JP7494304B2 - 低硫黄ディーゼル用目詰まり抑制剤、その製造方法及び使用 - Google Patents
低硫黄ディーゼル用目詰まり抑制剤、その製造方法及び使用 Download PDFInfo
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- JP7494304B2 JP7494304B2 JP2022539658A JP2022539658A JP7494304B2 JP 7494304 B2 JP7494304 B2 JP 7494304B2 JP 2022539658 A JP2022539658 A JP 2022539658A JP 2022539658 A JP2022539658 A JP 2022539658A JP 7494304 B2 JP7494304 B2 JP 7494304B2
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- Prior art keywords
- clogging
- sulfur diesel
- low sulfur
- vegetable oil
- clogging inhibitor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011593 sulfur Substances 0.000 title claims description 66
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- 238000004519 manufacturing process Methods 0.000 title claims description 19
- 239000003795 chemical substances by application Substances 0.000 title claims description 13
- 239000003112 inhibitor Substances 0.000 claims description 80
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 73
- 239000008158 vegetable oil Substances 0.000 claims description 73
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 72
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- 238000000034 method Methods 0.000 claims description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 24
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- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical class N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 17
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
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- UFQVHWMBHIJNLT-UHFFFAOYSA-N 2-tert-butyl-4-[2-(3-tert-butyl-4-hydroxy-5-methylphenyl)ethyl]-6-methylphenol Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 UFQVHWMBHIJNLT-UHFFFAOYSA-N 0.000 description 1
- DGQFNPWGWSSTMN-UHFFFAOYSA-N 2-tert-butyl-4-[4-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1CCCCC1=CC(C(C)(C)C)=C(O)C=C1C DGQFNPWGWSSTMN-UHFFFAOYSA-N 0.000 description 1
- ZRUOCGQIPKXQMI-UHFFFAOYSA-N 2-tert-butyl-4-methyl-6-prop-2-enylphenol Chemical compound CC1=CC(CC=C)=C(O)C(C(C)(C)C)=C1 ZRUOCGQIPKXQMI-UHFFFAOYSA-N 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- YKUUUTAPMKKPTK-UHFFFAOYSA-N 2-tert-butyl-6-[2-(3-tert-butyl-2-hydroxy-5-methylphenyl)ethyl]-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(CCC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O YKUUUTAPMKKPTK-UHFFFAOYSA-N 0.000 description 1
- BVCOHOSEBKQIQD-UHFFFAOYSA-N 2-tert-butyl-6-methoxyphenol Chemical compound COC1=CC=CC(C(C)(C)C)=C1O BVCOHOSEBKQIQD-UHFFFAOYSA-N 0.000 description 1
