JP2011508011A - Corrosion resistance and improved control of microorganisms in hydrocarbonaceous compositions - Google Patents

Abstract

Formula (I) (wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ are as defined herein) for use in hydrocarbonaceous compositions (eg petroleum or liquid fuels) Additives for The additive improves the corrosion resistance of the composition, and also improves microbial resistance when the composition is biodiesel. The additive further improves the microbial resistance of any added biocide contained in such compositions.

Description

The present invention relates to additives for hydrocarbonaceous compositions. More particularly, the present invention relates to amino alcohol additives that improve the corrosion properties and microbial resistance of hydrocarbonaceous compositions (eg petroleum and fuel). Aminoalcohol additives also improve the effectiveness of biocides typically used in such compositions.

BACKGROUND OF THE INVENTION Hydrocarbonaceous compositions such as petroleum (crude oil) and fuels almost always contain moisture. As atmospheric moisture is condensed, additional water can accumulate in the tank. Moisture accumulates in the diesel tank, for example, as condensate droplets on exposed tank surfaces, as dissolved water in the fuel, and as the bottom of the fuel. As with oil, water can condense and accumulate in the pipeline. Alcohol / fuel mixtures, such as “gasohol”, tend to absorb and retain a higher concentration of water than alcohol-free petroleum fuels. In addition, more recently it has begun to intentionally incorporate water into the fuel for environmental benefits. It has been found that nitrogen oxides, hydrocarbons and particulate emissions produced by internal combustion engines, particularly diesel engines (those employing water-fuel emulsions), can be lower. Reduction of passenger emissions is treated as an administrative and environmental business and is expected to increase the use of aqueous hydrocarbon fuel emulsions.

  However, the presence of water in the hydrocarbonaceous composition can cause problems either by intentional introduction (eg, emulsified fuel) or condensation (eg, in storage or transport containers). Because microorganisms rely on water for survival, water in hydrocarbonaceous compositions can cause microbial contamination. Microorganisms depend on organic molecules in their compositions for nutrition and growth. As a result, some species attack the composition directly and grow consuming hydrocarbon and non-hydrocarbon components.

  Fuel biodegradation in support of microbial growth is a direct cause of fuel contamination. Color, combustion heat, pour point, cloud point, thermal stability, cleaning properties, and anti-corrosion properties change negatively as microorganisms selectively attack fuel components. In addition to loss of additive and fuel performance, as bacteria and fungi grow, they form biomass, which accumulates at the fuel: water interface on the tank surface and on the filter. In the case of crude oil, microbiologically affected corrosion can occur in the pipeline as a result of sulfate-reducing bacteria (SRB) activity and growth.

  Corrosion problems can also be affected by the presence of water and acids in the hydrocarbonaceous composition. Biodiesel fuels in particular contain free fatty acids, and petroleum derived fuels typically contain naphthenic acid residues and sulfur, which can react with water vapor to form sulfuric acid during combustion. Although removal of sulfur and acid from the fuel is possible, this introduces additional process costs for the fuel manufacturer. In addition, phosphoric acid and carboxylic acid based lubricants are intentionally added to some fuels (eg, fuel emulsions) to improve performance. In crude oil, in addition to microbiologically affected corrosion, the presence of dissolved carbon dioxide (carbonic acid) and / or hydrogen sulfide can also lead to corrosion problems.

  In view of the above, there is a need in the art for additives that help limit corrosion and / or microbial growth in hydrocarbonaceous compositions.

BRIEF SUMMARY OF THE INVENTION The present invention comprises: a hydrocarbonaceous composition; and formula (I):

(Wherein R ¹ , R ² , R ³ , R ⁴ , and R ⁵ are as defined below)
A blend of amino alcohols.

  The present invention also provides a blend comprising a hydrocarbonaceous composition, an amino alcohol of formula (I), and a biocide.

  The present invention further provides a method of imparting microbial resistance to a biodiesel fuel, comprising including an effective amount of an amino alcohol of formula (I) in the biodiesel fuel.

FIG. 1 is a chart showing the synergistic effect in diesel fuel of 3-amino-4-octanol and biocide FUELSAVER ^™ . FIG. 2 is a chart showing the synergistic effect in diesel fuel of 3-amino-4-octanol and biocide Kathon ^™ FP. FIG. 3 is a chart showing the synergistic effect in diesel fuel of 3-amino-4-octanol and biocide BIOBAN ^™ BIT 20 DPG.

  In one aspect, the present invention provides amino alcohol additives for hydrocarbonaceous compositions. “Hydrocarbonaceous composition” means petroleum (crude oil) or liquid fuel (eg, gasoline, diesel, biodiesel, water-fuel emulsion, ethanol fuel, and ether fuel). Preferred fuels include those containing high levels of acid, such as biodiesel.

  Additives inhibit corrosion of systems in contact with the hydrocarbonaceous composition, such as storage tanks, pipelines and engines. The improved corrosion resistance is believed to be due in part to the ability of the amino alcohol to control the pH of the composition.

  In addition to improved corrosion stability, it has surprisingly been found that amino alcohols of formula (I) increase the microbial resistance of biodiesel when used in biodiesel fuel. This is true even if the biodiesel fuel does not contain added biocidal compounds.

（式中：
Ｒ¹およびＲ³は、各々独立にＨ、直鎖もしくは分岐鎖のアルキル、アルケニル、アルキニル、シクロアルキルもしくはアリール（好ましくはフェニル）であり、または、Ｒ¹、Ｒ³およびこれらが付いている炭素がシクロアルキル環を形成し、
Ｒ²およびＲ⁴は、各々独立にＨまたはアルキルであり、Ｒ²およびＲ⁴が共に２個以下の炭素原子を含有することを条件とし、そして
Ｒ⁵は、不存在であるかまたはＣ₁−Ｃ₁₀のアルキレン（架橋性アルキル）、アリーレン（好ましくはフェニル）、アリーレン−アルキレン−もしくは−アルキレン−アリーレン−（例えばベンジル、フェネチル等）である。）
のアミノアルコール化合物であり、式（Ｉ）のアミノアルコールは、少なくとも５個の炭素原子を含有し、そしてＲ¹、Ｒ³およびＲ⁵のアルキル、シクロアルキル、アルキレン、アリール、およびアリーレン基は、任意にアルキルまたはフェニルで置換されている。 The additive of the present invention has the formula (I):

(Where:
R ¹ and R ³ are each independently H, linear or branched alkyl, alkenyl, alkynyl, cycloalkyl or aryl (preferably phenyl), or R ¹ , R ³ and the carbon to which they are attached. Forms a cycloalkyl ring,
R ² and R ⁴ are each independently H or alkyl, provided that both R ² and R ⁴ contain no more than 2 carbon atoms, and R ⁵ is absent or C ₁ alkylene -C ₁₀ (crosslinkable alkyl), arylene (preferably phenyl), arylene - alkylene - or - alkylene - arylene - a (e.g. benzyl, phenethyl). )
Wherein the amino alcohol of formula (I) contains at least 5 carbon atoms and the alkyl, cycloalkyl, alkylene, aryl, and arylene groups of R ¹ , R ^3, and R ⁵ are Optionally substituted with alkyl or phenyl.

