CN102018156B - Method of synthesizing phosphatide emulsifier for food - Google Patents
Method of synthesizing phosphatide emulsifier for food Download PDFInfo
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- CN102018156B CN102018156B CN2009100926339A CN200910092633A CN102018156B CN 102018156 B CN102018156 B CN 102018156B CN 2009100926339 A CN2009100926339 A CN 2009100926339A CN 200910092633 A CN200910092633 A CN 200910092633A CN 102018156 B CN102018156 B CN 102018156B
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Abstract
The invention relates to a method of synthesizing phosphatide emulsifier for food by using refined palm oil as raw material. The emulsifier is produced through semi-esterification, multiple phosphorus esterification reaction and hydroxylation reaction successively. The invention is characterized in that: the source of the raw material for the invention is abundant and cheap, the quality of the product is stable for each batch, the product not only has a similar structure with natural phosphatide but also has good emulsifying property, the operation is simple, the synthetic route is short, the productivity is high and industrial production is easy to realize.
Description
Technical field
The present invention relates to a kind of synthetic method of phospholipid emulsifying agent, specifically relating to a kind of is feedstock production with the palm oil, has the good food of natural phospholipid complete structure and emulsifiability with the synthetic method of phospholipid emulsifying agent.
Background technology
Emulsifying agent is the stabilizing agent of emulsion, is the surfactant that a class has hydrophilic group and lipophilic group.When it is dispersed in dispersate surperficial, form film or electric double layer, can make decentralized photo have electric charge, so just can stop the droplet of decentralized photo to condense mutually, make the emulsion of formation more stable.Because it can make immiscible two-phase (as oil and water) miscible mutually, and forms homogeneous dispersion or emulsified body, thereby change original physical state.Along with the lifting of foods processing technique, make emulsifying agent in food processing process, play the part of considerable role, be subjected to curing the dealer and extensively pay attention to, and in baked product, widely utilize, and then change the internal structure of product, improved product quality.
An amount of emulsifying agent that adds has not only improved the internal structure of the product that cure, and has made baking quality more stable.Thereby the demand of emulsifying agent has the trend of progressively rising in world markets, and the consumption of 1 year emulsifying agent of the U.S. can reach 5,000,000 U.S. dollars.And the market of emulsifying agent maximum is bread industry, and wherein nearly 50% is single glyceride.The world wide production industry in soybean lecithin every year has surprising potentiality in continuous rising in Western-style pastry and leisure food.
Phosphatide mainly comprises phosphatid ylcholine (lecithin) as the insoluble phosphorous complex mixture of a kind of acetone, ethylaminoethanol phosphatide (cephalin), materials such as phosphatidylinositols (lipositol) and sweet three esters, aliphatic acid and carbohydrate.By chemical constitution, phosphatide is aliphatic acid, the derivative of compounds such as glycerine and phosphoric acid.As the phospholipid that contains that is present in living nature, it with grease and deposit, is the essential material that constitutes cell basic structure in seed, animal blood and internal organs, yolk and the bacterium of plant.Transmission for oxygen in the permeability of keeping cell and the cell plays an important role, and also is one of basic substance of life.Phosphatide is except above-mentioned physiological function, also has extremely strong emulsification, and have certain nutrient value and medical function concurrently, it is the emulsifying agent of significant and development, but when using as surfactant, the food that natural phospholipid and fatty acid monoglyceride, sucrose fatty ester, polyglyceryl fatty acid ester etc. are softer adds surfactant and compares, having HLB value (Hydrophile-Lipophile Balance Number) is hydrophilic hydrophobic balance value little (being about 3～4), hydrophily is poor, is difficult for shortcomings such as dispersion at aqueous phase.
The molecular structure of synthetic phospholipid can carry out MOLECULE DESIGN according to different purposes and requirement, makes synthetic phospholipid present structure, the diversified characteristics of performance, can effectively remedy natural phospholipid in the deficiency of some aspect of performance.China uses more widely, and food emulsifier is modified soy bean lipoid.But remaining in a lot of deficiencies aspect the purification of phosphatide and the chemical modification.For food phospholipid emulsifying agent, be by the middle level separator of centrifugal extraction fresh soyabean oil foot mostly at present, it is fully mixed with acetone, obtain soybean lecithin through decompress filter, vacuum drying.Contain saturated or undersaturated fatty acid chain in phospholipid molecule, the epoxidation reaction by to carbon-carbon double bond makes intermediate feed, further carries out ring-opening reaction synthesis modification phosphatide.Thisly directly extract rough phosphatide from soybean oil residue, carry out oxidation modification then, though improved the emulsifying capacity of phospholipid of natural soybean, end product easily lumps, the easily moisture absorption, easily oxidation, purity is not high, impurity is more.
