WO2009060057A2 - Éther en tant qu'agent potentialisant pour des biocides - Google Patents

Éther en tant qu'agent potentialisant pour des biocides Download PDF

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Publication number
WO2009060057A2
WO2009060057A2 PCT/EP2008/065110 EP2008065110W WO2009060057A2 WO 2009060057 A2 WO2009060057 A2 WO 2009060057A2 EP 2008065110 W EP2008065110 W EP 2008065110W WO 2009060057 A2 WO2009060057 A2 WO 2009060057A2
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WIPO (PCT)
Prior art keywords
ether
use according
water
hydrocarbons
alkyl
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PCT/EP2008/065110
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German (de)
English (en)
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WO2009060057A3 (fr
Inventor
Claudius Kormann
Uwe Rebholz
Matthias Kiefer
Dietmar Posselt
Irene Trötsch-Schaller
Erich K. Fehr
Original Assignee
Basf Se
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Application filed by Basf Se filed Critical Basf Se
Priority to EP08846809A priority Critical patent/EP2217061A2/fr
Publication of WO2009060057A2 publication Critical patent/WO2009060057A2/fr
Publication of WO2009060057A3 publication Critical patent/WO2009060057A3/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • A—HUMAN NECESSITIES
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    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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Definitions

  • the present invention relates to the use of certain ethers as effect enhancers for water-soluble biocides in nonpolar hydrocarbons. Moreover, the invention relates to the use of at least one water-soluble biocide in combination with at least one of these ethers for controlling microorganisms and / or for reducing or preventing the multiplication of microorganisms in hydrocarbons, which are substantially immiscible with water. Further objects of the invention are additive compositions and hydrocarbon compositions comprising such ethers and biocides, and also a method for controlling microorganisms and / or for reducing or preventing the multiplication of microorganisms in hydrocarbons, wherein the hydrocarbon with at least one such biocide and added with at least one such ether.
  • hydrocarbons especially of petroleum and petroleum fractions (eg naphtha), fuel oils (eg diesel fuels, heating oil, turbine fuels, biodiesel), lubricants or solvents
  • fuel oils eg diesel fuels, heating oil, turbine fuels, biodiesel
  • lubricants or solvents it may cause problems due to microbial processes come.
  • microorganisms can grow, their growth being accelerated by the presence of water.
  • Hydrocarbons often have a boundary layer to water, such as when stored in large storage tanks, eg. In ships, airplanes or stationary tanks. The water comes either from the hydrocarbons themselves or penetrates by condensation of humidity.
  • hydrocarbons are only very slightly or not miscible with water and usually have a lower density than water, the water migrates to the tank bottom, where it becomes a hotbed for microorganisms that use and decompose the hydrocarbon as a food source.
  • the hydrocarbon is pumped or agitated in some form, the microorganisms can be dispersed in it.
  • cholera pathogens were found in the ballast water of ship tanks and also the propagation of the zebra mussel (Dreissena polymorpha) in North America is attributed to this distribution path. Furthermore, it is problematic that certain anaerobic bacteria reduce sulfates to sulfur-containing acids, which leads to corrosion problems. To prevent these problems, hydrocarbons stored in large tanks (between) have been added to biocides for some time. Both water-soluble and oil-soluble biocides are known.
  • biocides have good biocidal activity, good biodegradability and are also inexpensive. Their disadvantage, however, is that they are not or only partially soluble in nonpolar hydrocarbons, such as petroleum, petroleum fractions and fuel oils, and therefore form their own phase. Of course, after phase separation, they can no longer develop biocidal activity in the hydrocarbon.
  • oil-soluble biocides are readily soluble in non-polar hydrocarbons, they remain distributed over the long term. However, their biodegradability is usually not good, they often contain unwanted elements such as halogens, phosphorus or sulfur, and they are also not cheap.
  • R 1 -OR 2 wherein R 1 is C 1 -C 6 alkyl; R 2 is C 1 -C 6 -alkyl or a radical of the formula - (AO) n -R 3 ; wherein
  • A is linear or branched C 2 -C 4 -alkylene which is optionally substituted by 1 or 2 radicals OR 3 ;
  • R 3 is H or C 1 -C 6 alkyl; and
  • n is 1, 2, 3 or 4;
  • the ethers defined above are used as effect enhancers for water-soluble biocides in nonpolar hydrocarbons.
  • Another object of the invention is the use of (i) at least one biocide with a logarithm of the distribution coefficient in n-octanol / water log P ow of less than 4; in combination with (ii) at least one ether of the formula
  • R 1 is C 1 -C 6 alkyl
  • R 2 is C 1 -C 6 -alkyl or a radical of the formula - (AO) n -R 3 ; wherein
  • A is linear or branched C 2 -C 4 -alkylene which is optionally substituted by 1 or 2 radicals OR 3 ;
  • R 3 is H or C 1 -C 6 alkyl; and
  • n is 1, 2, 3 or 4;
  • microorganisms for controlling microorganisms and / or for reducing or preventing the proliferation and / or growth of microorganisms in hydrocarbons which are substantially immiscible with water.
  • “In combination with” means that on the one hand the at least one biocide and the at least one ether of the formula R 1 -OR 2 can be used as a physical mixture. However, this is not mandatory; Thus, biocide and ether can be used in physically separate form, wherein the time interval of the use of the two component (i) and (ii) of course must be designed so that a common effect is even possible. What is a suitable time interval depends on the individual case. Thus, the hydrocarbon may, if it does not come into contact with water over a longer period of time contain only the at least one ether. Only when the hydrocarbon comes into contact with water, the biocide must be added within a period of, for example, at most 10 days or at most 5 days or at most 2 days. Preferably, however, "in combination with” means that the at least one biocide and the at least one ether are used in the mixture. Accordingly, a preferred aspect of the invention relates to the use of a mixture comprising
  • hydrocarbons in which the biocide and the ether are used according to the invention are hydrocarbons which are substantially immiscible with water.
