CN1092703C - 聚烷基苯氧基烷醇的芳族酯和含有它们的燃料组合物 - Google Patents
聚烷基苯氧基烷醇的芳族酯和含有它们的燃料组合物 Download PDFInfo
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- CN1092703C CN1092703C CN97190529A CN97190529A CN1092703C CN 1092703 C CN1092703 C CN 1092703C CN 97190529 A CN97190529 A CN 97190529A CN 97190529 A CN97190529 A CN 97190529A CN 1092703 C CN1092703 C CN 1092703C
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- fuel
- hydrogen
- alkyl
- poly
- compound
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- 239000000446 fuel Substances 0.000 title claims abstract description 79
- 239000000203 mixture Substances 0.000 title claims description 49
- 125000003118 aryl group Chemical group 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 239000001257 hydrogen Substances 0.000 claims abstract description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 28
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- -1 polypropylene Polymers 0.000 claims description 107
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 33
- 229920002367 Polyisobutene Polymers 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 24
- 150000002430 hydrocarbons Chemical class 0.000 claims description 19
- 229930195733 hydrocarbon Natural products 0.000 claims description 17
- 150000001721 carbon Chemical group 0.000 claims description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- 239000012530 fluid Substances 0.000 claims description 12
- 238000009835 boiling Methods 0.000 claims description 9
- 239000003502 gasoline Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000004743 Polypropylene Substances 0.000 claims description 6
- 229920001155 polypropylene Polymers 0.000 claims description 6
- 239000013049 sediment Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 12
- 239000002816 fuel additive Substances 0.000 abstract description 4
- 230000002265 prevention Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 34
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 29
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- 239000002585 base Substances 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 229960003742 phenol Drugs 0.000 description 18
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 239000000654 additive Substances 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 230000000996 additive effect Effects 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000012442 inert solvent Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
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- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 8
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
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- 239000003795 chemical substances by application Substances 0.000 description 7
