EP2594623A1 - Tertiobutyl hydroperoxide (TBHP) as a diesel additive - Google Patents

Tertiobutyl hydroperoxide (TBHP) as a diesel additive Download PDF

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Publication number
EP2594623A1
EP2594623A1 EP11189416.8A EP11189416A EP2594623A1 EP 2594623 A1 EP2594623 A1 EP 2594623A1 EP 11189416 A EP11189416 A EP 11189416A EP 2594623 A1 EP2594623 A1 EP 2594623A1
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EP
European Patent Office
Prior art keywords
tbhp
fuel
additive
weight
tert
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.)
Ceased
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EP11189416.8A
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German (de)
French (fr)
Inventor
Erfindernennung liegt noch nicht vor Die
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United Initiators GmbH and Co KG
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United Initiators GmbH and Co KG
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Priority to EP11189416.8A priority Critical patent/EP2594623A1/en
Priority to MX2014005821A priority patent/MX2014005821A/en
Priority to US14/358,831 priority patent/US9303224B2/en
Priority to ES12784622T priority patent/ES2864214T3/en
Priority to EP12784622.8A priority patent/EP2780435B1/en
Priority to PCT/EP2012/072877 priority patent/WO2013072478A1/en
Priority to CN201280056319.5A priority patent/CN103998582B/en
Publication of EP2594623A1 publication Critical patent/EP2594623A1/en
Priority to ZA2014/03247A priority patent/ZA201403247B/en
Priority to IN1024/KOLNP/2014A priority patent/IN2014KN01024A/en
Ceased 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
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/1811—Organic compounds containing oxygen peroxides; ozonides
    • 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
    • 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
    • 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
    • C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development
    • 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
    • C10L10/12—Use of additives to fuels or fires for particular purposes for improving the cetane 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
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
    • C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
    • C10L1/1824—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms mono-hydroxy
    • 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
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/23—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
    • C10L1/231—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites nitro compounds; nitrates; nitrites
    • 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
    • C10L2270/00—Specifically adapted fuels
    • C10L2270/02—Specifically adapted fuels for internal combustion engines
    • C10L2270/026—Specifically adapted fuels for internal combustion engines for diesel engines, e.g. automobiles, stationary, marine
    • 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
    • C10L2300/00—Mixture of two or more additives covered by the same group of C10L1/00 - C10L1/308
    • C10L2300/20—Mixture of two components