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 1
- LYQIPMLFCQTVQK-UHFFFAOYSA-N 3,5-ditert-butyl-4-(2,6-ditert-butyl-4-hydroxyphenyl)phenol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1C1=C(C(C)(C)C)C=C(O)C=C1C(C)(C)C LYQIPMLFCQTVQK-UHFFFAOYSA-N 0.000 description 1
- BFZOTKYPSZSDEV-UHFFFAOYSA-N 4-butan-2-yl-2,6-ditert-butylphenol Chemical compound CCC(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BFZOTKYPSZSDEV-UHFFFAOYSA-N 0.000 description 1
- WTWGHNZAQVTLSQ-UHFFFAOYSA-N 4-butyl-2,6-ditert-butylphenol Chemical compound CCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WTWGHNZAQVTLSQ-UHFFFAOYSA-N 0.000 description 1
- DJRYJQNZAYJVGF-UHFFFAOYSA-N 4-methyl-2-(1-phenylethyl)phenol Chemical compound C=1C(C)=CC=C(O)C=1C(C)C1=CC=CC=C1 DJRYJQNZAYJVGF-UHFFFAOYSA-N 0.000 description 1
- MEPYMUOZRROULQ-UHFFFAOYSA-N 4-tert-butyl-2,6-dimethylphenol Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1O MEPYMUOZRROULQ-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001299 aldehydes Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- CUXYLFPMQMFGPL-FWSDQLJQSA-N alpha-Eleostearic acid Natural products CCCCC=CC=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-FWSDQLJQSA-N 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- CMCJNODIWQEOAI-UHFFFAOYSA-N bis(2-butoxyethyl)phthalate Chemical compound CCCCOCCOC(=O)C1=CC=CC=C1C(=O)OCCOCCCC CMCJNODIWQEOAI-UHFFFAOYSA-N 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- IXLCRBHDOFCYRY-UHFFFAOYSA-N dioxido(dioxo)chromium;mercury(2+) Chemical compound [Hg+2].[O-][Cr]([O-])(=O)=O IXLCRBHDOFCYRY-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229960002311 dithranol Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- JGEMYUOFGVHXKV-UPHRSURJSA-N malealdehyde Chemical compound O=C\C=C/C=O JGEMYUOFGVHXKV-UPHRSURJSA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- AFVLVVWMAFSXCK-UHFFFAOYSA-N α-cyano-4-hydroxycinnamic acid Chemical group OC(=O)C(C#N)=CC1=CC=C(O)C=C1 AFVLVVWMAFSXCK-UHFFFAOYSA-N 0.000 description 1
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- C07C59/40—Unsaturated compounds
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- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/18—Organic compounds containing oxygen
- C10L1/188—Carboxylic acids; metal salts thereof
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- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/26—Carboxylic acids; Salts thereof
- C10M129/28—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
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- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
