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Topic: Cyanohydrin reaction

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	Reference.com/Encyclopedia/Cyanohydrin reaction
		A Cyanohydrin reaction is an organic reaction by an aldehyde or ketone with a cyanide anion or a nitrile to form a cyanohydrin.
		Cyanohydrin reaction of formaldehyde to hydroxyacetonitrile or glycolonitrile with sodium cyanide in Organic Syntheses Coll.
		Cyanohydrin reaction of formaldehyde with potassium cyanide Organic Syntheses Coll.
	www.reference.com /browse/wiki/Cyanohydrin_reaction (325 words)

	Cyanohydrin - Wikipedia, the free encyclopedia
		A cyanohydrin (or hydroxynitrile) is any of several compounds that contain both the cyanide and hydroxide groups.
		Geminal cyanohydrins can be formed by reacting a ketone with hydrogen cyanide (HCN) and a small amount of sodium cyanide (NaCN) as catalyst in the cyanohydrin reaction.
		This reaction is a form of nucleophilic addition, in which the nucleophilic CN ion attacks the electron deficient carbon in the ketone.
	en.wikipedia.org /wiki/Cyanohydrin (113 words)

	Enantiomeric enrichment of cyanohydrins - Patent 5241087
		Cyanohydrins of the structure ##STR1## where R.sub.1 and R.sub.2 are selected from hydrogen and substituted or unsubstituted alkyl or aryl, are important starting materials and intermediates in the preparation of a large number of biologically active compounds.
		An alternative to using an enantioselective hydrocyanation catalyst to prepare chiral cyanohydrins is enantioselective dehydrocyanation, that is, the use of an enantioselective catalyst to effect the enrichment of a mixture of chiral cyanohydrins by preferentially converting one enantiomer in the mixture into hydrogen cyanide and the corresponding aldehyde or ketone.
		Hydrogen cyanide removal reactions are preferably carried out under acidic or substantially neutral conditions to minimize the base-catalyzed dehydrocyanation of the cyanohydrin undergoing enrichment, which would otherwise reduce the yield of chiral cyanohydrin in the enantiomeric enrichment process and could result in racemization of the cyanohydrin undergoing enrichment.
	www.freepatentsonline.com /5241087.html (7200 words)

	Cyahohydrin Formation
		In some cases, ethynylcerium reagents showed incresed efficiency in their reaction with anthracycline precursors compared to their magnesium analogues; in other examples, the reagent is either unreactive or is still to basic.
		The cyanohydrin is considered to have the structure (2) on the basis of it's spectroscopic properties.
		The cyanohydrin was oxidised by the action of lead(IV) acetate in acetic acid to afford the anthracycline (3) in 23% yield after crystallisation.
	www.jonathanpmiller.com /cyanohydrin (635 words)

	Nitrile - Wikipedia, the free encyclopedia
		reaction of metal cyanides with aldehydes in the cyanohydrin reaction
		In organic reduction the nitrile is reduced by reacting it with hydrogen with a nickel catalyst; an amine is formed in this reaction.
		A nitrile is an electrophile in a nucleophilic addition reaction with an organozinc compound in the Blaise reaction.
	en.wikipedia.org /wiki/Nitrile (467 words)

	Process for producing .alpha.-hydroxyisobutyramide - Patent 5463123
		There is disclosed a process for producing.alpha.-hydroxyisobutyramide by hydration reaction of acetone cyanohydrin in the presence of a catalyst consisting essentially of manganese dioxide which process comprises pretreating the catalyst with a reducing agent.
		As a result, it has been found by the present inventors that the white crystal which was deposited in the beginning of the synthetic reaction of acetone cyanohydrin with water into.alpha.-hydroxyisobutyramide in the presence of the modified manganese catalyst was sparingly soluble in water and organic solvents and that it was an oxamide.
		The hydration reaction temperature of acetone cyanohydrin according to the present invention is in the range of 30.degree.
	www.freepatentsonline.com /5463123.html (1988 words)