Definitions

  • the present invention relates to the use of tertiary butyl hydroperoxide (TBHP) and blends thereof as a fuel additive, and more particularly as an additive to diesel fuel.
  • TBHP tertiary butyl hydroperoxide
  • the cetane number is a characteristic parameter for the combustion quality of diesel fuel.
  • the cetane number is a measure of the ignition or the ignition delay, ie the time between the start of the fuel injection and the beginning of the combustion.
  • a rapid ignition followed by a uniform and complete combustion as possible.
  • the higher the cetane number the shorter the ignition delay and the better the combustion quality.
  • cetane number-increasing additives are also used in US 2,763,537 including acrylates, nitrites, nitroso compounds, diazo compounds and organic peroxides.
  • Organic peroxides are currently not commercially used as diesel additives with the exception of small amounts of DTBP (di-tert-butyl peroxide). This for cost, security and compatibility reasons.
  • peroxide preparations often contain substantial amounts of water as phlegmatizers, are thermally or chemically unstable, can not be used commercially as fuel additives because of the raw materials or production processes used, or contain aromatic radicals which negatively influence pollutant emissions.
  • Water-stabilized peroxides are unsuitable as a fuel additive, since water does not mix with the fuel, but forms a two-phase system.
  • Organic peroxides are thermally labile compounds that decompose exothermically with cleavage of the peroxide oxygen-oxygen bond. Therefore, for safety reasons, organic peroxides often have to be phlegmatized for safe handling or safe transport or are already produced technically in dilution.
  • An object of the present invention was to provide an improved fuel additive, in particular with regard to pollutant emissions, effectiveness, manageability and costs.
  • the invention therefore relates to a fuel comprising tert-butyl hydroperoxide (TBHP) as an additive.
  • TBHP tert-butyl hydroperoxide
  • tert-butyl hydroperoxide in particular in anhydrous form, is suitable as a fuel additive.
  • the use of TBHP as an additive increases the cetane number of the fuel and preferably raises it above the base fuel by a value of at least 2, more preferably at least 3, even more preferably at least 4 and most preferably at least 5.
  • the cetane number can be determined, for example, according to ASTM 0613. A Increasing the cetane number is a measure of improving the ignitability of the fuel.
  • the pollutant emission in particular the hydrocarbon emission and / or the carbon monoxide emission is significantly reduced.
  • Anhydrous TBHP is preferably used according to the invention as a fuel additive.
  • Anhydrous means that the content of water in the TBHP composition is ⁇ 5% by weight, in particular ⁇ 1% by weight, even more preferably ⁇ 0.3% by weight.
  • TBHP is preferably used as an additive in an anhydrous organic solvent.
  • Polar and non-polar solvents can be used.
  • suitable nonpolar solvents are alkyls and in particular aliphatic hydrocarbons, in particular isododecane, isooctane, decane, nonane or / and n-octane or mixtures of different aliphatics.
  • polar solvents are, in particular, oxygen-containing solvents, such as, for example, alcohols or / and ethers.
  • Alkyl alcohols are preferably used as solvents, in particular C 1 -C 8 -alkyl alcohols, more preferably butanol and most preferably tert-butanol.
  • solvents in particular C 1 -C 8 -alkyl alcohols, more preferably butanol and most preferably tert-butanol.
  • the amount of TBHP in the additive is preferably at least 10% by weight, more preferably at least 30% by weight, and most preferably at least 50% by weight. Pure TBHP is not preferred for safety reasons.
  • the amount of TBHP in the additive is therefore preferably up to 90% by weight, more preferably up to 75% by weight, and most preferably up to 60% by weight.
  • the proportion of anhydrous organic solvent, in particular of tert-butanol is correspondingly at least 10% by weight, more preferably at least 25% by weight and most preferably at least 40% by weight and up to 90% by weight, more preferably up to 70 % By weight, and most preferably up to 50% by weight.
  • an additive which contains 30 to 70% by weight of TBHP in 70 to 30% by weight of tert-butanol.
  • the phlegmatization of TBHP in an oxygen-containing solvent and especially in tert-butanol increases the safety during the technical TBHP production, transport and further handling.
  • the oxygen content of the additive is also increased to reduce pollutants in the exhaust gas.
  • an oxygen content of about 29.3 wt.% Oxygen, of which about 9.8 wt.% Active oxygen is contained.
  • the fuel according to the invention may contain fuels or fuels known as base fuel, such as, for example, gasolines, in particular gasoline, super etc., diesel fuels such as diesel, biodiesel or the like, rapeseed methyl esters or oxymethylene ethers.
  • base fuel such as, for example, gasolines, in particular gasoline, super etc.
  • diesel fuels such as diesel, biodiesel or the like
  • TBHP Compared to the conventionally used 2-EHN combustion is improved by the inventive use of TBHP as an additive (especially lower hydrocarbon and soot emissions). Furthermore, TBHP contains no nitrogen, so that the associated problems and in particular the problem of the formation of nitrogen oxides is inventively reduced. Furthermore, TBHP is significantly safer in terms of safety than 2-EHN, especially in terms of decomposition.
  • a measure of the rate of decomposition and pressure build-up in the decomposition of a product is the Koenen test. The larger the Koenen value, the more violent the decomposition takes place.
  • the Koenenen for 2-EHN 1.0 while the Koenenen for a TBA phlegmatized TBHP is ⁇ 1.
  • TBHP advantageously has a higher flash point of 21 ° C.
  • the flashpoint of DTBP is significantly lower than that of TBHP and below room temperature at ⁇ 0 ° C.
  • the conductivity of DTBP is ⁇ 3 pS / m extremely low, so that replenishment of DTBP due to possible charge separations are very critical in terms of safety, since these charge separations a sufficient ignition energy to ignite DTBP can generate, since DTBP only requires a very low ignition energy of ⁇ 0.1 mJ.
  • the polar TBHP is conductive (> 1000 pS / m) and thus such charge separations no longer occur, so that TBHP can be handled much more safely than DTBP.
  • the fuel is preferably 0.001 wt% to 10 wt%, more preferably 0.01 wt% to 5 wt%, and most preferably 0.05 wt% to 2 wt% TBHP.
  • TBHP-containing additive according to the invention with other additives.
  • Preferred is e.g. the combination with other peroxides and in particular with di-tert-butyl peroxide (DTBP).
  • DTBP di-tert-butyl peroxide
  • an additive comprising TBHP and DTPB.
  • the weight ratio of TBHP and DTPB is preferably from 10:90 to 90:10.
  • the production of TBHP can be carried out according to known production methods.
  • the invention further relates to a fuel additive comprising TBHP and the use of TBHP to increase the cetane number.
  • Fuel comprising TBHP as an additive
  • a conventional base diesel fuel has a cetane number of 48.
  • An additive consisting of 55% by weight of TBHP and 45% by weight of tert-butanol in a concentration based on TBHP of 0.05% by weight of additive and in a concentration of 0.5% by weight is added to this fuel.
  • the addition of the additive significantly increases the cetane number.
  • the cetane number is significantly improved and at the same time without significant increase in consumption at the same engine power in the presence of the additive TBHP the emission of pollutants is significantly reduced.
  • Fuel comprising TBHP as an additive
  • an additive consisting of 28 wt% TBHP, 23 wt% TBA and 49 wt% DTBP in a concentration based on TBHP of 0.05 wt% and in a concentration of 0.05 wt% ,
  • the addition of the additive significantly increases the cetane number.
  • base diesel base diesel + 0.05 wt.% TBHP and base diesel + 0.5 wt.% TBHP
  • TBHP significantly improves the cetane number and at the same time significantly reduces pollutant emissions.

