Linseed oil

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Flax, flax seeds, linseed oil, linseed cake From flax to linseed oil..JPG
Flax, flax seeds, linseed oil, linseed cake

Linseed oil, also known as flaxseed oil or flax oil (in its edible form), is a colorless to yellowish oil obtained from the dried, ripened seeds of the flax plant (Linum usitatissimum). The oil is obtained by pressing, sometimes followed by solvent extraction.

Contents

Owing to its polymer-forming properties, linseed oil is often blended with combinations of other oils, resins or solvents as an impregnator, drying oil finish or varnish in wood finishing, as a pigment binder in oil paints, as a plasticizer and hardener in putty, and in the manufacture of linoleum. Linseed oil use has declined over the past several decades with increased availability of synthetic alkyd resins—which function similarly but resist yellowing. [1]

Structure and composition

Representative triglyceride found in a linseed oil, a triester (triglyceride) derived of linoleic acid, alpha-linolenic acid, and oleic acid Triglyceride unsaturated Structural Formulae V2.svg
Representative triglyceride found in a linseed oil, a triester (triglyceride) derived of linoleic acid, alpha-linolenic acid, and oleic acid

Linseed oil is a triglyceride, like other fats. Linseed oil is distinctive for its unusually large amount of α-linolenic acid, which oxidises in air. The fatty acids in a typical linseed oil are of the following types: [2]

Drying properties

Having a high content of di- and tri-unsaturated esters, linseed oil is susceptible to polymerization reactions upon exposure to oxygen in air. This polymerization, which is called autoxidation, results in the rigidification of the material. [3] To prevent premature drying, linseed oil-based products (oil paints, putty) are stored in airtight containers.

Rags soaked with linseed oil pose fire hazard because they provide a large surface area for rapid oxidation. The oxidation of linseed oil is exothermic, which may lead to spontaneous combustion. [4] In 1991, One Meridian Plaza, in Philadelphia, was severely damaged in a fire, in which three firefighters perished, thought to be caused by rags soaked with linseed oil. [5]

Applications

Most applications of linseed oil exploit its drying properties, i.e., the initial material is liquid or at least pliable and the aged material is rigid but not brittle. The water-repelling (hydrophobic) nature of the resulting hydrocarbon-based material is advantageous. [3]

Paint binder

"Your country needs flax .." U.S. WWII poster soliciting linseed oil for use in paint "YOUR COUNTRY NEEDS FLAX, AND WILL PAY WELL FOR IT." - NARA - 516250.jpg
"Your country needs flax .." U.S. WWII poster soliciting linseed oil for use in paint
A can of French linseed oil Fransk Linolja - 2021.jpg
A can of French linseed oil

Linseed oil is the carrier used in oil paint. It can also be used as a painting medium, making oil paints more fluid, transparent and glossy. It is available in varieties such as cold-pressed, alkali-refined, sun-bleached, sun-thickened, and polymerised (stand oil). The introduction of linseed oil was a significant advance in the technology of oil painting.[ citation needed ]

Putty

Traditional glazing putty, consisting of a paste of chalk powder and linseed oil, is a sealant for glass windows that hardens within a few weeks of application and can then be painted over. The durability of putty is owed to the drying properties of linseed oil.[ citation needed ]

Wood finish

When used as a wood finish, linseed oil dries slowly and shrinks little upon hardening. A linseed oil finish is easily scratched and liquid water penetrates a linseed oil finish in mere minutes, and water vapour bypasses it almost completely. [6] Garden furniture treated with linseed oil may develop mildew. Oiled wood may be yellowish and is likely to darken with age. Even though the oil feels dry to the touch, studies show linseed oil does not fully cure. [7]

Linseed oil is a common finish for wooden items, though very fine finish may require months to obtain. Studies show the fatty-acid structure of linseed oil has problems cross-linking and oxidizing, frequently turning black. [8]

Gilding

Boiled linseed oil is used as sizing in traditional oil gilding to adhere sheets of gold leaf to a substrate (parchment, canvas, Armenian bole, etc.). It has a much longer working time than water-based size and gives a firm smooth surface that is adhesive enough in the first 12–24 hours after application to cause the gold to attach firmly to the intended surface.[ citation needed ]

Linoleum

Linseed oil is used to bind wood dust, cork particles, and related materials in the manufacture of the floor covering linoleum. After its invention in 1860 by Frederick Walton, linoleum, or "lino" for short, was a common form of domestic and industrial floor covering from the 1870s until the 1970s, when it was largely replaced by PVC ("vinyl") floor coverings. [9] However, since the 1990s, linoleum is returning to favor, being considered more environmentally sound than PVC. [10] Linoleum has given its name to the printmaking technique linocut, in which a relief design is cut into the smooth surface and then inked and used to print an image. The results are similar to those obtained by woodcut printing.[ citation needed ]

