CN101180995A - 低卡食用油的生产方法 - Google Patents
低卡食用油的生产方法 Download PDFInfo
- Publication number
- CN101180995A CN101180995A CNA2007101922482A CN200710192248A CN101180995A CN 101180995 A CN101180995 A CN 101180995A CN A2007101922482 A CNA2007101922482 A CN A2007101922482A CN 200710192248 A CN200710192248 A CN 200710192248A CN 101180995 A CN101180995 A CN 101180995A
- Authority
- CN
- China
- Prior art keywords
- oil
- acid
- catalyst
- low
- fatty acid
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 239000008157 edible vegetable oil Substances 0.000 title abstract description 6
- 239000003921 oil Substances 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 235000009508 confectionery Nutrition 0.000 claims abstract description 3
- 150000004668 long chain fatty acids Chemical class 0.000 claims abstract 2
- 235000019198 oils Nutrition 0.000 claims description 20
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims description 16
- 235000019197 fats Nutrition 0.000 claims description 15
- 239000004519 grease Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 11
- -1 carbon fatty acid Chemical class 0.000 claims description 10
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 claims description 8
- 239000001087 glyceryl triacetate Substances 0.000 claims description 8
- 235000013773 glyceryl triacetate Nutrition 0.000 claims description 8
- 229960002622 triacetin Drugs 0.000 claims description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 5
- 238000006386 neutralization reaction Methods 0.000 claims description 5
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 4
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 4
- 125000005908 glyceryl ester group Chemical group 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical group [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- 235000019865 palm kernel oil Nutrition 0.000 claims description 3
- 239000003346 palm kernel oil Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- 235000005687 corn oil Nutrition 0.000 claims description 2
- 239000002285 corn oil Substances 0.000 claims description 2
- 235000019621 digestibility Nutrition 0.000 claims description 2
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000005456 glyceride group Chemical group 0.000 claims description 2
- 229940070765 laurate Drugs 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
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 2
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 3
- 239000003426 co-catalyst Substances 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 1
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 claims 1
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- PTPNJVXPWNZRIR-UHFFFAOYSA-N CCCC(O)=O.OCC(O)CO.OCC(O)CO.OCC(O)CO Chemical compound CCCC(O)=O.OCC(O)CO.OCC(O)CO.OCC(O)CO PTPNJVXPWNZRIR-UHFFFAOYSA-N 0.000 claims 1
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- 235000019486 Sunflower oil Nutrition 0.000 claims 1
- 239000003240 coconut oil Substances 0.000 claims 1
- 235000019864 coconut oil Nutrition 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- 235000021313 oleic acid Nutrition 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000002600 sunflower oil Substances 0.000 claims 1
