Albemarle Corporation

Ethyl Corporation

Gerald M Sulzer

Chi Hung Cheng

Charles H Kolich

W Dirk Klobucar

John F Balhoff

R Woodrow Wilson, Jr

J Robert Adams, Jr

Joseph B Tedder, Jr

Matthew K Juneau

Epoxyalkanes are subjected to at least one of the following washing operations: (1) washing with aqueous inorganic base, and then with aqueous borohydride, or vice versa; or (2) washing with an aqueous solution of both inorganic base and borohydride. Undesirable odor is reduced or eliminated from alkanediol(s), if produced from the treated epoxyalkane(s) by hydrolysis. Use of such washing procedures in the production of alkanediols is also described.

Preventing undesired odor in and/or purifying alkanediols

Mixed together are (i) hydrogen peroxide; (ii) 1-alkene; (iii) quaternary ammonium salt wherein at least one of the substituents contains at least six carbon atoms; (iv) boric acid, or both a 1,2-diol and boric acid; and (v) a preformed catalyst solution formed from hydrogen peroxide, at least one aqueous inorganic acid, and at least one tungstate salt, while water is continuously removed, such that a 1,2-epoxide is formed. A new method for purifying 1,2-epoxyalkanes is also described.

Epoxidation of olefins

An aqueous solution of basic mercaptide salt and water-soluble peroxide are mixed together in a reaction zone and maintained under reaction conditions effective to produce a vapor phase comprising organic disulfide, and concurrently vapor phase is recovered from the reaction zone. The process is highly efficient and enables production of organic disulfides in high yield and purity. Not only is the process very easy and simple to carry out, but in addition the process (i) eliminates the need for forming an organic phase of liquid organic disulfide product and conducting a separation between such product and the total aqueous phase used in the reaction, (ii) enables efficient control of a highly exothermic reaction, and (iii) minimizes alkanesulfonic acid salt formation during the reaction.

Process for production of organic disulfides

N-hydrocarbylthiophosphoric triamide is separated or recovered from a liquid mixture comprising N-hydrocarbylthiophosphoric triamide, inert organic solvent, and optionally but preferably, tertiary amine, by continuously introducing a stream of the liquid mixture into a wiped film evaporator operating at a temperature in the range of about 60 to about 140.degree. C., and at a pressure that avoids solids formation on the heating surface of the wiped film evaporator, and continuously collecting the resultant N-hydrocarbylthiophosphoric triamide product.

Recovery of N-hydrocarbylthiophosphoric triamides and

A reaction mixture containing N-hydrocarbylthiophosphoric triamide or N-hydrocarbylphosphoric triamide ('Triamide') is formed by reacting ammonia with N-hydrocarbylaminothiophosphoryl dichloride or N-hydrocarbylaminophosphoryl dichloride in a liquid organic medium, in proportions of at least 16 moles of ammonia per mole of such dichloride and that keep in solution the ammonium chloride co-product formed in the reaction. The temperature of the reaction mixture is kept high enough to keep ammonium chloride-ammonia complex from forming a solid phase in the reaction mixture, but low enough to avoid significant reduction in Triamide yield. The reaction mixture is then caused/allowed to separate into an inorganic phase comprising ammonia, ammonium chloride and co-product thiophosphoric triamide or phosphoric triamide, and an organic phase comprising Triamide, liquid organic medium, dissolved ammonia and, usually, phosphorus impurities. These phases are separated from each other. The ammonia is removed from the organic phase to leave a concentrated solution of Triamide in residual liquid organic medium usually also containing phosphorus impurities. The Triamide is separated or recovered from this residual mixture by continuously introducing a stream of the liquid mixture into a wiped film evaporator operating at a temperature of about 60.degree.-140.degree. C., and at a pressure that avoids solids formation on the heating surface of the wiped film evaporator, and continuously collecting the Triamide product. Triamides are urease inhibitors for use with urea-based fertilizers.

