GB691248A - Method for the production of acrylic nitrile - Google Patents

Method for the production of acrylic nitrile

Info

Publication number
GB691248A
GB691248A GB612/50A GB61250A GB691248A GB 691248 A GB691248 A GB 691248A GB 612/50 A GB612/50 A GB 612/50A GB 61250 A GB61250 A GB 61250A GB 691248 A GB691248 A GB 691248A
Authority
GB
United Kingdom
Prior art keywords
acetylene
column
temperature
solution
mixture
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB612/50A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Compagnie de Produits Chimiques et Electrometallurgiques Alais Froges et Camargue
Original Assignee
Compagnie de Produits Chimiques et Electrometallurgiques Alais Froges et Camargue
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Compagnie de Produits Chimiques et Electrometallurgiques Alais Froges et Camargue filed Critical Compagnie de Produits Chimiques et Electrometallurgiques Alais Froges et Camargue
Publication of GB691248A publication Critical patent/GB691248A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00Preparation of carboxylic acid nitriles
    • C07C253/08Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
    • C07C253/12Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon triple bonds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

<PICT:0691248/IV (b)/1> Acrylic nitrile is obtained by simultaneous passage of acetylene and hydrocyanic acid into an aqueous solution containing cuprous chloride and one or more alkali metal chlorides, the latter term including ammonium chloride, and then washing with water in a rectifying column the mixture of gases and vapours resulting from the reaction in order to obtain a solution of acrylic nitrile and a residual mixture of acetylene and vinyl acetylene, said mixture of gases and vapours being introduced into said rectifying column substantially at the reaction temperature, preferably 70 DEG to 100 DEG C. obtaining in the production of the acrylic nitrile, or after injection of steam thereinto, so that the aqueous acrylic nitrile solution shall flow out from the base of the column at a temperature within the range of from 20 DEG to 40 DEG C. and said residual mixture being then rectified in the presence of a counter-current flow of a substantially non-volatile solvent of vinyl acetylene and at a temperature approximating to the boiling-point of the latter, preferably at between 0 DEG and 10 DEG C., so as to obtain both a solution of vinyl-acetylene from which the latter is recoverable and acetylene which is reintroduced into the cycle of operations. Specified non-volatile solvents are gas oil, mineral oils and aniline and the solvent, e.g. gas oil, is preferably saturated with sulphur to prevent polymerization of the vinyl acetylene. In an example described with reference to the drawing, acetylene and hydrocyanic acid are introduced into reactor 1 which contains an aqueous solution comprising cuprous chloride, ammonium chloride and hydrochloric acid maintained at 70-75 DEG C. The effluent gas and vapour are introduced substantially at the reactor outlet temperature into the base of a rectifying column 2 as at c, water at a temperature of 2 DEG C. being added at the top of the column at such a rate that the effluent solution from the outlet e contains about 2 per cent acrylic nitrile. The residual gas mixture flows out of column 2 at a temperature of 5 DEG C. and enters the rectifying column 3 as at f, the column being filled with Raschig rings. Gas oil saturated with sulphur is introduced into the top of the column at a temperature of 4 DEG C. The vinyl acetylene solution flowing out at h is degassed by heating it to 140-150 DEG C. in the apparatus 4 and the vinylacetylene then cooled in cooler 5. Half the amount of vinyl acetylene is recycled to the bottom of cooler 3 while the remainder is withdrawn at i. The solvent flowing out from apparatus 4 is recycled to the top of column 3 via the cooler 7 which reduces its temperature to 4 DEG C. The acetylene from the top of column 3 is recycled to the reactor 1 through a recycling pump 8 and has added to it a volume of fresh acetylene equal to the sum total of the reacted acetylene plus the small amount which is drained off at j to eliminate the inert constituents brought in with the acetylene. If necessary steam may be added through the conduit k to the reaction mixture flowing from the reactor 1. Continuous distillation of the effluent solution from the apparatus 2 yields crude acrylonitrile containing ethanol and small amounts of hydrocyanic acid and divinyl acetylene. The results obtained are compared with those obtained in the same apparatus and with the same catalyst but in the absence of the