EP2514804A1 - Utilisation de 1,1-dialkoxyalkanes pour l'augmentation du pouvoir antidétonant de l'essence - Google Patents

Utilisation de 1,1-dialkoxyalkanes pour l'augmentation du pouvoir antidétonant de l'essence Download PDF

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Publication number
EP2514804A1
EP2514804A1 EP20110163065 EP11163065A EP2514804A1 EP 2514804 A1 EP2514804 A1 EP 2514804A1 EP 20110163065 EP20110163065 EP 20110163065 EP 11163065 A EP11163065 A EP 11163065A EP 2514804 A1 EP2514804 A1 EP 2514804A1
Authority
EP
European Patent Office
Prior art keywords
gasoline
general formula
och
knock
compounds
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.)
Withdrawn
Application number
EP20110163065
Other languages
German (de)
English (en)
Inventor
Magomed-Zagir Vagabov
Rustam Vagabov
Zaira Mangueva
Filzia Latypova
Elvin Rakhmankulov
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Top-Biofuel & Co KG GmbH
Original Assignee
Top-Biofuel & Co KG GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Top-Biofuel & Co KG GmbH filed Critical Top-Biofuel & Co KG GmbH
Priority to EP20110163065 priority Critical patent/EP2514804A1/fr
Priority to PCT/EP2012/057199 priority patent/WO2012143465A1/fr
Priority to CA 2833473 priority patent/CA2833473A1/fr
Priority to EP12720823.9A priority patent/EP2699656A1/fr
Priority to CN201280019111.6A priority patent/CN103597061A/zh
Priority to US14/112,873 priority patent/US9005316B2/en
Priority to RU2013151748/04A priority patent/RU2567541C2/ru
Publication of EP2514804A1 publication Critical patent/EP2514804A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C10L10/10—Use of additives to fuels or fires for particular purposes for improving the octane number
    • 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
    • C10L1/02—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only
    • C10L1/023—Liquid carbonaceous fuels essentially based on components consisting of carbon, hydrogen, and oxygen only for spark ignition
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • 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
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/30—Physical properties of feedstocks or products
    • C10G2300/305—Octane number, e.g. motor octane number [MON], research octane number [RON]
    • 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
    • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
    • C10L2200/0415—Light distillates, e.g. LPG, naphtha
    • C10L2200/0423—Gasoline

Definitions

  • the present invention relates to the use of one or more of the acetals of general formula 1 as an anti-knock agent for gasoline (motor gasoline).
  • the invention also relates to the motor gasoline obtained by adding the anti-knock agent according to the invention.
  • motor gasoline is used in the following, which is colloquially referred to as gasoline.
  • the knock resistance is the property of the gasoline used in a gasoline engine not to burn uncontrolled by auto-ignition ("knocking"), but controlled exclusively by spark, injection or compression.
  • the motor gasoline additives are therefore added, the so-called anti-knock agents that reduce the tendency to knock the gasoline engine by increasing the octane number.
  • the octane number thus defines the measure of the knock resistance of the motor gasoline.
  • the research octane number is determined according to DIN EN ISO 5164 (ASTM D 2699) and describes the knock behavior at low engine load and low speeds.
  • the engine octane number is determined according to DIN EN ISO 5163 (ASTM D 2700) and describes the behavior at high engine load and high thermal load.
  • the object of the present invention was to provide alternative anti-knock agents for motor gasoline, which cause a significant increase in both the research octane number and the engine octane number.
  • the motor gasoline of the invention comprises, in addition to the 1,1-dialkoxyalkanes of the general formula I and customary additives, no C 1 -C 4 -alcohols which are described in US Pat US 6,514,299 in combination with special 1,1-dialkoxyalkanes are described as anti-knock agents.
  • the motor gasoline does not include any ketals general formula R 3 OC (R 1 ) (R 2 ) -OR 4 , which in DE 31 33 899 A1 in combination with dimethoxymethane are described as anti-knock agent.
  • R 1 in formula I preferably denotes CH 3 , C 2 H 5 , C 3 H 7 or C 4 H 9 , particularly preferably CH 3 .
  • C 3 H 7 and C 4 H 9 in the context of the invention mean the n-propyl or n-butyl radical, while iC 3 H 7 and iC 4 H 9 denote the isopropyl or isobutyl radical.
  • methylal as obtained in industrial isoprene production after the m-dioxane route methylalffle fraction, which is a notedtonnagiges waste product, as an anti-knock additive.
  • the industrially produced and inventively used methylalumble fraction is usually about 7 to 11Vol.% Of C 4 - and C 5 hydrocarbons, to about 67 to 72Vol.% Of methylal (with traces of methanol), to about 19 to 23% by volume from trimethylcarbinol and from 0.05 to 0.09% by volume from 4,4-dimethyl-1,3-dioxane.
  • R 2 represents the methyl radical.
  • R 1 preferably denotes CH 3 , C 2 H 5 , C 3 H 7 or C 4 H 9 , particularly preferably methyl or ethyl.
  • Table 1 1,1-dialkoxyalkanes listed in Table 1 were synthesized by known methods and their boiling point and refractive index were determined.
  • Table 1 1,1-dialkoxyalkane MG Boiling point ° C n d 20 CH 3 OCH 2 OCH 3 76.09 42-44 1.3534 C 2 H 5 OCH 2 OC 2 H 5 104.15 89 1.3534 C 3 H 7 OCH 2 OC 3 H 7 132.21 138-139 1.3921 iC 3 H 7 OCH 2 O iC 3 H 7 132.21 120 1.3835 C 4 H 9 OCH 2 OC 4 H 9 160.26 181-182 1.4058 iC 4 H 9 OCH 2 OiC 4 H 9 160.26 165 1.4002 CH 3 OCH (CH 3 ) OCH 3 90.12 64.5 1.36666 C 2 H 5 OCH (CH 3 ) OC 2 H 5 118.17 103 1.3819 C 3 H 7 OCH (CH 3 ) OC 3 H