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  • 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)
  • Solid Fuels And Fuel-Associated Substances (AREA)
  • Liquid Carbonaceous Fuels (AREA)

Abstract

Fuel comprises tert-butyl hydroperoxide (TBHP) as an additive. An independent claim is included for the fuel additive comprising TBHP.

Description

Die vorliegende Erfindung betrifft die Verwendung von tert.-Butylhydroperoxid (TBHP) und Abmischungen hiervon als Kraftstoffadditiv und insbesondere als Additiv zu Dieselkraftstoff.The present invention relates to the use of tertiary butyl hydroperoxide (TBHP) and blends thereof as a fuel additive, and more particularly as an additive to diesel fuel.

Die Cetan-Zahl ist ein charakteristischer Parameter für die Verbrennungsqualität von Dieselkraftstoff. Die Cetan-Zahl ist ein Maß für die Zündwilligkeit bzw. die Zündverzögerung, also die Zeit zwischen dem Beginn der Kraftstoffeinspritzung und dem Beginn der Verbrennung. Günstig ist dabei eine rasche Zündung, gefolgt von einer gleichmäßigen und möglichst vollständigen Verbrennung. Je höher die Cetan-Zahl ist, desto kürzer die Zündverzögerung und desto besser die Verbrennungsqualität.The cetane number is a characteristic parameter for the combustion quality of diesel fuel. The cetane number is a measure of the ignition or the ignition delay, ie the time between the start of the fuel injection and the beginning of the combustion. Favorable is a rapid ignition, followed by a uniform and complete combustion as possible. The higher the cetane number, the shorter the ignition delay and the better the combustion quality.

Zur Erhöhung der Cetan-Zahl werden verschiedene Zusätze eingesetzt. Im kommerziellen Umfang wird derzeit nahezu ausschließlich 2-EHN (2-Ethylhexylnitrat) verwendet. Problematisch an diesem Zusatz sind seine hohe Giftigkeit, seine schlechte Lagerstabilität, sicherheitskritische Eigenschaften sowie beträchtliche Mehrkosten. Insbesondere aufgrund seiner Explosivität ist die Verwendung von 2-EHN problematisch. Weiterhin kann der Stickstoffgehalt zur erhöhten, unerwünschten NOX-Emissionen führen.To increase the cetane number, various additives are used. Commercially, almost exclusively 2-EHN (2-ethylhexyl nitrate) is currently used. The problem with this additive is its high toxicity, its poor storage stability, safety-critical properties and considerable additional costs. In particular, due to its explosiveness, the use of 2-EHN is problematic. Furthermore, the nitrogen content can lead to increased, unwanted NOX emissions.

Cetan-Zahl-erhöhende Zusätze werden beispielsweise auch in US 2,763,537 beschrieben, darunter Akylnitrate, Nitrite, Nitrosoverbindungen, Diazoverbindungen und Organische Peroxide. Organische Peroxide werden derzeit mit Ausnahme von geringen Mengen an DTBP (Ditertbutylperoxid) kommerziell nicht als Dieseladditive eingesetzt. Dies aus Kosten-, Sicherheits- und Kompatibilitätsgründen.For example, cetane number-increasing additives are also used in US 2,763,537 including acrylates, nitrites, nitroso compounds, diazo compounds and organic peroxides. Organic peroxides are currently not commercially used as diesel additives with the exception of small amounts of DTBP (di-tert-butyl peroxide). This for cost, security and compatibility reasons.

So enthalten kommerziell verfügbare Peroxidpreparationen oftmals als Phlegmatisierungsmittel beträchtliche Mengen an Wasser, sind thermisch oder chemisch zu instabil, aufgrund der verwendeten Rohstoffe bzw. Produktionsverfahren kommerziell als Kraftstoffadditiv nicht einsetzbar oder enthalten aromatische Reste, die den Schadstoffausstoß negativ beeinflussen. Mit Wasser phlegmatisierte Peroxide sind als Treibstoffzusatz aber ungeeignet, da sich Wasser nicht mit dem Treibstoff vermischt, sondern ein zweiphasiges System bildet.For example, commercially available peroxide preparations often contain substantial amounts of water as phlegmatizers, are thermally or chemically unstable, can not be used commercially as fuel additives because of the raw materials or production processes used, or contain aromatic radicals which negatively influence pollutant emissions. Water-stabilized peroxides are unsuitable as a fuel additive, since water does not mix with the fuel, but forms a two-phase system.

Organische Peroxide sind thermisch labile Verbindungen, die exotherm unter Spaltung der peroxidischen Sauerstoff-Sauerstoff-Bindung zerfallen. Daher müssen aus sicherheitstechnischen Überlegungen heraus Organische Peroxide zur sicheren Handhabung oder zum sicheren Transport oft phlegmatisiert werden bzw. werden bereits in Verdünnung technisch hergestellt.Organic peroxides are thermally labile compounds that decompose exothermically with cleavage of the peroxide oxygen-oxygen bond. Therefore, for safety reasons, organic peroxides often have to be phlegmatized for safe handling or safe transport or are already produced technically in dilution.

