CN104355977A - 一种覆盆子酮的合成工艺 - Google Patents
一种覆盆子酮的合成工艺 Download PDFInfo
- Publication number
- CN104355977A CN104355977A CN201410618724.2A CN201410618724A CN104355977A CN 104355977 A CN104355977 A CN 104355977A CN 201410618724 A CN201410618724 A CN 201410618724A CN 104355977 A CN104355977 A CN 104355977A
- Authority
- CN
- China
- Prior art keywords
- reactor
- reaction
- raspberry ketone
- formaldehyde
- acetone
- 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.)
- Granted
Links
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 title claims abstract description 48
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 32
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 30
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 30
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 92
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 87
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 49
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 42
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 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 claims abstract description 8
- 230000035484 reaction time Effects 0.000 claims abstract description 8
- 238000012856 packing Methods 0.000 claims abstract description 6
- 239000003456 ion exchange resin Substances 0.000 claims abstract description 4
- 229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 4
- 229910001220 stainless steel Inorganic materials 0.000 claims abstract description 4
- 239000010935 stainless steel Substances 0.000 claims abstract description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 75
- 238000006243 chemical reaction Methods 0.000 claims description 70
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 63
- 238000010438 heat treatment Methods 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 20
- 229920005989 resin Polymers 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 17
- 238000009413 insulation Methods 0.000 claims description 14
- 239000003513 alkali Substances 0.000 claims description 9
- 239000008098 formaldehyde solution Substances 0.000 claims description 9
- 230000001186 cumulative effect Effects 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 7
- 238000010792 warming Methods 0.000 claims description 7
- 239000012043 crude product Substances 0.000 claims description 6
- 239000012670 alkaline solution Substances 0.000 claims description 4
- -1 butylene keto-alcohol Chemical compound 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 238000011068 loading method Methods 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 11
- 239000002994 raw material Substances 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000007086 side reaction Methods 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 3
- 239000003729 cation exchange resin Substances 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract 2
- 238000010992 reflux Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910001120 nichrome Inorganic materials 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 240000007651 Rubus glaucus Species 0.000 description 1
- 235000011034 Rubus glaucus Nutrition 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 230000031902 chemoattractant activity Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
Classifications
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- 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
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- 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
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201410618724.2A CN104355977B (zh) | 2014-11-06 | 2014-11-06 | 一种覆盆子酮的合成工艺 |
Applications Claiming Priority (1)
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CN201410618724.2A CN104355977B (zh) | 2014-11-06 | 2014-11-06 | 一种覆盆子酮的合成工艺 |
Publications (2)
Publication Number | Publication Date |
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CN104355977A true CN104355977A (zh) | 2015-02-18 |
