CN102250693A - Process flow for preparing epoxidized soybean oil by using crude soybean oil - Google Patents
Process flow for preparing epoxidized soybean oil by using crude soybean oil Download PDFInfo
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- CN102250693A CN102250693A CN2011101674737A CN201110167473A CN102250693A CN 102250693 A CN102250693 A CN 102250693A CN 2011101674737 A CN2011101674737 A CN 2011101674737A CN 201110167473 A CN201110167473 A CN 201110167473A CN 102250693 A CN102250693 A CN 102250693A
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- soybean oil
- oil
- soybean
- crude oil
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- 235000012424 soybean oil Nutrition 0.000 title claims abstract description 35
- 239000003549 soybean oil Substances 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000005406 washing Methods 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 239000004593 Epoxy Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 20
- 235000010469 Glycine max Nutrition 0.000 claims description 18
- 244000068988 Glycine max Species 0.000 claims description 18
- 239000010779 crude oil Substances 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- 150000007524 organic acids Chemical class 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003921 oil Substances 0.000 claims description 8
- 235000019198 oils Nutrition 0.000 claims description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
- 239000012535 impurity Substances 0.000 claims description 7
- QKXCAKZMAORNSR-UHFFFAOYSA-N azane 1-chlorohexadecane Chemical group N.CCCCCCCCCCCCCCCCCl QKXCAKZMAORNSR-UHFFFAOYSA-N 0.000 claims description 6
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- 239000000344 soap Substances 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 5
- 125000005210 alkyl ammonium group Chemical group 0.000 claims description 5
- 235000019270 ammonium chloride Nutrition 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- -1 as phosphatide Substances 0.000 claims description 3
- 238000005119 centrifugation Methods 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 238000007701 flash-distillation Methods 0.000 claims description 3
- RNYJXPUAFDFIQJ-UHFFFAOYSA-N hydron;octadecan-1-amine;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH3+] RNYJXPUAFDFIQJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- 239000008234 soft water Substances 0.000 claims description 3
- 238000006735 epoxidation reaction Methods 0.000 abstract description 2
- 230000002860 competitive effect Effects 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 238000007670 refining Methods 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 5
- 239000004902 Softening Agent Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 2
- 239000002932 luster Substances 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 208000012826 adjustment disease Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- HPOKESDSMZRZLC-UHFFFAOYSA-N propan-2-one;hydrochloride Chemical compound Cl.CC(C)=O HPOKESDSMZRZLC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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- Epoxy Compounds (AREA)
Abstract
The invention relates to a process flow for preparing epoxidized soybean oil by using crude soybean oil, in particular to a process flow for preparing epoxidized soybean oil. The invention discloses the process flow for producing epoxidized soybean oil with an epoxide number of more than 6 percent by using crude soybean oil as a raw material and by a solvent-free method and comprises the steps of epoxidation, neutralizing washing, refining and the like. In the invention, the production process is optimized, the quality of the epoxidized soybean oil product is improved, the cost is lowered, the competitive power is increased, and the promotion and use are convenient.
Description
Technical field
The present invention relates to a kind of epoxy plasticiser preparation method, the technical process that specifically prepares epoxy soybean oil.
Background technology
Epoxy soybean oil (ESO) belongs to epoxy plasticiser, it is a kind of widely used polyvinyl chloride (PVC) softening agent stablizer of holding concurrently, has good light and heat stabilization, compare with ester plasticizer and to have anti-extraction, anti-migration, anti-volatilization, intermiscibility reaches advantages such as degradable well, it is unique epoxy plasticiser that can be used for packaging material for food, it is as the favorable substitutes of phthalic ester plasticizer, meet the RoHS of European Union environmental protection instruction and U.S. FDA foodstuff additive rule fully, caused showing great attention to of increasing plastic working industry and plasticizer production enterprise, current, the annual production of China's phthalic ester plasticizer and consumption all account for more than 80% of softening agent total amount, and epoxy soybean oil (ESO) is less than 10%; And in the U.S., its consumption is only second to phthalic ester and fatty group dibasic acid softening agent, occupies the 3rd.Along with the aggravation of the energy and ecocrisis, the development and use of renewable resources become the research focus, and therefore, exploitation epoxy soybean oil (ESO) has vast potential for future development.
