CN106659176A - 包含大量月桂酸的中链甘油三酸酯的制备和合成 - Google Patents
包含大量月桂酸的中链甘油三酸酯的制备和合成 Download PDFInfo
- Publication number
- CN106659176A CN106659176A CN201480080505.1A CN201480080505A CN106659176A CN 106659176 A CN106659176 A CN 106659176A CN 201480080505 A CN201480080505 A CN 201480080505A CN 106659176 A CN106659176 A CN 106659176A
- Authority
- CN
- China
- Prior art keywords
- acid
- arbitrary described
- fatty acid
- described method
- methyl esters
- 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.)
- Pending
Links
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 239000005639 Lauric acid Substances 0.000 title abstract description 25
- 238000002360 preparation method Methods 0.000 title abstract description 15
- 229940057917 medium chain triglycerides Drugs 0.000 title abstract description 8
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 67
- 238000000034 method Methods 0.000 claims abstract description 39
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims abstract description 20
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims abstract description 19
- 235000013305 food Nutrition 0.000 claims abstract description 18
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims abstract description 17
- 230000032050 esterification Effects 0.000 claims abstract description 16
- 238000005886 esterification reaction Methods 0.000 claims abstract description 16
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims abstract description 9
- 235000013162 Cocos nucifera Nutrition 0.000 claims abstract description 9
- 244000060011 Cocos nucifera Species 0.000 claims abstract description 8
- 238000005194 fractionation Methods 0.000 claims abstract description 8
- 239000003921 oil Substances 0.000 claims description 35
- 150000004702 methyl esters Chemical class 0.000 claims description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 235000011187 glycerol Nutrition 0.000 claims description 23
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 18
- 239000000194 fatty acid Substances 0.000 claims description 18
- 229930195729 fatty acid Natural products 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 17
- 150000004665 fatty acids Chemical group 0.000 claims description 16
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- -1 fatty acid ester Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 239000003995 emulsifying agent Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000005642 Oleic acid Substances 0.000 claims description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 239000003349 gelling agent Substances 0.000 claims description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 claims description 3
- 239000004927 clay Substances 0.000 claims description 3
- 235000009508 confectionery Nutrition 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 238000012545 processing Methods 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000440 bentonite Substances 0.000 claims description 2
- 229910000278 bentonite Inorganic materials 0.000 claims description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 2
- 238000010924 continuous production Methods 0.000 claims description 2
- 229910021485 fumed silica Inorganic materials 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 4
