FR2288075A1 - PREPARATION OF POLYOLS FROM CYCLIC ACETALS - Google Patents

PREPARATION OF POLYOLS FROM CYCLIC ACETALS

Info

Publication number
FR2288075A1
FR2288075A1 FR7601295A FR7601295A FR2288075A1 FR 2288075 A1 FR2288075 A1 FR 2288075A1 FR 7601295 A FR7601295 A FR 7601295A FR 7601295 A FR7601295 A FR 7601295A FR 2288075 A1 FR2288075 A1 FR 2288075A1
Authority
FR
France
Prior art keywords
acetals
diols
aldehydes
reacted
methyl
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.)
Granted
Application number
FR7601295A
Other languages
French (fr)
Other versions
FR2288075B1 (en
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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
Priority claimed from US493740A external-priority patent/US3929915A/en
Priority claimed from US05/493,741 external-priority patent/US3963754A/en
Priority claimed from US05/493,742 external-priority patent/US3963755A/en
Priority claimed from US05/495,510 external-priority patent/US4024159A/en
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of FR2288075A1 publication Critical patent/FR2288075A1/en
Application granted granted Critical
Publication of FR2288075B1 publication Critical patent/FR2288075B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/33—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties
    • C07C45/34—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds
    • C07C45/35—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of CHx-moieties in unsaturated compounds in propene or isobutene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D307/08—Preparation of tetrahydrofuran
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom

Landscapes

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

Abstract

To prepare the liquid acetals having a solubility of less than 10% by weight in 25 DEG C water, monoalcohols and/or diols having at least 4 carbon atoms and, in the case of diols, having not more than 3 carbon atoms between the diolhydroxyl groups are reacted with at least a stoichiometrically equivalent amount of aldehydes and/or dialdehydes. The reaction temperature is between 0 and 100 DEG C; the reaction is carried out in the presence of an acidic catalyst. The product obtained is a two-phase, aqueous-organic liquid in which the acetals are present in the organic phase. Advantageously one equivalent of alcohol is reacted with 1 to 1.5 equivalents of aldehyde. The novel process is used for example for preparing acetals having 6-membered rings, i.e. 1,3-dioxanes from 1,3-diols and aldehydes, especially for reacting acrolein with 2-methyl-1,3-propanediol to form 2-vinyl-5-methyl-1,3-dioxane as per the reaction scheme Product acetals with an olefinic double bond can be converted into corresponding acetal aldehydes by hydroformylation. The novel method of preparation makes it possible to obtain the acetals in a yield which is higher than that corresponding to the thermodynamic equilibrium.
FR7601295A 1974-07-31 1976-01-19 PREPARATION OF POLYOLS FROM CYCLIC ACETALS Granted FR2288075A1 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US493740A US3929915A (en) 1974-07-31 1974-07-31 Process for the production of butanediol
US05/493,741 US3963754A (en) 1974-07-31 1974-07-31 2-Vinyl-5-methyl-1,3-dioxane
US05/493,742 US3963755A (en) 1974-07-31 1974-07-31 Mixture of 2(2'-propanal)-5-methyl-1,3-dioxane and 2(3'-propanal)-5-methyl-1,3-dioxane
US49429274A 1974-08-02 1974-08-02
US49429174A 1974-08-02 1974-08-02
US05/495,510 US4024159A (en) 1974-08-07 1974-08-07 Process for the production of liquid acetals

Publications (2)

Publication Number Publication Date
FR2288075A1 true FR2288075A1 (en) 1976-05-14
FR2288075B1 FR2288075B1 (en) 1980-01-11

Family

ID=27560065

Family Applications (2)

Application Number Title Priority Date Filing Date
FR7517248A Granted FR2351935A1 (en) 1974-07-31 1975-06-03 PREPARATION OF ACETALS FROM ALDEHYDES AND ALCOHOLS AND / OR DIOLS
FR7601295A Granted FR2288075A1 (en) 1974-07-31 1976-01-19 PREPARATION OF POLYOLS FROM CYCLIC ACETALS

Family Applications Before (1)

Application Number Title Priority Date Filing Date
FR7517248A Granted FR2351935A1 (en) 1974-07-31 1975-06-03 PREPARATION OF ACETALS FROM ALDEHYDES AND ALCOHOLS AND / OR DIOLS

Country Status (3)

Country Link
BR (1) BR7504899A (en)
CH (1) CH624374A5 (en)
FR (2) FR2351935A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2376106A1 (en) * 1976-12-28 1978-07-28 Du Pont PROCESS FOR PREPARING POLYOLS FROM A CYCLIC ACETAL

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2962409D1 (en) * 1978-02-21 1982-05-19 Du Pont Process of hydroformylating cyclic acrolein acetals
FR2906807A1 (en) * 2006-10-09 2008-04-11 Arkema France PROCESS FOR THE SYNTHESIS OF CYCLIC ACETALS BY REACTIVE EXTRACTION OF A POLYOL IN A CONCENTRATED SOLUTION
BRPI0902550B1 (en) * 2009-01-05 2018-04-24 Senai/dr-ba-serviço Nacional De Aprendizagem Industrial, Departamento Regional Da Bahia BLOND GLYCERIN PURIFICATION PROCESS, FROM BIODIESEL TRANSESTERIFICATION

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2376106A1 (en) * 1976-12-28 1978-07-28 Du Pont PROCESS FOR PREPARING POLYOLS FROM A CYCLIC ACETAL

Also Published As

Publication number Publication date
FR2351935A1 (en) 1977-12-16
CH624374A5 (en) 1981-07-31
FR2288075B1 (en) 1980-01-11
BR7504899A (en) 1976-08-03
FR2351935B1 (en) 1980-02-29

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