Preferred amino alcohols of formula I include compounds of formula I-1, which are compounds of formula I, wherein R ¹ is C ₁ -C ₆ alkyl, more preferably linear or branched propyl, butyl. , Pentyl or hexyl, and particularly preferably n-butyl.

Preferred aminoalcohols of formula I and I-1 include compounds of formula I-2, which are compounds of formula I or I-1 where R ² is H, methyl or ethyl. .

Preferred amino alcohols of formula I, I-1 and I-2 also include compounds of formula I-3, which are compounds of formula I, I-1 or I-2, wherein R ³ is hydrogen and R ⁴ are those is hydrogen.

Preferred amino alcohols of formula I, I-1, I-2 and I-3 further include compounds of formula I-4, which are compounds of formula I, I-1, I-2 or I-3 Where R ⁵ is a bond or is a methylene bridge or an ethylene bridge.

  Further preferred amino alcohols of the formula (I) are those of the formula (II):

(Where:
R ¹ is C ₂ -C ₆ alkyl; and R ² and R ⁴ are each independently H or C ₁ -C ₂ alkyl, and both R ² and R ⁴ contain no more than 2 carbon atoms. On the condition. )
The compound of this is mentioned.

  Particularly preferred primary amino alcohols for use in the present invention include: 2-amino-3-hexanol, 2-amino-2-methyl-3-hexanol, 3-amino-4-octanol, 2-amino-2- Examples include methyl-3-heptanol, 2-amino-4-ethyl-3-octanol, 2-amino-3-heptanol, 2-amino-1-phenylbutanol, and mixtures thereof. Particularly preferred is 3-amino-4-octanol.

  The amino alcohol compounds of the present invention can be readily prepared using techniques well known in the art by those of ordinary skill in the art. For example, such compounds can be prepared by forming a nitroalcohol by reaction of a nitroalkane with an aldehyde and then catalytic hydrogenation of the nitro group to an amine. A more detailed description of an exemplary amino alcohol synthesis is given in the examples.

  Amino alcohol can be used in the form of an acid salt. Suitable salts include, but are not limited to, boric acid, lactic acid, pelargonic acid, nonanoic acid, neodecanoic acid, sebacic acid, azelaic acid, citric acid, benzoic acid, undecylenic acid, lauric acid, myristic acid , Stearic acid, oleic acid, tall oil fatty acid, ethylenediaminetetraacetic acid and similar materials.

  Aminoalcohols are generally used in hydrocarbonaceous compositions at concentrations sufficient to provide corrosion stability and / or increase microbial resistance (in the latter case when used with biodiesel). The amount necessary to provide these beneficial effects can be readily determined by one of ordinary skill in the art with the usual capabilities. As an example, generally from about 0.001 to about 5 weight percent, more preferably from about 0.001 to about 2 weight percent (based on the total weight of the composition) is used.

  Amino alcohols can also be used in combination with other primary, secondary and tertiary amino alcohols and even other corrosion inhibitors. The hydrocarbonaceous composition can contain other optional additives. For example, when the composition is a fuel, typical additives include, but are not limited to, lubricants, cetane enhancers, combustion accelerators, antioxidants / thermal stabilizers, and / or cleaning / deposition control additives. Can be mentioned.

  In addition to the improved corrosion stability and microbial resistance described above, it has also been found that primary amino alcohols of formula I synergistically improve the activity of biocides in hydrocarbonaceous compositions. Thus, the combination of aminoalcohol and biocide provides more effective and longer lasting microbial control at reduced biocide concentrations than would be expected when the biocide was used alone.

  Thus, according to a second aspect, the present invention provides a blend comprising a hydrocarbonaceous composition, an amino alcohol of formula I and a biocide. This aspect of the invention is particularly for compositions containing water (whether water is intentionally added (eg, fuel emulsion) or not) that is characteristic of most oils and fuels as described above. Applicable. Such compositions typically contain at least 0.01% water and no more than about 50%.

  Preferred hydrocarbonaceous compositions for this second aspect of the invention include petroleum and liquid fuels. Preferred liquid fuels include gasoline, diesel, biodiesel, water-fuel emulsion, ethanol fuel, and ether fuel. More preferred liquid fuels include gasoline, diesel, water-fuel emulsion, ethanol fuel, and ether fuel. A particularly preferred liquid fuel for this aspect is diesel fuel. As illustrated by the examples, the amino alcohol of formula I is itself non-biocidal in diesel fuel. Thus, the discovery that they can synergistically improve the effectiveness of biocidal compounds in diesel is surprising.