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims 3
- 229940070765 laurate Drugs 0.000 claims 3
- 239000000463 material Substances 0.000 claims 3
- 230000003078 antioxidant effect Effects 0.000 claims 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 29
- 239000002537 cosmetic Substances 0.000 abstract description 16
- 230000008569 process Effects 0.000 abstract description 10
- 235000015872 dietary supplement Nutrition 0.000 abstract description 7
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 abstract description 5
- 229960002446 octanoic acid Drugs 0.000 abstract description 5
- 239000003814 drug Substances 0.000 abstract description 2
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 2
- 238000007670 refining Methods 0.000 abstract description 2
- 235000019198 oils Nutrition 0.000 description 31
- 101710137760 Malonyl-CoA-acyl carrier protein transacylase, mitochondrial Proteins 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003925 fat Substances 0.000 description 8
- 235000019197 fats Nutrition 0.000 description 8
- 235000019488 nut oil Nutrition 0.000 description 7
- 239000010466 nut oil Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 239000003240 coconut oil Substances 0.000 description 5
- 235000019864 coconut oil Nutrition 0.000 description 5
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 4
- 239000007844 bleaching agent Substances 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 3
- 235000021360 Myristic acid Nutrition 0.000 description 3
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000008406 cosmetic ingredient Substances 0.000 description 3
- 239000003974 emollient agent Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 238000012552 review Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Polymers OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 230000003925 brain function Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000008162 cooking oil Substances 0.000 description 2
- 235000013365 dairy product Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 235000015897 energy drink Nutrition 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 235000021472 generally recognized as safe Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000006082 mold release agent Substances 0.000 description 2
- 230000001537 neural effect Effects 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000012045 salad Nutrition 0.000 description 2
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 1
- JNYAEWCLZODPBN-UHFFFAOYSA-N 2-(1,2-dihydroxyethyl)oxolane-3,4-diol Polymers OCC(O)C1OCC(O)C1O JNYAEWCLZODPBN-UHFFFAOYSA-N 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 230000036626 alertness Effects 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000007961 artificial flavoring substance Substances 0.000 description 1
- 235000015173 baked goods and baking mixes Nutrition 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 230000003931 cognitive performance Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 235000011850 desserts Nutrition 0.000 description 1