The food of suitability for industrialized production mainly contains concentrated phosphatide, powder phospholipid, modified phospholipid (hydroxylating, acyl groupization, hydroxyl acidylate, enzyme modification phosphatide etc.) with the phospholipid emulsifying agent at present.Concentrated phosphatide is generally the concentrated soybean phospholipid that hydrated oil foot that hydration degum operation in the soybean oil refining process produces obtains through processed, because it contains part neutral oil, aliphatic acid and other impurity, easy oxidation discoloration is the rufous viscous fluid, and emulsifying capacity is relatively poor, smell is bad.Powder phospholipid is to be solvent with acetone, concentrated phosphatide is raw material, the light color that obtains through hybrid extraction, centrifugation, vacuum drying does not have oil, free from extraneous odour, the higher phosphatide solid product of purity, but its HLB value is lower, the chemical property of hydrophily difference does not change.In order to improve the hydrophily of natural phospholipid, it has been carried out phospholipid modified research, acetylation, hydroxylating, hydroxyl acidylate, enzyme modification phospholipid prod have been realized suitability for industrialized production.But because phosphatide applied range in food service industry, produce phosphatide and do not satisfy industrial demand far away to be extracted as means, therefore need to pass through manual method and be synthesized, to satisfy food industry to its demand.
Summary of the invention
The objective of the invention is at deficiency of the prior art, the synthetic method of the food usefulness phospholipid emulsifying agent that a kind of emulsifiability is good, product purity is high is provided.
For reaching above-mentioned purpose, the present invention has adopted following technical scheme:
A kind of food synthetic method of phospholipid emulsifying agent, it is raw material with the refining palm oil, is prepared from through half ester reaction, polynary phosphatide reaction and hydroxylating successively.
The present invention also can further realize by following technical solution:
The described food synthetic method of phospholipid emulsifying agent, wherein, described half ester reaction is the half ester exchange reaction that refining palm oil and lower alcohol carry out under the ester exchange catalyst effect, gets palm oil half ester exchange product; Described polynary phosphatide reaction is to add phosphatide reagent in palm oil half ester exchange product, introduces the phosphatide base, gets the raw phospholipid product; Described hydroxylating is to add hydrogen peroxide in the raw phospholipid product, epoxidation reaction takes place under the effect of lactic acid, again the epoxidation afterproduct is added the NaOH neutralization, then with the vacuum dehydration of phosphatide product to the product water content below 1.5%, the milk yellow block that makes is food phospholipid emulsifying agent.
The described food synthetic method of phospholipid emulsifying agent, wherein, described half ester exchange reaction is ester exchange catalyst directly to be joined in refining palm oil and the lower alcohol mixture react, the palmitic mass ratio of lower alcohol and refining is 1: 0.05～0.1, catalyst amount is 1～5% of reaction substrate gross mass, reaction temperature is 110 ℃～130 ℃, and the reaction time is 4～5 hours.
Described food is with the synthetic method of phospholipid emulsifying agent, and wherein, described lower alcohol is wherein a kind of or their mixture in ethylene glycol, the propane diols, and the former with the latter ratio is 1: 0.5～1 during for mixture; Described ester exchange catalyst is 98% industrial sulphuric acid.
The described food synthetic method of phospholipid emulsifying agent, wherein, described phosphatide reaction is phosphatide reagent directly slowly to be joined in the palm oil half ester exchange product at 30～40 ℃ to react, and reagent adds and temperature risen to 60～65 ℃, 1～2 hour reaction time after finishing.
The described food synthetic method of phospholipid emulsifying agent, wherein, described phosphatide reagent is phosphorus pentoxide or POCl3, the palmitic mass ratio of addition by phospholipase reagent and raw material is 0.25～0.5: 1.
The described food synthetic method of phospholipid emulsifying agent, wherein, described hydroxylating is that the raw phospholipid product is added lactic acid under the condition of agitating heating, and then adding concentration is that 30% hydrogenperoxide steam generator reacts, the addition of lactic acid is phosphatide product weight 2%～3%, and the hydrogenperoxide steam generator addition is raw phospholipid product weight 5%-15%, 80 rev/mins of mixing speeds, 50～70 ℃ of reaction temperatures, 1～3 hour reaction time; Product is cooled to 50 ℃ then, is neutralized to neutrality with 10% sodium hydroxide solution, vacuum dehydration to water content below 1.5%, gained milk yellow block is food phospholipid emulsifying agent.
