CN103695053A - 一种柴油十六烷值改进剂的合成方法 - Google Patents
一种柴油十六烷值改进剂的合成方法 Download PDFInfo
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- CN103695053A CN103695053A CN201310725877.2A CN201310725877A CN103695053A CN 103695053 A CN103695053 A CN 103695053A CN 201310725877 A CN201310725877 A CN 201310725877A CN 103695053 A CN103695053 A CN 103695053A
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- number improver
- synthetic method
- diesel
- cetane
- reaction
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- 238000010189 synthetic method Methods 0.000 title claims abstract description 16
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 title abstract description 38
- 239000002283 diesel fuel Substances 0.000 title abstract description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 35
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 235000006408 oxalic acid Nutrition 0.000 claims abstract description 11
- 239000007921 spray Substances 0.000 claims abstract description 11
- 230000032050 esterification Effects 0.000 claims abstract description 7
- 238000005886 esterification reaction Methods 0.000 claims abstract description 7
- 230000035484 reaction time Effects 0.000 claims abstract description 7
- 230000007935 neutral effect Effects 0.000 claims abstract description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 7
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003729 cation exchange resin Substances 0.000 claims description 6
- 238000004073 vulcanization Methods 0.000 claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract description 5
- 238000002485 combustion reaction Methods 0.000 abstract description 4
- 239000000446 fuel Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract 2
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 238000011112 process operation Methods 0.000 abstract 1
- 238000005070 sampling Methods 0.000 abstract 1
- -1 Manganse Dioxide Chemical compound 0.000 description 18
- 238000000034 method Methods 0.000 description 15
- 229910002651 NO3 Inorganic materials 0.000 description 13
- 230000000694 effects Effects 0.000 description 10
- 230000000996 additive effect Effects 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 5
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229910010413 TiO 2 Inorganic materials 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 238000004523 catalytic cracking Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- LNNXFUZKZLXPOF-UHFFFAOYSA-N 2-methylpropyl nitrate Chemical compound CC(C)CO[N+]([O-])=O LNNXFUZKZLXPOF-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- HSNWZBCBUUSSQD-UHFFFAOYSA-N amyl nitrate Chemical compound CCCCCO[N+]([O-])=O HSNWZBCBUUSSQD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- IDNUEBSJWINEMI-UHFFFAOYSA-N ethyl nitrate Chemical compound CCO[N+]([O-])=O IDNUEBSJWINEMI-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 229910000765 intermetallic Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000005077 polysulfide Substances 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 150000008117 polysulfides Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PWONZZKXEVZFDV-UHFFFAOYSA-N 6-methylheptyl nitrate Chemical compound CC(C)CCCCCO[N+]([O-])=O PWONZZKXEVZFDV-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 229910001864 baryta Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- SVOAENZIOKPANY-UHFFFAOYSA-L copper;octadec-9-enoate Chemical compound [Cu+2].CCCCCCCCC=CCCCCCCCC([O-])=O.CCCCCCCCC=CCCCCCCCC([O-])=O SVOAENZIOKPANY-UHFFFAOYSA-L 0.000 description 1
