HOME

TheInfoList



OR:

Resin acid refers to mixtures of several related
carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...
s, primarily
abietic acid Abietic acid (also known as ''abietinic acid'' or ''sylvic acid'') is an organic compound that occurs widely in trees. It is the primary component of resin acid, is the primary irritant in pine wood and resin, isolated from rosin (via isomerizat ...
, found in tree
resin In polymer chemistry and materials science, resin is a solid or highly viscous substance of plant or synthetic origin that is typically convertible into polymers. Resins are usually mixtures of organic compounds. This article focuses on natu ...
s. Nearly all resin acids have the same basic skeleton: three fused rings having the empirical formula C19H29COOH. Resin acids are tacky, yellowish gums that are water-insoluble. They are used to produce soaps for diverse applications, but their use is being displaced increasingly by synthetic acids such as 2-ethylhexanoic acid or petroleum-derived
naphthenic acid Naphthenic acids (NAs) are a mixture of several cyclopentyl and cyclohexyl carboxylic acids with molecular weight of 120 to well over 700 atomic mass units. The main fraction are carboxylic acids with a carbon backbone of 9 to 20 carbons. McKee ...
s.


Botanical analysis

Resin acids are
protectant Plant defense against herbivory or host-plant resistance (HPR) describes a range of adaptations evolved by plants which improve their survival and reproduction by reducing the impact of herbivores. Plants can sense being touched, and they c ...
s and
wood preservative Wood easily degrades without sufficient preservation. Apart from structural wood preservation measures, there are a number of different chemical preservatives and processes (also known as "timber treatment", "lumber treatment" or "pressure treat ...
s that are produced by
parenchyma Parenchyma () is the bulk of functional substance in an animal organ or structure such as a tumour. In zoology it is the name for the tissue that fills the interior of flatworms. Etymology The term ''parenchyma'' is New Latin from the word π ...
tous epithelial cells that surround the resin ducts in trees from
temperate coniferous forests Temperate coniferous forest is a terrestrial biome defined by the World Wide Fund for Nature. Temperate coniferous forests are found predominantly in areas with warm summers and cool winters, and vary in their kinds of plant life. In some, needlel ...
. The resin acids are formed when two-carbon and three-carbon molecules couple with
isoprene Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. Isoprene is an unsaturated hydrocarbon. It is produced by many plants and animals ...
building units to form
monoterpene Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen funct ...
s (volatile),
sesquiterpene Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modificat ...
s (volatile), and
diterpene Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being ...
s (nonvolatile) structures.
Pine A pine is any conifer tree or shrub in the genus ''Pinus'' () of the family Pinaceae. ''Pinus'' is the sole genus in the subfamily Pinoideae. The World Flora Online created by the Royal Botanic Gardens, Kew and Missouri Botanical Garden accep ...
s contain numerous vertical and radial resin ducts scattered throughout the entire wood. The accumulation of resin in the
heartwood Wood is a porous and fibrous structural tissue found in the stems and roots of trees and other woody plants. It is an organic materiala natural composite of cellulose fibers that are strong in tension and embedded in a matrix of lignin tha ...
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. In 2005, as an infestation of the
Mountain pine beetle 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. It has a hard black exoskeleton, and measures approximately , about the siz ...
(''Dendroctonus ponderosae'') and
blue stain fungus Blue stain fungi (also known as sap stain fungi) is a vague term including various fungi that cause dark staining in sapwood. The staining is most often blue, but could also be grey or black. Because the grouping is based solely on symptomatics, it ...
devastated the Lodgepole Pine forests of northern interior
British Columbia British Columbia (commonly abbreviated as BC) is the westernmost province of Canada, situated between the Pacific Ocean and the Rocky Mountains. It has a diverse geography, with rugged landscapes that include rocky coastlines, sandy beaches, ...
, Canada, resin acid levels three to four times greater than normal were detected in infected trees, prior to death. These increased levels show 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 spread of the beetle in the "Red Zone" or the wildlife urban interface.


