CN1465262A - Liquid state low calorie fat mixed triglyceride - Google Patents
Liquid state low calorie fat mixed triglyceride Download PDFInfo
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- CN1465262A CN1465262A CNA021235732A CN02123573A CN1465262A CN 1465262 A CN1465262 A CN 1465262A CN A021235732 A CNA021235732 A CN A021235732A CN 02123573 A CN02123573 A CN 02123573A CN 1465262 A CN1465262 A CN 1465262A
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Abstract
The present invention discloses a method for producing low calorie oil which is liquid at normal temp. by general vegetable oil and adopting ester exchange process. Said invented product has reasonable fatty acid structure, and can provide enough fatty acid required for human body. It can be used as industrial oil and domestic edible oil.
Description
One, technical field
The invention belongs to the vegetable fat ester exchange, making under a kind of normal temperature by short carbon chain acid in the esterification is a kind of method of the length chain low calorie fat of liquid state.
Two, background technology
Grease plays a part very important to health.Along with improving constantly of people's living standard, the grease series products is being played the part of more and more important role with its tempting mouthfeel and fragrance in diet.But a large amount of absorptions of grease have brought more and more significant side effects to health in the diet.Nutrition and medical research show, the fat institute heat that provides is too high in what is called " rich man's disease " such as malignant tumour, hyperlipemia, hypertension, artery sclerosis, coronary heart disease, obesity, diabetes and the people's diet a direct relation.Show that according to up-to-date medical research data the U.S. has 15.5 ten thousand people to suffer from colon cancer every year; Per 1000 women just have 1 people to suffer from breast cancer, and this all provides heat too high relevant with Excessive Intake fat and its.Obese children is more and more in the actual life, and the obesity patient is seen everywhere.The every day that China is recommended nutrient allowance (RDA) in the meals, the percentage of fatty energy supply is 25% in suggestion China adult meals, and the average of Beijing and two places, Sichuan has surpassed 31%, the percentage of fatty energy supply is higher in city dweller's meals, and coronary heart disease, artery sclerosis, obesity chronic diseases incidence are increased.But because that grease plays a part the mouthfeel of food, local flavor, matter structure etc. is very important, it is impossible removing fat fully in diet, reduces the quality that grease amount also can have a strong impact on food.For the health of health, fatty intake during people's utmost point need be kept on a diet, but many consumers can't accept simple fat reducing again or not have the fat foods rough mouthfeel, and therefore developing low calorie fat is important developing direction of food science and technology industry.
At present existing several length chain low calorie fats, mainly be after separating by ordinary hydrogen carburetion glycerine again with short-chain fat acid reaction or ordinary hydrogen carburetion and glyceryl triacetate reaction, or separate again by common vegetable fat glycerine and to react then with SCFA or common vegetable oil and glyceryl triacetate that hydrogenation makes product.
Three, summary of the invention
The invention provides a kind of liquid state low calorie fat, wherein long-chain comes from common vegetable fat, in its contained LCFA, saturated fatty acid: monounsaturated fatty acids: the ratio of polyunsaturated fatty acid is 3: 4: 3 (a mol ratio), meet body fat acid absorption equilibrium, and enough essential fatty acids can be provided; Its short chain is mainly the volatility short chain acids, as acetate, propionic acid, butyric acid etc.The composition characteristic of length chain acyl glyceride wherein is LLS, LSL, SSL, SLS type triglycerides, and L refers to LCFA, can be chain saturated fatty acids, can be long-chain unsaturated fatty acid also, and carbon number is between 12-24; S refers to SCFA, is acetate, propionic acid, butyric acid, can be one or more mixture wherein.Wherein the content of triglyceride of LLS, LSL type is 20%～70%; SSL, SLS type content of triglyceride are 30%～80%.The content of length chain acyl glyceride wherein shared ratio in mixture is 10%～90% (percentage by weight), and common content of oil and grease is 10%～90%.The grease heat is compared with feedstock oil and has been reduced by 10%～40%.
