WO2011099406A1 - 油脂用流動性向上剤 - Google Patents
油脂用流動性向上剤 Download PDFInfo
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- WO2011099406A1 WO2011099406A1 PCT/JP2011/052124 JP2011052124W WO2011099406A1 WO 2011099406 A1 WO2011099406 A1 WO 2011099406A1 JP 2011052124 W JP2011052124 W JP 2011052124W WO 2011099406 A1 WO2011099406 A1 WO 2011099406A1
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- WIPO (PCT)
- Prior art keywords
- oils
- fats
- oil
- polymer
- fluidity
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/236—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof
- C10L1/2364—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derivatives thereof homo- or copolymers derived from unsaturated compounds containing amide and/or imide groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
- C08F220/24—Esters containing halogen containing perhaloalkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
- C08F222/402—Alkyl substituted imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
- C10L10/16—Pour-point depressants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L2200/00—Components of fuel compositions
- C10L2200/04—Organic compounds
- C10L2200/0461—Fractions defined by their origin
- C10L2200/0469—Renewables or materials of biological origin
- C10L2200/0484—Vegetable or animal oils
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
- C10L2230/22—Function and purpose of a components of a fuel or the composition as a whole for improving fuel economy or fuel efficiency
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L2250/00—Structural features of fuel components or fuel compositions, either in solid, liquid or gaseous state
- C10L2250/04—Additive or component is a polymer
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L2270/00—Specifically adapted fuels
- C10L2270/02—Specifically adapted fuels for internal combustion engines
- C10L2270/026—Specifically adapted fuels for internal combustion engines for diesel engines, e.g. automobiles, stationary, marine
Definitions
- the present invention relates to a flowability improver for fats and oils for improving the flowability of fats and oils when the fats and oils are used as a fuel.
- Patent Document 1 shows a method of using fat and oil subjected to ozone treatment and light irradiation treatment for modification
- Patent Document 2 shows a method of using a hydrocarbon composition obtained by subjecting fat and oil to hydrogenation treatment. It is done.
- each method still has the problem that it consumes a lot of energy in the reforming step or requires equipment for reforming.
- Patent Document 3 discloses a method of using an alkyl methacrylate polymer having a specific carbon chain length and molecular weight distribution as a flowability improver for fats and oils. However, this method could not sufficiently improve the liquidity and was not satisfactory.
- An object of the present invention is to provide a flowability improver for fats and oils that can sufficiently improve the flowability of fats and oils when the fats and oils themselves are used as a fuel.
- the present inventors have found that a polymer having a specific structure improves the fluidity of fats and oils, and has completed the present invention.
- the fluidity improver for fats and oils according to the present invention is a polymer comprising the structural units (I), (II) and (III) and having a weight average molecular weight of 5,000 to 100,000, which is a structural unit
- the molar fraction a of (I) is 0.4 to 0.8
- the molar fraction b of the structural unit (II) is 0.1 to 0.3
- the molar fraction c of the structural unit (III) is 0.1 It consists of a polymer which is ⁇ 0.3.
- numerical values at both ends of the symbol “to” are included in the range, for example, “A to B” represents A or more and B or less.
- R 1 represents a linear saturated alkyl group having 12 to 16 carbon atoms
- R 2 is a methyl group or a hydrogen atom
- R 3 is a linear saturated alkyl group having 6 to 18 carbon atoms
- R 4 represents a linear saturated alkyl group having 6 to 20 carbon atoms.
- liquidity of fats and oils can fully be improved and the fats and oils which are excellent in fluidity
- the fluidity improver for fats and oils according to the present invention is a structural unit (I), a structural unit (II) and a structural unit (III) each having a specific molar fraction It consists of a polymer which it has.
- the polymer having each structural unit is obtained by polymerizing an alkyl (meth) acrylate, an ⁇ -olefin, and maleic anhydride as monomers, and then forming an anhydride ring and a primary polymer in the obtained polymer. It can be obtained by reacting with an amine and imidation.
