CN1570124A - Long chain normal dibasic acid production method - Google Patents
Long chain normal dibasic acid production method Download PDFInfo
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- CN1570124A CN1570124A CN 200410018255 CN200410018255A CN1570124A CN 1570124 A CN1570124 A CN 1570124A CN 200410018255 CN200410018255 CN 200410018255 CN 200410018255 A CN200410018255 A CN 200410018255A CN 1570124 A CN1570124 A CN 1570124A
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- acid
- alkane
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- fermentation
- liquid
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- 238000004519 manufacturing process Methods 0.000 title claims description 24
- 238000000034 method Methods 0.000 claims abstract description 106
- 238000000855 fermentation Methods 0.000 claims abstract description 89
- 230000004151 fermentation Effects 0.000 claims abstract description 83
- 239000007788 liquid Substances 0.000 claims abstract description 62
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 54
- 238000002425 crystallisation Methods 0.000 claims abstract description 46
- 239000012043 crude product Substances 0.000 claims abstract description 22
- 239000000758 substrate Substances 0.000 claims abstract description 17
- 108090000790 Enzymes Proteins 0.000 claims abstract description 7
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- 239000003960 organic solvent Substances 0.000 claims abstract 5
- 238000009834 vaporization Methods 0.000 claims abstract 3
- 230000008016 vaporization Effects 0.000 claims abstract 3
- 150000007520 diprotic acids Chemical class 0.000 claims description 74
- 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 description 31
- 239000008103 glucose Substances 0.000 claims description 31
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 241001052560 Thallis Species 0.000 claims description 19
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 229940041514 candida albicans extract Drugs 0.000 claims description 17
- 239000012138 yeast extract Substances 0.000 claims description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 230000031018 biological processes and functions Effects 0.000 claims description 16
- 239000004202 carbamide Substances 0.000 claims description 14
- 238000004821 distillation Methods 0.000 claims description 14
- 150000002632 lipids Chemical class 0.000 claims description 14
- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- 230000003287 optical effect Effects 0.000 claims description 10
- 241000222178 Candida tropicalis Species 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
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- 239000011780 sodium chloride Substances 0.000 claims description 9
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- 238000005374 membrane filtration Methods 0.000 claims description 7
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- 230000001580 bacterial effect Effects 0.000 claims description 6
- 238000007670 refining Methods 0.000 claims description 6
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 5
- 229930006000 Sucrose Natural products 0.000 claims description 5
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 229940043232 butyl acetate Drugs 0.000 claims description 4
- 238000013016 damping Methods 0.000 claims description 4
- 239000012530 fluid Substances 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 238000002203 pretreatment Methods 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 229910000397 disodium phosphate Inorganic materials 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- DFIWJEVKLWMZBI-UHFFFAOYSA-M sodium;dihydrogen phosphate;phosphoric acid Chemical compound [Na+].OP(O)(O)=O.OP(O)([O-])=O DFIWJEVKLWMZBI-UHFFFAOYSA-M 0.000 claims description 3
- 238000000975 co-precipitation Methods 0.000 claims description 2
- 239000013530 defoamer Substances 0.000 claims description 2
- 238000009413 insulation Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000000108 ultra-filtration Methods 0.000 claims description 2
- 239000007853 buffer solution Substances 0.000 claims 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 2
- 230000015556 catabolic process Effects 0.000 claims 1
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- 238000001471 micro-filtration Methods 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 230000008025 crystallization Effects 0.000 abstract description 45
- 239000000463 material Substances 0.000 abstract description 19
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 10
- 229930195729 fatty acid Natural products 0.000 abstract description 10
- 239000000194 fatty acid Substances 0.000 abstract description 10
- -1 thermosol Polymers 0.000 abstract description 8
- 239000004677 Nylon Substances 0.000 abstract description 7
- 229920001778 nylon Polymers 0.000 abstract description 7
- 150000004665 fatty acids Chemical class 0.000 abstract description 6
- 229920000728 polyester Polymers 0.000 abstract description 6
- 230000020477 pH reduction Effects 0.000 abstract 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 238000000526 short-path distillation Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 108
- 239000000047 product Substances 0.000 description 69
- 235000011121 sodium hydroxide Nutrition 0.000 description 36
- 239000002904 solvent Substances 0.000 description 24
- 230000001105 regulatory effect Effects 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 13
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- 238000011534 incubation Methods 0.000 description 12
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- 235000002017 Zea mays subsp mays Nutrition 0.000 description 11
- 235000005822 corn Nutrition 0.000 description 11
- 239000006052 feed supplement Substances 0.000 description 11
- 238000001514 detection method Methods 0.000 description 10
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 10
- 239000008399 tap water Substances 0.000 description 9
- 235000020679 tap water Nutrition 0.000 description 9
- 230000009466 transformation Effects 0.000 description 9
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 8
- 230000004927 fusion Effects 0.000 description 8
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 7
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 7
