WO2011002090A1 - 脂肪酸低級アルキルエステル、グリセリン及びステリルグリコシドの製造法 - Google Patents

脂肪酸低級アルキルエステル、グリセリン及びステリルグリコシドの製造法 Download PDF

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WO2011002090A1
WO2011002090A1 PCT/JP2010/061359 JP2010061359W WO2011002090A1 WO 2011002090 A1 WO2011002090 A1 WO 2011002090A1 JP 2010061359 W JP2010061359 W JP 2010061359W WO 2011002090 A1 WO2011002090 A1 WO 2011002090A1
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Prior art keywords
steryl glucoside
reaction mixture
reaction
fatty acid
glycerin
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PCT/JP2010/061359
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English (en)
French (fr)
Japanese (ja)
Inventor
孝信 片山
勝敏 山本
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花王株式会社
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Priority to CN201080027594.5A priority Critical patent/CN102459307B/zh
Priority to BRPI1015067-6A priority patent/BRPI1015067B1/pt
Publication of WO2011002090A1 publication Critical patent/WO2011002090A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/128—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J17/005—Glycosides

Definitions

  • the present invention relates to a method for producing fatty acid lower alkyl esters, glycerin and steryl glucoside from fats and oils.
  • Sterol glycosides and sterol glycoside esters such as steryl glucoside and acyl steryl glucoside are contained in fats and oils as natural fat and oil components, and their usefulness regarding their physiological activity has been pointed out.
  • various uses such as hair growth / hair growth (Japanese Patent Laid-Open No. 7-101835), reduction of blood lipid (Japanese Patent Laid-Open No. 7-118159), obesity prevention (Japanese Patent Laid-Open No. 7-107939) are disclosed.
  • As a technique for obtaining steryl glucoside from natural products organic solvent extraction from gypsum (Japanese Patent Laid-Open No.
  • the present invention comprises a step (hereinafter referred to as step 1) of obtaining a reaction mixture in which steryl glucoside is precipitated by subjecting a fat and oil containing steryl glucoside dissolved and a lower alcohol to a transesterification reaction.
  • the present invention relates to a method for producing steryl glucoside, a fatty acid lower alkyl ester, and glycerin having a step of separating rilglucoside (hereinafter referred to as step 2).
  • the term “steryl glucoside” may refer to steryl glucoside and acyl steryl glucoside.
  • the amount of steryl glucoside present in fats and oils is extremely small, and extraction methods using solvents such as JP-A-62-2238299, JP-A-2001-199992, and JP-A-7-062384 are in large quantities. It is not suitable as a method for stably supplying steryl glucoside. Moreover, a complicated process is required to separate steryl glucoside. On the other hand, Japanese Patent Application Laid-Open No. 2007-295848 can use only limited yeasts, and as a step of separating steryl glucoside from yeast cells, for example, extraction with an organic solvent needs to be performed.
  • Patent Document 8 does not describe obtaining a reaction product containing steryl glucoside or producing steryl glucoside together with a fatty acid lower alkyl ester or glycerin.
  • the present invention provides a method by which steryl glucoside, which is a useful physiologically active substance in fats and oils, can be easily and stably separated, and a fatty acid lower alkyl ester and glycerin can be simultaneously produced.
  • ADVANTAGE OF THE INVENTION According to this invention, the method which can isolate
  • steryl glucoside can be recovered by solid-liquid separation after alcohol removal. Steryl glucoside can be recovered more efficiently depending on the preferred conditions of transesterification reaction rate, residual concentration of unreacted alcohol, and separation temperature.
  • the present invention is a method for producing steryl glucoside and acyl steryl glucoside from fats and oils, or a method for producing steryl glucoside and acyl steryl glucosides, fatty acid lower alkyl esters and glycerin from fats and oils, and (I) Steryl Obtaining a reaction mixture containing a fatty acid lower alkyl ester corresponding to the lower alcohol and glycerin by transesterifying the fat and oil containing the glucoside in a dissolved state and the lower alcohol; (II) steryl glucoside in the reaction mixture; And (III) separating the steryl glucoside from the reaction mixture in which the steryl glucoside is precipitated.
