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76-431: Purified storax contains circa 33 to 50% storesin, an alcoholic resin , both free and as cinnamic esters. It contains 5 to 15% cinnamic acid , 5 to 15% cinnamyl cinnamate , circa 10% phenylpropyl cinnamate ; small amounts of ethyl cinnamate , benzyl cinnamate , and styrene . Some may contain traces of vanillin . Some sources report a resin containing triterpenic acids ( oleanolic and 3-epioleanolic acids). Storax has

152-425: A values of around 16–19, alcohols are, in general, slightly weaker acids than water . With strong bases such as sodium hydride or sodium they form salts called alkoxides , with the general formula RO M (where R is an alkyl and M is a metal ). The acidity of alcohols is strongly affected by solvation . In the gas phase, alcohols are more acidic than in water. In DMSO , alcohols (and water) have

228-406: A catalyst , such as concentrated sulfuric acid: Methanol Moderately toxic for small animals – Highly toxic to large animals and humans (in high concentrations) – May be fatal/ lethal or cause blindness and damage to the liver , kidneys , and heart if swallowed – Toxicity effects from repeated over exposure have an accumulative effect on the central nervous system , especially

304-416: A chromium and manganese oxide catalyst with extremely vigorous conditions: pressures ranging from 50 to 220 atm , and temperatures up to 450 °C. Modern methanol production has been made more efficient through use of catalysts (commonly copper) capable of operating at lower pressures. The modern low pressure methanol (LPM) process was developed by ICI in the late 1960s US 3326956   with

380-483: A denaturant for ethanol, the product being known as "denatured alcohol" or "methylated spirit". This was commonly used during the US prohibition to discourage consumption of bootlegged liquor, and ended up causing several deaths. It is sometimes used as a fuel in alcohol lamps, portable fire pits and camping stoves. Methanol is used as a solvent and as an antifreeze in pipelines and windshield washer fluid . Methanol

456-473: A hydroxyl group , often abbreviated as MeOH ). It is a light, volatile , colorless and flammable liquid with a distinctive alcoholic odor similar to that of ethanol (potable alcohol), but is more acutely toxic than the latter. Methanol acquired the name wood alcohol because it was once produced chiefly by the destructive distillation of wood . Today, methanol is mainly produced industrially by hydrogenation of carbon monoxide . Methanol consists of

532-505: A dinuclear active site is proposed in the sMMO enzyme, whereas a mononuclear iron ( alpha-oxygen ) is proposed in the Fe-zeolite. Global emissions of methanol by plants are estimated at between 180 and 250 million tons per year. This is between two and three times larger than man-made industrial production of methanol. As of 2023, 0.2% of global methanol production is produced in ways that have relatively low greenhouse gas emissions; this

608-401: A favorite of hikers who spend extended time in the wilderness. Similarly, the alcohol can be gelled to reduce risk of leaking or spilling, as with the brand " Sterno ". Methanol is mixed with water and injected into high performance diesel and gasoline engines for an increase of power and a decrease in intake air temperature in a process known as water methanol injection . Methanol is used as

684-458: A linear alcohol: Such processes give fatty alcohols , which are useful for detergents. Some low molecular weight alcohols of industrial importance are produced by the addition of water to alkenes. Ethanol, isopropanol, 2-butanol, and tert -butanol are produced by this general method. Two implementations are employed, the direct and indirect methods. The direct method avoids the formation of stable intermediates, typically using acid catalysts. In

760-588: A marker for such regions. It is detected through its spectral emission lines. In 2006, astronomers using the MERLIN array of radio telescopes at Jodrell Bank Observatory discovered a large cloud of methanol in space 0.463 terametres (288 million miles) across. In 2016, astronomers detected methanol in a planet-forming disc around the young star TW Hydrae using the Atacama Large Millimeter Array radio telescope. In their embalming process,

