007254 oxidation reaction Methods 0.000 description 21
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- 239000002028 Biomass Substances 0.000 description 16
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 13
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
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- 239000000908 ammonium hydroxide Substances 0.000 description 9
- 230000003698 anagen phase Effects 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
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- 239000002054 inoculum Substances 0.000 description 8
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- 108090001060 Lipase Proteins 0.000 description 7
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 7
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 7
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 235000011130 ammonium sulphate Nutrition 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
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- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical class CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6409—Fatty acids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/14—Fungi; Culture media therefor
- C12N1/16—Yeasts; Culture media therefor
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Mycology (AREA)
- Botany (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Processing Of Solid Wastes (AREA)
- Treatment Of Sludge (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17517400P | 2000-01-07 | 2000-01-07 | |
| US60/175,174 | 2000-01-07 | ||
| US66396300A | 2000-09-19 | 2000-09-19 | |
| US09/663,963 | 2000-09-19 | ||
| US09/754,158 | 2001-01-04 | ||
| US09/754,158 US6569670B2 (en) | 1999-09-30 | 2001-01-04 | Fermentation process |
| PCT/US2001/000471 WO2001051605A1 (en) | 2000-01-07 | 2001-01-05 | Improved fermentation process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2396300A1 true CA2396300A1 (en) | 2001-07-19 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002396300A Abandoned CA2396300A1 (en) | 2000-01-07 | 2001-01-05 | Improved fermentation process |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6569670B2 (enExample) |
| EP (1) | EP1244771B1 (enExample) |
| JP (1) | JP4666867B2 (enExample) |
| CN (1) | CN1394232A (enExample) |
| AT (1) | ATE387489T1 (enExample) |
| AU (1) | AU2768601A (enExample) |
| CA (1) | CA2396300A1 (enExample) |
| DK (1) | DK1244771T3 (enExample) |
| ES (1) | ES2300315T3 (enExample) |
| WO (1) | WO2001051605A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020061566A1 (en) * | 2000-03-20 | 2002-05-23 | Eirich L. Dudley | Biooxidation capabilities of candida sp |
| US7270947B2 (en) * | 2003-01-14 | 2007-09-18 | Cognis Corporation | Method for controlling biooxidation reactions |
| US7381559B2 (en) * | 2004-06-09 | 2008-06-03 | Scientific Plastic Products, Inc. | Fermentation flask for cultivating microorganisms |
| US7785848B2 (en) * | 2006-05-23 | 2010-08-31 | Activa Biogreen, Inc. | Biomass conversion performance using igneous phyllosilicate minerals with high emission of far-infrared light |
| US20080103340A1 (en) * | 2006-10-27 | 2008-05-01 | Archer-Daniels-Midland Company | Applications of biobased glycol compositions |
| FR2921364B1 (fr) * | 2007-09-20 | 2009-11-06 | Arkema France | Procede de coproduction de 7-oxoheptanoate de methyle et d'acide undecylenique a partir d'acide ricinoleique |
| FR2921362B1 (fr) * | 2007-09-20 | 2012-09-21 | Arkema France | Procede de synthese d'acides gras omega-insatures |
| FR2921363B1 (fr) * | 2007-09-20 | 2009-11-06 | Arkema France | Procedes de synthese de diacides gras par metathese de diacides insatures obtenus par fermentation d'acides gras naturels |
| ATE550944T1 (de) * | 2007-10-23 | 2012-04-15 | Indian Inst Scient | Pilzstämme und ein verfahren zur herstellung eines insektizids von diesen stämmen |
| EP2231750A2 (en) * | 2007-11-26 | 2010-09-29 | Cognis IP Management GmbH | Polyamides prepared from long-chain dicarboxylic acids and methods for making the polyamides |
| CN101270374B (zh) * | 2008-05-23 | 2011-06-29 | 中国科学院微生物研究所 | 微生物转化油脂生产饱和及不饱和α,ω-二羧酸的方法 |
| FR2932807B1 (fr) * | 2008-06-20 | 2011-12-30 | Arkema France | Polyamide, composition comprenant un tel polyamide et leurs utilisations. |