  Any biocide that is compatible with the hydrocarbonaceous composition can be utilized in the blends of the present invention. Preferred biocides are: triazines such as 1,3,5-tris- (2-hydroxyethyl) -s-triazine and trimethyl-1,3,5-triazine-1,3,5-triethanol, examples being GROTAN (from Troy Corporation), iodopropynyl butyl carbamate, eg POLYPHASE (supplied by Troy Corporation), 1,2-benzisothiazolin-3-one, eg BIOBAN BIT (sold by The Dow Chemical Company), 4,4-dimethyloxazolidine , As examples BIOBAN CS-1135 (from The Dow Chemical Company), 7-ethyl-bicyclooxazolidine, BIOBAN CS-1246 as The Dow Chemical Co. A combination of 4- (2-nitrobutyl) -morpholine and 4,4 '-(2-ethyl-2-nitrotrimethylene) dimorpholine, The Dow Chemical Co. as FUELSAVER. 2-methyl-4-isothiazolin-3-one, a combination of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one, such as the KATHON brand ( Rohm & Haas Corporation), 2-bromo-2-nitro-1,3-propanediol, octylisothiazolinone, dichloro-octylisothiazolinone, dibromo-octylisothiazolinone, phenols such as o-phenylphenol and p-chloro-m-cresol) and its corresponding sodium and / or potassium salts, sodium pyrithione, zinc pyrithione, n-butylbenzisothiazolinone, 1- (3-chloroallyl) -3,5,7-triaza-1 -Azonia Adamant Chloride, chlorothalonil, carbendazim, diiodomethyltolylsulfone, 2,2-dibromo-3-nitrilopropionamide (DBNPA), glutaraldehyde, N, N′-methylene-bis-morpholine, ethylenedioxymethanol (eg, Troyshield B7 ), Phenoxyethanol (eg Comtram 121), tetramethylol acetylenediurea (eg Protectol TD), dithiocarbamate, 2,6-dimethyl-m-dioxane-4-ol acetate (eg Bioban DXN), dimethylol-dimethyl-hydantoin, tris ( Hydroxymethyl) nitromethane, bicyclic oxazolidine (eg Nuospet 95), (thiocyanomethylthio) -benzothiazole (TCM B), methylene bis (thiocyanate) (MBT), substituted dioxaborinanes such as BIOBOR JF (from Hammonds Fuel Additives), tetrakis (hydroxymethyl) phosphonium sulfate (THPS), such as AQUACAR THPS 75 (from The Dow Chemical Company) Ammonium compounds such as alkyldimethylbenzylammonium chloride (ADBAC), cocodiamine, dazomet such as Protectol DZ (from BASF), and mixtures of two or more thereof.

Further preferred biocides are combinations of 4- (2-nitrobutyl) -morpholine and 4,4 ′-(2-ethyl-2-nitrotrimethylene) dimorpholine, particularly when the hydrocarbonaceous composition is a liquid fuel. (Available from The Dow Chemical Company as FUELSAVER ^™ ), a combination of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one (CMIT / MIT), ( A combination of thiocyanomethylthio) -benzothiazole (TCMTB) and methylenebis (thiocyanate) (MBT), substituted dioxaborinane, and mixtures of two or more thereof.

  Further preferred biocides include glutaraldehyde, 2-bromo-2-nitro-1,3-propanediol, isothiazolinones, such as BIT and CMIT / MIT, 2,2, especially when the hydrocarbonaceous composition is petroleum. -Dibromo-3-nitrilopropionamide (DBNPA), tetrakis (hydroxymethyl) phosphonium sulfate (THPS), oxazolidine such as 4,4-dimethyloxazolidine and 7-ethylbicyclooxazolidine, quaternary ammonium compounds such as alkyldimethylbenzylammonium And chloride (ADBAC), cocodiamine, dazomet, and mixtures of two or more thereof.

  In the present invention, the biocide (or combination of biocides) is preferably present in the blend at a concentration of about 0.001-2 weight percent (based on the total weight of the blend). However, it is preferred to use low concentrations of biocides to reduce costs and minimize the potential for adverse environmental effects. In fact, by increasing the effectiveness of the biocide, the amino alcohol described herein allows the use of less biocide than can be achieved without the amino alcohol. One.

  The concentration of the formula I aminoalcohol to biocide in the blend is not critical, but in some preferred embodiments corresponds to a mass ratio of aminoalcohol to biocide of about 5000: 1 to about 1: 2. In a more preferred embodiment, the mass ratio of amino alcohol to biocide is about 100: 1 to 1: 2. In an even more preferred embodiment, the mass ratio is about 60: 1 to 1: 1.

Preferred fuel-based blends according to the present invention are:
(A) liquid fuel;
(B) an amino alcohol of the above formula (I); and (c) a mixture of (i) 4- (2-nitrobutyl) -morpholine and 4,4 ′-(2-ethyl-2-nitrotrimethylene) dimorpholine. (From FUELSAVER ^™ , from The Dow Chemical Company);
(Ii) a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one;
(Iii) a mixture of (thiocyanomethylthio) -benzothiazole (TCMTB) and methylenebis (thiocyanate) (MBT); and (iv) a substituted dioxaborinane;
A biocide selected from the group consisting of:
including.

（式中：
Ｒ¹はＣ₂−Ｃ₆アルキルであり；そして
Ｒ²およびＲ⁴は、各々独立にＨまたはＣ₁−Ｃ₂アルキルであり、Ｒ²およびＲ⁴が共に２個以下の炭素原子を含有することを条件とする。）；ならびに
（ｃ）（ｉ）４−（２−ニトロブチル）−モルホリンと４，４’−（２−エチル−２−ニトロトリメチレン）ジモルホリンとの混合物；
（ｉｉ）５−クロロ−２−メチル−４−イソチアゾリン−３−オンと２−メチル−４−イソチアゾリン−３−オンとの混合物；
（ｉｉｉ）（チオシアノメチルチオ）−ベンゾチアゾールとメチレンビス（チオシアネート）との混合物；および
（ｉｖ）置換ジオキサボリナン；
からなる群から選択される殺生物剤；
を含む。 In this embodiment, the mass ratio of amino alcohol to biocide (i) is preferably about 30: 1 to 1: 1, more preferably about 25: 1 to 1.5: 1. Furthermore, the mass ratio of amino alcohol to biocide (ii) is preferably about 70: 1 to 3: 1. More preferred fuel-based blends according to the present invention are:
(A) liquid fuel;
(B) an amino alcohol of formula (II);

(Where:
R ¹ is C ₂ -C ₆ alkyl; and R ² and R ⁴ are each independently H or C ₁ -C ₂ alkyl, and both R ² and R ⁴ contain no more than 2 carbon atoms. On the condition. And (c) (i) a mixture of 4- (2-nitrobutyl) -morpholine and 4,4 ′-(2-ethyl-2-nitrotrimethylene) dimorpholine;
(Ii) a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one;
(Iii) (thiocyanomethylthio) -benzothiazole and methylenebis (thiocyanate) mixture; and (iv) substituted dioxaborinane;
A biocide selected from the group consisting of:
including.

