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111-600: Biodiesel is a fuel composed of mono-alkyl esters of long-chain fatty acids derived from vegetable oils or animal fats , designated B100, and meeting the requirements of American Society for Testing and Materials ( ASTM International ) D6751. CFAA promotes the common business interests of those seeking to advance the use of biodiesel as a fuel or fuel additive that meets ASTM standards. Members are state, national, and international feedstock and feedstock processor organizations, biodiesel suppliers, fuel marketers and distributors, and technology providers. The governing board

222-476: A carbonyl group C=O, which is a divalent group at C atom, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides , carboxylic acid esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than

333-425: A carboxylic acid ( R−C(=O)−OH ) and an alcohol ( R'−OH ), forming an ester ( R−C(=O)−O−R' ), where R stands for any group (typically hydrogen or organyl) and R ′ stands for organyl group. Organyl esters of carboxylic acids typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones . They perform as high-grade solvents for

444-414: A carcinogen or "probable carcinogen" and is known to increase the risk of heart and respiratory diseases. In principle, a diesel engine does not require any sort of electrical system. However, most modern diesel engines are equipped with an electrical fuel pump, and an electronic engine control unit. However, there is no high-voltage electrical ignition system present in a diesel engine. This eliminates

555-444: A dehydrating agent: The equilibrium constant for such reactions is about 5 for typical esters, e.g., ethyl acetate. The reaction is slow in the absence of a catalyst. Sulfuric acid is a typical catalyst for this reaction. Many other acids are also used such as polymeric sulfonic acids . Since esterification is highly reversible, the yield of the ester can be improved using Le Chatelier's principle : Reagents are known that drive

666-619: A broad array of plastics , plasticizers , resins , and lacquers , and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties . Esters of phosphoric acid form the backbone of DNA molecules. Esters of nitric acid , such as nitroglycerin , are known for their explosive properties. There are compounds in which an acidic hydrogen of acids mentioned in this article are not replaced by an organyl, but by some other group. According to some authors, those compounds are esters as well, especially when

777-955: A combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s -trans (i.e. E ) conformation due to their cyclic structure. Esters derived from carboxylic acids and alcohols are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight. Esters are generally identified by gas chromatography, taking advantage of their volatility. IR spectra for esters feature an intense sharp band in

888-498: A cooperative and voluntary program for the accreditation of producers and marketers of biodiesel fuel called BQ-9000. The program is a unique combination of the ASTM standard for biodiesel, ASTM D6751, and a quality systems program, which includes storage, sampling, testing, blending, shipping, distribution, and fuel management practices. BQ-9000 is open to any biodiesel manufacturer, marketer, or distributor of biodiesel and biodiesel blends in

999-448: A diesel engine drops at lower loads, however, it does not drop quite as fast as the Otto (spark ignition) engine's. Diesel engines are combustion engines and, therefore, emit combustion products in their exhaust gas . Due to incomplete combustion, diesel engine exhaust gases include carbon monoxide , hydrocarbons , particulate matter , and nitrogen oxides pollutants. About 90 per cent of

1110-599: A feedstock-neutral industry association – a move voted for by the organization’s farmer members. Access to economical feedstock sources remains a focal point for the industry, and CFAA continues to be a strong advocate in Washington, D.C. for increased investment in feedstock research. Although its headquarters are located in Jefferson City , Missouri , CFAA has a federal affairs office in Washington, D.C. This advocacy arm of

1221-516: A few degrees releasing the pressure and is controlled by a mechanical governor, consisting of weights rotating at engine speed constrained by springs and a lever. The injectors are held open by the fuel pressure. On high-speed engines the plunger pumps are together in one unit. The length of fuel lines from the pump to each injector is normally the same for each cylinder in order to obtain the same pressure delay. Direct injected diesel engines usually use orifice-type fuel injectors. Electronic control of

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1332-407: A finite area, and the net output of work during a cycle is positive. The fuel efficiency of diesel engines is better than most other types of combustion engines, due to their high compression ratio, high air–fuel equivalence ratio (λ) , and the lack of intake air restrictions (i.e. throttle valves). Theoretically, the highest possible efficiency for a diesel engine is 75%. However, in practice

1443-452: A fuel consumption of 519 g·kW ·h . However, despite proving the concept, the engine caused problems, and Diesel could not achieve any substantial progress. Therefore, Krupp considered rescinding the contract they had made with Diesel. Diesel was forced to improve the design of his engine and rushed to construct a third prototype engine. Between 8 November and 20 December 1895, the second prototype had successfully covered over 111 hours on

1554-409: A full set of valves, two-stroke diesel engines have simple intake ports, and exhaust ports (or exhaust valves). When the piston approaches bottom dead centre, both the intake and the exhaust ports are "open", which means that there is atmospheric pressure inside the cylinder. Therefore, some sort of pump is required to blow the air into the cylinder and the combustion gasses into the exhaust. This process

1665-562: A heterogeneous air-fuel mixture. The torque a diesel engine produces is controlled by manipulating the air-fuel ratio (λ) ; instead of throttling the intake air, the diesel engine relies on altering the amount of fuel that is injected, and thus the air-fuel ratio is usually high. The diesel engine has the highest thermal efficiency (see engine efficiency ) of any practical internal or external combustion engine due to its very high expansion ratio and inherent lean burn, which enables heat dissipation by excess air. A small efficiency loss