	Mechanistic aspects of cyanogenesis from active-site mutant Ser80Ala of hydroxynitrile lyase from Manihot esculenta in ... (Site not responding. Last check: 2007-11-07)
		for acetone cyanohydrin of molecule A and 52 Å
		for the substrate acetone cyanohydrin was 3 units/mg and 67
		to the spontaneous decomposition of acetone cyanohydrin, the
	www.proteinscience.org /cgi/content/full/10/5/1015?ck=nck (3935 words)

	Reference.com/Encyclopedia/Cyanohydrin
		Cyanohydrins can be formed by the cyanohydrin reaction, which involves treating a ketone or an aldehyde with hydrogen cyanide (HCN) in the presence of a small amount of sodium cyanide (NaCN) as a catalyst:
		Thus, acetone cyanohydrin can be used for the preparation other cyanohydrins, for of HCN to Michael acceptors, and for the formylation of arenes.
		It is the simplest cyanohydrin, being derived from formaldehyde.
	www.reference.com /browse/wiki/Cyanohydrin (283 words)

	Method for making intermediates useful in the synthesis of retroviral protease inhibitors - Patent 5648511
		The reaction may be carried out under an inert atmosphere such as nitrogen or argon, or normal or dry air, under atmospheric pressure or in a sealed reaction vessel under positive pressure.
		In additional to the stereospecificity of the cyanohydrin reaction, this process has the added advantage of being easier and less expensive because the temperature of the reactions need not be less than -5.degree.
		The reaction mixture was cooled with ice water and quenced with 1.6 L of cold water (10.degree.-15.degree.
	www.freepatentsonline.com /5648511.html (12407 words)

	Cyanohydrin reaction at AllExperts
		Reaction of benzoquinone with trimethylsilylcyanide, catalyst KCN is introduced as a 1:1 complex with the Crown ether 18-crown-6
		* Cyanohydrin reaction of formaldehyde to hydroxyacetonitrile or glycolonitrile with sodium cyanide in Organic Syntheses Coll.
		* Cyanohydrin reaction of formaldehyde with potassium cyanide Organic Syntheses Coll.
	en.allexperts.com /e/c/cy/cyanohydrin_reaction.htm (401 words)

	Carboxylic acids and methods of preparing the same - Patent 4996356
		In the said reaction, polymerization inhibitors such as hydroquinone and hydroquinone monomethyl ether may be employed in a small amount to avoid polymerization of acrylonitrile or acrylic acid derivatives.
		If necessary, the reaction of the 1,2-epoxyalkane [general formula (3); 1,2-epoxydodecane, 1,2-epoxytetradecane of the like]with ethylene cyanohydrin may be carried out in the presence of an alkaline catalyst, such as sodium hydroxide, potassium hydroxide or triethyamine, or an acid catalyst such as sulfuric acid or trifluoroboron.
		The reaction of the 1,2-epoxyalkane [general formula (3)]with the alkyl glycolate represented by the general formula (4) (methyl glycolate, ethyl glycolate, or the like) may be carried out, if necessary, in the presence of an alkaline catalyst such as sodium hydroxide, potassium hydroxide or triethyamine, or an acid catalyst such as sulfuric acid or trifluoroboron.
	www.freepatentsonline.com /4996356.html (4490 words)

	Process for preparing lactamide
		Reaction: Manganese dioxide obtained above was crushed so as to be a size of 10 to 20 mesh, and 3.5 g of the thus ground manganese dioxide was filled into a glass reaction tube having an inner diameter of 10 mm equipped with a jacket.
		Reaction: Reaction was carried out in the presence of 3.5 g of the manganese dioxide catalyst obtained above in the same manner as in Comparative Example 1 except that the flow rate of a material solution was 7 g/hr and a circulation ratio was 10.
		Reaction: The hydration reaction of lactonitrile was carried out in the presence of 3.5 g of the manganese dioxide catalyst obtained above in the same manner as in Comparative Example 2 except that triethylamine was used as an additive in an amount of 0.86% by weight based on the weight of a material solution.
	www.devileye.net /catalog/froth_activator/process_preparing_lactamide.html (3057 words)

