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GB1123335A - Preparation of acrylate dimers and trimers - Google Patents

Preparation of acrylate dimers and trimers

Info

Publication number
GB1123335A
GB1123335A GB3518/66A GB351866A GB1123335A GB 1123335 A GB1123335 A GB 1123335A GB 3518/66 A GB3518/66 A GB 3518/66A GB 351866 A GB351866 A GB 351866A GB 1123335 A GB1123335 A GB 1123335A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
alkyl
trimeric
optionally
acrylate
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
GB3518/66A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas 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
Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB1123335A publication Critical patent/GB1123335A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0255—Phosphorus containing compounds
    • B01J31/0264—Phosphorus acid amides
    • 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
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/12—Esters of monohydric alcohols or phenols
    • 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Catalysts (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to polymerizable mixtures comprising a dimeric and/or trimeric C1-C18-alkyl acrylate optionally in association with other comonomers such as methyl methacrylate and/or styrene, processes for polymerizing such mixtures and the polymer so prepared. (For the preparation of the dimeric and trimeric acrylates see Division C2.) The copolymers, which may typically contain 40% by weight of methyl methacrylate, 40% by weight of styrene and 20% by weight of the trimeric acrylate, are effective as coatings that are resistant to cracking and have high impact strength.ALSO:Preparation of dimeric and/or trimeric acrylates from an acrylate monomer of the formula CH2=CH.COOR in the presence of a catalyst of the formula <F\1> or <F\2> wherein R is an alkyl group containing from 1 to 18 carbon atoms; R1 and R4 are the same or different phenyl, alkyl group containing from 1 to 18 carbon atoms or alkyl substituted phenyl in which the alkyl substituent(s) contain(s) a total of from 1 to 8 carbon atoms; and R2 and R3 are (a) the same or different alkyl groups containing from 1 to 18 carbon atoms optionally containing one or more inert substituents or (b) when taken together with the nitrogen to which they are attached form a saturated cyclic amine group containing up to 5 carbon atoms, and optionally an oxygen or sulphur atom in the ring which may contain one or more alkyl substituents having a total of up to 6 carbon atoms. The reaction is carried out at a temperature in the range 0 DEG to 100 DEG C. optionally in the presence of an inert volatile organic solvent, e.g. hexane, benzene or toluene. The specified catalysts include N,N,N1,N1 - tetraethyl - or N,N,N1,N1 - tetramethyl - P - phenylphosphonous diamide and N,N-diethyl- or N,N-di-n-butyl-P,P-di-phenylphosphinous amide, and may be prepared as solutions by treating a suitably substituted dichlorosphosphine or chlorophosphine with an appropriate amine in one of the above-mentioned solvents and removing the amine salt which forms. Specified monomeric reactants include methyl, ethyl, iso-propyl-butyl, 2-ethylhexyl, t-dodecyl and octadecyl acrylates. Diethyl-2-methyleneglutarate and diethyl-2-methylene-4-carbethoxy pimelate are prepared from ethyl acrylate. Hydroquinone monomethyl ether may be present as inhibitor during the reaction.
GB3518/66A 1965-02-18 1967-01-26 Preparation of acrylate dimers and trimers Expired GB1123335A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US433773A US3342854A (en) 1965-02-18 1965-02-18 Method for the preparation of acrylate dimers and trimers

Publications (1)

Publication Number Publication Date
GB1123335A true GB1123335A (en) 1968-08-14

Family

ID=23721483

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3518/66A Expired GB1123335A (en) 1965-02-18 1967-01-26 Preparation of acrylate dimers and trimers

Country Status (8)

Country Link
US (1) US3342854A (en)
BE (1) BE673839A (en)
DE (1) DE1543429A1 (en)
DK (1) DK111359B (en)
FR (1) FR1460427A (en)
GB (1) GB1123335A (en)
IL (1) IL25198A (en)
NL (2) NL6600473A (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4451665A (en) * 1982-12-30 1984-05-29 E. I. Du Pont De Nemours And Company Process for dimerizing acrylates and methacrylates
CA2151112A1 (en) * 1994-06-13 1995-12-14 Michael Bennett Freeman High temperature polymerization process and products therefrom
JP6001386B2 (en) * 2012-09-07 2016-10-05 株式会社日本触媒 Method for producing 2-methyleneglutaric acid diester
JP2024536541A (en) 2021-10-18 2024-10-04 スペシャルティ オペレーションズ フランス Method for producing alkyl acrylate dimer
US20240400593A1 (en) 2021-10-18 2024-12-05 Specialty Operations France Bis-aminophosphines as catalysts for the dimerization of alkyl acrylates
CN116199579A (en) * 2022-12-21 2023-06-02 安徽华业香料股份有限公司 Preparation method of 2-methyl dimethyl glutarate
CN120916995A (en) 2023-04-13 2025-11-07 法国特种经营公司 Method for producing alkyl acrylate dimer
WO2024213503A1 (en) * 2023-04-13 2024-10-17 Specialty Operations France Process for preparing esteramide compounds

Also Published As

Publication number Publication date
BE673839A (en) 1966-06-16
NL6600473A (en) 1966-08-19
IL25198A (en) 1970-07-19
NL129494C (en)
DE1543429A1 (en) 1969-09-11
FR1460427A (en) 1966-11-25
DK111359B (en) 1968-08-05
US3342854A (en) 1967-09-19

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