1776-403: A low-pressure loop at the bottom of the diagram. At 1 it is assumed that the exhaust and induction strokes have been completed, and the cylinder is again filled with air. The piston-cylinder system absorbs energy between 1 and 2 – this is the work needed to compress the air in the cylinder, and is provided by mechanical kinetic energy stored in the flywheel of the engine. Work output is done by

1887-532: A more efficient replacement for stationary steam engines . Since the 1910s, they have been used in submarines and ships. Use in locomotives , buses, trucks, heavy equipment , agricultural equipment and electricity generation plants followed later. In the 1930s, they slowly began to be used in some automobiles . Since the 1970s energy crisis , demand for higher fuel efficiency has resulted in most major automakers, at some point, offering diesel-powered models, even in very small cars. According to Konrad Reif (2012),

1998-678: A notable exception being the EMD 567 , 645 , and 710 engines, which are all two-stroke. The power output of medium-speed diesel engines can be as high as 21,870 kW, with the effective efficiency being around 47-48% (1982). Most larger medium-speed engines are started with compressed air direct on pistons, using an air distributor, as opposed to a pneumatic starting motor acting on the flywheel, which tends to be used for smaller engines. Medium-speed engines intended for marine applications are usually used to power ( ro-ro ) ferries, passenger ships or small freight ships. Using medium-speed engines reduces

2109-565: A part of metal and metalloid alkoxides , of which many hundreds are known, could be classified as esters of the corresponding acids (e.g. aluminium triethoxide ( Al(OCH 2 CH 3 ) 3 ) could be classified as an ester of aluminic acid which is aluminium hydroxide , tetraethyl orthosilicate ( Si(OCH 2 CH 3 ) 4 ) could be classified as an ester of orthosilicic acid , and titanium ethoxide ( Ti(OCH 2 CH 3 ) 4 ) could be classified as an ester of orthotitanic acid ). Esters derived from carboxylic acids and alcohols contain

2220-526: A petroleum engine with glow-tube ignition in the early 1890s; he claimed against his own better judgement that his glow-tube ignition engine worked the same way Diesel's engine did. His claims were unfounded and he lost a patent lawsuit against Diesel. Other engines, such as the Akroyd engine and the Brayton engine , also use an operating cycle that is different from the diesel engine cycle. Friedrich Sass says that

2331-415: A poorer power-to-mass ratio than an equivalent petrol engine. The lower engine speeds (RPM) of typical diesel engines results in a lower power output. Also, the mass of a diesel engine is typically higher, since the higher operating pressure inside the combustion chamber increases the internal forces, which requires stronger (and therefore heavier) parts to withstand these forces. The distinctive noise of

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2442-408: A regular trunk-piston. Two-stroke engines have a limited rotational frequency and their charge exchange is more difficult, which means that they are usually bigger than four-stroke engines and used to directly power a ship's propeller. Four-stroke engines on ships are usually used to power an electric generator. An electric motor powers the propeller. Both types are usually very undersquare , meaning

2553-435: A simple mechanical injection system since exact injection timing is not as critical. Most modern automotive engines are DI which have the benefits of greater efficiency and easier starting; however, IDI engines can still be found in the many ATV and small diesel applications. Indirect injected diesel engines use pintle-type fuel injectors. Early diesel engines injected fuel with the assistance of compressed air, which atomised

2664-533: A single orifice injector. The pre-chamber has the disadvantage of lowering efficiency due to increased heat loss to the engine's cooling system, restricting the combustion burn, thus reducing the efficiency by 5–10%. IDI engines are also more difficult to start and usually require the use of glow plugs. IDI engines may be cheaper to build but generally require a higher compression ratio than the DI counterpart. IDI also makes it easier to produce smooth, quieter running engines with

2775-527: A single speed for long periods. Two-stroke engines use a combustion cycle which is completed in two strokes instead of four strokes. Filling the cylinder with air and compressing it takes place in one stroke, and the power and exhaust strokes are combined. The compression in a two-stroke diesel engine is similar to the compression that takes place in a four-stroke diesel engine: As the piston passes through bottom centre and starts upward, compression commences, culminating in fuel injection and ignition. Instead of

2886-426: A small chamber called a swirl chamber, precombustion chamber, pre chamber or ante-chamber, which is connected to the cylinder by a narrow air passage. Generally the goal of the pre chamber is to create increased turbulence for better air / fuel mixing. This system also allows for a smoother, quieter running engine, and because fuel mixing is assisted by turbulence, injector pressures can be lower. Most IDI systems use

2997-516: A source of radio frequency emissions (which can interfere with navigation and communication equipment), which is why only diesel-powered vehicles are allowed in some parts of the American National Radio Quiet Zone . To control the torque output at any given time (i.e. when the driver of a car adjusts the accelerator pedal ), a governor adjusts the amount of fuel injected into the engine. Mechanical governors have been used in

3108-400: A spark plug ( compression ignition rather than spark ignition ). In the diesel engine, only air is initially introduced into the combustion chamber. The air is then compressed with a compression ratio typically between 15:1 and 23:1. This high compression causes the temperature of the air to rise. At about the top of the compression stroke, fuel is injected directly into the compressed air in

3219-417: A swirl chamber or pre-chamber are called indirect injection (IDI) engines. Most direct injection diesel engines have a combustion cup in the top of the piston where the fuel is sprayed. Many different methods of injection can be used. Usually, an engine with helix-controlled mechanic direct injection has either an inline or a distributor injection pump. For each engine cylinder, the corresponding plunger in