  In this embodiment, the mass ratio of amino alcohol to biocide (i) is preferably about 30: 1 to 1: 1, more preferably about 25: 1 to 1.5: 1. Furthermore, the mass ratio of amino alcohol to biocide (ii) is preferably about 70: 1 to 3: 1.

Particularly preferred fuel-based blends according to the invention are:
(A) liquid fuel;
(B) 3-amino-4-octanol; and (c) (i) a mixture of 4- (2-nitrobutyl) -morpholine and 4,4 ′-(2-ethyl-2-nitrotrimethylene) dimorpholine;
(Ii) a mixture of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one;
(Iii) (thiocyanomethylthio) -benzothiazole and methylenebis (thiocyanate) mixture; and (iv) substituted dioxaborinane;
A biocide selected from the group consisting of:
including.

  In this embodiment, the mass ratio of amino alcohol to biocide (i) is preferably about 30: 1 to 1: 1, more preferably about 25: 1 to 1.5: 1. Furthermore, the mass ratio of amino alcohol to biocide (ii) is preferably about 70: 1 to 3: 1.

Preferred petroleum blends according to the present invention are:
(A) petroleum;
(B) an amino alcohol of formula (I) as defined above; and (c) glutaraldehyde, 2-bromo-2-nitro-1,3-propanediol, tetrakis (hydroxymethyl) phosphonium sulfate (THPS) A biocide selected from the group consisting of 2, 2-dibromo-3-nitrilopropionamide (DBNPA), isothiazolinone compounds, quaternary ammonium compounds, cocodiamine, and dazomet;
including.

More preferred petroleum blends according to the invention are:
(A) petroleum;
(B) an amino alcohol of formula (II) as defined above; and (c) glutaraldehyde, 2-bromo-2-nitro-1,3-propanediol, tetrakis (hydroxymethyl) phosphonium sulfate (THPS) A biocide selected from the group consisting of 2, 2-dibromo-3-nitrilopropionamide (DBNPA), isothiazolinone compounds, quaternary ammonium compounds, cocodiamine, and dazomet;
including.

Particularly preferred petroleum blends according to the invention are:
(A) petroleum;
(B) 3-amino-4-octanol; and (c) glutaraldehyde, 2-bromo-2-nitro-1,3-propanediol, tetrakis (hydroxymethyl) phosphonium sulfate (THPS), 2,2-dibromo A biocide selected from the group consisting of -3-nitrilopropionamide (DBNPA), isothiazolinone compounds, quaternary ammonium compounds, cocodiamine, and dazomet;
including.

  As used herein, “alkyl” covers straight and branched chain aliphatic groups having 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms. Preferred alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl and hexyl.

  The term “alkenyl” as used herein refers to an unsaturated straight or branched chain fatty acid having one or more carbon-carbon double bonds having 2 to 8 carbon atoms, and preferably 2 to 6 carbon atoms. Means a group. Preferred alkenyl groups include, without limitation, ethenyl, propenyl, butenyl, pentenyl, and hexenyl.

  As used herein, the term “alkynyl” refers to an unsaturated straight or branched aliphatic group having one or more carbon-carbon triple bonds having 2 to 8 carbon atoms, and preferably 2 to 6 carbon atoms. Means group. Preferred alkynyl groups include, without limitation, ethynyl, propynyl, butynyl, pentynyl, and hexynyl.

  An “alkylene” group is an alkyl as defined above and has a connecting role located between two other chemical groups. Preferred alkylene groups include but are not limited to methylene, ethylene, propylene, and butylene.

  As used herein, the term “cycloalkyl” includes saturated and partially unsaturated cyclic hydrocarbon groups having 3 to 12 carbons, preferably 3 to 8 carbons, and more preferably 3 to 7 carbons. . Preferred cycloalkyl groups include, without limitation, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cycloheptyl, and cyclooctyl.

An “aryl” group is a C ₆ -C ₁₂ aromatic moiety containing 1 to 3 aromatic rings. Preferably, the aryl group is a C ₆ -C ₁₀ aryl group. Preferred aryl groups include, without limitation, phenyl, naphthyl, anthracenyl, and fluorenyl. More preferred is phenyl.

  Alkyl, cycloalkyl, and aryl (and their crosslinkable derivatives alkylene, cycloalkylene, and arylene) are optionally substituted with one or more other alkyls (eg, methyl, ethyl, butyl), phenyl, or both ing. When substituted, the number of carbons in the substituent is counted in the 6-12 carbons of the compound.

  The following examples are illustrative of the invention but are not intended to limit its scope.

Examples Example 1: Preparation of 3-amino-4-octanol Preparation of 3-nitro-4-octanol from 1-nitropropane and valeraldehyde. A sample of 3-nitro-4-octanol was prepared by adding 1-nitropropane (1-NP, 300 g, 3.37 mol) to a 1 liter three-necked round bottom flask (RBF, 24/40, 29/42, 24/40). Synthesize by adding in (with thermocouple, magnetic stirrer, 500 ml addition funnel, nitrogen inlet, and glass stopper). The pale yellow liquid is diluted by adding methanol (MeOH, 150 g). As a result, endotherm is generated. Add caustic catalyst (16 g of 10% aqueous solution and 0.60 g of 50% aqueous caustic solution, 1.9 g total, 1.4 mol%). This changes the reaction color to orange and produces a slight exotherm. Valeraldehyde (258 g, 3.00 mol, 0.89 equiv) is added to the addition funnel and slowly added to 1-NP over 3 hours. The heat of reaction raises the temperature to 40-45 ° C. When the addition of valeraldehyde is complete, the contents of RBF are transferred into a 1 liter glass bottle, purged with nitrogen, and stored at ambient temperature. The progress of the reaction is monitored by gas chromatography. After 2 weeks, the conversion has reached 84 area% and the reaction is stopped by the addition of 10% aqueous hydrochloric acid solution (19 ml). The resulting pH = 1 solution is concentrated in vacuo (50 ° C./full vacuum / 0.5 hours) to remove solvent and residual reagents. The resulting olive green solution (491 g, 95 area% corrected purity, 89% yield) is filtered (0.5 micron), purged with nitrogen, and stored in the refrigerator until needed.