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 7
- 238000005984 hydrogenation reaction Methods 0.000 description 7
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229910000105 potassium hydride Inorganic materials 0.000 description 4
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 230000033228 biological regulation Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000011010 flushing procedure Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 3
- 229940035429 isobutyl alcohol Drugs 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920013639 polyalphaolefin Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000004904 shortening Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- GYLKKXHEIIFTJH-UHFFFAOYSA-N 3-cyanobenzoic acid Chemical compound OC(=O)C1=CC=CC(C#N)=C1 GYLKKXHEIIFTJH-UHFFFAOYSA-N 0.000 description 2
- XLDLRRGZWIEEHT-UHFFFAOYSA-N 3-hydroxy-4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C(O)=C1 XLDLRRGZWIEEHT-UHFFFAOYSA-N 0.000 description 2
- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- ADCUEPOHPCPMCE-UHFFFAOYSA-N 4-cyanobenzoic acid Chemical compound OC(=O)C1=CC=C(C#N)C=C1 ADCUEPOHPCPMCE-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 2
- 150000005339 4-nitrobenzoic acids Chemical class 0.000 description 2
- QRYSWXFQLFLJTC-UHFFFAOYSA-N 616-82-0 Chemical compound OC(=O)C1=CC=C(O)C([N+]([O-])=O)=C1 QRYSWXFQLFLJTC-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07C229/60—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in meta- or para- positions
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Abstract
有下式的聚烷基苯氧基烷醇的芳族酯或其燃料可溶性盐：式中，R为羟基、硝基或-(CH2)x-NR5R6，其中R5和R6各自独立为氢或有1-6个碳原子的低碳烷基，X为0或1；R1为氢、羟基、硝基或-NR7R8，其中R7和R8各自独立为氢或有1-6个碳原子的低碳烷基；R2和R3各自独立为氢或有1-6个碳原子的低碳烷基；以及R4为平均分子量为约450至5000的聚烷基。式I的化合物适用作防止和控制发动机的沉积物的燃料添加剂。
Description
本发明涉及聚烷基苯氧基烷醇的芳族酯及其衍生物。另一方面，本发明涉及这些化合物在燃料组合物中的应用，以防止和控制发动机的沉积物。
大家都知道，由于烃类燃料的氧化和聚合，汽车发动机倾向在发动机部件如汽化器口、节流体、燃料喷射器、进气口和进气阀的表面上形成沉积物。这些沉积物，甚至在相当少量存在时也常常引起显著的驾驶性能问题，如失速和加速性差。而且，发动机的沉积物可明显增加汽车燃料的消耗量和废气污染物的生成量。所以，开发对防止或控制这样的沉积物有效的燃料清净剂或“沉积物控制”添加剂具有很重要的意义，在本专业中已经知道许多这样的添加剂。
例如，脂族烃类取代的酚类当用于燃料组合物中时，已知用它来减少发动机的沉积物。1974年11月19日颁发给Kreuz等的US 3,849,085公开了一种含有约0.01至0.25％(体积)高分子量脂族烃类取代的酚的汽油沸程烃类混合物的发动机燃料组合物，取代酚中脂族烃基的平均分子量为约500至3500。该专利指出，含有少量脂族烃类取代的酚的汽油组合物不仅能防止或抑制汽油发动机的进气阀和进气口沉积物的生成，而且还能提高在用于高操作温度下操作的发动机中燃料组合物的性能，在发动机的集气岐管中分解和沉积物生成量减少。
同样，1979年1月16日颁发给Machleder等的US4,134 846公开了一种含有以下混合物的燃料添加剂组合物：(1)脂族烃类取代的酚、表氯醇和伯或仲单胺或多胺的反应产物和(2)聚亚烷基酚的混合物。该专利指出，这样的组合物有极好的汽化器、感应系统和燃烧室的清净作用，此外当以低浓度用于烃类燃料时还有有效的生锈抑制作用。
氨基酚类当用于燃料组合物时，也已知用作清净/分散剂、抗氧化剂和防腐蚀剂。例如，1982年3月16日颁发给R.M.Lange的US 4320021公开了有至少一个至少有30个碳原子的基本上饱和的烃类取代基的氨基酚类。该专利的氨基酚为油基润滑剂和通常的液体燃料提供了有用的和希望的性质。
同样，1964年9月22日颁发给K.Ley等的US 3149933公开了烃类取代的氨基酚类用作液体燃料的稳定剂。
