CA2902089A1 - Method to purify ferulc acid and/or salts thereof - Google Patents
Method to purify ferulc acid and/or salts thereof Download PDFInfo
- Publication number
- CA2902089A1 CA2902089A1 CA2902089A CA2902089A CA2902089A1 CA 2902089 A1 CA2902089 A1 CA 2902089A1 CA 2902089 A CA2902089 A CA 2902089A CA 2902089 A CA2902089 A CA 2902089A CA 2902089 A1 CA2902089 A1 CA 2902089A1
- Authority
- CA
- Canada
- Prior art keywords
- ferulic acid
- salts
- mixture
- organic solvent
- impurities
- 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
- 150000003839 salts Chemical class 0.000 title claims abstract description 62
- 238000000034 method Methods 0.000 title claims abstract description 44
- 239000002253 acid Substances 0.000 title description 3
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 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 claims abstract description 80
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims abstract description 80
- 229940114124 ferulic acid Drugs 0.000 claims abstract description 80
- 235000001785 ferulic acid Nutrition 0.000 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 claims abstract description 79
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 239000012535 impurity Substances 0.000 claims abstract description 22
- 239000003960 organic solvent Substances 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000002425 crystallisation Methods 0.000 claims abstract description 12
- 230000008025 crystallization Effects 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 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 7
- 239000002244 precipitate Substances 0.000 claims abstract description 5
- 238000004062 sedimentation Methods 0.000 claims abstract description 5
- 239000012141 concentrate Substances 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 238000000746 purification Methods 0.000 claims description 16
- 238000011084 recovery Methods 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 238000005119 centrifugation Methods 0.000 claims description 4
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims description 4
- 239000011874 heated mixture Substances 0.000 claims 2
- 238000007873 sieving Methods 0.000 claims 2
- 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
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 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
- 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
- 230000003247 decreasing effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 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
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000129 anionic group Chemical group 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
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 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
- 150000004676 glycans Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 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
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 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 |
|---|---|
| CA2902089A1 true CA2902089A1 (en) | 2017-01-24 |
Family
ID=57834289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2902089A Abandoned CA2902089A1 (en) | 2015-07-23 | 2015-07-24 | Method to purify ferulc acid and/or salts thereof |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111072449A (zh) * | 2019-12-25 | 2020-04-28 | 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 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111072449A (zh) * | 2019-12-25 | 2020-04-28 | 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 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107074718A (zh) | 2017-08-18 |
| 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 |
| ES2791295T3 (es) | 2020-11-03 |
| EP3162788A1 (en) | 2017-05-03 |
| EP3162788A4 (en) | 2018-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20200723 |
|
| FZDE | Discontinued |
Effective date: 20230531 |