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 239000005642 Oleic acid Substances 0.000 description 7
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 7
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 7
- 238000004448 titration Methods 0.000 description 7
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 6
- 230000001954 sterilising effect Effects 0.000 description 6
- 238000004659 sterilization and disinfection Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000004831 Hot glue Substances 0.000 description 4
- 239000005639 Lauric acid Substances 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- 239000001888 Peptone Substances 0.000 description 4
- 108010080698 Peptones Proteins 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 230000002255 enzymatic effect Effects 0.000 description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical group CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 229940098695 palmitic acid Drugs 0.000 description 4
- 235000019319 peptone Nutrition 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
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- 230000001133 acceleration Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000012262 fermentative production Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
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- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- 102100028175 Abasic site processing protein HMCES Human genes 0.000 description 1
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- 230000007935 neutral effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011218 seed culture Methods 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- ZTUXEFFFLOVXQE-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCC(O)=O ZTUXEFFFLOVXQE-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
Manufacturer | Production technique | Total acid (%) | Single acid (%) | Fusing point (℃) | Thermostability 440/550nm |
??Dupont | Chemical method | ??99.78 | ??99.27 | ????129.5-130.6 | ??87/93 |
??Ube | Chemical method | ??99.58 | ??98.60 | ????129.4-130.6 | ??85/92 |
Zibo is extensively logical | Fermentation method | ??99.21 | ??98.13 | ????128.9-130.0 | ??81/85 |
Sample 1 | Biological process | ??99.31 | ??98.12 | ????129.2-130.3 | ??86/92 |
Sample 2 | Biological process | ??99.45 | ??98.24 | ????129.1-130.2 | ??87/93 |
Sample 3 | Biological process | ??99.72 | ??99.23 | ????129.4-130.5 | ??87/93 |
Claims (29)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN 200410018255 CN1292072C (en) | 2004-05-12 | 2004-05-12 | Long chain normal dibasic acid production method |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200410018255 CN1292072C (en) | 2004-05-12 | 2004-05-12 | Long chain normal dibasic acid production method |
Publications (2)
Publication Number | Publication Date |
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CN1570124A true CN1570124A (en) | 2005-01-26 |
CN1292072C CN1292072C (en) | 2006-12-27 |
Family
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CN 200410018255 Expired - Lifetime CN1292072C (en) | 2004-05-12 | 2004-05-12 | Long chain normal dibasic acid production method |
Country Status (1)
Country | Link |
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CN (1) | CN1292072C (en) |
Cited By (49)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2008011763A1 (en) * | 2006-07-20 | 2008-01-31 | Cathay R & D Center | A curing agent for powder coating and the preparation method of the long chain dicarboxylic acid polyanhydride used in said powder coating |
CN101121653B (en) * | 2006-08-07 | 2011-03-09 | 上海凯赛生物技术研发中心有限公司 | Long carbon-chain dibasic acid prepared from fatty acids or derivatives thereof and preparation method for the long carbon-chain dibasic acid |
CN102061316A (en) * | 2010-04-30 | 2011-05-18 | 山东瀚霖生物技术有限公司 | Preparation method of long carbon chain dibasic acid |
CN102476987A (en) * | 2010-11-29 | 2012-05-30 | 中国石油化工股份有限公司 | Method for refining long chain binary acid by combining ultrafiltration and liquid-liquid extraction |
CN102911036A (en) * | 2011-08-01 | 2013-02-06 | 中国石油化工股份有限公司 | Method for obtaining high pure dicarboxylic acid |
CN103121956A (en) * | 2011-11-21 | 2013-05-29 | 中国石油化工股份有限公司 | Method for preparing long-chain dibasic acid diester by using long-chain dibasic acid fermentation broth |
CN103243032A (en) * | 2012-02-10 | 2013-08-14 | 上海凯赛生物技术研发中心有限公司 | Sake candida and fermentation method thereof |
CN103243034A (en) * | 2012-02-10 | 2013-08-14 | 上海凯赛生物技术研发中心有限公司 | Sake candida and fermentation method thereof |
CN103243033A (en) * | 2012-02-10 | 2013-08-14 | 上海凯赛生物技术研发中心有限公司 | Sake candida and fermentation method thereof |
CN103243035A (en) * | 2012-02-10 | 2013-08-14 | 上海凯赛生物技术研发中心有限公司 | Sake candida and fermentation method thereof |
WO2013117026A1 (en) * | 2012-02-08 | 2013-08-15 | 上海凯赛生物技术研发中心有限公司 | Process for treating reaction solution containing long chain dicarboxylate |
CN103497100A (en) * | 2013-09-23 | 2014-01-08 | 中国石油化工股份有限公司 | Double-stage purification method of long chain dicarboxylic acid aqueous phase |
CN103570525A (en) * | 2012-07-25 | 2014-02-12 | 中国石油化工股份有限公司 | Method for refining long-chain dibasic acid |
CN103805275A (en) * | 2012-11-08 | 2014-05-21 | 中国石油化工股份有限公司 | Fermentation carbon source recycling method |
CN103965035A (en) * | 2013-01-30 | 2014-08-06 | 上海凯赛生物技术研发中心有限公司 | Refining method of long-chain binary acid |
WO2014121427A1 (en) * | 2013-02-05 | 2014-08-14 | Xu Jie | Method for removing organic amine nitrogen impurities in long-chain binary acids produced by microbiological method |
CN104693165A (en) * | 2013-12-10 | 2015-06-10 | 上海凯赛生物技术研发中心有限公司 | Method for producing long-chain diacid cyclic ethylene ester |
CN104693018A (en) * | 2013-12-10 | 2015-06-10 | 上海凯赛生物技术研发中心有限公司 | Method for demulsifying and refining long-chain diacid fermentation broth |
CN104844442A (en) * | 2014-02-18 | 2015-08-19 | 上海凯赛生物技术研发中心有限公司 | Method for preparing mixed acid from solvent mother liquor |
CN106148437A (en) * | 2015-04-14 | 2016-11-23 | 中国科学院微生物研究所 | A kind of method converting derivative of fatty acid production long-chain biatomic acid |
CN106660924A (en) * | 2014-06-12 | 2017-05-10 | 沃德金有限公司 | Purification of polycarboxylic acids |
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