  • “Substantially immiscible with water” in the context of the present invention means that at most 10 g of water, preferably at most 5 g of water and in particular at most 2 g of water per 100 g of hydrocarbon are soluble in it, ie there is no phase separation.
  • Hydrocarbons that are substantially immiscible with water are regularly non-polar and have a relative dielectric constant (at 0 0 C) ⁇ r of at most 10, preferably at most 5 particularly at most 3.
  • biocides are compounds which inhibit or prevent the growth and / or proliferation of microorganisms or kill the microorganisms.
  • Microorganisms are microscopically small organisms with their own metabolism (with the exception of viruses), which are generally not recognizable as single individuals with the naked eye. Their size is very different. Most microorganisms are protozoa. Examples of microorganisms are bacteria, many fungi (eg, yeasts, molds, slime molds and other harmful fungi), microscopic algae and
  • Viruses are also counted among the microorganisms in the context of the present invention.
  • the logarithm of the partition coefficient in an n-octanol / water mixture log P ow is a measure of the water solubility or oil solubility of a compound.
  • Water soluble is a substance that has a log P ow of less than 4.
  • the logarithm of the partition coefficient in n-octanol / water is determined at 25 ° C. according to the method described in OECD Guideline 107 (preferably with the shake-flask method), to which reference is hereby fully made.
  • Ci-C4-alkyl is a linear or branched alkyl radical having 1 to 4 carbon atoms.
  • Ci-C ⁇ -alkyl is a linear or branched alkyl radical having 1 to 6 carbon atoms. Examples include, in addition to the previously mentioned for Ci-C 4 -AlkVl Res- pentyl, hexyl and the position isomers thereof.
  • Linear or branched C 2 -C 4 -alkylene is a linear or branched alkylene radical having 2, 3 or 4 carbon atoms. Examples are -CH 2 CH 2 -, -CH (CH 3 ) -, -CH 2 CH 2 CH 2 -, -CH (CH 3 ) CH 2 -, -CH 2 CH (CH 3 ) -, -C (CHs ) 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH (CH 3 ) CH 2 CH 2 -, -CH 2 CH 2 CH (CH 3 ) -, -C (CH 3 ) 2 CH 2 - and -CH 2 C (CHs) 2 -.
  • C 2 -C 4 alkylene which is substituted by 1 or 2 radicals OR 3
  • Examples are the abovementioned examples of C 2 -C 4 alkylene in which 1 or 2 H atoms have been replaced by a radical OR 3 .
  • preference is given to C 3 -alkylene which is substituted by a group OR 3 or C 4 -alkylene which is substituted by 1 or 2 groups OR 3 , where the group OR 3 may not be bonded to a carbon atom, which is already bound to an oxygen atom.
  • C 2 -C 4 -alkylene which is substituted by 1 or 2 radicals OR 3 are accordingly -CH 2 CH (OR 3 ) CH 2 -, -CH (CH 2 OR 3 ) CH 2 -, - CH 2 CH (CH 2 OR 3 ) -, -C (CH 3 ) (CH 2 OR 3 ) -, -CH 2 CH (OR 3 ) CH 2 CH 2 -, -CH 2 CH 2 CH (OR 3 ) CH 2 -, -CH (CH 3 ) CH (OR 3 ) CH 2 -, -CH (CH 3 ) CH (OR 3 ) CH 2 -, -CH (CH 2 OR 3 ) CH 2 CH 2 -, -CH 2 CH 2 CH (CH 2 OR 3 ) -, -C (CH 3 ) (CH 2 OR 3 ) CH 2 -, -CH 2 C (CH 3 ) (CH 2 OR 3 ) -, -CH 2 CH (OR 3 ) CH (OR 3 ) CH 2 -
  • Suitable biocides are all common biocides that meet the above-defined criterion of water solubility (log P ow ⁇ 4).
  • Examples include aldehydes and formaldehyde derivatives, such as formaldehyde itself, ethanedial (glyoxal), pentanedial (glutaraldehyde) or benzene-1, 2-dicarboxaldehyde, urea derivatives, such as chlorotoluron or N, N
  • dimethyl-N'-3- (trifluoromethyl) -phenyl-urea bis-guanidines such as chlorhexidine or PHMB (poly (hexamethylenebis-guanidine) hexane, benzoic acid derivatives such as methyl paraben (4-hydroxybenzoic acid methyl ester) or 2-aminobenzoic acid methyl ester, aliphatic carboxylic acids such as octanoic acid, peracids and Peroxides, such as peracetic acid and hydrogen peroxide, phenol derivatives, such as 2-phenoxyethanol, oxazolidines, such as 3,3'-methylenebis [5-methyloxazolidine] or 3,3'-methylenebis [oxazolidine], isothiazolones, such as 4,5- Dichloro-2-octyl-3- (2H) -isothiazolone, morpholines, such as 4,4'- Methylenebis [morpholine], quaternary ammoni
  • the biocides used according to the invention preferably contain no chlorine. Accordingly, preferred biocides are the above biocides, except those containing chlorine such as chlorotoluron, chlorhexidine, 4,5-dichloro-2-octyl-3- (2H) -isothiazolone, benzalkonium chloride, cetylpyridinium chloride and benzethonium chloride. With particular preference the biocides used according to the invention contain no halogen.
  • biocides are the abovementioned biocides, with the exception of those containing halogen, such as chlorotoluron, N, N-dimethyl-N'-3- (trifluoromethyl) -phenyl-urea, chlorhexidine, 4,5-dichloro 2-octyl-3- (2H) -isothiazolone, benzalkonium chloride, cetylpyridinium chloride and benzethonium chloride.
