CN106083577A - A kind of preparation method and application of methyl glycol fatty acid ester - Google Patents
A kind of preparation method and application of methyl glycol fatty acid ester Download PDFInfo
- Publication number
- CN106083577A CN106083577A CN201610415639.5A CN201610415639A CN106083577A CN 106083577 A CN106083577 A CN 106083577A CN 201610415639 A CN201610415639 A CN 201610415639A CN 106083577 A CN106083577 A CN 106083577A
- Authority
- CN
- China
- Prior art keywords
- fatty acid
- acid ester
- methyl glycol
- glycol fatty
- preparation
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Abstract
The invention discloses the preparation method and application of a kind of methyl glycol fatty acid ester.Described preparation method includes S1, respectively by 1,2 propylene glycol and fatty acid filter after adding heat fusing；S2, by 1,2 propylene glycol suction reactors, add base catalyst, stirring mixing, then by fatty acid suction reactor, control reaction temperature be 180～200 DEG C, vacuum is 0.06～0.08MPa, carries out esterification；S3, esterification terminate, cooling discharge, prepare methyl glycol fatty acid ester；Described fatty acid is Palmic acid, oleic acid and linoleic mixture, and described Palmic acid, oleic acid and linoleic weight ratio are (3～5): (2～4): 1.The inventive method can industrialized mass, and technique is simple, condition is easily-controllable, and the methyl glycol fatty acid ester prepared is applied in cake, can improve characteristics of cake.
Description
Technical field
The invention belongs to chemical field, be specifically related to the preparation method and application of a kind of methyl glycol fatty acid ester.
Background technology
Methyl glycol fatty acid ester is the food additive of a class synthetic of exploitation the 1950's, and it has well
Foaminess and emulsifiability, its foaming capacity depends on monoester content, and monoester content is the highest, and performance is the best, and it is commonly used for
Cake and the foaming agent of cream cake.Methyl glycol fatty acid ester as food emulsifying agent, its consumption be only second to abroad monoglyceride,
The kind such as sorbitan ester, soybean phospholipid, is one of big food emulsifying agent in the world six.
At present, the synthetic method of methyl glycol fatty acid ester mainly has two kinds: (1) is being catalyzed by fatty acid and 1,2-PD
Direct esterification under agent, has use acidic catalyst, such as concentrated sulphuric acid, toluene sulfonic acide, solid super-strong acid SO4 2-Fe2O3, also have use
Base catalyst, such as potassium carbonate, calcium oxide, sodium carbonate etc.；(2) 1,2-PD and oils and fats carry out ester friendship under base catalyst
Change reaction.The product of both approaches is all the mixture of monoesters and dibasic acid esters, and monoester content is commonly 40～70%, therefore, base
In the limitation of current preparation method, cause methyl glycol fatty acid ester foaminess and emulsibility to can not get effectively and improve, need with
Single bis-fatty acid glyceride etc. with the use of, to play a potentiation.Thus, it is necessary on the basis of existing technology, further
Optimize the parameter such as reaction raw materials, reaction condition and operation to promote foaminess and the emulsibility of methyl glycol fatty acid ester.
Chinese patent CN 101225044B discloses a kind of methyl glycol fatty acid ester, and it is by propylene glycol and A, B and C tri-kinds
Fatty acid is that raw material is esterified under base catalyst and forms, and wherein raw material A is acetic acid, butanoic acid, and raw material B is valeric acid, caproic acid, raw material
C is at least three kinds in Palmic acid, oleic acid, linoleic acid, stearic acid.This methyl glycol fatty acid ester adds in milk product, has auxiliary
Help the effect of flavouring, milk product is also had Stabilization simultaneously.But the complicated component of this methyl glycol fatty acid ester, simultaneously its system
Standby process is loaded down with trivial details, and energy consumption is big, and the time is long, and can produce substantial amounts of impurity, have impact on its foaminess in cake, cake etc.
Energy.
Summary of the invention
In order to overcome the deficiencies in the prior art, first purpose of the present invention is to provide a kind of methyl glycol fatty acid ester
Preparation method, the method is simple, condition is easily-controllable, energy consumption is low, and the methyl glycol fatty acid ester impurity prepared is few, has well foaming
Property.
