ES2791295T3 - Procedimiento para purificar ácido ferúlico y/o sales del mismo - Google Patents
Procedimiento para purificar ácido ferúlico y/o sales del mismo Download PDFInfo
- Publication number
- ES2791295T3 ES2791295T3 ES15750912T ES15750912T ES2791295T3 ES 2791295 T3 ES2791295 T3 ES 2791295T3 ES 15750912 T ES15750912 T ES 15750912T ES 15750912 T ES15750912 T ES 15750912T ES 2791295 T3 ES2791295 T3 ES 2791295T3
- Authority
- ES
- Spain
- Prior art keywords
- ferulic acid
- salts
- mixture
- organic solvent
- water
- 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.)
- Active
Links
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 title claims abstract description 80
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 title claims abstract description 80
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 229940114124 ferulic acid Drugs 0.000 title claims abstract description 79
- 235000001785 ferulic acid Nutrition 0.000 title claims abstract description 79
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 title claims abstract description 79
- 150000003839 salts Chemical class 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 239000012535 impurity Substances 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 19
- 238000002425 crystallisation Methods 0.000 claims abstract description 15
- 230000008025 crystallization Effects 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007787 solid Substances 0.000 claims abstract description 8
- 238000001704 evaporation Methods 0.000 claims abstract description 7
- 239000012452 mother liquor Substances 0.000 claims abstract description 6
- 239000002244 precipitate Substances 0.000 claims abstract description 5
- 239000012141 concentrate Substances 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- 238000000746 purification Methods 0.000 claims description 16
- 238000011084 recovery Methods 0.000 claims description 10
- 238000000605 extraction Methods 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- 230000008020 evaporation Effects 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 238000005119 centrifugation Methods 0.000 claims description 4
- 238000004062 sedimentation Methods 0.000 claims description 4
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims description 3
- 238000007873 sieving Methods 0.000 claims 2
- 239000002904 solvent Substances 0.000 abstract description 8
- 239000013049 sediment Substances 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 210000002421 cell wall Anatomy 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 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 1
- 244000061520 Angelica archangelica Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000001287 Guettarda speciosa Nutrition 0.000 description 1
- 229920002488 Hemicellulose Polymers 0.000 description 1
- 241000244355 Ligusticum Species 0.000 description 1
- 235000019774 Rice Bran oil Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 150000001720 carbohydrates Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- -1 for example Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic 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
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- 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
-
- 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
-
- 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
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/MX2015/000109 WO2017014621A1 (es) | 2015-07-23 | 2015-07-23 | Método para purificar ácido ferulico y/o sales del mismo |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2791295T3 true ES2791295T3 (es) | 2020-11-03 |
Family
ID=57834289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15750912T Active ES2791295T3 (es) | 2015-07-23 | 2015-07-23 | Procedimiento para purificar ácido ferúlico y/o sales del mismo |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9732024B2 (enExample) |
| EP (1) | EP3162788B1 (enExample) |
| JP (1) | JP2018522065A (enExample) |
| CN (1) | CN107074718A (enExample) |
| CA (1) | CA2902089A1 (enExample) |
