CN114790410A - Co-production system and process of ferulic acid methyl ester, phytosterol, fatty acid and fatty acid methyl ester - Google Patents
Co-production system and process of ferulic acid methyl ester, phytosterol, fatty acid and fatty acid methyl ester Download PDFInfo
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- CN114790410A CN114790410A CN202210413279.0A CN202210413279A CN114790410A CN 114790410 A CN114790410 A CN 114790410A CN 202210413279 A CN202210413279 A CN 202210413279A CN 114790410 A CN114790410 A CN 114790410A
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- AUJXJFHANFIVKH-GQCTYLIASA-N trans-methylferulate Chemical compound COC(=O)\C=C\C1=CC=C(O)C(OC)=C1 AUJXJFHANFIVKH-GQCTYLIASA-N 0.000 title claims abstract description 76
- 235000019387 fatty acid methyl ester Nutrition 0.000 title claims abstract description 40
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 38
- 239000000194 fatty acid Substances 0.000 title claims abstract description 38
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 38
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 38
- AUJXJFHANFIVKH-UHFFFAOYSA-N methyl cis-ferulate Natural products COC(=O)C=CC1=CC=C(O)C(OC)=C1 AUJXJFHANFIVKH-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 32
- -1 phytosterol Natural products 0.000 title claims abstract description 23
- 230000008569 process Effects 0.000 title claims abstract description 14
- 238000006136 alcoholysis reaction Methods 0.000 claims abstract description 81
- 238000000605 extraction Methods 0.000 claims abstract description 33
- 235000019774 Rice Bran oil Nutrition 0.000 claims abstract description 29
- 239000008165 rice bran oil Substances 0.000 claims abstract description 29
- 238000012545 processing Methods 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims description 166
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 158
- 239000003921 oil Substances 0.000 claims description 115
- 235000019198 oils Nutrition 0.000 claims description 115
- 238000004821 distillation Methods 0.000 claims description 92
- 241000209094 Oryza Species 0.000 claims description 87
- 235000007164 Oryza sativa Nutrition 0.000 claims description 87
- 235000009566 rice Nutrition 0.000 claims description 87
- 239000000463 material Substances 0.000 claims description 75
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- 238000003860 storage Methods 0.000 claims description 48
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- 239000000047 product Substances 0.000 claims description 34
- 238000001035 drying Methods 0.000 claims description 30
- 238000011084 recovery Methods 0.000 claims description 26
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 239000012535 impurity Substances 0.000 claims description 18
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- 239000006227 byproduct Substances 0.000 claims description 14
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 claims description 11
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 claims description 11
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-UHFFFAOYSA-N 0.000 claims description 11
- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 claims description 11
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 claims description 11
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 claims description 11
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- JTLOUXXZZFFBBW-UHFFFAOYSA-N isoferulic acid methyl ester Natural products COC(=O)C=CC1=CC=C(OC)C(O)=C1 JTLOUXXZZFFBBW-UHFFFAOYSA-N 0.000 claims description 5
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 235000019421 lipase Nutrition 0.000 description 1
- 108010022197 lipoprotein cholesterol Proteins 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 235000017524 noni Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229940075999 phytosterol ester Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 235000015500 sitosterol Nutrition 0.000 description 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 1
- 231100000245 skin permeability Toxicity 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- GHIZCSMTYWOBQA-BZSCQJQFSA-N spinasterol Natural products CC[C@H](C=C[C@@H](C)[C@@H]1CC[C@@]2(C)C3=CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C)C(C)C GHIZCSMTYWOBQA-BZSCQJQFSA-N 0.000 description 1
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 description 1
- 235000016831 stigmasterol Nutrition 0.000 description 1
- 229940032091 stigmasterol Drugs 0.000 description 1
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 238000003911 water pollution Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0083—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils with addition of auxiliary substances, e.g. cristallisation promotors, filter aids, melting point depressors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/12—Refining fats or fatty oils by distillation
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/16—Refining fats or fatty oils by mechanical means
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- Mechanical Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Oil name | Sterol content (%) | Oil name | Sterol content(%) |
Soybean oil | 0.15~0.38 | Olive oil | 0.11~0.31 |
Rapeseed oil | 0.35~0.51 | Sunflower seed oil | 0.35~0.75 |
Rice bran oil | 0.75~1.80 | Tea oil | 0.10~0.60 |
Corn oil | 0.58~1.50 | Wheat germ oil | 1.30~2.60 |
Palm oil | 0.03~0.26 | Sesame oil | 0.17~0.30 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210413279.0A CN114790410A (en) | 2022-04-20 | 2022-04-20 | Co-production system and process of ferulic acid methyl ester, phytosterol, fatty acid and fatty acid methyl ester |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210413279.0A CN114790410A (en) | 2022-04-20 | 2022-04-20 | Co-production system and process of ferulic acid methyl ester, phytosterol, fatty acid and fatty acid methyl ester |
Publications (1)
Publication Number | Publication Date |
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CN114790410A true CN114790410A (en) | 2022-07-26 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202210413279.0A Pending CN114790410A (en) | 2022-04-20 | 2022-04-20 | Co-production system and process of ferulic acid methyl ester, phytosterol, fatty acid and fatty acid methyl ester |
Country Status (1)
Country | Link |
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CN (1) | CN114790410A (en) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103254993A (en) * | 2013-06-04 | 2013-08-21 | 山东圣地嘉禾生物工程有限公司 | Rice bran crude oil separation method |
CN112126514A (en) * | 2020-09-23 | 2020-12-25 | 周红茹 | Oil and fat refining system |
-
2022
- 2022-04-20 CN CN202210413279.0A patent/CN114790410A/en active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103254993A (en) * | 2013-06-04 | 2013-08-21 | 山东圣地嘉禾生物工程有限公司 | Rice bran crude oil separation method |
CN112126514A (en) * | 2020-09-23 | 2020-12-25 | 周红茹 | Oil and fat refining system |
Non-Patent Citations (4)
Title |
---|
吴鹏等: "短程蒸馏原理及工业应用", 化工进展, pages 49 - 52 * |
林文等: "分子蒸馏分离米糠毛油中游离脂肪酸的工艺研究", 中国粮油学报, vol. 30, no. 2, pages 68 - 73 * |
郑诗超等: "天然抗氧化剂在油脂中的应用研究", 食品与机械, pages 7 - 8 * |
黄妙玲等: "分子蒸馏技术制备米糠油植物甾醇的工艺研究", 中国食品添加剂, pages 216 - 219 * |
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Inventor after: Zhou Hongru Inventor after: Liu Wenjie Inventor after: Cao Wei Inventor before: Zhou Hongru |
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Effective date of registration: 20240311 Address after: 410000, 1st Floor, Building 9, Zone 12, Huoyan Community, Gaoqiao Street, Yuhua District, Changsha City, Hunan Province, China Applicant after: Hunan Zhonggu Oil Technology Co.,Ltd. Country or region after: China Address before: 214085 Room 101, building 9, Xushe Xutian wisdom Park, Binhu District, Wuxi City, Jiangsu Province Applicant before: Zhou Hongru Country or region before: China |