To achieve these goals, technical scheme is as follows:
The preparation method of a kind of methyl glycol fatty acid ester, specifically includes following steps:
S1,1,2-PD and fatty acid are added filter after heat fusing respectively；
S2, by 1,2-PD suction reactor, add base catalyst, stirring mixing 30～40min, then by fat
Acid suction reactor, control reaction temperature be 180～200 DEG C, vacuum is 0.06～0.08MPa, carry out esterification 1～
2h；
S3, esterification terminate, and are cooled to 100 DEG C of dischargings, prepare methyl glycol fatty acid ester；
Described fatty acid is Palmic acid, oleic acid and linoleic mixture, described Palmic acid, oleic acid and linoleic weight
Than being (3～5): (2～4): 1.
Further, the weight ratio of described 1,2-PD and fatty acid is 1:(2～3).
Further, the one or many during described base catalyst is sodium carbonate, sodium bicarbonate, sodium hydroxide and potassium carbonate
Kind.
Further, the addition of described base catalyst is the 3～6% of 1,2-PD weight.
The present invention is also claimed the methyl glycol fatty acid ester product prepared by above-mentioned preparation method, and this propylene glycol
Fatty acid ester product application in cake.
Level based on prior art, inventor has drawn technical scheme through constantly test and research.
Wherein, preparation method of the present invention by Palmic acid, oleic acid and linoleic acid by weight (3～5): (2～4): 1 combines the mixing obtained
Thing and 1,2-PD react by a certain percentage, under certain condition and prepare methyl glycol fatty acid ester, this process simplify existing
The reaction raw materials of technology and reactions steps, reduce reaction temperature, shortens the response time, and the methyl glycol fatty acid ester prepared
Impurity is few, not only keeps good emulsifying capacity, becomes apparent from improving its foam performance, has widened its range of application.Particularly
Combined the mixture obtained by Palmic acid, oleic acid and linoleic acid by weight 4:3:1, react prepared the third two with 1,2-PD
The application best results of alcohol fatty acid ester product.
Therefore, compared with prior art, present invention have an advantage that
The preparation method of methyl glycol fatty acid ester of the present invention can produce to industrial mass the propylene glycol fatty of high-quality
Acid esters, its technique is simple, condition is easily-controllable, production cost is low, can be applicable.The propylene glycol monostearate that the inventive method prepares
Ester impurity is few, is applied in cake, can significantly improve characteristics of cake, increases cake volume, and the tissue making cake is fine and smooth, bulk easypro
Soft.
Detailed description of the invention
Further describe the present invention below by way of detailed description of the invention, but the present invention is not limited only to following example.?
In the scope of the present invention or without departing from present disclosure, spirit and scope, the present invention is suitably modified, replaces
The component that effect is identical, apparent to those skilled in the art, they are considered as being included in the scope of the invention
In.
Embodiment 1, the preparation method of methyl glycol fatty acid ester of the present invention
S1,100kg 1,2-PD and 200kg fatty acid are added filter after heat fusing respectively；
S2, by 1,2-PD suction reactor, add 3kg sodium hydroxide, stirring mixing 30min, then by fatty acid
Suction reactor, controlling reaction temperature is 180 DEG C, and vacuum is 0.06MPa, carries out esterification 1h；
S3, esterification terminate, and are cooled to 100 DEG C of dischargings, prepare methyl glycol fatty acid ester；
Described fatty acid is the mixture that Palmic acid, oleic acid and linoleic acid are mixed to get by weight 3:2:1.
Embodiment 2, the preparation method of methyl glycol fatty acid ester of the present invention
S1,100kg 1,2-PD and 300kg fatty acid are added filter after heat fusing respectively；
S2, by 1,2-PD suction reactor, add 6kg sodium bicarbonate, stirring mixing 40min, then by fatty acid
Suction reactor, controlling reaction temperature is 200 DEG C, and vacuum is 0.08MPa, carries out esterification 2h；
S3, esterification terminate, and are cooled to 100 DEG C of dischargings, prepare methyl glycol fatty acid ester；
Described fatty acid is the mixture that Palmic acid, oleic acid and linoleic acid are mixed to get by weight 5:4:1.