836-419: A mean of 4.5  ppm in the exhaled breath of test subjects. The mean endogenous methanol in humans of 0.45 g/d may be metabolized from pectin found in fruit; one kilogram of apple produces up to 1.4 g of pectin (0.6 g of methanol.) Methanol is produced by anaerobic bacteria and phytoplankton . Methanol is also found in abundant quantities in star-forming regions of space and is used in astronomy as

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912-413: A methyl group linked to a polar hydroxyl group. With more than 20 million tons produced annually, it is used as a precursor to other commodity chemicals , including formaldehyde , acetic acid , methyl tert-butyl ether , methyl benzoate , anisole , peroxyacids , as well as a host of more specialised chemicals. Small amounts of methanol are present in normal, healthy human individuals. One study found

988-500: A number of Latin works, and by the end of the thirteenth century, it had become a widely known substance among Western European chemists. The works of Taddeo Alderotti (1223–1296) describe a method for concentrating alcohol involving repeated fractional distillation through a water-cooled still, by which an alcohol purity of 90% could be obtained. The medicinal properties of ethanol were studied by Arnald of Villanova (1240–1311 CE) and John of Rupescissa ( c.  1310 –1366),

1064-596: A p K a of around 29–32. As a consequence, alkoxides (and hydroxide) are powerful bases and nucleophiles (e.g., for the Williamson ether synthesis ) in this solvent. In particular, RO or HO in DMSO can be used to generate significant equilibrium concentrations of acetylide ions through the deprotonation of alkynes (see Favorskii reaction ). Tertiary alcohols react with hydrochloric acid to produce tertiary alkyl chloride . Primary and secondary alcohols are converted to

1140-460: A patent. According to Bozzano and Manenti, BASF's process was first utilized in Leuna , Germany in 1923. Operating conditions consisted of "high" temperatures (between 300 and 400 °C) and pressures (between 250 and 350 atm) with a zinc / chromium oxide catalyst. US patent 1,569,775 ( US 1569775   ) was applied for on 4 September 1924 and issued on 12 January 1926 to BASF; the process used

1216-407: A pleasant, floral/lilac, leathery, balsamic smell. Storax and its derivatives ( resinoid , essential oil , absolute ) are used as flavors, fragrances, and in pharmaceuticals ( Friar's Balsam ). American storax resin ( Liquidambar styraciflua ) is chewed like gum to freshen breath and clean teeth. Mnesimachus , Aristotle , Theophrastus ( Historia Plantarum ), Herodotus , and Strabo mention

1292-476: A small amount of pilot fuel (dual fuel). In China, methanol fuels industrial boilers, which are used extensively to generate heat and steam for various industrial applications and residential heating. Its use is displacing coal, which is under pressure from increasingly stringent environmental regulations. Direct-methanol fuel cells are unique in their low temperature, atmospheric pressure operation, which lets them be greatly miniaturized. This, combined with

1368-496: A spice in his book Murūdj al-dhahab ( Meadows of Gold ). Chao Ju-Kuan , a 13th century trade commissioner in Fukien province, described liquid storax gum as a product of Ta-shï (the Arabs ). Linnaeus , who determined the scientific names of plants, thought that storax was extracted from the tree called in modern Hebrew livneh refu'i which he termed Styrax officinalis . However in

1444-532: Is "generally regarded as safe" ( GRAS ), but at low levels, for example, circa 15 ppm in candy and 25 ppm in baked goods. Alcohol (chemistry) In chemistry , an alcohol (from Arabic al-kuḥl  'the kohl '), is a type of organic compound that carries at least one hydroxyl ( −OH ) functional group bound to a saturated carbon atom. Alcohols range from the simple, like methanol and ethanol , to complex, like sugars and cholesterol . The presence of an OH group strongly modifies

1520-400: Is an alcohol. However, some compounds that contain hydroxyl functional groups have trivial names that do not include the suffix -ol or the prefix hydroxy- , e.g. the sugars glucose and sucrose . IUPAC nomenclature is used in scientific publications, and in writings where precise identification of the substance is important. In naming simple alcohols, the name of the alkane chain loses