Nutritional supplement and food

Raw cold-pressed linseed oil – commonly known as flax seed oil in nutritional contexts – is easily oxidized, and rapidly becomes rancid, with an unpleasant odour, unless refrigerated. Linseed oil is not generally recommended for use in cooking. In one study, the content of alpha-linolenic acid (ALA) in whole flaxseeds did not decrease after heating the seeds to temperatures of up to 178 °C (352.4 °F) for one and a half hours. [11]

Linseed oil is an edible oil in demand as a dietary supplement, as a source of α-linolenic acid, an omega-3 fatty acid. In parts of Europe, it is traditionally eaten with potatoes and quark.[ citation needed ]

Food-grade flaxseed oil is cold-pressed, obtained without solvent extraction, in the absence of oxygen, and marketed as edible flaxseed oil. Fresh, refrigerated and unprocessed, linseed oil is used as a nutritional supplement and is a traditional European ethnic food, highly regarded for its nutty flavor. Regular flaxseed oil contains between 57% and 71% polyunsaturated fats (alpha-linolenic acid, linoleic acid). [12] Plant breeders have developed flaxseed with both higher ALA (70%) [12] and very low ALA content (< 3%). [13] The USFDA granted generally recognized as safe (GRAS) status for high alpha linolenic flaxseed oil. [14]

Nutrient content

Typical fatty acid content % [15]  % European [16]
Palmitic acid 6.04.0–6.0
Stearic acid 2.52.0–3.0
Arachidic acid 0.50–0.5
Palmitoleic acid -0–0.5
Oleic acid 19.010.0–22.0
Eicosenoic acid -0–0.6
Linoleic acid 24.112.0–18.0
Alpha-linolenic acid 47.456.0–71.0
Other0.5-

Nutrition information from the Flax Council of Canada. [17]

Per 1 tbsp (14 g)

Flax seed oil contains no significant amounts of protein, carbohydrates or fibre.

Comparison to other vegetable oils

Properties of vegetable oils [18] [19]
The nutritional values are expressed as percent (%) by mass of total fat.
TypeProcessing
treatment [20] 		Saturated
fatty acids		 Monounsaturated
fatty acids		 Polyunsaturated
fatty acids		 Smoke point
Total [18] Oleic
acid
(ω−9)		Total [18] α-Linolenic
acid
(ω−3)		 Linoleic
acid
(ω−6)		 ω−6:3
ratio
Avocado [21] 11.670.652–66
[22] 		13.5112.512.5:1250 °C (482 °F) [23]
Brazil nut [24] 24.832.731.342.00.141.9419:1208 °C (406 °F) [25]
Canola [26] 7.463.361.828.19.118.62:1204 °C (400 °F) [27]
Coconut [28] 82.56.361.70.0191.6888:1175 °C (347 °F) [25]
Corn [29] 12.927.627.354.715858:1232 °C (450 °F) [27]
Cottonseed [30] 25.917.81951.915454:1216 °C (420 °F) [27]
Cottonseed [31] hydrogenated 93.61.50.60.20.31.5:1
Flaxseed/linseed [32] 9.018.41867.853130.2:1107 °C (225 °F)
Grape seed  10.414.814.3  74.90.1574.7very high216 °C (421 °F) [33]
Hemp seed [34] 7.09.09.082.022.054.02.5:1166 °C (330 °F) [35]
High-oleic safflower oil [36] 7.575.275.212.8012.8very high212 °C (414 °F) [25]
Olive (extra virgin) [37] 13.873.071.310.50.79.814:1193 °C (380 °F) [25]
Palm [38] 49.337.0409.30.29.145.5:1235 °C (455 °F)
Palm [39] hydrogenated88.25.70
Peanut [40] 16.257.155.419.90.31819.661.6:1232 °C (450 °F) [27]
Rice bran oil 2538.438.436.62.234.4 [41] 15.6:1232 °C (450 °F) [42]
Sesame [43] 14.239.739.341.70.341.3138:1
Soybean [44] 15.622.822.657.77517.3:1238 °C (460 °F) [27]
Soybean [45] partially hydrogenated 14.943.042.537.62.634.913.4:1
Sunflower [46] 8.9963.462.920.70.1620.5128:1227 °C (440 °F) [27]
Walnut oil [47] unrefined9.122.822.263.310.452.95:1160 °C (320 °F) [48]