  • halogen such as chlorotoluron, N, N-dimethyl-N'-3- (trifluoromethyl) -phenyl-urea, chlorhexidine, 4,5-dichloro 2-octyl-3- (2H) -isothiazolone, benzalkonium chloride, cetylpyridinium chloride and benzethonium chloride.
  • biocides used according to the invention are preferably selected from biocides which are described in Commission Regulation (EC) No. 1048/2005 of 13 June
  • biocides which do not contain chlorine ie the compounds listed above with the exception of 4,5-dichloro-2-octyl-3- (2H) -isothiazolone and chlorotoluron.
  • biocides which do not contain halogen ie the compounds listed above with the exception of 4,5-dichloro-2-octyl-3- (2H) -isothiazolone, chlorotoluron and N, N-dimethyl-N'-3 - (trifluoromethyl) -phenyl-urea.
  • biocides which have a log P ow of less than 2. These include 3,3'-methylenebis [5-methyloxazolidine], 3,3'-methylenebis [oxazolidine], 4,4'-methylenebis [morpholine], ethanedial (glyoxal), pentanedial (glutaric aldehyde), benzene 1, 2 dicarboxaldehyde, 2-aminobenzoic acid methyl ester, peracetic acid, 2-phenoxyethanol, ethanol, n-propanol and 1,3,5-triazine-1,3,5- (2H, 4H, 6H) -triethanol.
  • biocides having a log P ow of less than zero include 3,3'-methylenebis [5-methyloxazolidine], 3,3'-methylenebis [oxazolidine], 4,4'-methylenebis [morpholine], ethanedial, pentanedial (glutaraldehyde), peracetic acid, ethanol, and 1, 3.5 Triazine-1, 3,5- (2H, 4H, 6H) -triethanol.
  • biocides are those which release an aldehyde, in particular formaldehyde. These include ethanedial (glyoxal), pentandial (glutaric dehyd), benzene-1,2-dicarboxaldehyde and 1,3,5-triazine-1,3,5- (2H, 4H, 6H) -triethanol. Of these, aldehyde-releasing biocides with a log P ow of less than 0 are preferred. These include ethanedial (glyoxal), pentanedial (glutaric aldehyde) and 1,3,5-triazine-1, 3,5- (2H, 4H, 6H) -triethanol. Aldehyde-releasing compounds not only act biocidal, but also act as sulfur or hydrogen sulfide scavengers, which positively counteracts the corrosive action of sulfate-reducing anaerobic bacteria.
  • biocide used is 1, 3,5-triazine-1, 3,5- (2H, 4H, 6H) -triethanol (1,3,5-tris [2-hydroxyethyl] -1,3,5-hexahydrotriazine) ,
  • R 1 is preferably C 1 -C 4 -alkyl.
  • R 2 is preferably C 1 -C 4 -alkyl or a radical of the formula - (AO) n -R 3 , where A is linear or branched C 2 -C 4 -alkylene which is optionally substituted by 1 or 2 radicals OR 3 ;
  • R 3 is H or C 1 -C 4 -alkyl; and n is 1, 2, 3 or 4.
  • the ethers are preferably selected from methyl tert-butyl ether, ethyl tert-butyl ether, glycerol monomethyl ether, glycerol monoethyl ether, glycerol dimethyl ether, glycerol diethyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono- n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol mono-n-propyl ether and triethylene glycol mono-n-butyl ether.
  • R 2 particularly preferably represents a radical of the formula - (AO) n -R 3 'in which A, n and R 3 have the general or preferred meanings mentioned above or below.
  • A is preferably 1,2-ethylene.
  • n is preferably 1 or 2.
  • R 3 is preferably H or C 1 -C 4 -alkyl.
  • ethers are the mono-C 1 -C 4 -alkyl ethers of ethylene glycol, diethylene glycol and triethylene glycol, such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono n-propyl ether , Diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol mono-n-propyl ether and triethylene glycol.
  • ethylene glycol monomethyl ether such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoe
  • glycol mono-n-butyl ether More preferred are the monomethyl ethers of ethylene glycol, diethylene glycol and triethylene glycol, ie ethylene glycol monomethyl ether, diethylene glycol monomethyl ether and triethylene glycol monomethyl ether.
  • diethylene glycol monomethyl ether (DEGME; 2- (2-methoxyethoxy) ethanol) is used as the ether.
  • the problem of contamination of hydrocarbons with microorganisms occurs, as already shown, in particular when the hydrocarbons have a contact surface with water. Accordingly, the use according to the invention has particular advantages when the hydrocarbon is brought into contact with water before it is added to its final use, so that it can even lead to any appreciable contamination with microorganisms.
  • the amount of water is not very important; since the water passes predominantly through condensation processes in the hydrocarbon, the amount is usually not very large and depends on the respective storage and transport conditions for the hydrocarbon.
  • the hydrocarbons are selected from fuel oils, lubricants, and organic solvents that are substantially immiscible with water.
  • fuel oils are understood as meaning liquid fuels and liquid fuels. Suitable fuel oils are gasolines and middle distillates. Middle distillates are preferably selected from diesel fuels, heating oil and turbine fuels.
  • the heating oils for example, low-sulfur or sulfur-rich mineral oil raffinates or stone or brown coal distillates, which typically have a boiling range of 150 to 400 0 C.
  • the heating oils are preferably low-sulfur heating oils, for example those having a sulfur content of at most 0.1% by weight, preferably of at most 0.05% by weight, more preferably of at most 0.005% by weight, and in particular of at most 0.001% by weight.
  • heating oil is especially called heating oil for domestic oil firing systems or fuel oil EL.
  • the quality requirements for such heating oils are specified, for example, in DIN 51-603-1 (cf., also Ullmann's Encyclopedia of Industrial Chemistry, 5th edition, Vol. A12, pp. 617 et seq., To which reference is expressly made).