	Process for obtaining 2-hydroxy-4-methylthiobutyric acid (MHA) - United States Patent 6,140,536
		A method for the isolation of 2-hydroxy-4-methylthiobutyric acid (MHA), wherein MHA is isolated from a reaction mixture obtained by addition of hydrogen cyanide (HCN) to methylmercaptopropionaldehyde (MMP) and hydrolysis by sulphuric acid of the methylmercaptopropionaldehyde cyanohydrin (MMP-CH) thus obtained.
		On the one hand, the hydrolysis reaction should proceed as far as possible to completion, to which end a relatively lower amide concentration in the water present during the MHA amide saponification is appropriate.
		The MHA hydrolysate solution used for the extraction was prepared from 114.7 kg (874 mol) of MMP cyanohydrin and 131.9 kg (874 mol, 1.00 mol equiv.) of 65% H.sub.2 SO.sub.4 in a pressure-resistant 400 l agitated tank at a temperature of 50.degree.
	xrint.com /patents/us/6140536 (12320 words)

	U.S. Patent: 5696286 - Process for the preparation of aromatic-substituted aliphatic carboxylic acids - December 9, 1997
		In another embodiment of the present invention, the reaction mixture formed from the catalytic hydrogenation step is again treated with a dehydrating agent in the manner disclosed herein as the first step of the process of the present invention, thus forming a second reaction solution.
		Again, the process is halted when the amount of unsaturated nitrile produced from the dehydration of the cyanohydrin does not exceed 10% of the theoretical amount based on the quantity of cyanohydrin that disappears during the dehydration reaction.
		Catalytic hydrogenation of the second reaction solution produces a reaction mixture having almost twice the amount of aromatic substituted aliphatic carboxylic acid as was present after the first reaction-sequence.
	www.everypatent.com /comp/pat5696286.html (1718 words)

	[No title]
		Reactions of aldehydes and ketones with nucleophiles or bases all fall into one of two fundamental types of reactions.
		In the second class of reactions, the first step in the reaction is removal of the proton from the carbon adjacent to the carbonyl group to form an enolate anion (Equation 2).
		HCN is usually generated during the reaction by adding acid to sodium or potassium cyanide, as this reduces the risks involved in using a toxic gas.
	www.chem.wisc.edu /~newtrad/CurrRef/AIDStopic/AIDS.AldKetRxns.html (2217 words)

	Journal of the Brazilian Chemical Society - Synthesis of Analogues of 2-iodohexadecanal, a Regulator of Iodine ... (Site not responding. Last check: 2007-11-07)
		The reaction mixture was stirred at reflux for 2 h after which it was diluted with pentane (10 mL), washed with an aqueous NaOH solution (0.5%; 10 mL) and the aqueous phase extracted with pentane (3 x 10 mL).
		The reaction mixture was stirred for 24 h at rt.
		The reaction mixture was heated at 80 °C for 2 h, after which it was diluted with 1,2-dichloroethane (3 mL) and washed successively with water (2 x 5 mL) and an aqueous Na solution (0.1 N) until the color changed from pink to white.
	www.scielo.br /scielo.php?script=sci_arttext&pid=S0103-50531999000100002&lng=en&nrm=iso (7668 words)

	Carbos (Site not responding. Last check: 2007-11-07)
		It is possible to assign relative configuration using reactions which affect the chiral center, but then one must be very sure that the stereochemical effects at the chiral center are well understood.
		Cyanohydrin formation is another of the addition reactions characteristic of carbonyl compounds.
		The third reaction is a reduction of the original aldehyde group; this completes an end switching, and causes the sugar acid to be named in the L-series.
	instruct.uwo.ca /chemistry/223b-98/carbos.htm (4143 words)

	Imine Formation
		Such reactions are valuable, because the formation of bonds between carbon atoms is the most important part of synthesizing new organic molecules.
		If acid is not present, the first step is the reaction of the nucleophile with the carbonyl carbon, a process in which the carbonyl oxygen becomes negatively charged.
		It follows that if we are to understand why one reaction is faster than another, we have to think about how structural differences between one reaction and another influence the relative energy of the transition states and thus the activation energies.
	chemistry2.csudh.edu /rpendarvis/imineform.html (2465 words)