- C10M129/92—Carboxylic acids
- C10M129/93—Carboxylic acids having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
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- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/14—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by isomerisation
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- C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
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Description
好ましくは、m=4又はm=5であり、かつm+n=12である。
異性化反応の条件下で、非共役植物油をアルカリ又はアルカリのアルコール溶液と接触させて反応させるステップ(1)と、
ステップ(1)において接触させて反応させることによって得られた生成物を酸性化して水洗し、水相を分離して、変性植物油脂肪酸を得るステップ(2)と、
ディールス-アルダー付加反応の条件下で、変性植物油脂肪酸を不飽和ジアルデヒドと接触させるステップ(3)と、
未反応の原料を除去して、植物油系目詰まり抑制剤を得るステップ(4)とを含む、ことを特徴とする植物油系目詰まり抑制剤の製造方法を提供する。
(1)コーン油(ヨウ素価125mgKOH/g、残りの性質は表1参照)1000g、エチレングリコール3500g、KOH 600gを反応器に投入して均一に混合し、160℃で撹拌しながら5h反応させ、生成物を塩酸でpH2.5に酸性化し、中性となるまで水洗し、静置して層別化すると、水相を分離して、変性コーン油脂肪酸を得た。
(1)コーン油1000g、エチレングリコール2500g、KOH 500gを反応器に投入して均一に混合し、180℃で撹拌しながら3h反応させ、生成物を塩酸でpH2に酸性化し、中性となるまで水洗した後、静置して層別化すると、水相を分離して、変性コーン油脂肪酸を得た。
(1)コーン油1000g、エチレングリコール3000g、KOH 550gを反応器に投入して均一に混合し、170℃で撹拌しながら4h反応させ、生成物を塩酸でpH3に酸性化し、中性となるまで水洗した後、静置して層別化すると、水相を分離して、変性コーン油脂肪酸を得た。
綿実油(ヨウ素価108mgKOH/g)を反応原料として用いて、目詰まり抑制剤製品を得た以外、製造プロセス及び操作条件は実施例1と同様であった。綿実油脂肪酸の転化率は45.3%、製品の酸価は122.4mgKOH/g、凝固点は-26.8℃であった。
ピーナッツ油(ヨウ素価95mgKOH/g)を反応原料として用いて、目詰まり抑制剤製品を得た以外、製造プロセス及び操作条件は実施例1と同様であった。ピーナッツ油脂肪酸の転化率は25.5%、製品の酸価は122.0mgKOH/g、凝固点は-26.8℃であった。
ブンカンカオイル(ヨウ素価116mgKOH/g)を反応原料として用いて、目詰まり抑制剤製品を得た以外、製造プロセス及び操作条件は実施例1と同様であった。ブンカンカオイル脂肪酸の転化率は39.5%、製品の酸価は122.2mgKOH/g、凝固点は-26.8℃であった。
2-ペンテンジアール50.8gを反応原料として用いて、目詰まり抑制剤製品を得た以外、製造プロセス及び操作条件は実施例1と同様であった。コーン油脂肪酸の転化率は44.2%、製品の酸価は119.6mgKOH/g、凝固点は-25.8℃であった。
3-ヘキセンジアール57.2gを反応原料として用いて、目詰まり抑制剤製品を得た以外、製造プロセス及び操作条件は実施例1と同様であった。コーン油脂肪酸の転化率は42.5%、製品の酸価は117.4mgKOH/g、凝固点は-24.3℃であった。
4-オクテンジアール70.0gを反応原料として用いて、目詰まり抑制剤製品を得た以外、製造プロセス及び操作条件は実施例1と同様であった。コーン油脂肪酸の転化率は30.5%、製品の酸価は115.7mgKOH/g、凝固点は-20.3℃であった。
エチレングリコールの代わりに1,3-プロピレングリコールを用いて、目詰まり抑制剤製品を得た以外、製造プロセス及び操作条件は実施例1と同様であった。コーン油脂肪酸の転化率は44.1%、製品の酸価は122.4mgKOH/g、凝固点は-26.3℃であった。
エチレングリコールの代わりに1,4-ブタンジオールを用いて、目詰まり抑制剤製品を得た以外、製造プロセス及び操作条件は実施例1と同様であった。コーン油脂肪酸の転化率は40.2%、製品の酸価は122.2mgKOH/g、凝固点は-26.5℃であった。
ヨウ素価49mgKOH/gのパーム油を反応原料として用いて、目詰まり抑制剤を製造した以外、製造プロセス及び操作条件は実施例1と同様であった。パーム油脂肪酸の転化率は6.4%未満であり、目詰まり抑制剤の転化率が低すぎて、経済的な利益がなかった。
植物油と不飽和ジアルデヒドを直接反応させた以外、製造プロセス及び操作条件は実施例1と同様であり、その結果、反応が起こらず、製品が合成できなかった。
共役二重結合を有する桐油を用いた以外、製造プロセス及び操作条件は実施例1と同様であり、その結果、反応系では架橋副反応が起こり、桐油脂肪酸の転化率は51.2%、製品の凝固点は-9℃であった。凝固点が高すぎて、使用の要件を満たしていない。
硫黄含有量が10ppm未満の低硫黄ディーゼル(低硫黄ディーゼル-1)及び摩耗痕径が580μmよりも大きい水素化精製ディーゼル(低硫黄ディーゼル-2)を用いて測定を行い、その具体的な性質は表2に示される。上記実施例及び比較例で製造された目詰まり抑制剤を上記低硫黄ディーゼルに添加して、製品の性能について測定を行い、測定結果を表3、表4に示す。
