JPH06212188A - 低カロリー脂肪代用組成物の製造方法 - Google Patents
低カロリー脂肪代用組成物の製造方法Info
- Publication number
- JPH06212188A JPH06212188A JP5286202A JP28620293A JPH06212188A JP H06212188 A JPH06212188 A JP H06212188A JP 5286202 A JP5286202 A JP 5286202A JP 28620293 A JP28620293 A JP 28620293A JP H06212188 A JPH06212188 A JP H06212188A
- Authority
- JP
- Japan
- Prior art keywords
- esterified
- acid
- acyl group
- unsaturated
- polyol
- 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
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- 239000003778 fat substitute Substances 0.000 title claims description 38
- 238000002360 preparation method Methods 0.000 title description 6
- 125000002252 acyl group Chemical group 0.000 claims abstract description 141
- 229920005628 alkoxylated polyol Polymers 0.000 claims abstract description 105
- 239000003054 catalyst Substances 0.000 claims abstract description 46
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 32
- 150000003077 polyols Chemical class 0.000 claims abstract description 25
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 22
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 12
- 150000003624 transition metals Chemical class 0.000 claims abstract description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 90
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 80
- 239000000194 fatty acid Substances 0.000 claims description 80
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- 150000004665 fatty acids Chemical class 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 57
- 235000011187 glycerol Nutrition 0.000 claims description 44
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 35
- -1 aliphatic diols Chemical class 0.000 claims description 27
- 238000005886 esterification reaction Methods 0.000 claims description 22
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 21
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 21
- 230000032050 esterification Effects 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 16
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
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- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 12
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- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001339 alkali metal compounds Chemical class 0.000 claims description 7
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- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229930182470 glycoside Natural products 0.000 claims description 7
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 claims description 6
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- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000003512 tertiary amines Chemical class 0.000 claims description 6
- BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 claims description 5
- 150000003868 ammonium compounds Chemical class 0.000 claims description 5
- 229940108623 eicosenoic acid Drugs 0.000 claims description 5
- BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 claims description 5
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- CVCXSNONTRFSEH-UHFFFAOYSA-N docosa-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCCCCCC=CC=CC(O)=O CVCXSNONTRFSEH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- ATNNLHXCRAAGJS-QZQOTICOSA-N (e)-docos-2-enoic acid Chemical compound CCCCCCCCCCCCCCCCCCC\C=C\C(O)=O ATNNLHXCRAAGJS-QZQOTICOSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
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- 150000002924 oxiranes Chemical class 0.000 claims 4
- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 claims 1
- 150000002016 disaccharides Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 22
- 229920005862 polyol Polymers 0.000 abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
- 235000019210 fat mimetic Nutrition 0.000 abstract description 2
- 230000037396 body weight Effects 0.000 abstract 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 30
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 24
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 23
- 235000020778 linoleic acid Nutrition 0.000 description 23
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 23
- 235000013305 food Nutrition 0.000 description 22
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 18
- 238000003776 cleavage reaction Methods 0.000 description 18
- 230000003301 hydrolyzing effect Effects 0.000 description 18
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- 230000007017 scission Effects 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 17
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 16
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 16
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 16