Chemical components


Abietic-type acids

*Represents the majority 85-90% of typical tall oil. *
abietic acid Abietic acid (also known as ''abietinic acid'' or ''sylvic acid'') is an organic compound that occurs widely in trees. It is the primary component of resin acid, is the primary irritant in pine wood and resin, isolated from rosin (via isomerizat ...
**abieta-7,13-dien-18-oic acid **13-isopropylpodocarpa -7,13-dien-15-oic acid *Neoabietic acid *Dehydroabietic acid *Palustric acid *
Levopimaric acid Levopimaric acid is an abietane-type of diterpene resin acid. It is a major constituent of pine oleoresin with the chemical formula of C20H30O2. In general, the abietene types of diterpene resin acid have various biological activities, such as an ...
*Simplified formula C20H30O2, or C19H29COOH *
molecular weight A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bioch ...
302


Pimaric-type acids

*
pimaric acid Pimaric acid is a carboxylic acid from the resin acid group, often found in the oleoresins of pine trees. It can be prepared by dehydration of abietic acid, which it usually accompanies in mixtures like rosin. It is soluble in alcohols, acetone, a ...
**pimara-8(14),15-dien-18-oic acid *
isopimaric acid Isopimaric acid (IPA) is a toxin which acts as a large conductance Ca2+-activated K+ channel (BK channel) opener. Sources IPA originates from many sorts of trees, especially conifers. Chemistry IPA is one of the members of the resin acid group ...
s *simplified formula C20H30O2 or C19H29COOH *molecular weight 302


Production in tall oil (chemical pulping byproduct)

