CN101613277B - 提高顺式二氢茉莉酮酸甲酯含量的方法 - Google Patents
提高顺式二氢茉莉酮酸甲酯含量的方法 Download PDFInfo
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- CN101613277B CN101613277B CN200910183251A CN200910183251A CN101613277B CN 101613277 B CN101613277 B CN 101613277B CN 200910183251 A CN200910183251 A CN 200910183251A CN 200910183251 A CN200910183251 A CN 200910183251A CN 101613277 B CN101613277 B CN 101613277B
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- dihydrojasmonate
- cis
- methyl
- isomer
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- 238000000034 method Methods 0.000 title claims abstract description 31
- KVWWIYGFBYDJQC-MNOVXSKESA-N methyl 2-[(1r,2s)-3-oxo-2-pentylcyclopentyl]acetate Chemical compound CCCCC[C@H]1[C@@H](CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-MNOVXSKESA-N 0.000 title claims abstract description 25
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical class CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 claims abstract description 48
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 32
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 28
- 239000012044 organic layer Substances 0.000 claims abstract description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
- 230000007935 neutral effect Effects 0.000 claims abstract description 15
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 14
- 230000035484 reaction time Effects 0.000 claims abstract description 11
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 10
- 239000002808 molecular sieve Substances 0.000 claims abstract description 9
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 9
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims abstract description 8
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims abstract description 7
- 239000001110 calcium chloride Substances 0.000 claims abstract description 7
- 229910001628 calcium chloride Inorganic materials 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 claims abstract description 5
- 235000011152 sodium sulphate Nutrition 0.000 claims abstract description 5
- 239000011592 zinc chloride Substances 0.000 claims abstract description 5
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 5
- 239000000047 product Substances 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 235000017550 sodium carbonate Nutrition 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 4
- AMAICRYCMCVAHT-UHFFFAOYSA-K calcium;sodium;trichloride Chemical compound [Na+].[Cl-].[Cl-].[Cl-].[Ca+2] AMAICRYCMCVAHT-UHFFFAOYSA-K 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229960003280 cupric chloride Drugs 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 16
- 238000001035 drying Methods 0.000 abstract description 13
- 125000003118 aryl group Chemical group 0.000 abstract description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract description 3
- 238000010790 dilution Methods 0.000 abstract description 2
- 239000012895 dilution Substances 0.000 abstract description 2
- 239000005457 ice water Substances 0.000 abstract 2
- 239000002274 desiccant Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 description 26
- 239000007789 gas Substances 0.000 description 16
- 238000001514 detection method Methods 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 230000001105 regulatory effect Effects 0.000 description 12
- 238000005303 weighing Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 230000008859 change Effects 0.000 description 7
- 230000009466 transformation Effects 0.000 description 7
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 6
- 239000003205 fragrance Substances 0.000 description 6
- 239000002304 perfume Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 cyclopentene ketone Chemical class 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- GEWDNTWNSAZUDX-WQMVXFAESA-N (-)-methyl jasmonate Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-WQMVXFAESA-N 0.000 description 2
- 241000207840 Jasminum Species 0.000 description 2
- 235000010254 Jasminum officinale Nutrition 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012084 conversion product Substances 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical group O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000686 essence Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- GEWDNTWNSAZUDX-UHFFFAOYSA-N methyl 7-epi-jasmonate Natural products CCC=CCC1C(CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- ILHZVKAXFCDFMT-UHFFFAOYSA-N 2-pentylcyclopent-2-en-1-one Chemical compound CCCCCC1=CCCC1=O ILHZVKAXFCDFMT-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007171 acid catalysis Methods 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentenylidene Natural products C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZIYVHBGGAOATLY-UHFFFAOYSA-N methylmalonic acid Chemical compound OC(=O)C(C)C(O)=O ZIYVHBGGAOATLY-UHFFFAOYSA-N 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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CN101613277B true CN101613277B (zh) | 2012-10-03 |
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CN104194933A (zh) * | 2014-08-22 | 2014-12-10 | 云南中烟工业有限责任公司 | 一种提高β-二氢大马酮品质的方法 |
CN115477581A (zh) * | 2022-09-13 | 2022-12-16 | 安徽金禾化学材料研究所有限公司 | 一种高顺式二氢茉莉酮酸甲酯的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0399788A2 (en) * | 1989-05-23 | 1990-11-28 | Nippon Zeon Co., Ltd. | Process for the preparation of 2,3 substituted cylopentanones. |
CN100999466A (zh) * | 2006-01-11 | 2007-07-18 | 浙江新和成股份有限公司 | 顺式-二氢茉莉酮酸甲酯的合成方法 |
-
2009
- 2009-07-30 CN CN200910183251A patent/CN101613277B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0399788A2 (en) * | 1989-05-23 | 1990-11-28 | Nippon Zeon Co., Ltd. | Process for the preparation of 2,3 substituted cylopentanones. |
CN100999466A (zh) * | 2006-01-11 | 2007-07-18 | 浙江新和成股份有限公司 | 顺式-二氢茉莉酮酸甲酯的合成方法 |
Non-Patent Citations (3)
Title |
---|
上海应用技术学院."二氢茉莉酮酸甲酯的合成进展".《香料香精化妆品》.2007,(第3期), |
许家喜."微波与有机化学反应的选择性".《化学进展》.2007,第19卷(第5期),700-712. |
金钦汉.《微波化学》.《微波化学》.科学出版社,1999, * |
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Address after: 223300 No. 111 Changjiang West Road, Huaiyin District, Jiangsu, Huaian Co-patentee after: Wanxiang Technology Co.,Ltd. Patentee after: HUAIYIN NORMAL University Address before: 223300 No. 111 Changjiang West Road, Huaiyin District, Jiangsu, Huaian Co-patentee before: HUAIAN WAN BANG SPICE INDUSTRY Co.,Ltd. Patentee before: huaiyin normal university |
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Address after: 223300 No. 216 Changjiang East Road, Huaiyin District, Jiangsu, Huaian Patentee after: Wanxiang Technology Group Co.,Ltd. Country or region after: China Address before: 223300 No. 216 Changjiang East Road, Huaiyin District, Jiangsu, Huaian Patentee before: Wanxiang Technology Co.,Ltd. Country or region before: China |