JP2009057510A - Stabilized bio-diesel fuel - Google Patents
Stabilized bio-diesel fuel Download PDFInfo
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- JP2009057510A JP2009057510A JP2007227642A JP2007227642A JP2009057510A JP 2009057510 A JP2009057510 A JP 2009057510A JP 2007227642 A JP2007227642 A JP 2007227642A JP 2007227642 A JP2007227642 A JP 2007227642A JP 2009057510 A JP2009057510 A JP 2009057510A
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- 239000003225 biodiesel Substances 0.000 title claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 7
- -1 quinoline compound Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 claims description 3
- 235000019285 ethoxyquin Nutrition 0.000 claims description 3
- 239000002283 diesel fuel Substances 0.000 claims description 2
- 239000000446 fuel Substances 0.000 abstract description 11
- 230000003647 oxidation Effects 0.000 abstract description 10
- 238000007254 oxidation reaction Methods 0.000 abstract description 10
- 239000003963 antioxidant agent Substances 0.000 abstract description 8
- 230000003078 antioxidant effect Effects 0.000 abstract description 8
- 239000007788 liquid Substances 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 7
- 238000006116 polymerization reaction Methods 0.000 abstract description 5
- 230000006866 deterioration Effects 0.000 abstract description 4
- 239000002828 fuel tank Substances 0.000 abstract description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 3
- 230000036506 anxiety Effects 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000008157 edible vegetable oil Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 2
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 239000002551 biofuel Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
- 239000008162 cooking oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000008164 mustard oil Substances 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Liquid Carbonaceous Fuels (AREA)
Abstract
Description
本発明は、安定化されたバイオディーゼル燃料に関する。 The present invention relates to a stabilized biodiesel fuel.
近年、二酸化炭素増加による地球温暖化問題や排気ガスなどによる酸性雨の問題から、バイオマスエネルギーが関心を集めている。バイオ燃料は、カーボンニュートラルな燃料として、二酸化炭素排出量の削減、化石燃料の消費量を削減するための対策として、自動車燃料への普及が世界で拡大している。中でもバイオディーゼル燃料は、動植物性油脂または廃食用油をメチルエステル化することでディーゼルエンジンを稼動させることが出来る、軽油の代替燃料である。しかし、バイオディーゼル燃料は油脂の特徴をそのまま受け継いでいるため、軽油に比べて酸化劣化しやすい。バイオディーゼルが酸化劣化することによりカルボン酸が発生し、燃料ホースを腐食させてしまうという問題や、バイオディーゼルの酸化重合により発生するガム状物質が、燃料タンクやエンジン内で種々のトラブルを引き起こすという問題があることが知られている。 In recent years, biomass energy has attracted attention due to global warming due to an increase in carbon dioxide and acid rain due to exhaust gas. Biofuels are becoming carbon-neutral fuels, and their use in automobile fuels is expanding worldwide as a measure to reduce carbon dioxide emissions and fossil fuel consumption. In particular, biodiesel fuel is an alternative fuel for light oil that can operate a diesel engine by methyl esterifying animal or vegetable oil or waste edible oil. However, since biodiesel fuel inherits the characteristics of fats and oils as it is, it is more susceptible to oxidative degradation than light oil. The problem that biodiesel is oxidatively deteriorated to generate carboxylic acid and corrodes the fuel hose, and the gum-like substance generated by oxidative polymerization of biodiesel causes various troubles in the fuel tank and engine. There are known problems.