CN104355977B CN104355977B (zh) | 2016-03-02 |
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Family Applications (1)
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CN201410618724.2A Active CN104355977B (zh) | 2014-11-06 | 2014-11-06 | 一种覆盆子酮的合成工艺 |
Country Status (1)
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108976110A (zh) * | 2017-05-30 | 2018-12-11 | 镇江杜微人才咨询有限公司 | 固体碱催化剂催化制备丁酮醇的实验方法 |
CN109516906A (zh) * | 2018-11-29 | 2019-03-26 | 厦门金达威维生素有限公司 | 一种催化反应精馏合成丁酮醇的方法和装置 |
FR3116819A1 (fr) | 2020-12-01 | 2022-06-03 | Rhodia Operations | Procédé de préparation de frambinone |
FR3117486A1 (fr) | 2020-12-14 | 2022-06-17 | Rhodia Operations | Procédé de préparation de frambinone |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2145308A1 (de) * | 1971-09-10 | 1973-03-15 | Basf Ag | Verfahren zur herstellung von 4(4-hydroxyphenyl)-butan-2-on |
GB2080284A (en) * | 1980-07-22 | 1982-02-03 | Chisso Corp | Method of producing 4-(4- Hydroxyphenyl)-2-butanone |
-
2014
- 2014-11-06 CN CN201410618724.2A patent/CN104355977B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2145308A1 (de) * | 1971-09-10 | 1973-03-15 | Basf Ag | Verfahren zur herstellung von 4(4-hydroxyphenyl)-butan-2-on |
GB2080284A (en) * | 1980-07-22 | 1982-02-03 | Chisso Corp | Method of producing 4-(4- Hydroxyphenyl)-2-butanone |
Non-Patent Citations (4)
Title |
---|
JUN-ICHI TATEIWA ET AL.: "Cation-Exchanged Montmorillonite-Catalyzed Facile Friedel-Crafts Alkylation of Hydroxy and Methoxy Aromatics with 4-Hydroxybutan-2-one To Produce Raspberry Ketone and Some Pharmaceutically Active Compounds", 《J. ORG. CHEM.》, vol. 59, 31 December 1994 (1994-12-31), pages 5901 - 5904, XP000468997, DOI: doi:10.1021/jo00099a017 * |
唐健: "复盆子酮的合成及应用", 《化工技术与开发》, vol. 35, no. 9, 30 September 2006 (2006-09-30), pages 21 - 23 * |
张立娟: "4-(对羟基苯)-2- 丁酮中间体的研制", 《河北化工》, vol. 30, no. 9, 30 September 2007 (2007-09-30), pages 43 * |
王云翔: "4-羟基-2-丁酮合成条件的研究", 《铁道师院学报( 自然科学版)》, vol. 12, no. 1, 31 March 1995 (1995-03-31), pages 9 - 13 * |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108976110A (zh) * | 2017-05-30 | 2018-12-11 | 镇江杜微人才咨询有限公司 | 固体碱催化剂催化制备丁酮醇的实验方法 |
CN109516906A (zh) * | 2018-11-29 | 2019-03-26 | 厦门金达威维生素有限公司 | 一种催化反应精馏合成丁酮醇的方法和装置 |
CN109516906B (zh) * | 2018-11-29 | 2021-10-08 | 厦门金达威维生素有限公司 | 一种催化反应精馏合成丁酮醇的方法和装置 |
FR3116819A1 (fr) | 2020-12-01 | 2022-06-03 | Rhodia Operations | Procédé de préparation de frambinone |
WO2022117670A1 (fr) | 2020-12-01 | 2022-06-09 | Rhodia Operations | Procédé de préparation de frambinone |
FR3117486A1 (fr) | 2020-12-14 | 2022-06-17 | Rhodia Operations | Procédé de préparation de frambinone |
WO2022129012A1 (fr) | 2020-12-14 | 2022-06-23 | Rhodia Operations | Procédé de préparation de frambinone |
Also Published As
Publication number | Publication date |
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CN104355977B (zh) | 2016-03-02 |
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Effective date of registration: 20181113 Address after: 245600 Shikeng, Xiaokou Town, Qimen County, Huangshan City, Anhui Province Patentee after: HUANGSHAN JULONG BIOLOGICAL ENERGY TECHNOLOGY CO.,LTD. Address before: No. 159, dragon pan Road, Nanjing, Jiangsu Patentee before: Nanjing Forestry University |
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Denomination of invention: Synthesis of raspberry ketone Effective date of registration: 20221205 Granted publication date: 20160302 Pledgee: Qimen Anhui rural commercial bank Limited by Share Ltd. Pledgor: HUANGSHAN JULONG BIOLOGICAL ENERGY TECHNOLOGY CO.,LTD. Registration number: Y2022980024782 |
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Date of cancellation: 20231008 Granted publication date: 20160302 Pledgee: Qimen Anhui rural commercial bank Limited by Share Ltd. Pledgor: HUANGSHAN JULONG BIOLOGICAL ENERGY TECHNOLOGY CO.,LTD. Registration number: Y2022980024782 |
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