The preparation method of epoxy soybean oil (ESO) has two kinds of solvent method and solventless methods, and solvent method exists difficult solvent recovery, cost height, pollutes shortcomings such as big, is replaced by the novel process solventless method at present.But solventless method still ubiquity is following not enough:
1, the less stable of epoxidation reaction, the product oxirane value is not high, and color and luster is darker;
2, the Chang Yidan still is produced, and throughput is little, and potential safety hazard is many;
3, the state of the art of separation and purification technology falls behind, and energy consumption is higher, and product yield is low, the cost height.
Summary of the invention
In order to overcome the deficiency of present technology, the invention provides the technical process for preparing epoxy soybean oil with crude oil of soybean, optimization production technology improves epoxy soybean oil (ESO) quality product, reduces cost, and enhances the competitiveness, and is convenient to promote and use.
Technical solution of the present invention is, and to be raw material with the crude oil of soybean produce oxirane value greater than 6% epoxy soybean oil with solventless method, and (the material add-on is that 100 weight parts are benchmark with crude oil of soybean) has the following steps:
A, crude oil of soybean and organic acid and hydrogen peroxide reaction
After in stirring rake, thermometer, condenser reactor are housed, adding crude oil of soybean 100 weight parts and organic acid 5 ~ 20 weight parts, stir with 70 ~ 100r/min rotating speed, the mixed solution that in batches adds hydrogen peroxide 40 ~ 50 weight parts and chain alkyl ammonium chloride catalyzer 0.3 ~ 0.6 weight part then,, between 55 ~ 65 ℃, reacted 5 ~ 10 hours with the cold water control reaction temperature;
B, A step products are with diluted alkaline neutralization and washing separation of fatty acids soap
With the product that above-mentioned A step obtains, add dilute NaOH solution and continue to stir until neutrality, enter the washing still then, add soft water and be no more than 2 minutes with the 65r/min stirring;
C, B step washing after product are made with extra care
At first leave standstill and to oily water separation water was drained in 4 ~ 8 hours, at this moment the Water in oil amount is heated to 70 ~ 100 ℃ then 10 ~ 30%, enters whizzer and carries out centrifugation and fall impurity in most of epoxy soybean oil, as phosphatide, water and fatty acid soaps; Epoxy soybean oil after the separation is controlled at more than 90 ℃, sends in the flash distillation dryer, is dried to water content less than 0.3% under vacuum tightness is not less than 0.9MPa; Dried epoxy soybean oil through plate and frame filter that diatomite forms filter cake with oil in remaining impurities filter out, pack at last.
The employed organic acid of described steps A is formic acid, acetate or propionic acid.
The employed chain alkyl ammonium chloride of steps A of the present invention catalyzer is cetyl chloride ammonium or octadecyl ammonium chloride.
Positively effect of the present invention is:
1, adopt hydrogen peroxide progressively to add and make reactant control within the specific limits, temperature is convenient to control, thereby reduces side reaction, helps improving the product oxirane value.
2, hydrogen peroxide, catalyzer and organic acid consumption carry out trickle adjustment, thereby obtain more high epoxy value.
3, adjustment reaction times, temperature of reaction make that oxirane value is the highest.
4, process optimization makes raw material consumption, energy consumption reduce greatly, and quality product improves greatly.
Description of drawings
Fig. 1 is a technological process block-diagram of the present invention.
Fig. 2 is the every performance and the energy consumption contrast table of the present invention and prior art and GB.
Embodiment
(1) raw material among the embodiment
The specification of quality of crude oil of soybean is: color and luster (Luo Wei canopy cuvette 133.4mm): Y=40, R=4.0; Have soy bean oil inherent smell, flavour; Moisture and volatile matter content (%): 0.20; Insoluble impurities (%): 0.20; Iodine number (gI
2/ g): 128 ~ 129; Acid number (mgKOH/g): 1.5 ~ 4.0; Peroxide value (mmol/kg): 7.5; Solvent residual amount (mg/kg): 100; More than the phosphorus content ppm:143.
(2) epoxy soybean oil performance and testing method
The epoxy soybean oil oxirane value refers to the content (unit: mg/100g or %) of oxygen in every 100g sample.Measure according to GB/T 1677-2008 GB, adopt hydrochloric acid-acetone method to measure.
During the acid number of epoxy soybean oil refers to and the needed potassium hydroxide of 1g softening agent the milligram number.Standard GB/T 1668-2008 according to the plasticiser acid pH-value determination pH measures.