1983年6月7日颁发给R.M.Lange的US 4386939公开了通过氨基酚与至少一个3-或4-元环杂环化合物反应制备的含氮的组合物；杂环化合物中，杂原子是单个氧、硫或氮原子，如环氧乙烷。该专利的含氮的组合物用作润滑剂和燃料的添加剂。
硝基酚类也用作燃料添加剂。例如，1982年8月31日颁发给K.E.Davis的US 4347148公开了含有至少一种有至少约40个碳原子的脂族取代基的硝基酚类。该专利的硝基酚用作润滑油和燃料组合物的清净剂、分散剂、抗氧化剂和破乳化剂。
同样，1969年3月25日颁发给M.Dubeck等的U.S.3434814公开了含主要量汽油沸程的液体烃和足以减少废气排放量和发动机沉积物的少量有烷基、芳基、芳烷基、烷酰氧基、烷氧基、羟基或卤素取代基的芳族硝基化合物的液体烃燃料组合物。
最近，已表明当某些聚(氧亚烷基)酯用于燃料组合物时，可减少发动机的沉积物。例如，1993年5月18日颁发给R.L.Sung等的US5211721公开了一种聚醚多元醇与式RCOOH表示的酸(其中，R为有6-27个碳原子的烃基)的反应产物的油溶性聚醚添加剂。该专利的聚(氧亚烷基)酯化合物当在发动机燃料组合物用作可溶性添加剂时，适用于抑制含碳质沉积物的生成、抑制发动机燃料浑浊以及用作ORI抑制剂。
氨基-和硝基苯甲酸的聚(氧亚烷基)酯在本专业中也是已知的。例如，1955年8月2日颁发给M.Matter的US 2714607公开了氨基苯甲酸、硝基苯甲酸和其他等节环状酸的聚乙氧基酯。这些聚乙氧基酯有极好的药理学性质，适用作麻醉剂、解痉剂、兴奋剂和抑菌剂。
同样，1992年2月25日颁发给D.T.Reardan等的US 5090914公开了在芳族部分有氨基或肼基羰基取代基以及在芳族部分和聚(氧亚烷基)部分之间有酯、酰胺、氨基甲酸酯、脲或醚键联基团的聚(氧亚烷基)芳族化合物。这些化合物适用于改性大分子物种，如蛋白质和酶。
1980年9月22日颁发给R.C.Baron的US4328322公开了低聚多元醇如聚(亚乙基)二醇的氨基-和硝基苯甲酸酯。这些材料通过与多异氰酸酯反应来生产合成的聚合物。
1989年8月22日颁发给Franz等的US 4859210公开了含有以下组分的燃料组合物：(1)一种或多种聚丁基醇或聚异丁基醇，其中聚丁基或聚异丁基的数均分子量为324-3000，或(2)聚丁基醇或聚异丁基醇的聚(烷氧基化物)，或(3)聚丁基醇或聚异丁基醇的羧酸酯。该专利还公开，当燃料组合物含有聚丁基醇或聚异丁基醇的酯时，成酯的酸基可由饱和的或不饱和的、脂族的或芳族的，无环的或环状的一元或多元羧酸得到。
1966年11月15日和1967年7月11日分别颁发给Dexter等的US3285855和3330859公开了二烷基羟基苯甲酸和羟基苯基烷酸的烷基酯，其中酯部分含有6-30个碳原子。这些专利指出，这样的酯适用于使聚丙烯和其他有机材料稳定，通常能经受住氧化变质。在US 5196565公开了含有受阻的二烷基羟基苯基的类似烷基酯，该专利于1993年3月23日颁发给Ross。
1993年3月23日颁发给Mollet等的US 5196142公开了羟基苯基羧酸的烷基酯，其中酯部分含有至多23个碳原子。该专利指出，这样的化合物用作使乳液聚合的聚合物稳定的抗氧化剂。
1995年4月18日颁发的共同转让的US5407452和1995年2月9日公布的对应的国际专利申请书WO 95/04118公开了某些有5-100个氧亚烷基单元的聚(氧亚烷基)硝基和氨基芳族酯，并指出这样的化合物用作燃料添加剂，来防止和控制发动机的沉积物。
同样，1995年6月27日颁发给我的US 5427591和1994年7月7日公布的对应的国际专利申请书WO 94/14926公开了某些聚(氧亚烷基)羟基芳族酯，它们用作燃料添加剂，以控制发动机的沉积物。
此外，1995年1月10日颁发给我的US 5380345和1995年6月8日公布的对应国际专利申请书WO 95/15366公开了某些用作燃料的沉积物控制添加剂的聚烷基硝基-和氨基芳族酯。而且，1995年5月4日公布的共同转让的国际专利申请书WO95/11955公开了某些聚烷基羟基芳族酯，它们也用作燃料沉积物控制添加剂。
现已发现，某些聚烷基苯氧基烷醇的芳族酯当用作燃料组合物中的燃料添加剂时，可对发动机的沉积物，特别是对进气阀的沉积物提供极好的控制。
本发明的化合物包括有以下化学式的那些化合物及其燃料可溶性盐：式中，R为羟基、硝基或-(CH2)X-NR5R6，其中R5和R6各自独立为氢或有1-6个碳原子的低碳烷基和X为0或1；
R1为氢、羟基、硝基或-NR7R8，其中R7和R8各自独立为氢或有1-6个碳原子的低碳烷基；
R2和R3各自独立为氢或有1-6个碳原子的烷基；
R4为平均分子量约450至5000的聚烷基；
本发明还提供一种燃料组合物，它含有主要量的在汽油或柴油沸程范围的烃类以及控制沉积物的有效量的本发明的化合物。
本发明还提供一种燃料浓缩物，它含有沸程为约150至400°F的惰性稳定的亲油性有机溶剂以及约10至70％(重量)本发明的化合物。
在众多因素中，本发明基于这一惊人的发现：聚烷基苯氧基烷醇的某些芳族酯当在燃料组合物中用作添加剂时，可对发动机的沉积物，特别是对进气阀上的沉积物有极好的控制作用。
在性能(如沉积物控制)、贮运性质以及性能/价格有效性的基础上，本发明优选的化合物为这些化合物，其中R为硝基、氨基、N-烷基氨基或-CH2NH2(氨甲基)。更优选的是，R为硝基、氨基或-CH2NH2基。最优选的是，R为氨基或-CH2NH2基，特别是氨基。优选的是，R1为氢、羟基、硝基或氨基。更优选的是，R1为氢或羟基。最优选的是，R1为氢。优选的是，R4为平均分子量为约500至3000的聚烷基、更优选约700至3000、最优选约900至2500。优选的是，该化合物有优选取代基的组合体。
优选的是，R2和R3中的一个为氢或有1-4个碳原子的低碳烷基，而另一个为氢。更优选的是，R2和R3中的一个为氢、甲基或乙基，而另一个为氢。最优选的是，R2为氢、甲基或乙基，而R3为氢。
当R和/或R1为N-烷基氨基时，N-烷基氨基部分中的烷基优选含有1-4个碳原子。更优选的是，N-烷基氨基为N-甲基氨基或N-乙基氨基。
同样，当R和/或R1为N，N-二烷基氨基时，N，N-二烷基氨基部分中的每一烷基优选含有1-4个碳原子。更优选的是，每一烷基为甲基或乙基。例如，特别优选的N，N-二烷基氨基为N，N-二甲基氨基、N-乙基-N-甲基氨基和N，N-二乙基氨基。
另一类优选的化合物是这些化合物，其中R为氨基、硝基或-CH2NH2，而R1为氢或羟基。特别优选的一类化合物是这些化合物，其中R为氨基，R1、R2和R3为氢，R4为由聚异丁烯得到的聚烷基。