  Catalytic hydrogenation of 3-nitro-4-octanol to 3-amino-4-octanol alkanolamine. A sample of 3-amino-4-octanol (3A4O) is synthesized by reduction of 3-nitro-4-octanol with Parr Autoclave unit. Grace 3201 Raney Nickel (RaNi, 90 g wet, 45 g dry, 10 wt%) and methanol (MeOH, 300 g) are placed in a stainless steel, 2 liter autoclave. The autoclave is sealed, assembled, purged with nitrogen, then hydrogen, pressurized with hydrogen (600 psig), stirred at 600 RPM, and warmed to 40 ° C. Nitro-alcohol (491 g) is diluted with absolute ethanol (EtOH, 150 g) and pumped (4 ml / min) into the autoclave. The addition is complete after 3.5 hours and the completion of the reaction is judged after 4 hours (as no hydrogen uptake is observed). Cool the autoclave, stop agitation, vent and purge with nitrogen. The autoclave is broken down and the contents are vacuum filtered to remove the RaNi catalyst. This results in the isolation of a pale yellow liquid (92 area%) which is concentrated in vacuo (55 ° C./full vacuum) before the product is overhead collected (57-62 ° C./full vacuum). This resulted in the isolation of a clear, colorless semi-solid (344 g, 95.3 area%, 75% overall yield) which contained some oxazolidine (2.2 area%) and some 2 Contains secondary amine (0.5 area%).

Example 2: Preparation of 2-amino-3-heptanol Preparation of 2-nitro-3-heptanol from nitroethane (NE) and valeraldehyde. In a manner similar to Example 1, a sample of 2-nitro-3-heptanol was prepared from nitroethane (NE, 275 g, 3.67 mol) in a 1 liter 3-neck round bottom flask (RBF, 24/40, 29/42, 24 / 40) Synthesize by adding in (with thermocouple, magnetic stirrer, 500 ml addition funnel, nitrogen inlet, and glass stopper). The clear, colorless liquid is diluted by the addition of 95% ethanol (EtOH, 160 g). As a result, endotherm is generated. Caustic catalyst is added (10 g of 10% aqueous solution, 0.68 mol%), the reaction color turns yellow and a slight exotherm occurs. Valeraldehyde (258 g, 3.00 mol, 0.89 eq) is added to the addition funnel and slowly added to NE over 4 hours. The heat of reaction raises the temperature to 40-45 ° C. When the addition of valeraldehyde is complete, the RBF contents are transferred to a 1 liter glass bottle, purged with nitrogen, and stored at ambient temperature overnight and at 50 ° C. during the day. The progress of the reaction is monitored by gas chromatography. After 6 days, the conversion has reached 81 area% and the reaction is stopped by the addition of 10% aqueous hydrochloric acid solution (9 ml). The resulting pH = 1 solution is concentrated in vacuo (50 ° C./full vacuum / 0.5 hours) to remove solvent and residual reagents. The resulting green solution (494 g, 90 area% corrected purity, 83% yield) is filtered (0.5 micron), purged with nitrogen, and stored in the refrigerator until needed.

  Catalytic hydrogenation of 2-nitro-3-heptanol to 2-amino-3-heptanol alkanolamine. A sample of 2-amino-3-heptanol (2A3H) is synthesized by reduction of 2-nitro-3-heptanol with a Parr Autoclave unit. Grace 3201 Raney Nickel (RaNi, 90 g wet, 45 g dry, 9 wt%) and methanol (MeOH, 300 g) are placed in a stainless steel, 2 liter autoclave. The autoclave is sealed, assembled, purged with nitrogen, then hydrogen, pressurized with hydrogen (600 psig), stirred at 600 RPM, and warmed to 40 ° C. Nitro-alcohol (491 g) is diluted with absolute ethanol (EtOH, 150 g) and pumped (4 ml / min) into the autoclave. The addition is complete after 3 hours and the completion of the reaction is judged after 3.5 hours (as no hydrogen uptake is observed). Cool the autoclave, stop agitation, vent and purge with nitrogen. The autoclave is broken down and the contents are vacuum filtered to remove the RaNi catalyst. This results in the isolation of a yellow liquid (82 area%), which is concentrated in vacuo (55 ° C./full vacuum) before the product is overhead collected (40-50 ° C./full vacuum). This resulted in the isolation of a clear, colorless solid (302 g, 91.2 area%, 64% overall yield), which contains some oxazolidine (3.4 area%).

Example 3: Preparation of 2-amino-2-methyl-3-heptanol Preparation of 2-methyl-2-nitro-3-heptanol from 2-nitropropane (2-NP) and valeraldehyde. In a manner similar to Example 1, a sample of 2-methyl-2-nitro-3-heptanol was prepared from 2-nitropropane (2-NP, 300 g, 3.37 mol) in a 1 liter 3-neck round bottom flask (RBF, 24 / 40, 29/42, 24/40) (with thermocouple, magnetic stirrer, 500 ml addition funnel, nitrogen inlet, and glass stopper). The clear, colorless liquid is diluted by the addition of absolute ethanol (EtOH, 150 g). As a result, endotherm is generated. Caustic catalyst is added (16 g of 10% aqueous solution, and 0.6 g of 50% aqueous solution, 1.4 mol%), the reaction color turns light yellow and a slight exotherm occurs. Valeraldehyde (258 g, 3.00 mol, 0.89 equiv) is placed in the addition funnel and slowly added to 2-NP over 3 hours. The heat of reaction raises the temperature to 40-45 ° C. When the addition of valeraldehyde is complete, the contents of RBF are transferred into a 1 liter glass bottle, purged with nitrogen, and stored at ambient temperature. The progress of the reaction is monitored by gas chromatography and after 3 weeks 72% completion is reached and the reaction is stopped by adding 10% aqueous hydrochloric acid solution (16 ml). The resulting royal blue color, pH = 1 solution is concentrated in vacuo (50 ° C./full vacuum / 0.5 hours) to remove solvent and residual reagents. The resulting green solution (422 g, 90 area% corrected purity, 80% yield) is diluted with absolute ethanol (150 g), filtered (0.5 micron), purged with nitrogen and kept in the refrigerator until needed. Store.