- each constituent unit may be either a block copolymer or a random copolymer.
- alkyl (meth) acrylate represents both alkyl methacrylate and alkyl acrylate.
- the alkyl (meth) acrylate used as a monomer is a monomer corresponding to the structural unit (I), and the alkyl group is a (meth) acrylate having a linear saturated alkyl group having 12 to 16 carbon atoms. Specific examples thereof include dodecyl (meth) acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate, pentadecyl (meth) acrylate and hexadecyl (meth) acrylate.
- One type selected from these alkyl (meth) acrylates may be used alone, or two or more types may be used in combination. If the carbon number of the alkyl group is less than 12 or more than 16, the fluidity of the oil is not sufficiently obtained, which is not preferable.
- the ⁇ -olefin used as a monomer is a monomer corresponding to the structural unit (II), and is a linear ⁇ -olefin having 8 to 20 carbon atoms. Specific examples thereof include ⁇ -octene, ⁇ -decene, ⁇ -dodecene, ⁇ -tetradecene, ⁇ -hexadecene, ⁇ -eicosene and the like, and in particular an ⁇ -olefin having 10 to 16 carbon atoms has an effect of improving fluidity Is preferable because it is high.
- One type selected from these ⁇ -olefins may be used alone, or two or more types may be used in combination.
- a primary amine to be reacted with an anhydrous ring in a polymer derived from maleic anhydride used as a monomer is a primary amine having a linear saturated alkyl having 6 to 20 carbon atoms, and as a specific example, And hexylamine, octylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, octadecylamine, eicosylamine and the like, and in particular, it is preferable to use an alkyl having 8 to 14 carbon atoms.
- Grade amines are preferred because they are highly effective in improving fluidity.
- One type selected from these primary amines may be used alone, or two or more types may be used in combination.
- the molar fraction of each structural unit is 0.4 to 0.8 for the molar fraction a of the structural unit (I), 0.1 to 0.3 for the molar fraction b for the structural unit (II), and
- the molar fraction c of III) is 0.1 to 0.3.
- the effect of improving the fluidity is high. preferable. If the molar fractions a, b and c are out of the above-mentioned range, it is not preferable because sufficient fluidity of the oil can not be obtained.
- the flowability improver of the present invention comprises a polymer having the above-mentioned structural units (I), (II) and (III) in specific molar fractions.
- the weight average molecular weight of such a polymer is 5,000 to 100,000, preferably 10,000 to 50,000. If the weight average molecular weight is less than 5,000, sufficient fluidity may not be obtained, and if it exceeds 100,000, the handleability of the polymer may be deteriorated.
- the weight average molecular weight can be determined in terms of polystyrene by measurement by gel permeation chromatography using tetrahydrofuran as a developing solvent.
- the fluidity improver of the present invention can be obtained by polymerizing the monomers corresponding to each constituent unit.
- the polymerization method is not particularly limited, solution polymerization using a radical polymerization initiator is preferable because of the easiness of polymerization and the excellent handleability of the polymer.
- a radical polymerization initiator an azo-based or peroxide-based one is used, and as a solvent, a hydrocarbon-based or aromatic-based solvent which is excellent in the solubility of monomers and polymers is used.
- a hydrocarbon-based or aromatic-based solvent which is excellent in the solubility of monomers and polymers is used.
- oils and fats to which the fluidity improver of the present invention may be added may be any of vegetable oils and fats and animal oils and fats, for example, rapeseed oil, soybean oil, safflower oil, sunflower oil, palm oil, palm olein oil, palm kernel oil, coconut oil , Jatropha oil, beef tallow, pork fat and the like. These fats and oils may be used alone or in combination of two or more.
- the flowability improver of the present invention is usually used by adding 0.001 to 1% by weight to fats and oils.
- a commonly used fuel additive may be used in combination as long as the effects of the present invention are not impaired.
