Biosynthesis of Abietic acid  [c.164]

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).  [c.301]

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).  [c.462]

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.  [c.293]

A wide variety of additives ate being used to reduce aggregation or agglomeration and flocculation to improve dispersibiUty and color strength of organic pigments. These include resins, especially those related to abietic acid, aUphatic amines, amides, substituted derivatives of pigments themselves, and various combinations thereof. The additives are most effective if they are present when the pigment crystals are being generated.  [c.24]

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.  [c.249]

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.  [c.250]

Abietic acid [514-10-3] m 302.5, m 172-175 , [a] -H6 (-kh )(c 1, eioh), pk  [c.81]

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.  [c.503]

Rosin and rosin esters. Rosins are derived from tree stumps (wood rosin), sap (gum rosin), or pulpwood (tall oil rosin). Rosin is a C20 mono-acid with three fused C6 rings. A variety of isomers occur naturally, the preponderance of which depends on the source of the rosin [22]. Abietic acid is the most common isomer (see Fig. 5). Rosin is an outstanding tackifier. Its fused ring structure provides high solvency power for a wide range of polymers. The acid group improves specific adhesion to most substrates. However, its dark color, strong odor, poor thermo-oxidative stability, and the potential for allergic reactions limit its use. With a softening point of 80 C, rosin is also prone to block and therefore  [c.719]

Fig. 5. Abietic acid, the largest component in most resin acids. Fig. 5. Abietic acid, the largest component in most resin acids.
Ireland,yOC, 1966,31, 2543. Meyer, JOC, 1977,42, 2769. Abietic Acid  [c.381]

Paper products Abietic acid Rosin (colophony)  [c.308]

Continuous polymerization in a staged series of reactors is a variation of this process (82). In one example, a mixture of chloroprene, 2,3-dichloro-l,3-butadiene, dodecyl mercaptan, and phenothiazine (15 ppm) is fed to the first of a cascade of 7 reactors together with a water solution containing disproportionated potassium abietate, potassium hydroxide, and formamidine sulfinic acid catalyst. Residence time in each reactor is 25 min at 45°C for a total conversion of 66%. Potassium ion is used in place of sodium to minimize coagulum formation. In other examples, it was judged best to feed catalyst to each reactor in the cascade (83).  [c.541]

The resin acids found in rosins are generally of the abietic- and pimaric-type. Rosins of various pine species differ in their content of abietic vs. pimaric-type acids. Rosins from species exhibiting high abietic-type acid compositions are preferred for production of rosin derivatives. However, the differences in properties of rosins are often associated with their non-resin acid content instead of their chemical compositions. On the other hand, the compositions of rosins from different sources greatly differ [22]. Table 8 shows a typical distribution of resin acids in rosins obtained from gum, tall oil and wood sources.  [c.601]

TacklfyingResins. Tackifying resins have found great use in modifying a number of different types of adhesives. Abietic acid [514-10-3] and pimaric acid [127-27-5], known as rosin acids, are obtained from pine tree sap. These acids are not used in thek natural form rather they are modified by a number of techniques, such as heating to high temperatures to induce disproportionation, reaction with alcohols to provide an estetified product, or reaction with various catalysts either to hydrogenate or to polymerize the material. Aromatic resins, for example the coumarone—indene resins, are obtained from natural product streams, such as coal, petroleum, or wood tar. Chemicals such as indene [95-13-6] or methylindene are polymerized with styrene [100-42-5] or methylstyrene in the presence of a Lewis acid to provide aromatic tackifying resins. AUphatic hydrocarbon tackifying resins are obtained from polymerization products of cis- and trans-piperylene (1,3-pentadiene) and isoprene and dicylopentadiene terpene resins are obtained from turpentine and citms peels. Additionally, natural products such as a-pinene, P-pinene, and dipentene are polymerized in the presence of aluminum chloride to provide terpene resins. The uses of tackifying resins are discussed below.  [c.234]

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 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
A number of monobasic acids that are not derived from fats and oils have been used ia alkyd resias. However, except ia the rare cases of making the so-called oil-free alkyds for special purposes, they are used ia conjunction with fatty acids to modify resia properties. Rosia acids, primarily abietic acid [514-10-3] may be used ia neat form or be brought ia as a part of TOFA. Presumably, the fused ring stmcture of rosia coatributes to the film hardness, initial gloss, and water resistance of the alkyd. However, color and color retention, and exterior durabiUty are adversely affected if the rosia coateat goes much above 5—6%. The dryiag rate of alkyds usually appears to be improved with rosia modification. However, siace rosia does aot participate ia the oxidative dryiag mechanism that appHes to polyuasaturated fatty acids, the tme dryiag rate of the alkyd resia is actually reduced due to a reductioa of the fatty acid uasaturatioa. Syathetic saturated carboxyUc acids, such as pelargonic acid [112-05-0] 2-ethylhexanoic acid [149-57-5] isooctanoic acid, and aromatic monobasic acids such as benzoic acid [65-85-0] and -alkylbenzoic acids, can give even better color retention, gloss retention, and exterior durabihty but less flexibiUty than those based on castor or coconut fatty acids. The aromatic acids, similar to rosia, also give higher film hardness and faster apparent drying rate.  [c.35]

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.  [c.138]

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.  [c.310]

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.  [c.794]

In the initial black Hquor concentration, saponified fatty and resin acid salts separate as tall oil soaps (see Tall oil). These soaps can be skimmed from the aqueous spent Hquor, acidified, and refined to give a cmde tall oil composed of resin acids, chiefly abietic and neoabietic fatty acids, chiefly oleic and Hnoleic and an unsaponifiable fraction made of phytosterols, alcohols, and hydrocarbons. Tall oil is fractionated primarily into fatty acids (see  [c.270]

Salt formation. The resin acids have a low acid strength. The pa s (ionization constants) values of resin acids are difficult to obtain, and values of 6.4 and 5.7 have been reported [23] for abietic and dehydroabietic acids, respectively. Resin acids form salts with sodium and aluminium. These salts can be used in detergents because of micelle formation at low concentrations. Other metal salts (resinates) of magnesium, barium, calcium, lead, zinc and cobalt are used in inks and adhesive formulations. These resinates are prepared by precipitation (addition of the heavy metal salt to a solution of sodium resinate) or fusion (rosin is fused with the heavy metal compound).  [c.602]

See pages that mention the term AbIETIC ACID : [c.9]    [c.144]    [c.344]    [c.851]    [c.1154]    [c.1]    [c.1]    [c.139]    [c.139]    [c.72]    [c.478]    [c.308]    [c.5]    [c.438]    [c.440]    [c.599]   
Organic syntheses Biclormethyl ether (1956) -- [ c.32 ]

The logic of chemical synthesis (1989) -- [ c.381 ]