Insofern sind einige wasserfreie Peroxide nicht oder nur mit hohem technischen Aufwand erhältlich.In this respect, some anhydrous peroxides are not available or only with great technical effort.

Eine Aufgabe der vorliegenden Erfindung war es, ein verbessertes Kraftstoffadditiv bereitzustellen, insbesondere hinsichtlich Schadstoffausstoß, Wirksamkeit, Handhabbarkeit und Kosten.An object of the present invention was to provide an improved fuel additive, in particular with regard to pollutant emissions, effectiveness, manageability and costs.

Die Erfindung betrifft deshalb einen Kraftstoff umfassend tert.-Butylhydroperoxid (TBHP) als Additiv.The invention therefore relates to a fuel comprising tert-butyl hydroperoxide (TBHP) as an additive.

Überraschenderweise wurde gefunden, dass tert.-Butylhydroperoxid, insbesondere in wasserfreier Form als Kraftstoffadditiv geeignet ist. Durch den Einsatz von TBHP als Additiv wird insbesondere die Cetan-Zahl des Kraftstoffs erhöht und bevorzugt gegenüber dem Basiskraftstoff um einen Wert von mindestens 2, mehr bevorzugt mindestens 3, noch mehr bevorzugt mindestens 4 und am meisten bevorzugt wenigstens 5 angehoben. Die Cetan-Zahl kann beispielsweise gemäß ASTM 0613 bestimmt werden. Eine Erhöhung der Cetan-Zahl ist ein Maß für die Verbesserung der Zündwilligkeit des Kraftstoffs.Surprisingly, it has been found that tert-butyl hydroperoxide, in particular in anhydrous form, is suitable as a fuel additive. In particular, the use of TBHP as an additive increases the cetane number of the fuel and preferably raises it above the base fuel by a value of at least 2, more preferably at least 3, even more preferably at least 4 and most preferably at least 5. The cetane number can be determined, for example, according to ASTM 0613. A Increasing the cetane number is a measure of improving the ignitability of the fuel.

Weiterhin wurde festgestellt, dass bei annähernd gleichem Verbrauch die Schadstoffemission, insbesondere die Kohlenwasserstoffemission und/oder die Kohlenmonoxidemission, signifikant abgesenkt wird.Furthermore, it was found that at approximately the same consumption, the pollutant emission, in particular the hydrocarbon emission and / or the carbon monoxide emission is significantly reduced.

Bevorzugt wird erfindungsgemäß wasserfreies TBHP als Kraftstoffadditiv eingesetzt. Wasserfrei bedeutet dabei, dass der Gehalt an Wasser in der TBHP-Zusammensetzung < 5 Gew.%, insbesondere < 1 Gew.%, noch mehr bevorzugt< 0,3 Gew.% ist.Anhydrous TBHP is preferably used according to the invention as a fuel additive. Anhydrous means that the content of water in the TBHP composition is <5% by weight, in particular <1% by weight, even more preferably <0.3% by weight.

Durch den Einsatz von wasserfreiem TBHP, welches mit Dieseltreibstoff mischbar ist, wird vermieden, dass sich eine unerwünschte, zweite wässrige Phase bildet. Bevorzugt wird TBHP als Additiv in einem wasserfreien organischen Lösungsmittel eingesetzt. Es können polare und unpolare Lösungsmittel verwendet werden. Beispiele für geeignete unpolare Lösungsmittel sind Alkyle und insbesondere aliphatische Kohlenwasserstoffe, insbesondere Isododecan, Isooktan, Decan, Nonan oder/und n-Oktan bzw. Mischungen verschiedener Aliphaten. Beispiele für polare Lösungsmittel sind insbesondere sauerstoffenthaltende Lösungsmittel, wie beispielsweise Alkohole oder/und Ether. Bevorzugt werden Alkylalkohole als Lösungsmittel eingesetzt, insbesondere C1-C8-Alkylalkohole, mehr bevorzugt Butanol und am meisten bevorzugt tert.-Butanol. Durch Verwendung von Alkoholen und insbesondere von tert.-Butanol wird der Sauerstoffanteil in dem Kraftstoffadditiv weiter erhöht, was wünschenswert ist.By using anhydrous TBHP, which is miscible with diesel fuel, it is avoided that forms an undesirable second aqueous phase. TBHP is preferably used as an additive in an anhydrous organic solvent. Polar and non-polar solvents can be used. Examples of suitable nonpolar solvents are alkyls and in particular aliphatic hydrocarbons, in particular isododecane, isooctane, decane, nonane or / and n-octane or mixtures of different aliphatics. Examples of polar solvents are, in particular, oxygen-containing solvents, such as, for example, alcohols or / and ethers. Alkyl alcohols are preferably used as solvents, in particular C 1 -C 8 -alkyl alcohols, more preferably butanol and most preferably tert-butanol. By using alcohols, and especially tertiary butanol, the oxygen content in the fuel additive is further increased, which is desirable.