- 238000005516 engineering process Methods 0.000 abstract description 4
- 235000019219 chocolate Nutrition 0.000 abstract description 3
- 239000008162 cooking oil Substances 0.000 abstract description 3
- 235000013310 margarine Nutrition 0.000 abstract description 3
- 239000003264 margarine Substances 0.000 abstract description 3
- 230000004048 modification Effects 0.000 abstract description 3
- 238000012986 modification Methods 0.000 abstract description 3
- 238000004904 shortening Methods 0.000 abstract description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002131 composite material Substances 0.000 abstract description 2
- 239000004615 ingredient Substances 0.000 abstract 1
- 102000004169 proteins and genes Human genes 0.000 abstract 1
- 108090000623 proteins and genes Proteins 0.000 abstract 1
- 150000004666 short chain fatty acids Chemical class 0.000 abstract 1
- 239000003925 fat Substances 0.000 description 14
- 230000035479 physiological effects, processes and functions Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000004332 deodorization Methods 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 150000003722 vitamin derivatives Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OKMWKBLSFKFYGZ-UHFFFAOYSA-N 1-behenoylglycerol Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)CO OKMWKBLSFKFYGZ-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010000087 Abdominal pain upper Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000009874 alkali refining Methods 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000000205 computational method Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021474 generally recognized As safe (food) Nutrition 0.000 description 1
- 235000021472 generally recognized as safe Nutrition 0.000 description 1
- 235000021473 generally recognized as safe (food ingredients) Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000003642 hunger Nutrition 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 235000020845 low-calorie diet Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 229940074096 monoolein Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 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
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
Abstract
一种低卡食用油的生产方法，属油脂改性技术领域，其成分为长、短链脂肪酸三甘油酯，生理热量为3.9至6.2千卡，最佳为4.3千卡/1克油，与蛋白质相近，可加工做低卡烹调油、低卡巧克力、糖果用油、低卡人造奶油和高稳定的低卡起酥油。关键技术是配对的复合催化剂。
Description
技术领域
本发明属于油脂改性技术领域，制备一种长、短碳链脂肪酸三甘油酯，生理热量为低卡油脂。
背景技术
油脂是人类三大营养素之一，含有很高的热量，每克油约为9.6千卡，对维持人体生命过程，起举足轻重的作用，随着人们生活水平不断提高，在饮食中油脂越来越担任重要角色。但是，油脂大量摄入，对人体健康，带来明显的副作用，科学研究表明，肥胖，高血脂，糖尿病，动脉硬化，恶性肿瘤，与人们日常饮食中脂肪提供的热量过高有直接关系。据调查，全中国每年消耗食用油为2300万吨，每人18kg，每月1.5kg，每天50克，而大城市如北京，每天每人食用数量已达83克，而专家建议每天25克为宜。尽管如此，许多消费者无法接受单纯的减脂或无脂食品对粗糙的口感，同时，植物油还是烹调过程的热载体，减少或不用，无法加工出味美可口的菜肴，因此，开发低卡油脂，是解决上述难题的一个重要方向，这不仅填补国内这一领域空白，也为促进传统产业的技术升级换代创造条件，对促进人民的健康，经济效益和社会效益都是巨大的。
现市场上出售的低热量食品。如低热量奶油，它是将配方中的脂肪减少或代替，不是真正意义上的低卡油。
