CN112778246A - 一种维生素c乙基醚合成方法 - Google Patents
一种维生素c乙基醚合成方法 Download PDFInfo
- Publication number
- CN112778246A CN112778246A CN202110035754.0A CN202110035754A CN112778246A CN 112778246 A CN112778246 A CN 112778246A CN 202110035754 A CN202110035754 A CN 202110035754A CN 112778246 A CN112778246 A CN 112778246A
- Authority
- CN
- China
- Prior art keywords
- vitamin
- ethyl ether
- ascorbic acid
- reaction
- synthesizing
- 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
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- ZGSCRDSBTNQPMS-UJURSFKZSA-N 3-O-Ethylascorbic acid Chemical group CCOC1=C(O)C(=O)O[C@@H]1[C@@H](O)CO ZGSCRDSBTNQPMS-UJURSFKZSA-N 0.000 title claims abstract description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 26
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 16
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 87
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229930003268 Vitamin C Natural products 0.000 claims abstract description 23
- 235000019154 vitamin C Nutrition 0.000 claims abstract description 23
- 239000011718 vitamin C Substances 0.000 claims abstract description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 15
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims abstract description 14
- 235000011150 stannous chloride Nutrition 0.000 claims abstract description 14
- 239000001119 stannous chloride Substances 0.000 claims abstract description 14
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims abstract description 13
- 125000006239 protecting group Chemical group 0.000 claims abstract description 7
- 230000001681 protective effect Effects 0.000 claims abstract description 7
- 230000001012 protector Effects 0.000 claims abstract description 7
- 239000000376 reactant Substances 0.000 claims abstract description 5
- 239000002798 polar solvent Substances 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- 229960005070 ascorbic acid Drugs 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 20
- 239000002211 L-ascorbic acid Substances 0.000 claims description 19
- 235000000069 L-ascorbic acid Nutrition 0.000 claims description 19
- 238000003756 stirring Methods 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 8
- XYJQBHCHAZPWHA-UHFFFAOYSA-N CC(C)C([CH2-])=O Chemical compound CC(C)C([CH2-])=O XYJQBHCHAZPWHA-UHFFFAOYSA-N 0.000 claims description 8
- 239000012295 chemical reaction liquid Substances 0.000 claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 230000002152 alkylating effect Effects 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000001704 evaporation Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 abstract description 11
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 230000008569 process Effects 0.000 abstract description 5
- 239000003444 phase transfer catalyst Substances 0.000 abstract description 3
- 239000011347 resin Substances 0.000 abstract description 3
- 229920005989 resin Polymers 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 230000036632 reaction speed Effects 0.000 abstract description 2
- 230000002195 synergetic effect Effects 0.000 abstract description 2
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 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 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 6
- 229920003303 ion-exchange polymer Polymers 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- 229940120145 3-o-ethylascorbic acid Drugs 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 Ethyl ascorbic acid Chemical compound 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000003700 vitamin C derivatives Chemical class 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/62—Three oxygen atoms, e.g. ascorbic acid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0239—Quaternary ammonium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN202110035754.0A CN112778246B (zh) | 2021-01-12 | 2021-01-12 | 一种维生素c乙基醚合成方法 |
Applications Claiming Priority (1)
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CN202110035754.0A CN112778246B (zh) | 2021-01-12 | 2021-01-12 | 一种维生素c乙基醚合成方法 |
Publications (2)
Publication Number | Publication Date |
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CN112778246A true CN112778246A (zh) | 2021-05-11 |
CN112778246B CN112778246B (zh) | 2022-02-25 |
Family
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Family Applications (1)
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CN202110035754.0A Active CN112778246B (zh) | 2021-01-12 | 2021-01-12 | 一种维生素c乙基醚合成方法 |
Country Status (1)
Country | Link |
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CN (1) | CN112778246B (zh) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5143648A (en) * | 1989-07-20 | 1992-09-01 | Nippon Hypox Laboratories Incorporated | Ascorbic acid derivative and use as antioxidant |
CN103113333A (zh) * | 2012-12-20 | 2013-05-22 | 浙江普洛康裕制药有限公司 | 一种维生素c乙基醚的合成方法 |
CN111559995A (zh) * | 2020-06-09 | 2020-08-21 | 郑州轻工业大学 | 一种抗坏血酸乙基醚的制备工艺 |
CN112142697A (zh) * | 2020-10-28 | 2020-12-29 | 浙江拓普药业股份有限公司 | 一种Vc乙基醚的生产工艺 |
-
2021
- 2021-01-12 CN CN202110035754.0A patent/CN112778246B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5143648A (en) * | 1989-07-20 | 1992-09-01 | Nippon Hypox Laboratories Incorporated | Ascorbic acid derivative and use as antioxidant |
CN103113333A (zh) * | 2012-12-20 | 2013-05-22 | 浙江普洛康裕制药有限公司 | 一种维生素c乙基醚的合成方法 |
CN111559995A (zh) * | 2020-06-09 | 2020-08-21 | 郑州轻工业大学 | 一种抗坏血酸乙基醚的制备工艺 |
CN112142697A (zh) * | 2020-10-28 | 2020-12-29 | 浙江拓普药业股份有限公司 | 一种Vc乙基醚的生产工艺 |
Non-Patent Citations (3)
Title |
---|
ABU T. KHAN 等: "Tetrabutylammonium tribromide (TBATB): a mild and efficient catalyst for O-isopropylidenation of carbohydrates", 《CARBOHYDRATE RESEARCH》 * |
CARRY H.H.EMONS 等: "A new convenient method for the synthesis of chiral C3-synthons", 《TETRAHEDRON: ASYMMETRY》 * |
刘鹰翔主编: "《药物合成反应》", 31 August 2017, 中国中医药出版社 * |
Also Published As
Publication number | Publication date |
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CN112778246B (zh) | 2022-02-25 |
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Legal Events
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PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
CP01 | Change in the name or title of a patent holder | ||
CP01 | Change in the name or title of a patent holder |
Address after: 201500 Jinshan District, Shanghai Patentee after: Shanghai Jiakai Biological Co.,Ltd. Address before: 201500 Jinshan District, Shanghai Patentee before: SHANGHAI JIAKAI BIOLOGICAL TECHNOLOGY Co.,Ltd. |
|
CP02 | Change in the address of a patent holder | ||
CP02 | Change in the address of a patent holder |
Address after: No. 818 Tiangong Road, Jinshan District, Shanghai, 200540 Patentee after: Shanghai Jiakai Biological Co.,Ltd. Address before: 201500 Jinshan District, Shanghai Patentee before: Shanghai Jiakai Biological Co.,Ltd. |