JP2020506194A - 天然バニリンの精製方法 - Google Patents
天然バニリンの精製方法 Download PDFInfo
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- JP2020506194A JP2020506194A JP2019541804A JP2019541804A JP2020506194A JP 2020506194 A JP2020506194 A JP 2020506194A JP 2019541804 A JP2019541804 A JP 2019541804A JP 2019541804 A JP2019541804 A JP 2019541804A JP 2020506194 A JP2020506194 A JP 2020506194A
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- vanillin
- natural vanillin
- hazen
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- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 title claims abstract description 119
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 title claims abstract description 118
- 235000012141 vanillin Nutrition 0.000 title claims abstract description 118
- 238000000034 method Methods 0.000 title claims abstract description 65
- 238000000746 purification Methods 0.000 title description 9
- 239000007788 liquid Substances 0.000 claims abstract description 45
- 239000002904 solvent Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 238000004821 distillation Methods 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000012535 impurity Substances 0.000 claims description 20
- 239000007789 gas Substances 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000001704 evaporation Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 239000012528 membrane Substances 0.000 claims description 6
- -1 alkyl acetate Chemical compound 0.000 claims description 5
- 230000001747 exhibiting effect Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 238000010352 biotechnological method Methods 0.000 claims 2
- 238000010586 diagram Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 15
- 238000000855 fermentation Methods 0.000 description 12
- 230000004151 fermentation Effects 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000005406 washing Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical group COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 5
- 229940114124 ferulic acid Drugs 0.000 description 5
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 5
- 235000001785 ferulic acid Nutrition 0.000 description 5
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 5
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical group COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000001953 sensory effect Effects 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 2
- 239000005770 Eugenol Substances 0.000 description 2
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000011138 biotechnological process Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 229960002217 eugenol Drugs 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 235000021474 generally recognized As safe (food) Nutrition 0.000 description 2
- 235000021473 generally recognized as safe (food ingredients) Nutrition 0.000 description 2
- 229960001867 guaiacol Drugs 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 2
- ZENOXNGFMSCLLL-UHFFFAOYSA-N vanillyl alcohol Chemical compound COC1=CC(CO)=CC=C1O ZENOXNGFMSCLLL-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 244000263375 Vanilla tahitensis Species 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000013048 microbiological method Methods 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 239000007959 natural flavoring substance Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Images
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/258—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/783—Separation; Purification; Stabilisation; Use of additives by gas-liquid treatment, e.g. by gas-liquid absorption
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