优选的是，R取代基处于苯甲酸部分的间位或更优选处于对位，即相对于羰氧基的对位或间位。当R1为不同于氢的取代基时，特别优选这一R1基相对于羰氧基的间位或对位以及相对于R取代基的邻位。此外，通常当R1不是氢时，优选R或R1中的一个处于相对于羰氧基的对位，而另一个处于羰氧基的间位。同样，优选在另一苯环上的R4取代基处于醚键联基团的对位或间位、更优选对位。
用于本发明的化合物通常有足够的分子量，以致在正常的发动机进气阀操作温度(约200至250℃)下不挥发。通常，用于本发明的化合物的分子量为约700至约3500、优选约700至约2500。
对于含有氨基或取代氨基的化合物来说，可很容易制备式I化合物的燃料可溶性盐，这样的盐旨在用于防止或控制发动机的沉积物。例如适合的盐包括通过氨基部分用强有机酸如烷基磺酸或芳基磺酸质子化制得的盐。优选的盐由甲苯磺酸和甲烷磺酸得到。
当R或R1取代基为羟基时，适合的盐可通过用碱去质子化羟基制得。这样的盐包括碱金属盐、碱土金属盐、铵盐和取代的铵盐。羟基取代的化合物的优选盐包括碱金属盐、碱土金属盐和取代的铵盐。
如这里使用的，除非另加说明，以下的术语有以下的含义。
术语“氨基”指基团：-NH2。
术语“N-烷基氨基”指基团：-NHRa，其中Ra为烷基。术语“N，N-二烷基氨基”指基团：-NRbRc，其中Rb和Rc为烷基。
术语“烷基”指直链的和支链的烷基。
术语“低碳烷基”指有1至约6个碳原子的烷基，包括伯、仲和叔烷基。典型的低碳烷基包括如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、正戊基、正己基等。
术语“聚烷基”指通常由聚烯烃得到的烷基，聚烯烃是单烯烃、特别是1-单-烯烃如乙烯、丙烯、丁烯等的聚合物或共聚物。优选的是，所用的单烯烃有2至约24个碳原子、更优选约3至12个碳原子。更优选的单烯烃包括丙烯、丁烯(特别是异丁烯)、1-辛烯和1-癸烯。由这样的单烯烃制得的聚烯烃包括聚丙烯、聚丁烯(特别是聚异丁烯)以及由1-辛烯和1-癸烯得到的聚α-烯烃。
术语“燃料”或“烃类燃料”指通常沸程在汽油和柴油燃料范围的液体烃类。
本发明的聚烷基苯氧基烷基芳族酯可用以下一般的方法和步骤来制备。应当理解，这里给出了典型的或优选的工艺条件(如反应温度、时间、反应物摩尔比、溶剂、压力等)，其他工艺条件也可使用，除非另加说明。优化的反应条件可随所用的特定的反应物或溶剂变化，但这样的条件可由熟悉本专业的技术人员通过常规的优化步骤来确定。
熟悉本发明的技术人员还应考虑到在进行以下合成步骤时屏蔽或保护某些官能基团可能是必要的。在这样的情况下，保护基团用来保护官能基团不受不希望的反应或者屏蔽它与其他官能团或与用于进行所需化学转变的试剂的不希望的反应。对于特定官能基团，保护基团的适当选择对于熟悉本专业的技术人员是很容易的。例如在T.W.Greene和P.G.M.Wuts，Protective Groups in Organic Synthesis，SecondEdition，Wiley，New York，1991以及所引的文献中描述了各种保护基团及其引入和脱除。
在本合成步骤中，当必要时，羟基优选被保护，作为苄基或叔丁基二甲基甲硅烷基醚。这些保护基团的引入和除去在本专业中已很好地描述。氨基也可能需要保护，这可通过使用标准的氨基保护基团如苄氧基羰基或三氟乙酰基来实现。此外，正如将在下文中更详细讨论的，在本发明中使用的，在芳族部分上有氨基的芳族酯通常由相应的硝基衍生物来制备。因此，在许多以下步骤中，硝基将作为氨基部分的保护基团。
而且，在芳族部分有-CH2NH2基团的本发明的化合物通常由相应的氰基衍生物来制备。因此，在许多以下的步骤中，氰基将作为-CH2NH2部分的保护基团。
本发明的聚烷基苯基烷基芳族酯可用这样一种方法来制备，该法首先包括在催化数量的碱金属氢化物或氢氧化物或碱金属盐存在下下式的聚烷基酚：
式中，R4如这里规定的，与下式的碳酸亚烷基酯羟烷基化：
式中，R2和R3如这里规定的，羟烷基化反应在催化数量的碱金属氢化物或氢氧化物或碱金属盐存在下进行，得到下式的聚烷基苯氧基烷醇：
式中，R2、R3和R4如这里规定的。
式II的聚烷基酚类是大家熟悉的材料，通常由酚与所需的聚烯烃或氯化聚烯烃的烷基化来制备。聚烷基酚类进一步的讨论例如可在US4744921和US 5300701中找到。
因此，式II的聚烷基酚类可用常规的步骤由相应的烯烃来制备。例如，上述式II的聚烷基酚类可在以下条件下通过适当的烯烃或烯烃混合物与酚反应来制备：在烷基化催化剂存在下，在约25至150℃、优选30至100℃下，在纯粹的反应物或基本上惰性的溶剂中，在常压下。优选的烷基化催化剂是三氟化硼。可使用等摩尔比反应物。另一方面，也可使用摩尔过量的酚，即每当量烯烃有2-3当量酚，未反应的酚再进行循环。后一方法使单烷基酚最多。惰性溶剂的例子包括庚烷、苯、甲苯、氯苯和250稀释剂，它是芳烃、烷烃和环烷烃的混合物。
用于本发明的聚烷基酚类上的聚烷基取代基通常由这样的聚烯烃得到，所述聚烯烃是单烯烃、特别是1-单-烯烃如乙烯、丙烯、丁烯等的聚合物或共聚物。优选的是，所用的单烯烃有2至约24个碳原子、更优选约3至12个碳原子。更优选的单烯烃包括丙烯、丁烯(特别是异丁烯)、1-辛烯和1-癸烯。由这样的单烯烃制得的聚烯烃包括聚丙烯、聚丁烯(特别是聚异丁烯)以及由1-辛烯和1-癸烯生成的聚α-烯烃。
用于制备现在使用的聚烷基酚类的优选的聚异丁烯是含有至少约20％更有反应性的甲基亚乙烯基异构体、优选至少50％、更优选至少70％更有反应性的甲基亚乙烯基的聚异丁烯。适合的聚异丁烯包括用BF3催化剂制备的那些聚异丁烯。甲基亚乙烯基异构体占总组合物中高百分数的聚异丁烯的制备在US4152499和4605808中公开。这样的聚异丁烯称为“反应性的”聚异丁烯，它生成高分子量醇类，其中羟基在烃链的末端或接近烃链的末端。适合的有高烷基亚乙烯基含量的聚异丁烯的例子包括Ultravis 30，一种数均分子量为约1300和甲基亚乙烯基含量为约74％的聚异丁烯；以及Ultravis 10，一种数均分子量为约950和甲基亚乙烯基含量为约76％的聚异丁烯，两者都由British石油公司提供。
式III的碳酸亚烷基酯是已知的化合物，它们可商购或可很容易用常规的方法制备。适合的碳酸亚烷基酯包括碳酸亚乙基酯、碳酸亚丙基酯、碳酸1，2-亚丁基酯、碳酸2，3-亚丁基酯等。优选的碳酸亚烷基酯是碳酸亚乙基酯。