  • step 1 (I) and (II) are performed.
  • the fats and oils used in Step 1 of the present invention are not limited to the type as long as they contain steryl glucoside in a dissolved state, but are vegetable oils and fats that contain a large amount of steryl glucoside and acyl steryl glucoside. Is preferred. More specifically, it is preferable to use coconut oil, palm oil, palm kernel oil, or the like. Generally, fats and oils exist in a state where steryl glucoside is dissolved at room temperature (25 to 40 ° C.).
  • the lower alcohol used in Step 1 of the present invention is a lower alcohol having 1 to 5 carbon atoms, and specifically, methanol, ethanol, propanol or the like can be used. In particular, methanol is preferable because it is easy to remove and uses a small amount of separation energy.
  • the transesterification reaction in Step 1 is performed in the presence of a catalyst.
  • the catalyst may be any catalyst that can be used for transesterification and esterification, and a homogeneous catalyst or a heterogeneous catalyst (for example, a powder catalyst or a molded product thereof, or an ion exchange resin) can be used.
  • a powder catalyst that can be used even at a high reaction temperature, or a molded product thereof, from the point that no soap by-product is produced.
  • a solid acid catalyst is preferable, a weak acid point having a strong acid point as defined below of 0.2 mmol / g-cat or less and a weak acid point as defined below of 0.3 mmol / g-cat or more.
  • a solid acid catalyst is more preferred.
  • Weak acid point A point where NH 3 is desorbed in the range of 100 to 250 ° C. in TPD (Temperature Programmed Desorption). Strong acid point: NH 3 is desorbed at a temperature higher than 250 ° C.
  • a preferred group includes solid catalyst shaped bodies having the following structure (A), structure (B) and metal atom (C).
  • examples of the inorganic phosphoric acid include condensed phosphoric acid such as orthophosphoric acid, metaphosphoric acid, and pyrophosphoric acid.
  • orthophosphoric acid is preferable.
  • the organic phosphoric acid represented by the general formula (1) or (2) phosphonic acid, phosphonic acid monoester, phosphinic acid, phosphoric monoester, phosphoric diester, phosphorous monoester , Phosphorous acid diesters, and the like, and a mixture thereof, preferably phosphonic acid.
  • Examples of the organic group R in the organic phosphoric acid include methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, n-hexyl, 2-ethylhexyl, octyl, dodecyl, octadecyl, etc.
  • An aryl group such as an alkyl group, phenyl or 3-methylphenyl is preferable, and these groups include an amino group, an alkoxy group, a carbonyl group, an alkoxycarbonyl group, a carboxylic acid group, a halogen group such as a chloro group, a phosphonic acid group, A group to which a sulfonic acid group or the like is bonded is also used.
  • the metal atom (C) aluminum is preferable from the viewpoint of performance and / or cost. For the purpose of improving selectivity and other performance, a small amount of metal atoms other than aluminum, gallium, and iron may be included.
  • metal atoms (C) contained in the catalyst are necessarily bonded to the structure (A) or the structure (B), and a part of the metal atoms (C) is a metal oxide or metal hydroxide. It may exist in the form of a thing or the like.
  • Another preferred group of weakly acidic solid acid catalysts used in the present invention is a molded product of a heterogeneous catalyst containing aluminum orthophosphate, and in particular, a pore volume having a pore diameter of 6 to 100 nm is 0.46 ml. / G or more and having an acid amount of 0.40 mmol / g or more is preferable.
  • a precipitation method a method of impregnating a metal oxide or hydroxide with inorganic phosphoric acid and organic phosphoric acid, an inorganic phosphate group in an inorganic aluminum phosphate gel is organic A method of substituting a phosphate group is used, and a precipitation method is preferred.
  • a supported catalyst by coexisting a high surface area carrier.
  • the carrier silica, alumina, silica alumina, titania, zirconia, diatomaceous earth, activated carbon, or the like can be used.
  • the proportion of the carrier in the catalyst is preferably 90% by mass or less.
  • a catalyst other than the weakly acidic solid acid catalyst a known homogeneous or heterogeneous catalyst can be used.
  • an alkali catalyst such as NaOH can be used.