3330-422: A two-stroke ship diesel engine has a single-stage turbocharger with a turbine that has an axial inflow and a radial outflow. In general, there are three types of scavenging possible: Crossflow scavenging is incomplete and limits the stroke, yet some manufacturers used it. Reverse flow scavenging is a very simple way of scavenging, and it was popular amongst manufacturers until the early 1980s. Uniflow scavenging

3441-684: Is γ-valerolactone . An uncommon class of esters are the orthoesters . One of them are the esters of orthocarboxylic acids. Those esters have the formula RC(OR′) 3 , where R stands for any group (organic or inorganic) and R ′ stands for organyl group. For example, triethyl orthoformate ( HC(OCH 2 CH 3 ) 3 ) is derived, in terms of its name (but not its synthesis) from esterification of orthoformic acid ( HC(OH) 3 ) with ethanol . Esters can also be derived from inorganic acids. Inorganic acids that exist as tautomers form two or more types of esters. Some inorganic acids that are unstable or elusive form stable esters. In principle,

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3552-529: Is a dibutylstannylene ester of lauric acid , and the Phillips catalyst CrO 2 (OSi(OCH 3 ) 3 ) 2 is a trimethoxysilyl ester of chromic acid ( H 2 CrO 4 ). The word ester was coined in 1848 by a German chemist Leopold Gmelin , probably as a contraction of the German Essigäther , " acetic ether ". The names of esters that are formed from an alcohol and an acid, are derived from

3663-461: Is a combustion engine that is more efficient than a diesel engine, but due to its mass and dimensions, is unsuitable for many vehicles, including watercraft and some aircraft . The world's largest diesel engines put in service are 14-cylinder, two-stroke marine diesel engines; they produce a peak power of almost 100 MW each. Diesel engines may be designed with either two-stroke or four-stroke combustion cycles . They were originally used as

3774-423: Is a simplified and idealised representation of the events involved in a diesel engine cycle, arranged to illustrate the similarity with a Carnot cycle . Starting at 1, the piston is at bottom dead centre and both valves are closed at the start of the compression stroke; the cylinder contains air at atmospheric pressure. Between 1 and 2 the air is compressed adiabatically – that is without heat transfer to or from

3885-510: Is a top priority for CFAA and a key element in the industry's growth. Regulation of fuel standards is a function primarily left to the states, but regulation of biodiesel is not uniform across all states. CFAA works with states on fuel quality enforcement measures. CFAA also catalogs information regarding their authority to regulate fuels; their status in adopting ASTM D6751 as the fuel specification for biodiesel; enforcement procedures; and assessment of capacity to analyze samples. CFAA administers

3996-458: Is also an equilibrium process – essentially the reverse of the Fischer esterification reaction. Because an alcohol (which acts as the leaving group) and water (which acts as the nucleophile) have similar p K a values, the forward and reverse reactions compete with each other. As in transesterification, using a large excess of reactant (water) or removing one of the products (the alcohol) can promote

4107-431: Is also avoided compared with non-direct-injection gasoline engines, as unburned fuel is not present during valve overlap, and therefore no fuel goes directly from the intake/injection to the exhaust. Low-speed diesel engines (as used in ships and other applications where overall engine weight is relatively unimportant) can reach effective efficiencies of up to 55%. The combined cycle gas turbine (Brayton and Rankine cycle)

4218-561: Is an internal combustion engine in which ignition of the fuel is caused by the elevated temperature of the air in the cylinder due to mechanical compression ; thus, the diesel engine is called a compression-ignition engine (CI engine). This contrasts with engines using spark plug -ignition of the air-fuel mixture, such as a petrol engine ( gasoline engine) or a gas engine (using a gaseous fuel like natural gas or liquefied petroleum gas ). Diesel engines work by compressing only air, or air combined with residual combustion gases from

4329-403: Is approximately 5 MW. Medium-speed engines are used in large electrical generators, railway diesel locomotives , ship propulsion and mechanical drive applications such as large compressors or pumps. Medium speed diesel engines operate on either diesel fuel or heavy fuel oil by direct injection in the same manner as low-speed engines. Usually, they are four-stroke engines with trunk pistons;

4440-429: Is called scavenging . The pressure required is approximately 10-30 kPa. Due to the lack of discrete exhaust and intake strokes, all two-stroke diesel engines use a scavenge blower or some form of compressor to charge the cylinders with air and assist in scavenging. Roots-type superchargers were used for ship engines until the mid-1950s, however since 1955 they have been widely replaced by turbochargers. Usually,

4551-648: Is considered too hazardous and expensive for large-scale applications. Carboxylic acids are esterified by treatment with epoxides , giving β-hydroxyesters: This reaction is employed in the production of vinyl ester resin from acrylic acid . Alcohols react with acyl chlorides and acid anhydrides to give esters: The reactions are irreversible simplifying work-up . Since acyl chlorides and acid anhydrides also react with water, anhydrous conditions are preferred. The analogous acylations of amines to give amides are less sensitive because amines are stronger nucleophiles and react more rapidly than does water. This method

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4662-404: Is done on the system to which the engine is connected. During this expansion phase the volume of the gas rises, and its temperature and pressure both fall. At 4 the exhaust valve opens, and the pressure falls abruptly to atmospheric (approximately). This is unresisted expansion and no useful work is done by it. Ideally the adiabatic expansion should continue, extending the line 3–4 to the right until