1596-465: Is attested in Arabic works attributed to al-Kindī ( c.  801 –873 CE) and to al-Fārābī ( c.  872 –950), and in the 28th book of al-Zahrāwī 's (Latin: Abulcasis, 936–1013) Kitāb al-Taṣrīf (later translated into Latin as Liber servatoris ). In the twelfth century, recipes for the production of aqua ardens ("burning water", i.e., alcohol) by distilling wine with salt started to appear in

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1672-420: Is characterized by high selectivity (>99.8%). The production of synthesis gas from methane produces three moles of hydrogen for every mole of carbon monoxide, whereas the synthesis consumes only two moles of hydrogen gas per mole of carbon monoxide. One way of dealing with the excess hydrogen is to inject carbon dioxide into the methanol synthesis reactor, where it, too, reacts to form methanol according to

1748-408: Is formed. Tertiary alcohols are eliminated easily at just above room temperature, but primary alcohols require a higher temperature. This is a diagram of acid catalyzed dehydration of ethanol to produce ethylene : [REDACTED] A more controlled elimination reaction requires the formation of the xanthate ester . Tertiary alcohols react with strong acids to generate carbocations. The reaction

1824-404: Is its ready biodegradability and low environmental toxicity. It does not persist in either aerobic (oxygen-present) or anaerobic (oxygen-absent) environments. The half-life for methanol in groundwater is just one to seven days, while many common gasoline components have half-lives in the hundreds of days (such as benzene at 10–730 days). Since methanol is miscible with water and biodegradable, it

1900-405: Is known as "green" methanol. Most green methanol is produced from gasification of biomass . Syngas is produced from biomass gasification and further converted into green methanol. Another method of producing green methanol involves combining hydrogen, carbon dioxide, and a catalyst under high heat and pressure. To be classified as green methanol, the hydrogen must be green hydrogen , which

1976-468: Is less acutely toxic. All alcohols are mild skin irritants. Methanol and ethylene glycol are more toxic than other simple alcohols. Their metabolism is affected by the presence of ethanol, which has a higher affinity for liver alcohol dehydrogenase . In this way, methanol will be excreted intact in urine. In general, the hydroxyl group makes alcohols polar . Those groups can form hydrogen bonds to one another and to most other compounds. Owing to

2052-421: Is more easily oxidized than is the feedstock methane, so the reactions tend not to be selective. Some strategies exist to circumvent this problem. Examples include Shilov systems and Fe- and Cu-containing zeolites. These systems do not necessarily mimic the mechanisms employed by metalloenzymes , but draw some inspiration from them. Active sites can vary substantially from those known in the enzymes. For example,

2128-800: Is produced using renewable electricity. Additionally, the carbon dioxide in this process must be a product of carbon capture and storage or direct air capture or biomass of recent origin. Some definitions of green methanol specify that the carbon dioxide must be captured during the burning of bioenergy . Methanol is available commercially in various purity grades. Commercial methanol is generally classified according to ASTM purity grades A and AA. Both grade A and grade AA purity are 99.85% methanol by weight. Grade "AA" methanol contains trace amounts of ethanol as well. Methanol for chemical use normally corresponds to Grade AA. In addition to water, typical impurities include acetone and ethanol (which are very difficult to separate by distillation). UV-vis spectroscopy

2204-415: Is related to their dehydration, e.g. isobutylene from tert -butyl alcohol. A special kind of dehydration reaction involves triphenylmethanol and especially its amine-substituted derivatives. When treated with acid, these alcohols lose water to give stable carbocations, which are commercial dyes. Alcohol and carboxylic acids react in the so-called Fischer esterification . The reaction usually requires

2280-512: Is that captured CO 2 and hydrogen sourced from electrolysis could be used, removing the dependence on fossil fuels. The catalytic conversion of methane to methanol is effected by enzymes including methane monooxygenases . These enzymes are mixed-function oxygenases, i.e. oxygenation is coupled with production of water and NAD : Both Fe- and Cu-dependent enzymes have been characterized. Intense but largely fruitless efforts have been undertaken to emulate this reactivity. Methanol

