CN101092353B - Preparation method for transforming animal and vegetable oil and fat to mono ester fatty acid - Google Patents
Preparation method for transforming animal and vegetable oil and fat to mono ester fatty acid Download PDFInfo
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Abstract
This invention relates to a method for converting animal and vegetable oils into fatty acid monoesters without discharge. The method comprises: pumping animal and vegetable oils, monohydric alcohols and catalyst into a pressure reaction tank, sealing, stirring, heating to the transesterification temperature, performing transesterification reaction, spraying the reaction mixture into an evaporator, evaporating excess monohydric alcohols and catalyst, introducing into a condenser, condensing into liquids, recovering, and demixing the mother liquid after monohydric alcohols and catalyst are evaporated to obtain fatty acid monoesters (low specific gravity) and glycerol byproduct (high specific gravity). The method has such advantages as abundant raw materials, easy recovery of catalyst, mild production conditions, short reaction time, and simple process, and is suitable for industrialization.
Description
Technical field
What the present invention relates to is a kind of method for producing biodiesel of bioenergy technical field, but specifically is a kind of preparation method of transforming animal and vegetable oil and fat to mono ester fatty acid of no waste discharging recycle to extinction utilization.
Background technology
Biofuel is meant fatty acid methyl ester or the ethyl ester that utilizes reproducible animal-plant oil (as rapeseed oil, soybean oil, peanut oil, plam oil, Oleum Cocois, recovery culinary art oil, animal grease etc.) to carry out the transesterify generation for raw material and methyl alcohol or ethanol.This fatty acid methyl ester or ethyl ester have similar performance to the diesel oil of fossil sources, can use as diesel oil.Utilizing this renewable resources to produce diesel oil is one of solution of fossil energy shortage crisis.Simultaneously, because annual discarded edible oil flows into rivers sea pollution on the environment by water drain, restaurant or family burnt Lay exhausted vegetables oil and animal oil production biofuel and can alleviate the pressure of environmental pollution, can have important society and economic implications for Economic development provides motor vehicle fuel again.
Committed step is a transesterification reaction in the production of biodiesel at present.Base catalysis method reaction is subjected in the raw material influence of free lipid acid and moisture content very serious; Conventional sulfuric acid, hydrochloric acid and sulfonic acid catalyzes temperature of reaction and pressure are higher, and speed of reaction is slow.More than the common drawback of two kinds of methods be in the catalysis and the back discharging produces waste liquor contamination environment, the postorder process for refining complexity of product.Biological catalysis reaction conditions gentleness, but enzyme cost height, work-ing life is short again, and catalytic process is long, and scale production is difficult.The supercritical alcohols ester-interchange method does not need catalyzer, and the time is very short, the transformation efficiency height, and shortcoming is that reaction needed is carried out under High Temperature High Pressure, and equipment performance requires high, and investment is big, and energy consumption is big.
Find the paper of " research of solid acid catalysis esterification acidifying oil biodiesel synthesis " that Zhang Hairong etc. deliver (" oil and gas chemical industry ", 2007, the 36 volumes the 2nd phase 114-117 page or leaf) by prior art documents.The SO of modification is used in this paper utilization
4 2--TiO
2Ester conversion reaction during/clay solid acid catalyst catalysis biological diesel oil is synthetic.70 ℃ of temperature of reaction, pure oil quality be than 0.43: 1, and catalyst levels is stock oil 5% of the consumption that feeds intake, and the reaction times is 6～8h, the transformation efficiency during swill oil reaction 6h, 90-97%, the transformation efficiency 95-98% during corps acid-respons 8h.The SO of modification
4 2-TiO
2/ clay solid acid catalyst can be recycled 20 times.The homogeneous catalyst sodium methylate is compared with the vitriol oil and highly acidic resin, adopting the advantage of solid acid as catalyst is the catalytic activity height, no saponification, and catalyst levels lacks than highly acidic resin, good stability, the transformation efficiency when using 20 times during corps acid-respons 8h still can reach more than 90%.But the catalysis of solid catalyst reaction times is oversize, and catalyzer is easily poisoned, and the waste solid catalyzer remains a kind of source of pollution.Equipment capacity is low simultaneously.Therefore, be necessary that Development and Production efficient height, equipment capacity are big, the production technique of no waste discharging.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art and defective, a kind of preparation method of transforming animal and vegetable oil and fat to mono ester fatty acid is provided.Catalysis animal-plant oil of the present invention transforms the preparation fatty acid monoester in production of biodiesel, is no waste discharging, efficient, eco-friendly green production method, can quick, easy, production biofuel low-costly and in high volume.
