GB815163A - Improvements relating to the manufacture of acrylic acids or esters - Google Patents

Improvements relating to the manufacture of acrylic acids or esters

Info

Publication number
GB815163A
GB815163A GB19966/56A GB1996656A GB815163A GB 815163 A GB815163 A GB 815163A GB 19966/56 A GB19966/56 A GB 19966/56A GB 1996656 A GB1996656 A GB 1996656A GB 815163 A GB815163 A GB 815163A
Authority
GB
United Kingdom
Prior art keywords
acid
residues
manufacture
recovered
solution
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
GB19966/56A
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.)
Societe dElectro Chimie dElectro Metallurgie et des Acieries Electriques Dugine SA SECEMAU
Original Assignee
Societe dElectro Chimie dElectro Metallurgie et des Acieries Electriques Dugine SA SECEMAU
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 Societe dElectro Chimie dElectro Metallurgie et des Acieries Electriques Dugine SA SECEMAU filed Critical Societe dElectro Chimie dElectro Metallurgie et des Acieries Electriques Dugine SA SECEMAU
Publication of GB815163A publication Critical patent/GB815163A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/08Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00Preparation of carboxylic acid esters
    • C07C67/18Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group
    • C07C67/22Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group from nitriles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Acid ammonium sulphate and sulphuric acid are recovered from the residues from the manufacture of acids or esters of the acrylic group by sulphuric acid hydrolysis of nitriles or cyanhydrins which may be followed by esterification, whereby the acid ammonium sulphate contained in the said residues is crystallized out by cooling, the crystals being then separated from the mother solution containing unused sulphuric acid in excess together with residual organic constituents, the more or less carbonized heavy organic products are eliminated from the residues before or after cooling and separation of the crystals, and finally the recovered acid solution may be reconcentrated, if desired, for re-use in the hydrolysis reaction vessel. The crystallization of acid ammonium sulphate may be effected at temperatures between 10 DEG and 30 DEG C., and the crystals separated by filtration or pressing, e.g. in a centrifuge. To facilitate filtration, a part of the recovered acid solution may be taken off and fed back into the crystallizer. The recovered acid ammonium sulphate may be used for the manufacture of neutral ammonium sulphate. The carbonized heavy organic products may be eliminated from the residues by adsorbing them in hot or cold state, continuously or intermittently, on an adsorbent earth or carbon. The solution to be purified may be passed through a bed of adsorbent or the latter may be mixed with the solution and the suspension passed through a filter. Before the crystallization step and before or after the elimination of heavy organic products the residues may be evaporated under reduced pressure and the volatile organic products thereby separated. Alternatively, after the elimination of acid ammonium sulphate crystals and before treatment on the adsorbent, the recovered acid solution may be partly re-concentrated by heating in the presence of a small quantity of an oxidizing agent such as nitric acid. At the same time at least a part of the heavy organic products are cokified by this step and are later removed by passing over the adsorbent. The final reconcentration of the recovered acid solution may be effected by heating and/or by the addition of sulphuric acid or oleum. Flow diagrams, apparatus and detailed examples are described for the recovery of acid ammonium sulphate and sulphuric acid from the manufacture of ethyl acrylate by sulphuric acid hydrolysis of acrylic nitrile and esterification with ethanol, and from the manufacture of methyl methacrylate by sulphuric acid hydrolysis of acetone cyanhydrin and esterification with methanol.ALSO:The residues from the manufacture of acids or esters of the acrylic group <FORM:0815163/IV (b)/1> the free valencies of which are attached to hydrogen atoms or other radicals, by sulphuric acid hydrolysis of the corresponding nitriles or cyanhydrins which may be followed by esterification, are recovered by crystallizing out the acid ammonium sulphate contained in the residues by cooling, separating the crystals from the mother solution containing unused sulphuric acid in excess and almost the whole of the organic constituents of the initial residues, and eliminating the more or less carbonized heavy organic products from the residues before or after cooling and separation of the crystals, and the recovered acid solution is re-introduced into the hydrolysis reaction vessel, after reconcentration if necessary. The crystallization of acid ammonium sulphates may be effected at temperatures between 10 DEG and 30 DEG C., and the crystals separated by filtration or pressing. To facilitate filtration a part of the acid solution, before or after the adsorption treatment, may be taken off and recycled to the crystallizer. The carbonized heavy organic products may be eliminated by adsorbing them in hot or cold state, continuously or intermittently, on an adsorbent earth or carbon. The solution to be purified may be passed through a bed of adsorbent or the latter may be mixed with the solution and the suspension passed through a filter. Before the crystallization step, and before or after the elimination of heavy organic products, the residues may be evaporated under reduced pressure or under vacuum and the volatile organic products thereby separated, such as methacrylic acids or esters, intermediate products or alcohol in excess, may be recycled to the hydrolysis or esterification stages. Alternatively, after the elimination of ammonium bisulphate crystals and before treatment on the adsorbent, the recovered acid solution may be partly re-concentrated by heating in the presence of a small quantity of an oxidizing agent such as nitric acid. At the same time at least a part of the heavy organic products are cokified by this step and are later removed by passing over the adsorbent. The final reconcentration of the recovered acid solution may be effected by heating and/or by the addition of sulphuric acid or oleum. The re-use of this acid required for the manufacture of acrylic acid a concentration of 78 per cent and for the manufacture of methacrylic acid a concentration of 100 per cent. Flow diagrams, apparatus and detailed examples are described for the manufacture of ethyl acrylate by sulphuric hydrolysis of acrylic nitrile and esterification with ethanol, and for the manufacture of methyl methacrylate by sulphuric hydrolysis of acetone cyanhydrin and esterification with methanol.
GB19966/56A 1955-07-22 1956-06-27 Improvements relating to the manufacture of acrylic acids or esters Expired GB815163A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR815163X 1955-07-22

