Propylene Glycol → Propylene Glycol

HRID 1446946Notes

Reaction equation

HRID 1446946 reaction equation
[H][H].[CH2:3]([OH:7])[CH:4]([OH:6])[CH3:5].C(O)C[CH2:10][CH2:11][OH:12].C(O)[CH2:15][CH:16]([OH:18])[CH3:17].[CH2:20]([C:22](CO)(CO)[CH2:23][CH3:24])[OH:21].OCC(CO)(CO)CO.OC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>OCC(CO)O.C(O)CO>[CH2:3]([OH:7])[CH:4]([OH:6])[CH3:5].[CH2:11]1[O:12][CH2:10]1.[CH2:15]1[O:18][CH:16]1[CH3:17].[CH2:20]1[O:21][CH:22]1[CH2:23][CH3:24]

Participants

13

Reactant 7

HCID 1030Propylene GlycolHCID 5780SorbitolHCID 6510TrimethylolpropaneHCID 78961,3-ButanediolHCID 80641,4-ButanediolHCID 8285PentaerythritolHCID 178418361HCID 178418361, compound

Product 4

HCID 1030Propylene GlycolHCID 6354Ethylene OxideHCID 6378Propylene OxideHCID 78341,2-Epoxybutane

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 753GlycerolSolvent2×

Procedure

Exemplary organic compounds having at least two reactive hydrogen-containing groups includes (1) hydroxyl group-containing compounds such as (a) diols such as ethylene glycol, propylene glycol, 1,4-butylene glycol, 1,3-butylene glycol, polyethylene glycol and polypropylene glycol; (b) polyols such as glycerine, trimethylolpropane, pentaerythritol and sorbitol; (c) polyester polyols such as polyether polyols having a molecular weight of about 500 to about 100,000 obtained by addition reaction of at least one polyhydric alcohol such as glycerine and propylene glycol to at least one alkylene oxide such as ethylene oxide, propylene oxide and 1,2-butylene oxide, polyether polyols obtained by reaction of an alkylene oxide with a polyfunctional compound such as ethylene diamine and ethanolamine and polytetramethylene glycols obtained by ring-opening polymerization of tetrahydrofuran; (d) polyester polyols such as polyester polyols having a molecular weight of about 500 to about 100,000 obtained by condensation reaction of at least one dicarboxylic acid such as succinic acid, adipic acid, sebacic acid, dimeric acid, maleic anhydride, phthalic anhydride, isophthalic acid and terephthalic acid with at least one polyhydric alcohol such as ethylene glycol, propylene glycol, diethylene glycol, butylene glycol, neopentyl glycol, trimethylolpropane and glycerine; (e) acrylic polyols such as acrylic polyols having a molecular weight of about 500 to about 100,000 obtained by polymerizing at least one acrylate or methacrylate having at least one hydroxyl group in the molecule such as 2-hydroxyethyl acrylate, hydroxypropyl acrylate, 2-hydroxyethyl methacrylate and hydroxypropyl methacrylate and at least one acrylate or methacrylate such as methyl acrylate, ethyl acrylate, isopropyl acrylate, n-butyl acrylate, 2-ethylhexyl acrylate, methyl methacrylate, ethyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, n-hexyl methacrylate and lauryl methacrylate in the presence or absence of at least one compound selected from unsaturated carboxylic acids such as acrylic acid, methacrylic acid and itaconic acid, unsaturated amides such as acrylamide, N-methylolacrylamide and diacetone acrylamide and other polymerizable monomers such as styrene, glycidyl methacrylate, vinyltoluene, acrylonitrile; (2) other hydroxyl group-containing compounds such as polybutadienes having at least two terminal hydroxyl groups, polythioether polyols, polythioester polyols, polyacetal polyols, polycarbonate polyols and polyesteramide polyols; and (3) any mixtures of at least one hydroxyl group-containing compound as described above with at least one compound having at least two reactive hydrogen containing groups selected from (a) primary or secondary amino group-containing compounds such as diamines such as ethylenediamine, trimethylenediamine, 1,2-diaminopropylenediamine, tetramethylenediamine, hexamethylenediamine, 1,4-diaminocyclohexane, xylylenediamine, trimethylhexamethylenediamine, diaminodiphenylmethane and isophoronediamine, polyamines such as diethylenetriamine, triethylenetetramine, polyamines obtained by addition reaction of at least one alkylene polyamine such as diethylenetriamine and triethylenetetramine with at least one alkylene oxide such as ethylene oxide and propylene oxide and other modified polyamines, (b) carboxyl group-containing compounds such as liquid polybutadienes having at least two terminal carboxyl groups, (c) thiol group-containing compounds such as dithiols such as ethanediol and, 1,4-butanediol, polythiols such as trithioglycerine, polyether polythiols obtained by addition reaction of at least one polythiol with at least one alkylene oxide and polythioester polythiols obtained by condensation reaction of at least one dicarboxylic acid with at least one polythiol and (d) epoxy group-containing compounds such as epoxy resins having a molecular weight of about 500 to about 100,000 such as novolac type, epichlorohydrin type, cyclic oxirane type, glycidyl ether type, glycidyl ester type, polyglycol ether type, glycol ether type, epoxidated aliphatic unsaturated compound type, epoxidated fatty acid ester type, polycarboxylic acid ester type, aminoglycidyl type or resorcin type epoxy resins.

Workup

  1. additioncontaining groups

Sources & evidence

ORD record
ord-194d3c85bf6d49efb6be3ca2f98ca580
Source dataset
uspto-grants-1982_02
Patent number
US04314048

Reaction notes

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