- A23L27/115—Natural spices, flavouring agents or condiments; Extracts thereof obtained by distilling, stripping, or recovering of volatiles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D1/00—Evaporating
- B01D1/22—Evaporating by bringing a thin layer of the liquid into contact with a heated surface
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/001—Processes specially adapted for distillation or rectification of fermented solutions
- B01D3/002—Processes specially adapted for distillation or rectification of fermented solutions by continuous methods
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/14—Fractional distillation or use of a fractionation or rectification column
- B01D3/143—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step
- B01D3/148—Fractional distillation or use of a fractionation or rectification column by two or more of a fractionation, separation or rectification step in combination with at least one evaporator
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/343—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances the substance being a gas
- B01D3/346—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances the substance being a gas the gas being used for removing vapours, e.g. transport gas
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0059—General arrangements of crystallisation plant, e.g. flow sheets
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/24—Synthetic spices, flavouring agents or condiments prepared by fermentation
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D2009/0086—Processes or apparatus therefor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Life Sciences & Earth Sciences (AREA)
- Nutrition Science (AREA)
- Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biotechnology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Seasonings (AREA)
- Extraction Or Liquid Replacement (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
− 特に、発酵基質からバニリンへの生物学的変換を可能にすることができる微生物の培養を含む、生物工学的プロセスに基づく「天然」ルート。発酵基質がフェルラ酸であるそのような方法は、特に、欧州特許第0885968号明細書から既知である。米国特許第5017388号明細書には、発酵基質がオイゲノールおよび/またはイソオイゲノールである方法が記載されている。これらの方法によって、天然バニリンと呼ばれるバニリンが調製される。
− 微生物が関与しない、グアイアコールから出発する従来の化学反応を含む「合成」ルート。これらの方法によって、合成バニリンと呼ばれるバニリンが調製される。
− ストリッピング装置、
− バニリンよりも揮発性の低い不純物を除去するための、好ましくは真空膜蒸留装置または薄膜蒸留装置における装置
を含む、本発明による方法を実施するための装置に関する。
− ストリッピング装置、
− バニリンよりも揮発性の低い不純物を除去するための装置、好ましくは真空膜蒸留装置または薄膜蒸留装置
を含む、特には本方法を実施するための装置にも関する。
− 粗製バニリン溶液を洗浄することができる洗浄装置、および/または
− 粗製バニリン溶液から溶媒を蒸発させることができる蒸留装置、および/または
− 精製天然バニリンを形成するための手段、好ましくは結晶化手段、
を更に含んでいてもよい。
図1に示されている方法を、溶液中での天然バニリンの製造方法から得られる流れから出発して行った。この流れは以下の組成を示した。
初期流が以下の組成を示したことを以外は実施例1と同様の手順を行う。
Claims (12)
- 天然バニリンを含む液体流F2を同伴ガスG1および/または気化液体L1と共にストリッピングする少なくとも1つの工程(b)を含む、生物工学的方法により得られる天然バニリンの精製方法であって、前記液体流F2中の天然バニリンの重量濃度が10%以上である方法。
- 前記液体流F2中の天然バニリンの重量濃度が30%以上、好ましくは50%以上、より好ましくは70%以上である、請求項1に記載の天然バニリンの精製方法。
- 任意選択的には水の存在下で、天然バニリンの製造に起因する流れF1の溶媒S1を蒸発させることによる天然バニリンの前記液体流F2の調製の予備工程(a)を更に含む、請求項1または2に記載の天然バニリンの精製方法。
- 工程(b)の後、バニリンよりも揮発性の低い化合物を、好ましくは真空膜蒸留装置または薄膜蒸留装置において除去する工程(c)を追加で含む、請求項1〜3のいずれか1項に記載の天然バニリンの精製方法。
- 前記同伴ガスG1または前記気化液体L1が、水、水蒸気、酢酸アルキル、アルコール、不活性ガス(N2、CO2、He、Ar、欠乏空気、およびこれらの混合物から選択される)からなる群から選択され、好ましくは前記同伴ガスG1または前記気化液体L1が水または水蒸気である、請求項1〜4のいずれか1項に記載の天然バニリンの精製方法。
- 工程(b)が、20℃以上、好ましくは30℃以上、より好ましくは40℃以上、更に好ましくは50℃以上の温度、および140℃以下、好ましくは120℃以下、より好ましくは100℃以下、更に好ましくは95℃の温度で行われる、請求項1〜5のいずれか1項に記載の天然バニリンの精製方法。
- 工程(b)が不活性雰囲気下で行われる、請求項1〜6のいずれか1項に記載の天然バニリンの精製方法。
- 工程(b)または(c)において得られる前記天然バニリンが、400ハーゼン以下、好ましくは200ハーゼン以下、より好ましくは100ハーゼン以下、より好ましくは50ハーゼン以下、更に好ましくは20ハーゼン以下(10重量%エタノール溶液中)の色を有することを特徴とする、請求項1〜7のいずれか1項に記載の天然バニリンの精製方法。
- 好ましくは結晶化により天然バニリンを形成する工程(d)を更に含む、請求項1〜8のいずれか1項に記載の方法。
- 固体の形態で存在し、その色が、10重量%エタノール溶液中で400ハーゼン以下、好ましくは200ハーゼン以下、より優先的には100ハーゼン以下、より優先的には50ハーゼン以下、更に優先的には20ハーゼン以下であることを特徴とする、請求項1〜9のいずれか1項に記載の方法によって得ることができる、生物工学的方法により得られる天然バニリン。
- 適合性のある官能特性を示すことを特徴とする、請求項10に記載の天然バニリン。
- − ストリッピング装置、