	Research interests, Professor Michael North, University of Newcastle
		Cyanohydrins are versatile starting materials for the synthesis of a wide range of other industrially important compounds, as well as being components of the pyrethroid insecticides in their own right.
		This reaction is currently being adapted to prepare a wide variety of polycyclic compounds which are suitable for use in target-orientated synthesis.
		Recently we have also become interested in yne-yne metathesis reactions, and in particular in the simultaneous use of yne-yne, ene-yne and ene-ene metathesis cascades in the synthesis of complex, poly-cyclic compounds.
	www.staff.ncl.ac.uk /michael.north/research.htm (1081 words)

	Cyanohydrin (Site not responding. Last check: 2007-11-07)
		Cyanohydrin is any of several compounds that contain both the CN and OH groups.
		The formation of cyanohydrins is an important step leading to the synthesis of carboxylic acids.
		Vicinal cyanohydrins can be formed from reacting a ketone with hydrogen cyanide(HCN) with a small amount of sodium cyanide(NaCN) as catalyst in the cyanohydrin reaction.
	www.pillscatalog.net /Cyanohydrin.html (257 words)

	Chem 381- CHAPTER TWO part 2
		The gasoline obtained by the direct distillation of crude petroleum is insufficient to meet demand (i.e., not enough is produced) and additional gasoline is obtained by the cracking of higher boiling petroleum fractions.
		The reaction is carried out by heating the higher fraction, such as gas oil at 450- 550 degrees C in the presence of an aluminum silica type catalyst.
		The reaction mixture is neutralized by ethylene cyanohydrin and then separated by distillation.
	web.umr.edu /~wlf/CHEM381/chap22.html (1917 words)

	Spartanburg SC \| GoUpstate.com \| Spartanburg Herald-Journal (Site not responding. Last check: 2007-11-07)
		Nucleophilic aliphatic substitution reactions of alkyl halides with metal cyanides.
		reaction of metal cyanides with aldehydes in the cyanohydrin reaction
		In organic reduction the nitrile is reduced by reacting it with hydrogen with a nickel catalyst; an amine is formed in this reaction.
	www.goupstate.com /apps/pbcs.dll/section?category=NEWS&template=wiki&text=nitrile (582 words)

	Energy Citations Database (ECD) - Energy and Energy-Related Bibliographic Citations (Site not responding. Last check: 2007-11-07)
		The reactions of sugars, such as D-xylose, D-dextrose, fructose, and maltose, with cyanide were studied at different times.
		The rate of cyanohydrin reaction measured in the space within a wooden box was greater than that in the space within a lead box of 16 cm wall thickness.
		It may be predicted that the ordinary background radiation energy, cosmic rays approaching the surface of our earth, contributes to the acceleration of the Kiliani's reaction.
	www.osti.gov /energycitations/product.biblio.jsp?osti_id=4669426&query_id=0 (270 words)

	Using Carbon Nucleophiles
		Reaction of RLi and RMgX with carbon dioxide
		The Wittig reaction is an important method for the formation of alkenes.
		2 reaction between triphenyl phosphine and an alkyl halide followed by treatment with a strong base such as an organolithium reagent.
	www.mhhe.com /physsci/chemistry/carey/student/olc/ch17carbonnucleophiles.html (423 words)

	The crystal structure of the hydroxynitrile lyase from the rubber tree Hevea brasiliensis suggests that this enzyme is ...
		The proposed sequence of reaction steps differs markedly from the reaction mechanism for (uncatalyzed) cynohydrin formation in solution, where direct attack of cyanide to the carbonyl is believed to occur.
		The proposed mechanism of enzyme-catalyzed cyanohydrin formation (or cleavage) differes markedly from the unkatalyzed reaction in solution, suggesting that evolution has preferred to adapt a hydrolase to the task of cyanogenesis rather than invent a new enzyme on the basis of the solution mechanism.
		Xu, L.L., Singh, B.K. and Conn, E.E. Purification and Characterization of Acetone Cyanohydrin Lyase from Linum usitatissimum.
	www.uni-graz.at /che3www/strubi/papers/full_text/hnl_native/paper.htm (6054 words)

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