  • the heterogeneous catalyst is not particularly limited as long as it has an alcoholysis reaction activity.
  • sodium carbonate, sodium hydrogen carbonate as described in JP-A-61-2254255, European Examples thereof include crystalline titanium silicate, crystalline titanium aluminum silicate, amorphous titanium silicate, and a corresponding zirconium compound as described in Japanese Patent No. 0623581.
  • the reaction mode of Step 1 may be either a tank reactor having a stirrer or a fixed bed reactor filled with a catalyst, but a fixed bed reactor is preferred because it does not require catalyst separation.
  • a transesterification reaction in Step 1 an ester of fatty acid derived from fat and oil and a lower alcohol and glycerin are produced.
  • the preferred reaction method in Step 1 is a solid catalytic reaction between a liquid fat and a lower alcohol, but it may be supplied in a gaseous state or in a liquid state depending on the reaction pressure and reaction temperature depending on the activity of the catalyst used. May be. Moreover, you may perform reaction in a several step.
  • the concentration of the fatty acid lower alkyl ester reaches the concentration at which steryl glucoside is precipitated.
  • the progress of the reaction depends on the activity of the catalyst used. When catalyst activity is high, steryl glucoside can be precipitated in a single reaction, but when using an existing catalyst with relatively low activity, a multistage reaction method is effective in consideration of economy. is there.
  • concentration of the fatty-acid lower alkyl ester in the oil phase of the reaction mixture obtained at the process 1 is 88 mass% or more. This concentration is measured by an analytical method such as a gas chromatograph.
  • the oil phase is a fat and fatty acid lower alkyl ester obtained by adding ion-exchanged water or warm water of ion-exchanged water to the reaction mixture after transesterification, removing glycerin and lower alcohol in the reaction mixture, and removing residual water. It is a mixture containing. If the reaction mixture is a mixture of an oil phase and a glycerin containing a fatty acid lower alkyl ester having a concentration of 88% by mass or more, steryl glucoside is easily precipitated, and separation and concentration are also preferable.
  • the transesterification reaction is such that the conversion rate of fatty acid derived from fat into fatty acid lower alkyl ester is 88% or higher, preferably 90% or higher, more preferably 92% or higher, particularly preferably 95% or higher. Is preferably performed.
  • the conversion rate is defined as saponification value calculated from the methyl ester concentration of the oil phase / saponification value of raw oil and fat ⁇ 100. If this conversion rate is 88% or more, the reaction mixture having the fatty acid lower alkyl ester concentration in the oil phase of 88% by mass or more can be easily obtained.
  • the concentration of the fatty acid lower alkyl ester, for example, methyl ester, in the oil phase can be measured by a known method.
  • the molar ratio of the lower alcohol to the fat depends on the catalytic activity, but is preferably 5 or more, more preferably 8 or more from the viewpoint of obtaining a good reaction rate. Also, from the viewpoint of economically reacting while suppressing the recovered amount of lower alcohol, it is preferably 50 or less, more preferably 40 or less, and even more preferably 30 or less.
  • the reaction temperature depends on the catalyst activity, but is preferably 100 ° C.
  • reaction pressure depends on the reaction type, the type of catalyst used, and the temperature, but is preferably 0.1 to 10 MPa-G (where G means gauge pressure), more preferably 0.5 to 8 MPa-G, 1.5 to 8 MPa-G is particularly preferable.
  • the reaction time in step 1 varies depending on the reaction conditions (reaction type, amount of catalyst, temperature, etc.), but in a reaction using a tank reactor, it is usually 2 to 10 hours.
  • the liquid space velocity (LHSV) based on fats and oils is 0.02 / hr from the viewpoint of increasing the productivity per unit volume of the reactor and conducting the reaction economically.
  • the above is preferable, and 0.1 / hr or more is more preferable.
  • 2.0 / hr or less is preferable and 1.0 / hr or less is more preferable.
  • the reaction mixture obtained in Step 1 is a mixture containing a fatty acid lower alkyl ester, unreacted fat, glycerin, lower alcohol, and steryl glucoside, and is in a uniform liquid phase or two-phase state depending on the reaction molar ratio. Form. Since the composition of the mixture of fat and lower alcohol before the transesterification reaction and the reaction mixture after the transesterification reaction varies, it is considered that steryl glucoside is likely to precipitate or precipitate. If steryl glucoside is precipitated in the obtained reaction mixture due to sufficient progress of the transesterification reaction, it can be used as it is in Step 2.