Embodiment 3, the preparation method of methyl glycol fatty acid ester of the present invention
S1,100kg 1,2-PD and 250kg fatty acid are added filter after heat fusing respectively；
S2, by 1,2-PD suction reactor, add 4kg sodium carbonate, stirring mixing 40min, then fatty acid taken out
Entering reactor, controlling reaction temperature is 190 DEG C, and vacuum is 0.08MPa, carries out esterification 1h；
S3, esterification terminate, and are cooled to 100 DEG C of dischargings, prepare methyl glycol fatty acid ester；
Described fatty acid is the mixture that Palmic acid, oleic acid and linoleic acid are mixed to get by weight 4:3:1.
Embodiment 4, the preparation method of methyl glycol fatty acid ester of the present invention
S1,100kg 1,2-PD and 250kg fatty acid are added filter after heat fusing respectively；
S2, by 1,2-PD suction reactor, add 5kg sodium carbonate, stirring mixing 40min, then fatty acid taken out
Entering reactor, controlling reaction temperature is 200 DEG C, and vacuum is 0.06MPa, carries out esterification 1h；
S3, esterification terminate, and are cooled to 100 DEG C of dischargings, prepare methyl glycol fatty acid ester；
Described fatty acid is the mixture that Palmic acid, oleic acid and linoleic acid are mixed to get by weight 5:2:1.
Comparative example 1
In this comparative example, described fatty acid is the mixing that Palmic acid, oleic acid and linoleic acid are mixed to get by weight 1:1:1
Thing.Other parameters and operation are with embodiment 3.
Comparative example 2
In this comparative example, described fatty acid is Palmic acid and the oleic acid mixture that 4:3 is mixed to get by weight.Other ginsengs
Number and operation are with embodiment 3.
Comparative example 3
The methyl glycol fatty acid ester prepared with reference to Chinese patent CN 101225044B embodiment 1.
Test example one
The index of the methyl glycol fatty acid ester that embodiment 1～4 prepares is detected, uses health ministry specified value
" food additive methyl glycol fatty acid ester " is analyzed, and product index and analysis method see table 1 below.Result see table 2.
The index of table 1 methyl glycol fatty acid ester and the method for analysis
| Project | Index | The method of inspection |
| Acid number (in terms of KOH)/(mg/g)≤ | 4 | In appendix A A.2 |
| Free propylene glycol, w/%≤ | 1.5 | GB1986 dissociative glycerin |
| Iodine number | Meet nominal | GB/T18953 |
| Ignition residue, w/%≤ | 0.5 | GB/T9741 |
| Saponification number | Meet nominal | GB/T5534 |
| Total monoester content, w/% | It is not less than nominal | In appendix A A.4 |
| Lead (Pb)/(mg/kg)≤ | 2 | GB5009.12 |
The Indexs measure result of table 2 each embodiment methyl glycol fatty acid ester
| Index name | Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 |
| Acid number (in terms of KOH)/(mg/g) | 3.1 | 3.7 | 2.0 | 2.8 |
| Free propylene glycol, w/% | 1.2 | 0.9 | 0.3 | 1.4 |
| Iodine number | Meet nominal | Meet nominal | Meet nominal | Meet nominal |
| Ignition residue, w/% | 0.5 | 0.4 | 0.4 | 0.3 |
| Saponification number | Meet nominal | Meet nominal | Meet nominal | Meet nominal |
| Total monoester content, w/% | It is not less than nominal | It is not less than nominal | It is not less than nominal | It is not less than nominal |
| Lead (Pb)/(mg/kg) | 1.2 | 1.6 | 0.7 | 0.9 |
From upper table 2, each index of the methyl glycol fatty acid ester that the inventive method prepares all reaches Ministry of Public Health and specifies mark
Accurate.
Test example two
1, the preparation of milk drink: dissolving+milk powder → allotment → homogenizing → sterilization cooling → inspection after sugar, additives dry blended
→ finished product.Milk drink basic recipe see table 3.
