GB913865A - Carboxylic acid esters of polyfunctional hydroxymethyl ethers and a process for their production - Google Patents

Carboxylic acid esters of polyfunctional hydroxymethyl ethers and a process for their production

Info

Publication number
GB913865A
GB913865A GB26239/60A GB2623960A GB913865A GB 913865 A GB913865 A GB 913865A GB 26239/60 A GB26239/60 A GB 26239/60A GB 2623960 A GB2623960 A GB 2623960A GB 913865 A GB913865 A GB 913865A
Authority
GB
United Kingdom
Prior art keywords
ether
diol
bis
formaldehyde
ethers
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
GB26239/60A
Inventor
Ernst Ploetz
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB913865A publication Critical patent/GB913865A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
    • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
    • C07C305/10—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/46—Preparation of carboxylic acid esters from ketenes or polyketenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/003—Esters of saturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Carboxylic esters of polyfunctional hydroxymethyl ethers are prepared by reacting 1 mol of an organic compound containing 2 to 6 primary or secondary alcoholic hydroxyl groups with at least 2 mols of formaldehyde or polymerized formaldehyde at an elevated temperature and treating the resultant hemiacetal with at least 2 mols of an acetylating and/or propionylating agent in the absence of water. The initial polyhydroxy compounds may contain nitrogen, oxygen or sulphur as hetero-atoms. Suitable polyhydroxy compounds include those derived from alkanes, alkenes and alkynes which may also contain aldehyde, ether, thioether, sulphone or amino groups. The products of the formulae <FORM:0913865/IV (b)/1> in which R1 represents an alkyl radical containing 1-20 carbon atoms or a radical of the formula -Z-O-CH2-O-CO-R5, R2 represents an alkyl radical containing 2-4 carbon atoms which may be substituted by a hydroxyl group or by a group of the formula -O-CH2-O-CO-R6, R3, R4, R5 and R6 represent methyl or ethyl radicals, A, B and Z represent alkylene radicals containing 2-4 carbon atoms, and X represents an equivalent of an anion, are claimed per se. The formaldehyde may be added in free form, either anhydrous or in aqueous solution, or in the form of its readily clearable polymers. Inert solvents may be present. The acylation is conducted under anhydrous conditions using acid anhydrides or halides, or ketenes. In Examples (3)-(5), (8), (9) and (12)-(17) using paraformaldehyde and acetic anhydride:- (3) triethylene glycol gives its bis-acetoxymethyl ether; (4) triethanolamine gives the acetate of its triacetyloxymethyl ether; (5) tetraethanolammonium chloride gives its tetraacetyloxymethyl ether; (8) hexaethylene glycol, (9) dihydroxydiethylsulphone, (12) but-2-ene-1, 4-diol, (13) but-2-yne-1,4-diol, (14) n-hexane-1,6-diol and (15) n-hexane-2,4-diol give their respective bis-acetyloxymethyl ethers; (16) and (17) sorbitol gives its tetrahydroxymethyldiacetyloxymethyl and hexaacetyloxymethyl ethers. Using pentaerythritol and acetic anhydride, (1) and (2) formaldehyde, and (7) aqueous formaldehyde, give (1) and (7) the tetraacetyloxymethyl, and (2) the mixed polyacetyloxymethyl, ethers of pentaerythritol. In other examples; (6) paraformaldehyde, propionic anhydride and dimethyldihydroxyethylammonium methosulphate give the bispropionic acid ester of dimethyldihydroxyethylammonium methosulphate bis-hemiacetal; (10) paraformaldehyde and ketene convert ethylene glycol to its bis-acetyloxymethyl ether; (11) paraformaldehyde and acetyl chloride convert butane-1,4-diol to its bis-acetyloxymethyl ether. Many other reagents are specified. The products are used in the treatment of textiles.
GB26239/60A 1959-07-29 1960-07-28 Carboxylic acid esters of polyfunctional hydroxymethyl ethers and a process for their production Expired GB913865A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB54222A DE1168905B (en) 1959-07-29 1959-07-29 Process for the preparation of the acetic or propionic acid esters of poly (hydroxyalkyl ether) compounds

Publications (1)

Publication Number Publication Date
GB913865A true GB913865A (en) 1962-12-28

Family

ID=6970531

Family Applications (1)

Application Number Title Priority Date Filing Date
GB26239/60A Expired GB913865A (en) 1959-07-29 1960-07-28 Carboxylic acid esters of polyfunctional hydroxymethyl ethers and a process for their production

Country Status (5)

Country Link
BE (1) BE593453A (en)
CH (1) CH393302A (en)
DE (1) DE1168905B (en)
GB (1) GB913865A (en)
NL (2) NL121555C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4298758A (en) * 1980-02-11 1981-11-03 The Dow Chemical Company Process for the production of propylene glycol esters from chloropropyl ethers

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE360980C (en) * 1920-04-10 1922-10-09 Hoechst Ag Process for the preparation of compounds of thiodiglycol
DE365170C (en) * 1920-06-09 1922-12-08 Hoechst Ag Process for the preparation of compounds of thiodiglycol
DE365171C (en) * 1920-06-09 1922-12-08 Hoechst Ag Process for the preparation of compounds of thiodiglycol
US2411136A (en) * 1942-03-21 1946-11-12 Monsanto Chemicals Esterification reactions
US2370055A (en) * 1942-08-25 1945-02-20 Wingfoot Corp Esterification
US2524921A (en) * 1946-08-30 1950-10-10 Westinghouse Electric Corp Unsaturated esters and synthetic resinous products produced therewith
US2644013A (en) * 1948-12-08 1953-06-30 Heyden Chemical Corp Process of producing polyhydric alcohol ethers from hemiformals and carbonyl compounds
US2719141A (en) * 1954-07-07 1955-09-27 Eastman Kodak Co Hydantoin esters of maleic anhydride copolymers
FR1144274A (en) * 1955-02-17 1957-10-11 Us Rubber Co Synthetic resin enhancements

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4298758A (en) * 1980-02-11 1981-11-03 The Dow Chemical Company Process for the production of propylene glycol esters from chloropropyl ethers

Also Published As

Publication number Publication date
NL254287A (en)
BE593453A (en)
NL121555C (en)
DE1168905B (en) 1964-04-30
CH393302A (en) 1965-06-15

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