The present invention is achieved by the following technical solutions, and the present invention specifically comprises the steps:
(1) with the catalyzer of vegetable and animals oils fat raw material, monohydroxy-alcohol raw material and the desired number of desired number with pump delivery in the carrying capacity retort;
(2) with carrying capacity retort sealing, mix, be heated to transesterification reaction temperature required after, constant temperature to transesterification reaction is finished;
(3) the transesterification reaction mixture is directly sprayed into from the carrying capacity retort in the vaporizer, excessive raw alcohol and catalyzer evaporate into steam, introduce condenser condenses and become liquid, reclaim circulation;
(4) the pure and mild catalyzer remaining mother liquor layering in back of volatilizing fully, the layer of light specific gravity be a fatty acid monoester, i.e. the biofuel of Huo Deing, heavy layer is glycerin by-products.
In the step (1), described vegetable and animals oils fat raw material is Vegetable oil lipoprotein, animal grease or its mixture;
Described Vegetable oil lipoprotein comprises from plant seed, pulp and other part are (as the root of plant, stem, leaf) fatty acid triglycercide of extraction gained is as soybean oil, rapeseed oil, plam oil, Oleum Gossypii semen, Cortex jatrophae fruit oil, microalgae grease, peanut oil, sunflower seed oil, Viscotrol C, sesame oil, linseed oil, safflower oil, tea-seed oil, sweet oil, palm-kernel oil, Semen Maydis oil, the oil palm seed oil, shinyleaf yellowhorn oil, Chinese tallow tree seed oil, Chinese tallow tree fruit oil, tung nut oil, sumac(h)berries oil, corylaceae fruit oil, spindleberry oil, root of Beijing euphorbia fruit oil, perillaseed fruit oil, wilson dogwood fruit oil, Chinese pistache fruit oil, Cortex jatrophae fruit oil, tung nut oil, the any mixing of oil tea fruit wet goods any or its.
Described fatty acid triglycercide, its raw material can be culinary art exhausted waste oil or trench refiltered oil.
Described animal-plant oil, wherein animal grease comprises the fatty acid triglycercide that extracts gained from animal body, as any mixing of chicken fat fat, duck grease, pig fat, shea butter, sheep grease, turkey grease etc. any or its.
In the step (1), described catalyzer is a trifluoroacetic acid; Catalyst system therefor concentration is 0.1mol/L-3.0mol/L.
In the step (1), described alcohol comprises the monohydroxy-alcohol of 1-8 carbon, as methyl alcohol, ethanol, propyl alcohol, butanols, amylalcohol, hexanol, enanthol and octanol, with and isomer.
Described alcohol, its add-on is alcohol: grease mol ratio=1: 1 to 60: 1.
In the step (2), described transesterification reaction temperature is 80 ℃ to 200 ℃;
The described reaction times is 0.1 to 5 hour.
The present invention compared with prior art, raw material sources extensively, the catalyst recovery circulation easily, working condition is gentle, the reaction times is short, technology is simple, is suitable for large-scale industrial production.The present invention simultaneously is converted into the total conversion rate height of monoesters class, the part total conversion rate is up to 98-100%, excessive pure and mild catalyzer can the recycle to extinction utilization by simple and easy evaporation, and by-product glycerin is by simply being separated or product can be made with extra care by simple and easy distillation.
