CN101597223A - 榛子酮的合成方法 - Google Patents
榛子酮的合成方法 Download PDFInfo
- Publication number
- CN101597223A CN101597223A CNA200810123410XA CN200810123410A CN101597223A CN 101597223 A CN101597223 A CN 101597223A CN A200810123410X A CNA200810123410X A CN A200810123410XA CN 200810123410 A CN200810123410 A CN 200810123410A CN 101597223 A CN101597223 A CN 101597223A
- Authority
- CN
- China
- Prior art keywords
- methyl
- reaction
- filbertone
- pentanone
- amylene
- 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
- ARJWAURHQDJJAC-UHFFFAOYSA-N 5-Methyl-2-hepten-4-one Natural products CCC(C)C(=O)C=CC ARJWAURHQDJJAC-UHFFFAOYSA-N 0.000 title claims abstract description 19
- ARJWAURHQDJJAC-GQCTYLIASA-N filbertone Chemical compound CCC(C)C(=O)\C=C\C ARJWAURHQDJJAC-GQCTYLIASA-N 0.000 title claims abstract description 19
- 238000010189 synthetic method Methods 0.000 title claims abstract description 13
- UIHCLUNTQKBZGK-UHFFFAOYSA-N 3-methyl-2-pentanone Chemical compound CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 32
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims abstract description 32
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000009833 condensation Methods 0.000 claims abstract description 8
- 230000005494 condensation Effects 0.000 claims abstract description 8
- 239000004246 zinc acetate Substances 0.000 claims abstract description 8
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 4
- 238000004904 shortening Methods 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 8
- 238000003747 Grignard reaction Methods 0.000 abstract description 5
- 235000013599 spices Nutrition 0.000 abstract description 4
- 239000003205 fragrance Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 230000002194 synthesizing effect Effects 0.000 description 7
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 3
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001893 (2R)-2-methylbutanal Substances 0.000 description 1
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- BHVLLFQWFGHORS-UHFFFAOYSA-N C=CCC(CCC)=O.CC=1C=C(C=C(C(=O)O)C1)C(=O)O Chemical compound C=CCC(CCC)=O.CC=1C=C(C=C(C(=O)O)C1)C(=O)O BHVLLFQWFGHORS-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000014860 sensory perception of taste Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200810123410XA CN101597223B (zh) | 2008-06-03 | 2008-06-03 | 榛子酮的合成方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200810123410XA CN101597223B (zh) | 2008-06-03 | 2008-06-03 | 榛子酮的合成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101597223A true CN101597223A (zh) | 2009-12-09 |
CN101597223B CN101597223B (zh) | 2012-07-04 |
Family
ID=41418847
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN200810123410XA Active CN101597223B (zh) | 2008-06-03 | 2008-06-03 | 榛子酮的合成方法 |
Country Status (1)
Country | Link |
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CN (1) | CN101597223B (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102030626A (zh) * | 2010-11-16 | 2011-04-27 | 上海应用技术学院 | 一种5-甲基-2-庚烯-4-酮的制备方法 |
CN103058842A (zh) * | 2012-12-26 | 2013-04-24 | 淮安万邦香料工业有限公司 | 一种龙涎酮的制备方法 |
CN103265419A (zh) * | 2013-05-22 | 2013-08-28 | 安徽省三环纸业集团香料科技发展有限公司 | 一种龙涎酮的制备方法 |
CN103804160A (zh) * | 2014-01-27 | 2014-05-21 | 南京运华立太能源科技有限公司 | 3-甲基-3-戊烯-2-酮的制备方法 |
WO2022214180A1 (en) | 2021-04-08 | 2022-10-13 | Symrise Ag | Sustainable process for the preparation of 5-methylhept-2-en-4-one |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3345784A1 (de) * | 1983-12-17 | 1985-06-27 | Haarmann & Reimer Gmbh, 3450 Holzminden | Verwendung von 5-methyl-2-hepten-4-on als riech- und/oder aromastoff sowie diesen stoff enthaltende riech- und/oder aromastoffkompositionen |
CN1198432A (zh) * | 1997-05-05 | 1998-11-11 | 中国轻工总会香科研究所 | 坚果型香料5-甲基-2-庚烯-4-酮的合成方法 |
-
2008
- 2008-06-03 CN CN200810123410XA patent/CN101597223B/zh active Active
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102030626A (zh) * | 2010-11-16 | 2011-04-27 | 上海应用技术学院 | 一种5-甲基-2-庚烯-4-酮的制备方法 |
CN102030626B (zh) * | 2010-11-16 | 2013-02-20 | 上海应用技术学院 | 一种5-甲基-2-庚烯-4-酮的制备方法 |
CN103058842A (zh) * | 2012-12-26 | 2013-04-24 | 淮安万邦香料工业有限公司 | 一种龙涎酮的制备方法 |
CN103058842B (zh) * | 2012-12-26 | 2014-10-15 | 淮安万邦香料工业有限公司 | 一种龙涎酮的制备方法 |
CN103265419A (zh) * | 2013-05-22 | 2013-08-28 | 安徽省三环纸业集团香料科技发展有限公司 | 一种龙涎酮的制备方法 |
CN103265419B (zh) * | 2013-05-22 | 2015-05-20 | 安徽省三环纸业集团香料科技发展有限公司 | 一种龙涎酮的制备方法 |
CN103804160A (zh) * | 2014-01-27 | 2014-05-21 | 南京运华立太能源科技有限公司 | 3-甲基-3-戊烯-2-酮的制备方法 |
CN103804160B (zh) * | 2014-01-27 | 2016-03-02 | 南京运华立太能源科技有限公司 | 3-甲基-3-戊烯-2-酮的制备方法 |
WO2022214180A1 (en) | 2021-04-08 | 2022-10-13 | Symrise Ag | Sustainable process for the preparation of 5-methylhept-2-en-4-one |
Also Published As
Publication number | Publication date |
---|---|
CN101597223B (zh) | 2012-07-04 |
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Effective date of registration: 20120906 Address after: 245200 Anhui Province, Huangshan City Shexian Fu e Industrial Park Patentee after: Huangshan Kehong Technology Development Co.,Ltd. Address before: 245202 Anhui province Huangshan City Shexian Fu Road, No. 1 e Zhen Patentee before: Cheng Cunzhao |
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CP01 | Change in the name or title of a patent holder |
Address after: 245200 Anhui Province, Huangshan City Shexian Fu e Industrial Park Patentee after: HUANGSHAN KEHONG BIO-FLAVORS CO.,LTD. Address before: 245200 Anhui Province, Huangshan City Shexian Fu e Industrial Park Patentee before: Huangshan Kehong Technology Development Co.,Ltd. |
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Address after: 245200 Fuzhi Industrial Park, She County, Mount Huangshan City, Anhui Province Patentee after: Mount Huangshan Kehong Biotechnology Co.,Ltd. Address before: 245200 Fuzhi Industrial Park, She County, Mount Huangshan City, Anhui Province Patentee before: HUANGSHAN KEHONG BIO-FLAVORS CO.,LTD. |
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