| ES (1) | ES2791295T3 (enExample) |
| MX (1) | MX390863B (enExample) |
| WO (1) | WO2017014621A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111072449B (zh) * | 2019-12-25 | 2021-09-14 | 湖南华诚生物资源股份有限公司 | 一种以含谷维素的皂脚为原料制备天然阿魏酸的方法 |
| CN111039772B (zh) * | 2019-12-25 | 2022-03-29 | 湖南华诚生物资源股份有限公司 | 一种谷维素生产过程产生的废渣的综合利用方法 |
| CN113203810A (zh) * | 2021-04-30 | 2021-08-03 | 西安绿泉科技有限公司 | 一种天然阿魏酸产品中气味检测方法 |
| CN113563157A (zh) * | 2021-08-31 | 2021-10-29 | 湖北省现代农业有限公司 | 一种成品油中阿魏酸的提取方法 |
| CN115448885A (zh) * | 2022-10-24 | 2022-12-09 | 生工生物工程（上海）股份有限公司 | 一种咪唑的纯化方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0778032B2 (ja) * | 1991-03-13 | 1995-08-23 | 和歌山県 | フェルラ酸の製造方法 |
| GB2301103B (en) | 1995-05-23 | 1999-12-22 | Danisco | An enzyme system comprising ferulic acid esterase |
| AU2003241211A1 (en) | 2003-06-19 | 2005-01-04 | Biokab, S.A. De C.V. | Method for the recovery of ferulic acid |
| CN1243708C (zh) * | 2003-11-29 | 2006-03-01 | 陶丽华 | 阿魏酸的提取纯化工艺 |
| JP2006067803A (ja) * | 2004-08-31 | 2006-03-16 | Okumoto Seifun Kk | フェルラ酸の製造方法 |
| JP5093873B2 (ja) * | 2006-06-28 | 2012-12-12 | 長谷川香料株式会社 | 精製クロロゲン酸の製造法 |
| CN101811958B (zh) * | 2010-05-12 | 2012-10-03 | 桂林甙元生物科技有限公司 | 从米糠油加工的废弃物中分离提取含量≥98%天然阿魏酸的工艺 |
| CN102060693B (zh) * | 2010-12-20 | 2013-11-13 | 大兴安岭嘉迪欧营养原料有限公司 | 一种富集纯化升麻中阿魏酸的方法 |
| CN102381960A (zh) * | 2011-08-31 | 2012-03-21 | 刘启民 | 一种从玉米皮中提取阿魏酸、对-香豆酸及戊聚糖的方法 |
| JP2014196272A (ja) * | 2013-03-29 | 2014-10-16 | 富士フイルム株式会社 | 分離方法、及びカフェ酸もしくはフェルラ酸の製造方法 |
| JP6513640B2 (ja) | 2013-05-21 | 2019-05-15 | ローディア オペレーションズ | 前処理ありのフェルラ酸の最適化抽出方法 |
| CN103254064B (zh) * | 2013-05-22 | 2015-08-05 | 暨南大学 | 一种阿魏酸的制备方法 |
-
2015
- 2015-07-23 CN CN201580000325.2A patent/CN107074718A/zh active Pending
- 2015-07-23 WO PCT/MX2015/000109 patent/WO2017014621A1/es not_active Ceased
- 2015-07-23 MX MX2015011381A patent/MX390863B/es unknown
- 2015-07-23 EP EP15750912.6A patent/EP3162788B1/en active Active
- 2015-07-23 JP JP2018523730A patent/JP2018522065A/ja active Pending
- 2015-07-23 ES ES15750912T patent/ES2791295T3/es active Active
- 2015-07-24 CA CA2902089A patent/CA2902089A1/en not_active Abandoned
- 2015-07-24 US US14/771,668 patent/US9732024B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN107074718A (zh) | 2017-08-18 |
| CA2902089A1 (en) | 2017-01-24 |
| MX390863B (es) | 2025-03-21 |
| US20170158595A1 (en) | 2017-06-08 |
| JP2018522065A (ja) | 2018-08-09 |
| US9732024B2 (en) | 2017-08-15 |
| EP3162788B1 (en) | 2020-02-19 |
| MX2015011381A (es) | 2017-03-20 |
| WO2017014621A1 (es) | 2017-01-26 |
| EP3162788A1 (en) | 2017-05-03 |
| EP3162788A4 (en) | 2018-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2791295T3 (es) | Procedimiento para purificar ácido ferúlico y/o sales del mismo | |
| US9487552B2 (en) | Method for preparing an extract of centella asiatica | |
| RU2640018C1 (ru) | Усовершенствованный способ получения экстракта гинкго билоба | |
| CN102531989B (zh) | 一种（s）-奥拉西坦的纯化方法 | |
| JP2018522890A5 (enExample) | ||
| TWI678360B (zh) | 生產檸檬酸衍生物非對映體方法 | |
| JP2018522065A5 (enExample) | ||
| CN101210034A (zh) | 三氯蔗糖结晶方法 | |
| CN105307490A (zh) | 同时提取和分离酯化和未酯化的单羟基类胡萝卜素的方法 | |
| US9420820B2 (en) | Method for isolating polyphenols from olive mill water | |
| ES2330127T3 (es) | Procedimiento de preparacion de bromhidrato de galantamina. | |
| CN104592053B (zh) | 一种高纯度泛酸钠的工业化制备方法 | |
| CN102875510A (zh) | 一种从显齿蛇葡萄中提取高含量二氢杨梅素的工艺方法 | |
| AU2017383071B2 (en) | Improved synthesis of lysine acetylsalicylate · glycine particles | |
| RU2283655C1 (ru) | Способ получения биологически активных веществ | |
| WO2024231278A1 (en) | Preparation process of quercetin and quercetin thus obtained | |
| WO2016085317A1 (es) | Método para extraer ácido ferúlico y/o sales del mismo | |
| CN107445878A (zh) | 叶黄素晶体及其制备工艺 | |
| WO2017222043A1 (ja) | ３－ヒドロキシイソ吉草酸アミノ酸塩の結晶及びその製造方法 | |
| CN109232677B (zh) | 一种使n-乙酰神经氨酸水合物转化为n-乙酰神经氨酸的方法 | |
| WO2017169311A1 (ja) | ネポジン高含有ギシギシ抽出物の製造方法及びネポジン高含有ギシギシ抽出物 | |
| CN106366158B (zh) | 一种肌肽的结晶方法 | |
| CN105061458B (zh) | 一种无毒、高纯银杏总内酯及其单体的制备方法 | |
| US3592843A (en) | Purification of l-dopa | |
| CN105294621A (zh) | 硝基邻苯二甲酸酐同分异构体混合物的分离方法 |