| FR2933696B1 (fr) * | 2008-07-10 | 2010-08-20 | Arkema France | Procede de synthese d'acides omega-amino-alcanoiques ou de leurs esters a partir d'acides gras naturels. |
| FR2941694B1 (fr) | 2009-02-05 | 2011-02-11 | Arkema France | Procede de synthese d'un omega-aminoacide ou ester a partir d'un acide ou ester gras mono-insature. |
| US8501989B2 (en) | 2009-06-13 | 2013-08-06 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| EP2440513B1 (en) | 2009-06-13 | 2018-08-22 | Archer-Daniels-Midland Company | Production of glutaric acid and derivatives from carbohydrate-containing materials |
| US8669397B2 (en) | 2009-06-13 | 2014-03-11 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| CA2765849A1 (en) | 2009-07-02 | 2011-01-06 | Verdezyne, Inc. | Biological methods for preparing adipic acid |
| US8669393B2 (en) | 2010-03-05 | 2014-03-11 | Rennovia, Inc. | Adipic acid compositions |
| US9770705B2 (en) | 2010-06-11 | 2017-09-26 | Rennovia Inc. | Oxidation catalysts |
| US8728798B2 (en) | 2011-05-03 | 2014-05-20 | Verdezyne, Inc. | Biological methods for preparing adipic acid |
| US8343752B2 (en) | 2011-05-03 | 2013-01-01 | Verdezyne, Inc. | Biological methods for preparing adipic acid |
| CN110218745A (zh) * | 2018-03-01 | 2019-09-10 | 上海凯赛生物技术研发中心有限公司 | 发酵生产长链二元酸的方法及其得到的长链二元酸 |
| CN110218746A (zh) * | 2018-03-01 | 2019-09-10 | 上海凯赛生物技术研发中心有限公司 | 发酵生产长链二元酸的方法及发酵液、发酵处理液、污水 |
| EP3550014B1 (en) | 2018-04-04 | 2021-03-10 | Cathay Biotech Inc. | Directed evolution of cyp52a12 gene and its use in dicarboxylic acid production |
| CN110541008A (zh) * | 2018-05-29 | 2019-12-06 | 上海凯赛生物技术股份有限公司 | 一种长链二元酸铵的制备方法及其应用 |
| CN111850060A (zh) * | 2019-04-25 | 2020-10-30 | 上海凯赛生物技术股份有限公司 | 一种发酵生产十六碳二元酸的方法、十六碳二元酸及其制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5325032B2 (enExample) * | 1972-06-08 | 1978-07-24 | ||
| JPS57206394A (en) * | 1981-06-16 | 1982-12-17 | Mitsui Petrochem Ind Ltd | Preparation of dicarboxylic acid |
| DE3540834A1 (de) * | 1985-11-18 | 1987-05-21 | Henkel Kgaa | Verfahren zur herstellung von dicarbonsaeuren |
| EP0254331B1 (en) | 1986-05-28 | 1990-05-09 | Akzo N.V. | Process for the preparation of agglomerates containing diperoxydodecanedioic acid, and their use in bleaching compositions |
| US5254466A (en) * | 1989-11-06 | 1993-10-19 | Henkel Research Corporation | Site-specific modification of the candida tropicals genome |
| WO1991014781A1 (en) * | 1990-03-19 | 1991-10-03 | Henkel Research Corporation | METHOD FOR INCREASING THE OMEGA-HYDROXYLASE ACTIVITY IN $i(CANDIDA TROPICALIS) |
| US5733774A (en) * | 1995-02-02 | 1998-03-31 | Ecoscience Corporation | Method and composition for producing stable bacteria and bacterial formulations |
| US5962285A (en) | 1995-09-08 | 1999-10-05 | Henkel Corporation | Process for making polycarboxylic acids |
| US6004784A (en) | 1998-09-14 | 1999-12-21 | General Electric Co. | Fermentation medium and method for producing α, ω -alkanedicarboxylic acids |
| US6066480A (en) * | 1998-09-21 | 2000-05-23 | General Electric Company | Method for high specific bioproductivity of α,ω-alkanedicarboxylic acids |
-
2001
- 2001-01-04 US US09/754,158 patent/US6569670B2/en not_active Expired - Fee Related
- 2001-01-05 WO PCT/US2001/000471 patent/WO2001051605A1/en not_active Ceased
- 2001-01-05 ES ES01901830T patent/ES2300315T3/es not_active Expired - Lifetime
- 2001-01-05 AU AU27686/01A patent/AU2768601A/en not_active Abandoned
- 2001-01-05 AT AT01901830T patent/ATE387489T1/de active
- 2001-01-05 CN CN01803479A patent/CN1394232A/zh active Pending
- 2001-01-05 EP EP01901830A patent/EP1244771B1/en not_active Expired - Lifetime
- 2001-01-05 CA CA002396300A patent/CA2396300A1/en not_active Abandoned
- 2001-01-05 DK DK01901830T patent/DK1244771T3/da active
- 2001-01-05 JP JP2001551179A patent/JP4666867B2/ja not_active Expired - Fee Related
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|---|---|
| CN1394232A (zh) | 2003-01-29 |
| US6569670B2 (en) | 2003-05-27 |
| US20020028499A1 (en) | 2002-03-07 |
| EP1244771A1 (en) | 2002-10-02 |
| AU2768601A (en) | 2001-07-24 |
| JP2003519484A (ja) | 2003-06-24 |
| ES2300315T3 (es) | 2008-06-16 |
| DK1244771T3 (da) | 2008-06-30 |
| JP4666867B2 (ja) | 2011-04-06 |
| EP1244771A4 (en) | 2004-06-23 |
| WO2001051605A1 (en) | 2001-07-19 |
| ATE387489T1 (de) | 2008-03-15 |
| EP1244771B1 (en) | 2008-02-27 |
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