低卡热量油脂，在全世界，科学家已探索了很多年，最早由美国公司P&G公司F.Mattson博士报到了蔗糖酯不可消化性作为生理无热量油脂于1996年1月获美国FDA批准上市。后来，葡萄糖酯、戊糖酯及其它多元醇酯也先后开发出来。在实际消费使用中，却发现由于不消化性，引起严重泄露，对人体消化有潜在的影响，如腹痛，腹泻等副作用，推广受到限制，后又推出第二代低热量油脂。这是一类属改性三甘油酯，它能正常被人肠胃消化，对脂溶性维生素也不产生影响。如中碳甘油醇(MCT)中碳脂肪酸像碳水化合物一样消化，不会在人体再合成甘油酯而累积，但因原料来源有限，成本高。P&G公司又开发出中、长、超长三甘油脂(Gaprenin)也获美国FDA批准上市。其代表组成为油酸，葵酸和二十二碳酸三甘油酯，每克生理热量为4.5千卡/克油。
美国Nabiso集团开发出长、短碳链三甘油酯(Salatrin)和普通油脂一样消化吸收，没有泄露等不良反应，也不影响油溶性维生素的保留。它可任意比例代替普通油脂，热量仅为一般油脂的40％(一般油脂每克是9.64千卡，而乙酸酯仅为3.4千卡)。并获得美国食品和药品管理局(FDA)批准，作为公认安全物质(GRAS)应用在食品加工各个方面，很受欢迎。
生理热量计算公式＝燃烧热×吸收率％
长短碳链三甘油酯(Salatrin)Nabiso公司采用三步合成工艺路线，我国专利申请号为02123573·2，也是一种类似美国公司Nabiso公司产品。使用植物油为原料，经甘油解和酯化水洗碱炼，脱臭等工艺步聚。使用了在食品油加工中，未被批准的催化剂四丁基溴化铵和浓硫酸。工艺路线长在130-150℃高温区反应，不仅能耗大，也会引起不饱合脂肪酸的异构和反式化。也有文献报到用甲醇钠和酶催化，因为乙酸甘油酯没有α-H仲氢，除在很高温度，否则不易形成酯交换反应的活性中间体，取代量也很小，而酶促反应，需要加水，水解副反应加速，游离酸多，收率低。
发明内容
针对上述工艺路线长，反应条件要求苛刻的难题，本发明所采用的技术方案是：采用了高活性成对催化剂，主催化剂为亲核性极强的丙醇钠、乙醇钠，助催化促进剂为能在油中溶解的多元醇及其单酯。如丙三醇、丁二醇、丙二醇、单脂肪酸甘油酯、山梨醇单酯、木糖醇油酸单酯，游离的羟基对分子重排的启动非常重要，它们的亲电与醇钠亲核形成一对相互促进的活性催化剂。本发明的有益效果是，反应速度大大加快，反应时间是现有技术的四分之一，反应条件极其温和，反应温度降低了100摄氏度，收得率接近理论值。
具体实施方式
本发明技术方案，采用消化吸收率低的油脂。如高芥酸菜子油，全饱和的固体脂与三乙酸甘油酯和三丁酸甘油酯混合重排，反应在真空度750mmHg。反应温度40-60℃，搅拌速度60转/分，时间0.5～1h，测定皂化价，求平均分子量作为控制终点，用冰醋酸中和催化剂，停止反应，滤除中和生成的固态盐类，上层即为成品，选择不同油脂可得到不同用途的低卡油。
①用全饱和的油脂为原料，可得到稳定性极好的低卡起酥油。
②用一部分固体和液体油，与三乙酸甘油酯。三丁酸甘油酯重排，可得到固体指数适合的低卡人造奶油。
③用富月桂酸酯的油脂，与C18:0固体脂，和三乙酸酯重排，得到低卡巧克力，糖果用油脂。
④用高芥酸菜子油，可得到低卡色拉烹调油。产物的热量从3.9千卡至6千卡。
实施例1：
菜子油100kg，三乙酸甘油酯50kg，山梨醇单酯600克，乙醇钠300克预先溶解，作为复合催化剂，于60℃混合，搅拌，真空度大于730mmHg。反应0.5～1h，测皂化价为300个单位。停止反应，加入冰醋酸300克中和，分离沉淀物，净水洗涤一次，真空脱水得到液态低卡烹调油。生理热量为5千卡/克油。
计算方法：燃烧热(千卡)×吸收率％＝生理热量。高芥酸菜子油吸收率为80％。
实施例2：
碘价小于2的饱和固体脂500kg，三乙酸甘油酯250kg，丙醇钠150克+丙二醇300克，混合溶化。
将固体脂与三乙醇甘油酯加热混合，于60℃，在减压下加入催化剂，真空度保持720mmHg，反应50分钟，加入柠檬酸乙醇溶液中和催化剂至中性，过滤去盐类固体，水洗，真空脱水，得溶点41℃低卡起酥油。因硬脂酸吸收率为60％，所以生理热量为4.3千卡/1克油，高氧化稳定性，AOM值为280h。
实施例3：
用三硬脂酸甘油酯250kg，玉米油250kg，丙醇钠700克+乙醇钠80克，油酸单甘油酯300克，三乙酸甘油酯150kg，三丁酸甘油酯50kg。
在实施条件下，得到35℃的塑性油脂。
生理热量4.6千卡/1克油。固体指数，适合人造奶油。
实施例4：
全氢化棕榈仁油100kg，三乙酸甘油酯60kg，催化剂异丙醇钠300克，丁二醇600克，预先混溶。
于70℃，在减压下，将棕榈仁油与三乙酸甘油酯混合熔化，加入催化剂，反应1小时，用冰醋酸中和，水洗，真空脱臭，得成品。生理热量3.9千卡/1克油。
溶点33℃，因为是同质单晶，作为巧克力和糖果用油，无需调温操作，使用方便，口感佳。
Claims (6)
1.一种低卡油脂生产方法，成分为长、短链脂肪酸三甘油酯。其特征是，在每个三甘油酯分子中含一个以上短碳脂肪酸(C2-C4)和至少一个长碳脂肪酸(C12～C22)所组成的混合甘油酯。
具体内容为：
①选一种消化率低的油或脂，与三乙酸甘油酯、三丁酸甘油酯，按一定比例混合，油和三乙酸甘酯质量比为1∶0.25～1∶0.78。
②加入复合配对催化剂，用按油的质量比为0.2～0.8％。
③在减压下，于40-70℃反应，搅拌0.5～1h。
④用无水酸中和，水洗，得热量为3.9至6.2千卡/1克油产品。
2.如权利要求1的低卡油生产方法所述，长碳链脂肪酸为月桂酸、棕榈酸、硬脂酸，油酸、芥酸、亚油酸，它们来自椰子油、棕榈仁油、菜子油、玉米油、葵花籽油，及它们的极度氢化产品。
3.如权利要求1所述，低卡油的短碳链为乙酸、丁酸三甘油醇。
4.根据权利要求1所述，低卡油生产用的催化剂为丙醇钠、乙醇钠、异丙醇钠或其混合物。
5.如权利要求1所述，助催化剂为丙三醇、丁二醇、丙二醇、单油酸甘油酯、山梨醇单酯，与主催化剂质量比为1∶3，即助催化剂为3。
6.如权利要求1所述，反应温度40-70℃，搅拌速度60转/分，时间0.5～1h，真空度720mmHg以上。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007101922482A CN101180995B (zh) | 2007-12-24 | 2007-12-24 | 低卡食用油的生产方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007101922482A CN101180995B (zh) | 2007-12-24 | 2007-12-24 | 低卡食用油的生产方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101180995A true CN101180995A (zh) | 2008-05-21 |
| CN101180995B CN101180995B (zh) | 2011-05-11 |
Family
ID=39446527
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2007101922482A Active CN101180995B (zh) | 2007-12-24 | 2007-12-24 | 低卡食用油的生产方法 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101180995B (zh) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103999952A (zh) * | 2014-05-27 | 2014-08-27 | 安徽天利粮油集团股份有限公司 | 用米糠油制造低热量和保健性食用油的生产方法 |