In order to realize above purpose, feedstock oil used in the present invention mainly contains soybean oil, peanut oil, rapeseed oil, palm oil, the common vegetable oil of kardiseed wet goods or its oil that mixes by a certain percentage and glycerine 110 ℃～150 ℃ temperature, carry out under the catalysis of phase transfer catalyst, salt, time is 30min～180min, removes residue glycerine by centrifugation.Esterification is reacted 2.0h～3.0h with 0.1～0.2 times of acetate, butyric acid or propionic acid or its mixture of substrate weight earlier; Adopt 0.1～0.15 times acetic anhydride, butyric anhydride or propionic andydride or its mixture reaction 1.0h～1.5h of substrate weight then.。The present invention has the technology characteristic of simple.Its product has the following characteristics:
1, its mode of appearance, mouthfeel, physicochemical properties and conventional grease are similar, are liquid under the normal temperature;
Do not interact with other nutrient, flavor substance in the food.Meet the edible vegetable oil health
Standard.
2, its short chain is mainly acetate, propionic acid, butyric acid or its mixture; Its caloric value is lower than conventional grease,
Be 60%～90% of common grease.
3, saturated fatty acid: monounsaturated fatty acids: the ratio of polyunsaturated fatty acid is 3: 4: 3 (mol
Than), meet body fat acid absorption equilibrium, and enough essential fatty acids can be provided.
Four, the specific embodiment
Below in conjunction with embodiment the present invention is done an explanation.
Technical scheme of the present invention adopts glycerine and common vegetable oil (or mixed vegetable oil) to carry out glycerine under certain condition and separates, and with the acry radical donor reaction, obtains crude product then.Carry out refining steps such as alkali refining, dehydration at last.
Reparation technology is as follows:
The catalyst esterification
Vegetable oil+glycerine → glycerine hydrolysis products → esterification products → crude product → washing → drying → alkali refining → deodorization → drying → product
Employed raw material and proportioning thereof are:
Common vegetable oil, as soybean oil, peanut oil, rapeseed oil, palm oil, safflower seed oil or to mix the ratio that forms with glycerine by a certain percentage mutually be 1: 1～1: 4 (mol than), the common catalysis of phase transfer catalyst and salt, 110 ℃～150 ℃ temperature, consumption is 0.1%～5% a phase transfer catalyst of raw material, as tetrabutylammonium chloride, TBAB, etamon chloride, hexadecyltrimethylammonium chloride, softex kw, salt is as Na
2SO
4, K
2SO
4Catalysis under carry out N
2Or CO
2Protection, the reaction time is 30min～180min.Remove residue glycerine by centrifugation.Esterification is under refluxad carried out, earlier with acetate, propionic acid, butyric acid or its mixture, its consumption is 0.10～0.2 times (weight ratio) of glycerine hydrolysis products, reaction 2～3h, adopt acetic anhydride, propionic andydride, butyric anhydride or its mixture reaction 1.0h～1.5h then, its consumption is 0.1～0.15 times (weight ratio) of glycerine hydrolysis products, obtains crude product.Carry out refining steps such as alkali refining, dehydration at last, obtain finished product.Long-chain fat acid content gas Chromatographic Determination, short-chain fat acid content adopt NMR to measure, and heat refers to the combustion heat.
Embodiment 1:
Soybean oil 30kg, glycerine 2.9kg, consumption are 0.1% tetrabutylammonium chloride and K of raw material
2SO
4Common catalysis, temperature is 130 ℃, N
2Carry out glycerine under the protection and separate 40min, the centrifugal then glycerine of removing.Esterification is under refluxad carried out, and using acetate, its consumption earlier is 3.3kg, and reaction 2.0h adopts acetic anhydride 1.0h then, and its consumption is 3.3kg, obtains crude product.Carry out refining steps such as alkali refining, dehydration at last, obtain finished product.The content of length chain acyl glyceride shared ratio in mixture is 65% (percentage by weight), and heat is 27% of a feedstock oil.
