JP5700503B2 - グリセリド組成物及び該グリセリド組成物の製造方法 - Google Patents
グリセリド組成物及び該グリセリド組成物の製造方法 Download PDFInfo
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- JP5700503B2 JP5700503B2 JP2010175282A JP2010175282A JP5700503B2 JP 5700503 B2 JP5700503 B2 JP 5700503B2 JP 2010175282 A JP2010175282 A JP 2010175282A JP 2010175282 A JP2010175282 A JP 2010175282A JP 5700503 B2 JP5700503 B2 JP 5700503B2
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- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 claims description 106
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 80
- 238000000034 method Methods 0.000 claims description 51
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- 238000004332 deodorization Methods 0.000 claims description 15
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
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- 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
- 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
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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 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-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
- 235000021357 Behenic acid Nutrition 0.000 description 2
- GBBVEDKVRCMWHI-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)C(CCCl)(O)O Chemical compound C(CCCCCCCCCCCCCCCCC)C(CCCl)(O)O GBBVEDKVRCMWHI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
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- 230000015572 biosynthetic process Effects 0.000 description 2
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- 235000019421 lipase Nutrition 0.000 description 2
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- 125000000466 oxiranyl group Chemical group 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
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- 238000010561 standard procedure Methods 0.000 description 2
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- 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 2
- 238000005406 washing Methods 0.000 description 2
- 239000002023 wood Substances 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
- XFGDAPQOKJYPQP-UHFFFAOYSA-N 1-chloropropane-1,2-diol Chemical compound CC(O)C(O)Cl XFGDAPQOKJYPQP-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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- 239000005909 Kieselgur Substances 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001982 diacylglycerols Chemical class 0.000 description 1
- 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
- 238000004821 distillation Methods 0.000 description 1
- 235000015071 dressings Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- TVQGDYNRXLTQAP-UHFFFAOYSA-N ethyl heptanoate Chemical compound CCCCCCC(=O)OCC TVQGDYNRXLTQAP-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 229910021397 glassy carbon Inorganic materials 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
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- 239000003456 ion exchange resin Substances 0.000 description 1
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- 230000007774 longterm Effects 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 150000004667 medium chain fatty acids Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- 150000002759 monoacylglycerols Chemical class 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical class CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000006864 oxidative decomposition reaction Methods 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
- 238000002360 preparation method Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000001629 suppression Effects 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
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010175282A JP5700503B2 (ja) | 2009-09-07 | 2010-08-04 | グリセリド組成物及び該グリセリド組成物の製造方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2009206504 | 2009-09-07 | ||
| JP2009206504 | 2009-09-07 | ||
| JP2010175282A JP5700503B2 (ja) | 2009-09-07 | 2010-08-04 | グリセリド組成物及び該グリセリド組成物の製造方法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014229170A Division JP5973530B2 (ja) | 2009-09-07 | 2014-11-11 | グリセリド組成物及び該グリセリド組成物の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011074358A JP2011074358A (ja) | 2011-04-14 |
| JP2011074358A5 JP2011074358A5 (enExample) | 2014-12-25 |
| JP5700503B2 true JP5700503B2 (ja) | 2015-04-15 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010175282A Active JP5700503B2 (ja) | 2009-09-07 | 2010-08-04 | グリセリド組成物及び該グリセリド組成物の製造方法 |
| JP2014229170A Active JP5973530B2 (ja) | 2009-09-07 | 2014-11-11 | グリセリド組成物及び該グリセリド組成物の製造方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014229170A Active JP5973530B2 (ja) | 2009-09-07 | 2014-11-11 | グリセリド組成物及び該グリセリド組成物の製造方法 |
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 |
|---|---|---|---|---|
| WO2011040539A1 (ja) * | 2009-09-30 | 2011-04-07 | 不二製油株式会社 | グリセリド油脂中のクロロプロパノール類及びその形成物質、グリシドール脂肪酸エステルを低減する方法 |
| EP2506720A4 (en) * | 2009-12-04 | 2015-03-04 | Archer Daniels Midland Co | REDUCTION OF GLYCIDYL ESTERS IN OIL |
| 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 |
| JP5829209B2 (ja) * | 2010-05-07 | 2015-12-09 | 株式会社Adeka | 食用油脂の精製方法 |
| 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 |
| EP2672834B2 (en) | 2011-02-10 | 2022-11-09 | Cargill Inc. | Process for the production of a refined oil |
| JP6008596B2 (ja) * | 2011-06-15 | 2016-10-19 | 花王株式会社 | 精製油脂の製造方法 |
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