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Author: admin, 05.07.2013
In at least one embodiment the corrosion inhibiter is a composition comprising at least 60% water, 1-20% zinc chloride and 1-20% phosphoric acid. In another embodiment, the corrosion inhibitor of the invention comprises a product of tall oil, reaction products with 2[2-(dimethylamino)ethoxy]ethanol, 2-(dimethylamino)ethanol, C18-unsaturated fatty acid trimers, and branched DDBSA. In an embodiment, the corrosion inhibitor composition of the invention includes the following formula (1) using dimethylalkanolamines with trimer acid [CAS 68937-90-6]. In an embodiment, the corrosion inhibitor composition of the invention includes the following formula (2) dimethylalkanolamines with trimer acid [CAS 68937-90-6]. In an embodiment, the corrosion inhibitor composition of the invention includes the following formula (3) using dimethylalkanolamines with tall oil [CAS 8002-26-4]. In an embodiment, the corrosion inhibitor composition of the invention includes the following formula (4) using dimethylalkanolamines with tall oil [CAS 8002-26-4]. The second group of salts which can form in this blend is with tall oil, exemplified in formulas (3) and (4) above. In an embodiment, the corrosion inhibitor composition of the invention includes the following formula (5) using dimethylalkanolamines with branched dodecylbenzene sulfonic acid [CAS 68411-32-5]. In an embodiment, the corrosion inhibitor composition of the invention includes the following formula (6) using dimethylalkanolamines with branched dodecylbenzene sulfonic acid [CAS 68411-32-5].
A representative structure of the salts formed with branched dodecylbenzene sulfonic acid (DDBSA) is shown above.
Chemically modified maleated fatty acid compositions and the salts thereof, especially chemically modified tall oil fatty acid containing compositions are useful in formulating corrosion inhibitors, as emulsifiers, as collectors in mining applications, and as cross-linking agents, such compositions find particular utility for petroleum-related applications.
The method of claim 1 in which the corrosion inhibitor comprises at least 60% water, 1-20% zinc chloride and 1-20% phosphoric acid. The method of claim 1 in which the corrosion inhibitor is so acidic that it would be expected to corrode the pipeline in the absence of an inhibitor. In an embodiment, the corrosion inhibitor of the invention comprises a product of dimethylaminoethoxyethanol, dimethylethanolamine, tall oil, C18-unsaturated fatty acid trimers, and branched dodecylbenzenesulfonic acid (DDBSA).
Crude tall oil is for example, a by-product of the pulp and paper industry and yields another complex mixture of fatty acids, rosin acids, and lesser amounts of terpenes and sterols.
Tall oil fatty acids may comprise any combination of the foregoing examples and others known in the art. The composition of these salts has been approximated based on general reactivity and percentages of each acid added to the blends. A composition comprising chemically modified, maleated unsaturated fatty acids and the salts thereof, wherein the chemical modification is selected from the group consisting of (1) esterification of the maleated unsaturated fatty acids with ricinoleic acid, (2) amidation of the maleated unsaturated fatty acids using a polyamine supplied in an amount to cause cross linking between maleated fatty acid molecules, (3) a combination of esterification and amidation of the maleated unsaturated fatty acids using an amino alcohol supplied in an amount to cause cross linking between maleated fatty acid molecules, (4) esterification of the maleated unsaturated fatty acids with an alkynyl alcohol selected from propargyl alcohol, 1-hexyn-3-ol, 5-decyne-4,7-diol, oxyalkylated propargyl alcohol and mixtures thereof, (5) amidation of the maleated unsaturated fatty acids with morpholine, (6) amidation of the maleated unsaturated fatty acids with a fatty imidazoline, (7) esterification of the maleated unsaturated fatty acids with a phosphate ester, (8) metal chelator modification, (9) reaction of the maleated unsaturated fatty acids with an amino acid, (10) xanthate modification, (11) thiophosphate ester modification, (12) hydroxamic acid modification, (13) sulfonate modification, (14) sulfate modification and combinations thereof. The composition of claim 1 wherein the chemically modified, maleated unsaturated fatty acid has an average molecular weight greater than about 820.