- HLYOOCIMLHNMOG-UHFFFAOYSA-N cyclohexyl nitrate Chemical compound [O-][N+](=O)OC1CCCCC1 HLYOOCIMLHNMOG-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- AUBDSFLQOBEOPX-UHFFFAOYSA-N hexa-1,5-dien-3-yne Chemical group C=CC#CC=C AUBDSFLQOBEOPX-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- TXQBMQNFXYOIPT-UHFFFAOYSA-N octyl nitrate Chemical compound CCCCCCCCO[N+]([O-])=O TXQBMQNFXYOIPT-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical class [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000009671 shengli Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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- Liquid Carbonaceous Fuels (AREA)
Abstract
Description
Claims (8)
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CN201310725877.2A CN103695053B (zh) | 2013-12-25 | 2013-12-25 | 一种柴油十六烷值改进剂的合成方法 |
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CN201310725877.2A CN103695053B (zh) | 2013-12-25 | 2013-12-25 | 一种柴油十六烷值改进剂的合成方法 |
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CN103695053A true CN103695053A (zh) | 2014-04-02 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108658773A (zh) * | 2018-04-26 | 2018-10-16 | 北京兴有丰科科技发展有限公司 | 利用纳米氧化物辅助制备十六烷值改进剂的方法 |
Citations (7)
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---|---|---|---|---|
GB761296A (en) * | 1953-11-06 | 1956-11-14 | Exxon Research Engineering Co | Improvements in or relating to methylene ether esters as synthetic lubricants |
US4740215A (en) * | 1987-01-27 | 1988-04-26 | Union Oil Company Of California | Composition for cetane improvement of diesel fuels |
CN1687001A (zh) * | 2005-04-07 | 2005-10-26 | 浙江工业大学 | 一种有机酸酯化方法 |
CN101054540A (zh) * | 2007-05-30 | 2007-10-17 | 哈尔滨工业大学 | 一种柴油复合添加剂 |
CN101362970A (zh) * | 2007-08-10 | 2009-02-11 | 印度石油股份有限公司 | 新的合成燃料及其制备方法 |
CN101855195A (zh) * | 2007-11-14 | 2010-10-06 | 昭和电工株式会社 | 制造乙酸正丙酯和乙酸烯丙酯的方法 |
CN102051248A (zh) * | 2009-11-10 | 2011-05-11 | 济南开发区星火科学技术研究院 | 一种提高柴油十六烷值的方法 |
-
2013
- 2013-12-25 CN CN201310725877.2A patent/CN103695053B/zh active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB761296A (en) * | 1953-11-06 | 1956-11-14 | Exxon Research Engineering Co | Improvements in or relating to methylene ether esters as synthetic lubricants |
US4740215A (en) * | 1987-01-27 | 1988-04-26 | Union Oil Company Of California | Composition for cetane improvement of diesel fuels |
CN1687001A (zh) * | 2005-04-07 | 2005-10-26 | 浙江工业大学 | 一种有机酸酯化方法 |
CN101054540A (zh) * | 2007-05-30 | 2007-10-17 | 哈尔滨工业大学 | 一种柴油复合添加剂 |
CN101362970A (zh) * | 2007-08-10 | 2009-02-11 | 印度石油股份有限公司 | 新的合成燃料及其制备方法 |
CN101855195A (zh) * | 2007-11-14 | 2010-10-06 | 昭和电工株式会社 | 制造乙酸正丙酯和乙酸烯丙酯的方法 |
CN102051248A (zh) * | 2009-11-10 | 2011-05-11 | 济南开发区星火科学技术研究院 | 一种提高柴油十六烷值的方法 |
Non-Patent Citations (4)
Title |
---|
代秀川等: ""对甲苯磺酸催化合成草酸二异戊酯的研究"", 《应用化工》, vol. 35, no. 8, 31 August 2006 (2006-08-31), pages 598 - 600 * |
孙琳等: "草酸二丁酯的催化合成", 《化学工程师》, no. 11, 30 November 2005 (2005-11-30), pages 15 - 16 * |
杨栩等: "用硫酸铁和阳离子树脂复合催化剂合成草酸二丁酯", 《辽宁师专学报》, vol. 15, no. 3, 30 September 2013 (2013-09-30), pages 96 - 98 * |
闫锋等: "十六烷值改进剂研究进展", 《抚顺石油学院学报》, vol. 21, no. 4, 31 December 2001 (2001-12-31), pages 6 - 8 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108658773A (zh) * | 2018-04-26 | 2018-10-16 | 北京兴有丰科科技发展有限公司 | 利用纳米氧化物辅助制备十六烷值改进剂的方法 |
CN108658773B (zh) * | 2018-04-26 | 2020-04-24 | 北京兴有丰科科技发展有限公司 | 利用纳米氧化物辅助制备十六烷值改进剂的方法 |
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