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US4310688A Expired / Lapsed US ⏱️ 0.0 years remaining

Reduction of hydrolyzable chloride impurities in an isocyanatoalkyl ester of an organic carboxylic acid

Assignee: Dow Chemical Co
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Filing: 1979-10-22
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Granted: 1982-01-12
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Expires: 1999-10-22
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Abstract

Abstract The level of hydrolyzable chloride-containing impurities in an isocyanatoalkyl ester of an organic carboxylic acid is reduced by reacting the impurities with a vicinal epoxide-containing compound and then fractionally distilling the mixture to recover the isocyanatoalkyl ester. As an example, crude 2-isocyanatoethyl methacrylate (IEM) in a methylene chloride solution containing 0.084 weight percent of hydrolyzable chloride is contacted with a diglycidyl ether of bisphenol A at 23° C. This reaction mixture is then fractionally distilled to separate the IEM from the methylene chloride first cut and the epoxy resin residue. The hydrolyzable chloride level of the distilled IEM product is only 0.03 weight percent.

Inventors

  • 👤 Abel Mendoza

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 03:55
CPC Classifications
C; C07; C07C; C07C263/00; C07C263/18; C07C263/20

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 182 words
In a process for preparing an isocyanatoalkyl ester of an organic carboxylic acid represented by the formula ##STR6## wherein each R is independently hydrogen, alkyl, alkenyl, alkoxy, alkaryl, aralkyl or aryl; R' is hydrogen, C 1 -C 17 alkyl, C 2 -C 17 alkenyl, C 7 -C 20 alkaryl or C 6 -C 24 aryl and n is 2 or 3, said process comprising the steps of reacting a 2-oxazoline or 2-oxazine with phosgene in a water-immiscible, organic solvent in the presence of an aqueous solution of a hydrogen chloride acceptor and then separating the organic solution of the resulting isocyanatoalkyl ester from the aqueous phase, the improvement comprising the steps of: (a) contacting the isocyanatoalkyl ester in a liquid phase with a vicinal epoxide-containing compound, said epoxide-containing compound being present in a ratio of at least about 0.5 equivalent of epoxide per equivalent of hydrolyzable chloride, so as to effect substantial reaction of the epoxide-containing compound with the hydrolyzable chloride; and (b) separating the isocyanatoalkyl ester from the other components of the liquid mixture resulting from Step (a) by fractional distillation.
Claim 2
Dependent Claim 182 words
In a process for preparing an isocyanatoalkyl ester of an organic carboxylic acid represented by the formula ##STR6## wherein each R is independently hydrogen, alkyl, alkenyl, alkoxy, alkaryl, aralkyl or aryl; R' is hydrogen, C 1 -C 17 alkyl, C 2 -C 17 alkenyl, C 7 -C 20 alkaryl or C 6 -C 24 aryl and n is 2 or 3, said process comprising the steps of reacting a 2-oxazoline or 2-oxazine with phosgene in a water-immiscible, organic solvent in the presence of an aqueous solution of a hydrogen chloride acceptor and then separating the organic solution of the resulting isocyanatoalkyl ester from the aqueous phase, the improvement comprising the steps of: (a) contacting the isocyanatoalkyl ester in a liquid phase with a vicinal epoxide-containing compound, said epoxide-containing compound being present in a ratio of at least about 0.5 equivalent of epoxide per equivalent of hydrolyzable chloride, so as to effect substantial reaction of the epoxide-containing compound with the hydrolyzable chloride; and (b) separating the isocyanatoalkyl ester from the other components of the liquid mixture resulting from Step (a) by fractional distillation.
Claim 3
Dependent Claim 24 words
The process as described in claim 1, wherein Step (a) is conducted in the same organic solvent in which the isocyanatoalkyl ester is prepared.
Claim 4
Dependent Claim 35 words
The process as described in claim 1, which further comprises the step of separating by distillation the isocyanatoalkyl ester from the organic solution in which it is prepared and then conducting steps (a) and (b).
Claim 5
Dependent Claim 33 words
The process as described in claim 1 wherein the epoxide-containing compound is employed in step (a) in a ratio from about 0.75 to about 1.5 equivalents of epoxide per equivalent of hydrolyzable chloride.
Claim 6
Dependent Claim 34 words
The process as described in claim 3 wherein the epoxide-containing compound and the isocyanatoalkyl ester are contacted in step (a) in the presence of at least about 5 weight percent of an inert diluent.
Claim 7
Dependent Claim 14 words
The process as described in claim 5 wherein the inert diluent is methylene chloride.
Claim 8
Dependent Claim 24 words
The process as described in claim 4 wherein step (a) is conducted at a reaction temperature from about 5° C. to about 100° C.
Claim 9
Dependent Claim 33 words
The process as described in claim 1 wherein the isocyanatoalkyl ester is represented by the formula ##STR7## wherein R' is a C 1 -C 4 alkyl or a C 2 -C 4 alkenyl.
Claim 10
Dependent Claim 13 words
The process as described in claim 8 wherein R' is vinyl or isopropenyl.
Claim 11
Dependent Claim 11 words
The process as described in claim 8 wherein R' is isopropenyl.
Claim 12
Dependent Claim 36 words
The process as described in claim 7 further comprising the step of contacting the isocyanatoalkyl ester dissolved in a water-immiscible organic solvent with an aqueous solution of a weak base, following or contemporaneous with step (a).
Claim 13
Dependent Claim 19 words
The process as described in claim 7 wherein the epoxide-containing compound is ethylene oxide, 1,2-propylene oxide or 1,2-butylene oxide.
Claim 14
Dependent Claim 72 words
The process as described in claim 7 wherein the epoxide-containing compound is represented by the formula ##STR8## wherein R 5 , R 6 , R 7 and R 8 are each independently hydrogen, bromine or chlorine; Z is selected from the group consisting of oxygen, sulfur, --SO--, --SO 2 --, bivalent hydrocarbon radicals containing up to about 10 carbon atoms, --OR'O--, --OR'--O--R'--O--, --S--R'--S-- and ##STR9## wherein R' is a bivalent hydrocarbon radical.
Claim 15
Dependent Claim 22 words
The process as described in claim 13 wherein Z is an alkylene or alkylidene group having from 1 to 4 carbon atoms.
Claim 16
Dependent Claim 40 words
The process as described in claim 12 or 14 wherein the isocyanatoalkyl ester is 2-isocyanatoethyl methacrylate, this reactant having been prepared by the reaction of phosgene with 2-isopropenyl-2-oxazoline in the presence of an aqueous solution of a hydrogen chloride acceptor.

References Cited (Backward Citations)

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GB1280007A Cited
GB1252099A Cited
US3793362A Cited
GB1458747A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-01-11 1985-07-13 1986-01-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-01-11 1989-07-13 1990-01-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-01-11 1993-07-13 1994-01-12 $7700.00 Window Closed / Lapsed

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