  Catalytic hydrogenation of 2-methyl-2-nitro-3-heptanol to 2-amino-2-methyl-3-heptanol. A sample of 2-amino-2-methyl-3-heptanol (2A2M3H) is synthesized by reduction of 2-methyl-2-nitro-3-heptanol with a Parr Autoclave unit. Grace 3201 Raney Nickel (RaNi, 90 g wet, 45 g dry, 10 wt%) and methanol (MeOH, 300 g) are placed in a stainless steel, 2 liter autoclave. The autoclave is sealed, assembled, purged with nitrogen and then hydrogen, pressurized with hydrogen, stirred at 600 RPM, and warmed to 40 ° C. Yellow nitro-alcohol (422 g) is diluted with absolute ethanol (EtOH, 150 g) and pumped into autoclave (4 ml / min). The addition is complete after 3 hours and the completion of the reaction is judged after 3.5 hours (as no hydrogen uptake is observed). Cool the autoclave, stop agitation, vent and purge with nitrogen. The autoclave is broken down and the contents are vacuum filtered to remove the RaNi catalyst. This results in the isolation of a pale yellow liquid (80 area%) which is concentrated in vacuo (55 ° C./full vacuum) before the product is overhead collected (50-52 ° C./full vacuum). This resulted in the isolation of a clear, colorless solid (268 g, 91.9 area%, 57% overall yield), which contains some oxazolidine (4.9 area%).

Example 4: Preparation of 2-amino-4-ethyl-3-octanol Preparation of 2-nitro-4-ethyl-3-octanol from nitroethane and 2-ethylhexanal. In a manner similar to Example 1, a sample of 2-nitro-4-ethyl-3-octanol was prepared from a nitroethane (NE, 200 g, 2.67 mol) in a 1 liter three-necked round bottom flask (RBF, 24/40, 29 / 42,24 / 40) (with thermocouple, magnetic stirrer, 500 ml addition funnel, nitrogen inlet, and glass stopper). This is diluted by the addition of absolute ethanol (EtOH, 150 g), resulting in an endotherm. Deionized water (7.5 g) is added followed by caustic catalyst (8.0 ml of 10% aqueous solution). The reaction color becomes darker in orange and a slight exotherm is observed. 2-Ethylhexanal (307 g, 2.40 mol, 0.90 equiv) is placed in the addition funnel and slowly added to NE over 3.5 hours. The heat of reaction raises the temperature to 30 ° C. When the addition of valeraldehyde is complete, the contents of RBF are transferred into a 1 liter glass bottle, purged with nitrogen, and stored at ambient temperature. The progress of the reaction is monitored by gas chromatography. After 2 days, the measured conversion is 53.2 area% and after 2 weeks 55.8 area%. The reaction is then stopped by the addition of 10% aqueous hydrochloric acid solution (8 ml) and the pH = 1 solution is concentrated in vacuo (55 ° C./full vacuum / 0.5 hours) to remove the solvent and residual reagents. The resulting yellow solution (362 g, 72 area% purity, 74.3% yield) is filtered (0.5 micron), purged with nitrogen, and stored in the refrigerator until needed.

  Catalytic hydrogenation of 2-nitro-4-ethyl-3-octanol to 2-amino-4-ethyl-3-octanolamino alcohol. A sample of 2-amino-4-ethyl-3-octanol is synthesized by reduction of 2-nitro-4-ethyl-3-octanol with Parr Autoclave unit. Grace 3201 Raney Nickel (RaNi, 70 g wet, 35 g dry, 10 wt%) and methanol (MeOH, 300 g) are placed in a stainless steel, 2 liter autoclave. The autoclave is sealed, assembled, purged with nitrogen, then hydrogen, pressurized with hydrogen (750 psig), stirred at 600 RPM, and warmed to 40 ° C. Nitro-alcohol (362 g) is diluted with methanol (MeOH, 380 ml) and pumped into an autoclave (5 ml / min). The addition is complete after 2 hours and the completion of the reaction is judged (as no hydrogen uptake is observed) after another 15 minutes. Cool the autoclave, stop agitation, vent and purge with nitrogen. The autoclave is broken down and the contents are vacuum filtered to remove the RaNi catalyst. This resulted in the isolation of a pale yellow liquid (84 area% purity) that was in vacuum (55 ° C./full vacuum) before the product was overhead collected (122 ° C./15 mm) in vacuum jacket 18 ” Concentrate using a Vigreux column / head assembly, which results in the isolation of a clear, colorless solution (182 g, 96.9 area%, 44% overall yield).

Examples 5-16: Corrosion Tests Examples 5-16 illustrate the effect of the amino alcohols of the present invention on the corrosion of metals in contact with fuel.

  Soft carbon steel (MCS), low carbon fine grain steel (LCFGS) and cast iron (CI) specimens (from Metaspec Co) are used. Each specimen is 1 "x 2" x 1/8 "in size. All specimens are cleaned with acetone before full immersion in diesel or biodiesel fuel. Each specimen is weighed before testing and Weigh again after testing and cleaning: Place fuel and water into 4 ounce wide mouth flint glass bottles and completely submerge one specimen into fuel in each bottle. Consists of 20% deionized water (mass basis) For the test sample, the amino alcohol is 0 of the total total mass of fuel and water (56 grams fuel + 14 grams DI water + 0.30 grams amino alcohol). Add at 427% Heat the sample in a mechanical convection oven at 50 ° C. Visually inspect the specimen for 1 week and record the fuel color, stir the bottle to disperse the water, So Weekly agitation assumes agitation by periodic fuel addition and removal from storage tank, leave the bottle closed during the test. The specimens are reweighed and the corrosion is assessed visually, and the results for 3-amino-4-octanol are presented in Table 1.

  As can be seen, the weight loss of 3-amino-4-octanol is reduced for all metals tested in contact with the diesel fuel / water mixture. In addition, visual corrosion is no longer in soft carbon steel and low carbon fine grain steel. For biodiesel fuel, no weight loss reduction is observed with the presence of 3-amino-4-octanol, but a visual reduction in corrosion is observed with low carbon fine steel samples.

Example of Microbial Resistance The following example shows the effect of amino alcohol on the microbial resistance of fuels with and without biocides.

Materials Bacteria. Pseudomonas aeruginosa ATCC # 33988, yeast: Yarrowia tropicalis ATCC # 48138, and template: Hormononi resinae ATCC # 20495, are subcultured in Bushnell-Haas broth and used for mixed inoculum. The organism concentration in the mixed inoculum is as follows: Ps. aeruginosa-4.8 × 10 ⁸ cfu / mL; tropicalis-2.2 × 10 ⁷ cfu / mL; resinae-6.3 × 10 ⁷ cfu / mL

  Diesel fuel. 2007 Certification Diesel, GMPT-5-019-A is obtained from Haltermann Products (a subsidiary of The Dow Chemical Company), Channelview, Texas. Product number: HF 582b; Product code: 20582b.