Embodiment 2:
Peanut oil 30kg, glycerine 3.5kg, consumption are 0.1% TBAB and K of raw material
2SO
4Common catalysis, temperature is 120 ℃, N
2Carry out glycerine under the protection and separate 100min, the centrifugal then glycerine of removing.Esterification is under refluxad carried out, and using acetate, its consumption earlier is 3.7kg, and reaction 2.0h adopts acetic anhydride 1.3h then, and its consumption is 3.1kg, obtains crude product.Carry out refining steps such as alkali refining, dehydration at last, obtain finished product.The content of length chain acyl glyceride shared ratio in mixture is 73% (percentage by weight), and heat is 30% of a feedstock oil.
Embodiment 3:
Rape seed oil 30kg, glycerine 2.9kg, consumption are 0.1% etamon chloride and Na of raw material
2SO
4Common catalysis, temperature is 110 ℃, N
2Carry out glycerine under the protection and separate 150min, the centrifugal then glycerine of removing.Esterification is under refluxad carried out, and using propionic acid, its consumption earlier is 3.3kg, and reaction 2.0h adopts propionic andydride reaction 1.0h then, and its consumption is 3.3kg, obtains crude product.Carry out refining steps such as alkali refining, dehydration at last, obtain finished product.The content of length chain acyl glyceride shared ratio in mixture is 68% (percentage by weight), and heat is 28% of a feedstock oil.
Embodiment 4:
Palm oil 30kg, glycerine 3.3kg, consumption are 0.1% etamon chloride and Na of raw material
2SO
4Common catalysis, temperature is 140 ℃, N
2Carry out glycerine under the protection and separate 160min, the centrifugal then glycerine of removing.Esterification is under refluxad carried out, and using butyric acid, its consumption earlier is 3.9kg, and reaction 2.0h adopts butyric anhydride reaction 1.0h then, and its consumption is 3.7kg, obtains crude product.Carry out refining steps such as alkali refining, dehydration at last, obtain finished product.The content of length chain acyl glyceride shared ratio in mixture is 63% (percentage by weight), and heat is 25% of a feedstock oil.
Embodiment 5:
Safflower oil 30kg, glycerine 2.9kg, consumption are 0.1% hexadecyltrimethylammonium chloride and Na of raw material
2SO
4Common catalysis, temperature is 145 ℃, N
2Carry out glycerine under the protection and separate the centrifugal then glycerine of removing.Esterification is under refluxad carried out, and with second, third, butyric acid, its consumption is 3.5kg earlier, and reaction 2.5h adopts second, third, butyric anhydride reaction 1.5h then, and its consumption is 3.3kg, obtains crude product.Carry out refining steps such as alkali refining, dehydration at last, obtain finished product.The content of length chain acyl glyceride shared ratio in mixture is 69% (percentage by weight), and heat is 25% of a feedstock oil.
Embodiment 6:
Feedstock oil is soybean oil and palm oil interworking oil (0.84: 1, mol than), and safflower oil 30kg, glycerine 4kg, consumption are 0.1% softex kw and K of raw material
2SO
4Common catalysis, temperature is 145 ℃, N
2Carry out glycerine under the protection and separate the centrifugal then glycerine of removing.Esterification is under refluxad carried out, and with second, third, butyric acid, its consumption is 4.1kg earlier, and reaction 2.5h adopts acetic anhydride 1.5h then, and its consumption is 3.9kg, obtains crude product.Carry out refining steps such as alkali refining, dehydration at last, obtain finished product.The content of length chain acyl glyceride shared ratio in mixture is 83% (percentage by weight).In the long carbon chain fatty acid, saturated fatty acid: monounsaturated fatty acids: the ratio of polyunsaturated fatty acid is about 3: 4: 3 (mol ratio), and heat is 40% of a feedstock oil.
Embodiment 7:
Raw material is peanut oil and palm oil (1.779: 1, the mol ratio), and all the other steps are with example 6.The content of length chain acyl glyceride shared ratio in mixture is 75% (percentage by weight).In the long carbon chain fatty acid, saturated fatty acid: monounsaturated fatty acids: the ratio of polyunsaturated fatty acid is about 3: 4: 3 (mol ratio), and heat is 35% of a feedstock oil.