  • the diesel fuels are, for example, crude oil raffinates which chrine have customarily a boiling range of 100 to 400 0 C. These are mostly distillates with a 95% point up to 360 0 C or even beyond. However, these may also be so-called "ultra low sulfur diesel” or "city diesel", characterized by a NEN 95% point of, for example, a maximum of 345 0 C and a maximum sulfur content of 0.005 wt .-% or by a 95% point of, for example 285 0 C and a maximum sulfur content of 0.001 wt .-%.
  • diesel fuels available through refining (petroleum)
  • renewable diesel fuels synthetic diesel fuels and blends of all these types of diesel fuel are also included in the concept of diesel fuels.
  • Synthetic fuels are generally petrol and diesel fuels, which are obtained by the Fischer-Tropsch process from various primary energy sources.
  • the primary energy source is first converted to synthesis gas, which is then further reacted catalytically to the desired fuel type.
  • the type of litigation determines whether synthetic diesel fuels or synthetic gasoline fuels are obtained. If one uses coal as the primary energy source, one speaks of a CTL fuel (CTL: coal-to-liquid); If natural gas is used, the end product is called GTL fuel (GTL: gas to liquid). Biomass is the starting material, it is a BTL fuel (BTL: biomass-to-liquid).
  • Renewable fuels are fuels that are produced from renewable raw materials, especially from plants. These include vegetable oils, biodiesel, bioethanol and also the already mentioned BTL fuels. Bioethanol is mainly used in gasoline engines and thus does not belong to the regenerative diesel fuels, but is counted among the renewable gasoline fuels. Biodiesel is generally understood to mean the lower alkyl esters of vegetable oils (or animal fats), d. H. their C 1 -C 4 -alkyl esters, in particular their ethyl or methyl esters and especially their methyl esters. In Europe, the most widely used biodiesel is rapeseed oil methyl ester (RME).
  • RME rapeseed oil methyl ester
  • Biodiesel is obtained by the transesterification of vegetable oils, which mainly consist of glycerol esters of long-chain fatty acids, with lower alcohols (C 1 -C 4 -alcohols), in particular with methanol, but sometimes also with ethanol.
  • vegetable oils which mainly consist of glycerol esters of long-chain fatty acids, with lower alcohols (C 1 -C 4 -alcohols), in particular with methanol, but sometimes also with ethanol.
  • Preferred diesel fuels are diesel fuels obtained by refining, synthetic diesel fuels such as GTL, CTL and BTL diesel fuels, vegetable oils, biodiesel, and mixtures of these diesel fuel types.
  • Particularly preferred diesel fuels are biodiesel and biodiesel blends, i. H. Blends of biodiesel with various different diesel fuels, such as diesel fuels obtained by refining, synthetic diesel fuels, such as GTL, CTL and BTL diesel fuels, and vegetable oils, blends of biodiesel with diesel fuels obtained by refining being preferred.
  • Jet A Jet A-1
  • Jet B JP-4, JP-5, JP-7, JP-8 and JP-8 + 100.
  • Jet A and Jet A-1 are commercially available kerosene based turbine fuel specifications. The associated standards are ASTM D 1655 and DEF STAN 91-91. Jet A and Jet A-1 have their specification maximum freezing point of -40 0 C and -47 0 C. Jet B is a more cut fuel based on naphtha and kerosene fractions. JP-4 is equivalent to Jet B.
  • JP 4, JP-5, JP-7, JP-8 and JP-8 + 100 are military turbine fuels, such as those used by the Navy and Air Force. In part, these names refer to formulations which already contain additives, such as corrosion inhibitors, anti-icing agents, static dissipators, etc.
  • Preferred turbine fuels are Jet A, Jet A-1 and JP 8.
  • the gasoline has an aromatic content of a maximum of 60, such as. B. a maximum of 42 or a maximum of 35 vol .-% and / or a maximum sulfur content of 2000, such as. B. maximum 150 or maximum 10 ppm by weight.
  • the aromatic content of the gasoline is 10 to 50, z. B. 30 to 42 vol .-%, in particular 32 to 40 vol .-%, or at most 35 vol .-%.
  • the sulfur content of the gasoline is 2 to 500, z. B. 5 to 100 ppm by weight, or at most 10 ppm by weight.
  • the gasoline has an olefin content of up to 50% by volume, e.g. B. from 6 to 21 vol .-%, in particular 7 to 18 vol .-%.
  • the gasoline has a benzene content of up to 5 vol .-%, such as. B. 0.5 to 1, 0 vol .-%, in particular 0.6 to 0.9 VoI.-%.
  • the gasoline has an oxygen content of up to 25 wt .-%, z. B. up to 10 wt .-% or 1, 0 to 2.7 wt .-%, in particular from 1, 2 to 2.0 wt .-%, on.
  • gasoline fuels can be exemplified, which at the same time have an aromatics content of at most 38% by volume, preferably of at most 35% by volume, an olefin content of not more than 21% by volume, a sulfur content of max. times 50 or 10 ppm by weight, have a benzene content of not more than 1, 0 vol .-% and an oxygen content of 1, 0 to 2.7 wt .-%.
  • the content of alcohols and ethers in gasoline can vary over a wide range. Examples of typical maximum contents are 15% by volume for ethanol, 65% by volume for ethanol, 20% by volume for isopropanol, 15% by volume for tert-butanol, 20% by volume for isobutanol and 20% by weight for isobutanol Ether having 5 or more C atoms in the molecule (eg, methyl tert-butyl ether or ethyl tert-butyl ether) 30% by volume.
  • the alcohols can also be regenerative fuels, for example bioethanol.
  • the summer vapor pressure of the gasoline is usually not more than 70 kPa, in particular 60 kPa (each at 37 0 C).