| CN107873866A (zh) * | 2017-12-20 | 2018-04-06 | 温州金甫润油脂有限公司 | 一种食用油脂组合物及其制备方法 |
| CN115997826A (zh) * | 2023-02-24 | 2023-04-25 | 山东西王食品有限公司 | 一种多保健功能食用油的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1012078B (zh) * | 1985-04-01 | 1991-03-20 | 中国科学技术大学 | 一种油脂自催化酯交换生产多维营养油的方法 |
| CN1292670C (zh) * | 2002-07-04 | 2007-01-03 | 北京市粮食科学研究所 | 一种液态低热量油脂——混合的甘油三酯 |
| CN100531583C (zh) * | 2006-05-23 | 2009-08-26 | 大连兴龙垦有机粮油有限公司 | 低热量食用油脂生产方法 |
-
2007
- 2007-12-24 CN CN2007101922482A patent/CN101180995B/zh active Active
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103999952A (zh) * | 2014-05-27 | 2014-08-27 | 安徽天利粮油集团股份有限公司 | 用米糠油制造低热量和保健性食用油的生产方法 |
| CN107873866A (zh) * | 2017-12-20 | 2018-04-06 | 温州金甫润油脂有限公司 | 一种食用油脂组合物及其制备方法 |
| CN115997826A (zh) * | 2023-02-24 | 2023-04-25 | 山东西王食品有限公司 | 一种多保健功能食用油的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101180995B (zh) | 2011-05-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102845537B (zh) | 一种人乳脂替代品的制备方法 | |
| CN104186701B (zh) | 一种基于甘油三酯组成的人乳替代脂的制备方法及其评价方法 | |
| CN103999953B (zh) | 一种低反式酸改性油脂组合物及其制备方法 | |
| CN101305752B (zh) | 母乳脂肪替代油脂的生产方法 | |
| CN100999698B (zh) | 含有甘油酯型共轭亚油酸的油脂及其生产方法 | |
| CN108770954A (zh) | 一种高纯度中长链脂肪酸油脂的制备方法 | |
| 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 | |
| EP0594428A2 (en) | Process for producing a reduced caloric lipid composition | |
| CN101111155A (zh) | 降低反式酸含量的油脂组合物的制造方法和含有该油脂组合物的加工油脂产品 | |
| CN105821089A (zh) | 一种酶法合成中长链结构甘油三酯的方法 | |
| CN101940242B (zh) | 用于婴儿配方食品的油脂组合物 | |
| CN106916631A (zh) | 油脂组合物、母乳脂肪替代物及其制备方法 | |
| CN104365874B (zh) | 一种巧克力用油脂组合物及其制备方法和用途 | |
| CN104186705A (zh) | 基于酶促酸解棕榈酸甘油三酯合成结构脂质的方法 | |
| CN104247783A (zh) | 一种人造奶油和起酥油用油脂组合物及其制备方法 | |
| CN100531583C (zh) | 低热量食用油脂生产方法 | |
| CN101180995B (zh) | 低卡食用油的生产方法 | |
| CN101326941A (zh) | 一种低/零反式脂肪酸人造奶油/起酥油基料油的制备方法 | |
| CN102559394A (zh) | 低热量食用植物油制备工艺 | |
| CN105072917A (zh) | 脂肪组合物 | |
| CN103181417A (zh) | 一种油脂组合物、复合油脂组合物、制品及其制备方法 | |
| CN100500859C (zh) | 含中链甘油二酯的食用油脂组合物及其制备方法 | |
| CN114836483A (zh) | 一种富含opl和opo油脂组合物的制备方法 | |
| US20240032555A1 (en) | Breast milk structured lipid simulating the composition of triglycerides and method for preparing the same | |
| CN112029590A (zh) | 一种富含植物甾醇酯和甘油二酯的功能性油脂的制备方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20180125 Address after: The people of Anhui Tongling Tongguanshan District Building No. 77 Room 202 Patentee after: Tongling Feng Yuan Science and Technology Development Co., Ltd. Address before: Room 106, 19 floor, Eastern District, Hefei, China, No. 230026 Jinzhai Road, Hefei, Anhui Patentee before: Qian Shengqiu |
|
| TR01 | Transfer of patent right | ||
| CP02 | Change in the address of a patent holder |
Address after: No. 358, Caoshan Road, Tongling City, Anhui Province Patentee after: Tongling Feng Yuan Science and Technology Development Co.,Ltd. Address before: The people of Anhui Tongling Tongguanshan District Building No. 77 Room 202 Patentee before: Tongling Feng Yuan Science and Technology Development Co.,Ltd. |
|
| CP02 | Change in the address of a patent holder |