GB745557A - Hydrogenation process for the production of polyhydric alcohols - Google Patents

Hydrogenation process for the production of polyhydric alcohols

Info

Publication number
GB745557A
GB745557A GB17025/53A GB1702553A GB745557A GB 745557 A GB745557 A GB 745557A GB 17025/53 A GB17025/53 A GB 17025/53A GB 1702553 A GB1702553 A GB 1702553A GB 745557 A GB745557 A GB 745557A
Authority
GB
United Kingdom
Prior art keywords
formaldehyde
mixture
carbohydrate
hydrogenation
catalyst
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
GB17025/53A
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.)
Celanese Corp
Original Assignee
Celanese Corp
Celanese Corp of America
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 Celanese Corp, Celanese Corp of America filed Critical Celanese Corp
Publication of GB745557A publication Critical patent/GB745557A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C29/74—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
    • 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
    • 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
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/18—Polyhydroxylic acyclic alcohols
    • C07C31/26—Hexahydroxylic alcohols

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

Polyhydric alcohols are produced from a mixture of carbohydrates resulting from the condensation of aqueous formaldehyde in the presence of a polyvalent metal catalyst, by a process comprising removing the polyvalent metal from the carbohydrate mixture, reducing the concentration of formaldehyde in the carbohydrate mixture to not more than 0.5 per cent by weight by distillation under acid conditions, and thereafter hydrogenating the carbohydrate mixture at a pH of 5 to 7 and under a hydrogenation pressure between 500 and 2,000 pounds p.s.i.g. in the presence of a hydrogenation catalyst. Preferably the polyvalent metal is removed by passing the carbohydrate mixture over an acidic cation-exchange resin, e.g. a phenol sulphonic acid-formaldehyde resin, or a sulphonated styrene-divinylbenzene copolymer, whereby the pH is decreased to between 2 and 3.5. Alternatively a precipitation method may be used; e.g. lead may be removed by adding oxalic or sulphuric acid, sodium oxalate or sodium sulphate. The formaldehyde may be removed by distillation at a pH of 3 to 5, a temperature of 102 DEG to 105 DEG C. and, if desired, under pressure. The pH of the mixture is then raised to a value in the range 5-7 either by treatment with an alkaline anion-exchange resin, such as phenylene-diamine-formaldehyde resin, triethylene tetramine-phenol-formaldehyde resin or the reaction product of an amine and a chloromethylated styrene-divinyl benzene copolymer, or by treatment with an alkaline alkali metal compound, such as sodium hydroxide or carbonate, or an organic base such as triethylamine. Suitable hydrogenation catalysts are Raney nickel or Raney cobalt. Preferably the carbohydrate content of the mixture to be hydrogenated should be less than 20 per cent and the temperature during hydrogenation should be not more than 150 DEG C. The products may be separated by distillation under reduced pressure. Water is removed at 100 mm. Hg, ethylene glycol at 1 mm. Hg, glycerol at 20-100 microns, and erythritol at 50-100 microns but at a higher temperature. The carbohydrate starting material comprising hydroxyaldehydes and hydroxy-ketones, is produced by condensation of formaldehyde in the presence of catalysts such as lead formate, lead nitrate, basic lead acetate, tin formate, tin chloride, cerium chloride or thorium chloride. A suitable process is described in Specification 740,398. A detailed example describes the condensation of aqueous formaldehyde in the presence of basic lead acetate to form a carbohydrate mixture which is subsequently treated with a cation-exchange resin to remove the catalyst, distilled to remove formaldehyde, treated with sodium hydroxide, and hydrogenated using a Raney nickel catalyst. Further examples illustrate the effect of varying amounts of formaldehyde present at the hydrogenation step.
GB17025/53A 1952-06-20 1953-06-19 Hydrogenation process for the production of polyhydric alcohols Expired GB745557A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US745557XA 1952-06-20 1952-06-20

Publications (1)

Publication Number Publication Date
GB745557A true GB745557A (en) 1956-02-29

Family

ID=22120193

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17025/53A Expired GB745557A (en) 1952-06-20 1953-06-19 Hydrogenation process for the production of polyhydric alcohols

Country Status (1)

Country Link
GB (1) GB745557A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4205138A (en) * 1977-08-26 1980-05-27 Bayer Aktiengesellschaft Polyurethane foams and elastomers prepared from low molecular weight polyhydroxyl compounds
US4247654A (en) * 1976-08-31 1981-01-27 Bayer Aktiengesellschaft Alkoxylated formose polyols and their use in polyurethane plastics
CN112452308A (en) * 2020-12-09 2021-03-09 昆明理工大学 Synthetic method and application of pyridine amide-containing adsorption polymer
CN113906005A (en) * 2019-06-04 2022-01-07 Oq化学有限责任公司 Through raneyTMCobalt-catalyzed continuous production of glycols from aldehydes

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4247654A (en) * 1976-08-31 1981-01-27 Bayer Aktiengesellschaft Alkoxylated formose polyols and their use in polyurethane plastics
US4205138A (en) * 1977-08-26 1980-05-27 Bayer Aktiengesellschaft Polyurethane foams and elastomers prepared from low molecular weight polyhydroxyl compounds
CN113906005A (en) * 2019-06-04 2022-01-07 Oq化学有限责任公司 Through raneyTMCobalt-catalyzed continuous production of glycols from aldehydes
CN113906005B (en) * 2019-06-04 2024-01-05 Oq化学有限责任公司 Through Raney TM Cobalt catalyzed continuous glycol production from aldehydes
CN112452308A (en) * 2020-12-09 2021-03-09 昆明理工大学 Synthetic method and application of pyridine amide-containing adsorption polymer
CN112452308B (en) * 2020-12-09 2022-10-25 昆明理工大学 Synthetic method and application of pyridine amide-containing adsorption polymer

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