4773-605: Is employed only for laboratory-scale procedures, as it is expensive. Trimethyloxonium tetrafluoroborate can be used for esterification of carboxylic acids under conditions where acid-catalyzed reactions are infeasible: Although rarely employed for esterifications, carboxylate salts (often generated in situ ) react with electrophilic alkylating agents , such as alkyl halides , to give esters. Anion availability can inhibit this reaction, which correspondingly benefits from phase transfer catalysts or such highly polar aprotic solvents as DMF . An additional iodide salt may, via

4884-439: Is headquartered in Jefferson City, Missouri in a “recycled” building, which was renovated from the ground up with eco-conscious features. These include carpet made from recycled materials, high efficiency plumbing and appliances, skylights, automated office lights, non-toxic paint, and solar-powered parking lot lights. The building also has many green technological capabilities, such as worldwide videoconferencing , which reduces

4995-667: Is made up of 15 directors elected by voting members. Seven of the directors are elected by weighted votes . The remaining eight are elected by straight votes – two are feedstock producer organization voting delegates who are actively engaged in farming; two are voting delegates of producer or marketer members who are members of either the National Renderer’s Association or the Fats and Proteins Research Foundation (FPRF); and four are voting delegates of producer or marketer members and/or feedstock producer members who are not members of

5106-464: Is more complicated to make but allows the highest fuel efficiency; since the early 1980s, manufacturers such as MAN and Sulzer have switched to this system. It is standard for modern marine two-stroke diesel engines. So-called dual-fuel diesel engines or gas diesel engines burn two different types of fuel simultaneously , for instance, a gaseous fuel and diesel engine fuel. The diesel engine fuel auto-ignites due to compression ignition, and then ignites

5217-512: Is not usually reversible. Hydrazines and hydroxylamine can be used in place of amines. Esters can be converted to isocyanates through intermediate hydroxamic acids in the Lossen rearrangement . Sources of carbon nucleophiles, e.g., Grignard reagents and organolithium compounds, add readily to the carbonyl. Diesel engine The diesel engine , named after the German engineer Rudolf Diesel ,

5328-603: Is one illustrative example. The carbonylation of methanol yields methyl formate , which is the main commercial source of formic acid . The reaction is catalyzed by sodium methoxide : In hydroesterification , alkenes and alkynes insert into the O−H bond of carboxylic acids. Vinyl acetate is produced industrially by the addition of acetic acid to acetylene in the presence of zinc acetate catalysts: Vinyl acetate can also be produced by palladium -catalyzed reaction of ethylene, acetic acid , and oxygen : Silicotungstic acid

5439-499: Is used as an acyl-transfer catalyst . Another method for the dehydration of mixtures of alcohols and carboxylic acids is the Mitsunobu reaction : Carboxylic acids can be esterified using diazomethane : Using this diazomethane, mixtures of carboxylic acids can be converted to their methyl esters in near quantitative yields, e.g., for analysis by gas chromatography . The method is useful in specialized organic synthetic operations but

5550-495: Is used in the production of ethyl acetate from acetaldehyde . Esters are less reactive than acid halides and anhydrides. As with more reactive acyl derivatives, they can react with ammonia and primary and secondary amines to give amides, although this type of reaction is not often used, since acid halides give better yields. Esters can be converted to other esters in a process known as transesterification . Transesterification can be either acid- or base-catalyzed, and involves

5661-411: Is used to manufacture ethyl acetate by the alkylation of acetic acid by ethylene: The Tishchenko reaction involves disproportionation of an aldehyde in the presence of an anhydrous base to give an ester. Catalysts are aluminium alkoxides or sodium alkoxides. Benzaldehyde reacts with sodium benzyloxide (generated from sodium and benzyl alcohol ) to generate benzyl benzoate . The method

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5772-504: The EU average for diesel cars at the time accounted for half of newly registered cars. However, air pollution and overall emissions are more difficult to control in diesel engines compared to gasoline engines, and the use of diesel auto engines in the U.S. is now largely relegated to larger on-road and off-road vehicles . Though aviation has traditionally avoided using diesel engines, aircraft diesel engines have become increasingly available in

5883-500: The Finkelstein reaction , catalyze the reaction of a recalcitrant alkyl halide. Alternatively, salts of a coordinating metal, such as silver, may improve the reaction rate by easing halide elimination. Transesterification , which involves changing one ester into another one, is widely practiced: Like the hydrolysation, transesterification is catalysed by acids and bases. The reaction is widely used for degrading triglycerides , e.g. in

5994-694: The United Kingdom , and the United States for "Method of and Apparatus for Converting Heat into Work". In 1894 and 1895, he filed patents and addenda in various countries for his engine; the first patents were issued in Spain (No. 16,654), France (No. 243,531) and Belgium (No. 113,139) in December 1894, and in Germany (No. 86,633) in 1895 and the United States (No. 608,845) in 1898. Diesel

6105-573: The organyl parts of the carboxylic acid and the alcohol, respectively, and R can be a hydrogen in the case of esters of formic acid . For example, butyl acetate (systematically butyl ethanoate), derived from butanol and acetic acid (systematically ethanoic acid) would be written CH 3 CO 2 (CH 2 ) 3 CH 3 . Alternative presentations are common including BuOAc and CH 3 COO(CH 2 ) 3 CH 3 . Cyclic esters are called lactones , regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone

6216-400: The reaction product . Esters are common in organic chemistry and biological materials, and often have a pleasant characteristic, fruity odor. This leads to their extensive use in the fragrance and flavor industry. Ester bonds are also found in many polymers . The classic synthesis is the Fischer esterification , which involves treating a carboxylic acid with an alcohol in the presence of

6327-416: The 21st century. Since the late 1990s, for various reasons—including the diesel's inherent advantages over gasoline engines, but also for recent issues peculiar to aviation—development and production of diesel engines for aircraft has surged, with over 5,000 such engines delivered worldwide between 2002 and 2018, particularly for light airplanes and unmanned aerial vehicles . In 1878, Rudolf Diesel , who

6438-450: The Carnot cycle. Diesel was also introduced to a fire piston , a traditional fire starter using rapid adiabatic compression principles which Linde had acquired from Southeast Asia . After several years of working on his ideas, Diesel published them in 1893 in the essay Theory and Construction of a Rational Heat Motor . Diesel was heavily criticised for his essay, but only a few found

6549-680: The National Renderer’s Association or FPRF. CFAA was founded in 1992 by state soybean commodity groups. Originally known as the National Soy Diesel Development Board and later as the National Biodiesel Board, it was created by farmers who saw a real potential for biodiesel made from soybean oil . (Soybean oil is a byproduct of harvesting and processing soybeans for protein, for both human and animal consumption.) The commodity groups funded important biodiesel research and development programs focusing on soybean oil as

6660-562: The U.S. and Canada. Companies must pass a rigorous review and inspection of their quality control processes by an independent auditor. The National Biodiesel Accreditation Commission (NBAC) issues a “BQ-9000 producer” or “BQ-9000 Marketer” seal of approval for those who pass. CFAA membership adopted the following sustainability principles to guide the industry: CFAA developed an OEM education and outreach program to foster OEM understanding, technical research, acceptance and promotion of biodiesel. All diesel engine manufacturing companies warrant

6771-400: The amount of fuel injected into the engine. Due to the amount of air being constant (for a given RPM) while the amount of fuel varies, very high ("lean") air-fuel ratios are used in situations where minimal torque output is required. This differs from a petrol engine, where a throttle is used to also reduce the amount of intake air as part of regulating the engine's torque output. Controlling

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6882-417: The aroma of fruits, butter, cheese, vegetables like celery and other foods. Esters can be formed from oxoacids (e.g. esters of acetic acid , carbonic acid , sulfuric acid , phosphoric acid , nitric acid , xanthic acid ), but also from acids that do not contain oxygen (e.g. esters of thiocyanic acid and trithiocarbonic acid ). An example of an ester formation is the substitution reaction between

6993-427: The aroma of many fruits, including apples , durians , pears , bananas , pineapples , and strawberries . Several billion kilograms of polyesters are produced industrially annually, important products being polyethylene terephthalate , acrylate esters , and cellulose acetate . Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as

7104-470: The bore is smaller than the stroke. Low-speed diesel engines (as used in ships and other applications where overall engine weight is relatively unimportant) often have an effective efficiency of up to 55%. Like medium-speed engines, low-speed engines are started with compressed air, and they use heavy oil as their primary fuel. Four-stroke engines use the combustion cycle described earlier. Most smaller diesels, for vehicular use, for instance, typically use

7215-448: The combustion chamber, the droplets continue to vaporise from their surfaces and burn, getting smaller, until all the fuel in the droplets has been burnt. Combustion occurs at a substantially constant pressure during the initial part of the power stroke. The start of vaporisation causes a delay before ignition and the characteristic diesel knocking sound as the vapour reaches ignition temperature and causes an abrupt increase in pressure above

7326-418: The combustion chamber. This may be into a (typically toroidal ) void in the top of the piston or a pre-chamber depending upon the design of the engine. The fuel injector ensures that the fuel is broken down into small droplets, and that the fuel is distributed evenly. The heat of the compressed air vaporises fuel from the surface of the droplets. The vapour is then ignited by the heat from the compressed air in

7437-425: The compressed gas. Combustion and heating occur between 2 and 3. In this interval the pressure remains constant since the piston descends, and the volume increases; the temperature rises as a consequence of the energy of combustion. At 3 fuel injection and combustion are complete, and the cylinder contains gas at a higher temperature than at 2. Between 3 and 4 this hot gas expands, again approximately adiabatically. Work

7548-452: The compression ratio in a spark-ignition engine where fuel and air are mixed before entry to the cylinder is limited by the need to prevent pre-ignition , which would cause engine damage. Since only air is compressed in a diesel engine, and fuel is not introduced into the cylinder until shortly before top dead centre ( TDC ), premature detonation is not a problem and compression ratios are much higher. The pressure–volume diagram (pV) diagram

7659-473: The compression required for his cycle: By June 1893, Diesel had realised his original cycle would not work, and he adopted the constant pressure cycle. Diesel describes the cycle in his 1895 patent application. Notice that there is no longer a mention of compression temperatures exceeding the temperature of combustion. Now it is simply stated that the compression must be sufficient to trigger ignition. In 1892, Diesel received patents in Germany , Switzerland ,

7770-416: The concept of air-blast injection from George B. Brayton , albeit that Diesel substantially improved the system. On 17 February 1894, the redesigned engine ran for 88 revolutions – one minute; with this news, Maschinenfabrik Augsburg's stock rose by 30%, indicative of the tremendous anticipated demands for a more efficient engine. On 26 June 1895, the engine achieved an effective efficiency of 16.6% and had