  • the ROZ of petrol is usually 75 to 105.
  • a common range for the corresponding MOZ is 65 to 95.
  • the gasoline fuels can be both fuels for petrol engines in passenger cars and aviation fuel (leaded petrol with an RON of 100 to 130).
  • Lubricants serve as a release agent between two relatively moving friction partners.
  • the task of the lubricants is to prevent the direct contact between them and thereby reduce wear on the one hand and on the other to reduce friction or to optimize.
  • the lubricant can cool (i.e., dissipate frictional heat), seal the friction point, keep abrasive particles away from the friction partners and other components, prevent corrosion, or reduce running noise.
  • the most economically important lubricants are engine oils, transmission oils such as manual and automatic transmission oils and lubricating greases. In the context of the present application, however, only liquid lubricants, in particular engine oils and gear oils, are relevant.
  • Motor oils usually consist of mineral base oils, which contain predominantly paraffinic constituents and are prepared by complex work-up and purification processes in the refinery, with a proportion of about 2 to 10% by weight of additives (based on the active substance contents).
  • mineral base oils which contain predominantly paraffinic constituents and are prepared by complex work-up and purification processes in the refinery, with a proportion of about 2 to 10% by weight of additives (based on the active substance contents).
  • additives based on the active substance contents.
  • gear oils such as shift and auto oils, are similar in composition to their base components and additives as engine oils.
  • solvents which are substantially immiscible with water
  • examples of such solvents are aliphatic hydrocarbons, e.g. Alkanes such as pentane, hexane, heptane and octane, or alkenes such as hexene, cycloaliphatic hydrocarbons such as cyclohexane and cyclooctane, aromatic hydrocarbons such as benzene, toluene and the xylene, and halogenated hydrocarbons such as chloroform, carbon tetrachloride, chlorobenzene and the like ,
  • the biocides and ethers used according to the invention are used according to the invention in hydrocarbons which are selected from fuel oils.
  • Preferred fuel oils are middle distillates.
  • Preferred middle distillates are diesel fuel and heating oil.
  • Preferred diesel fuels are refinery-obtainable diesel fuels, synthetic diesel fuels, and regenerative diesel fuels, as well as mixtures thereof.
  • the regenerative diesel fuels are preferably biodiesel.
  • Particularly preferred diesel fuels are biodiesel and biodiesel blends, i. H.
  • Blends of biodiesel with various different diesel fuels such as diesel fuels obtained by refining, synthetic diesel fuels, such as GTL, CTL and BTL diesel fuels, and vegetable oils, blends of biodiesel with diesel fuels, which are obtained by refining preferred are.
  • the at least one biocide and the at least one ether are even more preferred in a weight ratio of preferably from 100: 1 to 1: 100, more preferably from 20: 1 to 1:99, more preferably from 2: 1 to 1:90 from 1: 1 to 1:90, especially 1: 1 to 1:50, especially from 1: 1 to 1:20 and even more particularly 1: 5 to 1: 20 used in the invention.
  • the use of the at least one biocide in combination with the at least one ether for controlling microorganisms and / or for reducing or preventing the multiplication of microorganisms in hydrocarbons is usually carried out by admixing the hydrocarbon with the at least one biocide and the at least one ether.
  • the invention thus also provides a method for controlling microorganisms and / or for reducing or preventing the multiplication of microorganisms. in hydrocarbons, in which the hydrocarbon is treated with at least one biocide as defined above and at least one ether as defined above.
  • the at least one biocide and the at least one ether are added to the hydrocarbon in a total amount of preferably 10 to 5000 ppm by weight, e.g. B. from 50 to 5000 ppm by weight, more preferably 10 to 3000 ppm by weight, for. From 50 to 3000 ppm by weight, more preferably from 10 to 2000 ppm by weight, e.g. B. from 50 to 2000 ppm by weight, and in particular from 10 to 1000 ppm by weight, for. B. from 50 to 1000 ppm by weight added.
  • the most appropriate for the individual hydrocarbon type total amount of biocide and ether depends on its nature, more specifically on its tendency to be populated with microorganisms from, and can be determined by the skilled person, for example by simple preliminary experiments. For example, regenerative fuels have a higher tendency to attract microorganisms, so they require a higher dosage.
  • biodiesel the at least one biocide and the at least one ether in a total amount of preferably 100 to 5000 ppm by weight, e.g. B. from 500 to 5000 ppm by weight, more preferably 100 to 3000 ppm by weight, z. From 500 to 3000 ppm by weight, and more preferably from 100 to 2000 ppm by weight, e.g. B. from 500 to 2000 ppm by weight, add.
  • the at least one biocide and the at least an ether in a total amount of preferably 10 to 3000 ppm by weight, e.g. B. from 50 to 3000 ppm by weight, more preferably 10 to 2000 ppm by weight, for. From 50 to 2000 ppm by weight, more preferably from 10 to 1000 ppm by weight, e.g. From 50 to 1000 ppm by weight, even more preferably from 10 to 500 ppm, e.g. B.
  • a further subject of the invention is an additive composition containing (i) at least one biocide as defined above; and (ii) at least one ether as defined above; and optionally at least one further fuel additive or at least one further lubricant additive and / or a carrier.
  • biocide as defined above
  • ether as defined above
  • optionally at least one further fuel additive or at least one further lubricant additive and / or a carrier optionally at least one further fuel additive or at least one further lubricant additive and / or a carrier.
  • the weight ratio of component (i) to component (ii) is preferably 2: 1 to 1:90, more preferably 1: 1 to 1:90, more preferably from 1: 1 to 1:50, in particular from 1: 1 to 1 : 20 and especially 1: 5 to 1:20.
  • the additive composition according to the invention optionally contains at least one fuel additive (it is then a fuel additive composition) and / or a carrier.