Gerade bei Einsatz eines Kraftstoffadditivs umfassend TBHP in tert.-Butanol (TBA) wurde eine signifikante Verringerung des Ruß- und Schadstoffausstoßes beobachtet.Especially when using a fuel additive comprising TBHP in tert-butanol (TBA), a significant reduction of soot and pollutant emissions was observed.

Die Menge an TBHP im Additiv beträgt vorzugsweise mindestens 10 Gew.%, mehr bevorzugt mindestens 30 Gew.% und am meisten bevorzugt mindestens 50 Gew.%. Reines TBHP ist aus sicherheitstechnischen Überlegungen nicht bevorzugt. Die Menge an TBHP im Additiv beträgt deshalb vorzugsweise bis zu 90 Gew.%, mehr bevorzugt bis zu 75 Gew.% und am meisten bevorzugt bis zu 60 Gew.%. Der Anteil an wasserfreiem organischen Lösungsmittel, insbesondere an tert-Butanol, beträgt entsprechend mindestens 10 Gew.%, mehr bevorzugt mindestens 25 Gew. % und am meisten bevorzugt mindestens 40 Gew.% und bis zu 90 Gew.%, mehr bevorzugt bis zu 70 Gew.% und am meisten bevorzugt bis zu 50 Gew. %.The amount of TBHP in the additive is preferably at least 10% by weight, more preferably at least 30% by weight, and most preferably at least 50% by weight. Pure TBHP is not preferred for safety reasons. The amount of TBHP in the additive is therefore preferably up to 90% by weight, more preferably up to 75% by weight, and most preferably up to 60% by weight. The proportion of anhydrous organic solvent, in particular of tert-butanol, is correspondingly at least 10% by weight, more preferably at least 25% by weight and most preferably at least 40% by weight and up to 90% by weight, more preferably up to 70 % By weight, and most preferably up to 50% by weight.

Als besonders geeignet und somit am meisten bevorzugt hat sich ein Additiv gezeigt, welches 30 bis 70 Gew.% TBHP in 70 bis 30 Gew.% tert-Butanol enthält. Durch die Phlegmatisierung von TBHP in einem sauerstoffhaltigen Lösungsmittel und insbesondere in tert.-Butanol wird die Sicherheit während der technischen TBHP-Produktion, dem Transport und der weiteren Handhabung erhöht.Particularly suitable and thus most preferred is an additive which contains 30 to 70% by weight of TBHP in 70 to 30% by weight of tert-butanol. The phlegmatization of TBHP in an oxygen-containing solvent and especially in tert-butanol increases the safety during the technical TBHP production, transport and further handling.

Anhand der Phlegmatisierung mit einem sauerstoffhaltigen Lösungsmittel, insbesondere tert.-Butylalkohol, wird zur Reduktion von Schadstoffen im Abgas auch der Sauerstoffgehalt des Additivs erhöht. Beispielsweise ist in einem Gemisch aus 55 Gew.% TBHP und 45 Gew.% TBA ein Sauerstoffgehalt von etwa 29,3 Gew.% Sauerstoff, davon etwa 9,8 Gew.% Aktivsauerstoff enthalten.Based on the phlegmatization with an oxygen-containing solvent, in particular tert-butyl alcohol, the oxygen content of the additive is also increased to reduce pollutants in the exhaust gas. For example, in a mixture of 55 wt.% TBHP and 45 wt.% TBA, an oxygen content of about 29.3 wt.% Oxygen, of which about 9.8 wt.% Active oxygen is contained.

Der erfindungsgemäße Kraftstoff kann als Basiskraftstoff bekannte Kraftstoffe oder Treibstoffe enthalten, wie beispielsweise Ottokraftstoffe, insbesondere Benzin, Super etc., Dieselkraftstoffe wie beispielsweise Diesel, Biodiesel oder ähnliche, Raps-Methylester oder Oxymethylenether. Durch das erfindungsgemäße Additiv wird insbesondere die Zündwilligkeit des Kraftstoffes erhöht. Weiterhin wird der Ausstoß an Ruß und Kohlenwasserstoffen im Verbrennungsmotor deutlich reduziert. Das erfindungsgemäß als Additiv eingesetzte TBHP ist auch sicherheitstechnisch gegenüber den üblicherweise eingesetzten Additiven deutlich besser handhabbar. Durch den Einsatz von TBHP in wasserfreier Form, insbesondere in einem wasserfreien organischen Lösungsmittel, wird die Bildung von zwei separaten Phasen vermieden und dadurch erst der Einsatz von TBHP als Kraftstoffadditiv ermöglicht.The fuel according to the invention may contain fuels or fuels known as base fuel, such as, for example, gasolines, in particular gasoline, super etc., diesel fuels such as diesel, biodiesel or the like, rapeseed methyl esters or oxymethylene ethers. By the additive according to the invention, in particular the ignitability of the fuel is increased. Furthermore, the emission of soot and hydrocarbons in the internal combustion engine is significantly reduced. The TBHP used according to the invention as an additive is also significantly easier to handle in terms of safety than the additives usually used. The use of TBHP in anhydrous form, especially in an anhydrous organic solvent, avoids the formation of two separate phases, thereby allowing the use of TBHP as fuel additive.