- a flow improver with high exothermic peak temperature measured by differential scanning calorimeter (DSC) is used, and conversely, for fats and oils with low pour points, exothermic peak It is preferred to use a flow improver which has a low temperature.
- the pour point (T 1 ) of the fat and oil and the exothermic peak temperature (T 2 ) of the fluidity improver are in the following relational expression (1), a more excellent fluidity improvement effect can be obtained.
- the temperature in the system was once lowered to 40 ° C., and then 40.32 g (0.312 mol) of n-octylamine and 40 ml of xylene were charged with stirring. Then, the temperature was raised to 110 ° C., and the mixture was held at 110 ° C. for 3 hours for imidation reaction to obtain a 50% by weight xylene solution of the light yellow polymer 1.
- polymerization was performed in the same manner as in Example 1 using the monomers shown in Table 1 to produce polymers 2 to 9.
- the weight average molecular weight was measured by gel permeation chromatography (Tosoh Corp. HLC-8220 GPC) using tetrahydrofuran as a developing solvent, and was determined in terms of polystyrene.
- Tosoh Corp. TSK gel SuperH4000 (6 mm ID ⁇ 15 cm), TSK gel Super H2000 (6 mm ID ⁇ 15 cm) and TSK gel Super H1000 (6 mm ID ⁇ 15 cm) were used.
- the exothermic peak temperature was measured by first weighing 10 mg of the polymer in a sample pan (made by Seiko Instruments Inc., aluminum) with a differential scanning calorimeter (EXSTAR 6000, manufactured by Seiko Instruments Inc.), and measuring 100 mg of the polymer. The temperature was raised to ° C, and then held at 100 ° C for 10 minutes. Next, the exothermic peak obtained when the polymer was cooled was measured at 10 ° C./min from 100 ° C. to ⁇ 60 ° C. The exothermic peak temperature was determined as the temperature at the inflection point of the DDSC (differential value of DSC) curve at the exothermic peak in the DSC curve, that is, the temperature when the DDSC value became zero.
- DDSC differential scanning calorimeter
- the pour points of the oils 1 to 5 in Table 2 were measured, and the pour points were similarly described in Table 2. Furthermore, the polymers 1 to 9 in Table 1 were added to the oils and fats 1 to 5, and the pour point was measured. The pour point after addition and the difference in pour point before and after addition are shown in Tables 3 and 4. The pour point was measured at 1 ° C. intervals according to JIS K-2269.
- the flowability of fats and oils can be improved. Therefore, when using the animal and vegetable fat and oil itself as a boiler, a diesel engine and a fuel for heating, the handleability of the fat and oil can be improved by adding the flowability improver of the present invention to the fat and oil.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Lubricants (AREA)
Abstract
Description
R2:メチル基もしくは水素原子、
R3:炭素数6~18の直鎖飽和アルキル基、
R4:炭素数6~20の直鎖飽和アルキル基を表す。〕