2356-581: Is the asymmetric reduction of β-keto-esters. Alkenes engage in an acid catalyzed hydration reaction using concentrated sulfuric acid as a catalyst that gives usually secondary or tertiary alcohols. Formation of a secondary alcohol via alkene reduction and hydration is shown: The hydroboration-oxidation and oxymercuration-reduction of alkenes are more reliable in organic synthesis. Alkenes react with N -bromosuccinimide and water in halohydrin formation reaction . Amines can be converted to diazonium salts , which are then hydrolyzed. With aqueous p K

Storax balsam - Misplaced Pages Continue

2432-508: Is the focus on this article, the following are most important industrial alcohols: Methanol is the most common industrial alcohol, with about 12 million tons/y produced in 1980. The combined capacity of the other alcohols is about the same, distributed roughly equally. With respect to acute toxicity, simple alcohols have low acute toxicities . Doses of several milliliters are tolerated. For pentanols , hexanols , octanols , and longer alcohols, LD50 range from 2–5 g/kg (rats, oral). Ethanol

2508-403: Is unlikely to accumulate in groundwater, surface water, air or soil. Methanol is occasionally used to fuel internal combustion engines . It burns forming carbon dioxide and water: Methanol fuel has been proposed for ground transportation. The chief advantage of a methanol economy is that it could be adapted to gasoline internal combustion engines with minimum modification to the engines and to

2584-634: Is widely used in many areas, especially polymers . The conversion entails oxidation: Acetic acid can be produced from methanol. Methanol and isobutene are combined to give methyl tert -butyl ether (MTBE). MTBE is a major octane booster in gasoline. Condensation of methanol to produce hydrocarbons and even aromatic systems is the basis of several technologies related to gas to liquids . These include methanol-to-hydrocarbons (MtH), methanol to gasoline (MtG), methanol to olefins (MtO), and methanol to propylene (MtP). These conversions are catalyzed by zeolites as heterogeneous catalysts . The MtG process

2660-461: The International Union of Pure and Applied Chemistry (IUPAC) chemical name of all substances where the hydroxyl group is the functional group with the highest priority. When a higher priority group is present in the compound, the prefix hydroxy- is used in its IUPAC name. The suffix -ol in non-IUPAC names (such as paracetamol or cholesterol ) also typically indicates that the substance

2736-476: The Ziegler process , linear alcohols are produced from ethylene and triethylaluminium followed by oxidation and hydrolysis. An idealized synthesis of 1-octanol is shown: The process generates a range of alcohols that are separated by distillation . Many higher alcohols are produced by hydroformylation of alkenes followed by hydrogenation. When applied to a terminal alkene , as is common, one typically obtains

2812-514: The ancient Egyptians used a mixture of substances, including methanol, which they obtained from the pyrolysis of wood. Pure methanol, however, was first isolated in 1661 by Robert Boyle , when he produced it via the distillation of buxus (boxwood). It later became known as "pyroxylic spirit". In 1834, the French Chemists Jean-Baptiste Dumas and Eugene Peligot determined its elemental composition. They also introduced

2888-592: The in English. The second part of the word ( kuḥl ) has several antecedents in Semitic languages , ultimately deriving from the Akkadian 𒎎𒋆𒁉𒍣𒁕 ( guḫlum ), meaning stibnite or antimony . Like its antecedents in Arabic and older languages, the term alcohol was originally used for the very fine powder produced by the sublimation of the natural mineral stibnite to form antimony trisulfide Sb 2 S 3 . It

2964-400: The optic nerve – Symptoms may be delayed, become severe after 12 to 18 hours, and linger for several days after exposure 385 °C (725 °F; 658 K) Methanol (also called methyl alcohol and wood spirit , amongst other names) is an organic chemical compound and the simplest aliphatic alcohol , with the chemical formula C H 3 O H (a methyl group linked to

