JPH0118912B2 - - Google Patents
Info
- Publication number
- JPH0118912B2 JPH0118912B2 JP9067680A JP9067680A JPH0118912B2 JP H0118912 B2 JPH0118912 B2 JP H0118912B2 JP 9067680 A JP9067680 A JP 9067680A JP 9067680 A JP9067680 A JP 9067680A JP H0118912 B2 JPH0118912 B2 JP H0118912B2
- Authority
- JP
- Japan
- Prior art keywords
- distillate
- distillation
- deodorizing
- deodorized distillate
- tocopherols
- 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
Links
- 229930003799 tocopherol Natural products 0.000 claims description 26
- 239000011732 tocopherol Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 19
- 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 claims description 17
- 238000004821 distillation Methods 0.000 claims description 16
- 235000010384 tocopherol Nutrition 0.000 claims description 15
- 229960001295 tocopherol Drugs 0.000 claims description 15
- 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 claims description 15
- 230000001877 deodorizing effect Effects 0.000 claims description 14
- 239000012141 concentrate Substances 0.000 claims description 12
- 235000021588 free fatty acids Nutrition 0.000 claims description 12
- 239000003921 oil Substances 0.000 claims description 5
- 239000003925 fat Substances 0.000 claims description 4
- 150000005846 sugar alcohols Polymers 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 description 12
- 235000019149 tocopherols Nutrition 0.000 description 11
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 11
- 238000005886 esterification reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 238000001256 steam distillation Methods 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 235000012343 cottonseed oil Nutrition 0.000 description 6
- 239000002385 cottonseed oil Substances 0.000 description 6
- 239000003549 soybean oil Substances 0.000 description 6
- 235000012424 soybean oil Nutrition 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 235000019484 Rapeseed oil Nutrition 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000000199 molecular distillation Methods 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 235000019774 Rice Bran oil Nutrition 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000010389 delta-tocopherol Nutrition 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000008165 rice bran oil Substances 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 229930193551 sterin Natural products 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003789 δ-tocopherols Chemical class 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 210000002196 fr. b Anatomy 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 238000005194 fractionation Methods 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
- 125000005456 glyceride group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9067680A JPS5716878A (en) | 1980-07-04 | 1980-07-04 | Production of tocopherol concentrate |
DE19813126110 DE3126110A1 (de) | 1980-07-04 | 1981-07-02 | Verfahren zur gewinnung von tocopherol-konzentraten |
US06/279,650 US4454329A (en) | 1980-07-04 | 1981-07-02 | Process for preparation of tocopherol concentrates |
CH438881A CH651831A5 (en) | 1980-07-04 | 1981-07-03 | Process for the preparation of tocopherol concentrates |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP9067680A JPS5716878A (en) | 1980-07-04 | 1980-07-04 | Production of tocopherol concentrate |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5716878A JPS5716878A (en) | 1982-01-28 |
JPH0118912B2 true JPH0118912B2 (xx) | 1989-04-07 |
Family
ID=14005135
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP9067680A Granted JPS5716878A (en) | 1980-07-04 | 1980-07-04 | Production of tocopherol concentrate |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5716878A (xx) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PL2502503T3 (pl) * | 2011-03-24 | 2015-05-29 | Loders Croklaan Bv | Sposób frakcjonowania oleju roślinnego |
JP5808479B2 (ja) * | 2011-04-14 | 2015-11-10 | アルファ−ラヴァル・コーポレート・アーベー | 脂肪酸の自己触媒エステル化のための方法 |
CN115747266B (zh) * | 2023-01-05 | 2023-05-12 | 苏州丰倍生物科技股份有限公司 | 一种脂肪酶催化生产脂肪酸甲酯的方法 |
-
1980
- 1980-07-04 JP JP9067680A patent/JPS5716878A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5716878A (en) | 1982-01-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP3746292B2 (ja) | トコフェロールおよびステロールの回収 | |
EP1894913A1 (en) | Production of esters of fatty acids and lower alcohols | |
US20110220483A1 (en) | Process for the extraction of squalene, sterols and vitamin e contained in condensates of physical refining and/or in distillates of deodorization of plant oils | |
EP2819990B1 (en) | Method for producing an esterified polyol | |
US6815551B2 (en) | Processes for concentrating tocopherols and/or sterols | |
US4454329A (en) | Process for preparation of tocopherol concentrates | |
EP1440138A1 (en) | Method for fractionating grease trap waste and uses of fractions therefrom | |
JP2007176973A (ja) | 軽油代替燃料用の脂肪酸低級アルキルエステルの製造方法 | |
MXPA04002116A (es) | Metodos para tratamiento de destilado desodorizante. | |
US8440847B2 (en) | Method of converting free fatty acid (FFA) from oil to methyl ester | |
EP1892232A1 (en) | Production of esters of fatty acids and lower alcohols | |
JP4180052B2 (ja) | 植物油の精製の副生物から植物ステロールを回収する方法 | |
WO2006129435A1 (ja) | 脂肪酸低級アルキルエステルの製造方法および脂肪酸低級アルキルエステルならびに軽油代替燃料 | |
JPWO2006016492A1 (ja) | バイオディーゼル燃料用組成物の製造方法およびバイオディーゼル燃料製造装置 | |
JPH0118912B2 (xx) | ||
US6187974B1 (en) | Process for producing unsaturated fatty alcohols from lauric oils | |
JPS62209029A (ja) | ヘキサメチルテトラコサン類の製造法 | |
JP4335306B2 (ja) | 油脂のエステル交換方法 | |
US2460796A (en) | Process for preparing carotenoid concentrates from palm oil | |
JP6426192B2 (ja) | トリテルペンエステルの濃縮 | |
EP1226157B1 (en) | Process for the purification of phytosterol from fatty acids and their esters | |
JP4943001B2 (ja) | トコトリエノール類含有組成物の製造方法 | |
JP5005547B2 (ja) | 脂肪酸低級アルキルエステルの製造方法 | |
Torres et al. | Extraction and enzymatic modification of functional lipids from soybean oil deodorizer distillate | |
GB2148897A (en) | Catalytic esterification of carboxylic acid/glyceride mixtures |