- 235000019621 digestibility Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000003084 food emulsifier Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000007407 health benefit Effects 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 230000007056 liver toxicity Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 235000021085 polyunsaturated fats Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 238000013515 script Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000008983 soft cheese Nutrition 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 235000011496 sports drink Nutrition 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings or cooking oils characterised by the production or working-up
- A23D9/04—Working-up
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
-
- 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
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
- C11B3/04—Refining fats or fatty oils by chemical reaction with acids
-
- 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
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/005—Splitting up mixtures of fatty acids into their constituents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/08—Refining
- C11C1/10—Refining by distillation
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Microbiology (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Dispersion Chemistry (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- General Preparation And Processing Of Foods (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明属于具有>95％含量的C8(辛酸)、C10(癸酸)和C12(月桂酸)且月桂酸的含量约5％或以上的中链甘油三酸酯的效率高的大规模生产方法。该方法涉及主要从椰子或棕仁得到的脂肪酸甲酯的分馏、其与甘油的酯化从而合成中链甘油三酸酯，及对它们进行精炼以明显增加纯度及使它们适合人类消耗。这样的合成物在食品及其制备、健康增补剂、化妆品和药物等中具有重要用途。
Description
技术领域
本发明涉及油和脂肪领域，尤其涉及中链甘油三酸酯(MCT)合成物及其制备方法。
发明背景
中链甘油三酸酯为源自甘油和3种具有8-12碳链长度的脂肪酸的酯。主要脂肪酸成分为辛酸(C8)、癸酸(C10)和月桂酸(C12)。
MCT非常有用。商业上，MCT在食品制备中用作食品添加剂中的化学中间体。其也用于制备烘焙物品、饮料、口香糖、糖果和糖霜、乳制品类似物、脂肪&油、冷冻乳品甜点、加工过的水果、点心、成人营养品、软干酪及软糖。功能上，其用作乳化剂、能量来源、配制助剂、润滑剂、脱模剂、营养补充物、加工助剂、溶剂、载色剂、稳定剂、增稠剂、表面处理剂、组织形成剂及化妆品的润肤剂(US FDA 2014)。在健康方面，MCT作为食品的好处包括减少肠道伤害、避免肝毒性、抗炎症、减少胆固醇沉积和高血糖症(Martens et al.2006)。
随着MCT的好处被认识到，发现了几种另外的用途。专利EP0923317描述了在能量或体育饮料中的MCT，尤其设计来在重耐力训练期间代替体液、碳水化合物、脂类、氨基酸和矿物离子。除碳水化合物、左旋肉碱、矿物离子、氨基酸及小量浓缩果汁和人造香料之外，其还包含大量脂类，包括用油酸、癸酸或辛酸或者癸酸、辛酸或饱和月桂酸的任何组合酯化的甘油。另一用途允许MCT的稳定整合，其优化MCT的健康益处，包括容易消化性、更大的能量可用性及其它益处。专利US 20100119684 A1描述了包含MCT的食品合成物，包括占该食品合成物的2-10％的MCT。包括MCT成分允许增大量的MCT能成功和稳定地组合到食品合成物内。此外，专利US 7470445 B2描述了主要由富含MCT的甘油三酸酯组成的油或脂肪合成物。该油或脂肪合成物导致低身体脂肪累积、与传统食用油具有等效的烹饪性质、及具有适宜的香味和高安全性(Traul et al.2000)。
MCT的新用途为其对神经组织退化失调的治疗潜力。专利US 6835750 B1公开了将MCT用于治疗和预防阿尔茨海默氏病及因神经元新陈代谢减少引起的其它疾病。该专利论证了在用MCT治疗时认知能力的改善。最近，MCT配制品已被公开在使用包括有效量的椰子油和有效量的MCT的合成物时能提高和保持大脑功能(US 20130017278 A1)。
MCT在化妆品领域也正被积极地研究。专利US 8586060 B2提出了一种化妆用或药物制剂，用作凡士林的植物代替。作为MCT甘油三酸酯，其提供不同于普通油的物理特性。其具有较低的粘性，从而在用作润肤剂时提供快速扩散的媒介，及其不粘结在皮肤上或不油腻。如化妆品成分审查(CIR)专家小组(2003)得出结论的，用于化妆品应用的甘油三酸酯尤其是MCT在目前的使用和浓度实践中是安全的。总的来说，MCT油在US C.F.R.Title 21Part170下被认为GRAS(一般认为安全)并被美国食品和药物管理局认可。
本发明特别之处在于合成物中包含富集存在的C12(月桂酸)。相较于其它MCT，月桂酸具有特定用途。本发明所得的MCT涉及富集大量月桂酸的合成物，其用作食品制备中的食品增补剂、色拉油、油炸和烹饪用油，及用于化妆品、药妆品和药品目的。其还可制备为适当的制剂及食品制备中的组分。其可用作但不限于溶剂、乳化剂、能量来源、配制助剂、食品级润滑剂、脱模剂、营养补充物、加工助剂、溶剂、载色剂、稳定剂、增稠剂、表面处理剂、组织形成剂及化妆品的润肤剂。
具有大量月桂酸的MCT合成物可用作口服的食品增补剂，每日约1-2汤匙。其无味，是快速和立即的能量来源、大脑代用燃料从而提高机敏，及用作天然抗菌剂，因为月桂酸已被证明具有这样的性质。
此外，较高量的月桂酸与C8和C10酸提供抗菌、抗病毒和抗真菌生物活性的协合，及可用作天然自防腐剂。这样，发现在美容&化妆、药妆和医药行业的特殊用途(Marten etal.2006)。