solvent treatment.ALSO:<PICT:0691248/III/1> Acrylic nitrile is obtained by simultaneous passage of acetylene and hydrocyanic acid into an aqueous solution containing cuprous chloride and one or more alkali metal chlorides, the latter term including ammonium chloride, and then washing with water in a rectifying column the mixture of gases and vapours resulting from the reaction in order to obtain a solution of acrylic nitrile and a residual mixture of acetylene and vinyl acetylene, said mixture of gases and vapours being introduced into said rectifying column substantially at the reaction temperature, preferably 70 DEG to 100 DEG C, obtaining in the production of the acrylic nitrile, or after injection of steam thereinto, so that the aqueous acrylic nitrile solution shall flow out from the base of the column at a temperature within the range of from 20 DEG C to 40 DEG C, and said residual mixture being then rectified in the presence of a counter current flow of a substantially non-volatile solvent of vinyl acetylene and at a temperature approximating to the boiling point of the latter, preferably at between 0 DEG and 10 DEG C, so as to obtain both a solution of vinylacetylene from which the latter is recoverable and acetylene which is reintroduced into the cycle of operations. Specified non-volatile solvents are gas oil, mineral oils and aniline and the solvent, e.g. gas oil, is preferably saturated with sulphur to prevent polymerization of the vinyl acetylene. In an example described with reference to the drawing, acetylene and hydrocyanic acid are introduced into reactor 1 which contains an aqueous solution comprising cuprous chloride, ammonium chloride and hydrochloric acid maintained at 70-75 DEG C. The effluent gas and vapour are introduced substantially at the reactor outlet temperature into the base of a rectifying column 2 as at c, water at a temperature of 20 DEG C being added at the top of the column at such a rate that the effluent solution from the outlet e contains about 2 per cent acrylic nitrile. The residual gas mixture flows out of column 2 at a temperature of 5 DEG C and enters the rectifying column 3 as at f, the column being filled with Raschig rings. Gas oil saturated with sulphur is introduced into the top of the column at a temperature of 40 DEG C. The vinyl acetylene solution flowing out at h is degassed by heating it to 140-150 DEG C in the apparatus 4 and the vinylacetylene then cooled in cooler 5. Half the amount of vinyl acetylene is recycled to the bottom of cooler 3 while the remainder is withdrawn at i. The solvent flowing out from apparatus 4 is recycled to the top of column 3 via the cooler 7 which reduces its temperature to 40 DEG C. The acetylene from the top of column 3 is recycled to the reactor 1 through a recycling pump 8 and has added to it a volume of fresh acetylene equal to the sum total of the reacted acetylene plus the small amount which is drained off at j to eliminate the inert constituents brought in with the acetylene. If necessary steam may be added through a conduit k to the reaction mixture flowing from the reactor 1. Continuous distillation of the effluent solution from the apparatus 2 yields crude acrylonitrile containing ethanal and small amounts of hydrocyanic acid and divinyl acetylene. The results obtained are compared with those obtained in the same apparatus and with the same catalyst but in the absence of the solvent treatment.
GB612/50A 1949-01-12 1950-01-10 Method for the production of acrylic nitrile Expired GB691248A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR691248X 1949-01-12

Publications (1)

Publication Number Publication Date
GB691248A true GB691248A (en) 1953-05-06

Family

ID=9032780

Family Applications (1)

Application Number Title Priority Date Filing Date
GB612/50A Expired GB691248A (en) 1949-01-12 1950-01-10 Method for the production of acrylic nitrile

Country Status (1)

Country Link
GB (1) GB691248A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1090195B (en) * 1956-07-11 1960-10-06 Knapsack Ag Process for the simultaneous production of acrylic acid nitrile, monovinylacetylene and acetaldehyde
DE1119851B (en) * 1958-09-09 1961-12-21 Knapsack Ag Process for the simultaneous production of acrylic acid nitrile, monovinylacetylene and acetaldehyde

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1090195B (en) * 1956-07-11 1960-10-06 Knapsack Ag Process for the simultaneous production of acrylic acid nitrile, monovinylacetylene and acetaldehyde
DE1119851B (en) * 1958-09-09 1961-12-21 Knapsack Ag Process for the simultaneous production of acrylic acid nitrile, monovinylacetylene and acetaldehyde

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