GB890083A - Acylation of hydroxy compounds with vinyl esters - Google Patents

Acylation of hydroxy compounds with vinyl esters

Info

Publication number
GB890083A
GB890083A GB3654258A GB3654258A GB890083A GB 890083 A GB890083 A GB 890083A GB 3654258 A GB3654258 A GB 3654258A GB 3654258 A GB3654258 A GB 3654258A GB 890083 A GB890083 A GB 890083A
Authority
GB
United Kingdom
Prior art keywords
starch
vinyl
reaction
acetate
acid
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
GB3654258A
Inventor
John V Tuschhoff
Clifford E Smith
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.)
Primary Products Ingredients Americas LLC
Original Assignee
Tate and Lyle Ingredients Americas LLC
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 Tate and Lyle Ingredients Americas LLC filed Critical Tate and Lyle Ingredients Americas LLC
Priority to GB3654258A priority Critical patent/GB890083A/en
Publication of GB890083A publication Critical patent/GB890083A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B31/00—Preparation of derivatives of starch
    • C08B31/02—Esters
    • C08B31/04—Esters of organic acids, e.g. alkenyl-succinated starch

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

Polysaccharides are acylated by reacting with the vinyl ester of an aliphatic monocarboxylic acid, for example vinyl formate, acetate, propionate or butyrate in the presence of water under alkaline conditions. Polysaccharides mentioned are gum arabic, agar-agar, alginic acid, inulin and particularly starch. Suitable alkaline catalysts are the hydroxides and carbonates of the alkali metals, alkyl tertiary amines and the quaternary ammonium hydroxides. Starch of the waxy or non-waxy type derived from root, stem or seed may be used. The reaction of starch with the vinyl esters is moderately rapid over the range of 75 DEG F. to 115 DEG F. The starch may be used as an aqueous slurry of granular unpasted starch or as an alkaline aqueous starch paste. The mixture may be held at a pH in the range of 7,5 to 12,5. On completion of the reaction, the reaction mixture is neutralized to pH 6,5 with an acid, e.g. hydrochloric or sulphuric, and the modified granular starch recovered by filtration and drying. Examples describe the reaction commercial corn starch with vinyl acetate in the presence of NaOH, LiOH, KOH, Na2CO3, K2CO3, NH4OH or triethylamine; the reaction corn starch with vinyl formate, acetate, propionate, butyrate, crotonate, 2-ethylhexanoate or stearate using Na2CO3, NaOH or KOH as catalyst; the reaction of various types of native starch, thickboiling, acid-modified and hypochlorite oxidized corn starches with vinyl acetate using Na2CO3 or NaOH. Specification 489,330 is referred to.ALSO:Aliphatic hydroxy compounds are acylated by reacting with the vinyl ester of an aliphatic monocarboxylic acid in the presence of water under alkaline conditions. A pH of 9-10 is preferred. Suitable alkaline catalysts are hydroxides and carbonates of the alkali metals, alkyl tertiary amines and quaternary ammonium hydroxides. Vinyl esters mentioned are vinyl formate, acetate, propionate or butyrate. Hydroxy compounds specified are pentaerythritol, sorbitol, dextrose, sucrose, and a -methylglucoside. The process takes place at room temperature but raised temperature may be used, e.g. refluxing at 75 DEG C. Examples describe the preparation of glycerin diacetate, dextrose triacetate, sucrose tetraacetate, ethylene glycol monoacetate and the acetylation of corn syrup solids. Specification 489,330 is referred to.
GB3654258A 1958-11-13 1958-11-13 Acylation of hydroxy compounds with vinyl esters Expired GB890083A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3654258A GB890083A (en) 1958-11-13 1958-11-13 Acylation of hydroxy compounds with vinyl esters

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3654258A GB890083A (en) 1958-11-13 1958-11-13 Acylation of hydroxy compounds with vinyl esters

Publications (1)

Publication Number Publication Date
GB890083A true GB890083A (en) 1962-02-28

Family

ID=10389101

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3654258A Expired GB890083A (en) 1958-11-13 1958-11-13 Acylation of hydroxy compounds with vinyl esters

Country Status (1)

Country Link
GB (1) GB890083A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2509292A1 (en) * 1981-07-10 1983-01-14 Upjohn Co BASED CATALYZED ACYLATION PROCESS USING ENERAL ESTERS
WO2007082149A1 (en) * 2006-01-06 2007-07-19 Comstock, Bob Production of sugar esters from vinyl fatty acid esters

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2509292A1 (en) * 1981-07-10 1983-01-14 Upjohn Co BASED CATALYZED ACYLATION PROCESS USING ENERAL ESTERS
WO2007082149A1 (en) * 2006-01-06 2007-07-19 Comstock, Bob Production of sugar esters from vinyl fatty acid esters

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