Embodiment
Below embodiments of the invention are elaborated: present embodiment is being to implement under the prerequisite with the technical solution of the present invention, provided detailed embodiment and concrete operating process, but protection scope of the present invention is not limited to following embodiment.Those skilled in the art make various changes or modifications the present invention; can be replaced with peanut oil as initial triglyceride feedstock; sunflower seed oil; Viscotrol C; sesame oil; linseed oil; safflower oil; tea-seed oil; sweet oil; palm-kernel oil; Semen Maydis oil; the oil palm seed oil; shinyleaf yellowhorn oil; stillingia oil; tung oil tree oil; the Anacardiaceae seed oil; the corylaceae seed oil; the Celastraceae seed oil; the Euphorbiaceae seed oil; perillaseed seed oil and duck grease; shea butter; sheep grease; turkey grease etc.; alcohol can change into; butanols; amylalcohol; hexanol; enanthol and octanol; with and the alcohol of isomeric forms, these equivalent form of values fall within protection scope of the present invention equally.
Embodiment 1
Get soybean oil 1ml, methyl alcohol 0.20ml, trifluoroacetic acid 0.28ml, making molar ratio of methanol to oil is 5: 1, trifluoroacetic acid concentration 2.5M adds in the stainless steel tube, airtightly is heated to 180 ℃, is incubated 0.5 hour.Open stainless steel tube then, mixture is injected in the round bottom glass flask, but unreacted methanol and the evaporation of trifluoroacetic acid catalyzer, condensation collection recycle to extinction utilize again; Non-volatile part cooling back is divided two-layer up and down, and the upper strata is a biofuel, and lower floor is a glycerine.With gas chromatography-mass spectrometry analysis upper strata biofuel, wherein fatty acid methyl ester is 94%.
Present embodiment is converted into the total conversion rate height of monoesters class, and total conversion rate is up to 98-100%, and by-product glycerin is by simply being separated or product can be made with extra care by simple and easy distillation.The present embodiment catalyzer can use in recycle to extinction, and eco-friendly suitability for industrialized production is discharged, is suitable for to no waste.Compared with prior art, the present embodiment transesterification time can be reduced to 0.1 hour from 6～8h.
Embodiment 2
Get rapeseed oil 1ml, ethanol 0.6ml, trifluoroacetic acid 0.33ml, making molar ratio of methanol to oil is 11: 1, trifluoroacetic acid concentration 2.2M adds and is heated to 120 ℃ in the airtight stainless steel tube, is incubated 5 hours.Open stainless steel tube then, mixture is injected in the round bottom glass flask, unreacted methanol and trifluoroacetic acid evaporation are collected after the condensation again and are utilized; Non-volatile part cooling back is divided two-layer up and down, and the upper strata is a biofuel, and lower floor is a glycerine.It is 0.900 that density is surveyed on the upper strata, uses gas chromatography-mass spectrometry analysis, and wherein fatty acid methyl ester is 97%.
Present embodiment is converted into the total conversion rate height of monoesters class, and total conversion rate is up to 98-100%, and by-product glycerin is by simply being separated or product can be made with extra care by simple and easy distillation.The present embodiment catalyzer can use in recycle to extinction, and eco-friendly suitability for industrialized production is discharged, is suitable for to no waste.Compared with prior art, the present embodiment transesterification time can be reduced to 0.1 hour from 6～8h.
Embodiment 3
Get plam oil 1ml, propyl alcohol 1.3ml, trifluoroacetic acid 0.23ml, making molar ratio of methanol to oil is 18: 1, trifluoroacetic acid concentration 2.2M adds and is heated to 150 ℃ in the airtight stainless steel tube, is incubated 0.1 hour.Open stainless steel tube then, mixture is injected in the round bottom glass flask, unreacted methanol and trifluoroacetic acid evaporation are collected after the condensation again and are utilized; Non-volatile part cooling back is divided two-layer up and down, and the upper strata is a biofuel, and lower floor is a glycerine.It is 0.878 that density is surveyed on the upper strata.