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 15
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 15
- 239000005642 Oleic acid Substances 0.000 description 15
- 235000021314 Palmitic acid Nutrition 0.000 description 15
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 14
- 235000021355 Stearic acid Nutrition 0.000 description 14
- 239000003925 fat Substances 0.000 description 14
- 235000019197 fats Nutrition 0.000 description 14
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 14
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 14
- 230000008569 process Effects 0.000 description 14
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- 239000008117 stearic acid Substances 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 150000003626 triacylglycerols Chemical class 0.000 description 13
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 240000002791 Brassica napus Species 0.000 description 8
- 150000002118 epoxides Chemical class 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000012546 transfer Methods 0.000 description 8
- 150000002632 lipids Chemical class 0.000 description 7
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 6
- 235000021357 Behenic acid Nutrition 0.000 description 6
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 6
- 235000021353 Lignoceric acid Nutrition 0.000 description 6
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 6
- 229940116226 behenic acid Drugs 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 6
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
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- 229910052759 nickel Inorganic materials 0.000 description 5
- NNNVXFKZMRGJPM-KHPPLWFESA-N sapienic acid Chemical compound CCCCCCCCC\C=C/CCCCC(O)=O NNNVXFKZMRGJPM-KHPPLWFESA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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- 235000019484 Rapeseed oil Nutrition 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
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- HXYCHJFUBNTKQR-UHFFFAOYSA-N heptane-1,2,3-triol Chemical compound CCCCC(O)C(O)CO HXYCHJFUBNTKQR-UHFFFAOYSA-N 0.000 description 1
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- OHMBHFSEKCCCBW-UHFFFAOYSA-N hexane-2,5-diol Chemical compound CC(O)CCC(C)O OHMBHFSEKCCCBW-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 150000004678 hydrides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
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- 150000004704 methoxides Chemical class 0.000 description 1
- HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 description 1
- 235000020166 milkshake Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
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- 235000019508 mustard seed Nutrition 0.000 description 1
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- 235000014571 nuts Nutrition 0.000 description 1
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
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- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
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- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
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- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- CGIHFIDULQUVJG-UHFFFAOYSA-N phytantriol Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)(O)C(O)CO CGIHFIDULQUVJG-UHFFFAOYSA-N 0.000 description 1
- CGIHFIDULQUVJG-VNTMZGSJSA-N phytantriol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCC[C@@](C)(O)[C@H](O)CO CGIHFIDULQUVJG-VNTMZGSJSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000001259 polydextrose Substances 0.000 description 1
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- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 235000013606 potato chips Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 235000012434 pretzels Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 244000128879 sarson Species 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 1
- NGSFWBMYFKHRBD-UHFFFAOYSA-M sodium lactate Chemical compound [Na+].CC(O)C([O-])=O NGSFWBMYFKHRBD-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 210000005070 sphincter Anatomy 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
- 235000019408 sucralose Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 235000021092 sugar substitutes Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 235000008371 tortilla/corn chips Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- LKOVPWSSZFDYPG-WUKNDPDISA-N trans-octadec-2-enoic acid Chemical compound CCCCCCCCCCCCCCC\C=C\C(O)=O LKOVPWSSZFDYPG-WUKNDPDISA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 235000014107 unsaturated dietary fats Nutrition 0.000 description 1