そのような対策の一つとして、各種の酸化防止剤に使用が提案されている。例えば、各種のフェノール系化合物の使用が提案されている。（特許文献１）しかしながら、これらの化合物は、常温で液体であるバイオディーゼル燃料との混合の際に、常温で固体であったり、液体であっても粘度が著しく高いなどするため、均一な混合の達成が困難であったり、低温時、特に寒冷地での使用に析出化の発生などの不安がつきまとうとの欠陥が予測される。そのため、常温で液状の物質で、低温に遭遇しても、固体化しにくい酸化防止剤による安定化が望まれている。
本発明の目的は、常温で液体であるバイオディーゼル燃料との混合時に、容易に均質な混合が可能であり、かつ、寒冷地での使用に不安がより少ない酸化防止剤を使用することにより、上記の問題を解決しようとするものである。更に、多種多様な油種から製造されるバイオディーゼル燃料に酸化安定性を付与し、貯蔵安定性および耐熱安定性を付与しようとするものである。また、酸化劣化を防止することにより、エンジンや燃料タンク内での燃料の酸化重合により発生するガム状物質によるトラブルを防止するほか、燃料ホースなどの自動車部品の劣化を防止しようとするものである。 The object of the present invention is to use an antioxidant that can be easily mixed homogeneously when mixed with biodiesel fuel that is liquid at room temperature and has less anxiety for use in cold regions. It is an attempt to solve the above problem. Furthermore, the present invention intends to impart oxidation stability to biodiesel fuel produced from a wide variety of oil types, thereby imparting storage stability and heat stability. In addition to preventing oxidative deterioration, it is intended to prevent troubles caused by gum-like substances generated by oxidative polymerization of fuel in engines and fuel tanks, as well as prevent deterioration of automobile parts such as fuel hoses. .
本発明者等は、種々検討の結果、 酸化防止剤として、バイオディーゼル燃料に特定のキノリン系またはパラフェニレンジアミン系のアミン系酸化防止剤を添加することで、上記の目的を達成できることを見出し、本発明を完成させたものである。 As a result of various studies, the present inventors have found that the above-described object can be achieved by adding a specific quinoline-based or paraphenylenediamine-based amine antioxidant to biodiesel fuel as an antioxidant, The present invention has been completed.
本発明に係る安定化されたバイオディーゼル燃料によれば、酸化安定性が付与されることにより、貯蔵安定性および耐熱安定性が増し、その結果として、エンジンや燃料タンク内での燃料の酸化重合により発生するガム状物質によるトラブル発生の防止や、燃料ホースなどの自動車部品の劣化が防止されるという効果が発揮される。 According to the stabilized biodiesel fuel according to the present invention, by providing oxidation stability, storage stability and heat stability are increased, and as a result, oxidative polymerization of fuel in an engine or a fuel tank. This prevents the occurrence of troubles caused by the gum-like substances generated by the above-mentioned and prevents the deterioration of automobile parts such as fuel hoses.
本発明におけるバイオディーゼル燃料の原料としては、菜種油、ごま油、大豆油、とうもろこし油、ひまわり油、ココナッツ油、紅花油、ピーナッツ油、綿実油、アマニ油、マスタード油などの植物性油脂類、牛脂、豚油、鯨油、魚油などの動物性油脂、およびこれらの廃食油や、これらの油脂類の製造工程で得られるダーク油、モノグリセリド、ジグリセリド、遊離脂肪酸などの脂肪酸誘導体類から得られる脂肪酸アルキルエステルなどのバイオディーゼル燃料を挙げることができるが、こられに限られるものではない。また、バイオディーゼル燃料に、一般的なディーゼル燃料が混合されているものであってもよい。 The raw material for biodiesel fuel in the present invention includes vegetable oils such as rapeseed oil, sesame oil, soybean oil, corn oil, sunflower oil, coconut oil, safflower oil, peanut oil, cottonseed oil, linseed oil, and mustard oil, beef fat, pork Fatty acid alkyl esters obtained from fatty acid derivatives such as animal oils and fats such as oil, whale oil and fish oil, and these waste cooking oils and dark oils, monoglycerides, diglycerides and free fatty acids obtained in the production process of these fats and oils Biodiesel fuel can be mentioned, but is not limited to this. Moreover, general diesel fuel may be mixed with biodiesel fuel.
また式（Ｉ）：
式（Ｉ）で表されるキノリン系化合物、及び式（ＩＩ）で表されるパラフェニレンジアミン系化合物のバイオディーゼル燃料中への添加量は、通常は、５００〜３０００ｐｐｍ、好ましくは、１０００〜２５００である。３０００ｐｐｍを超えて添加しても、添加量の増量に見合った効果の向上は少なく、５００ｐｐｍ未満では、十分な酸化防止効果が得られない。 The amount of the quinoline compound represented by the formula (I) and the paraphenylenediamine compound represented by the formula (II) added to the biodiesel fuel is usually 500 to 3000 ppm, preferably 1000 to 2500. It is. Even if it exceeds 3000 ppm, the improvement of the effect commensurate with the increase of the addition amount is small, and if it is less than 500 ppm, a sufficient antioxidant effect cannot be obtained.