具有大量月桂酸的MCT的用途的另一例子是用于热咖啡及其它液体制剂的预制混合油浓缩物的制备。具有大量月桂酸的预制混合MCT油通过添加约20％的油酸的蒸馏甘油一酸酯及聚乙氧基山梨糖醇酯的乳化剂混合物进行制备。其产生稳定的混合物，当添加到热咖啡或类似液体制剂内时，没有漂浮的MCT油。
此外，本发明涉及MCT的产生，其提供几个优点如稳固，这使得其用作局部滴旋和美容学的增稠剂或胶凝剂，具有更长的保存限期、抗酸败及更好的口味。
同样，在合成物中说到月桂酸的情形下，通常包括大量的非MCFA，如肉蔻酸(GB879211、JP2009142185)。总的来说，这可失去MCT的益处，尤其在其用在食品制备和生物活性应用中时。
除了产品之外，本发明提供更有效率的制备和生产具有大月桂酸含量的MCT的方法。如本领域通常已知的，商用MCT的大部分通过酯化甘油和C8-C12脂肪酸获得(US2238442、WO2013126990A1)。这在140℃到260℃的温度存在酸催化剂的情形下或者在40℃到90℃的温度使用酶如脂肪酶进行。
传统的MCT包含50％-70％的C8及30％-50％的C10，具有2％或更少的C12及3％或更少的C6(己酸)。本发明的目的在于建立经从椰子和/或棕榈坚果油得到的脂肪酸甲酯的酯化作用生产包含C8(辛酸)、C10(癸酸)和大量C12(月桂酸)的MCT的方法。在该情形下，优选的给料是脂肪酸甲酯，其更稳定及无腐蚀性，因而所需的生产设备和参数更容易维护和运行。作为缺点，该经脂肪酸甲酯生产MCT油的方法将导致副产品甲醇，其已知有毒。本发明因而还提出了有效的蒸馏和除臭工艺，其确保去除产品中的甲醇。
与现有技术相比，从所述使用脂肪酸甲酯的方法得到的MCT油包含大量用甘油酯化的C12。传统的MCT方法使用具有2％的月桂酸的脂肪酸进行制备。此外，新的MCT油将包含大部分的C8、C10和C12，其中C12包括2-70％，具有小量的C6和C14。在传统方法得到的MCT油也具有C8、C10和C12的同时，其具有更少量的C12。
从前面的描述，对本领域技术人员显而易见的是，本发明可以其它特定形式实施，而不背离本发明的精神和实质特性。所描述的实施方式应仅视为说明性而非限制性的实施方式，因为本发明的法律保护范围在权利要求中指明。
发明概述
本发明涉及大批生产的中链甘油三酸酯的合成，其通过用脂肪酸甲酯和/或来自椰子油和/或棕榈坚果油的脂肪酸酯化甘油得到。所述脂肪酸甲酯或脂肪酸通过酯基转移或分裂工艺进行生产。所得的脂肪酸甲酯进一步分馏以得到C8-12馏分，其之后用于生产最终的中链甘油三酸酯。C8-12馏分具有13-45％的C8含量、8-35％的C10含量及2-70％的C12含量。C8-12馏分包含少于2％的C6(己酸)和8％或更少的C14(肉蔻酸)。
这样的组分导致所得的具有大月桂酸含量的MCT能用作食品增补剂、食品制剂、色拉油、油炸和烹饪用油，及用于化妆品、药妆和医药用途。优选地，其在多种不同的食品制剂中完全可用作组成成分、健康增补剂和功能油。
由于该生产方法将产生甲醇，进一步提出去除该污染物的方法以产生安全及食用的MCT油。
附图说明
图1示出了C8-12甲酯馏分的分馏过程。椰子树甲酯(CME)以调节的流率连续馈入在高温、真空压力下运行的分馏柱。
图2示出了通过甘油和C8-12甲酯馏分的反应制备MCT的整个过程。粗制的MCT进入一系列精制处理以使其可食用，尤其是漂白和除臭处理。
发明描述
本发明提供完全新的、具有大月桂酸含量的MCT合成物。本发明还提供用于生产MCT的、脂肪酸甲酯和甘油在催化条件下直接酯化的方法。使用连续或半连续过程或者通过成批处理，甘油与C8-12甲酯馏分反应及用部分冷凝器在约200℃-220℃精制，以在反应过程和整个冷凝器期间使甲酯逆流从而连续去除反应副产品如甲醇(图2)。
C8-12甲酯馏分从全馏分椰子甲酯的分馏得到，其借助于本领域技术人员已知的通常称为“分馏柱”的蒸馏设备完成。分馏柱在55-65mbar压力下保持在95℃-100℃的塔顶温度和170℃-180℃的柱底温度，其中短链长度被收集，称为C8-C12甲酯馏分。底部馏分是粗制形式的C12-18甲酯的一部分，并可进一步蒸馏或分馏以用于其它用途如油脂化学品和表面活性剂。C8-12甲酯馏分受约16％-18％的椰子甲酯总进料和84％-88％的粗制C12-18甲酯馏分的影响。C8-12馏分由13-45％的C8(辛酸)、8-35％的C10(癸酸)和2-70％的C12(月桂酸)组成。C8-C12烷基可包含2％或更少的C6(己酸)和8％或更少的C14(肉蔻酸)。优选地，C8-12馏分由1％或更少的C6、35-45％的C8、25-31％的C10、20-30％的C12和0-4％的C14组成。该组成对于制备最终的MCT油是理想的。作为备选，不同的脂肪酸或其酯的分馏可通过其它手段完成，如使用多种不同的溶剂(Lindqvist et al.1974)。
C8-12馏分也可使用椰子脂肪酸作为给料或者使用棕榈坚果油或其甲酯衍生物在类似的分馏柱中进行制备。所得的C8-12馏分应优选也由1％或更少的C6、35-45％的C8、25-31％的C10、20-30％的C12和0-4％的C14组成。
之后，MCT油通过使C8-C12甲酯馏分与甘油反应及随后提纯进行制备(图2)。甘油与C8-12甲酯馏分的分子比为1摩尔甘油：3-4摩尔C8-C12甲酯，优选1摩尔甘油：3.3-3.9摩尔C8-12甲酯。根据本发明，所述反应在存在催化剂的情形下进行。所述反应在60-80mbar的真空及调节的氮吹条件下在140℃到260℃的温度下开始，优选180℃到220℃，在200℃到220℃内更好，直到转换为甘油三酸酯达到95％或更高为止。作为备选，这样的处理也可在大气状况下完成。作为甘油和甲酯冷凝的结果，甲醇被持续冷凝并从反应混合物中去除，多余的甲酯被允许逆流以驱动朝向甘油三酸酯制剂的反应。本领域技术人员应知道温度、催化剂和施加的真空的正确平衡以使能更快的转化及使酯化过程的反应时间更短。过量的C8-12甲酯被收集并可在酯化阶段期间重新使用。持续监视羟值(OHV)，直到实现5mgKOH/gm或更低的水平为止，优选1-3之间的OHV是符合需要的。
本发明的催化剂从下述催化剂选择：无机酸催化剂(同质或异质)、碱性催化剂及金属氧化物催化剂。同质无机酸催化剂的例子包括但不限于H3PO4、H2SO4、磺酸及衍生物如甲烷磺酸和p-甲苯磺酸。碱性催化剂的例子包括但不限于氢氧化钠、甲基化钠或甲基化钾。基于异质酸的催化剂的例子包括但不限于钛酸盐如丁基锡酸。金属氧化物或混合金属氧化物催化剂的例子包括但不限于锌氧化物、亚锡氧化物、铬氧化物和锆氧化物。
在制备所述新的MCT油时，优选的催化剂可以是下述之一：70％的甲磺酸、30％的甲氧基钠和丁基锡酸的钛酸盐，使用量为总混合物的0.30％到0.50％w/w。
本发明的甘油和C8-12甲酯馏分的酯化归并到精炼厂中以生产食用MCT油。从甘油和C8-12甲酯的直接酯化得到的粗制MCT因过分的摩尔比导致未反应的C8-12甲酯、存在酒精如甲醇的痕迹、及因未随C8-12甲酯完全冷凝而导致较高水平的甘油一酸酯和甘油二酯。
本发明的精炼规模厂具有叶片式压滤机、漂白槽、蒸汽除臭机和收集槽。已被描述包含未反应的甲酯和甲醇痕迹的粗制MCT油应在60-80mbar的真空下加热到200℃-220℃，同时调节的氮吹约2小时。大部分未反应的甲酯将被去掉，包括残留甲醇。废催化剂将通过使粗制MCT穿过在50℃-60℃加热的叶片式压滤机而去除并在漂白槽中进行收集。在漂白槽中，其将在60-80mbar的真空下加热到约90℃-110℃并持续约30-60分钟。白土和活性碳的添加量为总混合物的0.30-0.50％w/w。在所需的残留时间之后，停止真空。废漂白剂因通过50℃-60℃的叶片式压滤机而被去除。在蒸汽除臭机中，漂白后的MCT将在约170℃-200℃的温度加热。首先，其将在4-8mbar下加热约2小时。最后，其将在施加的4-8mbar真空下进一步加热到200℃并持续另一个4小时。在最终的精制MCT油中添加百万分之100-200(ppm)的稳定剂或抗氧化剂如柠檬酸。