Table 3 milk drink basic recipe
| Raw material | Ratio/% |
| Full-grease milk powder | 5.0 |
| Sucrose | 2.0 |
| Emulsifying agent (is specifically shown in table 4 below) | 0.10 |
| Xanthan gum | 0.025 |
| Water | To 100 |
2, the stability of milk drink and sensory evaluation
The milk drink prepared by different emulsifiers is diluted 80 times, measures under 540nm wavelength with 721 spectrophotometers
Sample absorbance value A1；Then it is centrifuged 5min with table model high speed centrifuge 4000r/min, under phase co-wavelength, measures centrifugal rear sample
The absorbance A of product2.Weigh the principle of emulsifier effect quality with light absorption value, mainly by protein particulate and
The birefringent phenomenon of Oil globule.Protein particulate and Oil globule are the least, are distributed the most uniform, and absorbance is the biggest；Protein
Grain and Oil globule are the biggest, agglomeration occur more, is distributed the most uneven, and absorbance is the least.If R (coefficient of stability)=
A2/A1(R 1), R value is the biggest, illustrates that the emulsifiability of emulsifying agent is the best, carries out sensory evaluation simultaneously.
Result see table 4.
Table 4 milk drink comprehensive evaluation result
| Emulsifying agent | A<sub>1</sub> | A<sub>2</sub> | R | Sensory evaluation |
| Embodiment 1 | 0.812 | 0.680 | 0.837 | Pure flavor, smooth mouth feel |
| Embodiment 2 | 0.837 | 0.694 | 0.829 | Pure flavor, smooth mouth feel |
| Embodiment 3 | 0.852 | 0.731 | 0.858 | Pure flavor, smooth mouth feel |
| Embodiment 4 | 0.807 | 0.685 | 0.849 | Pure flavor, smooth mouth feel |
| Comparative example 3 | 0.836 | 0.701 | 0.838 | Pure flavor, smooth mouth feel |
From upper table 4, with the addition of the embodiment of the present invention 1～4 methyl glycol fatty acid ester milk drink as emulsifying agent
Coefficient of stability R value big, good stability, sensory evaluation simultaneously is good, illustrates that methyl glycol fatty acid ester of the present invention can be effectively improved
The stability of milk drink system, will not produce impact to the local flavor of beverage simultaneously.
Test example three
The evaluation of cake quality typically uses full matter structure analysis, the hardness of Main Analysis cake, elasticity, recovery and chew
Property.In general, hardness and the chewiness of cake are the least, elastic and recovery is the biggest, and the quality of cake is the best.
Table 5 spongecake basic recipe
| Flour (g) | Soft plantation white sugar (g) | Egg (g) | Baking powder (g) | Vegetable oil (g) | Emulsifying agent (g) |
| 110 | 99 | 176 | 1.8 | 3 | 3 |
Using embodiment 1～4 and the methyl glycol fatty acid ester of comparative example 1～3 apply above-mentioned table 5 sponge respectively as emulsifying agent
In cake basic recipe, if one group of blank group not applying emulsifying agent, identical method is used to make spongecake.Make
After spongecake, first measure its baked volume, then use AACC (74-09) international standard, spongecake sample is cut into
Identical thickness, and guarantee have even curface and bottom surface, remove the hard edge of sample simultaneously.Measure probe to use
The flat column type of AACC25mm is popped one's head in, speed 1.0mm/s, speed of experiment 1.7mm/s, return speed 2.0mm/s, measuring distance before experiment
10mm, induction force Auto-5g, data are counted 250pps.Each sample parallel measures 3 times, takes its meansigma methods, result such as table 6 below.
