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Process for producing glycolic acid from formaldehyde and hydrogen cyanide

A technology of glycolic acid and hydrogen cyanide, applied in chemical instruments and methods, cyanide reaction preparation, organic compound preparation, etc., can solve the problem of no nitrilase activity, etc.

Active Publication Date: 2008-02-27
THE CHEMOURS CO FC LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Brevibacterium R312 is known to have nitrile hydratase and amidase activities, but no nitrilase activity (Toumeix et al., Antonie van Leeuwenhoek, 52:173-182 (1986))

Method used

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  • Process for producing glycolic acid from formaldehyde and hydrogen cyanide
  • Process for producing glycolic acid from formaldehyde and hydrogen cyanide
  • Process for producing glycolic acid from formaldehyde and hydrogen cyanide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0342] Preheat 90% formaldehyde continuous feed

[0343] About 10.18 g of 52 wt% aqueous formaldehyde (<1% methanol, DuPont) was mixed with 12.81 g of water and the raw meal was heated to about 76°C for about 40 min until the mixture became a clear homogeneous liquid solution. The solution was cooled to room temperature, still a homogeneous liquid. Then, 0.16 mL of 16.7 wt% NaOH aqueous solution was added to the formaldehyde solution. 1.56 g of the as-synthesized solution (23 wt% formaldehyde) was placed in the autoclave and the remainder was used for continuous formaldehyde feed.

[0344] The reaction vessel equipped with stirring was placed in an oil bath maintained at 55°C. An approximately 12-inch section formaldehyde feed line (1 / 16" OD (approximately 1.6 mm) x 0.040" ID (approximately 1.02 mm)) placed directly before the reaction flask inlet was heated to 120°C, then heated for approximately 2.0 hours. The following reactants are each continuously pumped into the re...

Embodiment 2

[0350] Preheating 100% formaldehyde continuous feed

[0351] About 10.18 g of 52 wt% aqueous formaldehyde (<1% methanol, E.I. DuPont de Nemours) was mixed with 12.81 g of water and the raw meal was heated to about 76°C for about 40 min until the mixture became a clear homogeneous liquid solution. The solution was cooled to room temperature, still a homogeneous liquid. Then, 0.14 mL of 16.7 wt% NaOH aqueous solution was added to the formaldehyde solution. The resulting solution (23 wt% formaldehyde) was used for continuous formaldehyde feed.

[0352] A reaction vessel equipped with stirring was charged with a mixture of 0.18 g HCN in 3.4 g water and then placed in an oil bath maintained at 55°C. An approximately 12-inch section formaldehyde feed line (1 / 16" OD x 0.040" ID) placed directly before the reaction flask inlet was heated to 120°C, and the following reactants were each continuously pumped over a period of approximately 2.0 hours Into the reactor:

[0353] 4.41 mL...

Embodiment 3

[0358] Preheating 100% formaldehyde continuous feed

[0359] Approximately 14.20 g of 37 wt% formaldehyde in water (10-15% methanol, Acros Organics, Morris Plains, NJ) was mixed with 8.78 g of water and 0.14 mL of 16.7 wt% NaOH solution. The resulting solution (23 wt% formaldehyde) was used for continuous formaldehyde feed.

[0360] A reaction vessel equipped with stirring was charged with a mixture of 0.18 g HCN in 3.4 g water and then placed in an oil bath maintained at 55°C. An approximately 12-inch section formaldehyde feed line (1 / 16" OD x 0.040" ID) placed directly before the reaction flask inlet was heated to 120°C, and the following reactants were each continuously pumped over a period of approximately 2.0 hours Into the reactor:

[0361] 4.21 mL / hr of 50 wt% HCN in water (d=0.86 g / mL)

[0362] 7.67 mL / hr of 23 wt% aqueous formaldehyde, as described above (d = 1.07 g / mL).

[0363] After about 2.0 hours, the feeds were stopped, the autoclave was removed from the o...

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Abstract

A process is provided for producing glycolic acid from formaldehyde and hydrogen cyanide. More specifically, heat-treated formaldehyde and hydrogen cyanide are reacted to produce glycolonitrile having low concentrations of impurities. The glycolonitrile is subsequently converted to an aqueous solution of ammonium glycolate using an enzyme catalyst having nitrilase activity derived from Acidovorax facilis 72W (ATCC 57746). Glycolic acid is recovered in the form of the acid or salt from the aqueous ammonium glycolate solution using a variety of methods described herein.

Description

[0001] This application claims the benefit of US Provisional Application Nos. 60 / 638,168; 60 / 638,148; 60 / 638,176; 60 / 638,127; field of invention [0002] The invention relates to the fields of organic acid synthesis, molecular biology and microbiology. More specifically, a method for producing glycolic acid from formaldehyde and hydrogen cyanide using an enzyme catalyst having nitrilase activity is provided. Background of the invention [0003] Glycolic acid (HOCH 2 COOH; CAS Registry No. 79-14-1) is the simplest member of the alpha-hydroxy acid family of carboxylic acids. Its properties make it ideal for a wide range of consumer and industrial uses, including in water well restoration, the leather industry, the oil and gas industry, the laundry and textile industries, as a monomer in the preparation of polyglycolic acid (PGA), and as an ingredient in personal care products . Glycolic acid is also a major ingredient in cleaners in several industries (dairy and food proces...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/42C07C227/26
CPCC12P7/42
Inventor R·迪科西莫T·福M·S·佩恩A·帕诺瓦D·P·奥基夫J·S·汤普森F·G·加拉赫尔X·李
Owner THE CHEMOURS CO FC LLC
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