GB1037650A - Improvements in and relating to the preparation of methylene-2 propanediol-1,3 and its derivatives - Google Patents

Improvements in and relating to the preparation of methylene-2 propanediol-1,3 and its derivatives

Info

Publication number
GB1037650A
GB1037650A GB4654163A GB4654163A GB1037650A GB 1037650 A GB1037650 A GB 1037650A GB 4654163 A GB4654163 A GB 4654163A GB 4654163 A GB4654163 A GB 4654163A GB 1037650 A GB1037650 A GB 1037650A
Authority
GB
United Kingdom
Prior art keywords
propanediol
methylene
crotonaldehyde
cyclopentadiene
prepared
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
GB4654163A
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 GB1037650A publication Critical patent/GB1037650A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
    • C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
    • C07C33/035—Alkenediols

Landscapes

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

Abstract

Methylene-2-propanediol-1,3 and its derivatives ar prepared by (a) reacting in a DielsAlder reaction an a ,b -ethylenic aldehyde of formula <FORM:1037650/C2/1> in which R1 and R2 are hydrogen or alkyl, aromatic hydrocarbon or heterocyclic groups, with a dienic compound; (b) subjecting the cyclic aldehyde so obtained to the action of formaldehyde in alkaline medium to produce the corresponding gem-dimethylolated derivative by an aldolization reaction followed by a Cannizzaro reaction; and (c) decomposing the product of (b) by heating to form the ethylenic diol and regenerating the dienic compound employed in the first stage. Suitable dienic compounds are, for example, butadiene, isoprene, piperylene, dimethyl - 2,3 - butadiene, cyclopentadiene, cyclohexadiene-1,3, furan, anthracene and naphthalene. Suitable ethylenic aldehydes are, for example, acrolein, crotonaldehyde, penten - 2 - al, methyl - 3 - crotonaldehyde, hexen-2-al, hexadien-2,4-al, hepten-2-al, cinnamic aldehyde and b -furylacrolein. In the examples: (a) methylene-2-propane diol-1,3 is prepared from acrolein and anthracene or cyclopentadiene and (b) ethylidine-2-propanediol-1,3 is prepared from cyclopentadiene and crotonaldehyde.
GB4654163A 1962-11-27 1963-11-25 Improvements in and relating to the preparation of methylene-2 propanediol-1,3 and its derivatives Expired GB1037650A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR916759A FR1350723A (en) 1962-11-27 1962-11-27 Process for the preparation of 2-methylene propanediol-1-3 and its derivatives

Publications (1)

Publication Number Publication Date
GB1037650A true GB1037650A (en) 1966-08-03

Family

ID=8791645

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4654163A Expired GB1037650A (en) 1962-11-27 1963-11-25 Improvements in and relating to the preparation of methylene-2 propanediol-1,3 and its derivatives

Country Status (3)

Country Link
FR (1) FR1350723A (en)
GB (1) GB1037650A (en)
LU (1) LU44797A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5202465A (en) * 1991-06-26 1993-04-13 Basf Aktiengesellschaft Preparation of 2-methylenepropane-1,3-diol dicarboxylates

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5202465A (en) * 1991-06-26 1993-04-13 Basf Aktiengesellschaft Preparation of 2-methylenepropane-1,3-diol dicarboxylates

Also Published As

Publication number Publication date
LU44797A1 (en) 1964-01-13
FR1350723A (en) 1964-01-31

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