Preparation and recovery of N-hydrocarbylthiophosphoric triamides or

Aqueous ammoniate solutions made during the manufacture of N-hydrocarbyl thiophosphoric triamides, consisting essentially of aqueous solutions of ammonium chloride and ammonia containing a water-soluble impurity normally tending to engender corrosion of ferrous metal are rendered corrosion-resistant by dissolving therein a small corrosion-inhibiting amount (e.g., up to about 5000 ppm (wt/wt) of a water-soluble salt or oxide of zinc, aluminum, arsenic, antimony or bismuth.

Inhibiting ferrous metal corrosion by aqueous ammoniate solutions

A substantially anhydrous mixture which comprises ammonium chloride, the triamide, and ammonia is formed either by adding ammonia to a mixture of the other components or by conducting, in the presence of the ammonia and an organic solvent, a reaction to form the triamide and ammonium chloride as co-products. In all cases the ammonia is present in a sufficient excess amount relative to the ammonium chloride to form a separate liquid phase in which the ammonium chloride solids dissolve. Such separate liquid phase is separated from the remainder of said mixture.

Separating ammonium chloride from N-hydrocarbylphosphoric triamide or

Continuously fed to and mixed in a first reactor are (i) a preformed mixture of primary hydrocarbyl monoamine, tertiary amine and liquid inert organic solvent, and (ii) thiophosphoryl chloride while removing heat of reaction to maintain the reaction temperature in the range of about -20.degree. C. to about +50.degree. C. A reaction mixture containing N-hydrocarbylaminothiophosphoryl dichloride is formed. Ammonia and an effluent stream from the first reactor are continuously fed to and mixed in a second reactor in proportions of at least about 16 moles, of ammonia per mole of N-hydrocarbylaminothiophosphoryl dichloride that produce a reaction mixture containing N-hydrocarbylthiophosphoric triamide, and that keep in solution ammonium chloride co-product formed in the reaction. Heat of reaction is removed so that the temperature is high enough to keep ammonium chloride-ammonia complex from forming a solid phase in this reaction mixture, but low enough to avoid significant reduction in yield of N-hydrocarbylthiophosphoric triamide being formed. Effluent is withdrawn from the second reactor so as to maintain a substantially constant volume of reaction mixture in the second reactor. The process eliminates a difficult filtration of the co-product ammonium chloride formed in the second reaction. Also, it possible to accomplish this in a continuous process, with improved efficiency in large scale production of the N-hydrocarbylthiophosphoric triamides. Moreover, the ammonium chloride can be readily converted in the process to an industrially useful liquid co-product mixture.

Preparation of N-hydrocarbylthiophosphoric triamides

Cyclic phosphonitrilic halide trimer is made in high yield and at a rapid rate by adding NH.sub.3 or ammonium halide to a pyridine-hydrogen halide complex and adding phosphorus pentahalide and a solvent for the trimer (e.g. monochlorobenzene) and heating the mixture to above 90.degree. C. to form trimer which dissolves in the solvent and then separating the trimer-solvent phase from the residue phase of pyridine-hydrogen halide complex and recovering trimer from the solvent phase and recycling the pyridine-hydrogen halide phase to a subsequent procedure conducted in the same manner. The process can also be adapted to produce linear species in high yield also.

Cyclic phosphonitrilic halide process

A process for making an alkali metal alkoxide (e.g. sodium alkoxide) of a halogen-substituted alcohol (e.g. fluorine-substituted alcohols) by dispersing an alkali metal (e.g. sodium) in a cycloalkane (e.g. cyclohexane) and adding the resultant dispersion to an ether (e.g. THF) solution of a halogen-substituted alcohol. The resultant alkali metal haloalkoxide solution can be reacted with a phosphonitrilic chloride polymer to introduce haloalkoxide substituents.

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Baton Rouge, LA, United States of America

Gerald M Sulzer