JPH0346458B2 - - Google Patents
Info
- Publication number
- JPH0346458B2 JPH0346458B2 JP57225042A JP22504282A JPH0346458B2 JP H0346458 B2 JPH0346458 B2 JP H0346458B2 JP 57225042 A JP57225042 A JP 57225042A JP 22504282 A JP22504282 A JP 22504282A JP H0346458 B2 JPH0346458 B2 JP H0346458B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- formula
- fatty acids
- decalactone
- unsaturated fatty
- 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.)
- Expired - Lifetime
Links
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 8
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 8
- 239000003377 acid catalyst Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000002596 lactones Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 9
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-UHFFFAOYSA-N 0.000 description 8
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 4
- YKVIWISPFDZYOW-UHFFFAOYSA-N 6-Decanolide Chemical compound CCCCC1CCCCC(=O)O1 YKVIWISPFDZYOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000001730 (5R)-5-butyloxolan-2-one Substances 0.000 description 2
- UJUXUEKQHBXUEM-AATRIKPKSA-N 5-Decenoic acid Chemical compound CCCC\C=C\CCCC(O)=O UJUXUEKQHBXUEM-AATRIKPKSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- IPBFYZQJXZJBFQ-UHFFFAOYSA-N gamma-octalactone Chemical compound CCCCC1CCC(=O)O1 IPBFYZQJXZJBFQ-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- XKZKQTCECFWKBN-VOTSOKGWSA-N (e)-dec-4-enoic acid Chemical compound CCCCC\C=C\CCC(O)=O XKZKQTCECFWKBN-VOTSOKGWSA-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- -1 boric acid Chemical compound 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
- 244000309464 bull Species 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- IZOFWCYKCWUJBY-UHFFFAOYSA-N dec-6-enoic acid Chemical class CCCC=CCCCCC(O)=O IZOFWCYKCWUJBY-UHFFFAOYSA-N 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
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 239000007791 liquid phase 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
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 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
- WXBXVVIUZANZAU-CMDGGOBGSA-N trans-2-decenoic acid Chemical compound CCCCCCC\C=C\C(O)=O WXBXVVIUZANZAU-CMDGGOBGSA-N 0.000 description 1
- RRGOKSYVAZDNKR-ONEGZZNKSA-N trans-delta-octenoic acid Chemical compound CC\C=C\CCCC(O)=O RRGOKSYVAZDNKR-ONEGZZNKSA-N 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 JPS59116247A (ja) | 1984-07-05 |
| JPH0346458B2 true 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) |
Families Citing this family (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 |
| JP4775780B2 (ja) * | 2001-07-25 | 2011-09-21 | 曽田香料株式会社 | 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 |
| CN103588633B (zh) * | 2013-11-22 | 2015-08-05 | 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 |
-
1982
- 1982-12-23 JP JP57225042A patent/JPS59116247A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| JOURNAL OF ORGANIC CHEMISTRG=1977 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59116247A (ja) | 1984-07-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0357905B2 (en, 2012) | ||
| JPH0346458B2 (en, 2012) | ||
| US4156093A (en) | Process for increasing the production or recovery yields of hemiacetal-esters of glyoxylic acid | |
| CA1077959A (en) | Pyrolysis of limonene-1,2-dialkanoates to give perillyl alkanoates | |
| Harada et al. | A convenient synthesis of 2-deoxy-D-ribose | |
| US2508279A (en) | Method of preparing acrylamide | |
| US2451740A (en) | Process for the manufacture of an aldehyde | |
| EP0010859B1 (en) | Process for the preparation of cyclopropane carboxylic acid esters | |
| EP0002297B1 (en) | Process for the preparation of dl-phenyl-glycine amide | |
| US2901506A (en) | Pyrolysis of substituted carbonyloxyalkyl halides | |
| US4283339A (en) | Preparation of dioxane and co-products | |
| JPH0475224B2 (en, 2012) | ||
| US2772295A (en) | Process of manufacturing esters of 3-substituted 2-furoic acids | |
| EP0025638B1 (en) | Process for the production of 1-crotonoyl-2,6,6-trimethylcyclohexa-1,3-diene and esters of alkynylcyclohexane derivatives as intermediates therefor | |
| US4276218A (en) | Preparation of dihalogenovinyl-γ-butyrolactones | |
| JPH08119924A (ja) | ３，７−ジメチル−２，６−オクタジエンニトリルの異性化方法 | |
| CN1030414A (zh) | 新的噻吩化合物及其制备 | |
| US2451857A (en) | Separation of capryl alcohol from methyl hexyl ketone by alkali treatment and distillation | |
| JPS6287550A (ja) | Ｚ−２−メチル−２−ブテン酸の製造方法 | |
| JP3051567B2 (ja) | 環式ラクトンの新規誘導体、その製法及び１５−ペンタデカノライドとその同族体の製法 | |
| JP2513258B2 (ja) | 新規なα，β−不飽和ケトン化合物 | |
| US3259648A (en) | Cyclohexylmethyl cinnamate | |
| US2577418A (en) | Tall oil-melamine reaction product | |
| KR870001042B1 (ko) | 분지상 알카노인산의 제조방법 | |
| SU810695A1 (ru) | Способ получени 1,3-диоксанонов-4 |