The composition of claim 1 wherein the maleated unsaturated fatty acid is amidated using a polyamine at a temperature between 50° C. The composition of claim 1 wherein the unsaturated fatty acids comprise unsaturated C18 fatty acids. The composition of claim 6 wherein the unsaturated fatty acids comprise a tall oil composition containing tall oil fatty acid. The composition of claim 7 wherein the unsaturated fatty acids comprise a tall oil composition containing a tall oil rosin acid. The composition of claim 1 wherein the maleated fatty acids have been maleated with maleic anhydride. The composition of claim 9 wherein the maleated fatty acids have been maleated with from about 2% to about 25% by weight of maleic anhydride. The present invention particularly relates to a variety of chemically modified maleated tall oil fatty acid-containing products.
Such products should be useful in formulating corrosion inhibitors, as emulsifiers, as cross-linking agents, as mining collectors and as an antistrip agent for asphalt, and are especially useful in petroleum-related applications such as oil well applications.
TOFAs are generally produced as a distillation fraction of crude tall oil and therefore contain a mixture of saturated and unsaturated fatty acids, rosin acids, and mixtures thereof. Thus, tall oil products containing both fatty acid and rosin acid components can be used as a suitable starting material for making a maleated fatty acid material that then is modified in accordance with the present invention. Such maleated fatty acid starting materials are amenable to subsequent chemical modification in accordance with the present invention for preparing functionalized material suitable for use as, or for producing materials suitable for use as emulsifiers, dedusting agents, viscosity control agents, corrosion inhibitors, cross-linking agents, mining collectors, asphalt antistrip agents and the like.
Thus, suitable fatty acids may be obtained from tall oil, vegetable oils, animal oils, algal-produced oils, microbial-produced oils and mixtures thereof.
Indeed, any naturally occurring oil, or a synthetic oil, which contains a fatty acid having unsaturated linkages (unsaturated fatty acid) is potentially suitable as a starting material for the maleation reaction(s). Processing such materials to obtain the unsaturated fatty acid and the related maleated fatty acid compositions is within the skill of the art. As a result, such sources of fatty acids often are referred to as unsaturated oils and unsaturated fatty acids.
As is known in the art, tall oil refers to the resinous yellow-black oily liquid obtained as an acidified byproduct in the Kraft or sulfate processing of pine wood. In fact as some inhibitors are highly basic or acidic, it would be expected that in the absence of a neutralizing material (such as slurry components) the inhibitor in the absence of slurry could be expected to corrode the pipeline by itself In at least one embodiment the inhibitor is one that would be expected to corrode the pipeline. The composition of tall oil is variable with differences seen in regional sources and manufacturing processes as well as seasonal influences.
These starting materials will be referred to as tall oil fatty acid containing compositions, or TOFA-containing compositions and thus embrace compositions composed of primarily TOFA and compositions containing both TOFA and other materials such as rosin acids.


These oils generally contain as one significant constituent linoleic acid, an unsaturated long chain fatty acid and may also contain other unsaturated fatty acids and rosin acids. Tall oil, prior to refining, is normally a mixture of rosin acids, fatty acids, sterols, high-molecular weight alcohols, and other alkyl chain materials. Representative tall oil distillate components include tall oil fatty acids, and mixtures of tall oil fatty acids with tall oil rosin acids. The corrosion inhibitor may comprise at least 60% water, 1-20% zinc chloride and 1-20% phosphoric acid. In addition, trimer acid contains variable percentages of dimers and trimers, adding to the complexity. 4,927,669, tall oil fatty acid (TOFA) is functionalized using maleic anhydride, or fumaric acid, in the presence of a catalyst such as iodine, clay or silica. 4,658,036 describes reacting a maleated TOFA molecule, such as the Diels-Alder adduct of linoleic acid, sequentially with diethylenetriamine under conditions suitable for forming a cyclic imide (and using an excess of amine moieties to maleate moieties) and then reacting the free amino group of the imide with additional TOFA. 5,759,485 describes a class of water soluble corrosion inhibitors in which the maleic anhydride-functionalized TOFA (specifically the Diels-Alder reaction adduct with linoleic acid) is neutralized with aminoethylethanolamine and also with one of imidazoline, amidoamine or a combination thereof. Distillation of crude tall oil is often used to recover a mixture of fatty acids in the C16-C20 range. The fatty acids are reacted in a first step to promote a Diels-Alder reaction with linoleic acid, the product then being distilled to remove unreacted fatty acid. The commercially available tall oil products XTOL®100, XTOL®300, and XTOL®304 (all from Georgia-Pacific Chemicals LLC, Atlanta, Ga.), for example, all contain saturated and unsaturated fatty acids in the C16-C20 range, as well as minor amounts of rosin acids. The structures above provide a representation of the salts formed from dimethylalkanolamines and tall oil (oleic acid is shown).
It is understood by those skilled in the art that tall oil is derived from natural sources and thus its composition varies among the various sources. 4,927,669 with a polyalcohol, such as ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, glycerin, pentaerythritol, trimethylolpentane, and sorbitol to form an acid-anhydride ester corrosion inhibitor, which in turn may be neutralized with an amine, with a metal oxide, or with a hydroxide before use.
5,385,616) and then is neutralized with an ethoxylated amine, such as an ethoxylated fatty amine to form the corresponding salt.
The separate products are preferably blended together to provide a composition, which is said to contain 75 to 95% maleinized fatty acids, 15 to 20% thermal dimer and trimer and remaining unreacted fatty acid, useful as a corrosion inhibitor.




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