  • the present invention it is preferable to perform an operation for precipitating steryl glucoside in the reaction product, and it is preferable to remove steryl glucoside by removing lower alcohol (unreacted lower alcohol) in the reaction mixture.
  • the method for removing the lower alcohol is not particularly limited, and can be performed by a commonly used flash distillation or rectification operation. It is preferable to remove the lower alcohol until the content of the lower alcohol in the reaction mixture is 8% by mass or less, preferably 6% by mass or less, more preferably 4% by mass or less.
  • the method for removing the lower alcohol is not particularly limited, and a known method can be used. For example, by passing the reaction mixture through an evaporator, the lower alcohol present can be separated to 8 mass% or less.
  • the evaporation conditions are such that the lower alcohol content in the liquid reactant of the reaction mixture is 8% by mass or less, preferably 5% by mass or less, and more preferably 2% by mass or less.
  • the reaction mixture may optionally be flushed after being heated in advance.
  • the evaporation field can be adjusted as appropriate, for example, under reduced pressure conditions. Preferably, it can be carried out at a pressure of -0.993 MPa-G to 0.2 MPa-G and a separation temperature of 60 ° C to 160 ° C. It is also possible to obtain a reaction mixture in which steryl glucoside is precipitated by lowering the temperature of the reaction mixture.
  • the cooling temperature is a temperature at which steryl glucoside and acyl steryl glucoside are precipitated, and is not particularly limited as long as there is no problem with the heat resistance of the apparatus used in the separation in Step 2, but is preferably 55 ° C. or less, more preferably 53 C. or lower, more preferably 50.degree. C. or lower. Moreover, it is preferable that it is 30 degreeC or more, Preferably it is 35 degreeC or more from the raise of the viscosity of a reaction mixture being suppressed, and the time which filtration requires appropriately. Therefore, it is preferable to obtain a reaction mixture in which steryl glucoside is precipitated by adjusting the temperature of the reaction mixture to 30 to 55 ° C.
  • Step 2 is a step of separating steryl glucoside from the reaction mixture obtained in step 1 in which steryl glucoside is deposited. Furthermore, it is the process of isolate
  • the reaction mixture in Step 1 is a mixture containing an oil phase and a glycerin phase, but steryl glucoside is usually precipitated as a white precipitate containing steryl glucoside, acyl steryl glucoside, and the like.
  • steryl glucoside is usually precipitated as a white precipitate containing steryl glucoside, acyl steryl glucoside, and the like.
  • Separation of steryl glucoside from the reaction mixture is preferably carried out by filtration.
  • Filtration can be performed by a known method using a filtration device.
  • the filtration device is not particularly limited, but for continuous treatment, for example, a filtration method using a cartridge filter can be employed.
  • the reaction mixture is a mixture containing a fatty acid lower alkyl ester, fats and oils, and glycerin, any material can be used as the filter medium material used for filtration.
  • any material can be used as the filter medium material used for filtration.
  • polyethylene, polypropylene, polyester, and the like can be suitably used.
  • the coarseness of the filter medium may be such that the precipitated steryl glucoside does not pass, and preferably 100 ⁇ m or less, more preferably 50 ⁇ m or less, more preferably 20 ⁇ m or less.
  • the cartridge filter for example, CP-01, CPH-01 manufactured by Chisso Filter Co., Ltd. can be suitably used.
  • the processing amount per filtration area is reduced and becomes inefficient, so that it is preferably 0.5 ⁇ m or more, more preferably 2 ⁇ m or more, more preferably 5 ⁇ m. The above can be used suitably.
  • steryl glucoside may be purified and isolated from the filtration residue as necessary.
  • a fatty-acid lower alkyl ester and glycerol can be isolate
  • the separation method of the present invention can be incorporated into a process for producing a fatty acid lower alkyl ester from fats and oils and a lower alcohol, and does not require a complicated operation or apparatus for precipitating steryl glucoside. Very useful.