Claims (10)
1, a kind of low calorie fat; mixture for length chain acyl glyceride and common grease; it is characterized in that: length chain acyl glyceride normal temperature is down for liquid; at least one is the SCFA acyl group in the fatty acid acyl that three hydroxyls of length chain acyl glyceride link to each other, and long carbon chain fatty acid is the common fats acid that vegetable fat contained.Long carbon chain fatty acid is the common fats acid that vegetable fat contained, and saturated, single unsaturated, polyunsaturated fatty acid is arranged.Concrete steps are:
A. select a kind of vegetable fat for use; make that LCFA comprises saturated fatty acid, monounsaturated fatty acids, polyunsaturated fatty acid in the length chain acyl glyceride; or multiple grease interworking by a certain percentage, aliphatic acid is formed met the absorption of human body balance, as 3: 4: 3 (mol than).
B. vegetable oil and glycerine are reacted under certain condition.
C. the glycerine hydrolysis products is carried out esterification.
D. product is carried out refining treatment.
2, low calorie fat as claimed in claim 1, long carbon chain fatty acid wherein is specially laurate, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, leukotrienes etc., come from common vegetable oil, be generally soybean oil, peanut oil, rape seed oil, palm oil, safflower seed oil or by a certain percentage interworking form.
3, low calorie fat as claimed in claim 1, the content of length chain acyl glyceride wherein shared ratio in mixture is 10%～90% (percentage by weight), common content of oil and grease is 10%～90%.
4, low calorie fat as claimed in claim 1, the composition characteristic of length chain acyl glyceride wherein is LLS, LSL, SSL, SLS type triglycerides, and L refers to LCFA, can be chain saturated fatty acids, can be long-chain unsaturated fatty acid also, carbon number be between 12-24; S refers to SCFA, is acetate, propionic acid, butyric acid, can be one or more mixture wherein; The grease heat is compared with feedstock oil and has been reduced by 10%～40%.
5, as described in the claim 4, wherein the content of triglyceride of LLS, LSL type is 20%～70%; SSL, SLS type content of triglyceride are 30%～80%.
6, according to claim 1, glycerine is separated at phase transfer catalyst and is generally tetrabutylammonium chloride, TBAB, etamon chloride, hexadecyltrimethylammonium chloride, softex kw, and salt is generally Na
2SO
4, K
2SO
4
7, according to claim 1, glycerine is separated under 110 ℃～150 ℃ temperature and is carried out.
8, according to claim 1, esterification is reacted 2.0h～3.0h with 0.1～0.2 times of acetate, butyric acid or propionic acid or its mixture of substrate weight earlier; Adopt 0.1～0.15 times acetic anhydride, butyric anhydride or propionic andydride or its mixture reaction 1.0h～1.5h of substrate weight then.
9, according to claim 1, adopt soybean oil and palm oil by 1.2～2.5: 1 (mol ratio) interworking, length chain acyl glyceride is a saturated fatty acid: monounsaturated fatty acids: polyunsaturated fatty acid equals 3: 4: 3 (mol ratio).