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Combustion & Propulsion (AREA)
  • Liquid Carbonaceous Fuels (AREA)
EP20110163065 2011-04-19 2011-04-19 Utilisation de 1,1-dialkoxyalkanes pour l'augmentation du pouvoir antidétonant de l'essence Withdrawn EP2514804A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP20110163065 EP2514804A1 (fr) 2011-04-19 2011-04-19 Utilisation de 1,1-dialkoxyalkanes pour l'augmentation du pouvoir antidétonant de l'essence
PCT/EP2012/057199 WO2012143465A1 (fr) 2011-04-19 2012-04-19 Utilisation de 1,1-diéthoxyéthane pour améliorer le pouvoir antidétonant de l'essence pour moteur
CA 2833473 CA2833473A1 (fr) 2011-04-19 2012-04-19 Utilisation de 1,1-diethoxyethane pour ameliorer le pouvoir antidetonant de l'essence pour moteur
EP12720823.9A EP2699656A1 (fr) 2011-04-19 2012-04-19 Utilisation de 1,1-diéthoxyéthane pour améliorer le pouvoir antidétonant de l'essence pour moteur
CN201280019111.6A CN103597061A (zh) 2011-04-19 2012-04-19 1,1-二乙氧基乙烷用于增加车用汽油的抗爆震性的用途
US14/112,873 US9005316B2 (en) 2011-04-19 2012-04-19 Use of 1,1-diethoxyethane for increasing knocking resistance of automotive gasoline
RU2013151748/04A RU2567541C2 (ru) 2011-04-19 2012-04-19 Применение 1,1-диэтоксиэтана в качестве антидетонационной присадки для увеличения детонационной стойкости автомобильного бензина

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP20110163065 EP2514804A1 (fr) 2011-04-19 2011-04-19 Utilisation de 1,1-dialkoxyalkanes pour l'augmentation du pouvoir antidétonant de l'essence

Publications (1)

Publication Number Publication Date
EP2514804A1 true EP2514804A1 (fr) 2012-10-24

Family

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Family Applications (2)

Application Number Title Priority Date Filing Date
EP20110163065 Withdrawn EP2514804A1 (fr) 2011-04-19 2011-04-19 Utilisation de 1,1-dialkoxyalkanes pour l'augmentation du pouvoir antidétonant de l'essence
EP12720823.9A Withdrawn EP2699656A1 (fr) 2011-04-19 2012-04-19 Utilisation de 1,1-diéthoxyéthane pour améliorer le pouvoir antidétonant de l'essence pour moteur