Described food is with the synthetic method of phospholipid emulsifying agent, wherein, in adding sodium hydroxide solution and the time, add the molecular clock monoglyceride that accounts for total weight of material 10%～20% simultaneously, mix the back cooling, vacuum dehydration.
The described food synthetic method of phospholipid emulsifying agent, wherein, food is carried out processing and forming with the milk yellow block of phospholipid emulsifying agent, through section, be crushed to 200 orders after the vacuum freezedrying, send into the warehouse for finished product packing then and namely obtain finished product food phospholipid emulsifying agent.
The described food synthetic method of phospholipid emulsifying agent, wherein, described refining palm oil is removed free fatty for the edible refining palm olein oil that will meet GB GB/T 15680-1995 with sodium hydroxide solution under 80 ℃ of conditions, washing removal Chinese honey locust is prepared from then; Described lactic acid is food-grade, and purity is greater than 92%; Described hydrogen peroxide is food-grade; Described NaOH is food-grade, and the sheet alkali content is greater than 99%; Described molecular clock monoglyceride is food-grade, monoglyceride content 〉=90%.
Owing to adopted above technical scheme, the present invention possesses following technique effect:
(1) to adopt the refining palm oil be raw material in the present invention, palm oil contains the balanced proportion of saturated fatty acid and unrighted acid, nearly 44% palmitic acid, 5% stearic acid (two kinds are saturated acid), 40% oleic acid (unsaturated acids), 10% linoleic acid and 0.4% alpha-linolenic acid (two kinds all is polyunsaturated acid).This natural combination makes palm oil have great stability, is difficult for oxidizedly, is raw material with it, can improve the oxidation stability of synthetic phospholipid product.In addition, palm oil source is enriched, is easy to get, price is low, has avoided the raw material supply instability to the influence that phospholipid prod brings, and is conducive to guarantee the stability of product batches.
(2) products therefrom---food adopts mixed indicator method and potentiometric titration to analyze its composition with the phospholipid emulsifying agent, wherein contains polyester 60.2～65.3%, dibasic acid esters 18.5～22.5%, monoesters 11.3～19.8%, hetero atom phosphatide 1.1～2.3%; Measuring its HLB value with the cloud point method is 10.4～12.2; Thereby it has possessed the structure similar to natural phospholipid as can be seen, and its emulsifiability is good than natural phospholipid.
(3) carrying out half ester exchange reaction formula, under the normal pressure, 120 ℃, the saturation solubility of ester exchange catalyst in grease is very little, its reaction is reversible reaction, so for utilizing the reaction of system and mass transfer, heat transfer, in the preparation, the present invention makes excessive lower alcohol and the palmitic mass ratio of refining namely controlled of grease 0.05～0.2: 1, guarantee carrying out smoothly of half ester exchange reaction, avoided because of backward reaction to the loss of raw material and the decline of productive rate;
(4) in the half ester exchange reaction, when reaction temperature reached 90 ℃, along with the rising of temperature, the conversion ratio of grease increased fast, and after 120 ℃, the conversion ratio increase of grease is no longer obvious, and continue to heat this moment, and product colour will deepen.For the proterties that guarantees grease conversion ratio and product is stablized, so the control reaction temperature has effectively been taken into account production efficiency and product characteristics between 110～130 ℃;
(5) this synthetic method is by ester exchange reaction with introduce phosphorus-containing groups with preparation phospholipid emulsifying agent, and this method is easy and simple to handle, synthetic route is short, productive rate is high, easily separated, less demanding to production equipment, is easy to suitability for industrialized production.
The specific embodiment
Palm olein oils are spent available from 24 of the extra large grain and oil of benefit Industrial Co., Ltd by palm oil system used among the following embodiment; Used NaOH is food-grade, and the sheet alkali content is 99%; Used ethylene glycol, propane diols, the concentrated sulfuric acid, phosphorus pentoxide are food-grade; Used lactic acid is food-grade, and purity is greater than 92%; Used hydrogen peroxide is food-grade, and concentration is 30%; Described molecular clock monoglyceride is food-grade, and monoglyceride content meets food additives standard GB 15162-1995 more than or equal to 90%.