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- 238000004260 weight control Methods 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
-
- 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
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
- A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
- A23L33/25—Synthetic polymers, e.g. vinylic or acrylic polymers
- A23L33/26—Polyol polyesters, e.g. sucrose polyesters; Synthetic sugar polymers, e.g. polydextrose
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Nutrition Science (AREA)
- Health & Medical Sciences (AREA)
- Mycology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Edible Oils And Fats (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/964816 | 1992-10-22 | ||
| US07/964,816 US5288884A (en) | 1992-10-22 | 1992-10-22 | Process for producing a reduced calorie fat mimetic composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06212188A true JPH06212188A (ja) | 1994-08-02 |
Family
ID=25509054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5286202A Pending JPH06212188A (ja) | 1992-10-22 | 1993-10-22 | 低カロリー脂肪代用組成物の製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5288884A (en, 2012) |
| EP (1) | EP0594429A3 (en, 2012) |
| JP (1) | JPH06212188A (en, 2012) |
| KR (1) | KR940008578A (en, 2012) |
| AU (1) | AU667401B2 (en, 2012) |
| CA (1) | CA2108642A1 (en, 2012) |
| TW (1) | TW251223B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108659963A (zh) * | 2018-05-25 | 2018-10-16 | 未名生物能源有限公司 | 一种以劣质油脂为原料生产生物柴油的方法 |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5298637A (en) * | 1992-10-22 | 1994-03-29 | Arco Chemical Technology, L.P. | Process for producing a reduced calorie lipid composition |
| US5399729A (en) * | 1993-08-31 | 1995-03-21 | Arco Chemical Technology, L.P. | Esterified alkoxylated polyol fat substitutes having high primary ester content |
| US5466843A (en) * | 1994-04-29 | 1995-11-14 | Arco Chemical Technology, L.P. | Process for preparing a C12 -C24 saturated fatty acid esterified alkoxylated polyol |
| US5597605A (en) * | 1995-02-09 | 1997-01-28 | Arco Chemical Technology, L.P. | Reduced calorie fat component |
| US5589217A (en) * | 1995-05-11 | 1996-12-31 | Arco Chemical Technology, L.P. | Reduced calorie fat component |
| US6235335B1 (en) * | 1995-12-13 | 2001-05-22 | Bestfoods | Method of making a reduced calorie reconstituted milk composition |
| US5935631A (en) * | 1995-12-20 | 1999-08-10 | Cpc International, Inc. | Reduced calorie fried snacks having a cooling sensation when placed in the mouth |
| US6310227B1 (en) | 1997-01-31 | 2001-10-30 | The Procter & Gamble Co. | Reduced calorie cooking and frying oils having improved hydrolytic stability, and process for preparing |
| US7276485B1 (en) | 1997-04-21 | 2007-10-02 | The Procter + Gamble Co. | Flowable nondigestible oil and process for making |
| US6518226B2 (en) | 1997-05-20 | 2003-02-11 | The Procter & Gamble Co. | Flowable composition and a process for making the flowable composition |
| US6965043B1 (en) | 1997-11-10 | 2005-11-15 | Procter + Gamble Co. | Process for making high purity fatty acid lower alkyl esters |
| JP4316135B2 (ja) | 1998-01-09 | 2009-08-19 | ザ プロクター アンド ギャンブル カンパニー | ストリッピング混合物からの低級アルキルアルコールの回収 |
| CA2325411C (en) | 1998-03-23 | 2007-01-30 | The Procter & Gamble Company | Improved processes for synthesis and purification of nondigestible fats |
| ATE240966T1 (de) | 1998-03-23 | 2003-06-15 | Procter & Gamble | Herstellung von hochveresterten polyol- fettsäurepolyestern |
| US6562394B1 (en) | 1998-05-20 | 2003-05-13 | The Procter & Gamble Co. | Flowable nondigestible oil and process for making |
| US6268010B1 (en) * | 1999-06-15 | 2001-07-31 | Bestfoods | Reduced calorie fat mimetics with an average number of oxyalkylene groups per molecule of no more than five |
| AU2437901A (en) * | 1999-12-17 | 2001-06-25 | Procter & Gamble Company, The | Reduced calorie fat compositions |
| DE10013625A1 (de) * | 2000-03-18 | 2001-09-27 | Dornier Gmbh Lindauer | Fadenbremse, insbesondere Schussfadenbremse für Webmaschinen |
| US20080113067A1 (en) * | 2005-10-17 | 2008-05-15 | Monoj Sarma | Protein-Containing Food Product and Coating for a Food Product and Method of Making Same |
| US20070087085A1 (en) * | 2005-10-17 | 2007-04-19 | Bunge Oils, Inc. | Protein-containing food product and coating for a food product and method of making same |
| US20070148311A1 (en) * | 2005-12-22 | 2007-06-28 | Bunge Oils, Inc. | Phytosterol esterification product and method of make same |
| JP5585863B2 (ja) * | 2010-02-01 | 2014-09-10 | 日油株式会社 | ポリアルキレングリコール誘導体 |
| KR101772720B1 (ko) | 2010-02-01 | 2017-08-29 | 니치유 가부시키가이샤 | 폴리알킬렌 글리콜 유도체 및 이를 배합하여 이루어지는 화장료 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2610125A (en) * | 1949-11-16 | 1952-09-09 | Drew & Co Inc E F | Edible fatty material |