本発明における油脂用流動性向上剤(以下、単に「流動性向上剤」とも表記する。)は、構成単位(I)、構成単位(II)および構成単位(III)をそれぞれ特定のモル分率で有する重合体からなる。各構成単位を有する重合体は、単量体として、アルキル(メタ)アクリレートと、α-オレフィンと、無水マレイン酸とを用いて重合した後、得られた重合体中の無水環と第一級アミンとを反応させてイミド化することによって、得ることができる。または、アルキル(メタ)アクリレートと、α-オレフィンと、マレイン酸イミドとを共重合させて得ることもできる。本発明においては、重合体を得た後にイミド化する方法の方が本発明の重合体を得易いので好ましい。なお、本発明の重合体は、各構成単位がブロック状の共重合体またはランダム状の共重合体のどちらでも構わない。また、アルキル(メタ)アクリレートは、アルキルメタクリレートおよびアルキルアクリレートの双方を表す。
また、無水マレイン酸を単量体として使用した重合体をイミド化する場合は、重合体を得たのち、これに無水マレイン酸1モル当たり、第一級アミンを0.7~1.2モルの割合で加えて、70~170℃でイミド化反応を行うことによって、上記の構成単位(I)、(II)及び(III)からなる重合体が得られる。
〔重合体1の製造例〕
攪拌装置、冷却管及び不活性ガス導入口を備えた反応器の中に、キシレン150ミリリットル、ドデシルアクリレート100g(0.416モル)、C16α-オレフィン69.71g(0.312モル)、無水マレイン酸30.60g(0.312モル)を仕込み、攪拌しながら120℃まで昇温した。次いで、重合開始剤としてターシャリーブチルパーオキシベンゾエート1.54g(0.009モル)をキシレン50ミリリットルに希釈し、滴下管に仕込んだ。重合開始剤を2時間掛けて滴下し、120℃で重合反応を行った。滴下後2.5時間熟成を行って、淡黄色の重合物溶液を得た。
これに対して、表4に示すように、本発明の規定から外れる重合体6~9の流動性向上剤を油脂に添加しても、油脂の流動点を低下させる作用が本発明よりも弱かったことが分かる。
例えば、実施例7,9,11,14と比較例4,6とを対比すると、いずれも油脂4(ヤシ油)に対して0.50重量%の重合体を添加するという条件は同じであるが、比較例4,6では油脂の流動点が低下しなかったのに対して、実施例7,9,11,14では油脂の流動点が2℃~4℃低下した。すなわち、本発明に係る重合体1~5の流動性向上剤を油脂に添加することによって、油脂の流動性が向上することが確認された。
Claims (1)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11742151.1A EP2535396B1 (en) | 2010-02-10 | 2011-02-02 | Method with fluidity improver for fats and vegetable oils |
CN201180015363.7A CN103097498B (zh) | 2010-02-10 | 2011-02-02 | 油脂用流动性改进剂 |
US13/578,232 US9012583B2 (en) | 2010-02-10 | 2011-02-02 | Flow improver for oils and fats |
JP2011553808A JP5737190B2 (ja) | 2010-02-10 | 2011-02-02 | 油脂用流動性向上剤 |
KR1020127022570A KR101777577B1 (ko) | 2010-02-10 | 2011-02-02 | 유지용 유동성 향상제 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2010-027949 | 2010-02-10 | ||
JP2010027949 | 2010-02-10 |
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WO2011099406A1 true WO2011099406A1 (ja) | 2011-08-18 |
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PCT/JP2011/052124 WO2011099406A1 (ja) | 2010-02-10 | 2011-02-02 | 油脂用流動性向上剤 |
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US (1) | US9012583B2 (ja) |
EP (1) | EP2535396B1 (ja) |
JP (1) | JP5737190B2 (ja) |
KR (1) | KR101777577B1 (ja) |
CN (1) | CN103097498B (ja) |
WO (1) | WO2011099406A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2012133502A1 (ja) * | 2011-03-29 | 2012-10-04 | 日油株式会社 | 燃料油用流動性向上剤及び燃料油組成物 |
Families Citing this family (1)
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RU2690940C2 (ru) * | 2014-11-27 | 2019-06-07 | Басф Се | Сополимер и его применение для уменьшения кристаллизации кристаллов парафина в топливах |
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Also Published As
Publication number | Publication date |
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JP5737190B2 (ja) | 2015-06-17 |
JPWO2011099406A1 (ja) | 2013-06-13 |
CN103097498B (zh) | 2015-05-06 |
CN103097498A (zh) | 2013-05-08 |
KR20120121906A (ko) | 2012-11-06 |
EP2535396B1 (en) | 2017-04-19 |
KR101777577B1 (ko) | 2017-09-13 |
EP2535396A4 (en) | 2013-08-21 |
US9012583B2 (en) | 2015-04-21 |
US20120316306A1 (en) | 2012-12-13 |
EP2535396A1 (en) | 2012-12-19 |
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