Embodiment 1:
A kind of food comprises the steps: with the synthetic method of phospholipid emulsifying agent
(1) the raw material palm oil is refining:
Be that 40% sodium hydroxide solution joins in the 800KG outsourcing refining palm oil with 8KG concentration, in reactor, stirred 30 minutes under 80 ℃, left standstill 1 hour that tell end slag to remove free fatty, supernatant stays standby;
(2) palm oil half ester exchange:
With exchanger---the weighing of 80KG ethylene glycol joins in the supernatant of retaining in the reactor described in (1), stirs and is warming up to 110 ℃, adds 25KG ester exchange catalyst---the concentrated sulfuric acid again, continue to stir, temperature maintenance was reacted 4 hours at 110 ℃, got palm oil half ester exchange product;
(3) polynary phosphatide reaction:
Cool to 35 ℃ ± 5 ℃, slowly add the 300KG phosphorus pentoxide then, the joining day is about 3 hours, treat that phosphorus pentoxide all adds after, temperature is risen to 60 ℃ of insulations continues reaction 1 hour, get the raw phospholipid product;
(4) hydroxylating:
When being cooled to 55 ℃ ± 5 ℃, (3) middle gained raw phospholipid product adds the 250KG hydrogen peroxide, stirring reaction 2 hours, then its product is cooled to 50 ℃, slowly adding concentration in it is that 10% sodium hydroxide solution is neutralized to neutrality, stirring reaction, rotating speed control is at 80rpm, open big condensed water simultaneously, keep lower neutral temperature, for improving emulsifying capacity, also can add 160KG molecular clock monoglyceride simultaneously, thawing while hot mixes, and cooling back gained milk yellow block is food phospholipid emulsifying agent.
(5) forming process
With above-mentioned milk yellow block section, vacuum freezedrying is ground into 200 order left and right sides fine powders and is finished product synthetic phospholipid emulsifying agent.Adopt mixed indicator method and potentiometric titration to analyze its composition, wherein contain polyester 62.8%, dibasic acid esters 19.1%, monoesters 16%, contain hetero atom phosphatide 1.53%.Measuring product hydrophilic lipophilic balance (HLB value) with the cloud point method is 11.4.
Embodiment 2:
A kind of food comprises the steps: with the synthetic method of phospholipid emulsifying agent
(1) the raw material palm oil is refining:
Described with embodiment 1.
(2) palm oil half ester exchange:
With joining in the supernatant of retaining in the reactor described in (1) after exchanger ethylene glycol, each 40KG metering of propane diols, stir and be warming up to 120 ℃, add 25KG ester exchange catalyst--H2SO4 while stirring, reacted 5 hours.
(3) polynary phosphatide reaction:
Cool to 35 ℃ ± 5 ℃, slowly add the 350KG phosphorus pentoxide then, the joining day is about 3 hours, treat that phosphorus pentoxide all adds after, temperature is risen to 65 ℃ of insulations continues reaction 1 hour, get the raw phospholipid product.
(4) hydroxylating:
When being cooled to 55 ℃ ± 5 ℃, (3) middle gained raw phospholipid product adds the 300KG hydrogen peroxide, stirring reaction 2 hours, then its product is cooled to 50 ℃, slowly adding concentration in it is that 10% sodium hydroxide solution is neutralized to neutrality, stirring reaction, rotating speed control is at 80rpm, open big condensed water simultaneously, keep lower neutral temperature, for improving emulsifying capacity, also can add 200KG molecular clock monoglyceride simultaneously, thawing while hot mixes, and cooling back gained milk yellow block is food phospholipid emulsifying agent.
(5) forming process
Described with example 1.
Products obtained therefrom adopts mixed indicator method and potentiometric titration to analyze its composition, contains polyester 63%, dibasic acid esters 20.3%, monoesters 14.5%, contains hetero atom phosphatide 1.19%.Measuring product hydrophilic lipophilic balance (HLB value) with the cloud point method is 12.2.
Example 3
A kind of food comprises the steps: with the synthetic method of phospholipid emulsifying agent
(1) the raw material palm oil is refining:
With example 1,2 described.
(2) palm oil half ester exchange:
Exchanger---the weighing of 80KG propane diols joins in the supernatant of retaining in the reactor described in (1), stirs and is warming up to 130 ℃, adds 25KG ester exchange catalyst---the concentrated sulfuric acid again, continue to stir, temperature maintenance was reacted 5 hours at 130 ℃, got palm oil half ester exchange product;
(3) polynary phosphatide reaction:
Cool to 35 ℃ ± 5 ℃, slowly add the 400KG phosphorus pentoxide then, the joining day is about 3 hours, treat that phosphorus pentoxide all adds after, temperature is risen to 65 ℃ of insulations continues reaction 2 hours, get the raw phospholipid product.
