Abstract:
Aromatic substrates are Ar-brominated in high yield and selectivity by reacting the substrate with a brominating agent in the presence of at least about 0.19 gram per mmol of substrate of a zeolite catalyst which has an absorbed water content of no greater than about 7.5 weight percent.
Abstract:
Aromatic substrates such as fluorobenzene can be selectively brominated in high yield and conversion in short reaction periods by reacting the substrate with a brominating agent in a liquid reaction medium and in the presence of a catalyst composition formed by including in the medium a combination of (i) a shape selective HY or HM or zeolite catalyst, and (ii) at least one Lewis acid in a ratio of from 0.005 to 0.5 part by weight of (ii) per part by weight of (i). The bromination is performed at one or more temperatures in the range of 30 to 70° C., and the amount of the zeolite is no more than about 10 grams per mole of aromatic substrate.
Abstract:
In producing (.+-.)-2-(6-methoxy-2-naphthyl)propionic acid or precursor thereof from 2-bromo-6-methoxynaphthalene, use is made of 2-bromo-6-methoxynaphthalene formed by (a) methylating 6-bromo-2-naphthol with methyl chloride in a solvent comprising one or more compounds, RZ, where R is a hydrogen atom or an alkyl group, and Z is --OH or --CN provided that if Z is --CN, R is alkyl, and in the presence of a strong base; and (b) recovering and purifying 2-bromo-6-methoxynaphthalene so formed. Preferably, the 6-bromo-2-naphthol is formed by (1) reacting 1,6-dibromo-2-naphthol with hydrogen, in a solvent comprising (a) organic halide in which the halogen has an atomic number of 35 or less or (b) a mixture of water and such organic halide, and in the presence of catalytically effective amounts of (i) a tungsten carbide-based catalyst, and (ii) phase transfer catalyst; and (2) separating 6-bromo-2-naphthol from the organic halide solvent so that the 6-bromo-2-naphthol is substantially free of halogen-containing impurities before use in the above methylation reaction. This technology makes possible reductions in quantities of co-products formed, eliminates need for use of excess iron and/or dimethyl sulfate as reaction components, and makes possible improvements in plant operating efficiency. Precursors of (.+-.)-2-(6-methoxy-2-naphthyl)propionic acid formed from such 2-bromo-6-methoxynaphthalene are Grignard reagent of 2-bromo-6-methoxynaphthalene, bis(6-methoxy-2-naphthyl)zinc, 6-methoxy-2-naphthylzinc halide, 6-methoxy-2-naphthyllithium, 6-methoxy-2-naphthylcopper(I), bis(6-methoxy-2-naphthyl)cadmium, 6-methoxy-2-naphthylcadmium halide, and 6-methoxy-2-vinylnaphthalene.
Abstract:
Compound mixtures varying from liquids to solids can be prepared via a Michael reaction so that (1) their molecules correspond to the formula Z--C(E)E').sub.p --Q.sub.s wherein Z is alkyl, cycloalkyl, or --(CTT'--CT"G).sub.w --CTT'--CHT"G; Q is --(CTT'--CT"G).sub.t --CTT'--CHT"G; T, T', and T" are independently selected from hydrogen, G', and hydrocarbyl or predominantly hydrocarbyl organic groups containing up to 10 carbons, with the proviso that at least one of T, T', and T" must be hydrogen; E, E', G, and G' are independently selected from --COOR, --C(O)R', and --CN electron withdrawing groups in which R and R' represent alkyl or cycloalkyl groups of up to 10 carbons; p is zero or one; s is respectively two or one; and each of t and w represents zero or a positive integer and (2) at least 25% of the molecules contain at least three G groups. Among the more preferred products are the ester oils in which the esterifying groups contain 1-10 carbons and which have viscosities such as to make them suitable for use as lubricants.
Abstract:
Processes for producing 1,3,5-trimethyl-2,4,6-tris(3,5-dialkyl-4-hydroxybenzyl)benzene are provided, in particular such processes that utilize 2,6-di-tert-butylphenol, paraformaldehyde, a secondary amine, mesitylene, and acetic acid.
Abstract:
Described are multi-ring antioxidant products comprising at least one sulfur-bridged aromatic hydrocarbon compound substituted on at least one of its aromatic rings by at least one sterically hindered 3,5-dihydrocarbyl-4-hydroxybenzyl moiety. Such products have the formula: R—Sn—R[—S—R]m wherein each R is, independently, an aromatic hydrocarbon group having 6-12 carbon atoms, wherein m is 0-20, wherein n is 1-6 when m is 0, and when n is 1, m is 1-20; and wherein at least one of R, R1, and R2 is substituted by at least one such sterically hindered moiety. The preparation of such products and their use as antioxidants in compositions normally susceptible to oxidative degradation in oxygen or air, e.g., liquid fuel and lubricants, are also described.
Abstract:
This invention provides chain extender compositions. These compositions comprise (i) an aromatic primary diamine, and (ii) a component selected from the group consisting of: (a) an aliphatic secondary diamine; (b) an aliphatic primary diamine; (c) an aliphatic secondary diamine and an aliphatic primary diamine; (d) a diimine; and (e) a combination of any two or more of (a) through (d). When (ii) is (a), (a) has amino hydrocarbyl groups which are secondary or tertiary hydrocarbyl groups; when (ii) is (d), and (d) is an aromatic diimine, each imino hydrocarbylidene group has at least two carbon atoms. Processes for producing polyurethanes, polyureas, and polyurea-urethanes are also provided.
Abstract:
This invention provides chain extender compositions. These compositions comprise (i) an aromatic primary diamine, and (ii) a component selected from the group consisting of: (a) an aliphatic secondary diamine; (b) an aliphatic primary diamine; (c) an aliphatic secondary diamine and an aliphatic primary diamine; (d) a diimine; and (e) a combination of any two or more of (a) through (d). When (ii) is (a), (a) has amino hydrocarbyl groups which are secondary or tertiary hydrocarbyl groups; when (ii) is (d), and (d) is an aromatic diimine, each imino hydrocarbylidene group has at least two carbon atoms. Processes for producing polyurethanes, polyureas, and polyurea-urethanes are also provided.
Abstract:
This invention provides aromatic diimines which have imino hydrocarbylidene groups with at least two carbon atoms, and aromatic secondary diamines which have amino hydrocarbyl groups with at least two carbon atoms. Both the aromatic diimines and the aromatic secondary diamines either are in the form of one phenyl ring, or are in the form of two phenyl rings connected by an alkylene bridge; each position ortho to an imino group or an amino group bears a hydrocarbyl group. When in the form of one phenyl ring, there are two imino groups on the ring or two amino groups on the ring; the imino groups or amino groups are meta or para relative to each other. When in the form of two phenyl rings connected by an alkylene bridge, there is either one imino group or one amino group on each phenyl ring. Also provided are processes for forming diimines and secondary diamines.
Abstract:
Propargyl bromide is effectively stabilized against shock or thermal decomposition by use therewith of an environmentally acceptable inert liquid solvent that forms an azeotrope with propargyl bromide.