用于聚烷基酚与碳酸亚烷基酯反应的催化剂可为任何一种大家熟悉的羟烷基化催化剂。代表性的羟烷基化催化剂包括碱金属氢化物，如氢化锂、氢化钠和氢化钾；碱金属氢氧化物，如氢氧化钠和氢氧化钾；以及碱金属盐，如碱金属卤化物和氯化钠和氯化钾，和碱金属碳酸盐如碳酸钠和碳酸钾。所用的催化剂的数量通常为约0.01至1.0当量、优选约0.05至0.3当量。
聚烷基酚和碳酸亚烷基酯通常在以下条件下，在基本上等当量下反应：在羟烷基化催化剂存在下，在约100至210℃、优选约150至约170℃下。反应在有惰性溶剂存在下或在无惰性溶剂存在下进行。
反应时间随特定的烷基酚和碳酸亚烷基酯反应物、所用的催化剂和反应温度变化。通常，反应时间为约2至约5小时。反应进程通常用二氧化碳的释放来监测。在反应完成时，用常规的技术分离聚烷基苯氧基烷醇产物。
酚类与碳酸亚烷基酯的羟烷基化反应在本专业中是大家熟悉的，例如在US 2987555、2967892、3283030和4341905中公开。
另一方面，式IV的聚烷基苯氧基烷醇产物可在上述的羟烷基化催化剂存在下，通过式II的聚烷基酚与下式的烯化氧反应来制备：
式中，R2和R3如这里规定的。适合的式V烯化氧包括环氧乙烷、环氧丙烷、1，2-环氧丁烷、2，3-环氧丁烷等。优选的烯化氧为环氧乙烷。
在一类似于与碳酸亚烷基酯反应的方法中，聚烷基酚和烯化氧在以下条件下反应：在基本上等当量或等摩尔量中，在0.01-1.0当量羟烷基化催化剂如氢化钠或氢化钾存在下，在约30至约150℃下反应约2至约24小时。反应可在基本上无水的惰性溶剂存在下或在无溶剂存在下进行。适合的溶剂包括甲苯、二甲苯等。通常，反应在足以使反应物和任何溶剂存在的压力下进行，通常在常压或较高压力下进行。当反应完成时，用传统的步骤分离聚烷基苯氧基烷醇。
式IV的聚烷基苯氧基烷醇随后与式VI的取代的苯甲酸反应，生成式I的芳族酯化合物。这一反应可表示如下：
式中，R、R1、R2、R3和R4如这里规定的，其中在式VI的取代的苯甲酸上的任何羟基或氨基取代基优选用适合的保护基如分别为苄基或硝基保护起来。而且，芳环上的-CH2NH2取代基优选用氰基CN保护起来。
这一反应通过在以下条件下，由式IV的聚烷基苯氧基烷醇与约0.25至约1.5摩尔当量的式VI的相应取代的和被护的苯甲酸接触来进行：在酸性催化剂存在下，在约70至约160℃下接触约0.5至约48小时。这一反应适合的酸催化剂包括对甲苯磺酸、甲烷磺酸等。任选的是，反应在惰性溶剂如苯、甲苯等存在下进行。在反应进程中，该反应生成的水优选用共沸蒸馏法除去。
式VI的取代的苯甲酸通常是已知的化合物，并可用常规的方法或其明显的变通方法由已知化合物来制备。适合用作原料的代表性酸如包括2-氨基苯甲酸(邻氨基苯甲酸)、3-氨基苯甲酸、4-氨基苯甲酸、3-氨基-4-羟基苯甲酸、4-氨基-3-羟基苯甲酸、2-硝基苯甲酸、3-硝基苯甲酸、4-硝基苯甲酸、3-羟基-4-硝基苯甲酸、4-羟基-3-硝基苯甲酸。当R取代基为-CH2-NR5R6时，适合的原料包括4-氰基苯甲酸和3-氰基苯甲酸。
优选的取代的苯甲酸包括3-硝基苯甲酸、4-硝基苯甲酸、3-羟基-4-硝基苯甲酸、4-羟基-3-硝基苯甲酸、3-氰基苯甲酸和4-氰基苯甲酸。
式I的化合物或其适合的被护类似物也可通过式IV的聚烷基苯氧基烷醇与式VI的取代的苯甲酸的酰卤如酰氯或酰溴反应来制备。这可用以下的反应方程式来表示：
式中，X为卤化物，通常为氯化物或溴化物，R、R1、R2、R3和R4如这里规定的，其中式VII的酰卤上的任何羟基或氨基取代基优选分别用适合的保护基团如苄基或硝基保护起来。此外，当R为-CH2NR5R6时，适合的原料为氰基苯甲酰卤。
通常，这一反应在以下条件下通过式IV的聚烷基苯氧基烷醇与约0.9至约1.5摩尔当量的式VII的酰卤接触来进行：在惰性溶剂如甲苯、二氯甲烷、乙醚等中，在约25至约150℃下。反应通常在约0.5至约48小时内完成。优选的是，反应在足够数量的能中和反应过程中产生的酸的胺如三乙胺、二(异丙基)乙胺、吡啶或4-二甲基氨基吡啶存在下进行。
当式VI的苯甲酸或式VII的酰卤含有羟基时，可用大家熟悉的方法进行芳族羟基的保护。对于熟悉本专业的技术人员来说，对特定羟基苯甲酸适合的保护基的选择是很容易的。各种保护基及其引入和除去例如在以下文献中描述：T.W.Greene和P.G.M.Wuts，Protective Groupsin Organic Synthesis，Second Edition，Wiley，New York，1991，以及所引的文献。
酯化反应完成后，也可用常规的方法进行芳族羟基的去保护。这一去保护步骤的适宜条件与合成中所用的保护基有关，这对于熟悉本专业的技术人员来说是很显然的。例如，苄基保护基可通过在催化剂如钯/炭存在下，在1至约4大气压氢压下氢解来除去。通常，这一去保护反应在惰性溶剂、优选乙酸乙酯和乙酸的混合物中，在约0至40℃下进行约1至约24小时。
当式VI的苯甲酸或式VII的酰卤有游离的氨基(-NH2)在苯基部分上时，通常希望用上述的合成步骤首先制备相应的硝基化合物(即R和/或R1为硝基的场合)，包括酰卤的制备；然后用常规方法将硝基还原成氨基。芳族硝基可用本专业熟悉的许多种方法还原成氨基。例如，芳族硝基可在催化加氢条件下还原；或使用还原金属如锌、锡、铁等，在酸如稀盐酸存在下还原。通常，硝基用催化加氢法还原是优选的。通常，这一反应使用约1至4大气压氢压，铂或钯催化剂如钯/炭来进行。反应通常在约0至约100℃下，在惰性溶剂如乙醇、乙酸乙酯等中进行约1至24小时。芳族硝基的加氢在以下文献中更详细地讨论：如P.N.Rylander，Catalytic Hydrogenation in Organic Synthesis，pp.113-137，Academic Press(1979)；and Organic Synthesis，Collective Vol.I，Second Edition，pp.240-241，John Wiley&Sons，Inc.(1941)；以及所引的文献。
同样，当式VI的苯甲酸或式VII的酰卤在苯基部分上含有-CH2NH2时，通常希望首先制备相应的氰基化合物(即R和/或R1为-CN基的场合)，然后用常规方法将氰基还原成-CH2NH2。芳族氰基可用本专业熟悉的方法还原成-CH2NH2基。例如，芳族氰基可在类似上述还原芳族硝基成氨基的催化加氢条件下还原。因此，这一反应通常在约1至4大气压氢压下和用铂或钯催化剂如钯/炭来进行。另一适合的催化剂是Lindlar催化剂，它为钯/碳酸钙。加氢可在约0至约100℃下，在惰性溶剂如乙醇、乙酸乙酯等中进行约1至约24小时。芳族氰基的加氢在上面所引的参考文献有关芳族硝基还原中进一步讨论。