3040-458: The 18th century and was extended to the class of substances so-called as "alcohols" in modern chemistry after 1850. The term ethanol was invented in 1892, blending " ethane " with the "-ol" ending of "alcohol", which was generalized as a libfix . The term alcohol originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic drinks . The suffix -ol appears in

3116-544: The US In addition, low levels of methanol were blended in gasoline fuels sold in Europe during much of the 1980s and early-1990s. Automakers stopped building methanol FFVs by the late-1990s, switching their attention to ethanol-fueled vehicles. While the methanol FFV program was a technical success, rising methanol pricing in the mid- to late-1990s during a period of slumping gasoline pump prices diminished interest in methanol fuels . In

Storax balsam - Misplaced Pages Continue

3192-505: The biblical balm, though other sources conclude that the biblical balm is Balsam ( opobalsamum ). This species originated in the Southern regions of Mesopotamia, present day Iraq and in particular Babylon. Babylonians used it for respiratory related diseases. 8 In the nineteenth century, styrene was isolated by distillation of storax balsam. In North Africa, for mystical purposes, women burn benzoin and storax in potsherds. Storax resin

3268-482: The corresponding chlorides using thionyl chloride and various phosphorus chloride reagents. [REDACTED] Primary and secondary alcohols, likewise, convert to alkyl bromides using phosphorus tribromide , for example: In the Barton-McCombie deoxygenation an alcohol is deoxygenated to an alkane with tributyltin hydride or a trimethylborane -water complex in a radical substitution reaction. Meanwhile,

3344-459: The early 1970s, a process was developed by Mobil for producing gasoline fuel from methanol. Between the 1960s and 1980s methanol emerged as a precursor to the feedstock chemicals acetic acid and acetic anhydride . These processes include the Monsanto acetic acid synthesis , Cativa process , and Tennessee Eastman acetic anhydride process . Methanol is primarily converted to formaldehyde, which

3420-631: The elimination (alkene) product instead. Grignard reagents react with carbonyl groups to give secondary and tertiary alcohols. Related reactions are the Barbier reaction and the Nozaki-Hiyama reaction . Aldehydes or ketones are reduced with sodium borohydride or lithium aluminium hydride (after an acidic workup). Another reduction using aluminium isopropoxide is the Meerwein-Ponndorf-Verley reduction . Noyori asymmetric hydrogenation

3496-450: The equation In terms of mechanism, the process occurs via initial conversion of CO into CO 2 , which is then hydrogenated : where the H 2 O byproduct is recycled via the water-gas shift reaction This gives an overall reaction which is the same as listed above. In a process closely related to methanol production from synthesis gas, a feed of hydrogen and CO 2 can be used directly. The main advantage of this process

3572-473: The first process that could be used to produce methanol synthetically in 1905. This process suggested that carbon dioxide and hydrogen could be reacted to produce methanol. German chemists Alwin Mittasch and Mathias Pier, working for Badische-Anilin & Soda-Fabrik (BASF), developed a means to convert synthesis gas (a mixture of carbon monoxide , carbon dioxide , and hydrogen ) into methanol and received

3648-437: The form RR'CHOH, the simplest of which is 2-propanol ( R = R' = CH 3 ). For the tertiary alcohols, the general form is RR'R"COH. The simplest example is tert -butanol (2-methylpropan-2-ol), for which each of R, R', and R" is CH 3 . In these shorthands, R, R', and R" represent substituents , alkyl or other attached, generally organic groups. Alcohols have a long history of myriad uses. For simple mono-alcohols, which

3724-525: The formula was C 4 H 8 O 4 or (CH) 4 (H 2 O) 2 ). The term "methyl" was derived in about 1840 by back-formation from "methylene", and was then applied to describe "methyl alcohol". This was shortened to "methanol" in 1892 by the International Conference on Chemical Nomenclature . The suffix -yl , which, in organic chemistry , forms names of carbon groups, is from the word methyl . French chemist Paul Sabatier presented