  • the separation method of the present invention can be carried out as a method for producing both fatty acid lower alkyl ester and steryl glucoside from fats and oils, and further producing three components of fatty acid lower alkyl ester, glycerin and steryl glucoside from fats and oils.
  • Step (d): Step of precipitating steryl glucoside in the reaction mixture obtained from step (c) (It may include a lower alcohol removing step)
  • the reaction article and operation in each process can be performed according to the above-mentioned preferable aspect and a
  • glycerin can also be recovered in the step (b).
  • the present invention comprises a step of transesterifying an oil and fat containing a steryl glucoside in a dissolved state with a lower alcohol to obtain a reaction mixture containing a fatty acid lower alkyl ester, glycerin and steryl glucoside, and from the reaction mixture
  • Catalyst production example 1 9.9 g of ethylphosphonic acid, 27.7 g of 85% orthophosphoric acid, and 112.5 g of aluminum nitrate (9 hydrate) were dissolved in 1000 g of water. At room temperature, an aqueous ammonia solution was added dropwise to the mixed solution to raise the pH to 5. On the way, a gel-like white precipitate was formed. The precipitate was filtered, washed with water, dried at 110 ° C. for 15 hours, and pulverized to 60 mesh or less.
  • catalyst 1 10% alumina sol was added to the pulverized catalyst, and extrusion molding of 2.5 mm ⁇ was performed. This was calcined at 250 ° C. for 3 hours to obtain a solid acid catalyst forming catalyst (hereinafter referred to as catalyst 1). The obtained catalyst had a weak acid point of 1 mmol / g-cat and a strong acid point below the detection limit.
  • catalyst 1 Two reaction tubes having an inner diameter of 35.5 mm ⁇ and a length of 800 mm were connected in series, and 500 cc each of the catalyst 1 was packed for measuring the temperature.
  • the reaction temperature is 170 ° C.
  • LHSV is 0.4
  • reaction pressure is 3
  • Methanol was fed at a 10-fold molar ratio with respect to the fat (all the fat was converted to triglyceride).
  • the oil and fat flowed 112 times the volume of the catalyst 1.
  • an evaporator was used to evaporate methanol at a pressure of ⁇ 0.9867 MPa-G (100 mmHg) and 100 ° C.
  • the methanol content in the oil phase was 1.0% by mass or less. Then, the anti-end liquid was cooled and allowed to stand at 50 ° C., and separated into a methyl ester phase and a glycerin phase. In this reaction mixture, steryl glucoside was not precipitated. The methyl ester concentration of the obtained methyl ester phase was measured by gas chromatography and found to be 85.3%. Moreover, the obtained glycerol was 76% with respect to the theoretical production amount.
  • the theoretical production amount of glycerol is calculated
  • Example 1 The methyl ester phase obtained in Comparative Example 1 was reacted with methanol again using the same reaction tube as in Comparative Example 1. The reaction was conducted at a reaction temperature of 170 ° C., LHSV of 0.8, and a reaction pressure of 3.0 MPa-G.
  • Methanol was fed at a 10-fold molar ratio with respect to the fat (all the fat was converted to triglyceride).
  • the amount of methyl ester phase passed was 102 times the volume of catalyst 1.
  • the obtained anti-end liquid was evaporated using an evaporator at a pressure of ⁇ 0.9867 MPa-G (100 mmHg) and 100 ° C.
  • the methanol content in the oil phase was 1.0% by mass or less.
  • the anti-end solution was cooled to 50 ° C. At this time, a white precipitate of steryl glucoside was suspended between the methyl ester phase and the glycerin phase.
  • a filter paper No.
  • Comparative Example 3 In a tubular reactor filled with the catalyst 1, purified coconut oil having an acid value of 8.5 containing steryl glucoside at a concentration of 45 mg / kg is LHSV 0.5, reaction temperature is 175 ° C., reaction pressure is 4.0 MPa-G, liquid The reaction was carried out by supplying a molar ratio of 10 moles of methanol. At this time, the passing ratio with respect to the catalyst volume was 738 times. The reaction mixture after the reaction was continuously removed with methanol at a pressure of 0 MPa-G and 130 ° C. using a flash distillation can. The methanol concentration in the reaction mixture after removal of methanol was 1.8% by mass. The reaction mixture after removal of methanol was continuously cooled to 60 ° C.