〔測定例2〕
本発明の製品が目詰まり抑制性能を有することを確認するために、低硫黄ディーゼル-1製品をそれぞれ1L、水20mlに加えて激しく振とうさせた後、密閉空間に保存し、実施例の製品及び比較例の製品を添加したディーゼルサンプルと、未添加のディーゼルサンプルの総汚染物(総汚染物は主にディーゼルで生じた細菌や他の排出物を含み、総汚染物の含有量が高すぎると、フィルタの目詰まりが発生する)を比較し、総汚染物の検出はGB/T 33400に準じて行われ、結果は表5に示される。
Claims (22)
- 式(I)で示される化合物。
(式中、x及びyはそれぞれ0~4の整数であり、m及びnはそれぞれ3~9の整数であり、かつ10≦m+n≦14であり、R1、R2はそれぞれH、直鎖又は分岐のC1~C6アルキル又はC3~C6のシクロアルキルから選ばれる。) - mは4又は5である、請求項1に記載の化合物。
- x及びyはそれぞれ0又は1である、請求項2に記載の化合物。
- m+n=12である、請求項2に記載の化合物。
- R1、R2はそれぞれH、メチル又はエチルから選ばれる、請求項2に記載の化合物。
- 請求項1~5のいずれか1項に記載の化合物の低硫黄ディーゼル用目詰まり抑制剤としての使用。
- 異性化反応の条件下で、非共役植物油をアルカリ又はアルカリのアルコール溶液と接触させて反応させるステップ(1)と、
接触させて反応させることによって得られた生成物を酸性化して水洗し、水相を分離して、変性植物油脂肪酸を得るステップ(2)と、
ディールス-アルダー付加反応の条件下で、変性植物油脂肪酸を不飽和ジアルデヒドと接触させるステップ(3)と、
ステップ(3)で接触させて得られた生成物から未反応の原料を除去するステップ(4)とを含み、
前記非共役植物油は、コーン油、綿実油、ピーナッツ油、胡麻油、ブンカンカオイルのうちの1種又は複数種であることを特徴とする植物油系目詰まり抑制剤の製造方法。 - ステップ(1)において、前記アルカリは水酸化カリウム及び/又は水酸化ナトリウムであり、その使用量が非共役植物油の質量の0.5~0.6倍であり、前記アルコールは飽和2価アルコールであり、その使用量が非共役植物油の質量の2.5~3.5倍である、請求項7に記載の方法。
- 前記アルコールは、エチレングリコール、1,3-プロピレングリコール、1,4-ブタンジオールのうちの少なくとも1種である、請求項8に記載の方法。
- ステップ(1)において、前記異性化反応の条件は温度180~220℃、時間3~5hを含む、請求項7又は8に記載の方法。
- ステップ(2)において、前記不飽和ジアルデヒドは、炭素数4~12のものである、請求項7又は8に記載の方法。
- 前記不飽和ジアルデヒドは、2-ブテンジアール、2-ペンテンジアール、2-ヘキセンジアール、3-ヘキセンジアール、2-ヘプテンジアール、3-ヘプテンジアール、2-オクテンジアール、3-オクテンジアール、4-オクテンジアールのうちの1種又は複数種である、請求項11に記載の方法。
- 不飽和ジアルデヒドと植物油脂肪酸とのモル比が0.5:1~3:1である、請求項11に記載の方法。
- 不飽和ジアルデヒドと植物油脂肪酸とのモル比が0.8:1~2:1である、請求項13に記載の方法。
- ステップ(2)において、前記ディールス-アルダー付加反応の条件は、温度190~210℃、時間0.5~2hを含む、請求項7又は8に記載の方法。
- ステップ(4)において、前記未反応の原料の除去は、接触させて得られた混合物を圧力30~150Pa、温度180~220℃で減圧蒸留することを含む、請求項7又は8に記載の方法。
- 請求項1~5のいずれか1項に記載の化合物を含有する低硫黄ディーゼル用目詰まり抑制剤組成物。
- 低硫黄ディーゼル用目詰まり抑制剤組成物の全量を基準に、前記化合物70~90重量%と、酸化防止剤0.2~2重量%と、芳香族炭化水素ソルベントオイル8~29重量%とを含む、請求項17に記載の低硫黄ディーゼル用目詰まり抑制剤組成物。
- 低硫黄ディーゼルと目詰まり抑制剤とを含有する目詰まり抑制性を向上させた低硫黄ディーゼルであって、
前記目詰まり抑制剤は請求項1~5のいずれか1項に記載の化合物、又は、請求項17又は18に記載の低硫黄ディーゼル用目詰まり抑制剤組成物である、ことを特徴とする低硫黄ディーゼル。 - 前記目詰まり抑制剤は、請求項1~5のいずれか1項に記載の化合物であり、低硫黄ディーゼル基油100重量部に対して、前記目詰まり抑制剤の含有量は0.008~0.01重量部であるか、又は、
前記目詰まり抑制剤は、請求項17又は18に記載の低硫黄ディーゼル用目詰まり抑制剤組成物であり、低硫黄ディーゼル基油100重量部に対して、前記化合物換算で、低硫黄ディーゼル用目詰まり抑制剤組成物の含有量は0.008~0.01重量部である、請求項19に記載の低硫黄ディーゼル。 - 目詰まり抑制剤を低硫黄ディーゼルに添加することを含む、ことを特徴とする低硫黄ディーゼル目詰まり抑制性の向上方法であって、
前記目詰まり抑制剤は、請求項1~5のいずれか1項に記載の化合物、又は、請求項17又は18に記載の低硫黄ディーゼル用目詰まり抑制剤である、低硫黄ディーゼル目詰まり抑制性の向上方法。 - 前記目詰まり抑制剤は、請求項1~5のいずれか1項に記載の化合物であり、低硫黄ディーゼル基油100重量部に対して、前記目詰まり抑制剤の含有量は0.008~0.01重量部であるか、又は、
前記目詰まり抑制剤は、請求項17又は18に記載の低硫黄ディーゼル用目詰まり抑制剤組成物であり、低硫黄ディーゼル100重量部に対して、前記化合物換算で、低硫黄ディーゼル用目詰まり抑制剤組成物の含有量は0.008~0.01重量部である、請求項21に記載の方法。
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