Resin acids are protectants and wood preservatives that are produced by parenchymatous epithelial cells that surround the resin ducts in trees from temperate coniferous forests. The resin acids are formed when two- and three-carbon molecules couple with isoprene building units to form mono- (volatile), sesqui- (volatile), and diterpene(nonvolatile) structures. Resin acids have two functional groups, carboxyl group and double bonds. Nearly all have the same basic skeleton: a 3-ring fused system with the empirical formula C₁₉H₂₉COOH. Protectants are pesticidal substances that are produced by plants to protect the plant from insects and other harmful organisms. ... For other uses, see Wood (disambiguation). ... Parenchyma is a term used to describe a bulk of a substance. ... Pine forests are an example of a temperate coniferous forests Temperate coniferous forests are a terrestrial biome found in temperate regions of the world with warm summers and cool winters and adequate rainfall to sustain a forest. ... This article does not cite any references or sources. ... Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. ... Many terpenes are derived from conifer resins, here a pine. ... A carboxyl or carboxylic group is a functional group consisting of a carbon atom and an oxygen atom doubly bonded to each other. ...

Natural occurrence

Pines contain numerous vertical and radial resin ducts scattered throughout the entire wood. The accumulation of resin in the heartwood and resin ducts causes a maximum concentration in the base of the older trees. Resin in the sapwood, however, is less at the base of the tree and increases with height. Subgenera Subgenus Strobus Subgenus Ducampopinus Subgenus Pinus See Pinus classification for complete taxonomy to species level. ... A tree trunk as found at the Veluwe, The Netherlands Wood is a material found as the primary content of the stems of woody plants, especially trees, but also shrubs. ... A tree trunk as found at the Veluwe, The Netherlands Wood is an organic material found as the primary content of the stems of woody plants, especially trees, but also shrubs. ...

Natural resins are water-insoluble mixtures of compounds, many of which have a hydroaromatic structure. Mixtures of isomeric carboxylic acids, such as abietic and pimaric acids, which occur in rosin in nature in solvent-free form, in the form of tree sap or wood rosin such as pine oleoresin, where they are dissolved in terpenic hydrocarbons. They can also be present as fossil coal or copal resins, in old pine tree stumps, etc. Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... Also known as: abietinic acid, sylvic acid, 13-isopropylpodocarpa-7,13-dien-15-oic acid Molecular formula: C19H29COOH CAS No: 514_10_3 EINECS No: 208_173_3 The ester is called an abietate. ... Pimaric acid Pimaric acid is a carboxylic acid from the resin acid group. ... A 20 g cake of amber violin bow rosin. ... For other uses, see Solvent (disambiguation). ... Sap exuding (gummosis) from the stem of a koa tree, probably in response to surface damage Sap is the fluid carried in tubules inside a plant, circulating to distribute food and water to various parts of the plant. ... Insect trapped in resin. ... Many terpenes are derived from conifer resins, here a pine. ... A 3-dimensional rendered Ball-and-stick model of the methane molecule. ... For other uses, see Fossil (disambiguation). ... Coal Example chemical structure of coal Coal is a fossil fuel formed in ecosystems where plant remains were saved by water and mud from oxidization and biodegradation. ... Copal is a type of resin, sometimes referred to as pom (the Maya language name). ...

Chemical characteristics

Resin acids occur in pines in a number of isomeric forms having the molecular formula C₁₉H₂₉COOH and in some related structures. The most prevalent resin acids are:

Abietic-type acids

Abietic acid

• abietic acid
  • abieta-7,13-dien-18-oic acid
  • 13-isopropylpodocarpa -7,13-dien-15-oic acid
• neoabietic acid
• dehydroabietic acid
• palustric acid
• simplified formula C₂₀H₃₀O₂, or C₁₉H₂₉COOH
• represents the majority 85-90% of typical tall oil.
• structurally shown as (CH₃)₄C₁₅H₁₇COOH
• molecular weight 302

Also known as: abietinic acid, sylvic acid, 13-isopropylpodocarpa-7,13-dien-15-oic acid Molecular formula: C19H29COOH CAS No: 514_10_3 EINECS No: 208_173_3 The ester is called an abietate. ... Tall oil, also called liquid rosin or tallol, is a viscous yellow-black odorous liquid obtained as a byproduct of the Kraft process of wood pulp manufacture. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ...

Pimaric-type acids

Pimaric acid

• pimaric acid
  • pimara-8(14),15-dien-18-oic acid
• levopimaric acid
• isopimaric acids
• simplified formula C₂₀H₃₀O₂ or C₁₉H₂₉COOH
• structurally represented as (CH₃)₃(CH₂)C₁₅H₁₈COOH
• molecular weight 302

Image File history File links Pimaric_acid. ... Pimaric acid Pimaric acid is a carboxylic acid from the resin acid group. ...