  • Example 2 After separating the methyl ester phase from the reaction mixture after filtration obtained in Comparative Example 3, it was tube-shaped again under the conditions of LHSV 1.1, reaction temperature 173 ° C., reaction pressure 4.0 MPa-G, and a molar ratio of methanol of 10 mol. The reaction was carried out using a reactor to obtain a reaction mixture in which the methyl ester concentration in the methyl ester phase was 98.1% and the glycerin production amount was 90.7% of the theoretical production amount. The passing ratio with respect to the catalyst volume was 1616 times.
  • This mixture was continuously introduced into a flash distillation can and subjected to flash separation at 120 ° C. and 0 MPa-G to obtain a reaction mixture having a methanol concentration of 2.1%. Furthermore, after continuously cooling to 45 ° C., the solution was passed through a cartridge filter (CP-01 manufactured by Chisso Filter Co., Ltd.) to obtain a white concentrated composition containing 82% by mass of steryl glucoside.
  • a cartridge filter CP-01 manufactured by Chisso Filter Co., Ltd.
  • Comparative Example 4 In a tubular reactor filled with the catalyst 1, purified coconut oil having an acid value of 8.5 containing steryl glucoside at a concentration of 45 mg / kg is LHSV 0.4, reaction temperature is 166 ° C., reaction pressure is 4.0 MPa-G, liquid The reaction was carried out by supplying a molar ratio of 10 moles of methanol. At this time, the liquid passage ratio with respect to the catalyst volume was 38 times. The reaction mixture after the reaction was continuously removed with methanol at a pressure of 0 MPa-G and 130 ° C. using a flash distillation can. The methanol concentration in the reaction mixture after removal of methanol was 1.8% by mass. The reaction mixture after removal of methanol was continuously cooled to 40 ° C.
  • Comparative Example 5 After separating the methyl ester phase from the reaction mixture after filtration obtained in Comparative Example 4, it was tube-shaped again under the conditions of LHSV 1.5, reaction temperature 182 ° C., reaction pressure 4.0 MPa-G, and a molar ratio of methanol of 10 mol. Reaction was performed using a reactor to obtain a reaction mixture in which the methyl ester concentration in the methyl ester phase was 97.9%. The passing ratio with respect to the catalyst volume was 392 times. This mixture was continuously introduced into a flash distillation can and subjected to flash separation at 120 ° C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Fats And Perfumes (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/JP2010/061359 2009-06-30 2010-06-28 脂肪酸低級アルキルエステル、グリセリン及びステリルグリコシドの製造法 WO2011002090A1 (ja)

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Application Number Priority Date Filing Date Title
CN201080027594.5A CN102459307B (zh) 2009-06-30 2010-06-28 脂肪酸低级烷基酯、甘油以及甾醇糖苷的制造法
BRPI1015067-6A BRPI1015067B1 (pt) 2009-06-30 2010-06-28 Método para produzir um alquil éster inferior de ácido graxo, glicerol e esteril glicosídeo.

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JP2009-155423 2009-06-30
JP2009155423 2009-06-30

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JP (1) JP5618648B2 (enrdf_load_stackoverflow)
CN (1) CN102459307B (enrdf_load_stackoverflow)
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MY (1) MY162664A (enrdf_load_stackoverflow)
WO (1) WO2011002090A1 (enrdf_load_stackoverflow)

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CN116103167A (zh) * 2023-02-09 2023-05-12 南京工业大学 一种异常威克汉姆酵母菌及其分离方法和应用
US11950828B2 (en) 2012-02-08 2024-04-09 Avenu Medical, Inc. Intravascular arterial to venous anastomosis and tissue welding catheter

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EP2665537A4 (en) * 2011-01-21 2014-07-02 Perstorp Ab METHOD OF CLEANING BIODIESEL USING A SELF-CLEANING FILTER
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CN102459307A (zh) 2012-05-16
JP2011026567A (ja) 2011-02-10
CN102459307B (zh) 2014-11-26

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