(4) hydroxylating:
When being cooled to 55 ℃ ± 5 ℃, (3) middle gained raw phospholipid product adds the 300KG hydrogen peroxide, stirring reaction 2 hours, then its product is cooled to 50 ℃, slowly adding concentration in it is that 10% sodium hydroxide solution is neutralized to neutrality, stirring reaction, rotating speed control is at 80rpm, open big condensed water simultaneously, keep lower neutral temperature, for improving emulsifying capacity, also can add 240KG molecular clock monoglyceride simultaneously, thawing while hot mixes, and cooling back gained milk yellow block is food phospholipid emulsifying agent.
(6) forming process
With example 1.
Adopt mixed indicator method and potentiometric titration to analyze its composition, contain ester 65.1%, dibasic acid esters 22.15%, monoesters 11.33% in the products obtained therefrom, contain hetero atom phosphatide 1.21%.Measuring product hydrophilic lipophilic balance (HLB value) with the cloud point method is 10.4.
Claims (4)
1. a food is characterized in that with the synthetic method of phospholipid emulsifying agent:
Be raw material with the refining palm oil, be prepared from through half ester reaction, polynary phosphatide reaction and hydroxylating successively;
Described half ester reaction is the half ester exchange reaction that refining palm oil and lower alcohol carry out under the ester exchange catalyst effect, gets palm oil half ester exchange product;
Described polynary phosphatide reaction is to add phosphatide reagent in palm oil half ester exchange product, introduces the phosphatide base, gets the raw phospholipid product;
Described hydroxylating is to add hydrogen peroxide in the raw phospholipid product, epoxidation reaction takes place under the effect of lactic acid, again the epoxidation afterproduct is added the NaOH neutralization, then with the vacuum dehydration of phosphatide product to water content below 1.5%, the milk yellow block that makes is food phospholipid emulsifying agent;
Described half ester exchange reaction is ester exchange catalyst directly to be joined in refining palm oil and the lower alcohol mixture react, the palmitic mass ratio of lower alcohol and refining is 0.05～0.2: 1, catalyst amount is 1～5% of reaction substrate gross mass, reaction temperature is 110 ℃～130 ℃, and the reaction time is 4～5 hours;
Described lower alcohol is wherein a kind of or their mixtures in ethylene glycol, the propane diols, and the former with the latter ratio is 1: 0.5～1 during for mixture; Described ester exchange catalyst is 98% industrial sulphuric acid;
Described phosphatide reaction is phosphatide reagent directly slowly to be joined in the palm oil half ester exchange product at 30～40 ℃ to react, and reagent adds and temperature risen to 60～65 ℃, 1～2 hour reaction time after finishing;
Described phosphatide reagent is phosphorus pentoxide or POCl3, and the palmitic mass ratio of addition by phospholipase reagent and raw material is 0.25～0.5: 1;
Described hydroxylating is that the raw phospholipid product is added lactic acid under the condition of agitating heating, and then adding concentration is that 30% hydrogenperoxide steam generator reacts, the addition of lactic acid is raw phospholipid product weight 2%～3%, the hydrogenperoxide steam generator addition is raw phospholipid product weight 5%～15%, 80 rev/mins of mixing speeds, 50～70 ℃ of reaction temperatures, 1～3 hour reaction time; Product is cooled to 50 ℃ then, is neutralized to neutrality with 10% sodium hydroxide solution, vacuum dehydration to water content below 1.5%, gained milk yellow block is food phospholipid emulsifying agent;
Described refining palm oil adopts following method preparation: the edible refining palm olein oil that will meet GB GB/T15680-1995 is removed free fatty with sodium hydroxide solution under 80 ℃ of conditions, and washing removal Chinese honey locust is prepared from then.
2. food according to claim 1 is characterized in that with the synthetic method of phospholipid emulsifying agent:
In adding sodium hydroxide solution and the time, add the molecule distillating monoglyceride that accounts for total weight of material 10%-20% simultaneously, mix the back cooling, vacuum dehydration.
3. food according to claim 1 is characterized in that with the synthetic method of phospholipid emulsifying agent:
Food is carried out processing and forming with the milk yellow block of phospholipid emulsifying agent, through section, be crushed to 200 orders after the vacuum freezedrying, send into the warehouse for finished product packing then and namely obtain finished product food phospholipid emulsifying agent.
4. use the synthetic method of phospholipid emulsifying agent according to arbitrary described food among the claim 1-3, it is characterized in that:
Described lactic acid is food-grade, and purity is greater than 92%; Described hydrogen peroxide is food-grade; Described NaOH is food-grade, and the sheet alkali content is greater than 99%; Described molecule distillating monoglyceride is food-grade, content of monoglyceride 〉=90%.
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