  • Suitable fuel additives are, for example, detergent additives, ashless dispersants, cold flow improvers, demulsifiers, dehazers, carrier oils, cetane number improvers, metal deactivators, corrosion inhibitors, antioxidants, lubricity improvers, defoamers, antistatic agents, stabilizers, color markers, fragrances and the like, and mixtures thereof.
  • Kerocom® PIBSI BASF Aktiengesellschaft
  • Dispersant FOA 528 (Octel OY);
  • Demulsifier T-9318 (Petrolite);
  • Keromet® MD 100 BASF Aktiengesellschaft
  • Corrosion inhibitors Additin® RC4801 (Rhein Chemie GmbH); Kerocorr® 3232
  • Lubricity improver Kerocorr® LA 99C (BASF Aktiengesellschaft);
  • Defoamer TEGO® 2079 (Goldschmidt); Antistatic agents: Stadis® 450 (Octel);
  • Stabilizers Keropon® ES 3500 (BASF Aktiengesellschaft); FOA 528A (Octel OY);
  • Suitable carrier oils are fractions obtained in petroleum processing, such as bright stock or base oils with viscosities, for example from the class Solvent Neutral (SN) 500-2000; but also aromatic hydrocarbons, paraffinic hydrocarbons and alkoxyalkanols. It is also useful as a "hydrocrack oil” known and obtained in the refining of mineral oil fraction (Vakuumdestillatites with a boiling range of about 360 to 500 0 C, available from high pressure catalytically hydrogenated and isomerized and dewaxed natural mineral oil). Also suitable are mixtures of the abovementioned mineral carrier oils.
  • Examples of synthetic carrier oils which can be used according to the invention are selected from polyolefins (polyalphaolefins or polyinternalolefins), (poly) esters, (poly) alkoxylates, polyethers, aliphatic polyetheramines, alkylphenol-initiated polyethers, alkylphenol-initiated polyetheramines and carboxylic acid esters of long-chain alkanols.
  • Suitable carrier oils are described, for example, in WO 2006/100083, to which reference is hereby fully made.
  • synthetic carrier oils are used.
  • Preferred synthetic carrier oils are alkanol alkoxylates, in particular alkanol propoxylates or alkanol butoxylates.
  • diluents are used as "vehicles" in fuel additive compositions.
  • Suitable diluents are, for example, aromatic and aliphatic hydrocarbons, such as benzene, toluene, the xylene, solvent naphtha, alkanols having 3 to 10 carbon atoms, eg. Example, propanol, isopropanol, n-butanol, sec-butanol, isobutanol, 2-ethylhexanol, propylheptanol and the like, optionally in combination with hydrocarbon solvents, and alkoxyalkanols.
  • the additive composition according to the invention optionally contains at least one lubricant additive (it is then a lubricant additive composition) and / or at least one carrier.
  • Sulfur compounds e.g. B. reaction products of terpenes ( ⁇ -pinene), resin oils or low molecular weight polybutenes with sulfur, dialkyl sulfides, dialkyl trisulfides, polysulfides, diaryl sulfides, modified thiols, mercaptobenzimidazoles, Mercaptotriazines, thiophene derivatives, xanthates, zinc dialkyldithiocarbamates, thioglycols, thioaldehydes, dibenzyl disulfide, alkylphenol sulfides, dialkylphenol sulfides or sulfur-containing carboxylic acids
  • Phosphorus compounds e.g. As triaryl and Trialkylphosphite, 3,5-di-tert-butyl-4-hydroxy-benzyl-phosphonic acid dialkyl ester or phosphonic acid piperazides
  • Sulfur-phosphorus compounds e.g., zinc dialkyldithiophosphates (metal dialkyl dithiophosphates also act as corrosion inhibitors and high pressure additives in lubricating oils) or reaction products of phosphorus pentasulfide with terpenes ( ⁇ -pinene, dipentene), polybutenes, olefins or unsaturated esters
  • Phenol derivatives e.g. As sterically hindered mono-, bis- or trisphenols, sterically hindered polynuclear phenols, polyalkylphenols, 2,6-di-tert-butyl-4-methyl-phenol or methylene-4,4 '-bis (2,6-di tert-butylphenol) (Phenol derivatives are often used in combination with sulfur-based or amine-based antioxidants)
  • Metal deactivators in the strict sense for.
  • N-salicylidene-ethylamine N, N'-disali- cylidene-ethylenediamine
  • N, N'-disalicylidene-1 2-propanediamine
  • triethylenediamine ethylenediaminetetraacetic acid
  • phosphoric acid citric acid
  • glycolic acid Leci- thin, thiadiazole
  • Viscosity Index Improver 0.05 to 10%
  • polyisobutenes having a molecular weight of usually 10,000 to 45,000
  • polymethacrylates having a molecular weight of usually 15,000 to 100,000
  • homo- and copolymers of 1,3-dienes such as butadiene or isoprene having a molecular weight of usually 80,000 to 100,000
  • 1, 3 Diene-styrene copolymers having a molecular weight of usually 80,000 to 100,000
  • maleic anhydride-styrene polymers in esterified form having a molecular weight of usually 60,000 to 120,000
  • star-shaped polymers having a block structure by units of conjugated dienes and aromatic monomers having a molecular weight from usually 200,000 to 500,000
  • polyalkylstyrenes having a molecular weight of usually 80,000 to 150,000
  • polyolefins of ethylene and propylene or styrene-cyclopentadiene-nor
  • pour point depressants (0.03 to 1%), e.g. B. bicyclic aromatics such as naphthalene with various long-chain alkyl radicals, poly methyacrylates having 12 to 18 carbon atoms in the alcohol radical, a degree of branching between 10 to 30 mol% and an average molecular weight of 5,000 to 500,000, long-chain alkylphenols and dialkyl phthalates or copolymers of different olefins
  • detergents 0.2 to 4%
  • e.g. calcium, lead, zinc and manganese naphthenates, calcium dichloro stearates, calcium phenyl stearates, calcium chlorophenyl stearates, sulfonation of alkyl aromatics such as dodecyl benzene, petroleum sulfonates, sodium, calcium, barium or magnesium Sulfonates, neutral, basic and overbased sulfonates, phenates and carboxylates,
  • Salicylates metal salts of alkylphenols and alkylphenol sulfides, phosphates, thiophosphates or alkenylphosphonic acid derivatives
  • Ashless dispersants 0.5 to 10%
  • Ashless dispersants e.g. Mannich condensates of alkylphenol, formaldehyde and polyalkylenepolyamines, reaction products of polyisobutenylsuccinic anhydrides with polyhydroxy compounds or polyamines, copolymers of alkyl methacrylates with diethylaminoethyl methacrylate, N-vinylpyrrolidone, N-vinylpryridine or 2-hydroxyethyl methacrylate or vinylacetone.