Present embodiment is converted into the total conversion rate height of monoesters class, and total conversion rate is up to 98-100%, and by-product glycerin is by simply being separated or product can be made with extra care by simple and easy distillation.The present embodiment catalyzer can use in recycle to extinction, and eco-friendly suitability for industrialized production is discharged, is suitable for to no waste.Compared with prior art, the present embodiment transesterification time can be reduced to 0.1 hour from 6～8h.
Embodiment 4
Get Oleum Gossypii semen 1ml, butanols 0.9ml, trifluoroacetic acid 0.10ml, making molar ratio of methanol to oil is 10: 1, trifluoroacetic acid concentration 0.7M adds and is heated to 130 ℃ in the airtight stainless steel tube, is incubated 0.6 hour.Open stainless steel tube then, mixture is injected in the round bottom glass flask, unreacted methanol and trifluoroacetic acid evaporation are collected after the condensation again and are utilized; Non-volatile part cooling back is divided two-layer up and down, and the upper strata is a biofuel, and lower floor is a glycerine.It is 0.860 that density is surveyed on the upper strata, uses gas chromatography-mass spectrometry analysis, and wherein fatty acid methyl ester is 99.96%.
Present embodiment is converted into the total conversion rate height of monoesters class, and total conversion rate is up to 98-100%, and by-product glycerin is by simply being separated or product can be made with extra care by simple and easy distillation.The present embodiment catalyzer can use in recycle to extinction, and eco-friendly suitability for industrialized production is discharged, is suitable for to no waste.Compared with prior art, the present embodiment transesterification time can be reduced to 0.1 hour from 6～8h.
Embodiment 5
Get curcas oil 1ml, amylalcohol 0.13ml, trifluoroacetic acid 0.1ml, making molar ratio of methanol to oil is 1: 1, trifluoroacetic acid concentration 0.11M adds in the stainless steel tube, airtightly is heated to 100 ℃, is incubated 2 hours.Open stainless steel tube then, mixture is injected in the round bottom glass flask, unreacted methanol and trifluoroacetic acid evaporation are collected after the condensation again and are utilized; Non-volatile part cooling back is divided two-layer up and down, and the upper strata is a biofuel, and lower floor is a glycerine.It is 0.862 that density is surveyed on the upper strata, uses gas chromatography-mass spectrometry analysis, and wherein fatty acid methyl ester is 97%.
Present embodiment is converted into the total conversion rate height of monoesters class, and total conversion rate is up to 98-100%, and by-product glycerin is by simply being separated or product can be made with extra care by simple and easy distillation.The present embodiment catalyzer can use in recycle to extinction, and eco-friendly suitability for industrialized production is discharged, is suitable for to no waste.Compared with prior art, the present embodiment transesterification time can be reduced to 0.1 hour from 6～8h.
Embodiment 6
Get microalgae grease 0.5ml, hexanol 0.37ml, trifluoroacetic acid 0.05ml, making molar ratio of methanol to oil is 6: 1, trifluoroacetic acid concentration 0.7M adds and is heated to 200 ℃ in the airtight stainless steel tube, is incubated 0.25 hour.Open stainless steel tube then, mixture is injected in the round bottom glass flask, unreacted methanol and trifluoroacetic acid evaporation are collected after the condensation again and are utilized; Non-volatile part cooling back is divided two-layer up and down, and the upper strata is a biofuel, and lower floor is a glycerine.It is 0.876 that density is surveyed on the upper strata, uses gas chromatography-mass spectrometry analysis, and wherein fatty acid methyl ester is 99%.
Present embodiment is converted into the total conversion rate height of monoesters class, and total conversion rate is up to 98-100%, and by-product glycerin is by simply being separated or product can be made with extra care by simple and easy distillation.The present embodiment catalyzer can use in recycle to extinction, and eco-friendly suitability for industrialized production is discharged, is suitable for to no waste.Compared with prior art, the present embodiment transesterification time can be reduced to 0.1 hour from 6～8h.