Im Vergleich zum herkömmlich eingesetzten 2-EHN wird durch den erfindungsgemäßen Einsatz von TBHP als Additiv die Verbrennung verbessert (insbesondere geringerer Kohlenwasserstoff-und Rußausstoß). Weiterhin enthält TBHP keinen Stickstoff, sodass die damit verbundenen Problematiken und insbesondere das Problem der Bildung von Stickoxiden erfindungsgemäß reduziert wird. TBHP ist weiterhin sicherheitstechnisch deutlich sicherer als 2-EHN, insbesondere in Bezug auf die Zersetzung.Compared to the conventionally used 2-EHN combustion is improved by the inventive use of TBHP as an additive (especially lower hydrocarbon and soot emissions). Furthermore, TBHP contains no nitrogen, so that the associated problems and in particular the problem of the formation of nitrogen oxides is inventively reduced. Furthermore, TBHP is significantly safer in terms of safety than 2-EHN, especially in terms of decomposition.

Ein Maß für die Zersetzungsgeschwindigkeit und den Druckaufbau bei der Zersetzung eines Produktes ist der Koenen-Test. Je größer der Koenen-Wert, desto heftiger erfolgt die Zersetzung.A measure of the rate of decomposition and pressure build-up in the decomposition of a product is the Koenen test. The larger the Koenen value, the more violent the decomposition takes place.

So ist der Koenen für 2-EHN = 1,0 während der Koenen für ein mit TBA phlegmatisiertes TBHP < 1 ist.Thus, the Koenen for 2-EHN = 1.0 while the Koenen for a TBA phlegmatized TBHP is <1.

Auch ist die bei der Zersetzung von 2-EHN freiwerdende Energie mit ΔH = 2210 J/g deutlich höher als die von einer TBHP-TBA Mischung mit ΔH = 729 J/g.Also, the energy released in the decomposition of 2-EHN is significantly higher with ΔH = 2210 J / g than that of a TBHP-TBA mixture with ΔH = 729 J / g.

Im Vergleich zum bereits als Kraftstoffadditiv eingesetzten di-tert.-Butylperoxid (DTBP) weist TBHP vorteilhafterweise einen höheren Flammpunkt von 21 °C auf. Der Flammpunkt von DTBP liegt z.B. deutlich niedriger als der von TBHP und unterhalb der Raumtemperatur bei < 0°C. Weiterhin ist die Leitfähigkeit von DTBP mit < 3 pS/m extrem niedrig, sodass Umfüllvorgänge von DTBP aufgrund von möglichen Ladungstrennungen sicherheitstechnisch sehr kritisch sind, da diese Ladungstrennungen eine ausreichende Zündenergie zum Zünden von DTBP erzeugen können, da DTBP nur eine sehr geringe Zündenergie von <0,1 mJ benötigt. Auch ist die bei der Zersetzungsenergie von DTBP freiwerdende Energie mit ΔH = 1370 J/g deutlich höher als die von dem mit TBA phlegmatisierten TBHP mit ΔH = 729 J/g.In comparison to the di-tert-butyl peroxide (DTBP) already used as a fuel additive, TBHP advantageously has a higher flash point of 21 ° C. For example, the flashpoint of DTBP is significantly lower than that of TBHP and below room temperature at <0 ° C. Furthermore, the conductivity of DTBP is <3 pS / m extremely low, so that replenishment of DTBP due to possible charge separations are very critical in terms of safety, since these charge separations a sufficient ignition energy to ignite DTBP can generate, since DTBP only requires a very low ignition energy of <0.1 mJ. Also, the energy released at the decomposition energy of DTBP is significantly higher with ΔH = 1370 J / g than that of the TBA phlegmatized TBHP with ΔH = 729 J / g.

Im Gegensatz zu dem unpolaren DTBP ist das polare TBHP leitfähig (> 1000 pS/m) und somit treten solche Ladungstrennungen nicht mehr auf, so dass TBHP erheblich sicherer als DTBP gehandhabt werden kann.Unlike the non-polar DTBP, the polar TBHP is conductive (> 1000 pS / m) and thus such charge separations no longer occur, so that TBHP can be handled much more safely than DTBP.

Erfindungsgemäß weist der Kraftstoff vorzugsweise 0,001 Gew.% bis 10 Gew.%, mehr bevorzugt 0,01 Gew.% bis 5 Gew.% und am meisten bevorzugt 0,05 Gew.% bis 2 Gew.% TBHP auf.In the present invention, the fuel is preferably 0.001 wt% to 10 wt%, more preferably 0.01 wt% to 5 wt%, and most preferably 0.05 wt% to 2 wt% TBHP.