以下に試験例を挙げて本発明を更に具体的に説明するが、本発明は、これら試験例によって、何ら限定されるものではない。 Hereinafter, the present invention will be described more specifically with reference to test examples. However, the present invention is not limited to these test examples.
［試験例］
バイオディーゼル燃料として、下記の表１に示すように、廃食用油から調製したものであるバイオディーゼル燃料Ａと菜種油から調製したバイオディーゼル燃料Ｂに下記の化合物をそれぞれ所定量添加して、ＥＵ規格によるランシマット法（ＥＮ１４１１２）によりそれぞれの酸化防止効果を測定した。
使用化合物Ａ：Ｎ−（１−メチルヘプチル）−Ｎ’−フェニレンジアミン（本願化合物）、
使用化合物Ｂ：６−エトキシ−２，２，４−トリメチル−１，２−ジヒドロキノリン（本願化合物）、
使用化合物Ｃ：、２，６−ジ−ｔｅｒｔ−ブチル−４−メチルフェノール（ＢＨＴ）（対照化合物）、
使用化合物Ｄ：２，２’−メチレンビス［６−ｔｅｒｔ−ブチル−４−メチルフェノール］（ＭＢＰ）（対照化合物）、
使用化合物Ｅ：ｔｅｒｔ−ブチルハイドロキノン（ＴＢＨ）（対照化合物）
[Test example]
As shown in the following Table 1, as biodiesel fuel, the following compounds are respectively added in predetermined amounts to biodiesel fuel A and biodiesel fuel B prepared from rapeseed oil, which are prepared from waste edible oil. Each antioxidation effect was measured by the Rancimat method (EN14112).
Compound A: N- (1-methylheptyl) -N′-phenylenediamine (the present compound),
Compound B used: 6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline (compound of the present application),
Compound C used: 2,6-di-tert-butyl-4-methylphenol (BHT) (control compound),
Compound D used: 2,2′-methylenebis [6-tert-butyl-4-methylphenol] (MBP) (control compound),
Compound E: tert-butyl hydroquinone (TBH) (control compound)
ランシマット法の概要
試料約３ｇを反応容器に入れ、１１０℃に加熱しながら、その中に清浄空気を送り込み、揮発性分解物を水中に捕集し、捕集水の導電率が急激に変化する折曲点までの時間（誘導時間）を測定する。すなわち、試料であるバイオディーゼル燃料の酸化により生成する分解生成物量（ギ酸や酢酸が主成分とされている。）の経時変化を測定することにより、誘導時間を決定する。この値は、バイオディーゼル燃料の酸化に係る他のパラメーター（過酸化物価、動粘度、酸価等）との連関性が認められており、酸化安定性を評価するのによい指標であるとして評価試験に使用されている。なお、ヨーロッパでのバイオディーゼル燃料に関する規格（ＥＮ１４２１４）では、この方法による基準値は６時間以上とされている。
Outline of the Rancimat method About 3 g of a sample is put in a reaction vessel, heated to 110 ° C., clean air is sent into it, volatile decomposition products are collected in water, and the conductivity of the collected water changes abruptly. Measure the time to the bending point (induction time). That is, the induction time is determined by measuring the change over time of the amount of decomposition products (formic acid and acetic acid are the main components) produced by oxidation of the biodiesel fuel that is the sample. This value is recognized as being a good indicator for evaluating oxidation stability because it is recognized to be linked to other parameters (peroxide value, kinematic viscosity, acid value, etc.) related to oxidation of biodiesel fuel. Used for testing. In addition, in the standard (EN14214) regarding biodiesel fuel in Europe, the reference value by this method is set to 6 hours or more.
評価結果は以下の表１に示す。 The evaluation results are shown in Table 1 below.