The commercial manufacture of
wood pulp Pulp is a lignocellulosic fibrous material prepared by chemically or mechanically separating cellulose fibers from wood, fiber crops, waste paper, or rags. Mixed with water and other chemical or plant-based additives, pulp is the major raw mate ...
grade chemical cellulose using the kraft chemical pulping processes releases resin acids. The
Kraft process The kraft process (also known as kraft pulping or sulfate process) is a process for conversion of wood into wood pulp, which consists of almost pure cellulose fibres, the main component of paper. The kraft process involves treatment of wood chip ...
is conducted under strongly basic conditions of
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...
,
sodium sulfide Sodium sulfide is a chemical compound with the formula Na2 S, or more commonly its hydrate Na2S·9 H2O. Both the anhydrous and the hydrated salts in pure crystalline form are colorless solids, although technical grades of sodium sulfide are gener ...
and
sodium hydrosulfide Sodium hydrosulfide is the chemical compound with the formula NaHS. This compound is the product of the half-neutralization of hydrogen sulfide () with sodium hydroxide (NaOH). NaSH and sodium sulfide are used industrially, often for similar purpos ...
, 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 Resin soap is a mix of salts (usually sodium) of resin acids (usually mainly abietic acid). It is a yellow gelatinous pasty soap with use in bleaching and cleaning and as a compound of some varnishes. It also finds use in rubber industry. Resin so ...
.Lars-Hugo Norlin "Tall Oil" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. Kraft soap can be reneutralized with
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...
to restore the acidic forms
abietic acid Abietic acid (also known as ''abietinic acid'' or ''sylvic acid'') is an organic compound that occurs widely in trees. It is the primary component of resin acid, is the primary irritant in pine wood and resin, isolated from rosin (via isomerizat ...
,
palmitic acid Palmitic acid (hexadecanoic acid in IUPAC nomenclature) is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms.Gunstone, F. D., John L. Harwood, and Albert J. Dijkstra. The Li ...
, and related resin acid components. This refined mixture is called tall oil. Other major components include fatty acids and
unsaponifiable Saponification value or saponification number (SV or SN) represents the number of milligrams of potassium hydroxide (KOH) or sodium hydroxide (NaOH) required to saponify one gram of fat under the conditions specified. It is a measure of the ...
sterol Sterol is an organic compound with formula , whose molecule is derived from that of gonane by replacement of a hydrogen atom in position 3 by a hydroxyl group. It is therefore an alcohol of gonane. More generally, any compounds that contain the go ...
s. 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'', commonly known as slash pine,Family, P. P. (1990). Pinus elliottii Engelm. slash pine. ''Silvics of North America: Conifers'', (654), 338. is a conifer tree native to the Southeastern United States. Slash pine is named after ...
(''Pinus elliottii''); inland areas of the same region have a preponderance of
Loblolly Pine ''Pinus taeda'', commonly known as loblolly pine, is one of several pines native to the Southeastern United States, from East Texas to Florida, and north to southern New Jersey. The wood industry classifies the species as a southern yellow pine. ...
(''Pinus taeda''). Slash Pine generally contains a higher concentration of resin acids than Loblolly Pine. 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 acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, fr ...
s fraction is usually lower than the resin acids, and unsaponifiables amount to 6-8%. Farther north in
Virginia Virginia, officially the Commonwealth of Virginia, is a state in the Mid-Atlantic and Southeastern regions of the United States, between the Atlantic Coast and the Appalachian Mountains. The geography and climate of the Commonwealth ar ...
, where
Pitch Pine ''Pinus rigida'', the pitch pine, is a small-to-medium-sized pine. It is native to eastern North America, primarily from central Maine south to Georgia and as far west as Kentucky. It is found in environments which other species would find unsuit ...
(''Pinus rigida'')and
Shortleaf Pine ''Pinus echinata'', the shortleaf pine, is a species of pine native to the southeastern United States. Description The tree is variable in form, sometimes straight, sometimes crooked, with an irregular crown. The tree reaches heights of with a ...
(''Pinus echinata'') are more dominant, the resin acid content decreases to as low as 30-35% with a corresponding increase in the fatty acids present. In
Canada Canada is a country in North America. Its ten provinces and three territories extend from the Atlantic Ocean to the Pacific Ocean and northward into the Arctic Ocean, covering over , making it the world's second-largest country by tot ...
, where mills process
Lodgepole Pine ''Pinus contorta'', with the common names lodgepole pine and shore pine, and also known as twisted pine, and contorta pine, is a common tree in western North America. It is common near the ocean shore and in dry montane forests to the subalpine, ...
(''Pinus contorta'') in interior
British Columbia British Columbia (commonly abbreviated as BC) is the westernmost province of Canada, situated between the Pacific Ocean and the Rocky Mountains. It has a diverse geography, with rugged landscapes that include rocky coastlines, sandy beaches, ...
and
Alberta Alberta ( ) is one of the thirteen provinces and territories of Canada. It is part of Western Canada and is one of the three prairie provinces. Alberta is bordered by British Columbia to the west, Saskatchewan to the east, the Northwest Ter ...
,
Jack Pine Jack pine (''Pinus banksiana'') is an eastern North American pine. Its native range in Canada is east of the Rocky Mountains from the Mackenzie River in the Northwest Territories to Cape Breton Island in Nova Scotia, and the north-central and ...
(''Pinus banksiana''),
Alberta Alberta ( ) is one of the thirteen provinces and territories of Canada. It is part of Western Canada and is one of the three prairie provinces. Alberta is bordered by British Columbia to the west, Saskatchewan to the east, the Northwest Ter ...
to
Quebec Quebec ( ; )According to the Canadian government, ''Québec'' (with the acute accent) is the official name in Canadian French and ''Quebec'' (without the accent) is the province's official name in Canadian English is one of the thirtee ...
and
Eastern White Pine ''Pinus strobus'', commonly called the eastern white pine, northern white pine, white pine, Weymouth pine (British), and soft pine is a large pine native to eastern North America. It occurs from Newfoundland, Canada west through the Great Lakes ...
(''Pinus strobus'') and
Red Pine ''Pinus resinosa'', known as red pine (also Norway pine in Minnesota), is a pine native to North America. Description Red pine is a coniferous evergreen tree characterized by tall, straight growth. It usually ranges from in height and in trun ...
(''Pinus resinosa''),
Ontario Ontario ( ; ) is one of the thirteen provinces and territories of Canada.Ontario is located in the geographic eastern half of Canada, but it has historically and politically been considered to be part of Central Canada. Located in Central Ca ...
to
New Brunswick New Brunswick (french: Nouveau-Brunswick, , locally ) is one of the thirteen provinces and territories of Canada. It is one of the three Maritime provinces and one of the four Atlantic provinces. It is the only province with both English and ...
, 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, in
Finland Finland ( fi, Suomi ; sv, Finland ), officially the Republic of Finland (; ), is a Nordic country in Northern Europe. It shares land borders with Sweden to the northwest, Norway to the north, and Russia to the east, with the Gulf of B ...
,
Sweden Sweden, formally the Kingdom of Sweden,The United Nations Group of Experts on Geographical Names states that the country's formal name is the Kingdom of SwedenUNGEGN World Geographical Names, Sweden./ref> is a Nordic country located on ...
and
Russia Russia (, , ), or the Russian Federation, is a List of transcontinental countries, transcontinental country spanning Eastern Europe and North Asia, Northern Asia. It is the List of countries and dependencies by area, largest country in the ...
, resin acid values from
Scots Pine ''Pinus sylvestris'', the Scots pine (UK), Scotch pine (US) or Baltic pine, is a species of tree in the pine family Pinaceae that is native to Eurasia. It can readily be identified by its combination of fairly short, blue-green leaves and orang ...
(''Pinus sylvestris'') may vary from 20 to 50%, fatty acids from 35 to 70%, and unsaponifiables from 6 to 30%.


References

{{DEFAULTSORT:Resin Acid Biomolecules Acids Resins