GB852664A - Production of methacrylic acid and esters thereof - Google Patents

Production of methacrylic acid and esters thereof

Info

Publication number
GB852664A
GB852664A GB33178/58A GB3317858A GB852664A GB 852664 A GB852664 A GB 852664A GB 33178/58 A GB33178/58 A GB 33178/58A GB 3317858 A GB3317858 A GB 3317858A GB 852664 A GB852664 A GB 852664A
Authority
GB
United Kingdom
Prior art keywords
acid
ester
phosphate
nah2po4
graphite
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
GB33178/58A
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.)
Escambia Chemical Corp
Original Assignee
Escambia Chemical Corp
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 Escambia Chemical Corp filed Critical Escambia Chemical Corp
Publication of GB852664A publication Critical patent/GB852664A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/16—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr
    • B01J27/18—Phosphorus; Compounds thereof containing oxygen, i.e. acids, anhydrides and their derivates with N, S, B or halogens without carriers or on carriers based on C, Si, Al or Zr; also salts of Si, Al and Zr with metals other than Al or Zr
    • B01J27/1802—Salts or mixtures of anhydrides with compounds of other metals than V, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, e.g. phosphates, thiophosphates
    • B01J27/1806—Salts or mixtures of anhydrides with compounds of other metals than V, Nb, Ta, Cr, Mo, W, Mn, Tc, Re, e.g. phosphates, thiophosphates with alkaline or alkaline earth metals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form

Landscapes

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

Abstract

Methacrylic acid and/or an ester thereof are obtained by contacting at a temperature above 150 DEG C., e.g. between 150 and 500 DEG C., the vapours of alpha-hydroxyisobutyric acid or an ester thereof with a catalyst comprising an alkali metal phosphate and a support selected from graphite, silica gel, calcium sulphate or magnesium sulphate. In a modification an alcohol or phenol is fed to the reactor along with the material to be dehydrated. A vehicle or solvent (e.g. acetone or acetic acid) for the material to be dehydrated, may also be used to facilitate the introduction and vaporization of the material to be dehydrated and if desired the ester feed may be diluted with water or nitrogen. Specified esters which may be used as starting materials are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, isoamyl, decyl, dodecyl, tetradecyl, cetyl, phenyl, cresyl, tolyl, benzyl and resorcinyl alpha hydroxyisobutyric acid esters. The phosphate is preferably an alkali metal diacid phosphate, e.g. monosodium phosphate and phosphoric acid may also be present in the catalyst. The dehydration of alpha-hydroxyisobutyric acid in the presence of methanol can be made to give only methyl methacrylate instead of a mixture of methacrylic acid and methyl methacrylate by introducing an equilibrium concentration of methacrylic acid along with the hydroxy acid and methanol. Examples are given. A comparative example is also given in which silica gel and calcium sulphate are used alone, as catalyst for the dehydration of the methyl ester, only low yields of the unsaturated ester product being obtained in this case.ALSO:Alkali metal phosphate-containing catalysts used to effect dehydration of alphahydroxyisobutyric acid and/or an ester thereof to form methacrylic acid or ester thereof (see Group IV(b)) comprise an alkali metal phosphate and a support of graphite, silica gel, calcium sulphate or magnesium sulphate. Specified methods of preparation are as follows: (1) by heating a solution of NaH2PO4.H2O to about 60 DEG C., adding silica gel, heating the mixture to remove water and then further drying at 125 DEG C. for 24 hours, (2) by adding calcium sulphate and phosphoric acid to an aqueous solution of NaH2PO4.H2O, heating the mixture until dry and then further drying in a vacuum oven for 24 hours at 125 DEG C., (3) by mixing NaH2PO4.H2O and graphite, pressing into pellets, drying the pellets at 120 DEG C. for 16 hours and then regrinding the pellets, screening and repelleting, and (4) by boiling a solution of NaH2PO4.H2O to which phosphoric acid has been added, vacuum drying the residue and then breaking up the residue and mixing and pelleting it with graphite.
GB33178/58A 1957-10-29 1958-10-17 Production of methacrylic acid and esters thereof Expired GB852664A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US852664XA 1957-10-29 1957-10-29

Publications (1)

Publication Number Publication Date
GB852664A true GB852664A (en) 1960-10-26

Family

ID=22190497

Family Applications (1)

Application Number Title Priority Date Filing Date
GB33178/58A Expired GB852664A (en) 1957-10-29 1958-10-17 Production of methacrylic acid and esters thereof

Country Status (1)

Country Link
GB (1) GB852664A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0158694A1 (en) * 1984-04-18 1985-10-23 Ashland Oil, Inc. Oxydehydrogenation process

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0158694A1 (en) * 1984-04-18 1985-10-23 Ashland Oil, Inc. Oxydehydrogenation process

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