Acids abietic

Separation of Fatty Acids. Tall oil is a by-product of the pulp and paper manufacturiag process and contains a spectmm of fatty acids, such as palmitic, stearic, oleic, and linoleic acids, and rosia acids, such as abietic acid. The conventional refining process to recover these fatty acids iavolves iatensive distillation under vacuum. This process does not yield high purity fatty acids, and moreover, a significant degradation of fatty acids occurs because of the high process temperatures. These fatty and rosia acids can be separated usiag a UOP Sorbex process (93—99) (Tables 8 and 9). 

The isoprene unit exists extensively in nature. It is found in terpenes, camphors, diterpenes (eg, abietic acid), vitamins A and K, chlorophyll, and other compounds isolated from animal and plant materials. The correct stmctural formula for isoprene was first proposed in 1884 (7). 

Fig. 3. Resin acids in rosin sizes, R = CH(CH2)2- The rosin acids are represented here as abietic acid [514-10-3] (1) and levopimaric acid [79-54-9] (2). In rosin there are other isomers and disproportionation products. The product of reaction with fumaric acid (3) is levopimaric acid— fumaric acid adduct...

Other Reactants. Other reactants are used in smaller amounts to provide phenoHc resins that have specific properties, especially coatings appHcations. Aniline had been incorporated into both resoles and novolaks but this practice has been generally discontinued because of the toxicity of aromatic amines. Other materials include rosin (abietic acid), dicyclopentadiene, unsaturated oils such as tung oil and linseed oil, and polyvalent cations for cross-linking. 

Composition. Rosin is primarily a complex mixture of monocarboxyUc acids of alkylated hydrophenanthrene nuclei. These constituents, known as resin acids, represent about 90% of rosin. The resin acids are subdivided into two types, based on their skeletal stmcture. The abietic-type acids contain an isopropyl group pendent from the carbon numbered 13. The pimaric-type acids have a methyl and vinyl group pendent from the same carbon atom. Figure 1 shows the stmcture of typical resin acids abietic acid, C2QH2QO2 (1) is predominant. The remaining 10% of commercial rosin consists of neutral materials that are either hydrocarbons or saponifiable esters. These materials are derived from resin acids by decarboxylation or esterification. 

Fig. 1. Abietic-type acids include abietic acid [514-10-3] (1), levopimaiic acid [79-54-9] (2), neoabietic acid [471-77-2] (3), palustiic acid [1945-53-5] (4), and dehydroabietic acid [1740-19-8] (5). Pimaric-type acids are pimaric acid [127-27-5] (6) and isopimaric acid [5835-26-7] (7).

Polyoxyethylene Esters. This series of surfactants consists of polyoxyethylene (polyethylene glycol) esters of fatty acids and aUphatic carboxyhc acids related to abietic acid (see Resins, natural). They differ markedly from mono- and diglycerides in properties and uses. 

The principal constituents of rosin (qv) are abietic and related acids. Tall oil (qv) is a mixture of unsaturated fatty and aHcycHc acids of the abietic family. Refined tall oil may be high in rosin acids or unsaturated acids, depending on the refining process. Ethoxylates of rosin acids, eg, dehydro abietic acid, are similar to fatty acid ethoxylates in surfactant properties and manufacture, except for thek stabiHty to hydrolysis. No noticeable decomposition is observed when a rosin ester of this type is boiled for 15 min in 10% sulfuric acid or 25% sodium hydroxide (90). Steric hindrance of the carboxylate group associated with the aHcycHc moiety has been suggested as the cause of this unexpectedly great hydrolytic stabiHty. 

Internal Sizing. The most widely used internal sizes are alkyl ketene dimers (AKD), alkenylsuccinic anhydrides (ASA), and rosin-based sizes that are used with papermaker s alum (aluminum sulfate with 14 waters of hydration), polyaluminum chloride (PAG), or polyaluminum siUcosulfate (PAS) (61). The rosin-based sizes are used under acidic conditions. Since the mid 1980 s there has been a steady conversion from acid to alkaline paper production, resulting in static to declining demand for the rosin-based sizing systems. Rosin is a complex mixture of compounds and consists primarily of monocarboxyhc acids with alkylated hydrophenan threne stmctures (62). A main constituent of wood rosin, gum rosin and taH-oil rosin is abietic acid. 

Rosin and tall oil-based tackifiers are derived from feedstock, which is typically obtained by extraction and distillation of the materials from shredded tree stumps or wood chips. A typical structure of one of the different products obtained through this process is this abietic acid structure shown in Fig. 14 as a representative of the rosin acid family. 

Fig. 5. Abietic acid, the largest component in most resin acids.

Paper products Abietic acid Rosin (colophony)... 

Abietinsaure, /. abietic acid, -athylester, m. ethyl abietate. 

Tannenbaum, m. fir tree pine tree, tannenbaumartig, a. arborescent, dendritic. Tannen-baumkristall, m. arborescent crystal, dendrite, -harz, n. fir resin, -harzsaure, /, fir-resin acid, specif, abietic acid, -holzstoff, m. fir (wood) pulp, -nadelol, n. fir-needle oil (loosely) pine-needle oil. -zapfen, m. fir cone, -zapfenol, n. fir-cone oil (loosely) pine-cone oil. 

Most of the inhibitors in use are organic nitrogen compounds and these have been classified by Bregman as (a) aliphatic fatty acid derivatives, b) imidazolines, (c) quaternaries, (d) rosin derivatives (complex amine mixtures based on abietic acid) all of these will tend to have long-chain hydrocarbons, e.g. CigH, as part of the structure, (e) petroleum sulphonic acid salts of long-chain diamines (preferred to the diamines), (/) other salts of diamines and (g) fatty amides of aliphatic diamines. Actual compounds in use in classes (a) to d) include oleic and naphthenic acid salts of n-tallowpropylenediamine diamines RNH(CH2) NH2 in which R is a carbon chain of 8-22 atoms and x = 2-10 and reaction products of diamines with acids from the partial oxidation of liquid hydrocarbons. Attention has also been drawn to polyethoxylated compounds in which the water solubility can be controlled by the amount of ethylene oxide added to the molecule. 

One of the oldest additives is rosin (abietic acid) which improves working, hardening rate and strength (Wallace Hansen, 1939 Molnar Skinner, 1942). El-Tahawi Craig (1971) report that hydrogenated rosin inhibits the formation of crystallites. 

The weakness of this cement was its tendency to dissolve in water. This was prevented by including rosin (mainly abietic acid) or hydrogenated rosin in the formulation (Brauer, Simon Sangermano, 1962). Rosin and fused quartz or calcium hydrogen phosphate monohydrate were added to... 

The effect of flavonoids on spore germination and hyphal growth of ecto-mycorrhizal fungi is poorly known. However, several metabolites relea.sed by the plant roots trigger events leading to their infection (44,55). In the saprotrophic phase, spores of several ectomycorrhizal fungi respond to stimulation by abietic acid, the diterpene resin acid, in root exudates (56). 

N. Fries, K. Serck-Hanssen, L. Hiill-Dimberg, and O. Theander, Abietic acid, an activator of basidio.spore germination in ectoinycorrhizal species of the genus Sidl-liis (Boletaceae). Exp. Mycol. 77 360 (1987). 

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