10, according to claim 1, adopt peanut oil and palm oil with the certain proportion interworking, length chain acyl glyceride is a saturated fatty acid: monounsaturated fatty acids: polyunsaturated fatty acid=3: 4: 3 (mol ratio)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021235732A CN1292670C (en) | 2002-07-04 | 2002-07-04 | Liquid state low calorie fat mixed triglyceride |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021235732A CN1292670C (en) | 2002-07-04 | 2002-07-04 | Liquid state low calorie fat mixed triglyceride |
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| Publication Number | Publication Date |
|---|---|
| CN1465262A true CN1465262A (en) | 2004-01-07 |
| CN1292670C CN1292670C (en) | 2007-01-03 |
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|---|---|---|---|
| CNB021235732A Expired - Fee Related CN1292670C (en) | 2002-07-04 | 2002-07-04 | Liquid state low calorie fat mixed triglyceride |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101180995B (en) * | 2007-12-24 | 2011-05-11 | 钱生球 | Method for producing low calorie edible oil |
| CN102026551B (en) * | 2008-05-15 | 2013-04-17 | 日清奥利友集团株式会社 | Hard fat |
| CN103468756A (en) * | 2013-09-02 | 2013-12-25 | 东北农业大学 | Method for enzymatically synthesizing low-calorie triglyceride by using supercritical CO2 |
| CN103502410A (en) * | 2011-04-14 | 2014-01-08 | 阿尔法拉瓦尔股份有限公司 | A process for autocatalytic esterification of fatty acids |
| CN103535450A (en) * | 2013-09-30 | 2014-01-29 | 宁国市沙埠粮油加工厂 | Low-calorie edible oil and preparation method thereof |
| CN104054848A (en) * | 2013-03-19 | 2014-09-24 | 北京大华金润生物技术有限公司 | Novel edible oil with controllable glyceride content and preparation method thereof |
| CN104395449A (en) * | 2012-06-19 | 2015-03-04 | 诺瓦蒙特股份公司 | Process for the preparation of complex oligomeric structures |
| CN105602632A (en) * | 2016-01-06 | 2016-05-25 | 山东泰德新能源有限公司 | Biodiesel preparing method |
| CN106982939A (en) * | 2017-03-31 | 2017-07-28 | 海南思香源食品有限公司 | A kind of functional low caloric fat and preparation method thereof |
| CN110150666A (en) * | 2019-06-14 | 2019-08-23 | 广东省农业科学院蚕业与农产品加工研究所 | A kind of fat or oil composition and preparation method thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH31242A (en) * | 1990-10-19 | 1998-06-18 | Cpc International Inc | Reduced calory fat mimetics comprising esterified propoxylated monoglycerides and diglycerides. |
-
2002
- 2002-07-04 CN CNB021235732A patent/CN1292670C/en not_active Expired - Fee Related
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101180995B (en) * | 2007-12-24 | 2011-05-11 | 钱生球 | Method for producing low calorie edible oil |
| CN102026551B (en) * | 2008-05-15 | 2013-04-17 | 日清奥利友集团株式会社 | Hard fat |
| CN103502410A (en) * | 2011-04-14 | 2014-01-08 | 阿尔法拉瓦尔股份有限公司 | A process for autocatalytic esterification of fatty acids |
| US9085547B2 (en) | 2011-04-14 | 2015-07-21 | Alfa Laval Corporate Ab | Process for autocatalytic esterification of fatty acids |
| CN104395449A (en) * | 2012-06-19 | 2015-03-04 | 诺瓦蒙特股份公司 | Process for the preparation of complex oligomeric structures |
| CN104395449B (en) * | 2012-06-19 | 2017-03-29 | 诺瓦蒙特股份公司 | The preparation method of complicated oligomeric constituents |
| CN104054848A (en) * | 2013-03-19 | 2014-09-24 | 北京大华金润生物技术有限公司 | Novel edible oil with controllable glyceride content and preparation method thereof |
| CN103468756A (en) * | 2013-09-02 | 2013-12-25 | 东北农业大学 | Method for enzymatically synthesizing low-calorie triglyceride by using supercritical CO2 |
| CN103535450A (en) * | 2013-09-30 | 2014-01-29 | 宁国市沙埠粮油加工厂 | Low-calorie edible oil and preparation method thereof |
| CN105602632A (en) * | 2016-01-06 | 2016-05-25 | 山东泰德新能源有限公司 | Biodiesel preparing method |
| CN106982939A (en) * | 2017-03-31 | 2017-07-28 | 海南思香源食品有限公司 | A kind of functional low caloric fat and preparation method thereof |
| CN110150666A (en) * | 2019-06-14 | 2019-08-23 | 广东省农业科学院蚕业与农产品加工研究所 | A kind of fat or oil composition and preparation method thereof |
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| CN1292670C (en) | 2007-01-03 |
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