CN101323581B - 一种甜菜碱、甜菜碱盐酸盐的合成方法 - Google Patents
一种甜菜碱、甜菜碱盐酸盐的合成方法 Download PDFInfo
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- CN101323581B CN101323581B CN2008100554562A CN200810055456A CN101323581B CN 101323581 B CN101323581 B CN 101323581B CN 2008100554562 A CN2008100554562 A CN 2008100554562A CN 200810055456 A CN200810055456 A CN 200810055456A CN 101323581 B CN101323581 B CN 101323581B
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- trimethylamine
- acetic acid
- trimethyl
- mono chloro
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- 239000003513 alkali Substances 0.000 title claims abstract description 29
- 235000016068 Berberis vulgaris Nutrition 0.000 title claims description 28
- 241000335053 Beta vulgaris Species 0.000 title claims description 28
- 238000010189 synthetic method Methods 0.000 title claims description 20
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims abstract description 66
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims abstract description 56
- 239000011347 resin Substances 0.000 claims abstract description 46
- 229920005989 resin Polymers 0.000 claims abstract description 46
- 238000010828 elution Methods 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000012153 distilled water Substances 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229950010582 betaine anhydrous Drugs 0.000 claims abstract description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 46
- 150000001450 anions Chemical class 0.000 claims description 27
- 238000004064 recycling Methods 0.000 claims description 13
- 238000005406 washing Methods 0.000 claims description 8
- 125000000129 anionic group Chemical group 0.000 claims description 7
- 229940106681 chloroacetic acid Drugs 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 4
- 229920001429 chelating resin Polymers 0.000 claims description 3
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- 238000000034 method Methods 0.000 abstract description 37
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- 239000000126 substance Substances 0.000 abstract description 7
- HOPSCVCBEOCPJZ-UHFFFAOYSA-N carboxymethyl(trimethyl)azanium;chloride Chemical class [Cl-].C[N+](C)(C)CC(O)=O HOPSCVCBEOCPJZ-UHFFFAOYSA-N 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 4
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- 238000005201 scrubbing Methods 0.000 abstract 1
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- 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
- 229910017053 inorganic salt Inorganic materials 0.000 description 6
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- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229960003403 betaine hydrochloride Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000003912 environmental pollution Methods 0.000 description 3
- 235000013379 molasses Nutrition 0.000 description 3
- 239000010970 precious metal Substances 0.000 description 3
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 2
- 235000019743 Choline chloride Nutrition 0.000 description 2
- 101100476962 Drosophila melanogaster Sirup gene Proteins 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- -1 Mono Chloro Acetic Acid basic metal Chemical class 0.000 description 2
- CZMRCDWAGMRECN-UHFFFAOYSA-N Rohrzucker Natural products OCC1OC(CO)(OC2OC(CO)C(O)C(O)C2O)C(O)C1O CZMRCDWAGMRECN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 150000003797 alkaloid derivatives Chemical class 0.000 description 2
- 238000009360 aquaculture Methods 0.000 description 2
- 244000144974 aquaculture Species 0.000 description 2
- 229910052728 basic metal Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 2
- 229960003178 choline chloride Drugs 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000000909 electrodialysis Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 238000009923 sugaring Methods 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- LXWDMCXKKRTXMR-UHFFFAOYSA-N 2-(dimethylamino)propanoic acid;hydrate Chemical compound O.CN(C)C(C)C(O)=O LXWDMCXKKRTXMR-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004381 Choline salt Substances 0.000 description 1
- 235000001427 Cylindropuntia imbricata Nutrition 0.000 description 1
- 240000005729 Cylindropuntia imbricata Species 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001252483 Kalimeris Species 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 235000019417 choline salt Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
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- 235000013399 edible fruits Nutrition 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
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- 239000011833 salt mixture Substances 0.000 description 1
- 159000000000 sodium salts Chemical group 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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Application Number | Priority Date | Filing Date | Title |
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CN2008100554562A CN101323581B (zh) | 2008-07-18 | 2008-07-18 | 一种甜菜碱、甜菜碱盐酸盐的合成方法 |
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CN2008100554562A CN101323581B (zh) | 2008-07-18 | 2008-07-18 | 一种甜菜碱、甜菜碱盐酸盐的合成方法 |
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CN101323581A CN101323581A (zh) | 2008-12-17 |
CN101323581B true CN101323581B (zh) | 2011-06-15 |
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CN2008100554562A Active CN101323581B (zh) | 2008-07-18 | 2008-07-18 | 一种甜菜碱、甜菜碱盐酸盐的合成方法 |
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Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102617374B (zh) * | 2011-01-31 | 2014-01-29 | 中牧实业股份有限公司 | 一种盐酸甜菜碱的制备方法 |
CN103570569B (zh) * | 2013-10-17 | 2015-06-03 | 华南理工大学 | 一种用甜菜酒精废液制备甜菜碱的方法 |
CN106631909B (zh) * | 2016-09-22 | 2018-11-09 | 精晶药业股份有限公司 | 一种胍基丁胺盐酸盐的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1165813A (zh) * | 1996-10-16 | 1997-11-26 | 中国农业科学院饲料研究所 | 饲料添加剂甜菜碱合成工艺 |
US20060009656A1 (en) * | 2004-07-09 | 2006-01-12 | Jiashu Zhang | Method of producing betaine compound |
-
2008
- 2008-07-18 CN CN2008100554562A patent/CN101323581B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1165813A (zh) * | 1996-10-16 | 1997-11-26 | 中国农业科学院饲料研究所 | 饲料添加剂甜菜碱合成工艺 |
US20060009656A1 (en) * | 2004-07-09 | 2006-01-12 | Jiashu Zhang | Method of producing betaine compound |
Non-Patent Citations (1)
Title |
---|
吴赛苏等.甜菜碱合成方法的改进.《化工时刊》.2007,第21卷(第1期),24-25. * |
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PB01 | Publication | ||
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SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20160718 Address after: 251500 Industrial Park, Linyi Economic Development Zone, Dezhou, Shandong province (east side of Fumin Road) Patentee after: SHANDONG E.FINE PHARMACY CO.,LTD. Address before: 030006 Taiyuan, Xiaodian District, Shanxi City Road, No. 92 Patentee before: SHANXI University |
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CP01 | Change in the name or title of a patent holder |
Address after: 251500 Industrial Park, Linyi Economic Development Zone, Dezhou, Shandong province (east side of Fumin Road) Patentee after: Shandong flying pharmaceutical Limited by Share Ltd. Address before: 251500 Industrial Park, Linyi Economic Development Zone, Dezhou, Shandong province (east side of Fumin Road) Patentee before: SHANDONG E.FINE PHARMACY CO.,LTD. |
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CP01 | Change in the name or title of a patent holder | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A synthetic method for betaine and betaine hydrochloride Effective date of registration: 20240103 Granted publication date: 20110615 Pledgee: Shandong Linyi Rural Commercial Bank Co.,Ltd. Pledgor: Shandong flying pharmaceutical Limited by Share Ltd. Registration number: Y2024980000327 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right |