  • Extreme Pressure Additives 0.2 to 2.5%), e.g. Chlorinated paraffins with 40 to 70% by weight chlorine content, chlorinated fatty acid (especially with trichloromethyl end groups), dialkyl hydrogen phosphites, triaryl phosphites, aryl phosphates such as tricresyl phosphate, dialkyl phosphates, trialkyl phosphates such as tributyl phosphate, trialkyl phosphines, diphosphoric acid esters,
  • Nitroaromatics aminophenol derivatives of naphthenic acid, carbamic acid esters, dithiocarbamic acid derivatives, substituted 1,2,3-triazoles, mixtures of benzotriazole and alkylsuccinic anhydride or alkylmaleic anhydride, 1, 2,4-thiadiazole polymers, morpholinobenzothiadiazole disulfide, chlorinated Alkyl sulfides, sulfurized olefins, sulfurized chloronaphthalenes, chlorinated alkyl thiocarbonates, organic sulfides and polysulfides such as bis (4-chlorobenzyl) disulfide and tetrachlorodiphenylsulfide, trichloracrolein-mercaptals or in particular zinc dialkyldithiophosphates (ZDDP)
  • friction modifiers 0.05 to 1%
  • polar oil-soluble compounds which produce a thin layer on the friction surface by adsorption
  • fatty alcohols e.g. As fatty alcohols, fatty amides, fatty acid salts, fatty acid alkyl esters or fatty acid glycerides
  • antifoam additives 0.0001 to 0.2%), e.g. As liquid silicones such as polydimethylsiloxanes or Polhethylenglykolether and sulfides (i) demulsifiers (0.1 to 1%), e.g. B. Dinonylnaphthalinsulfonate in the form of their alkali and alkaline earth metal salts
  • corrosion inhibitors also referred to as metal deactivators
  • metal deactivators e.g. B. tertiary amines and their salts, imino esters, amidoximes, diaminomethanes, derivatives of saturated or unsaturated fatty acids with alkanolamines, alkylamines, sarcosines, imidazolines, alkylbenzotriazoles, Dimercaptothiadiazol- Derviate, diaryl phosphates, thiophosphoric acid esters, neutral salts of primary n-C8-Ci8- Alkylamines or cycloalkylamines with dialkyl phosphates having branched C 5 -C 12 -alkyl groups, neutral or basic alkaline earth metal sulfonates,
  • (k) emulsifiers (0.01 to 1%), e.g. Long-chain unsaturated, naturally occurring carboxylic acid, naphthenic acids, synthetic carboxylic acids, sulfonamides, N-oleylsarcosine, alkanesulfamidoacetic acid, dodecylbenzenesulfonate, long-chain alkylated ammonium salts such as dimethyldodecylbenzylammonium chloride, imidazolium salts, alkyl, alkylaryl, acyl, alkylamino and acylaminopolyglycols or long-chain acylated mono- and diethanolamines
  • emulsifiers e.g. Long-chain unsaturated, naturally occurring carboxylic acid, naphthenic acids, synthetic carboxylic acids, sulfonamides, N-oleylsarcosine, alkanesulfamidoacetic acid, dodecylbenz
  • Another object of the invention is a hydrocarbon composition
  • a hydrocarbon composition comprising a major weight fraction of a hydrocarbon which is substantially immiscible with water, and a minor proportion by weight of at least one biocide as defined above and at least one ether as defined above.
  • Preferred hydrocarbons are also selected here from fuel oils, lubricants and water-immiscible solvents and in particular from fuel oils and lubricants.
  • Preferred fuel oils are middle distillates and gasoline fuels, with middle distillates being more preferred.
  • middle distillates are diesel fuels, heating oils and turbine fuels, with diesel fuels and heating oils being more preferred.
  • diesel fuels both refining and synthetic and regenerative diesel fuels and their mixtures are suitable.
  • the hydrocarbon composition contains the at least one biocide and the at least one ether in a total amount of preferably 10 to 5000 ppm by weight, e.g. B. from 50 to 5000 ppm by weight, more preferably 10 to 3000 ppm by weight, for. From 50 to 3000 ppm by weight, more preferably from 10 to 2000 ppm by weight, e.g. B. from 50 to 2000 ppm by weight, and in particular from 10 to 1000 ppm by weight, for. B. from 50 to 1000 ppm by weight.
  • the hydrocarbon composition may also contain at least one additional additive.
  • the hydrocarbon composition when the hydrocarbon composition is a fuel oil composition (fuel composition), it may contain any one of the aforementioned fuel additives in any conventional amounts. If it is a lubricant composition, it may contain one of the aforementioned lubricant additives in customary amounts.
  • the hydrocarbon composition of the present invention contains the hydrocarbon in an amount of preferably at least 98% by weight, more preferably at least 99% by weight, and in the case of gasolines in particular at least 99.5% by weight based on the total weight of the hydrocarbon composition.