7881-420: The corresponding amides . The p K a of the alpha-hydrogens on esters of carboxylic acids is around 25 (alpha-hydrogen is a hydrogen bound to the carbon adjacent to the carbonyl group (C=O) of carboxylate esters). Many carboxylic acid esters have the potential for conformational isomerism , but they tend to adopt an S - cis (or Z ) conformation rather than the S - trans (or E ) alternative, due to

7992-424: The cost of smaller ships and increases their transport capacity. In addition to that, a single ship can use two smaller engines instead of one big engine, which increases the ship's safety. Low-speed diesel engines are usually very large in size and mostly used to power ships . There are two different types of low-speed engines that are commonly used: Two-stroke engines with a crosshead, and four-stroke engines with

8103-460: The dehydration of mixtures of alcohols and carboxylic acids. One example is the Steglich esterification , which is a method of forming esters under mild conditions. The method is popular in peptide synthesis , where the substrates are sensitive to harsh conditions like high heat. DCC ( dicyclohexylcarbodiimide ) is used to activate the carboxylic acid to further reaction. 4-Dimethylaminopyridine (DMAP)

8214-598: The diesel engine is Diesel's "very own work" and that any "Diesel myth" is " falsification of history ". Diesel sought out firms and factories that would build his engine. With the help of Moritz Schröter and Max Gutermuth  [ de ] , he succeeded in convincing both Krupp in Essen and the Maschinenfabrik Augsburg . Contracts were signed in April 1893, and in early summer 1893, Diesel's first prototype engine

8325-417: The efficiency is much lower, with efficiencies of up to 43% for passenger car engines, up to 45% for large truck and bus engines, and up to 55% for large two-stroke marine engines. The average efficiency over a motor vehicle driving cycle is lower than the diesel engine's peak efficiency (for example, a 37% average efficiency for an engine with a peak efficiency of 44%). That is because the fuel efficiency of

8436-1118: The engines they make for “materials and workmanship.” While most companies recommend a particular type of fuel in the owner's manual, engine manufacturers do not warrant fuel, including regular diesel . Many companies have stated formally that the use of blends up to B20 (20 percent biodiesel, 80 percent diesel) will not void their parts and workmanship warranties. All U.S. OEMs approve of at least B5, and more than 54 percent support B20 or higher blends in at least some of their models. Driven by new engine emissions requirements , which take effect on January 1, 2010, many engine manufacturers have completely redesigned their diesel engines for compliance. Each February, CFAA holds its annual Clean Fuels Conference. The event provides educational tracks for all biodiesel stakeholders – state, national, and international feedstock and feedstock processor organizations, biodiesel suppliers, fuel marketers and distributors, and technology providers – as well as networking opportunities, industry updates, and access to government leaders. The conference has been going green for many years with

8547-408: The environment – by the rising piston. (This is only approximately true since there will be some heat exchange with the cylinder walls .) During this compression, the volume is reduced, the pressure and temperature both rise. At or slightly before 2 (TDC) fuel is injected and burns in the compressed hot air. Chemical energy is released and this constitutes an injection of thermal energy (heat) into

8658-555: The ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well (e.g. amides ), but not according to the IUPAC . Glycerides are fatty acid esters of glycerol ; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils . Lactones are cyclic carboxylic esters; naturally occurring lactones are mainly 5- and 6-membered ring lactones. Lactones contribute to

8769-406: The exhaust (known as exhaust gas recirculation , "EGR"). Air is inducted into the chamber during the intake stroke, and compressed during the compression stroke. This increases air temperature inside the cylinder so that atomised diesel fuel injected into the combustion chamber ignites. With the fuel being injected into the air just before combustion, the dispersion of fuel is uneven; this is called

8880-408: The first carbon atom of the organyl group replacing acidic hydrogen, is replaced by another atom from the group 14 elements ( Si , Ge , Sn , Pb ); for example, according to them, trimethylstannyl acetate (or trimethyltin acetate) CH 3 COOSn(CH 3 ) 3 is a trimethylstannyl ester of acetic acid , and dibutyltin dilaurate (CH 3 (CH 2 ) 10 COO) 2 Sn((CH 2 ) 3 CH 3 ) 2

8991-495: The forward reaction. Basic hydrolysis of esters, known as saponification , is not an equilibrium process; a full equivalent of base is consumed in the reaction, which produces one equivalent of alcohol and one equivalent of a carboxylate salt. The saponification of esters of fatty acids is an industrially important process, used in the production of soap. Esterification is a reversible reaction. Esters undergo hydrolysis under acidic and basic conditions. Under acidic conditions,

9102-463: The four-stroke cycle. This is due to several factors, such as the two-stroke design's narrow powerband which is not particularly suitable for automotive use and the necessity for complicated and expensive built-in lubrication systems and scavenging measures. The cost effectiveness (and proportion of added weight) of these technologies has less of an impact on larger, more expensive engines, while engines intended for shipping or stationary use can be run at

9213-612: The fuel and forced it into the engine through a nozzle (a similar principle to an aerosol spray). The nozzle opening was closed by a pin valve actuated by the camshaft . Although the engine was also required to drive an air compressor used for air-blast injection, the efficiency was nonetheless better than other combustion engines of the time. However the system was heavy and it was slow to react to changing torque demands, making it unsuitable for road vehicles. A unit injector system, also known as "Pumpe-Düse" ( pump-nozzle in German) combines

