CN103436360B - 甘油酯组合物的制备方法 - Google Patents
甘油酯组合物的制备方法 Download PDFInfo
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- CN103436360B CN103436360B CN201310226777.5A CN201310226777A CN103436360B CN 103436360 B CN103436360 B CN 103436360B CN 201310226777 A CN201310226777 A CN 201310226777A CN 103436360 B CN103436360 B CN 103436360B
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- fatty acid
- acid ester
- glyceride composition
- composition
- racemic glycidol
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- 239000000203 mixture Substances 0.000 title claims abstract description 241
- 125000005456 glyceride group Chemical group 0.000 title claims abstract description 174
- 238000004519 manufacturing process Methods 0.000 title abstract 4
- -1 fatty acid ester Chemical class 0.000 claims abstract description 189
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 140
- 239000000194 fatty acid Substances 0.000 claims abstract description 140
- 229930195729 fatty acid Natural products 0.000 claims abstract description 140
- 238000000034 method Methods 0.000 claims abstract description 109
- 238000004332 deodorization Methods 0.000 claims abstract description 59
- 239000002253 acid Substances 0.000 claims abstract description 58
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 10
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 102
- 238000002360 preparation method Methods 0.000 claims description 32
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 24
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 17
- 239000011707 mineral Substances 0.000 claims description 17
- 230000004913 activation Effects 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 16
- 150000001875 compounds Chemical class 0.000 abstract description 12
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract 3
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- 239000002994 raw material Substances 0.000 description 49
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 45
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- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 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 3
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
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- 238000007796 conventional method Methods 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 229960004232 linoleic acid Drugs 0.000 description 3
- 229960004488 linolenic acid Drugs 0.000 description 3
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000003822 preparative gas chromatography Methods 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- LGRRXTJABQMXHY-UHFFFAOYSA-N 1-chlorohenicosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCl LGRRXTJABQMXHY-UHFFFAOYSA-N 0.000 description 2
- SSZWWUDQMAHNAQ-UXXIZXEISA-N 3-chloro-1,1,2,3,3-pentadeuteriopropane-1,2-diol Chemical compound [2H]C([2H])(O)C([2H])(O)C([2H])([2H])Cl SSZWWUDQMAHNAQ-UXXIZXEISA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- OUQGOXCIUOCDNN-UHFFFAOYSA-N Glycidyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC1CO1 OUQGOXCIUOCDNN-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 2
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 230000003311 flocculating effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000005908 glyceryl ester group Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
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- 238000010561 standard procedure Methods 0.000 description 2
- 125000005457 triglyceride group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
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- 235000019483 Peanut oil Nutrition 0.000 description 1
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- 244000124853 Perilla frutescens Species 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- ATBOMIWRCZXYSZ-XZBBILGWSA-N [1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC ATBOMIWRCZXYSZ-XZBBILGWSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
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- 229910021383 artificial graphite Inorganic materials 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
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- 239000006229 carbon black Substances 0.000 description 1
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- 239000012159 carrier gas Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
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- 150000004292 cyclic ethers Chemical class 0.000 description 1
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
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- 239000008268 mayonnaise Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
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- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical class CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 229960002969 oleic acid Drugs 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
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- 229960004274 stearic acid Drugs 0.000 description 1
- 239000010496 thistle oil Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
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Landscapes
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009206504 | 2009-09-07 | ||
| JP2009-206504 | 2009-09-07 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201010277986.9A Division CN102010786B (zh) | 2009-09-07 | 2010-09-03 | 甘油酯组合物及其制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103436360A CN103436360A (zh) | 2013-12-11 |
| CN103436360B true CN103436360B (zh) | 2015-04-22 |
Family
ID=43841119
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310226777.5A Active CN103436360B (zh) | 2009-09-07 | 2010-09-03 | 甘油酯组合物的制备方法 |
| CN201010277986.9A Active CN102010786B (zh) | 2009-09-07 | 2010-09-03 | 甘油酯组合物及其制备方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201010277986.9A Active CN102010786B (zh) | 2009-09-07 | 2010-09-03 | 甘油酯组合物及其制备方法 |
Country Status (3)
| Country | Link |
|---|---|
| JP (2) | JP5700503B2 (enExample) |
| CN (2) | CN103436360B (enExample) |
| TW (1) | TWI522044B (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101795819B1 (ko) * | 2009-09-30 | 2017-11-09 | 후지세유 그룹 혼샤 가부시키가이샤 | 글리세리드 유지 중의 클로로프로판올류 및 그 형성 물질, 글리시돌 지방산 에스테르를 저감하는 방법 |
| CN102711496A (zh) * | 2009-12-04 | 2012-10-03 | 阿彻丹尼尔斯米德兰德公司 | 降低油中缩水甘油酯 |
| KR20110085142A (ko) * | 2010-01-19 | 2011-07-27 | 씨제이제일제당 (주) | 3-ｍｃｐｄ-ｆｓ가 저감화된 식용 유지의 제조방법 |
| JP5717352B2 (ja) | 2010-03-17 | 2015-05-13 | 花王株式会社 | 精製油脂の製造方法 |
| JP5717351B2 (ja) | 2010-03-17 | 2015-05-13 | 花王株式会社 | 精製油脂の製造方法 |
| JP2011213852A (ja) | 2010-03-31 | 2011-10-27 | Kao Corp | 油脂組成物 |
| JP5706094B2 (ja) * | 2010-03-31 | 2015-04-22 | 花王株式会社 | 油脂組成物 |
| MY161540A (en) * | 2010-05-07 | 2017-04-28 | Adeka Corp | Method for refining edible oil and fat |
| CN102453608B (zh) * | 2010-10-26 | 2013-09-04 | 中国石油化工股份有限公司 | 一种降低油脂酸值的方法以及所得到的油脂混合物 |
| PL3385360T3 (pl) * | 2011-02-10 | 2021-09-06 | Cargill, Incorporated | Proces redukcji zawartości 3-mcpd w olejach rafinowanych |
| JP6008596B2 (ja) * | 2011-06-15 | 2016-10-19 | 花王株式会社 | 精製油脂の製造方法 |
| MY159241A (en) | 2011-07-29 | 2016-12-30 | Nisshin Oillio Group Ltd | Purified glyceride composition and method for producing purified glyceride composition |
| JP6021382B2 (ja) * | 2011-07-29 | 2016-11-09 | 日清オイリオグループ株式会社 | グリセリド組成物の製造方法 |
| JP2016169391A (ja) * | 2011-07-29 | 2016-09-23 | 日清オイリオグループ株式会社 | パーム系油脂 |
| CN103060088A (zh) * | 2011-10-18 | 2013-04-24 | 丰益(上海)生物技术研发中心有限公司 | 控制油脂中缩水甘油酯的方法 |
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| JP5700503B2 (ja) | 2015-04-15 |
| JP2015045023A (ja) | 2015-03-12 |
| JP2011074358A (ja) | 2011-04-14 |
| CN102010786B (zh) | 2014-05-07 |
| CN103436360A (zh) | 2013-12-11 |
| TW201108943A (en) | 2011-03-16 |
| TWI522044B (zh) | 2016-02-21 |
| CN102010786A (zh) | 2011-04-13 |
| JP5973530B2 (ja) | 2016-08-23 |
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