Table 6 cake full matter structure testing result
| Emulsifying agent | Baked volume (cm<sup>3</sup>) | Hardness (g) | Elastic | Chewiness | Recovery |
| Embodiment 1 | 2290 | 187.094 | 0.803 | 96.937 | 0.352 |
| Embodiment 2 | 2200 | 190.391 | 0.818 | 92.602 | 0.323 |
| Embodiment 3 | 2485 | 174.472 | 0.856 | 84.523 | 0.369 |
| Embodiment 4 | 2042 | 192.650 | 0.832 | 97.385 | 0.330 |
| Comparative example 1 | 1741 | 217.533 | 0.703 | 114.460 | 0.302 |
| Comparative example 2 | 1550 | 228.768 | 0.661 | 133.189 | 0.287 |
| Comparative example 3 | 1161 | 246.406 | 0.513 | 175.686 | 0.220 |
| Blank group | 1047 | 251.472 | 0.482 | 186.411 | 0.209 |
From upper table 6, compared with blank group, the methyl glycol fatty acid ester of the embodiment of the present invention 1～4 is as emulsifying
Agent is applied in cake, prepare cake hardness and chewiness is less, elastic and recovery is bigger, hence it is evident that improve cake product
Matter, increases cake volume, and the tissue making cake is fine and smooth, bulk easypro soft.In embodiment 1～4, Application Example 3 propylene glycol fat
The hardness of the cake that fat acid esters prepares and chewiness are minimum, and elastic, recovery and baked volume are maximum, and therefore, embodiment 3 is this
The most preferred embodiment of invention.
Comparative example 1 and comparative example 2 change kind and the ratio of described fatty acid component, and its action effect is not as good as embodiment
1～4；Comparative example 3 is prior art, and its foam performance is poor, can not well improve characteristics of cake, with blank group phase
Ratio does not has obvious difference.
Below it is only the preferred embodiment of the present invention, it is noted that it is right that above-mentioned preferred implementation is not construed as
The restriction of the present invention, protection scope of the present invention should be as the criterion with claim limited range.For the art
For those of ordinary skill, without departing from the spirit and scope of the present invention, it is also possible to make some improvements and modifications, these change
Enter and retouch and also should be regarded as protection scope of the present invention.
Claims (6)
1. the preparation method of a methyl glycol fatty acid ester, it is characterised in that comprise the following steps:
S1,1,2-PD and fatty acid are added filter after heat fusing respectively；
S2, by 1,2-PD suction reactor, add base catalyst, stirring mixing 30～40min, then fatty acid taken out
Entering reactor, controlling reaction temperature is 180～200 DEG C, and vacuum is 0.06～0.08MPa, carries out esterification 1～2h；
S3, esterification terminate, and are cooled to 100 DEG C of dischargings, prepare methyl glycol fatty acid ester；
Described fatty acid is Palmic acid, oleic acid and linoleic mixture, and described Palmic acid, oleic acid and linoleic weight ratio are
(3～5): (2～4): 1.
2. the preparation method of methyl glycol fatty acid ester as claimed in claim 1, it is characterised in that described 1,2-PD and fat
The weight ratio of acid is 1:(2～3).
3. the preparation method of methyl glycol fatty acid ester described in claim 1, it is characterised in that described base catalyst is carbonic acid
One or more in sodium, sodium bicarbonate, sodium hydroxide and potassium carbonate.
4. the preparation method of methyl glycol fatty acid ester as claimed in claim 1, it is characterised in that the addition of described base catalyst
Amount is the 3～6% of 1,2-PD weight.
5. the methyl glycol fatty acid ester that the preparation method as described in Claims 1 to 4 is arbitrary prepares.