式VII的酰卤可通过式VI的相应的苯甲酸化合物与无机酰卤如亚硫酰氯、三氯化磷、三溴化磷或五氯化磷或与草酰氯接触来制备。通常，这一反应使用约1至5摩尔当量无机酰卤或草酰氯，在纯粹的反应物或在惰性溶剂如乙醚中，在约20至约80℃下进行约1至约48小时。催化剂如N，N-二甲基甲酰胺也可用于这一反应。也优选在将苯甲酸转化成酰卤以前先保护任何羟基或氨基取代基。
本发明的化合物适合在烃类燃料中用作添加剂，以防止和控制发动机的沉积物，特别是进气阀的沉积物。为达到所希望的沉积物控制所需的添加剂的适合浓度随所用燃料的类型、发动机的类型以及其他燃料添加剂的存在变化。
通常，本发明的化合物在烃类燃料中的浓度在约50至约2500ppm范围内变化、优选75至1000ppm。当有其他沉积物控制添加剂存在时，可使用较少量的本发明添加剂。
本发明的化合物可用沸程为约150至400°F(约65至205℃)的惰性稳定的亲油(即溶于汽油中)有机溶剂配制为浓缩物。优选的是，使用脂族或芳族烃类溶剂，如苯、甲苯、二甲苯或更高沸点的芳烃或芳烃稀释剂。含有约3至8个碳原子的脂族醇如异丙醇、异丁基甲醇、正丁醇等与烃类溶剂的组合也适用于本发明。在浓缩物中，添加剂的数量通常为约10至约70％(重量)、优选10至50％(重量)、更优选20至40％(重量)。
在汽油燃料中，其他燃料添加剂可与本发明的添加剂组合物一起使用，例如包括含氧化合物如甲基叔丁基醚，抗爆剂如甲基环戊二烯基三羰基锰，以及其他分散剂/清净剂如烃基胺烃基聚(氧亚烷基)胺、氨基氨基甲酸烃基聚(氧亚烷基)酯或琥珀酰亚胺。另外，也可有抗氧化剂、金属钝化剂、破乳剂。
在柴油燃料中，也可使用大家熟悉的其他添加剂，如倾点下降剂、流动改进剂、十六烷值改进剂等。
燃料可溶性不挥发的载体流体或油也可与本发明的芳族酯一起使用。该载体流体是化学上惰性的烃类可溶性液体媒液，它显著增加不挥发性残留物(NVR)，即燃料添加剂组合物的不含溶剂的液体部分，而不显著使辛烷值要求增加。载体流体可为天然流体或合成流体，如矿物油；精制的石油油品；合成聚烷烃和聚烯烃，包括氢化的和未氢化的聚α-烯烃；以及合成的聚氧亚烷基衍生的油，如Lewis的US 4191537中公开的；以及聚酯，如US 3756793(Robinson)和5004478(Vogel等)以及1990年3月7日公布的欧洲专利申请书356726和1990年8月16日公布的欧洲专利申请书382159中公开的。
据认为，这些载体流体为本发明的燃料添加剂的载体，并有助于除去和抑制沉积物。载体流体当与本发明的聚烷基芳族酯一起使用时，还显示出协合的沉积物控制性质。
通常使用的载体流体的数量为烃类燃料重的约100至约5000ppm、优选400至3000ppm。优选的是，载体流体与沉积物控制添加剂的比为约0.5∶1至约10∶1、更优选1∶1至4∶1，最优选约2∶1。
当用于燃料浓缩物时，载体流体通常的用量为约20至约60％(重量)、优选30至50％(重量)。
可用以下的非限制性实施例进一步说明本发明。除非另加说明，其中所有的温度和温度范围指摄氏度，术语“环境温度”或“室温”指约20至25℃。术语“百分数”或“％”指重量百分数，术语“摩尔”指克摩尔。术语“当量”指这样的反应试剂的量，按摩尔计它等于上述的或随后实施例所引根据一定摩尔或一定重量或体积的反应物的摩尔。这里给出的质子磁共振谱(p.m.r或n.m.r.)在300毫赫下测定，信号定为单谱线(S)、宽单谱线(bs)、双谱线(d)、双双谱线(dd)、三谱线(t)、双三谱线(dt)、四谱线(q)和多谱线(m)，而cps为周/秒。
实施例1
聚异丁基酚的制备
将203.2克酚加到装有磁搅拌器、回流冷凝器、温度计、加料漏斗和氮气进口的烧瓶中。将酚加热到40℃，然后除去加热源。然后滴加入73.5毫升三氟化硼乙醚化物。将1040克Ultravis10聚异丁烯(分子量950，76％甲基亚乙烯基，由British石油公司提供)溶于1863毫升己烷中。将聚异丁烯以这样的速度加到反应中，使温度维持在22至27℃之间。将反应混合物在室温下搅拌16小时。然后，加入400毫升浓氢氧化铵，随后加入2000毫升己烷。用水洗涤反应混合物(3×2000毫升)，在硫酸镁上干燥，过滤和在真空下除去溶剂，得到1056.5克粗反应产物。用质子NMR和硅胶色谱(用己烷再用己烷∶乙酸乙酯∶乙醇(93∶5∶2)冲洗)测定粗反应产物含有80％所需的产物。
实施例2
下式化合物的制备
将1.1克35％(重量)氢化钾于矿物油中的分散液和4-聚异丁基酚(99.7克，实施例1制备的)加到装有磁搅拌器、回流冷凝器、氮气进口和温度计的烧瓶中。在130℃下加热反应1小时，然后冷却到100℃。加入碳酸亚乙基酯(8.6克)，并将混合物在160℃下加热16小时。将反应物料冷至室温，并加入1毫升异丙醇。用1升己烷稀释反应物料，用水洗涤3次，用盐水洗涤1次。有机层在无水硫酸镁上干燥，过滤，并在真空下除去溶剂，得到98.0克所需的黄色油状产物。
实施例3
下式化合物的制备
将15.1克35％(重量)氢化钾于矿物油中的分散液和4-聚异丁基酚(1378.5克，实施例1制备的)加到装有磁搅拌器、回流冷凝器、氮气进口和温度计的烧瓶中。在130℃下加热反应1小时，然后冷却到100℃。加入碳酸亚乙基酯(115.7毫升)，并将混合物在160℃下加热16小时。将反应物料冷至室温，并加入10毫升异丙醇。用10升己烷稀释反应物料，用水洗涤3次，用盐水洗涤1次。有机层在无水硫酸镁上干燥，过滤，并在真空下除去溶剂，得到1301.7克所需的黄色油状产物。
实施例4
下式化合物的制备
将实施例2的15.0克醇和2.6克4-硝基苯甲酸和0.24克对-甲苯磺酸加到装有磁搅拌器、温度计、Dean-Stark冷阱、回流冷凝器和氮气进口的烧瓶中。将混合物在130℃下搅拌16小时，冷却至室温，并用200毫升己烷稀释。用饱和碳酸氢钠水溶液洗涤2次，随后用饱和的氯化钠水溶液洗涤一次。然后在无水硫酸镁上干燥有机相，过滤并在真空下除去溶剂，得到15.0克所需的褐色油状产物。油经硅胶色谱分离，用己烷/乙酸乙酯(9∶1)冲洗，得到14.0克所需的黄色油状产物。1H NMR(CDCl3)d 8.3(AB quartet，4H)，7.25(d，2H)，6.85(d，2H)，4.7(t，2H)，4.3(t，2H)，0.7-1.6(m，137H).