Es ist erfindungsgemäß auch möglich, das erfindungsgemäße TBHP¬ enthaltende Additiv mit anderen Additiven zu kombinieren. Bevorzugt ist z.B. die Kombination mit anderen Peroxiden und insbesondere mit di-tert.-Butylperoxid (DTBP). Besonders bevorzugt ist ein Additiv, welches TBHP und DTPB umfasst.It is also possible according to the invention to combine the TBHP-containing additive according to the invention with other additives. Preferred is e.g. the combination with other peroxides and in particular with di-tert-butyl peroxide (DTBP). Particularly preferred is an additive comprising TBHP and DTPB.

Das Gewichtsverhältnis von TBHP und DTPB beträgt dabei bevorzugt von 10 : 90 bis 90 : 10.The weight ratio of TBHP and DTPB is preferably from 10:90 to 90:10.

Die Herstellung von TBHP kann nach bekannten Herstellungsverfahren erfolgen.The production of TBHP can be carried out according to known production methods.

Die Erfindung betrifft weiterhin ein Kraftstoffadditiv umfassend TBHP sowie die Verwendung von TBHP zur Erhöhung der Cetan-Zahl.The invention further relates to a fuel additive comprising TBHP and the use of TBHP to increase the cetane number.

Die Erfindung wird durch die folgenden Beispiele weiter erläutert.The invention is further illustrated by the following examples.

Beispiel 1example 1 Kraftstoff, umfassend TBHP als AdditivFuel, comprising TBHP as an additive

Ein herkömmlicher Basisdieselkraftstoff weist eine Cetan-Zahl von 48 auf. Diesem Kraftstoff wird ein Additiv bestehend aus 55 Gew.% TBHP und 45 Gew.% tert-Butanol in einer Konzentration basierend auf TBHP von 0,05 Gew.% Additivmenge sowie in einer Konzentration von 0,5 Gew.% zugesetzt.A conventional base diesel fuel has a cetane number of 48. An additive consisting of 55% by weight of TBHP and 45% by weight of tert-butanol in a concentration based on TBHP of 0.05% by weight of additive and in a concentration of 0.5% by weight is added to this fuel.

Im Vergleich zum Basiskraftstoff wird durch Zugabe des Additives die Cetan-Zahl signifikant erhöht. Bei Verwendung der drei genannten Kraftstoffe, also Basisdiesel, Basisdiesel + 0,05 Gew.% TBHP sowie Basisdiesel + 0,5 Gew. % TBHP, wird ohne deutliche Verbrauchssteigerung bei gleicher Motorleistung in Gegenwart des Additivs TBHP die Cetan-Zahl signifikant verbessert und zugleich die Schadstoffemission signifikant verringert. Insbesondere findet eine deutliche Verringerung des Kohlenwasserstoffausstoßes sowie des Kohlenmonoxidausstoßes statt.Compared to the basic fuel, the addition of the additive significantly increases the cetane number. When using the three fuels mentioned, ie base diesel, base diesel + 0.05 wt.% TBHP and base diesel + 0.5 wt.% TBHP, the cetane number is significantly improved and at the same time without significant increase in consumption at the same engine power in the presence of the additive TBHP the emission of pollutants is significantly reduced. In particular, there is a significant reduction in hydrocarbon emissions and carbon monoxide emissions.

Beispiel 2Example 2 Kraftstoff, umfassend TBHP als AdditivFuel, comprising TBHP as an additive

Einem herkömmlichen Basisdieselkraftstoff wird ein Additiv bestehen aus 28 Gew.% TBHP, 23 Gew.% TBA und 49 Gew.% DTBP in einer Konzentration basierend auf TBHP von 0,05 Gew.% sowie in einer Konzentration von 0,05 Gew.% zugesetzt.To a conventional base diesel fuel is added an additive consisting of 28 wt% TBHP, 23 wt% TBA and 49 wt% DTBP in a concentration based on TBHP of 0.05 wt% and in a concentration of 0.05 wt% ,

Im Vergleich zum Basiskraftstoff wird durch Zugabe des Additives die Cetan-Zahl signifikant erhöht. Bei Verwendung der drei genannten Kraftstoffe, also Basisdiesel, Basisdiesel + 0,05 Gew.% TBHP sowie Basisdiesel + 0,5 Gew. % TBHP, wird ohne deutliche Verbrauchssteigerung bei gleicher Motorleistung in Gegenwart des Additivs TBHP die Cetan-Zahl signifikant verbessert und zugleich die Schadstoffemission signifikant verringert. Insbesondere findet eine deutliche Verringerung des Kohlenwasserstoffausstoßes sowie des Kohlenmonoxidausstoßes statt.Compared to the basic fuel, the addition of the additive significantly increases the cetane number. When using the three fuels mentioned, ie base diesel, base diesel + 0.05 wt.% TBHP and base diesel + 0.5 wt.% TBHP, is without significant increase in consumption at the same Engine performance in the presence of the additive TBHP significantly improves the cetane number and at the same time significantly reduces pollutant emissions. In particular, there is a significant reduction in hydrocarbon emissions and carbon monoxide emissions.