Embodiment 7
Get stillingia oil 0.5ml, enanthol 0.43ml, trifluoroacetic acid 0.01ml, making molar ratio of methanol to oil is 6: 1, trifluoroacetic acid concentration 0.1M adds in the stainless steel tube, airtightly is heated to 190 ℃, is incubated 1 hour.Open stainless steel tube then, mixture is injected in the round bottom glass flask, unreacted methanol and trifluoroacetic acid evaporation are collected after the condensation again and are utilized; Non-volatile part cooling back is divided two-layer up and down, and the upper strata is a biofuel, and lower floor is a glycerine.With gas chromatography-mass spectrometry analysis upper strata product, wherein fatty acid methyl ester is 83%.
Present embodiment is converted into the total conversion rate height of monoesters class, and total conversion rate is up to 98-100%, and by-product glycerin is by simply being separated or product can be made with extra care by simple and easy distillation.The present embodiment catalyzer can use in recycle to extinction, and eco-friendly suitability for industrialized production is discharged, is suitable for to no waste.Compared with prior art, the present embodiment transesterification time can be reduced to 0.1 hour from 6～8h.
Embodiment 8
Get tung oil tree oil 1ml, octanol 0.2ml, trifluoroacetic acid 0.35ml, making molar ratio of methanol to oil is 1: 1, trifluoroacetic acid concentration 3.0M adds in the stainless steel tube, airtightly is heated to 80 ℃, is incubated 0.4 hour.Open stainless steel tube then, mixture is injected in the round bottom glass flask, unreacted methanol and trifluoroacetic acid evaporation are collected after the condensation again and are utilized; Non-volatile part cooling back is divided two-layer up and down, and the upper strata is a biofuel, and lower floor is a glycerine.With gas chromatography-mass spectrometry analysis upper strata product, wherein fatty acid methyl ester is 98%.
Present embodiment is converted into the total conversion rate height of monoesters class, and total conversion rate is up to 98-100%, and by-product glycerin is by simply being separated or product can be made with extra care by simple and easy distillation.The present embodiment catalyzer can use in recycle to extinction, and eco-friendly suitability for industrialized production is discharged, is suitable for to no waste.Compared with prior art, the present embodiment transesterification time can be reduced to 0.1 hour from 6～8h.
Embodiment 9
Get chicken fat fat 1ml, methyl alcohol 0.4ml, trifluoroacetic acid 0.2ml, making molar ratio of methanol to oil is 10: 1, trifluoroacetic acid concentration 1.6M adds in the stainless steel tube, airtightly is heated to 160 ℃, is incubated 0.8 hour.Open stainless steel tube then, mixture is injected in the round bottom glass flask, unreacted methanol and trifluoroacetic acid evaporation are collected after the condensation again and are utilized; Non-volatile part cooling back is divided two-layer up and down, and the upper strata is a biofuel, and lower floor is a glycerine.With gas chromatography-mass spectrometry analysis upper strata product, wherein fatty acid methyl ester is 100%.
Present embodiment is converted into the total conversion rate height of monoesters class, and total conversion rate is up to 98-100%, and by-product glycerin is by simply being separated or product can be made with extra care by simple and easy distillation.The present embodiment catalyzer can use in recycle to extinction, and eco-friendly suitability for industrialized production is discharged, is suitable for to no waste.Compared with prior art, the present embodiment transesterification time can be reduced to 0.1 hour from 6～8h.
Embodiment 10
Get waste vegetable oil 0.5ml, methyl alcohol 0.98ml, trifluoroacetic acid 0.44ml, making molar ratio of methanol to oil is 41: 1, trifluoroacetic acid concentration 2.5M adds in the stainless steel tube, airtightly is heated to 180 ℃, is incubated 2 hours.Open stainless steel tube then, mixture is injected in the round bottom glass flask, unreacted methanol and trifluoroacetic acid evaporation are collected after the condensation again and are utilized; Non-volatile part cooling back is divided two-layer up and down, and the upper strata is a biofuel, and lower floor is a glycerine.It is 0.884 that density is surveyed on the upper strata.