本发明公开了从甘油和C8-12甲酯的反应大规模生产甘油三酸酯制剂尤其是MCT。本领域技术人员将意识到，有某些本发明权利要求之外的油和脂肪改型，虽然如此，其是显而易见的，因而应落在本发明的范围之内。例如，MCT可用具有痕量的C6和C14的单独的C8、C10和C12馏分进行制备。这些单独的馏分可以是脂肪酸甲酯或脂肪酸的形式并按所需比例混合以达到与本发明要求保护的MCT油一样的组成。另外，癸酸的甘油三酸酯、辛酸的甘油三酸酯和月桂酸的甘油三酸酯的混合物可以变化的比例进行混合。
商用MCT经脂肪酸(主要是C8-10)与甘油的酯化进行制备。C8-10脂肪酸可来自椰子油和非常常见的棕榈坚果油。根据收集处理的方法和效率，椰子油具有约10％-13％的C8-10脂肪酸馏分，而棕榈坚果油具有更低的约7-9％的C8-10馏分。本发明使得在最终的C8-12馏分中能萃取更大量的C12(月桂酸)馏分。
月桂酸油定义为MCT。在已知的油中，椰子或棕榈坚果油具有更高的月桂酸含量。椰子油具有约45-52％的月桂酸，棕榈坚果油具有43-48％的月桂酸。两种油均提供最高的C8-12馏分并提供更宽的灵活性以定制可变性质和形式的MCT。因此，本发明公开了利用C8-12馏分制备具有大量月桂酸的MCT。
本发明的另一优选实施例是C8-12甲酯馏分和甘油的酯化处理，使用甲酯馏分大规模商业生产食用MCT。优选地，具有大量月桂酸的MCT将具有1％或更少的C6、35-45％的C8、25-31％的C10、20-30％的C12和0-4％的C14。具有95％或更高的甘油三酸酯含量及约5％的组合的甘油一酸酯和甘油二酯。理想地，其具有0℃到1℃的滑熔点，在该温度下，其将从室温和更低的温度条件保持液态。每100ml食物量的营养值为750-860千卡，优选约840千卡(15ml食物量为110-135千卡，优选约130千卡)，总脂肪为90-100克，优选约93克(15ml食物量为12-15克，优选约14克)，饱和脂肪为90-100克(15ml食物量为12-15克，优选约14克)，反式脂肪、多不饱和脂肪及单饱和脂肪均为0克；0到痕量的胆固醇、钠、钾、包括纤维、可溶纤维和糖的总碳水化合物、蛋白质、维生素A、C和铁；痕量的硫胺、核黄素、尼亚新；及0到痕量的灰、水分和磷。
备选实施例
除其甘油三酸酯形式之外，在此提出的MCT油可进一步与化妆品级稠化剂/胶凝剂混合以使其为软凝胶从而用于皮肤化妆应用，优选通过组合为总混合物的3.5％w/w或更少的高纯度斑脱土黏土、烟雾硅胶和硅酸铝镁。
此外，在此提出的MCT油可进一步与食品乳化剂混合，从而用于饮料、咖啡奶油替代品或类似液体的预制混合制剂，优选由80％或以上的MCT油及20％或以下的食品乳化剂组成的混合物，包括但不限于硬脂酸或油酸的蒸馏甘油一酸酯、聚甘油脂肪酸酯及聚氧乙烯醚山梨糖醇酯的组合。
引用列表
专利文献
1.EP0923317.Gordeladze JO.Energy drink.Jun 23 1999
2.EP2636307.Lobee HWJ,Kruidenberg MB.Antimicrobial compositioncontaining free fatty acids and method for its production.Sep 11 2013
3.GB879211.Crawford RV,Southern CW.Improvements in or relating toglyceride esters.Oct 4 1961
4.JP2009142185.Onishi K,Shono Y,Suzuki K,Toda T,Haruna H.Oil And fatcomposition for cream,and cream containing the same.Jul 2 2009
5.US2006817558.Beetham P；Beetham pPR；Gocal G；Gocal GFV；Gocal GFW；Knuth M；Knuth ME；Walker K；Walker KA.Fatty acid mixtures and use thereof.May27 2013
6.US20100119684A1.Santana RD et al.Food compositions incorporatingmedium chain triglycerides.May 13 2010
7.US20130017278A1.Keller A.Composition and method for improving brainfunction.Jan 17 2013
8.US2238442.DREW ERNEST F.Mixed capric-caprylic esters and method ofmaking same.Apr 15 1941
9.US6835750B1.Henderson ST.Use of medium chain triglycerides for thetreatment and prevention of alzheimer's disease and other diseases resultingfrom reduced neuronal metabolism II.Dec 28 2004
10.US7470445B2.Takeuchi H.Oil or fat composition.Dec 30 2008
11.US8586060B2.Brinkmann B.Cosmetic or pharmaceutical preparation.Nov19 2013
非专利文献
1.Cosmetic Ingredient Review(CIR)Expert Panel.Annual review ofcosmetic ingredient safety assessments-2001/2002.International Journal ofToxicology 22(Suppl l):l-35 2003
2.Lindqvist B,Sjogren I,Nordin R.Preparative fractionation oftriglyceride mixtures according to acyl carbon number,usinghydroxyalkoxypropyl Sephadex.J Lipid Res.1974Jan；15(l):65-73.
3.Marten B,Pfeuffer M,Schrezenmeir J.Medium-chaintriglycerides.International Dairy Journal 16(2006)1374-1382.
4.Traul KA,Driedger A,Ingle DL,Nakhasi D.Review of the toxicologicproperties of medium-chain triglycerides.Food Chem Toxicol.2000Jan；38(l):79-98.
5.US FDA.http://www.accessdata.fda.gov/scripts/fdcc/？set＝GRASNotices&id＝449.July 7,2014.