Production in tall oil (chemical pulping byproduct)

Commercially, the manufacture of wood pulp grade chemical cellulose using the kraft chemical pulping processes releases these resin acid compounds. The Kraft process is conducted under strongly basic conditions of sodium hydroxide, sodium sulfide and sodium hydrosulfide which neutralizes these resin acids, converting them to their respective sodium salts, sodium abietate, ((CH₃)₄C₁₅H₁₇COONa) sodium pimarate ((CH₃)₃(CH₂)C₁₅H₂₃COONa) and so on. In this form, the sodium salts are insoluble and, being of lower density than the spent pulping process liquor, float to the surface of storage vessels during the process of concentration, as a somewhat gelatinous pasty fluid called kraft soap, or resin soap. International Paper Company Wood pulp is the most common material used to make paper. ... The Kraft process (also known as Kraft pulping or sulfate process) is used in production of paper pulp and involves the use of caustic sodium hydroxide and sodium sulfide to extract the lignin from wood chips in large pressure vessels called digesters. ... Sodium hydroxide (NaOH), also known as lye, caustic soda and (incorrectly, according to IUPAC nomenclature)[1] sodium hydrate, is a caustic metallic base. ... Sodium sulfide, or Na2S, is a water soluble chemical compound. ... Sodium hydrosulfide is the chemical compound with the formula NaSH. Other names include sodium bisulfide, sodium sulfhydrate, and sodium hydrogen sulfide. ... Wikipedia does not have an article with this exact name. ...

Kraft soap can be reneutralized in the presence of concentrated sulfuric acid to restore the acidic forms abietic acid, palmiric acid and their isomers which form the resin acid component of a pulping byproduct called tall oil. Other major components include fatty acids and unsaponifiable sterols. Sulfuric acid, (also known as sulphuric acid) H2SO4, is a strong mineral acid. ... Also known as: abietinic acid, sylvic acid, 13-isopropylpodocarpa-7,13-dien-15-oic acid Molecular formula: C19H29COOH CAS No: 514_10_3 EINECS No: 208_173_3 The ester is called an abietate. ... Tall oil, also called liquid rosin or tallol, is a viscous yellow-black odorous liquid obtained as a byproduct of the Kraft process of wood pulp manufacture. ... Unsaponifiables are components of an oil, fat, wax, etc. ... Sterols, or steroid alcohols are a subgroup of steroids with a hydroxyl group in the 3-position of the A-ring. ...

Resin acids, because of the same protectant nature they provide in the trees where they originate, also impose toxic implications on the effluent treatment facilities in pulp manufacturing plants. Furthermore, any residual resin acids that pass the treatment facilities add toxicity to the stream discharged to the receiving waters.

Variation with species and biogeoclimatic zone

The chemical composition of tall oil varies with the species of trees used in pulping, and in turn with geographical location. For example, the coastal areas of the southeastern United States have a high proportion of Slash Pine (Pinus elliottii); inland areas of the same region have a preponderance of Loblolly Pine (Pinus taeda). Slash Pine generally contains a higher concentration of resin acids than Loblolly Pine. Binomial name Pinus elliottii Engelm. ... Binomial name Pinus taeda L. The Loblolly Pine (Pinus taeda) is one of the pines native to the southeastern United States. ...

In general, the tall oil produced in coastal areas of the southeastern United States contains over 40% resin acids and sometimes as much as 50% or more. The fatty acids fraction is usually lower than the resin acids, and unsaponifiables amount to 6-8%. Farther north in Virginia, the resin acid content decreases to as low as 30-35% with a corresponding increase in the fatty acids present. Not to be confused with fats. ... This article is about the U.S. state. ...

Still farther north in Canada, where mills process Lodgepole Pine (Pinus contorta) Jack Pine (Pinus banksiana), Eastern White Pine (Pinus strobus) and Red Pine (Pinus resinosa), resin acid levels of 25% are common with unsaponifiable contents of 12-25%. Similar variations may be found in other parts of the United States and in other countries. For example, resin acid values from Scots Pine (Pinus sylvestris) in Finland may vary from 20 to 50%, fatty acids from 35 to 70 %, and unsaponifiables from 6 to 30%. Binomial name Pinus contorta Douglas Lodgepole Pine (Pinus contorta) is a common tree in western North America. ... Binomial name Pinus banksiana Lamb. ... Binomial name L. Eastern White Pine (Pinus strobus) is a large pine native to eastern North America, occurring from Newfoundland west to Minnesota and southeastern Manitoba, and south along the Appalachian Mountains to the extreme north of Georgia. ... Binomial name Pinus resinosa The Red Pine (Pinus resinosa), is a North American pine, occurring from Newfoundland west to southeast Manitoba, and south to northern Illinois and Pennsylvania, with a small outlying population in the Appalachian Mountains in West Virginia. ... Binomial name L. Distribution The Scots Pine (Pinus sylvestris L.; family Pinaceae) is a species of pine native to Europe and Asia, ranging from Great Britain and Spain east to eastern Siberia, south to the Caucasus Mountains, and as far north as Lapland. ...

In 2005, as an infestation of the Mountain pine beetle (Dendroctonus ponderosae), devastated the Lodgepole Pine forests of northern interior British Columbia, Canada, resin acid levels three to four times greater than normal were detected in infected trees, prior to death. These increased levels are based on the fact that a tree uses the resins as a defense. Resins are both toxic to the beetle and the fungus and also can entomb the beetle in diterpene remains from secretions. Increasing resin production has been proposed as a way to slow the spored of the beetle in the "Red Zone" or the wildlife urban interface. Binomial name Dendroctonus ponderosae Hopkins, 1905 The mountain pine beetle, Dendroctonus ponderosae, is a species of bark beetle native to the forests of western North America from Mexico to central British Columbia. ... Motto: Splendor sine occasu (Latin: Splendour without diminishment) Capital Victoria Largest city Vancouver Official languages English (de facto) Government Lieutenant-Governor Steven Point Premier Gordon Campbell (BC Liberal) Federal representation in Canadian Parliament House seats 36 Senate seats 6 Confederation July 20, 1871 (6th province) Area  Ranked 5th Total 944...