GB730759A - Improvements in or relating to the production of trimethylolpropane - Google Patents

Improvements in or relating to the production of trimethylolpropane

Info

Publication number
GB730759A
GB730759A GB21888/53A GB2188853A GB730759A GB 730759 A GB730759 A GB 730759A GB 21888/53 A GB21888/53 A GB 21888/53A GB 2188853 A GB2188853 A GB 2188853A GB 730759 A GB730759 A GB 730759A
Authority
GB
United Kingdom
Prior art keywords
mixture
acid
added
trimethylolpropane
salts
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
GB21888/53A
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.)
Hoechst AG Werk Kalle Albert
Original Assignee
Chemische Werke Albert
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 Chemische Werke Albert filed Critical Chemische Werke Albert
Publication of GB730759A publication Critical patent/GB730759A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/18—Polyhydroxylic acyclic alcohols
    • C07C31/22—Trihydroxylic alcohols, e.g. glycerol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/18—Polyhydroxylic acyclic alcohols
    • C07C31/20—Dihydroxylic alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/75—Reactions with formaldehyde
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/19—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing hydroxy groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

In a process for the production of trimethylolpropane by p condensing butyraldehyde and formaldehyde under alkaline conditions to give a reaction mixture containing trimethylolpropane and formic acid salts, the said reaction mixture is taken up in a solvent in which trimethylolpropane is soluble but in which the said formic acid salts are substantially insoluble, the resulting mixture is dehydrated to effect separation of the formic acid salts which are removed from the mixture whereafter a suitably small quantity of an inorganic acid reacting substance is added which will convert the remaining formates to inorganic salts and formic acid and the resulting mixture is distilled under reduced pressure. The formates are usually alkali and alkaline earth metal formates. Solvents mentioned are alcohols, especially butanol or higher alcohols, which permit the removal of water from the mixtures by azeotropic distillation, which is preferably conducted under reduced pressure. Inorganic acid-reacting substances mentioned are mineral acids, inorganic acid salts, boron trifluoride or salts which are easily hydrolysed such as aluminium sulphate. Water may be introduced into the mixture with the acid substances and the mixture may be heated. In examples: butyraldehyde, formaldehyde and sodium hydroxide solution are reacted together, the reacted mixture is adjusted to a pH value of 7, n-butanol is added and the mixture refluxed until water is removed. Sodium formate is separated and butanol removed from the mixture under reduced pressure. Phosphoric acid is then added to the residue and trimethylolpropane is distilled under vacuum (1); water is added at the same time as the phosphoric acid in a process otherwise similar to (1), (2); in processes otherwise similar to (1) sodium hydrogen sulphate and water and concentrated sulphuric acid are added instead of phosphoric acid (3) and (4); (1) is repeated using freshly precipitated calcium hydroxide instead of sodium hydroxide (5); and concentrated sulphuric acid is used instead of phosphoric acid in a process similar to (5), (6).
GB21888/53A 1952-11-18 1953-08-07 Improvements in or relating to the production of trimethylolpropane Expired GB730759A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE730759X 1952-11-18

Publications (1)

Publication Number Publication Date
GB730759A true GB730759A (en) 1955-05-25

Family

ID=6637090

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21888/53A Expired GB730759A (en) 1952-11-18 1953-08-07 Improvements in or relating to the production of trimethylolpropane

Country Status (1)

Country Link
GB (1) GB730759A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2865819A (en) * 1956-06-25 1958-12-23 Eastman Kodak Co Purification of neopentylglycol by azeotropic distillation
US3076854A (en) * 1955-12-05 1963-02-05 Heyden Newport Chemical Corp Recovery of trimethylolpropane
US3183274A (en) * 1956-10-09 1965-05-11 Celanese Corp Trimethylolpropane
US3483264A (en) * 1966-07-08 1969-12-09 Union Starch & Refining Co Inc Purification of polyhydric alcohols

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3076854A (en) * 1955-12-05 1963-02-05 Heyden Newport Chemical Corp Recovery of trimethylolpropane
US2865819A (en) * 1956-06-25 1958-12-23 Eastman Kodak Co Purification of neopentylglycol by azeotropic distillation
US3183274A (en) * 1956-10-09 1965-05-11 Celanese Corp Trimethylolpropane
US3483264A (en) * 1966-07-08 1969-12-09 Union Starch & Refining Co Inc Purification of polyhydric alcohols

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