9324-697: The fuel injection transformed the direct injection engine by allowing much greater control over the combustion. Common rail (CR) direct injection systems do not have the fuel metering, pressure-raising and delivery functions in a single unit, as in the case of a Bosch distributor-type pump, for example. A high-pressure pump supplies the CR. The requirements of each cylinder injector are supplied from this common high pressure reservoir of fuel. An Electronic Diesel Control (EDC) controls both rail pressure and injections depending on engine operating conditions. The injectors of older CR systems have solenoid -driven plungers for lifting

9435-405: The fuel pump measures out the correct amount of fuel and determines the timing of each injection. These engines use injectors that are very precise spring-loaded valves that open and close at a specific fuel pressure. Separate high-pressure fuel lines connect the fuel pump with each cylinder. Fuel volume for each single combustion is controlled by a slanted groove in the plunger which rotates only

9546-461: The gaseous fuel. Such engines do not require any type of spark ignition and operate similar to regular diesel engines. The fuel is injected at high pressure into either the combustion chamber , "swirl chamber" or "pre-chamber," unlike petrol engines where the fuel is often added in the inlet manifold or carburetor . Engines where the fuel is injected into the main combustion chamber are called direct injection (DI) engines, while those which use

9657-581: The help of zero waste event producers The Spitfire Agency. The Clean Fuels Foundation (CFF), formerly known as the National Biodiesel Foundation, was organized in 1994 to support and promote outreach, education, science, and demonstration activities for the advancement of biodiesel and its co-products to improve national security , air quality , and the environment . Project funding is provided through government grants, charitable organizations, and corporate and individual donations. The CFAA

9768-419: The injection needle, whilst newer CR injectors use plungers driven by piezoelectric actuators that have less moving mass and therefore allow even more injections in a very short period of time. Early common rail system were controlled by mechanical means. The injection pressure of modern CR systems ranges from 140 MPa to 270 MPa. An indirect diesel injection system (IDI) engine delivers fuel into

9879-553: The injector and fuel pump into a single component, which is positioned above each cylinder. This eliminates the high-pressure fuel lines and achieves a more consistent injection. Under full load, the injection pressure can reach up to 220 MPa. Unit injectors are operated by a cam and the quantity of fuel injected is controlled either mechanically (by a rack or lever) or electronically. Due to increased performance requirements, unit injectors have been largely replaced by common rail injection systems. The average diesel engine has

9990-476: The mistake that he made; his rational heat motor was supposed to utilise a constant temperature cycle (with isothermal compression) that would require a much higher level of compression than that needed for compression ignition. Diesel's idea was to compress the air so tightly that the temperature of the air would exceed that of combustion. However, such an engine could never perform any usable work. In his 1892 US patent (granted in 1895) #542846, Diesel describes

10101-399: The need for travel. Ester In chemistry , an ester is a compound derived from an acid (organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group ( −OH ) of that acid is replaced by an organyl group (R ′ ). These compounds contain a distinctive functional group . Analogues derived from oxygen replaced by other chalcogens belong to

10212-424: The organization engages in critical federal policy efforts on behalf of the industry, such as the biodiesel tax incentive and Renewable Fuels Standard , which requires modest amounts of biomass-based diesel to be blended into the nation’s diesel supply. CFAA’s regulatory team monitors and analyzes both the regulatory and legislative landscapes of the biodiesel industry – identifying barriers and opportunities to expand

10323-448: The other hand, more frequently named using the systematic IUPAC name, based on the name for the acid followed by the suffix -oate . For example, the ester hexyl octanoate, also known under the trivial name hexyl caprylate , has the formula CH 3 (CH 2 ) 6 CO 2 (CH 2 ) 5 CH 3 . The chemical formulas of organic esters formed from carboxylic acids and alcohols usually take the form RCO 2 R' or RCOOR', where R and R' are

10434-464: The parent alcohol and the parent acid, where the latter may be organic or inorganic. Esters derived from the simplest carboxylic acids are commonly named according to the more traditional, so-called " trivial names " e.g. as formate, acetate, propionate, and butyrate, as opposed to the IUPAC nomenclature methanoate, ethanoate, propanoate, and butanoate. Esters derived from more complex carboxylic acids are, on

10545-534: The past, however electronic governors are more common on modern engines. Mechanical governors are usually driven by the engine's accessory belt or a gear-drive system and use a combination of springs and weights to control fuel delivery relative to both load and speed. Electronically governed engines use an electronic control unit (ECU) or electronic control module (ECM) to control the fuel delivery. The ECM/ECU uses various sensors (such as engine speed signal, intake manifold pressure and fuel temperature) to determine

10656-477: The piston (not shown on the P-V indicator diagram). When combustion is complete the combustion gases expand as the piston descends further; the high pressure in the cylinder drives the piston downward, supplying power to the crankshaft. As well as the high level of compression allowing combustion to take place without a separate ignition system, a high compression ratio greatly increases the engine's efficiency. Increasing

10767-403: The piston-cylinder combination between 2 and 4. The difference between these two increments of work is the indicated work output per cycle, and is represented by the area enclosed by the pV loop. The adiabatic expansion is in a higher pressure range than that of the compression because the gas in the cylinder is hotter during expansion than during compression. It is for this reason that the loop has