  • B7 biodiesel blend A biodiesel blend of 7 parts by weight of RME and 93 parts by weight of mineral diesel (ie from refining) (“B7 biodiesel blend") was tested.
  • microorganisms used were isolates from diesel fuel samples. These were propagated / grown on commercial media, harvested and washed. In order to minimize the moisture input, the biomass was obtained by centrifugation as water-poor as possible and then weighed and applied.
  • Moistened B7 biodiesel blend (in each case 100 ml, each batch was additionally added 150 ppm of water) was charged in eight 250 ml tubes with about 50 mg of microbial biomass and incubated at 20 0 C for 4 weeks.
  • four vessels still contained 284 ppm of a mixture of 10% by weight of 1,3,5-triazine-1,3,5- (2H, 4H, 6H) -triethanol and 90% by weight % DEGME, while the remaining four vessels contained only 100 ml of B7 biodiesel blend and 150 ppm (control).
  • the vessels were first examined for optical changes.
  • the biomass was then determined gravimetrically by filtering the entire batch volume after vigorous shaking through a 0.45 ⁇ m pore membrane filter.
  • the filter residue was washed several times with rinse solution. Thereafter, the filter material was dried on nonwoven fabric, introduced into a defined and dried vessel with physiological saline solution and strongly vorvor text. After removal of the filter, the reweighing was carried out to determine the biomass formed in the four weeks.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
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Abstract

L'invention concerne l'utilisation de certains éthers en tant qu'agent potentialisant pour des biocides solubles dans l'eau, dans des hydrocarbures apolaires. L'invention concerne également l'utilisation d'un biocide soluble dans l'eau en combinaison avec au moins un de ces éthers pour la lutte contre des micro-organismes et/ou la réduction ou la suppression de la prolifération de micro-organismes dans des hydrocarbures essentiellement non-miscibles avec l'eau. L'invention concerne également des compositions d'additifs et des compositions d'hydrocarbures contenant de tels éthers et biocides, ainsi qu'un procédé de lutte contre des micro-organismes et/ou de réduction ou de suppression de la prolifération de micro-organismes dans des hydrocarbures, consistant à faire réagir un hydrocarbure avec au moins un tel biocide et au moins un tel éther.
PCT/EP2008/065110 2007-11-09 2008-11-07 Éther en tant qu'agent potentialisant pour des biocides WO2009060057A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08846809A EP2217061A2 (fr) 2007-11-09 2008-11-07 Éther en tant qu'agent potentialisant pour des biocides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07120397 2007-11-09
EP07120397.0 2007-11-09

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WO2009060057A2 true WO2009060057A2 (fr) 2009-05-14
WO2009060057A3 WO2009060057A3 (fr) 2009-06-25

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011006734A2 (fr) 2009-07-13 2011-01-20 L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Mélange d’additifs bactéricides et anticorrosifs pour carburants
US8313541B2 (en) 2009-04-07 2012-11-20 Basf Se Mixture of polar oil-soluble nitrogen compounds and oil-soluble aliphatic compounds for lowering the cloud point in middle distillate fuels
DE102012203003A1 (de) 2012-02-28 2013-08-29 Schülke & Mayr GmbH Flüssige Zubereitung für die Reduktion von freiem Sauerstoff und die Konservierung von Wasser
US20150033617A1 (en) * 2011-12-21 2015-02-05 Total Marketing Services Additive compositions for improving the lacquering resistance of higher grade fuels of the diesel or biodiesel type
EP4092099A1 (fr) 2021-05-20 2022-11-23 TUNAP GmbH & Co. KG Additif bioactif pour un carburant et ses utilisations, composition de carburant et procédé

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DE19961621C2 (de) * 1999-12-13 2002-11-14 Schuelke & Mayr Gmbh Bakterizide und fungizide flüssige Zubereitungen für technische Produkte

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US3915970A (en) * 1972-03-24 1975-10-28 Coalite Chem Prod Ltd Hexahydro-1,3,5-triazines
EP1531174A2 (fr) * 2003-11-04 2005-05-18 Afton Chemical Corporation Composition et Procédé pour diminuer la quantité de péroxydes dans des combustibles de distillats moyens contenant des composés oxygénés.

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8313541B2 (en) 2009-04-07 2012-11-20 Basf Se Mixture of polar oil-soluble nitrogen compounds and oil-soluble aliphatic compounds for lowering the cloud point in middle distillate fuels
WO2011006734A2 (fr) 2009-07-13 2011-01-20 L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Mélange d’additifs bactéricides et anticorrosifs pour carburants
DE102009033161A1 (de) 2009-07-13 2011-01-27 Schülke & Mayr GmbH Additivgemsich für die bakterizide und Korrosionsschutzausrüstung von Treib- und Brennstoffen
US20150033617A1 (en) * 2011-12-21 2015-02-05 Total Marketing Services Additive compositions for improving the lacquering resistance of higher grade fuels of the diesel or biodiesel type
DE102012203003A1 (de) 2012-02-28 2013-08-29 Schülke & Mayr GmbH Flüssige Zubereitung für die Reduktion von freiem Sauerstoff und die Konservierung von Wasser
WO2013127584A1 (fr) 2012-02-28 2013-09-06 L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Préparation liquide pour la réduction de l'oxygène libre et la préservation d'eau
US10836658B2 (en) 2012-02-28 2020-11-17 Vink Chemicals Gmbh & Co. Kg Liquid preparation for the reduction of free oxygen and the preservation of water
EP4092099A1 (fr) 2021-05-20 2022-11-23 TUNAP GmbH & Co. KG Additif bioactif pour un carburant et ses utilisations, composition de carburant et procédé

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WO2009060057A3 (fr) 2009-06-25

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