Publications (1)

Publication Number Publication Date
GB815163A true GB815163A (en) 1959-06-17

Family

ID=9267094

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19966/56A Expired GB815163A (en) 1955-07-22 1956-06-27 Improvements relating to the manufacture of acrylic acids or esters

Country Status (1)

Country Link
GB (1) GB815163A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4284832A (en) * 1980-04-28 1981-08-18 The United States Of America As Represented By The Secretary Of The Army Conversion of CS (tear gas) to o-chlorostyrene and ammonium sulfate
FR2619563A1 (en) * 1987-08-20 1989-02-24 Du Pont PROCESS WITH USE ACID RECYCLING FOR THE PRODUCTION OF ACID OR METHACRYLIC ESTERS

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4284832A (en) * 1980-04-28 1981-08-18 The United States Of America As Represented By The Secretary Of The Army Conversion of CS (tear gas) to o-chlorostyrene and ammonium sulfate
FR2619563A1 (en) * 1987-08-20 1989-02-24 Du Pont PROCESS WITH USE ACID RECYCLING FOR THE PRODUCTION OF ACID OR METHACRYLIC ESTERS

Similar Documents

Publication Publication Date Title
GB1532659A (en) Regeneration of absorbent solutions used for removing gaseous acid impurities from gaseous mixtures
US4100189A (en) Recovery of acetic acid from dilute aqueous solutions thereof
ES8504623A1 (en) Process and apparatus for the concentration and purification of sulfuric acid containing organic impurities.
US2890101A (en) Recovery of ammonium bisulphate from the distillation residues from the manufacture of acrylic acids and their esters
GB815163A (en) Improvements relating to the manufacture of acrylic acids or esters
US2805733A (en) Purification of ethylene
ATE3641T1 (en) PROCESS FOR SEPARATING URSODESOXYCHOLIC ACID AND CHENODESOXYCHOLIC ACID AND PRODUCTS OBTAINED DURING THE PROCESS.
GB788276A (en) A process for the purification of phthalic acids
GB1135063A (en) Process for the purification of malic acid
US2816923A (en) Conversion of maleic acid to fumaric acid
US2833824A (en) Purification of n, n&#39;-diphenyl-p-phenylenediamine
US3919396A (en) Phosphoric acid purification
US2752355A (en) Process for the preparation of nicotinamide
US2997502A (en) Bromination of salicylanilide
US3367950A (en) Process for the isolation of cholecalciferol from a mixture obtained on irradiation of 7-dehydrocholesterol
US2935528A (en) Calcium pantothenate and a method for treating same
US2809986A (en) Method for the purification of malononitrile
US2971011A (en) Process of preparing trimellitic anhydride
US4629614A (en) Process for decontaminating phosphoric acid
GB978877A (en) Improvements in or relating to a separation of carbamic acid esters
US3996336A (en) Purification of phosphoric acid
US2365493A (en) Purification of p-phenetidine
GB834614A (en) Process of producing crystalline ammonium bifluoride
US2651643A (en) Purification of desoxycholic acid
GB928783A (en) Purification of solutions obtained in the production of hydrogen peroxide