Hexamethylene Diisocyanate
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Hexamethylene Diisocyanate
Hexamethylene diisocyanate (HDI) is the organic compound with the formula (CH2)6(NCO)2. It is classified as an diisocyanate. It is a colorless liquid. It has sometimes been called HMDI but this not usually done to avoid confusion with Hydrogenated MDI. Synthesis Compared to other commercial diisocyanates, HDI is produced in relatively small quantities, accounting for (with isophorone diisocyanate) only 3.4% of the global diisocyanate market in the year 2000. It is produced by phosgenation of hexamethylene diamine. Applications Aliphatic diisocyanates are used in specialty applications, such as enamel coatings which are resistant to abrasion and degradation by ultraviolet light. These properties are particularly desirable in, for instance, the exterior paint applied to aircraft and vessels. HDI is also sold oligomerized as the trimer or biuret which are used in automotive refinish coatings. Although more viscous in these forms, it reduces the volatility and toxicity. At least 3 c ...
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Poise (unit)
The poise (symbol P; ) is the unit of dynamic viscosity (absolute viscosity) in the centimetre–gram–second system of units (CGS). It is named after Jean Léonard Marie Poiseuille (see Hagen–Poiseuille equation). The centipoise (1 cP = 0.01 P) is more commonly used than the poise itself. Dynamic viscosity has dimension \mathrm. 1~\text = 0.1~\text^ \text \text^ = 1~\text^ \text \text^ = 1~\text \text \text^. The analogous unit in the International System of Units is the pascal-second (Pa⋅s): 1~\text \text = 1~\text \text \text^ = 1~\text^ \text \text^ = 10~\text. The poise is often used with the metric prefix ''centi-'' because the viscosity of water at 20 °C ( standard conditions for temperature and pressure) is almost exactly 1 centipoise. A centipoise is one hundredth of a poise, or one millipascal-second (mPa⋅s) in SI units (1 cP = 10−3 Pa⋅s = 1 mPa⋅s). The CGS symbol for the centipoise is cP. The abbreviations cps, ...
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Isocyanate
In organic chemistry, isocyanate is the functional group with the formula . Organic compounds that contain an isocyanate group are referred to as isocyanates. An organic compound with two isocyanate groups is known as a diisocyanate. Diisocyanates are manufactured for the production of polyurethanes, a class of polymers. Isocyanates should not be confused with cyanate esters and isocyanides, very different families of compounds. The cyanate (cyanate ester) functional group () is arranged differently from the isocyanate group (). Isocyanides have the connectivity , lacking the oxygen of the cyanate groups. Structure and bonding In terms of bonding, isocyanates are closely related to carbon dioxide (CO2) and carbodiimides (C(NR)2). The C−N=C=O unit that defines isocyanates is planar, and the N=C=O linkage is nearly linear. In phenyl isocyanate, the C=N and C=O distances are respectively 1.195 and 1.173  Å. The C-N=C angle is 134.9° and the N=C=O angle is 173.1°. ...
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Isophorone Diisocyanate
Isophorone diisocyanate (IPDI) is an organic compound in the class known as isocyanates. More specifically, it is an aliphatic diisocyanate. It is produced in relatively small quantities, accounting for (with hexamethylene diisocyanate) only 3.4% of the global diisocyanate market in the year 2000.{{cite book , first=David , last=Randall , author2=Lee, Steve , title=The Polyurethanes Book , publisher=Wiley , location=New York , year=2002 , isbn=0-470-85041-8 Aliphatic diisocyanates are used, not in the production of polyurethane foam, but in special applications, such as enamel coatings which are resistant to abrasion and degradation from ultraviolet light. These properties are particularly desirable in, for instance, the exterior paint applied to aircraft. Synthesis IPDI is obtained by phosgenation of isophorone diamine: Chemistry IPDI exists in two stereoisomers, cis and trans. Their reactivities are similar. Each stereoisomer is an unsymmetrical molecule, and thus has ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Living t ...
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Hydrogenated MDI
Hydrogenated MDI (H12MDI or 4,4′-diisocyanato dicyclohexylmethane) is an organic compound in the class known as isocyanates. More specifically, it is an aliphatic diisocyanate. It is a water white liquid at room temperature and is manufactured in relatively small quantities. It is also known as 4,4'-methylenedi(cyclohexyl isocyanate) or methylene bis(4-cyclohexylisocyanate) and has the formula CH2 C6H10)NCOsub>2. Manufacture The product is manufactured by hydrogenation of methylene diphenyl diisocyanate. It may also be manufactured by phosgenation of 4,4-Diaminodicyclohexylmethane. Uses Aliphatic diisocyanates are not used in the production of polyurethane foam as the cost is too high and foam is very much a commodity. It is used in special applications for polyurethane, such as enamel coatings which are resistant to abrasion and degradation from ultraviolet light. There are also multiple patents where prepolymers based on it are used in golf ball production. It is available com ...