Present embodiment is converted into the total conversion rate height of monoesters class, and total conversion rate is up to 98-100%, and by-product glycerin is by simply being separated or product can be made with extra care by simple and easy distillation.The present embodiment catalyzer can use in recycle to extinction, and eco-friendly suitability for industrialized production is discharged, is suitable for to no waste.Compared with prior art, the present embodiment transesterification time can be reduced to 0.1 hour from 6～8h.
Embodiment 11
Get pig fat 0.5ml, methyl alcohol 1.16ml, trifluoroacetic acid 0.43ml, making molar ratio of methanol to oil is 60: 1, trifluoroacetic acid concentration 2.7M adds in the stainless steel tube, airtightly is heated to 165 ℃, is incubated 4 hours.Open stainless steel tube then, mixture is injected in the round bottom glass flask, unreacted methanol and trifluoroacetic acid evaporation are collected after the condensation again and are utilized; Non-volatile part cooling back is divided two-layer up and down, and the upper strata is a biofuel, and lower floor is a glycerine.It is 0.830 that density is surveyed on the upper strata.
Present embodiment is converted into the total conversion rate height of monoesters class, and total conversion rate is up to 98-100%, and by-product glycerin is by simply being separated or product can be made with extra care by simple and easy distillation.The present embodiment catalyzer can use in recycle to extinction, and eco-friendly suitability for industrialized production is discharged, is suitable for to no waste.Compared with prior art, the present embodiment transesterification time can be reduced to 0.1 hour from 6～8h.
Claims (11)
1. the preparation method of a transforming animal and vegetable oil and fat to mono ester fatty acid is characterized in that, specifically comprises the steps:
(1) with vegetable and animals oils fat raw material, monohydroxy-alcohol raw material and trifluoroacetic acid catalyzer with pump delivery in the carrying capacity retort;
(2) with carrying capacity retort sealing, mix, be heated to transesterification reaction temperature after, constant temperature to transesterification reaction is finished;
(3) the transesterification reaction mixture is directly sprayed into from the carrying capacity retort in the vaporizer, excessive raw alcohol and trifluoroacetic acid catalyzer evaporate into steam, introduce condenser condenses and become liquid, reclaim circulation;
(4) remaining mother liquor layering after pure and mild trifluoroacetic acid catalyzer volatilizees fully, the layer of light specific gravity is a fatty acid monoester, heavy layer is a glycerin by-products.
2. the preparation method of transforming animal and vegetable oil and fat to mono ester fatty acid as claimed in claim 1 is characterized in that, in the step (1), described vegetable and animals oils fat raw material is Vegetable oil lipoprotein, animal grease or its mixture.
3. the preparation method of transforming animal and vegetable oil and fat to mono ester fatty acid as claimed in claim 1 or 2 is characterized in that, described animal-plant oil is a fatty acid triglycercide.
4. the preparation method of transforming animal and vegetable oil and fat to mono ester fatty acid as claimed in claim 1 or 2, it is characterized in that described animal-plant oil is: soybean oil, rapeseed oil, plam oil, Oleum Gossypii semen, Cortex jatrophae fruit oil, microalgae grease, peanut oil, sunflower seed oil, Viscotrol C, sesame oil, linseed oil, safflower oil, tea-seed oil, sweet oil, palm-kernel oil, Semen Maydis oil, the oil palm seed oil, shinyleaf yellowhorn oil, Chinese tallow tree seed oil, Chinese tallow tree fruit oil, tung nut oil, sumac(h)berries oil, corylaceae fruit oil, spindleberry oil, root of Beijing euphorbia fruit oil, perillaseed fruit oil, wilson dogwood fruit oil, Chinese pistache fruit oil, Cortex jatrophae fruit oil, tung nut oil, the any mixing of oil tea fruit oil any or its.