实施例5
下式化合物的制备
将实施例3的15.0克醇和2.7克4-硝基苯甲酸和0.23克对-甲苯磺酸加到装有磁搅拌器、温度计、Dean-Stark冷阱、回流冷凝器和氮气进口的烧瓶中。将混合物在130℃下搅拌16小时，冷却至室温，并用200毫升己烷稀释。用饱和碳酸氢钠水溶液洗涤2次，随后用饱和的氯化钠水溶液洗涤1次。然后在无水硫酸镁上干燥有机相，过滤并在真空下除去溶剂，得到16.0克所需的褐色油状产物。油经硅胶色谱分离，用己烷/乙酸乙酯(8∶2)冲洗，得到15.2克所需的黄色油状产物。1H NMR(CDCl3)d 8.2(AB quartet，4H)，7.25(d，2H)，6.85(d，2H)，5.55(hx，1H)，4.1(t，2H)，0.6-1.8(m，140H).
实施例6
将含有1.0克10％钯/炭的9.4克实施例4的产物于100毫升乙酸乙酯的溶液在Parr低压加氢反应器中，在35-40psi下氢化16小时。过滤出催化剂，并在真空下除去溶剂，得到7.7克所需的黄色油状产物。1H NMR(CDCl3)d 7.85(d，2H)，7.3(d，2H)，6.85(d，2H)，6.6(d，2H)，4.6(t，2H)，4.25(t，2H)，4.05(bs，2H)，0.7-1.6(m，137H).
实施例7
下式化合物的制备
将含有1.0克10％钯/炭的15.2克实施例5的产物于200毫升乙酸乙酯的溶液在Parr低压加氢反应器中，在35-40psi下氢化16小时。过滤出催化剂，并在真空下除去溶剂，得到15.0克所需的黄色油状产物1H NMR(CDCl3/D2O)d 7.85(d，2H)，7.25(d，2H)，6.85(d，2H)，6.6(d，2H)，5.4(hx，1H)，3.8-4.2(m，4H)，0.6-1.8(m，140H).
实施例8
单缸发动机试验
试验化合物与汽油调合，并用ASTM/CFR单缸发动机试验测定其降低沉积物的能力。
使用Waukesha CFR单缸发动机。每一试验进行15小时，试验结束时取下进气阀，用己烷洗涤并称重。从试验结束时的阀重减去以前测定的清洁阀的重量。两重量之间的差为沉积物的重量。沉积物量越少说明添加剂越好。试验的操作条件如下：水套温度200°F；进气歧管真空度为12英寸汞柱，空气/燃料比为12，点火时限为40BTC；发动机速度为1800转/分；曲轴箱油为商业30W油。
对于每一试验化合物，按毫克计含碳质沉积物在进气阀上的数量列入表I。
表I
进气阀沉积物重(毫克)样品1 试验1 试验2 平均基准燃料 354.9 333.5 344.2实施例4 169.0 178.0 173.5实施例6 13.4 12.2 12.8
1150ppma
在上述单缸发动机试验中使用的基准燃料为不含燃料清净剂的普通辛烷值的未加铅汽油。试验化合物与基准燃料混合，得到150ppma浓缩物。
表I的数据说明与基准燃料相比，本发明的聚烷基苯氧基烷醇的芳族酯化合物(实施例4和6)使进气阀的沉积物有显著下降。
Claims (42)
1.一种下式的化合物或其燃料可溶性盐：式中R为羟基或-(CH2)X-NH2，其中X为0或1；R1为氢、羟基或氨基；R2为氢或有1-6个碳原子的低级烷基；R3为氢；和R4为平均分子量为700至3000的聚烷基。
2.根据权利要求1的化合物，其中R为氨基或-(CH2)2NH2，其中x为0或1。
3.根据权利要求2的化合物，其中R为氨基。
4.根据权利要求1的化合物，其中R1为氢、羟基或氨基。
5.根据权利要求4的化合物，其中R1为氢或羟基。
6.根据权利要求5的化合物，其中R1为氢。
7.根据权利要求1的化合物，其中R2为氢或有1-4个碳原子的低碳烷基。
8.根据权利要求7的化合物，其中R2为氢、甲基或乙基。
9.根据权利要求1的化合物，其中R4为平均分子量为900至2500的聚烷基。
10.根据权利要求1的化合物，其中R4为由聚丙烯或聚异丁烯得到的聚烷基。
11.根据权利要求10的化合物，其中R4为由聚异丁烯得到的聚烷基。
12.根据权利要求11的化合物，其中聚异丁烯含有至少20％甲基亚乙烯基异构体。
13.根据权利要求1的化合物，其中R为氨基，R1、R2和R3为氢，而R4为由聚异丁烯得到的聚烷基。
14.一种燃料组合物，它含有主要量的汽油或柴油沸程的烃类以及有效控制沉积物量的下式的化合物或其燃料可溶性盐：
式中，R为羟基或-(CH2)X-NH2，其中X为0或1；R1为氢、羟基或氨基；R2为氢或有1-6个碳原子的低碳烷基；R3为氢；和R4为平均分子量为700至3000的聚烷基；
15.根据权利要求14的燃料组合物，其中R为氨基或-(CH2)2NH2，X为0或1。
16.根据权利要求15的燃料组合物，其中R为氨基。
17.根据权利要求14的燃料组合物，其中R1为氢、羟基或氨基。
18.根据权利要求17的燃料组合物，其中R1为氢或羟基。
19.根据权利要求18的燃料组合物，其中R1为氢。
20.根据权利要求14的燃料组合物，其中R2为氢或有1-4个碳原子的低碳烷基。
21.根据权利要求20的燃料组合物，其中R2为氢、甲基或乙基。
22.根据权利要求14的燃料组合物，其中R4为平均分子量为900至2500的聚烷基。
23.根据权利要求14的燃料组合物，其中R4为由聚丙烯或聚异丁烯得到的聚烷基。
24.根据权利要求23的燃料组合物，其中R4为由聚异丁烯得到的聚烷基。
25.根据权利要求24的燃料组合物，其中聚异丁烯含有至少20％甲基亚乙烯基异构体。
26.根据权利要求14的燃料组合物，其中R为氨基，R1、R2和R3为氢和R4为由聚异丁烯得到的聚烷基。
27.根据权利要求14的燃料组合物，其中组合物含有50至2000ppm所述的化合物。
28.根据权利要求14的燃料组合物，其中组合物还含有100至5000ppm燃料可溶性不挥发的载体流体。