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Isophorone Diisocyanate
Isophorone diisocyanate (IPDI) is an organic compound in the class known as isocyanates. More specifically, it is an aliphatic diisocyanate. It is produced in relatively small quantities, accounting for (with hexamethylene diisocyanate) only 3.4% of the global diisocyanate market in the year 2000.{{cite book , first=David , last=Randall , author2=Lee, Steve , title=The Polyurethanes Book , publisher=Wiley , location=New York , year=2002 , isbn=0-470-85041-8 Aliphatic diisocyanates are used, not in the production of polyurethane foam, but in special applications, such as enamel coatings which are resistant to abrasion and degradation from ultraviolet light. These properties are particularly desirable in, for instance, the exterior paint applied to aircraft. Synthesis IPDI is obtained by phosgenation of isophorone diamine: Chemistry IPDI exists in two stereoisomers, cis and trans. Their reactivities are similar. Each stereoisomer is an unsymmetrical molecule, and thus has ...
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Phosgenation
Phosgene is the organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. Phosgene is a valued and important industrial building block, especially for the production of precursors of polyurethanes and polycarbonate plastics. Phosgene is extremely poisonous and was used as a chemical weapon during World War I, where it was responsible for 85,000 deaths. It was a highly potent pulmonary irritant and quickly filled enemy trenches due to it being a heavy gas. It is classified as a Schedule 3 substance under the Chemical Weapons Convention. In addition to its industrial production, small amounts occur from the breakdown and the combustion of organochlorine compounds, such as chloroform. Structure and basic properties Phosgene is a planar molecule as predicted by VSEPR theory. The C=O distance is 1.18  Å, the C−Cl distance is 1.74 Å and the Cl−C−Cl angle is 111 ...
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Hexamethylene Diamine
Hexamethylenediamine is the organic compound with the formula H2N(CH2)6NH2. The molecule is a diamine, consisting of a hexamethylene hydrocarbon chain terminated with amine functional groups. The colorless solid (yellowish for some commercial samples) has a strong amine odor. About 1 billion kilograms are produced annually.Robert A. Smiley "Hexamethylenediamine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. Synthesis Hexamethylenediamine was first reported by Theodor Curtius. It is produced by the hydrogenation of adiponitrile: :NC(CH2)4CN + 4 H2 → H2N(CH2)6NH2 The hydrogenation is conducted on molten adiponitrile diluted with ammonia, typical catalysts being based on cobalt and iron. The yield is good, but commercially significant side products are generated by virtue of reactivity of partially hydrogenated intermediates. These other products include 1,2-diaminocyclohexane, hexamethyleneimine, and the triamine bis(hexamethylenetriam ...
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Oxazolidine
An oxazolidine is a five-membered ring compound consisting of three carbon atoms, a nitrogen atom and an oxygen atom. The O atom and NH group are the 1 and 3 positions, respectively. In oxazolidine derivatives, there is always a carbon atom between the O and N atoms (or it would be an ''isoxazolidine''). All of the carbon atoms in oxazolidines are reduced (compare to oxazole and oxazoline). Some of their derivatives, the oxazolidinediones, are used as anticonvulsants. Oxazolidines were first synthesized over 100 years ago. Monooxazolidines Oxazolidines that are the precursor to bisoxazolidines are in effect mono-oxazolidines. They are also used as moisture scavengers in polyurethane and other systems. Dioxooxazolidines Oxazolidines where the carbon centers at the 1 and 3 positions are carbonyls are called dioxooxazolidines. Some of these are commercial fungicides including chlozolinate, vinclozolin, and famoxadone. Bisoxazolidines Bisoxazolidines are chemical compounds tha ...
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Methylene Diphenyl Diisocyanate
Methylene diphenyl diisocyanate (MDI) is an aromatic diisocyanate. Three isomers are common, varying by the positions of the isocyanate groups around the rings: 2,2′-MDI, 2,4′-MDI, and 4,4′-MDI. The 4,4′ isomer is most widely used, and is also known as 4,4′-diphenylmethane diisocyanate. This isomer is also known as Pure MDI. MDI reacts with polyols in the manufacture of polyurethane. It is the most produced diisocyanate, accounting for 61.3% of the global market in the year 2000. Production Total world production of MDI and polymeric MDI is over 7.5 million tonnes per year (in 2017). As of 2019, the largest producer was Wanhua Chemical Group. Other major producers are Covestro, BASF, Dow, Huntsman, Tosoh, Kumho Mitsui Chemicals. All major producers of MDI are members of the International Isocyanate Institute, whose aim is the promotion of the safe handling of MDI and TDI in the workplace, community and environment. The first step of the production of MDI is the rea ...
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Toluene Diisocyanate
Toluene diisocyanate (TDI) is an organic compound with the formula CH3C6H3(NCO)2. Two of the six possible isomers are commercially important: 2,4-TDI (CAS: 584-84-9) and 2,6-TDI (CAS: 91-08-7). 2,4-TDI is produced in the pure state, but TDI is often marketed as 80/20 and 65/35 mixtures of the 2,4 and 2,6 isomers respectively. It is produced on a large scale, accounting for 34.1% of the global isocyanate market in 2000, second only to MDI. Approximately 1.4 billion kilograms were produced in 2000. All isomers of TDI are colorless, although commercial samples can appear yellow. Synthesis 2,4-TDI is prepared in three steps from toluene via dinitrotoluene and 2,4-diaminotoluene (TDA). Finally, the TDA is subjected to ''phosgenation'', i.e., treatment with phosgene to form TDI. This final step produces HCl as a byproduct and is a major source of industrial hydrochloric acid. : Distillation of the raw TDI mixture produces an 80:20 mixture of 2,4-TDI and 2,6-TDI, known as TDI (80/20) ...
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