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP12720823.9A Withdrawn EP2699656A1 (fr) 2011-04-19 2012-04-19 Utilisation de 1,1-diéthoxyéthane pour améliorer le pouvoir antidétonant de l'essence pour moteur

Country Status (6)

Country Link
US (1) US9005316B2 (fr)
EP (2) EP2514804A1 (fr)
CN (1) CN103597061A (fr)
CA (1) CA2833473A1 (fr)
RU (1) RU2567541C2 (fr)
WO (1) WO2012143465A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6406974B2 (ja) * 2014-10-24 2018-10-17 理研香料ホールディングス株式会社 燃料用着臭剤

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1582420A (en) * 1925-07-09 1926-04-27 Nikaido Yasujuro Motor fuel
US2237660A (en) * 1939-01-14 1941-04-08 Standard Oil Dev Co Polyfurcous fuel
US3869262A (en) * 1971-05-05 1975-03-04 Oesterr Hiag Werke Ag Fuel and additive for the production thereof
DE3133899A1 (de) 1980-09-16 1982-04-08 VEB Leuna-Werke "Walter Ulbricht", DDR 4220 Leuna Kraftstoffe fuer otto-motoren
US4374648A (en) * 1980-05-30 1983-02-22 Chevron Research Company Motor fuel composition
US6514299B1 (en) 2000-11-09 2003-02-04 Millennium Fuels Usa, Llc Fuel additive and method therefor

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2842432A (en) * 1953-12-07 1958-07-08 Texas Co Supplementary fuel mixture for cold starting diesel engines
US4276055A (en) * 1979-09-05 1981-06-30 Huang James P H Novel fuel composition and the process of preparing same
DE19702989A1 (de) * 1997-01-28 1998-07-30 Clariant Gmbh Umweltfreundlicher Dieseltreibstoff
FR2764301B1 (fr) * 1997-06-09 1999-07-30 Elf Antar France Composition de carburant comprenant des composes oxygenes pour moteurs diesel
RU2008130735A (ru) * 2008-07-25 2010-01-27 Юрий Владимирович Политанский (RU) Автомобильное топливо и способ его получения

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1582420A (en) * 1925-07-09 1926-04-27 Nikaido Yasujuro Motor fuel
US2237660A (en) * 1939-01-14 1941-04-08 Standard Oil Dev Co Polyfurcous fuel
US3869262A (en) * 1971-05-05 1975-03-04 Oesterr Hiag Werke Ag Fuel and additive for the production thereof
US4374648A (en) * 1980-05-30 1983-02-22 Chevron Research Company Motor fuel composition
DE3133899A1 (de) 1980-09-16 1982-04-08 VEB Leuna-Werke "Walter Ulbricht", DDR 4220 Leuna Kraftstoffe fuer otto-motoren
US6514299B1 (en) 2000-11-09 2003-02-04 Millennium Fuels Usa, Llc Fuel additive and method therefor

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ANONYMOUS: "MATERIAL SAFETY DATA SHEET METHYLAL", 12 February 2007 (2007-02-12), XP055000727, Retrieved from the Internet <URL:http://www.viromet.ro/files/fise/en/metilal_.pdf> [retrieved on 20110615] *
SUFLITA J M ET AL: "ANAEROBIC BIODEGRADATION OF KNOWN AND POTENTIAL GASOLINE OXYGENATES IN THE TERRESTRIAL SUBSURFACE", ENVIRONMENTAL SCIENCE AND TECHNOLOGY, AMERICAN CHEMICAL SOCIETY. EASTON, PA, US, vol. 27, no. 5, 1 May 1993 (1993-05-01), pages 976 - 978, XP000361027, ISSN: 0013-936X, DOI: 10.1021/ES00042A022 *

Also Published As

Publication number Publication date
EP2699656A1 (fr) 2014-02-26
CN103597061A (zh) 2014-02-19
WO2012143465A1 (fr) 2012-10-26
US9005316B2 (en) 2015-04-14
RU2567541C2 (ru) 2015-11-10
US20140123550A1 (en) 2014-05-08
CA2833473A1 (fr) 2012-11-26
RU2013151748A (ru) 2015-05-27

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