Additional uses

Modified linseed oils

Stand oil

Stand oil is generated by heating linseed oil near 300 °C for a few days in the complete absence of air. Under these conditions, the polyunsaturated fatty esters convert to conjugated dienes, which then undergo Diels-Alder reactions, leading to crosslinking. The product, which is highly viscous, gives highly uniform coatings that "dry" to more elastic coatings than linseed oil itself. Soybean oil can be treated similarly, but converts more slowly. On the other hand, tung oil converts very quickly, being complete in minutes at 260 °C. Coatings prepared from stand oils are less prone to yellowing than are coatings derived from the parent oils. [51]

Boiled linseed oil

Boiled linseed oil is a combination of raw linseed oil, stand oil (see above), and metallic oil drying agents (catalysts to accelerate drying). [51] In the Medieval era, linseed oil was boiled with lead oxide (litharge) to give a product called boiled linseed oil. [52] [ page needed ] The lead oxide forms lead "soaps" (lead oxide is alkaline) that promote hardening (polymerisation) of linseed oil by reaction with atmospheric oxygen. Heating shortens its drying time.[ citation needed ]

Raw linseed oil

Raw linseed oil is the base oil, unprocessed and without driers or thinners. It is mostly used as a feedstock for making a boiled oil. It does not cure sufficiently well or quickly to be regarded as a drying oil. [53] Raw linseed is sometimes used for oiling cricket bats to increase surface friction for better ball control. [54] It was also used to treat leather flat belt drives to reduce slipping.[ citation needed ]

See also

Related Research Articles

<span class="mw-page-title-main">Flax</span> Flowering plant in the family Linaceae

Flax, also known as common flax or linseed, is a flowering plant, Linum usitatissimum, in the family Linaceae. It is cultivated as a food and fiber crop in regions of the world with temperate climates. In 2022, France produced 75% of the world's supply of flax.

α-Linolenic acid Chemical compound

α-Linolenic acid, also known as alpha-linolenic acid (ALA), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils.

<span class="mw-page-title-main">Vegetable oil</span> Oil extracted from seeds or from other parts of plants

Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of edible plants. Like animal fats, vegetable fats are mixtures of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed oils, or fats from seeds. Olive oil, palm oil, and rice bran oil are examples of fats from other parts of plants. In common usage, vegetable oil may refer exclusively to vegetable fats which are liquid at room temperature. Vegetable oils are usually edible.

<span class="mw-page-title-main">Coconut oil</span> Edible oil derived from coconut

Coconut oil is an edible oil derived from the kernels, meat, and milk of the coconut palm fruit. Coconut oil is a white solid fat below around 25 °C (77 °F), and a clear thin liquid oil at higher temperatures. Unrefined varieties have a distinct coconut aroma. Coconut oil is used as a food oil, and in industrial applications for cosmetics and detergent production. The oil is rich in medium-chain fatty acids.

A saturated fat is a type of fat in which the fatty acid chains have all single bonds between the carbon atoms. A fat known as a glyceride is made of two kinds of smaller molecules: a short glycerol backbone and fatty acids that each contain a long linear or branched chain of carbon (C) atoms. Along the chain, some carbon atoms are linked by single bonds (-C-C-) and others are linked by double bonds (-C=C-). A double bond along the carbon chain can react with a pair of hydrogen atoms to change into a single -C-C- bond, with each H atom now bonded to one of the two C atoms. Glyceride fats without any carbon chain double bonds are called saturated because they are "saturated with" hydrogen atoms, having no double bonds available to react with more hydrogen.

<span class="mw-page-title-main">Hemp oil</span> Oil from hemp seeds

Hemp oil is oil obtained by pressing hemp seeds. Cold pressed, unrefined hemp oil is dark to clear light green in color, with a nutty flavor. The darker the color, the grassier the flavour. It should not be confused with hash oil, a tetrahydrocannabinol-containing oil made from the Cannabis flower.

<span class="mw-page-title-main">Grape seed oil</span> Liquid fat derived from grape seeds

Grape seed oil is a vegetable oil derived from the seeds of grapes. Grape seeds are a winemaking by-product, and oil made from the seeds is commonly used as an edible oil.

<span class="mw-page-title-main">Cottonseed oil</span> Cooking oil

Cottonseed oil is cooking oil from the seeds of cotton plants of various species, mainly Gossypium hirsutum and Gossypium herbaceum, that are grown for cotton fiber, animal feed, and oil.