  Biodiesel fuel. Biodiesel for these examples is obtained from Stepan Company (Northfield, Illinois).

Biocide. Biocides selected for this evaluation include biocides already registered and frequently used in fuel (due to their solubility and effectiveness) (eg Kathon FP 1.5 and FUELSAVER ^™ ). BIOBAN BIT 20 DPG is also tested. Composition and manufacturer information is given below.

Kathon ^™ FP 1.5 (Rohm and Haas): 1.15% 5-chloro-2-methyl-4-isothiazolin-3-one and 0.35% 2-methyl-4-isothiazolin-3-one (CMIT / MIT).

FUELSAVER ^™ (Dow): 90% morpholine dimorpholine blend. 4- (2-nitrobutyl) morpholine and 4,4 ′-(2-ethyl-2-nitrotrimethylene) -dimorpholine (FS).

BIOBAN ^™ BIT 20 DPG (Dow): 18% 1,2 benzisothiazolin-3-one.

Biocide content. For registered biocides, lower and upper labels are used-Kathon ^™ FP: 50 and 400 ppm; FUELSAVER ^™ : 135 and 1000 ppm. BIOBAN ^™ BIT 20 DPG is currently not registered for use in fuel and therefore applies label limits for “oil-in-water emulsions”: 400 and 1800 ppm.

Amino alcohol.
3-Amino-4-octanol (3A4O) 97 +% (from ANGUS Chemical Co., Buffalo Grove, Illinois).

  2-Amino-2-methyl-1-propanol (95% aqueous solution, obtained from ANGUS Chemical Company as AMP-95). This amino alcohol is used for comparison with the amino alcohol of the present invention.

  Amino alcohol content. Both aminoalcohols are evaluated at 1500 and 3000 ppm quantities with and without biocides.

Microbial test procedure.
The test is carried out for 4 weeks in a glass bottle with a bakelite screw cap. For each fuel sample, the aminoalcohol, and then the biocide (if present) is added in the desired amount to either 130 mL of diesel or biodiesel fuel with stirring for 5 minutes. Bushnell-Haas broth (24 mL) is added below the diesel fuel as an aqueous phase. Add 1 mL of mixed inoculum. Samples are mixed weekly by turning the bottle upside down 5 times. The organism count given for day 0 represents the amount of initial organism detected at the bottom of the water after mixing the bottom and fuel.

  Microbial survival is measured using the plate count method. Trypsin soy agar is used for Pseudomonas aeruginosa and Sabouraud dextrose agar (with 0.5 μg / ml gentamicin) is used for Yarrowia tropicalis and bacteriological grade agar 1.5% (0.01% potassium tellurite Is used for Hormoconis resine. Bacteria are cultured for 48 hours at 37 ° C. and fungi are cultured for 5-7 days at 25 ° C.

Data collected from the evaluation of aminoalcohols in diesel fuel is presented in FIGS. 1-3 and Tables 2-4. As can be seen from the data, none of the amino alcohols alone can increase the microbial resistance of the fuel in diesel fuel. However, a synergistic effect is observed between 3-amino-4-octanol (3A4O) and the three biocides evaluated. The synergy is most apparent with low doses of biocide. At higher doses, the biocide itself is essentially completely effective over the test time. 3-Amino-4-octanol is particularly synergistic with FUELSAVER ^™ (FIG. 1). The synergy with Kathon ^™ (CMIT / MIT) is more pronounced earlier in the study and then seems to diminish over time (FIG. 2). The synergistic action of 3-amino-4-octanol with BIT is shown in Ps. Although not significant for Aerogosa (FIG. 3), This is evident in tropicalis (Table 4).

  Data collected by evaluation of the amino alcohols of the present invention in biodiesel fuel is represented by Table 6. As can be seen from the data, the presence of amino alcohol in the biodiesel significantly improves the microbial resistance of the biodiesel even in the absence of a biocide.

  While this invention has been described above according to its preferred embodiments, it can be modified within the spirit and scope of this disclosure. This case is therefore intended to cover any modifications, uses, or adaptations of the invention using the general principles disclosed herein. The present application further covers such departures from the present disclosure, which are within the scope of known or normal practice in the field to which the present invention belongs, and are intended to be within the scope of the claims.

Claims (19)

A hydrocarbonaceous composition; and formula (I):

(Where:
R ¹ and R ³ are each independently H, alkyl of straight or branched chain, alkenyl, alkynyl, cycloalkyl or aryl, or, the carbon to which R ^1, R ³ and they are attached a cycloalkyl ring Forming,
R ² and R ⁴ are each independently H or alkyl, provided that both R ² and R ⁴ contain no more than 2 carbon atoms, and R ⁵ is absent or C ₁ alkylene -C ₁₀ arylene, arylene - alkylene - or - alkylene - arylene - a. )
An amino alcohol containing at least 5 carbon atoms and wherein alkyl, cycloalkyl, alkylene, aryl, and arylene are optionally substituted with alkyl or phenyl;
A blend containing. R ¹ is a C ₁ -C ₆ alkyl, blend of claim 1. R ² is H, methyl or ethyl, blend of claim 1-2. The blend according to claims 1 to ³ , wherein R ³ is hydrogen and R ⁴ is hydrogen. ^5. Blend according to claims 1-4, wherein R5 is absent or is a methylene bridge or an ethylene bridge. The amino alcohol is of formula (II):