Claims (32)
1.富含C8-12脂肪酸侧链的甘油三酸酯的生产方法，包括：(1)分馏脂肪酸甲酯；(2)收集馏分，每一馏分包含至少13％的C8(辛酸)、至少8％的C10(癸酸)和至少5％的C12(月桂酸)脂肪酸甲酯及少于5％的其它脂肪酸或其酯；及(3)用甘油酯化C8-C12脂肪酸甲酯以形成具有C8、C10和C12脂肪酸侧链长度的甘油三酸酯。
2.根据权利要求1所述的方法，其中所述脂肪酸甲酯通过蒸馏装置分馏。
3.根据权利要求1所述的方法，其中所述脂肪酸甲酯分馏为C8-12和C12-18馏分。
4.根据权利要求1-3任一所述的方法，其中处理为半连续处理。
5.根据权利要求1-3任一所述的方法，其中处理为连续处理。
6.根据权利要求1-3任一所述的方法，其中处理为按批处理。
7.根据权利要求1-3任一所述的方法，其中脂肪酸或其甲酯来自椰子。
8.根据权利要求1-3任一所述的方法，其中脂肪酸或其甲酯来自棕榈坚果。
9.根据权利要求1-3任一所述的方法，其中脂肪酸甲酯的馏分包含至少35％的C8、25％的C10和至少20％的C12。
10.根据权利要求1-3任一所述的方法，其中脂肪酸甲酯的馏分包含35-45％的C8、25-31％的C10和至少20％的C12。
11.根据权利要求1-3任一所述的方法，其中甘油与C8-12甲酯馏分的摩尔比为1摩尔甘油：3-4摩尔C8-12甲酯。
12.根据权利要求10所述的方法，其中甘油与C8-12甲酯馏分的摩尔比为1摩尔甘油：3.3-3.9摩尔C8-12甲酯。
13.根据权利要求1-3任一所述的方法，其中酯化反应在大气条件下或者在60-80mbar的真空下在140℃-260℃的温度并具有调节的氮吹的情形下开始。
14.根据权利要求13所述的方法，其中所述酯化反应步骤在180℃-220℃的温度下开始。
15.根据权利要求14所述的方法，其中所述酯化反应步骤在200℃-220℃的温度下开始。
16.根据权利要求1-3任一所述的方法，其中用于步骤(3)的催化剂从下述催化剂选择：无机酸催化剂、碱性催化剂及金属氧化物催化剂。
17.根据权利要求1-3任一所述的方法，其中用于步骤(3)的催化剂从下述催化剂选择：甲磺酸、甲氧基钠、和丁基锡酸的钛酸盐
18.根据权利要求1-3任一所述的方法，其中酯化率为95％以上。
19.根据权利要求1-3任一所述的方法，其中精炼甘油三酸酯合成物以去除甲醇的手段选自下述之一或其组合：(1)在具有调节的氮流的情形下及在真空下加热；(2)加热并使甘油三酸酯通过叶片式压滤机；(3)添加白土和活性碳并使该物质通过叶片式压滤机。
20.一种从根据权利要求1所述的方法得到的中链甘油三酸酯合成物，其中所述合成物包括至少13％的C8(辛酸)、至少8％的C10(癸酸)和至少20％的C12(月桂酸)及少于5％的其它脂肪酸含量。
21.一种从根据权利要求1所述的方法得到的中链甘油三酸酯合成物，其中所述合成物包括35-45％的C8、25-31％的C10和至少20％的C12及少于5％的其它脂肪酸含量。
22.一种中链甘油三酸酯合成物，包括至少13％的C8(辛酸)、至少8％的C10(癸酸)和至少20％的C12(月桂酸)及少于5％的其它脂肪酸含量。
23.根据权利要求22所述的合成物，其中所述甘油三酸酯包括至少35％的C8(辛酸)、至少25％的C10(癸酸)和至少20％的C12(月桂酸)及少于5％的其它脂肪酸含量。
24.根据权利要求20-23任一所述的合成物，其中所得到的脂肪酸完全或部分从椰子得到。
25.根据权利要求20-23任一所述的合成物，其中所得到的脂肪酸完全或部分从棕仁得到。
26.根据权利要求20-23任一所述的合成物，其中至少添加抗氧化剂物质。
27.根据权利要求26所述的合成物，其中所述抗氧化剂为柠檬酸。
28.一种增厚物质胡胶凝剂，包含根据权利要求19-25任一所述的合成物。
29.根据权利要求28所述的增厚物质或胶凝剂，其中根据权利要求20-27任一所述的合成物组合到至少下述之一：斑脱土黏土、烟雾硅胶或者硅酸铝镁。
30.一种食品乳化剂，包含根据权利要求20-27任一所述的合成物。
31.根据权利要求28所述的食品乳化剂，其中根据权利要求20-27任一所述的合成物组合到至少下述之一：硬脂酸或油酸的蒸馏甘油一酸酯、聚甘油脂肪酸酯或聚氧乙烯醚山梨糖醇酯。
32.根据权利要求20-31所述的产品的用途。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PH1-2014-000195 | 2014-07-10 | ||
| PH1/2014/000195A PH12014000195B1 (en) | 2014-07-10 | 2014-07-10 | Composition of medium chain triglycerides containing substantial amount of lauric acid |
| PCT/PH2014/000015 WO2016007026A1 (en) | 2014-07-10 | 2014-07-25 | Preparation and composition of medium chain triglycerides containing substantial amount of lauric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106659176A true CN106659176A (zh) | 2017-05-10 |
Family
ID=55064550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201480080505.1A Pending CN106659176A (zh) | 2014-07-10 | 2014-07-25 | 包含大量月桂酸的中链甘油三酸酯的制备和合成 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US10327452B2 (zh) |
| JP (3) | JP2017523261A (zh) |
| KR (2) | KR102229104B1 (zh) |
| CN (1) | CN106659176A (zh) |
| AU (3) | AU2014400680A1 (zh) |
| DE (1) | DE112014006800T5 (zh) |
| GB (2) | GB2583050B (zh) |
| MY (1) | MY181997A (zh) |
| PH (2) | PH12014000195B1 (zh) |
| WO (1) | WO2016007026A1 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI733864B (zh) * | 2016-07-27 | 2021-07-21 | 日商日清奧利友集團股份有限公司 | 油脂組成物 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201619789D0 (en) * | 2016-11-23 | 2017-01-04 | Pepsis Ltd | Enzyme-rich malt extract formulations |
| KR102446371B1 (ko) * | 2019-06-11 | 2022-09-22 | 대봉엘에스 주식회사 | 유지 조성물 및 이의 용도 |
| IL268457B (en) * | 2019-08-04 | 2022-05-01 | Omega 3 Galilee Ltd | Oil- suspension of edible solids and methods of preparing the same |
| WO2023076666A1 (en) * | 2021-10-31 | 2023-05-04 | One-Derings LLC | Insect-repellent personal-care composition |