<span class="mw-page-title-main">Oleic acid</span> Monounsaturated omega-9 fatty acid

Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish due to the presence of impurities. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9, and a main product of Δ9-desaturase. It has the formula CH3−(CH2)7−CH=CH−(CH2)7−COOH. The name derives from the Latin word oleum, which means oil. It is the most common fatty acid in nature. The salts and esters of oleic acid are called oleates. It is a common component of oils, and thus occurs in many types of food, as well as in soap.

<span class="mw-page-title-main">Omega-6 fatty acid</span> Fatty acids where the sixth bond is double

Omega−6 fatty acids are a family of polyunsaturated fatty acids that have in common a final carbon-carbon double bond in the n−6 position, that is, the sixth bond, counting from the methyl end.

Linoleic acid (LA) is an organic compound with the formula HOOC(CH2)7CH=CHCH2CH=CH(CH2)4CH3. Both alkene groups are cis. It is a fatty acid sometimes denoted 18:2 (n−6) or 18:2 cis-9,12. A linoleate is a salt or ester of this acid.

Linola is the trademark name of solin, cultivated forms of flax bred for producing linseed oil with a low alpha-linolenic acid content. Linola was developed in the early 1990s by the Commonwealth Scientific and Industrial Research Organisation (CSIRO). It was developed and released in Australia in 1992 and first commercially grown in 1994. Australian Linola varieties are named after Australian lakes.

<span class="mw-page-title-main">Rice bran oil</span> Oil extracted from the hard outer brown layer of rice

Rice bran oil is the oil extracted from the hard outer brown layer of rice called bran. It is known for its high smoke point of 232 °C (450 °F) and mild flavor, making it suitable for high-temperature cooking methods such as stir frying and deep frying. It is popular as a cooking oil in East Asia, the Indian subcontinent, and Southeast Asia including India, Nepal, Bangladesh, Indonesia, Japan, Southern China and Malaysia.

<span class="mw-page-title-main">Corn oil</span> Oil from the seeds of corn

Corn oil or maize oil (British) is oil extracted from the germ of corn (maize). Its main use is in cooking, where its high smoke point makes refined corn oil a valuable frying oil. It is also a key ingredient in some margarines. Corn oil is generally less expensive than most other types of vegetable oils.

<span class="mw-page-title-main">Soybean oil</span> Oil obtained from seeds of soya plant

Soybean oil is a vegetable oil extracted from the seeds of the soybean. It is one of the most widely consumed cooking oils and the second most consumed vegetable oil. As a drying oil, processed soybean oil is also used as a base for printing inks and oil paints.

<span class="mw-page-title-main">Sunflower oil</span> Oil pressed from the seed of Helianthus annuus

Sunflower oil is the non-volatile oil pressed from the seeds of the sunflower. Sunflower oil is commonly used in food as a frying oil, and in cosmetic formulations as an emollient.

<span class="mw-page-title-main">Polyunsaturated fat</span> Type of fatty acid defined by molecular bonds

In biochemistry and nutrition, a polyunsaturated fat is a fat that contains a polyunsaturated fatty acid, which is a subclass of fatty acid characterized by a backbone with two or more carbon–carbon double bonds. Some polyunsaturated fatty acids are essentials. Polyunsaturated fatty acids are precursors to and are derived from polyunsaturated fats, which include drying oils.

<span class="mw-page-title-main">Avocado oil</span> Edible oil pressed from the pulp of avocados

Avocado oil is an edible oil extracted from the pulp of avocados, the fruit of Persea americana. It is used as an edible oil both raw and for cooking, where it is noted for its high smoke point. It is also used for lubrication and in cosmetics.

<span class="mw-page-title-main">Cooking oil</span> Oil consumed by humans, of vegetable or animal origin

Cooking oil is a plant or animal liquid fat used in frying, baking, and other types of cooking. Oil allows higher cooking temperatures than water, making cooking faster and more flavorful, while likewise distributing heat, reducing burning and uneven cooking. It sometimes imparts its own flavor. Cooking oil is also used in food preparation and flavoring not involving heat, such as salad dressings and bread dips.

<span class="mw-page-title-main">Rapeseed oil</span> Vegetable oil

Rapeseed oil is one of the oldest known vegetable oils. There are both edible and industrial forms produced from rapeseed, the seed of several cultivars of the plant family Brassicaceae. Historically, it was restricted as a food oil due to its content of erucic acid. Laboratory studies about this acid have shown damage to the cardiac muscle of laboratory animals in high quantities. It also imparts a bitter taste, and glucosinolates, which made many parts of the plant less nutritious in animal feed. Rapeseed oil from standard cultivars can contain up to 54% erucic acid.

References

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