CZ2017491A3 - Způsob odstranění acylderivátů monochlorpropandiolu a glycidolu z plně ztužených tuků určených pro potravinářské účely - Google Patents
Způsob odstranění acylderivátů monochlorpropandiolu a glycidolu z plně ztužených tuků určených pro potravinářské účely Download PDFInfo
- Publication number
- CZ2017491A3 CZ2017491A3 CZ2017-491A CZ2017491A CZ2017491A3 CZ 2017491 A3 CZ2017491 A3 CZ 2017491A3 CZ 2017491 A CZ2017491 A CZ 2017491A CZ 2017491 A3 CZ2017491 A3 CZ 2017491A3
- Authority
- CZ
- Czechia
- Prior art keywords
- glycidol
- mcpd
- nickel
- catalyst
- acyl derivatives
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- 125000002252 acyl group Chemical group 0.000 title claims abstract description 9
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 title description 26
- 239000003925 fat Substances 0.000 title description 7
- 235000013305 food Nutrition 0.000 title description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 46
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 14
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims description 30
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000007868 Raney catalyst Substances 0.000 claims description 12
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 12
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 11
- 239000008158 vegetable oil Substances 0.000 claims description 11
- 229910052759 nickel Inorganic materials 0.000 claims description 9
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- DYPJJAAKPQKWTM-UHFFFAOYSA-N 2-chloropropane-1,3-diol Chemical compound OCC(Cl)CO DYPJJAAKPQKWTM-UHFFFAOYSA-N 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 claims description 3
- ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 2,3-dichloropropan-1-ol Chemical compound OCC(Cl)CCl ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 0.000 claims description 3
- HZPNKQREYVVATQ-UHFFFAOYSA-L nickel(2+);diformate Chemical compound [Ni+2].[O-]C=O.[O-]C=O HZPNKQREYVVATQ-UHFFFAOYSA-L 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 12
- XEPXTKKIWBPAEG-UHFFFAOYSA-N 1,1-dichloropropan-1-ol Chemical class CCC(O)(Cl)Cl XEPXTKKIWBPAEG-UHFFFAOYSA-N 0.000 abstract description 2
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 235000021588 free fatty acids Nutrition 0.000 description 9
- 239000002540 palm oil Substances 0.000 description 9
- 238000007670 refining Methods 0.000 description 9
- 235000019482 Palm oil Nutrition 0.000 description 8
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001982 diacylglycerols Chemical class 0.000 description 6
- 150000002759 monoacylglycerols Chemical class 0.000 description 5
- 239000004006 olive oil Substances 0.000 description 5
- 240000002791 Brassica napus Species 0.000 description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 244000020551 Helianthus annuus Species 0.000 description 4
- 235000003222 Helianthus annuus Nutrition 0.000 description 4
- 238000004061 bleaching Methods 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- 240000007817 Olea europaea Species 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 239000010464 refined olive oil Substances 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 238000007171 acid catalysis Methods 0.000 description 2
- 230000000711 cancerogenic effect Effects 0.000 description 2
- 231100000315 carcinogenic Toxicity 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- -1 triacylglycerol fatty acids Chemical class 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 235000019871 vegetable fat Nutrition 0.000 description 2
- HUXDTFZDCPYTCF-UHFFFAOYSA-N 1-chloropropane-1,1-diol Chemical compound CCC(O)(O)Cl HUXDTFZDCPYTCF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 239000004146 Propane-1,2-diol Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 description 1
- 235000005473 carotenes Nutrition 0.000 description 1
- 150000001746 carotenes Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- 239000001752 chlorophylls and chlorophyllins Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000105 evaporative light scattering detection Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 231100000024 genotoxic Toxicity 0.000 description 1
- 230000001738 genotoxic effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000003244 pro-oxidative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 235000008210 xanthophylls Nutrition 0.000 description 1
- 150000003735 xanthophylls Chemical class 0.000 description 1
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- Fats And Perfumes (AREA)
- Catalysts (AREA)
Abstract
Vynález se týká způsobu odstranění chlorovaných sloučenin a epoxidů, zejména acylderivátů monochlorpropandiolů (MCPD), dichlorpropanolů (DCP) a glycidyl esterů, modifikací procesu totální hydrogenace tak, že se po ukončení hydrogenace do hydrogenovaného tuku použije katalyzátor na bázi niklu.
Claims (2)
- PATENTOVÉ NÁROKYZpůsob odstranění vzniku chlorovaných derivátů, zejména acylderivátů 3-monochlorpropan-l,2-diolu (3-MCPD), 2-monochlorpropan-l,3-diolu
- (2-MCPD), 2,3-dichlorpropan-l-olu (2,3-DCP), l,3-dichlorpropan-2-olu (1,3-DCP) a glycidyl esterů úpravou procesu totální hydrogenace (120 až^220 °C, 1 6 h) rostlinných olejů průmyslovým katalyzátorem^-který^ě vyznačuje tím, že sft po ukončení hydrogenacyttonydrogenovaného tuku přidá 0,05 až 5 hmf % katalyzátoru na bázi niklu, a to zejména Raneyův nikl nebo Raneyův nikl připravený podle Urushibary nebo fosfidy nebo boridy nebo sulfidy niklu nebo nikl připravený zmravenčanu nikelnatého a nebo jejich směsi/a reakční směs se dále za průtoku vodíku míchá a zahřívá na teplotu 80 až 280 °C po dobu 0,1 až 6 h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ2017-491A CZ2017491A3 (cs) | 2017-08-25 | 2017-08-25 | Způsob odstranění acylderivátů monochlorpropandiolu a glycidolu z plně ztužených tuků určených pro potravinářské účely |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ2017-491A CZ2017491A3 (cs) | 2017-08-25 | 2017-08-25 | Způsob odstranění acylderivátů monochlorpropandiolu a glycidolu z plně ztužených tuků určených pro potravinářské účely |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ307495B6 CZ307495B6 (cs) | 2018-10-17 |
| CZ2017491A3 true CZ2017491A3 (cs) | 2018-10-17 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ2017-491A CZ2017491A3 (cs) | 2017-08-25 | 2017-08-25 | Způsob odstranění acylderivátů monochlorpropandiolu a glycidolu z plně ztužených tuků určených pro potravinářské účely |
Country Status (1)
| Country | Link |
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| CZ (1) | CZ2017491A3 (cs) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102334563B (zh) * | 2010-07-16 | 2015-03-25 | 丰益(上海)生物技术研发中心有限公司 | 控制油脂中3-氯-1,2-丙二醇或其酯含量的方法 |
| NO2611767T3 (cs) * | 2010-09-03 | 2018-03-24 | ||
| WO2014012548A1 (en) * | 2012-07-18 | 2014-01-23 | Aarhuskarlshamn Ab | Reduction of mcpd-compounds in refined plant oil for food |
| CN105802731B (zh) * | 2016-06-03 | 2019-11-01 | 上海交通大学 | 一种除去3-氯丙二醇酯的方法 |
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- 2017-08-25 CZ CZ2017-491A patent/CZ2017491A3/cs unknown
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| Publication number | Publication date |
|---|---|
| CZ307495B6 (cs) | 2018-10-17 |
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