(Where:
R ¹ is C ₂ -C ₆ alkyl; and R ² and R ⁴ are each independently H or C ₁ -C ₂ alkyl, and R ² and R ⁴ both contain no more than 2 carbon atoms. On the condition. )
The blend of Claims 1-5 which is a compound of these.   Amino alcohol is 2-amino-3-hexanol, 2-amino-2-methyl-3-hexanol, 3-amino-4-octanol, 2-amino-2-methyl-3-heptanol, 2-amino-4- The blend according to claims 1 to 6, which is ethyl-3-octanol, 2-amino-3-heptanol, 2-amino-1-phenylbutanol, or a mixture of two or more thereof.   The blend according to claim 1, wherein the amino alcohol is 3-amino-4-octanol.   9. Blend according to claims 1-8, further comprising a biocide effective amount of a biocide.   Biocides include triazine, iodopropynyl butyl carbamate, 1,2-benzisothiazolin-3-one, 4,4-dimethyloxazolidine, 7-ethyl-bicyclooxazolidine, 4- (2-nitrobutyl) -morpholine and 4,4. In combination with '-(2-ethyl-2-nitrotrimethylene) dimorpholine, 2-methyl-4-isothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl- In combination with 4-isothiazolin-3-one, 2-bromo-2-nitro-1,3-propanediol, octylisothiazolinone, dichloro-octylisothiazolinone, dibromo-octylisothiazolinone, phenol or the corresponding Sodium or potassium salt, sodium pyrithione, zinc pyri ON, n-butylbenzisothiazolinone, 1- (3-chloroallyl) -3,5,7-triaza-1-azonia adamantane chloride, chlorothalonil, carbendazim, diiodomethyltolylsulfone, 2,2-dibromo- 3-nitrilopropionamide, glutaraldehyde, N, N′-methylene-bis-morpholine, ethylenedioxymethanol, phenoxyethanol, tetramethylol acetylenediurea, dithiocarbamate, 2,6-dimethyl-m-dioxane-4-ol acetate, Dimethylol-dimethyl-hydantoin, tris (hydroxymethyl) nitromethane, bicyclic oxazolidine, (thiocyanomethylthio) -benzothiazole, methylenebis (thiocyanate), substituted dioxaborinane, tetrakis Rokishimechiru) phosphonium sulfate, quaternary ammonium compounds, Kokojiamin, dazomet or mixtures thereof, blends of claim 9,.   The hydrocarbonaceous composition is a liquid fuel and the biocide is a combination of 4- (2-nitrobutyl) -morpholine and 4,4 ′-(2-ethyl-2-nitrotrimethylene) dimorpholine, 5-chloro 2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one, (thiocyanomethylthio) -benzothiazole and methylenebis (thiocyanate) (MBT), substituted dioxaborinane Or a blend thereof according to claim 9-10.   The hydrocarbonaceous composition is petroleum and the biocide is glutaraldehyde, 2-bromo-2-nitro-1,3-propanediol, isothiazolinone compound, 2,2-dibromo-3-nitrilopropionamide, tetrakis ( 11. Blend according to claim 9-10, which is a hydroxymethyl) phosphonium sulfate, an oxazolidine compound, a quaternary ammonium, cocodiamine, dazomet, or a mixture thereof. Liquid fuel;
Corrosion inhibiting amount of formula (I):

(Where:
R ¹ and R ³ are each independently H, linear or branched alkyl, alkenyl, alkynyl, cycloalkyl or aryl, or R ¹ , R ³ and the carbon to which they are attached form a cycloalkyl ring. Forming,
R ² and R ⁴ are each independently H or alkyl, provided that both R ² and R ⁴ contain no more than 2 carbon atoms, and R ⁵ is absent or C ₁ alkylene -C ₁₀ arylene, arylene - alkylene - or - alkylene - arylene - a. )
An amino alcohol containing at least 5 carbon atoms and wherein alkyl, cycloalkyl, alkylene, aryl, and arylene are optionally substituted with alkyl or phenyl; and (i) 4- A blend of (2-nitrobutyl) -morpholine and 4,4 ′-(2-ethyl-2-nitrotrimethylene) dimorpholine;
(Ii) a blend of 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one;
(Iii) a blend of (thiocyanomethylthio) -benzothiazole (TCMTB) and methylenebis (thiocyanate) (MBT); and (iv) a substituted dioxaborinane;
A biocide selected from the group consisting of:
Including fuel blends. The amino alcohol is of formula (II):

(Where:
R ¹ is C ₂ -C ₆ alkyl; and R ² and R ⁴ are each independently H or C ₁ -C ₂ alkyl, and both R ² and R ⁴ contain no more than 2 carbon atoms. On the condition. )
14. The fuel blend of claim 13 which is an amino alcohol.   15. The fuel blend according to claims 13-14, wherein the amino alcohol is 3-amino-4-octanol.   16. The fuel blend of claims 13-15, wherein the weight ratio of amino alcohol to biocide (i) is about 30: 1 to 1: 1.   16. A fuel blend according to claims 13-15, wherein the weight ratio of amino alcohol to biocide (ii) is preferably about 70: 1 to 3: 1. (A) petroleum;
(B) Formula (I):

(Where:
R ¹ and R ³ are each independently H, linear or branched alkyl, alkenyl, alkynyl, cycloalkyl or aryl, or R ¹ , R ³ and the carbon to which they are attached form a cycloalkyl ring. Forming,
R ² and R ⁴ are each independently H or alkyl, provided that both R ² and R ⁴ contain no more than 2 carbon atoms, and R ⁵ is absent or C ₁ alkylene -C ₁₀ arylene, arylene - alkylene - or - alkylene - arylene - a. )
An amino alcohol containing at least 5 carbon atoms and wherein alkyl, cycloalkyl, alkylene, aryl, and arylene are optionally substituted with alkyl or phenyl; and (c) glutaraldehyde 2-bromo-2-nitro-1,3-propanediol, tetrakis (hydroxymethyl) phosphonium sulfate (THPS), 2,2-dibromo-3-nitrilopropionamide (DBNPA), isothiazolinone compound, quaternary ammonium compound A biocide selected from the group consisting of, cocodiamine, and dazomet;
Containing petroleum blends. A method of imparting microbial resistance to a biodiesel fuel, wherein an effective amount of formula (I):

(Where:
R ¹ and R ³ are each independently H, linear or branched alkyl, alkenyl, alkynyl, cycloalkyl or aryl, or R ¹ , R ³ and the carbon to which they are attached form a cycloalkyl ring. Forming,
R ² and R ⁴ are each independently H or alkyl, provided that both R ² and R ⁴ contain no more than 2 carbon atoms, and R ⁵ is absent or C ₁ alkylene -C ₁₀ arylene, arylene - alkylene - or - alkylene - arylene - a. )
Including amino alcohols containing at least 5 carbon atoms and wherein alkyl, cycloalkyl, alkylene, aryl, and arylene are optionally substituted with alkyl or phenyl, Method.

Images