| US11946011B1 (en) * | 2022-10-28 | 2024-04-02 | Perlman Consulting, Llc | Stabilized medium chain triglyceride-based household lubricant and protective coating |
| CN115925540B (zh) * | 2022-11-09 | 2024-06-14 | 广东聚石科技研究有限公司 | 一种三羟甲基丙烷中碳链酯及其制备方法和应用 |
| WO2024220918A1 (en) * | 2023-04-21 | 2024-10-24 | GlycosBio, INC. | Personal care compositions with enzyme-modified oils (emos) |
| WO2025038940A1 (en) * | 2023-08-16 | 2025-02-20 | Savor Foods Limited | System and method for triglyceride manufacture |
| US12234430B1 (en) | 2024-03-26 | 2025-02-25 | Perlman Consulting, Llc | Enhancing solubility of water in MCT oil using alcohols |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2238442A (en) * | 1939-05-25 | 1941-04-15 | Ernest F Drew | Mixed capric-caprylic esters and method of making same |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB879211A (en) | 1958-06-20 | 1961-10-04 | Bibby & Sons Ltd J | Improvements in or relating to glyceride esters |
| US5000975A (en) * | 1988-12-29 | 1991-03-19 | American Home Products Corporation | Randomized palm oil fat composition for infant formulas |
| NO301574B1 (no) | 1996-06-27 | 1997-11-17 | Jan Oxholm Gordeladze | Energidrikk |
| US6835408B2 (en) | 1998-11-13 | 2004-12-28 | The Nisshin Oillio Group, Ltd. | Oil or fat composition |
| US6835750B1 (en) | 2000-05-01 | 2004-12-28 | Accera, Inc. | Use of medium chain triglycerides for the treatment and prevention of alzheimer's disease and other diseases resulting from reduced neuronal metabolism II |
| JP3941599B2 (ja) * | 2002-06-11 | 2007-07-04 | 日本油脂株式会社 | 中鎖脂肪含有ゲル状食品 |
| GB0301577D0 (en) * | 2003-01-23 | 2003-02-26 | Edko Pazarlama Tanitim Ltd Sti | Topical pharmaceutical and/or cosmetic dispense systems |
| CA2656557C (en) | 2006-06-28 | 2015-08-11 | Cibus, Llc | Fatty acid blends and uses therefor |
| CN101652071B (zh) | 2007-04-02 | 2014-01-22 | 雀巢产品技术援助有限公司 | 包含中链甘油三酸酯的食品组合物 |
| DE102007031697A1 (de) | 2007-07-06 | 2009-01-08 | Walter Rau Neusser Öl und Fett AG | Kosmetische oder pharmazeutische Zubereitung |
| JP4925458B2 (ja) | 2007-12-13 | 2012-04-25 | 日清オイリオグループ株式会社 | クリーム用油脂組成物及び該油脂組成物を含有するクリーム |
| US20090311367A1 (en) * | 2008-06-17 | 2009-12-17 | Perry Stephen C | Dietary Supplement |
| US20120315369A1 (en) | 2011-06-10 | 2012-12-13 | Jeffrey John Kester | Cookware Release Compositions |
| US20130017278A1 (en) | 2011-07-13 | 2013-01-17 | Arlene Keller | Composition and method for improving brain function |
| TWI572352B (zh) | 2012-03-01 | 2017-03-01 | 波麥堤克藥學Ｓｍｔ有限公司 | 用於製備具中鏈長度之脂肪酸的三酸甘油酯之方法 |
| PT2636307E (pt) | 2012-03-07 | 2015-02-17 | Cargill Inc | Método de produção de composição antimicrobiana contendo ácidos gordos livres |
-
2014
- 2014-07-10 PH PH1/2014/000195A patent/PH12014000195B1/en unknown
- 2014-07-25 WO PCT/PH2014/000015 patent/WO2016007026A1/en active Application Filing
- 2014-07-25 JP JP2016572237A patent/JP2017523261A/ja active Pending
- 2014-07-25 KR KR1020197033409A patent/KR102229104B1/ko active Active
- 2014-07-25 US US15/324,298 patent/US10327452B2/en active Active
- 2014-07-25 KR KR1020177003873A patent/KR20170031738A/ko not_active Ceased
- 2014-07-25 DE DE112014006800.4T patent/DE112014006800T5/de not_active Withdrawn
- 2014-07-25 GB GB2011795.8A patent/GB2583050B/en not_active Expired - Fee Related
- 2014-07-25 CN CN201480080505.1A patent/CN106659176A/zh active Pending
- 2014-07-25 MY MYPI2017700048A patent/MY181997A/en unknown