3800-791: The hydrocarbon hexane , and 34.6 °C for diethyl ether . Alcohols occur widely in nature, as derivatives of glucose such as cellulose and hemicellulose , and in phenols and their derivatives such as lignin . Starting from biomass , 180 billion tons/y of complex carbohydrates (sugar polymers) are produced commercially (as of 2014). Many other alcohols are pervasive in organisms, as manifested in other sugars such as fructose and sucrose , in polyols such as glycerol , and in some amino acids such as serine . Simple alcohols like methanol, ethanol, and propanol occur in modest quantities in nature, and are industrially synthesized in large quantities for use as chemical precursors, fuels, and solvents. Many alcohols are produced by hydroxylation , i.e.,

3876-536: The hydroxyl group is bonded to the end or middle carbon on the straight propane chain. As described under systematic naming, if another group on the molecule takes priority, the alcohol moiety is often indicated using the "hydroxy-" prefix. In archaic nomenclature, alcohols can be named as derivatives of methanol using "-carbinol" as the ending. For instance, (CH 3 ) 3 COH can be named trimethylcarbinol . Alcohols are then classified into primary, secondary ( sec- , s- ), and tertiary ( tert- , t- ), based upon

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3952-432: The indirect method, the alkene is converted to the sulfate ester , which is subsequently hydrolyzed. The direct hydration uses ethylene ( ethylene hydration ) or other alkenes from cracking of fractions of distilled crude oil . Hydration is also used industrially to produce the diol ethylene glycol from ethylene oxide . Ethanol is obtained by fermentation of glucose (which is often obtained from starch ) in

4028-638: The infrastructure that delivers and stores liquid fuel. Its energy density, however, is less than gasoline, meaning more frequent fill ups would be required. However, it is equivalent to super high-octane gasoline in horsepower, and most modern computer-controlled fuel injection systems can already use it. Methanol is an alternative fuel for ships that helps the shipping industry meet increasingly strict emissions regulations. It significantly reduces emissions of sulfur oxides (SOx), nitrogen oxides (NOx) and particulate matter. Methanol can be used with high efficiency in marine diesel engines after minor modifications using

4104-431: The installation of a hydroxy group using oxygen or a related oxidant. Hydroxylation is the means by which the body processes many poisons , converting lipophilic compounds into hydrophilic derivatives that are more readily excreted. Enzymes called hydroxylases and oxidases facilitate these conversions. Many industrial alcohols, such as cyclohexanol for the production of nylon , are produced by hydroxylation. In

4180-431: The isolation of alcohol, even despite the development of more advanced distillation techniques in second- and third-century Roman Egypt . An important recognition, first found in one of the writings attributed to Jābir ibn Ḥayyān (ninth century CE), was that by adding salt to boiling wine, which increases the wine's relative volatility , the flammability of the resulting vapors may be enhanced. The distillation of wine

4256-412: The latter of whom regarded it as a life-preserving substance able to prevent all diseases (the aqua vitae or "water of life", also called by John the quintessence of wine). The word "alcohol" derives from the Arabic kohl ( Arabic : الكحل , romanized :  al-kuḥl ), a powder used as an eyeliner. The first part of the word ( al- ) is the Arabic definite article , equivalent to

4332-535: The light of tests made in Israel it is very doubtful if a sap with medicinal or aromatic qualities can be extracted from this tree. The storax of the ancients was probably extracted from a different tree, seemingly from the Liquidambar orientalis which grows wild in northern Syria, and may even have been grown in Israel; from it is extracted an aromatic sap with healing qualities called storax liquidis . This may possibly be

4408-496: The molecule is classified separately as a phenol and is named using the IUPAC rules for naming phenols. Phenols have distinct properties and are not classified as alcohols. In other less formal contexts, an alcohol is often called with the name of the corresponding alkyl group followed by the word "alcohol", e.g., methyl alcohol, ethyl alcohol. Propyl alcohol may be n -propyl alcohol or isopropyl alcohol , depending on whether