− バニリンよりも揮発性の低い不純物を除去するための装置、好ましくは真空膜蒸留装置または薄膜蒸留装置
を含む、特に請求項1〜9のいずれか1項に記載の方法の実施のための装置。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1751021 | 2017-02-08 | ||
FR1751021A FR3062652B1 (fr) | 2017-02-08 | 2017-02-08 | Procede de purification de la vanilline naturelle |
PCT/EP2018/053207 WO2018146210A1 (fr) | 2017-02-08 | 2018-02-08 | Procede de purification de la vanilline naturelle |
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US (1) | US10941100B2 (ja) |
EP (1) | EP3580195B1 (ja) |
JP (1) | JP7191835B2 (ja) |
CN (1) | CN110312700B (ja) |
BR (1) | BR112019014758B1 (ja) |
DE (2) | DE202018006559U1 (ja) |
ES (1) | ES2796558T3 (ja) |
FR (1) | FR3062652B1 (ja) |
MX (1) | MX2019009401A (ja) |
PT (1) | PT3580195T (ja) |
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FR3099478B1 (fr) | 2019-07-30 | 2021-07-09 | Rhodia Operations | Procédé de traitement d’une composition comprenant de la vanilline naturelle |
FR3099477B1 (fr) | 2019-07-30 | 2023-01-13 | Rhodia Operations | Compositions de vanilline naturelle |
FR3114813B1 (fr) | 2020-10-02 | 2023-11-17 | Rhodia Operations | Purification d’acide ferulique |
US20230373896A1 (en) | 2020-10-02 | 2023-11-23 | Rhodia Operations | Purification of ferulic acid |
FR3125818A1 (fr) | 2021-07-27 | 2023-02-03 | Rhodia Operations | Procédé d’extraction d’acide férulique et/ou ses sels comprenant une étape a) dans laquelle une biomasse est extrudée en présence d’une base |
NO347003B1 (en) | 2021-09-24 | 2023-04-03 | Autostore Tech As | Storage grid for vertical farming |
FR3134583A1 (fr) | 2022-04-15 | 2023-10-20 | Rhodia Operations | Procédé continu de croissance d’un microorganisme |
FR3134582A1 (fr) | 2022-04-15 | 2023-10-20 | Rhodia Operations | Procédé de préparation d’un composé de formule (I) par fermentation |
Citations (2)
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JPH0330683A (ja) * | 1989-06-20 | 1991-02-08 | Haarmann & Reimer Gmbh | 天然バニリンの製造方法 |
JP2016508482A (ja) * | 2013-01-24 | 2016-03-22 | ローディア オペレーションズ | 天然バニリンの精製方法 |
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US2745796A (en) * | 1953-10-21 | 1956-05-15 | Aschaffenburger Zellstoffwerke | Method of recovering vanillin |
DE1132113B (de) * | 1959-07-09 | 1962-06-28 | Aschaffenburger Zellstoffwerke | Verfahren zur Reinigung von Vanillin |
AT236357B (de) * | 1962-08-16 | 1964-10-26 | Chemie Linz Ag | Verfahren zur Reinigung von Acrylnitril |
US5582692A (en) * | 1994-10-07 | 1996-12-10 | Artisan Industries, Inc. | Method for the purification of vitamin E |
CA2238215A1 (en) | 1997-06-19 | 1998-12-19 | Markus Wetli | Process for the production of vanillin |
FR2984314B1 (fr) | 2011-12-15 | 2014-01-17 | Rhodia Operations | Procede de purification de la vanilline par extraction liquide-liquide |
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JPH0330683A (ja) * | 1989-06-20 | 1991-02-08 | Haarmann & Reimer Gmbh | 天然バニリンの製造方法 |
JP2016508482A (ja) * | 2013-01-24 | 2016-03-22 | ローディア オペレーションズ | 天然バニリンの精製方法 |
Also Published As
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MX2019009401A (es) | 2019-09-26 |
PT3580195T (pt) | 2022-04-04 |
FR3062652A1 (fr) | 2018-08-10 |
ES2796558T1 (es) | 2020-11-27 |
JP7191835B2 (ja) | 2022-12-19 |
CN110312700B (zh) | 2022-11-11 |
US10941100B2 (en) | 2021-03-09 |
DE202018006559U1 (de) | 2021-03-08 |
BR112019014758A2 (pt) | 2020-03-03 |
EP3580195A1 (fr) | 2019-12-18 |
EP3580195B1 (fr) | 2022-02-23 |
ES2796558T3 (es) | 2022-05-10 |
BR112019014758B1 (pt) | 2022-11-16 |
SK9324Y1 (sk) | 2021-09-29 |
WO2018146210A1 (fr) | 2018-08-16 |
DE18702741T1 (de) | 2021-01-07 |
US20190389792A1 (en) | 2019-12-26 |
SK500042021U1 (sk) | 2021-05-26 |
CN110312700A (zh) | 2019-10-08 |
FR3062652B1 (fr) | 2020-10-16 |
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