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Reduction of the viscosity of reactive heavy byproducts during the production of 1,3-propanediol

A propylene glycol and reactive technology, applied in the preparation of heterocyclic compounds, hydroxyl compounds, organic compounds, etc., can solve the problem of low combination formation rate

Inactive Publication Date: 2008-08-06
SHELL INT RES MAATSCHAPPIJ BV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At 110°C and 1000 psig of 2:1 mole syngas, a selectivity as high as 47 mole % was achieved, but the combined formation rate of PDO and 3-hydroxypropanal was rather low at 0.05-0.07 moles per liter per hour

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] To 50 g of PDO plant bottom product 1751B (containing reactive heavies; sodium content 1.55% by weight) was added 30 g of Dowex 50WX4-100, which is a strongly acidic ion exchange resin, 50-100 mesh, and the mixture was stirred over the weekend under a nitrogen protective gas. A sample of the supernatant showed a sodium content of <0.005% by weight.

[0024] The liquid fraction (24286-13-3) was recovered by filtration, and the filtrate was divided into 10 gram portions.

[0025] A 10 gram portion of the filtrate was treated with a solution of 0.27 grams of sodium hydroxide (NaOH) in distilled water (2.5 grams) and the fresh mixture was rotary evaporated under vacuum (1-Torr - 0.133 kPa) at 40°C. The remaining 5cc of red liquid (24286-15-2) was judged to be very viscous.

[0026] A second 10 gram portion of the filtrate was treated with a solution of 0.22 grams of potassium hydroxide (KOH) in distilled water (2.5 grams), then also rotovaped at 1 Torr (0.133 kPa) and 40...

Embodiment 2

[0028] According to the process of Example 1, with 120 grams of Dowex 200 grams of PDO distillation bottoms 1751B were treated with 50WX4-100 resin and the mixture was stirred under a nitrogen blanket to produce a supernatant containing <0.005% by weight sodium. The resin was removed by filtration and the filtrate (24286-19-1) was divided into 60 gram portions.

[0029] A 60 gram portion of the filtrate was treated with a solution of 1.62 grams of sodium hydroxide in water (4.5 grams) and the fresh mixture was spun evaporated at 1 Torr (0.133 kPa) and 40°C. The remaining reddish liquid (24286-19-2) was found to have 5686mm at 40°C 2 / s kinematic viscosity.

[0030]A second 60 gram portion of the filtrate was treated with 1.32 g of KOH in water (4.5 g) and the mixture was evaporated at 1 Torr (0.133 kPa) and 40°C. The remaining red liquid (24286-19-3) was found to have 54mm at 40°C 2 / s kinematic viscosity.

Embodiment 3

[0032] According to the process of Examples 1 and 2, with 120 grams of Dowex 200 grams of PDO distillation bottoms 1751B were treated with 50WX4-100 resin to remove all sodium ions, and the resin was removed by filtration. The new filtrate is #24286-21-1.

[0033] A 60 gram portion of the filtrate was treated with 2.64 grams of KOH dissolved in water (3.0 grams) and the mixture was evaporated at 1 Torr (0.133 kPa) and 40°C. Residual red liquid (24286-21-2) has 43mm at 40°C 2 / s kinematic viscosity.

[0034] A second 60 gram portion was treated with 0.66 g of KOH dissolved in water (1.5 g) and the mixture was evaporated. The red liquid (24286-21-3) remaining here has 42mm at 40°C 2 / s kinematic viscosity.

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PUM

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Abstract

The present invention is an improvement upon the process for the production of 1,3-propanediol wherein an aqueous solution of 3-hydroxy propanal is formed, catalyst, if any, used in said formation is removed from the solution, sodium hydroxide is added to the solution to neutralize any acid therein such that the pH is at least 5, the neutralized aqueous solution is subjected to hydrogenation to produce a crude 1,3-propanediol mixture which is distilled to produce 1,3-propanediol, water, and reactive heavy components. The improvement on this process comprises replacing the sodium hydroxide with a hydroxide selected from the group consisting of ammonium hydroxide, alkali metal hydroxides other than sodium hydroxide, and alkaline earth metal hydroxides to reduce the viscosity of the reactive heavy components.

Description

technical field [0001] The present invention relates to a process for the preparation of 1,3-propanediol (PDO), wherein an aqueous solution of 3-hydroxypropanal is formed, the catalyst used in the formation is removed from the solution, and hydroxide is added to the solution to neutralize it any acid, and hydrogenating the neutralized aqueous solution to produce a PDO mixture, which is distilled to produce purified PDO. Background technique [0002] Several companies have developed the technology to prepare PDO starting from ethylene oxide as the main raw material. Ethylene oxide is reacted with synthesis gas, a mixture of carbon monoxide and hydrogen, obtained by steam reforming of natural gas or partial oxidation of hydrocarbons. The idealized reaction of ethylene oxide (EO) with syngas to produce PDO is shown below: [0003] EO+CO+2H 2 →PDO [0004] US Patents US 4,873,378, US 4,873,379 and US 5,053,562 to Hoechst Celanese describe a single step reaction using 2:1 (mo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/14C07C31/20C07C29/141C07C45/58
CPCC07C45/58C07C29/141C07C31/205C07C29/94
Inventor T·G·詹姆斯G·C·康普林E·L·尼尔森J·F·尼夫汤J·B·鲍威尔P·R·韦德尔
Owner SHELL INT RES MAATSCHAPPIJ BV