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Preparation of substituted phthalic anhydride, especially 4-chlorophthalic anhydride

A technology of phthalic anhydride and alkyl phthalimide, which is applied in the fields of carboxylic anhydride preparation, amide preparation, organic chemistry, etc., and can solve problems such as expensive and difficult to separate

Inactive Publication Date: 2006-03-22
SABIC INNOVATIVE PLASTICS IP BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing routes for the synthesis of 4-chlorophthalic anhydride result in a mixture of isomers that are difficult to separate or limited by being expensive

Method used

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  • Preparation of substituted phthalic anhydride, especially 4-chlorophthalic anhydride
  • Preparation of substituted phthalic anhydride, especially 4-chlorophthalic anhydride
  • Preparation of substituted phthalic anhydride, especially 4-chlorophthalic anhydride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1. Synthesis of N-methyl-4-chlorophthalimide (VIII)

[0039] Charge 186.5 g (1 mole) of 4-chlorotetrahydrophthalic anhydride into a suitably configured glass reaction vessel and heat to 150° C. under nitrogen protection. Methylamine gas (32 grams, 1.03 moles) was then introduced subsurface of the reaction vessel for 30 minutes. The reaction mixture was then heated at 180° C. for 3 hours. The product was then distilled to give N-methyl-4-chlorophthalimide in about 95% yield.

Embodiment 2

[0040] Example 2. Synthesis of 4-chlorotetrahydrophthalic anhydride (IX)

[0041] 156.9 g (1.6 moles) of maleic anhydride and 250 ml of toluene were added to the flask. 25 ml of toluene was removed by distillation to dry the solution. 150 g (1.69 moles) of chloroprene dissolved in 250 ml of xylene was slowly added to the flask. The total addition took 30 minutes. The resulting solution was then heated at 55°C for 3 hours. The solution was then distilled to remove the solvent. The remaining material was distilled at 160-165° C. (1-2 mm pressure) to obtain 4-chlorotetrahydrophthalic anhydride (253 g) with a yield of 85%.

Embodiment 3

[0042] Example 3. Synthesis of 4-chlorophthalic anhydride (III)

[0043] 1.5g of 4-chlorotetrahydrophthalic anhydride, 0.262g of N-methyl-4-chlorophthalimide, 0.841g of triethylamine and 20ml of water were added to a 50ml resealable stainless steel tube. The tube was sealed and heated in an oil bath at 170°C for 3 hours, then cooled to room temperature.

[0044] A small sample in the aqueous phase was analyzed by means of GCMS. The analysis revealed that 83.2% of the exchanges took place. Analysis also showed that the reaction mixture consisted of 2.4 mol% N-methyl-4-chlorophthalimide, 11.9 mol% N-methyl-4-chlorotetrahydrophthalimide, 11.9 mol % of 4-chlorophthalic anhydride (as the triethylamine salt of the corresponding diacid) and 73.8 mol % of 4-chlorotetrahydrophthalic anhydride (as the triethylamine salt of the corresponding diacid).

[0045] The aqueous phase was extracted with 20 ml of toluene containing 3 wt% triethylamine in a separatory funnel at room temperature...

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PUM

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Abstract

A method for the synthesis of substituted phthalic anhydrides (IV) wherein R' is a halogen, aromatic or aliphatic group comprising 1-18 carbons, hydrogen or nitro group is the transimidation between a substituted N-alkyl phthalimide (V) wherein R is an alkyl having from 1 to 18 carbons, and a substituted tetrahydrophthalic anhydride (VI): The by product of this reaction, a substituted N-alkyl tetrahydrophthalimide (VII), may be converted by aromatization to the substituted N-alkyl phthalimide (V).

Description

[0001] Cross References to Related Applications [0002] none [0003] Statement Regarding Federally Funded Research and Development [0004] none Background of the invention [0005] The present invention relates to the preparation method of acid anhydride. More specifically, the present invention relates to a transimidation-based process for the preparation of anhydrides. [0006] Polyetherimide is a high heat-resistant engineering plastic with many uses. As disclosed in U.S. Patent No. 5,229,482, a route for the synthesis of polyetherimides proceeds via bis(4-chlorophthalimide) having the structure (I) [0007] [0008] wherein X is a divalent alkylene, cycloalkylene or arylene moiety. Bis(4-chlorophthalimide) (II) wherein X is 1,3-phenyl is particularly useful. [0009] [0010] Typically, bis(chlorophthalimide) (I) and (II ). [0011] [0012] 4-Chlorophthalic anhydride is an expensive raw material, which currently has to be synthesized on commission. Ex...

Claims

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Application Information

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IPC IPC(8): C07C51/54C07C63/16C07D307/89C07D209/48C07C51/06
CPCC07D209/48C07C51/06C07C63/68
Inventor 罗伊·R·奥德尔托马斯·L·古根海姆
Owner SABIC INNOVATIVE PLASTICS IP BV
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