表１の結果より、酸化防止剤を添加することで誘導時間が一様に延びていることがわかる。特に本発明に係る化合物Ａは、従来品であるフェノール系の酸化防止剤Ｃ、Ｄ、Ｅよりも誘導時間が長く、酸化安定性が高い。本発明に係る化合物Ｂの性能も確認出来た。また、Ｃ、Ｄ、Ｅは固体物質であるのに対し、本発明に係る化合物Ａ及びＢは液状物質であり、燃料添加剤として使用するに当たり添加作業上有利であり、溶け残りによるトラブルなども防止できる。バイオディーゼル燃料の酸化を防止し、安定した燃料として使用することが期待できる。 From the results in Table 1, it can be seen that the induction time is uniformly extended by adding the antioxidant. In particular, the compound A according to the present invention has a longer induction time and higher oxidation stability than the conventional phenolic antioxidants C, D and E. The performance of the compound B according to the present invention was also confirmed. Further, C, D, and E are solid substances, whereas the compounds A and B according to the present invention are liquid substances, which are advantageous in addition work when used as a fuel additive, and troubles due to undissolved parts are also caused. Can be prevented. It can be expected to be used as a stable fuel by preventing the oxidation of biodiesel fuel.
本発明に係る安定化されたバイオディーゼル燃料は、酸化防止に使用される化合物が常温で液体であることから、容易に均質な混合が可能であり、かつ、寒冷地での使用に不安もなく、産業上有用である。 In the stabilized biodiesel fuel according to the present invention, the compound used for oxidation prevention is liquid at room temperature, so that homogeneous mixing can be easily performed and there is no anxiety for use in cold regions. , Industrially useful.
Claims (3)
下式ＩＩ：
で表されるパラフェニレンジアミン系化合物からなる化合物を少なくとも１種含む安定化されたバイオディーゼル燃料。 Formula I:
Formula II:
A stabilized biodiesel fuel comprising at least one compound comprising a paraphenylenediamine compound represented by the formula:
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| Application Number | Priority Date | Filing Date | Title |
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| JP2007227642A JP2009057510A (en) | 2007-09-03 | 2007-09-03 | Stabilized bio-diesel fuel |
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| Application Number | Priority Date | Filing Date | Title |
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| JP2007227642A JP2009057510A (en) | 2007-09-03 | 2007-09-03 | Stabilized bio-diesel fuel |
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| JP2009057510A true JP2009057510A (en) | 2009-03-19 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011105291A1 (en) | 2010-02-24 | 2011-09-01 | 独立行政法人産業技術総合研究所 | Biodiesel fuel manufacturing method and biodiesel fuel composition |
| US9650582B2 (en) | 2014-03-03 | 2017-05-16 | National Institute Of Advanced Industrial Science And Technology | Biodiesel fuel hydrogenation method |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5684794A (en) * | 1979-12-14 | 1981-07-10 | Nikki Universal Co Ltd | Antioxidant for fuel oil |
| WO2007089645A2 (en) * | 2006-01-27 | 2007-08-09 | Oryxe Energy International, Inc. | Biodiesel fuel additive |
| JP2009540100A (en) * | 2006-06-14 | 2009-11-19 | ケムチュア コーポレイション | Antioxidant additive for biodiesel |
-
2007
- 2007-09-03 JP JP2007227642A patent/JP2009057510A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5684794A (en) * | 1979-12-14 | 1981-07-10 | Nikki Universal Co Ltd | Antioxidant for fuel oil |
| WO2007089645A2 (en) * | 2006-01-27 | 2007-08-09 | Oryxe Energy International, Inc. | Biodiesel fuel additive |
| JP2009540100A (en) * | 2006-06-14 | 2009-11-19 | ケムチュア コーポレイション | Antioxidant additive for biodiesel |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011105291A1 (en) | 2010-02-24 | 2011-09-01 | 独立行政法人産業技術総合研究所 | Biodiesel fuel manufacturing method and biodiesel fuel composition |
| US9650582B2 (en) | 2014-03-03 | 2017-05-16 | National Institute Of Advanced Industrial Science And Technology | Biodiesel fuel hydrogenation method |
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