5. the preparation method of transforming animal and vegetable oil and fat to mono ester fatty acid as claimed in claim 1 or 2 is characterized in that, described animal-plant oil is: chicken fat fat, duck grease, pig fat, shea butter, sheep grease, any mixing of turkey grease any or its.
6. the preparation method of transforming animal and vegetable oil and fat to mono ester fatty acid as claimed in claim 1 is characterized in that, described trifluoroacetic acid catalyst concentration is 0.1mol/L-3.0mol/L.
7. the preparation method of transforming animal and vegetable oil and fat to mono ester fatty acid as claimed in claim 1 is characterized in that, in the step (1), described alcohol is the monohydroxy-alcohol of 1-8 carbon.
8. as the preparation method of claim 1 or 7 described transforming animal and vegetable oil and fat to mono ester fatty acid, it is characterized in that in the step (1), described alcohol is: methyl alcohol, ethanol, propyl alcohol, butanols, amylalcohol, hexanol, enanthol and octanol and isomer thereof any.
9. as the preparation method of claim 1 or 7 described transforming animal and vegetable oil and fat to mono ester fatty acid, it is characterized in that, described alcohol, its add-on is alcohol: grease mol ratio=1: 1 to 60: 1.
10. the preparation method of transforming animal and vegetable oil and fat to mono ester fatty acid as claimed in claim 1 is characterized in that, in the step (2), described transesterification reaction temperature is 80 ℃ to 200 ℃.
11. the preparation method as claim 1 or 10 described transforming animal and vegetable oil and fat to mono ester fatty acid is characterized in that, described transesterification reaction, and its reaction times is 0.1 to 5 hour.
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| KR101916421B1 (en) * | 2010-05-28 | 2018-11-08 | 테라비아 홀딩스 인코포레이티드 | Tailored oils produced from recombinant heterotrophic microorganisms |
| EP3521408B1 (en) | 2010-11-03 | 2021-12-22 | Corbion Biotech, Inc. | Genetically-engineered chlorella or prototheca microbe and oil produced therefrom |
| MX351063B (en) | 2011-02-02 | 2017-09-29 | Terravia Holdings Inc | Tailored oils produced from recombinant oleaginous microorganisms. |
| CN102504891B (en) * | 2011-11-02 | 2014-11-05 | 南京工业大学 | Preparation method of glyceryl biological fuel additives |
| JP6499577B2 (en) | 2012-04-18 | 2019-04-10 | テラヴィア ホールディングス， インコーポレイテッド | Adjustment oil |
| CN102993132B (en) * | 2012-12-07 | 2014-12-31 | 浙江工业大学 | Device for producing epoxidized fatty acid methyl ester |
| CN104017656A (en) * | 2013-02-28 | 2014-09-03 | 河源市汇盛生物科技有限公司 | Fatty acid methyl ester and preparation method thereof |
| CN103436368B (en) * | 2013-09-04 | 2015-04-01 | 西安石油大学 | Method for synchronously preparing biodiesel and glycerol carbonate by using alkali-earth oxide as catalyst |
| CA2925527A1 (en) | 2013-10-04 | 2015-04-09 | Solazyme, Inc. | Tailored oils |
| EP3167053B1 (en) | 2014-07-10 | 2019-10-09 | Corbion Biotech, Inc. | Novel ketoacyl acp synthase genes and uses thereof |
| CN105505588A (en) * | 2015-08-19 | 2016-04-20 | 张敏 | Compound biodiesel and preparation method thereof |
| CN113826821B (en) * | 2021-09-24 | 2023-04-25 | 青岛农业大学 | High-stretchability low-fat non-fried instant rice noodles and preparation method thereof |
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| CN1743416A (en) * | 2004-08-30 | 2006-03-08 | 中油双星生物柴油有限公司 | Apparatus for producing biodiesel for vehicle and its preparing method |
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