JPH0753874B2 - パーム核油脂肪酸アルキルエステルの安定化方法 - Google Patents
パーム核油脂肪酸アルキルエステルの安定化方法Info
- Publication number
- JPH0753874B2 JPH0753874B2 JP61006135A JP613586A JPH0753874B2 JP H0753874 B2 JPH0753874 B2 JP H0753874B2 JP 61006135 A JP61006135 A JP 61006135A JP 613586 A JP613586 A JP 613586A JP H0753874 B2 JPH0753874 B2 JP H0753874B2
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- palm kernel
- kernel oil
- oil fatty
- methyl ester
- 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
- 239000003346 palm kernel oil Substances 0.000 title claims description 48
- 235000019865 palm kernel oil Nutrition 0.000 title claims description 48
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 37
- 229930195729 fatty acid Natural products 0.000 title claims description 37
- 239000000194 fatty acid Substances 0.000 title claims description 37
- 238000000034 method Methods 0.000 title description 7
- 230000000087 stabilizing effect Effects 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 22
- 150000004665 fatty acids Chemical class 0.000 claims description 20
- 239000003381 stabilizer Substances 0.000 claims description 13
- 150000004702 methyl esters Chemical class 0.000 claims description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004492 methyl ester group Chemical group 0.000 claims 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000007795 chemical reaction product Substances 0.000 description 13
- 235000019482 Palm oil Nutrition 0.000 description 12
- 239000002540 palm oil Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 10
- OKLNGCVEHOKJIY-UHFFFAOYSA-N 3-butyl-4-methylphenol Chemical compound CCCCC1=CC(O)=CC=C1C OKLNGCVEHOKJIY-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000003240 coconut oil Substances 0.000 description 6
- 235000019864 coconut oil Nutrition 0.000 description 6
- -1 fatty acid esters Chemical class 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000013065 commercial product Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
- 235000019345 sodium thiosulphate Nutrition 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
- 229940043253 butylated hydroxyanisole Drugs 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000010388 propyl gallate Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000010384 tocopherol Nutrition 0.000 description 2
- 239000011732 tocopherol Substances 0.000 description 2
- 229930003799 tocopherol Natural products 0.000 description 2
- 229960001295 tocopherol Drugs 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- OTJFQRMIRKXXRS-UHFFFAOYSA-N (hydroxymethylamino)methanol Chemical compound OCNCO OTJFQRMIRKXXRS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
- 235000000072 L-ascorbyl-6-palmitate Nutrition 0.000 description 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- 229940064063 alpha tocotrienol Drugs 0.000 description 1
- RZFHLOLGZPDCHJ-DLQZEEBKSA-N alpha-Tocotrienol Natural products Oc1c(C)c(C)c2O[C@@](CC/C=C(/CC/C=C(\CC/C=C(\C)/C)/C)\C)(C)CCc2c1C RZFHLOLGZPDCHJ-DLQZEEBKSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000012993 chemical processing Methods 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 235000010382 gamma-tocopherol Nutrition 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229940097411 palm acid Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- RZFHLOLGZPDCHJ-XZXLULOTSA-N α-Tocotrienol Chemical compound OC1=C(C)C(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C RZFHLOLGZPDCHJ-XZXLULOTSA-N 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 239000011730 α-tocotrienol Substances 0.000 description 1
- 235000019145 α-tocotrienol Nutrition 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