Embodiment 1
According to shown in Figure 1, being raw material with the crude oil of soybean produces oxirane value at 〉=6.0% epoxy soybean oil with solventless method, and (the material add-on is that 100 weight parts are benchmark with crude oil of soybean) has the following steps:
A, crude oil of soybean and organic acid and hydrogen peroxide reaction
After in stirring rake, thermometer, condenser reactor are housed, adding crude oil of soybean 100 weight parts and formic acid 5 weight parts, stir with the 100r/min rotating speed, the mixed solution that in batches adds hydrogen peroxide 50 weight parts and cetyl chloride ammonium 0.6 weight part then,, between 65 ℃, reacted 6 hours with the cold water control reaction temperature;
B, A step products are with diluted alkaline neutralization and washing separation of fatty acids soap
With the product that above-mentioned A step obtains, add dilute NaOH solution and continue to stir until neutrality, enter the washing still then, add soft water and be no more than 2 minutes with the 65r/min stirring;
C, B step washing after product are made with extra care
At first leave standstill to oily water separation water is drained, make the Water in oil amount, be heated to 70 ℃ then, enter whizzer and carry out centrifugation and fall impurity in most of epoxy soybean oil, as phosphatide, water and fatty acid soaps 30%; Epoxy soybean oil after the separation is controlled at more than 90 ℃, sends in the thin-film evaporator of flash distillation dryer, is dried to water content and is less than 0.3% under vacuum tightness is not less than 0.9MPa; Dried epoxy soybean oil through plate and frame filter that diatomite forms filter cake with oil in remaining impurities filter out, pack at last.
Identical with embodiment 1, just the formic acid add-on is 20 weight parts in the steps A, stirs with the 70r/min rotating speed then, adds the mixed solution of hydrogen peroxide 40 weight parts and cetyl chloride ammonium 0.3 weight part then in batches,, between 55 ℃, reacted 10 hours with the cold water control reaction temperature; The Water in oil amount is heated to 100 ℃ then 10% in the C step.
Embodiment 3
Identical with embodiment 1, just the formic acid add-on is 14 weight parts in the steps A, stirs with the 65r/min rotating speed then, adds the mixed solution of hydrogen peroxide 45 weight parts and cetyl chloride ammonium 0.45 weight part then in batches,, between 60 ℃, reacted 9 hours with the cold water control reaction temperature; The Water in oil amount is heated to 90 ℃ then 20% in the C step.
Embodiment 4
Identical with embodiment 1, just the employed chain alkyl ammonium chloride of steps A catalyzer is cetyl chloride ammonium or octadecyl ammonium chloride.
Identical with embodiment 1, just the employed organic acid of steps A is an acetate.
Embodiment 6
Identical with embodiment 1, just the employed organic acid of steps A is a propionic acid.
The various embodiments described above (novel process) all compare with prior art (old technology) and GB, obtain the contrast of every performance index shown in Figure 2 and cost consumption.
Claims (3)
1. the technical process for preparing epoxy soybean oil with crude oil of soybean is characterized in that with the crude oil of soybean to be raw material produce oxirane value greater than 6% epoxy soybean oil with solventless method, and (the material add-on is that 100 weight parts are benchmark with crude oil of soybean) has the following steps:
A, crude oil of soybean and organic acid and hydrogen peroxide reaction
After in stirring rake, thermometer, condenser reactor are housed, adding crude oil of soybean 100 weight parts and organic acid 5 ~ 20 weight parts, stir with 70 ~ 100r/min rotating speed, the mixed solution that in batches adds hydrogen peroxide 40 ~ 50 weight parts and chain alkyl ammonium chloride catalyzer 0.3 ~ 0.6 weight part then,, between 55 ~ 65 ℃, reacted 5 ~ 10 hours with the cold water control reaction temperature;
B, A step products are with diluted alkaline neutralization and washing separation of fatty acids soap
With the product that above-mentioned A step obtains, add dilute NaOH solution and continue to stir until neutrality, enter the washing still then, add soft water and be no more than 2 minutes with the 65r/min stirring;
C, B step washing after product are made with extra care
At first leave standstill and to oily water separation, water was drained in 4 ~ 8 hours, make the Water in oil amount, be heated to 70 ~ 100 ℃ then, enter whizzer and carry out centrifugation and fall impurity in most of epoxy soybean oil, as phosphatide, water and fatty acid soaps 10 ~ 30%; Epoxy soybean oil after the separation is controlled at more than 90 ℃, sends in the flash distillation dryer, is dried to water content less than 0.3% under vacuum tightness is not less than 0.9MPa; Dried epoxy soybean oil through plate and frame filter that diatomite forms filter cake with oil in remaining impurities filter out, pack at last.