4484-409: The nitrification of sensitive aquifers . Methanol is used as a destaining agent in polyacrylamide gel electrophoresis . Carbon monoxide and hydrogen react over a catalyst to produce methanol. Today, the most widely used catalyst is a mixture of copper and zinc oxides , supported on alumina , as first used by ICI in 1966. At 5–10 MPa (50–100 atm) and 250 °C (482 °F), the reaction

4560-430: The number of carbon atoms connected to the carbon atom that bears the hydroxyl functional group . The respective numeric shorthands 1°, 2°, and 3° are sometimes used in informal settings. The primary alcohols have general formulas RCH 2 OH . The simplest primary alcohol is methanol ( CH 3 OH ), for which R = H, and the next is ethanol, for which R = CH 3 , the methyl group . Secondary alcohols are those of

4636-461: The oxygen atom has lone pairs of nonbonded electrons that render it weakly basic in the presence of strong acids such as sulfuric acid . For example, with methanol: [REDACTED] Upon treatment with strong acids, alcohols undergo the E1 elimination reaction to produce alkenes . The reaction, in general, obeys Zaitsev's Rule , which states that the most stable (usually the most substituted) alkene

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4712-435: The prefix hydroxy- is used, e.g., as in 1-hydroxy-2-propanone ( CH 3 C(O)CH 2 OH ). Compounds having more than one hydroxy group are called polyols . They are named using suffixes -diol, -triol, etc., following a list of the position numbers of the hydroxyl groups, as in propane-1,2-diol for CH 3 CH(OH)CH 2 OH (propylene glycol). In cases where the hydroxy group is bonded to an sp carbon on an aromatic ring ,

4788-413: The presence of the polar OH alcohols are more water-soluble than simple hydrocarbons. Methanol, ethanol, and propanol are miscible in water. 1-Butanol , with a four-carbon chain, is moderately soluble. Because of hydrogen bonding , alcohols tend to have higher boiling points than comparable hydrocarbons and ethers . The boiling point of the alcohol ethanol is 78.29 °C, compared to 69 °C for

4864-542: The presence of yeast. Carbon dioxide is cogenerated. Like ethanol, butanol can be produced by fermentation processes. Saccharomyces yeast are known to produce these higher alcohols at temperatures above 75 °F (24 °C). The bacterium Clostridium acetobutylicum can feed on cellulose (also an alcohol) to produce butanol on an industrial scale. Primary alkyl halides react with aqueous NaOH or KOH to give alcohols in nucleophilic aliphatic substitution . Secondary and especially tertiary alkyl halides will give

4940-454: The properties of hydrocarbons, conferring hydrophilic (water-loving) properties. The OH group provides a site at which many reactions can occur. The flammable nature of the exhalations of wine was already known to ancient natural philosophers such as Aristotle (384–322 BCE), Theophrastus ( c.  371 –287 BCE), and Pliny the Elder (23/24–79 CE). However, this did not immediately lead to

5016-417: The relatively easy and safe storage and handling of methanol, may open the possibility of fuel cell-powered consumer electronics , such as laptop computers and mobile phones. Methanol is also a widely used fuel in camping and boating stoves. Methanol burns well in an unpressurized burner, so alcohol stoves are often very simple, sometimes little more than a cup to hold fuel. This lack of complexity makes them

5092-442: The same time Paracelsus uses the word for a volatile liquid; alcool or alcool vini occurs often in his writings. Bartholomew Traheron , in his 1543 translation of John of Vigo , introduces the word as a term used by "barbarous" authors for "fine powder." Vigo wrote: "the barbarous auctours use alcohol, or (as I fynde it sometymes wryten) alcofoll, for moost fine poudre." The 1657 Lexicon Chymicum , by William Johnson glosses