- 2014-07-25 AU AU2014400680A patent/AU2014400680A1/en not_active Abandoned
- 2014-07-25 GB GB1620404.2A patent/GB2544204A/en not_active Withdrawn
-
2018
- 2018-12-20 JP JP2018238583A patent/JP2019056125A/ja active Pending
-
2019
- 2019-11-08 AU AU2019261791A patent/AU2019261791A1/en not_active Abandoned
-
2020
- 2020-02-04 PH PH1/2020/000038A patent/PH12020000038B1/en unknown
- 2020-09-30 JP JP2020164589A patent/JP7219251B2/ja active Active
-
2021
- 2021-05-20 AU AU2021203256A patent/AU2021203256A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2238442A (en) * | 1939-05-25 | 1941-04-15 | Ernest F Drew | Mixed capric-caprylic esters and method of making same |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI733864B (zh) * | 2016-07-27 | 2021-07-21 | 日商日清奧利友集團股份有限公司 | 油脂組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2019056125A (ja) | 2019-04-11 |
| GB2583050B (en) | 2021-03-24 |
| GB202011795D0 (en) | 2020-09-09 |
| PH12014000195A1 (en) | 2017-01-23 |
| JP7219251B2 (ja) | 2023-02-07 |
| GB2583050A (en) | 2020-10-14 |
| PH12014000195B1 (en) | 2023-06-30 |
| DE112014006800T5 (de) | 2017-04-06 |
| JP2017523261A (ja) | 2017-08-17 |
| MY181997A (en) | 2021-01-18 |
| US20170172170A1 (en) | 2017-06-22 |
| AU2014400680A1 (en) | 2017-01-05 |
| GB2544204A (en) | 2017-05-10 |
| AU2019261791A1 (en) | 2019-11-28 |
| KR102229104B1 (ko) | 2021-03-18 |
| JP2021011576A (ja) | 2021-02-04 |
| PH12020000038B1 (en) | 2024-02-06 |
| KR20170031738A (ko) | 2017-03-21 |
| AU2021203256A1 (en) | 2021-06-17 |
| WO2016007026A1 (en) | 2016-01-14 |
| US10327452B2 (en) | 2019-06-25 |
| GB201620404D0 (en) | 2017-01-18 |
| KR20190129143A (ko) | 2019-11-19 |
| PH12020000038A1 (en) | 2021-09-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7219251B2 (ja) | 多量のラウリン酸を含む中鎖脂肪酸トリグリセリドの調製及び組成物 | |
| KR100740564B1 (ko) | 공액화 리놀레산의 디글리세리드가 풍부한 유지조성물 | |
| JP4685355B2 (ja) | 甘草疎水性成分含有油脂組成物の製造方法 | |
| JP5088347B2 (ja) | 食感改良油脂組成物 | |
| JP2000502740A (ja) | ステロール及びリン化合物を含まない多不飽和脂肪酸及び脂肪酸エステルの混合物 | |
| JP2011223942A (ja) | 風味改善剤 | |
| JP2013530703A5 (zh) | ||
| TW201827599A (zh) | 脂肪酸乙酯之製備方法 | |
| WO2005079591A1 (fr) | Compositions de graisses et d'huiles contenant des diglycerides, et margarines, huiles de friture et aliments contenant ces compositions | |
| WO2015077499A1 (en) | Isolation of omega-7 fatty acid ethyl esters from natural oils | |
| JP6210741B2 (ja) | 呈味改善剤及び該呈味改善剤を含む香料組成物 | |
| Gustafson et al. | Pycnanthus angolensis: bioactive compounds and medicinal applications | |
| JP4191420B2 (ja) | 甘草疎水性抽出物を含有してなる食用油脂組成物 | |
| DE102005052442A1 (de) | Strukturierte Lipidgemische | |
| JP4265878B2 (ja) | カルノソールまたは／及びカルノジック酸を含有する機能性加工油脂の劣化防止剤及びこれを含有する油脂 | |
| HK1237213A1 (zh) | 包含大量月桂酸的中鏈甘油三酸酯的製備和合成 | |
| WO2018109203A2 (en) | Two-dimensional fractionation of milk fat | |
| JP6130513B2 (ja) | 雑味の低減された清涼感持続剤 | |
| JP4381362B2 (ja) | 油中水型乳化組成物 | |
| JP2018068289A (ja) | 層状食品用油中水型乳化物とそれを用いた可塑性油脂および層状食品の製造方法 | |
| JPWO2007086397A1 (ja) | 脂質代謝改善用油脂組成物 | |
| JP6799834B2 (ja) | 食用鯨油組成物の製造方法 | |
| JP5857338B2 (ja) | 呈味改善剤及びそれを含有する食品 | |
| JP2005264077A (ja) | 共役型トリエン酸含有油脂組成物及びその油脂の製造方法 | |
| JP2006335802A (ja) | ステロールエステルの脱臭方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 1237213 Country of ref document: HK |
|
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170510 |
|
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: WD Ref document number: 1237213 Country of ref document: HK |