2. the technical process for preparing epoxy soybean oil with crude oil of soybean according to claim 1 is characterized in that the employed organic acid of steps A is formic acid, acetate or propionic acid.
3. the technical process for preparing epoxy soybean oil with crude oil of soybean according to claim 1 is characterized in that the employed chain alkyl ammonium chloride of steps A catalyzer is cetyl chloride ammonium or octadecyl ammonium chloride.
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| CN2011101674737A CN102250693B (en) | 2011-06-21 | 2011-06-21 | Process flow for preparing epoxidized soybean oil by using crude soybean oil |
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| CN2011101674737A CN102250693B (en) | 2011-06-21 | 2011-06-21 | Process flow for preparing epoxidized soybean oil by using crude soybean oil |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102703225A (en) * | 2012-06-11 | 2012-10-03 | 刘忠 | Epoxidized soybean oil plasticizer and production method thereof |
| CN102719318A (en) * | 2012-05-21 | 2012-10-10 | 华东理工大学 | Method for preparing epoxidized soybean oil with high epoxy value by catalysis of cationic resin |
| CN102978010A (en) * | 2012-12-03 | 2013-03-20 | 浙江嘉澳环保科技股份有限公司 | Process method for producing epoxidized soybean oil by using crude soybean oil as raw material |
| CN103111332A (en) * | 2013-03-05 | 2013-05-22 | 安徽天意环保科技有限公司 | Catalyst for preparation of epoxy plasticizers |
| CN104086513A (en) * | 2014-07-10 | 2014-10-08 | 江南大学 | Method for preparing epoxy soybean oil by utilizing high-concentration oxydol reaction heat |
| CN105289017A (en) * | 2015-11-12 | 2016-02-03 | 佛山市高明晟俊塑料助剂有限公司 | Epoxy soybean oil drying device and drying method thereof |
| CN107964026A (en) * | 2017-11-28 | 2018-04-27 | 江南大学 | A kind of method that environment-friendly plasticizer is prepared by epoxidation phosphatide |
| CN117624081A (en) * | 2023-11-30 | 2024-03-01 | 广东锦坤实业有限公司 | Production method of epoxidized soybean oil and epoxy workshop |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102719318A (en) * | 2012-05-21 | 2012-10-10 | 华东理工大学 | Method for preparing epoxidized soybean oil with high epoxy value by catalysis of cationic resin |
| CN102703225A (en) * | 2012-06-11 | 2012-10-03 | 刘忠 | Epoxidized soybean oil plasticizer and production method thereof |
| CN102978010A (en) * | 2012-12-03 | 2013-03-20 | 浙江嘉澳环保科技股份有限公司 | Process method for producing epoxidized soybean oil by using crude soybean oil as raw material |
| CN103111332A (en) * | 2013-03-05 | 2013-05-22 | 安徽天意环保科技有限公司 | Catalyst for preparation of epoxy plasticizers |
| CN104086513A (en) * | 2014-07-10 | 2014-10-08 | 江南大学 | Method for preparing epoxy soybean oil by utilizing high-concentration oxydol reaction heat |
| CN105289017A (en) * | 2015-11-12 | 2016-02-03 | 佛山市高明晟俊塑料助剂有限公司 | Epoxy soybean oil drying device and drying method thereof |
| CN107964026A (en) * | 2017-11-28 | 2018-04-27 | 江南大学 | A kind of method that environment-friendly plasticizer is prepared by epoxidation phosphatide |
| CN107964026B (en) * | 2017-11-28 | 2020-03-31 | 江南大学 | Method for preparing environment-friendly plasticizer through epoxidized phospholipid |
| CN117624081A (en) * | 2023-11-30 | 2024-03-01 | 广东锦坤实业有限公司 | Production method of epoxidized soybean oil and epoxy workshop |
| CN117624081B (en) * | 2023-11-30 | 2024-09-06 | 广东锦坤实业有限公司 | Production method of epoxidized soybean oil and epoxy workshop |
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| CN102250693B (en) | 2013-12-11 |
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