29.一种燃料浓缩物，它含有一种主要量的沸程在汽油或柴油范围内的烃和有效控制沉积物量的下式化合物或其燃料可溶性盐：
式中，R为羟基或-(CH2)X-NH2，其中x为0或1；R1为氢、羟基或氨基；R2为氢或有1-6个碳原子的低碳烷基；R3为氢；以及R4为平均分子量为700至3000的聚烷基。
30.根据权利要求29的燃料浓缩物，其中R为氨基或-(CH2)2NH2，其中X为0或1。
31.根据权利要求30的燃料浓缩物，其中R为氨基。
32.根据权利要求29的燃料浓缩物，其中R1为氢或羟基。
33.根据权利要求32的燃料浓缩物，其中R1为氢。
34.根据权利要求29的燃料浓缩物，其中R2为氢或有1-4个碳原子的低碳烷基。
35.根据权利要求34的燃料浓缩物，其中R2为氢。
36.根据权利要求34的燃料浓缩物，其中R2为氢、甲基或乙基。
37.根据权利要求29的燃料浓缩物，其中R4为平均分子量为900至2500的聚烷基。
38.根据权利要求29的燃料浓缩物，其中R4为由聚丙烯或聚异丁烯得到的聚烷基。
39.根据权利要求38的燃料浓缩物，其中R4为由聚异丁烯得到的聚烷基。
40.根据权利要求39的燃料浓缩物，其中聚异丁烯含有至少20％甲基亚乙烯基异构体。
41.根据权利要求29的燃料浓缩物，其中R为氨基，R1、R2和R3为氢，而R4为由聚异丁烯得到的聚烷基。
42.根据权利要求29的燃料浓缩物，其中燃料浓缩物还含有20至60％(重量)燃料可溶性不挥发的载体流体。
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| US08/647,486 | 1996-05-14 | ||
| US08/647,486 US5618320A (en) | 1996-05-14 | 1996-05-14 | Aromatic esters of polyalkylphenoxyalkanols and fuel compositions containing the same |
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| CN1092703C true CN1092703C (zh) | 2002-10-16 |
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| CA (1) | CA2226668C (zh) |
| DE (1) | DE69723395T2 (zh) |
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| US845981A (en) * | 1906-02-23 | 1907-03-05 | Harold Douglas Singer | Nursing-bottle. |
| US4515981A (en) * | 1982-09-21 | 1985-05-07 | Toyo Tire & Rubber Company, Limited | Polyetherpolyol derivative and process for preparing the same |
| US5366589A (en) * | 1993-11-16 | 1994-11-22 | Motorola, Inc. | Bonding pad with circular exposed area and method thereof |
| US5380345A (en) * | 1993-12-03 | 1995-01-10 | Chevron Research And Technology Company | Polyalkyl nitro and amino aromatic esters and fuel compositions containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1997043358A1 (en) | 1997-11-20 |
| DE69723395T2 (de) | 2004-02-05 |
| MX9800305A (es) | 1998-09-30 |
| US5749929A (en) | 1998-05-12 |
| NZ329353A (en) | 1999-10-28 |
| CN1193337A (zh) | 1998-09-16 |
| JPH11509577A (ja) | 1999-08-24 |
| AU714673B2 (en) | 2000-01-06 |
| DE69723395D1 (de) | 2003-08-14 |
| KR19990028814A (ko) | 1999-04-15 |
| AU2939797A (en) | 1997-12-05 |
| EP0840773A1 (en) | 1998-05-13 |
| EP0840773A4 (en) | 2000-02-02 |
| CA2226668A1 (en) | 1997-11-20 |
| EP0840773B1 (en) | 2003-07-09 |
| KR19990028815A (ko) | 1999-04-15 |
| US5618320A (en) | 1997-04-08 |
| KR100436335B1 (ko) | 2004-08-25 |
| JP3786707B2 (ja) | 2006-06-14 |
| BR9702206A (pt) | 1999-12-28 |
| KR100436336B1 (ko) | 2004-08-06 |
| CA2226668C (en) | 2005-10-11 |
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