| US2625484A (en) * | 1951-11-19 | 1953-01-13 | Swift & Co | Lard crystal modification |
| US2625485A (en) * | 1952-03-26 | 1953-01-13 | Swift & Co | Lard crystal modification process |
| US2625486A (en) * | 1952-04-04 | 1953-01-13 | Swift & Co | Process of producing modified lard |
| US2625487A (en) * | 1952-05-08 | 1953-01-13 | Swift & Co | Modification of lard |
| US2733251A (en) * | 1954-09-02 | 1956-01-31 | Molecular rearrangement process | |
| US3337595A (en) * | 1960-09-15 | 1967-08-22 | Nalco Chemical Co | Fatty acid esters of polyoxypropylated glycerol |
| US3353964A (en) * | 1963-09-23 | 1967-11-21 | Procter & Gamble | Corandomized margarine oils |
| DE1595369C3 (de) * | 1966-12-15 | 1973-10-04 | Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen | Derivate von Blockcopolymerisaten des Äthylenoxids und des 1,2-Propylends und Verfahren zu deren Herstellung |
| DD207070A3 (de) * | 1982-04-27 | 1984-02-15 | Adw Der Ddr,Dd | Verfahren zur herstellung von nahrungsmitteln mit veraendertem naehrwert |
| US4849242A (en) * | 1986-03-31 | 1989-07-18 | The Dow Chemical Company | Method for reducing the available calories in a food composition |
| US4861613A (en) * | 1986-07-25 | 1989-08-29 | Arco Chemical Technology, Inc. | Non-digestible fat substitutes of low-caloric value |
| DE3636086A1 (de) * | 1986-10-23 | 1988-04-28 | Henkel Kgaa | Fettsaeureester von polyglycerinpolyglykolethern, ihre herstellung und ihre verwendung |
| CA1339929C (en) * | 1987-12-15 | 1998-06-30 | Paul Seiden | Reduced calorie fats made from triglycerides containing medium and long chain fatty acids |
| US5175323A (en) * | 1988-08-01 | 1992-12-29 | Arco Chemical Technology, L.P. | Preparation of esterified propoxylated glycerin by transesterification |
| US4983329A (en) * | 1988-08-26 | 1991-01-08 | Arco Chemical Technology, Inc. | Preparation of esterified propoxylated glycerin from free fatty acids |
| CA2012381C (en) * | 1989-03-28 | 1997-07-01 | Paul Seiden | Reduced calorie fat compositions containing polyol polyesters and reduced calorie triglycerides |
| EP0396406A3 (en) * | 1989-05-05 | 1992-03-18 | ARCO Chemical Technology, L.P. | Pharmaceutical formulations employing esterified alkoxylated polyols as vehicles |
| EP0396405A3 (en) * | 1989-05-05 | 1991-05-08 | Arco Chemical Technology, Inc. | Cosmetic formulations employing esterified alkoxylated polyol carriers |
| US5077073A (en) * | 1989-08-25 | 1991-12-31 | The Proctor & Gamble Company | Ethoxylated sugar and sugar alcohol esters useful as fat substitutes |
| US5059443A (en) * | 1989-08-30 | 1991-10-22 | The Procter & Gamble Co. | Esterified ethoxylated alkyl glycosides useful in low calorie fat-containing food compositions |
| CA2031879C (en) * | 1989-12-11 | 1999-08-24 | Charles F. Cooper | Compositions useful as high temperature media |
| JPH05504062A (ja) * | 1990-01-16 | 1993-07-01 | ザ・ダウ・ケミカル・カンパニー | 低カロリー脂肪代替物質、代替物質の製法およびその前駆体 |
| CA2053147A1 (en) * | 1990-10-15 | 1992-04-16 | Charles F. Cooper | Esterified polyoxyalkylene block copolymers as reduced calorie fat substitutes |
| PH31242A (en) * | 1990-10-19 | 1998-06-18 | Cpc International Inc | Reduced calory fat mimetics comprising esterified propoxylated monoglycerides and diglycerides. |
| US5118448A (en) * | 1990-10-19 | 1992-06-02 | Arco Chemical Technology, L.P. | Process for producing esterified alkoxylated polyols |
| US5135683A (en) * | 1991-03-28 | 1992-08-04 | Arco Chemical Technology, L.P. | Process for producing a deprotected alkoxylated polyol |
| US5298637A (en) * | 1992-10-22 | 1994-03-29 | Arco Chemical Technology, L.P. | Process for producing a reduced calorie lipid composition |
-
1992
- 1992-10-22 US US07/964,816 patent/US5288884A/en not_active Expired - Lifetime
-
1993
- 1993-10-18 CA CA002108642A patent/CA2108642A1/en not_active Abandoned
- 1993-10-21 EP EP93308381A patent/EP0594429A3/en not_active Ceased
- 1993-10-22 KR KR1019930022190A patent/KR940008578A/ko not_active Withdrawn
- 1993-10-22 JP JP5286202A patent/JPH06212188A/ja active Pending
- 1993-10-22 AU AU50239/93A patent/AU667401B2/en not_active Ceased
- 1993-11-16 TW TW082109571A patent/TW251223B/zh active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108659963A (zh) * | 2018-05-25 | 2018-10-16 | 未名生物能源有限公司 | 一种以劣质油脂为原料生产生物柴油的方法 |
| CN108659963B (zh) * | 2018-05-25 | 2021-09-21 | 未名生物能源有限公司 | 一种以劣质油脂为原料生产生物柴油的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0594429A2 (en) | 1994-04-27 |
| KR940008578A (ko) | 1994-05-16 |
| AU667401B2 (en) | 1996-03-21 |
| EP0594429A3 (en) | 1994-12-14 |
| CA2108642A1 (en) | 1994-04-23 |
| TW251223B (en, 2012) | 1995-07-11 |
| AU5023993A (en) | 1994-05-05 |
| US5288884A (en) | 1994-02-22 |
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