Claims (12)

Kraftstoff, umfassend tert.-Butylhydroperoxid (TBHP) als Additiv.Fuel comprising tertiary butyl hydroperoxide (TBHP) as an additive. Kraftstoff, umfassend TBHP als Additiv nach Anspruch 1,
dadurch gekennzeichnet, dass
das Additiv wasserfreies TBHP enthält.A fuel comprising TBHP as an additive according to claim 1,
characterized in that
the additive contains anhydrous TBHP. Kraftstoff, umfassend TBHP als Additiv nach Anspruch 1 oder 2,
dadurch gekennzeichnet, dass
das Additiv TBHP in einem organischen Lösungsmittel enthält.A fuel comprising TBHP as an additive according to claim 1 or 2,
characterized in that
contains the additive TBHP in an organic solvent. Kraftstoff, umfassend TBHP als Additiv nach einem der vorhergehenden Ansprüche,
dadurch gekennzeichnet, dass
das Additiv TBHP in tert-Butanol enthält.A fuel comprising TBHP as an additive according to any one of the preceding claims,
characterized in that
contains the additive TBHP in tert-butanol. Kraftstoff, umfassend TBHP als Additiv nach einem der vorhergehenden Ansprüche,
dadurch gekennzeichnet, dass
das Additiv aus 30 bis 70 Gew.% TBHP in 70 bis 30 Gew.% organischem Lösungsmittel besteht.A fuel comprising TBHP as an additive according to any one of the preceding claims,
characterized in that
the additive consists of 30 to 70 wt.% TBHP in 70 to 30 wt.% Organic solvent. Kraftstoff, umfassend TBHP als Additiv nach einem der vorhergehenden Ansprüche,
dadurch gekennzeichnet, dass
das TBHP in einer Menge von 0,001 Gew.% bis 10 Gew.%, bezogen auf das Gesamtgewicht des Kraftstoffs, vorliegt.A fuel comprising TBHP as an additive according to any one of the preceding claims,
characterized in that
the TBHP is present in an amount of from 0.001% to 10% by weight, based on the total weight of the fuel. Kraftstoff, umfassend TBHP als Additiv,
dadurch gekennzeichnet, dass der Basiskraftstoff ausgewählt ist aus Dieselkraftstoff, Ottokraftstoff und Raps-Methylester.Fuel comprising TBHP as an additive,
characterized in that the base fuel is selected from diesel fuel, gasoline and rapeseed methyl ester. Kraftstoff, umfassend TBHP als Additiv nach einem der vorhergehenden Ansprüche,
dadurch gekennzeichnet, dass
der Kraftstoff ausgewählt ist aus Dieselkraftstoff.A fuel comprising TBHP as an additive according to any one of the preceding claims,
characterized in that
the fuel is selected from diesel fuel. Kraftstoff, umfassend TBHP als Additiv nach einem der vorhergehenden Ansprüche,
dadurch gekennzeichnet, dass
der Kraftstoff ein weiteres Additiv, insbesondere Ditertbutylperoxid, umfasst.A fuel comprising TBHP as an additive according to any one of the preceding claims,
characterized in that
the fuel comprises a further additive, in particular di-tert-butyl peroxide. Kraftstoffadditiv, umfassend TBHP.Fuel additive comprising TBHP. Kraftstoffadditiv, umfassend TBHP nach Anspruch 9,
dadurch gekennzeichnet, dass
es wasserfreies TBHP umfasst.A fuel additive comprising TBHP according to claim 9,
characterized in that
it includes anhydrous TBHP. Verwendung von TBHP zur Erhöhung der Cetan-Zahl.Use of TBHP to increase the cetane number.
EP11189416.8A 2011-11-16 2011-11-16 Tertiobutyl hydroperoxide (TBHP) as a diesel additive Ceased EP2594623A1 (en)

Priority Applications (9)

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EP11189416.8A EP2594623A1 (en) 2011-11-16 2011-11-16 Tertiobutyl hydroperoxide (TBHP) as a diesel additive
MX2014005821A MX2014005821A (en) 2011-11-16 2012-11-16 Tert-butyl hydroperoxide (tbhp) as a diesel additive.
US14/358,831 US9303224B2 (en) 2011-11-16 2012-11-16 Tert-butyl hydroperoxide (TBHP) as a diesel additive
ES12784622T ES2864214T3 (en) 2011-11-16 2012-11-16 Tert-butyl hydroperoxide (TBHP) as additive for diesel
EP12784622.8A EP2780435B1 (en) 2011-11-16 2012-11-16 Tertiobutyl hydroperoxide (tbhp) as a diesel additive
PCT/EP2012/072877 WO2013072478A1 (en) 2011-11-16 2012-11-16 Tert-butyl hydroperoxide (tbhp) as a diesel additive
CN201280056319.5A CN103998582B (en) 2011-11-16 2012-11-16 As the TBHP of diesel fuel additives
ZA2014/03247A ZA201403247B (en) 2011-11-16 2014-05-06 Tert-butyl hydroperoxide (tbhp) as a diesel additive
IN1024/KOLNP/2014A IN2014KN01024A (en) 2011-11-16 2014-05-15 Tert butyl hydroperoxide (tbhp) as a diesel additive

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