5168-535: The storax tree and its balsam. In ancient Greece , storax also denoted the spike at the lower end of a spearshaft. Pliny ( Historia Naturalis 12.98, 15.26; 24.24) notes the use of storax as a perfume, while Scribonius Largus drank wine flavored with storax. Ciris mentions storax as a fragrant hair dye. Dioscorides ( De materia medica 1.79) reports its use as incense, similar to frankincense , having expectorant and soothing properties. The 10th century Arab historian al-Masudi listed storax gum ( mayʿa ) as

5244-463: The technology patent long since expired. During World War II , methanol was used as a fuel in several German military rocket designs, under the name M-Stoff , and in a roughly 50/50 mixture with hydrazine , known as C-Stoff . The use of methanol as a motor fuel received attention during the oil crises of the 1970s . By the mid-1990s, over 20,000 methanol " flexible fuel vehicles " (FFV) capable of operating on methanol or gasoline were introduced in

5320-413: The terminal e and adds the suffix -ol , e.g. , as in "ethanol" from the alkane chain name " ethane ". When necessary, the position of the hydroxyl group is indicated by a number between the alkane name and the -ol : propan-1-ol for CH 3 CH 2 CH 2 OH , propan-2-ol for CH 3 CH(OH)CH 3 . If a higher priority group is present (such as an aldehyde , ketone , or carboxylic acid ), then

5396-417: The transesterification of fats and production of biodiesel via transesterification . Methanol is a promising energy carrier because, as a liquid, it is easier to store than hydrogen and natural gas. Its energy density is, however, lower than methane , per kg. Its combustion energy density is 15.6 MJ / L ( LHV ), whereas that of ethanol is 24 and gasoline is 33 MJ/L. Further advantages for methanol

5472-511: The word "methylène" to organic chemistry, forming it from Greek methy = "alcoholic liquid" + hȳlē = "forest, wood, timber, material". "Methylène" designated a "radical" that was about 14% hydrogen by weight and contained one carbon atom. This would be CH 2 , but at the time carbon was thought to have an atomic weight only six times that of hydrogen, so they gave the formula as CH. They then called wood alcohol (l'esprit de bois) "bihydrate de méthylène" (bihydrate because they thought

5548-600: The word as "antimonium sive stibium." By extension, the word came to refer to any fluid obtained by distillation, including "alcohol of wine," the distilled essence of wine. Libavius in Alchymia (1594) refers to " vini alcohol vel vinum alcalisatum ". Johnson (1657) glosses alcohol vini as " quando omnis superfluitas vini a vino separatur, ita ut accensum ardeat donec totum consumatur, nihilque fæcum aut phlegmatis in fundo remaneat ." The word's meaning became restricted to "spirit of wine" (the chemical known today as ethanol ) in

5624-428: Was considered to be the essence or "spirit" of this mineral. It was used as an antiseptic , eyeliner, and cosmetic . Later the meaning of alcohol was extended to distilled substances in general, and then narrowed again to ethanol, when "spirits" was a synonym for hard liquor . Paracelsus and Libavius both used the term alcohol to denote a fine powder, the latter speaking of an alcohol derived from antimony. At

5700-561: Was once commercialized at Motunui in New Zealand. The European Fuel Quality Directive allows fuel producers to blend up to 3% methanol, with an equal amount of cosolvent, with gasoline sold in Europe. In 2019, it is estimated that China used as much as 7 million tons of methanol as transportation fuels, representing over 5% of their fuel pool. Methanol is the precursor to most simple methylamines , methyl halides , and methyl ethers. Methyl esters are produced from methanol, including

5776-510: Was used as an automobile coolant antifreeze in the early 1900s. As of May 2018, methanol was banned in the EU for use in windscreen washing or defrosting due to its risk of human consumption as a result of 2012 Czech Republic methanol poisonings . In some wastewater treatment plants , a small amount of methanol is added to wastewater to provide a carbon food source for the denitrifying bacteria , which convert nitrates to nitrogen gas and reduce

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