JPS59116247A - 不飽和脂肪酸の製法 - Google Patents
不飽和脂肪酸の製法Info
- Publication number
- JPS59116247A JPS59116247A JP57225042A JP22504282A JPS59116247A JP S59116247 A JPS59116247 A JP S59116247A JP 57225042 A JP57225042 A JP 57225042A JP 22504282 A JP22504282 A JP 22504282A JP S59116247 A JPS59116247 A JP S59116247A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- lactone
- formula
- unsaturated fatty
- acid catalyst
- 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
- 150000004670 unsaturated fatty acids Chemical class 0.000 title claims abstract description 11
- 235000021122 unsaturated fatty acids Nutrition 0.000 title claims abstract description 11
- 150000002596 lactones Chemical class 0.000 claims abstract description 13
- 239000003377 acid catalyst Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract 3
- 238000004519 manufacturing process Methods 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract description 4
- WXBXVVIUZANZAU-CMDGGOBGSA-N trans-2-decenoic acid Chemical compound CCCCCCC\C=C\C(O)=O WXBXVVIUZANZAU-CMDGGOBGSA-N 0.000 abstract description 4
- 239000004927 clay Substances 0.000 abstract description 3
- 235000013305 food Nutrition 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 abstract description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- YKVIWISPFDZYOW-UHFFFAOYSA-N 6-Decanolide Chemical compound CCCCC1CCCCC(=O)O1 YKVIWISPFDZYOW-UHFFFAOYSA-N 0.000 abstract 1
- -1 epsilon-decalactone Chemical class 0.000 abstract 1
- 235000013599 spices Nutrition 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 12
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 2
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000001730 (5R)-5-butyloxolan-2-one Substances 0.000 description 1
- XKZKQTCECFWKBN-VOTSOKGWSA-N (e)-dec-4-enoic acid Chemical compound CCCCC\C=C\CCC(O)=O XKZKQTCECFWKBN-VOTSOKGWSA-N 0.000 description 1
- WXBXVVIUZANZAU-UHFFFAOYSA-N 2E-decenoic acid Natural products CCCCCCCC=CC(O)=O WXBXVVIUZANZAU-UHFFFAOYSA-N 0.000 description 1
- CSOUQUGRHLZMKD-UHFFFAOYSA-N 3-[2-[4-[(2-chloro-4-nitrophenyl)diazenyl]phenyl]ethylamino]propanenitrile Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1N=NC1=CC=C(CCNCCC#N)C=C1 CSOUQUGRHLZMKD-UHFFFAOYSA-N 0.000 description 1
- UJUXUEKQHBXUEM-AATRIKPKSA-N 5-Decenoic acid Chemical compound CCCC\C=C\CCCC(O)=O UJUXUEKQHBXUEM-AATRIKPKSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007269 dehydrobromination reaction Methods 0.000 description 1
- FYTRVXSHONWYNE-UHFFFAOYSA-N delta-octanolide Chemical compound CCCC1CCCC(=O)O1 FYTRVXSHONWYNE-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- IPBFYZQJXZJBFQ-UHFFFAOYSA-N gamma-octalactone Chemical compound CCCCC1CCC(=O)O1 IPBFYZQJXZJBFQ-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- OTJVLQGVNKNLCB-NSCUHMNNSA-N trans-epsilon-octenoic acid Chemical compound C\C=C\CCCCC(O)=O OTJVLQGVNKNLCB-NSCUHMNNSA-N 0.000 description 1
Classifications
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57225042A JPS59116247A (ja) | 1982-12-23 | 1982-12-23 | 不飽和脂肪酸の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57225042A JPS59116247A (ja) | 1982-12-23 | 1982-12-23 | 不飽和脂肪酸の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59116247A true JPS59116247A (ja) | 1984-07-05 |
| JPH0346458B2 JPH0346458B2 (en, 2012) | 1991-07-16 |
Family
ID=16823127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57225042A Granted JPS59116247A (ja) | 1982-12-23 | 1982-12-23 | 不飽和脂肪酸の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59116247A (en, 2012) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002100989A1 (fr) * | 2001-06-08 | 2002-12-19 | Soda Aromatic Co.,Ltd | Composition de parfum et procede de production afferent |
| JP2003041287A (ja) * | 2001-07-25 | 2003-02-13 | Soda Aromatic Co Ltd | 耐熱性香料組成物 |
| JP2007161655A (ja) * | 2005-12-15 | 2007-06-28 | Soda Aromatic Co Ltd | 不飽和脂肪酸の製造方法 |
| CN103588633A (zh) * | 2013-11-22 | 2014-02-19 | 浙江安赛生物科技有限公司 | 5(6)-癸烯酸的制备工艺 |
| JP2014519476A (ja) * | 2011-03-28 | 2014-08-14 | エージェンシー フォー サイエンス，テクノロジー アンド リサーチ | 二価酸の合成 |
| CN110143866A (zh) * | 2019-06-12 | 2019-08-20 | 广东广益科技实业有限公司 | 5(6)-癸烯酸的合成方法 |
-
1982
- 1982-12-23 JP JP57225042A patent/JPS59116247A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| JOURNAL OF ORGANIC CHEMISTRG=1977 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002100989A1 (fr) * | 2001-06-08 | 2002-12-19 | Soda Aromatic Co.,Ltd | Composition de parfum et procede de production afferent |
| US7252849B2 (en) | 2001-06-08 | 2007-08-07 | Soda Aromatic Co., Ltd. | Perfume composition and process for producing the same |
| JP2003041287A (ja) * | 2001-07-25 | 2003-02-13 | Soda Aromatic Co Ltd | 耐熱性香料組成物 |
| JP2007161655A (ja) * | 2005-12-15 | 2007-06-28 | Soda Aromatic Co Ltd | 不飽和脂肪酸の製造方法 |
| JP2014519476A (ja) * | 2011-03-28 | 2014-08-14 | エージェンシー フォー サイエンス，テクノロジー アンド リサーチ | 二価酸の合成 |
| EP2691361A4 (en) * | 2011-03-28 | 2014-09-17 | Agency Science Tech & Res | SYNTHESIS OF DIAZIDEN |
| CN103588633A (zh) * | 2013-11-22 | 2014-02-19 | 浙江安赛生物科技有限公司 | 5(6)-癸烯酸的制备工艺 |
| CN110143866A (zh) * | 2019-06-12 | 2019-08-20 | 广东广益科技实业有限公司 | 5(6)-癸烯酸的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0346458B2 (en, 2012) | 1991-07-16 |
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