- C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3500938.1 | 1985-01-14 | ||
| DE19853500938 DE3500938A1 (de) | 1985-01-14 | 1985-01-14 | Stabilisierung von palmkernoel und palmkernfettsaeurealkylestern fuer deren verarbeitung zu farbneutralen reaktionsfolgeprodukten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61163999A JPS61163999A (ja) | 1986-07-24 |
| JPH0753874B2 true JPH0753874B2 (ja) | 1995-06-07 |
Family
ID=6259752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61006135A Expired - Lifetime JPH0753874B2 (ja) | 1985-01-14 | 1986-01-14 | パーム核油脂肪酸アルキルエステルの安定化方法 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0189049B2 (OSRAM) |
| JP (1) | JPH0753874B2 (OSRAM) |
| BR (1) | BR8600103A (OSRAM) |
| DE (2) | DE3500938A1 (OSRAM) |
| GB (1) | GB2169611B (OSRAM) |
| MY (1) | MY102435A (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE980887A1 (en) * | 1998-10-27 | 2000-05-03 | Diarmaid Joseph Long | Anti-oxidant formulations |
| DE102005015474A1 (de) | 2005-04-04 | 2006-10-05 | Degussa Ag | Verfahren zur Erhöhung der Oxidationsstabilität von Biodiesel |
| WO2009108747A1 (en) * | 2008-02-27 | 2009-09-03 | Wayne State University | The effect of natural and synthetic antioxidants on the oxidative stability of biodiesel |
| US20120233912A1 (en) | 2011-03-18 | 2012-09-20 | Otkrytoe Aktsionernoe Obschestvo "Sterlitamaxky Neftekhimichesky Zavod" | Antioxidant additive composition, a solution thereof, and a method for improving the storage stability of biodiesel fuel (variants) |
| CN104024355A (zh) * | 2011-11-16 | 2014-09-03 | 泰克尼克斯工业有限公司 | 沥青稀释剂 |
| RU2476585C1 (ru) | 2012-03-07 | 2013-02-27 | Открытое Акционерное Общество "Стерлитамакский Нефтехимический Завод" | Композиция антиокислительной присадки, ее раствор и способ повышения стабильности биодизельного топлива при хранении (варианты) |
| AU2022233124A1 (en) | 2021-03-08 | 2023-09-21 | Technix EnviroCutter IP Limited | Bitumen cutback compositions and methods of use thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB754388A (en) * | 1954-04-02 | 1956-08-08 | Alfred William Brickman | Improvements in the inhibition of oxidation of fats or fatty oils |
| JPS5373206A (en) * | 1976-12-10 | 1978-06-29 | Riken Vitamin Co Ltd | Antioxidant composition for fat and oil |
| JPS5554400A (en) * | 1978-10-17 | 1980-04-21 | Nisshin Oil Mills Ltd | Manufacture of high antiioxidability fat and oil |
| JPS5944344B2 (ja) * | 1978-11-17 | 1984-10-29 | 田辺製薬株式会社 | 抗酸化剤 |
| JPS6042495A (ja) * | 1983-08-17 | 1985-03-06 | 日清製油株式会社 | 油脂脱臭留出物のメチルエステル化法 |
-
1985
- 1985-01-14 DE DE19853500938 patent/DE3500938A1/de active Granted
-
1986
- 1986-01-02 GB GB8600027A patent/GB2169611B/en not_active Expired
- 1986-01-07 EP EP86100134A patent/EP0189049B2/de not_active Expired - Lifetime
- 1986-01-07 DE DE8686100134T patent/DE3673027D1/de not_active Expired - Lifetime
- 1986-01-13 BR BR8600103A patent/BR8600103A/pt unknown
- 1986-01-14 JP JP61006135A patent/JPH0753874B2/ja not_active Expired - Lifetime
-
1987
- 1987-04-18 MY MYPI87000504A patent/MY102435A/en unknown
Non-Patent Citations (1)
| Title |
|---|
| 油化学第２８巻第１０号（１９７９），Ｐ．７４７〜７５９ |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2169611A (en) | 1986-07-16 |
| DE3500938C2 (OSRAM) | 1993-06-24 |
| EP0189049B1 (de) | 1990-08-01 |
| GB8600027D0 (en) | 1986-02-12 |
| GB2169611B (en) | 1989-09-13 |
| DE3673027D1 (de) | 1990-09-06 |
| BR8600103A (pt) | 1986-09-23 |
| MY102435A (en) | 1992-06-30 |
| DE3500938A1 (de) | 1986-07-17 |
| JPS61163999A (ja) | 1986-07-24 |
| EP0189049B2 (de) | 1993-12-15 |
| EP0189049A1 (de) | 1986-07-30 |
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| EXPY | Cancellation because of completion of term |