10878-417: The pollutants can be removed from the exhaust gas using exhaust gas treatment technology. Road vehicle diesel engines have no sulfur dioxide emissions, because motor vehicle diesel fuel has been sulfur-free since 2003. Helmut Tschöke argues that particulate matter emitted from motor vehicles has negative impacts on human health. The particulate matter in diesel exhaust emissions is sometimes classified as

10989-408: The pressure falls to that of the surrounding air, but the loss of efficiency caused by this unresisted expansion is justified by the practical difficulties involved in recovering it (the engine would have to be much larger). After the opening of the exhaust valve, the exhaust stroke follows, but this (and the following induction stroke) are not shown on the diagram. If shown, they would be represented by

11100-510: The primary feedstock source for biodiesel. Feedstock is whatever the main ingredient of a biodiesel is. While the majority of today's biodiesel is still made from soybean oil, over the years, new feedstocks have emerged. Today, feedstocks range from camelina , cottonseed , and canola oil to restaurant trap grease , recycled cooking oil and beef tallow . Additional research may someday develop algae and other high-oil sources into commercially viable options. Consequently, CFAA has evolved into

11211-467: The production of fatty acid esters and alcohols. Poly(ethylene terephthalate) is produced by the transesterification of dimethyl terephthalate and ethylene glycol: A subset of transesterification is the alcoholysis of diketene . This reaction affords 2-ketoesters. Alkenes undergo carboalkoxylation in the presence of metal carbonyl catalysts. Esters of propanoic acid are produced commercially by this method: A preparation of methyl propionate

11322-440: The range 1730–1750 cm assigned to ν C=O . This peak changes depending on the functional groups attached to the carbonyl. For example, a benzene ring or double bond in conjunction with the carbonyl will bring the wavenumber down about 30 cm . Esters are widespread in nature and are widely used in industry. In nature, fats are, in general, triesters derived from glycerol and fatty acids . Esters are responsible for

11433-406: The reaction is the reverse reaction of the Fischer esterification . Under basic conditions, hydroxide acts as a nucleophile, while an alkoxide is the leaving group. This reaction, saponification , is the basis of soap making. The alkoxide group may also be displaced by stronger nucleophiles such as ammonia or primary or secondary amines to give amides (ammonolysis reaction): This reaction

11544-420: The reaction of an ester with an alcohol. Unfortunately, because the leaving group is also an alcohol, the forward and reverse reactions will often occur at similar rates. Using a large excess of the reactant alcohol or removing the leaving group alcohol (e.g. via distillation ) will drive the forward reaction towards completion, in accordance with Le Chatelier's principle . Acid-catalyzed hydrolysis of esters

11655-539: The test bench. In the January 1896 report, this was considered a success. In February 1896, Diesel considered supercharging the third prototype. Imanuel Lauster , who was ordered to draw the third prototype " Motor 250/400 ", had finished the drawings by 30 April 1896. During summer that year the engine was built, it was completed on 6 October 1896. Tests were conducted until early 1897. First public tests began on 1 February 1897. Moritz Schröter 's test on 17 February 1897

11766-890: The timing of the start of injection of fuel into the cylinder is similar to controlling the ignition timing in a petrol engine. It is therefore a key factor in controlling the power output, fuel consumption and exhaust emissions. There are several different ways of categorising diesel engines, as outlined in the following sections. Günter Mau categorises diesel engines by their rotational speeds into three groups: High-speed engines are used to power trucks (lorries), buses , tractors , cars , yachts , compressors , pumps and small electrical generators . As of 2018, most high-speed engines have direct injection . Many modern engines, particularly in on-highway applications, have common rail direct injection . On bigger ships, high-speed diesel engines are often used for powering electric generators. The highest power output of high-speed diesel engines

11877-422: The use of biodiesel. The state regulatory team tracks an average of 300 pieces of legislation nationwide. The team provides access to bills through a members-only website and updates members with regular communications summarizing current events, specific legislation, passed legislation, new incentives, and regulatory developments. Ensuring consumers have a high level of confidence in the biodiesel they purchase

11988-524: Was a student at the "Polytechnikum" in Munich , attended the lectures of Carl von Linde . Linde explained that steam engines are capable of converting just 6–10% of the heat energy into work, but that the Carnot cycle allows conversion of much more of the heat energy into work by means of isothermal change in condition. According to Diesel, this ignited the idea of creating a highly efficient engine that could work on

12099-488: Was attacked and criticised over several years. Critics claimed that Diesel never invented a new motor and that the invention of the diesel engine is fraud. Otto Köhler and Emil Capitaine  [ de ] were two of the most prominent critics of Diesel's time. Köhler had published an essay in 1887, in which he describes an engine similar to the engine Diesel describes in his 1893 essay. Köhler figured that such an engine could not perform any work. Emil Capitaine had built

12210-472: Was built in Augsburg . On 10 August 1893, the first ignition took place, the fuel used was petrol. In winter 1893/1894, Diesel redesigned the existing engine, and by 18 January 1894, his mechanics had converted it into the second prototype. During January that year, an air-blast injection system was added to the engine's cylinder head and tested. Friedrich Sass argues that, it can be presumed that Diesel copied

12321-424: Was the main test of Diesel's engine. The engine was rated 13.1 kW with a specific fuel consumption of 324 g·kW ·h , resulting in an effective efficiency of 26.2%. By 1898, Diesel had become a millionaire. The characteristics of a diesel engine are The diesel internal combustion engine differs from the gasoline powered Otto cycle by using highly compressed hot air to ignite the fuel rather than using

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