6. methyl glycol fatty acid ester application in cake as claimed in claim 5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610415639.5A CN106083577B (en) | 2016-06-14 | 2016-06-14 | A kind of preparation method and application of methyl glycol fatty acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610415639.5A CN106083577B (en) | 2016-06-14 | 2016-06-14 | A kind of preparation method and application of methyl glycol fatty acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106083577A true CN106083577A (en) | 2016-11-09 |
| CN106083577B CN106083577B (en) | 2018-09-28 |
Family
ID=57845283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610415639.5A Active CN106083577B (en) | 2016-06-14 | 2016-06-14 | A kind of preparation method and application of methyl glycol fatty acid ester |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106083577B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108822289A (en) * | 2018-07-12 | 2018-11-16 | 广州汇科精细化工有限公司 | Composite catalyst and its application and the method for preparing water-soluble aliphatic ester |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6274357B1 (en) * | 1996-06-18 | 2001-08-14 | Unilever Patent Holdings B.V. | Enzymatic esterification process |
| CN101225044A (en) * | 2008-02-01 | 2008-07-23 | 河南兴泰科技实业有限公司 | Methyl glycol fatty acid ester and preparation method thereof |
| US20100274039A1 (en) * | 2007-12-27 | 2010-10-28 | Dai-Seung Choi | Catalyst composition including zirconium compounds for esterfication reaction and method for preparing ester compounds |
| CN102977945A (en) * | 2012-11-12 | 2013-03-20 | 黄河三角洲京博化工研究院有限公司 | Diesel oil lubricity improving agent |
-
2016
- 2016-06-14 CN CN201610415639.5A patent/CN106083577B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6274357B1 (en) * | 1996-06-18 | 2001-08-14 | Unilever Patent Holdings B.V. | Enzymatic esterification process |
| US20100274039A1 (en) * | 2007-12-27 | 2010-10-28 | Dai-Seung Choi | Catalyst composition including zirconium compounds for esterfication reaction and method for preparing ester compounds |
| CN101225044A (en) * | 2008-02-01 | 2008-07-23 | 河南兴泰科技实业有限公司 | Methyl glycol fatty acid ester and preparation method thereof |
| CN102977945A (en) * | 2012-11-12 | 2013-03-20 | 黄河三角洲京博化工研究院有限公司 | Diesel oil lubricity improving agent |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108822289A (en) * | 2018-07-12 | 2018-11-16 | 广州汇科精细化工有限公司 | Composite catalyst and its application and the method for preparing water-soluble aliphatic ester |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106083577B (en) | 2018-09-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2740415C (en) | Food compositions of microalgal biomass | |
| JP7114650B2 (en) | Plastic fat composition | |
| CN103829032B (en) | Preparation method for composite phagostimulant for enhancing food intake of weaned pigs | |
| CN101946815A (en) | Hulless oat enriched bread and preparation method thereof | |
| KR20160032467A (en) | Method for processing natural yeast paste and natural yeast bread using thereof | |
| CN104397121A (en) | Cookies for students and preparation method of cookies for students | |
| CN107518371A (en) | A kind of preparation method of roasting fragrance milk base material | |
| CN106083577A (en) | A kind of preparation method and application of methyl glycol fatty acid ester | |
| CN104585274A (en) | Novel fruit bread and preparation method thereof | |
| JP6608629B2 (en) | Bread production method | |
| CN103598278A (en) | Milk flavor powder for cakes and preparing method thereof | |
| KR20150068606A (en) | A premix composition for corn dog using powdered egg white, a corn dog prepared by using the same and a method for preparing the corn dog | |
| JPS63301765A (en) | Highly foamable fat and oil composition | |
| CN105432755A (en) | Chiffon cake premixing powder and making method of chiffon cake | |
| CN103125570A (en) | Process for producing cake low in content of saturated fatty acid | |
| CN104430734A (en) | Coarse food grain biscuit and making method thereof | |
| CN105025727A (en) | Emulsified oil composition | |
| JP6178221B2 (en) | Bread production method | |
| US3622345A (en) | Propylene glycol monoester emulsifier-containing shortenings and cake mixes containing the same | |
| JP2012125168A (en) | Method for producing baked confectionery dough using rice flour | |
| JPH049506B2 (en) | ||
| KR101658321B1 (en) | White bread manufacturing method using Lentil bean | |
| JP2556237B2 (en) | Sponge cake manufacturing method | |
| RU2598040C2 (en) | Method of sponge semi-product for production | |
| CN105152929B (en) | A kind of propylene glycol monostearate and its industrial process and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CP03 | Change of name, title or address | ||
| CP03 | Change of name, title or address |
Address after: No. 6, Huafeng Road, Yonghe District, Guangzhou Economic and Technological Development Zone, Guangdong 510530 Patentee after: Guangdong Jiadele Technology Co.,Ltd. Address before: No. 6 Huafeng Road, Yonghe Economic Zone, Guangzhou Economic and Technological Development Zone, Guangdong Province, 510635 Patentee before: GUANGZHOU CARDLO BIOCHEMICAL TECHNOLOGY Co.,Ltd. |