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Method of producing 1,5-pentanediol and/or 1,6-hexanediol

A manufacturing method and technology of hexylene glycol, applied in 1 field to achieve the effect of controlling deterioration

Inactive Publication Date: 2010-03-24
UBE IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no record about the acid value (AV value) or about the suspension bed catalyst

Method used

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  • Method of producing 1,5-pentanediol and/or 1,6-hexanediol
  • Method of producing 1,5-pentanediol and/or 1,6-hexanediol
  • Method of producing 1,5-pentanediol and/or 1,6-hexanediol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Step 1: Oxidation of Cyclohexane and Extraction with Water

[0094] Cyclohexane was oxidized at 160° C. and 1 MPa, and extracted with water at 160° C. and 1 MPa to obtain a carboxylic acid mixture having the following composition.

[0095]

[0096] Valeric acid: 0.2%

[0097] Caproic acid: 0.03%

[0098] Succinic acid: 0.2%

[0099] 6-Hydroxycaproic acid: 5.5%

[0100] Glutaric acid: 0.7%

[0101] Adipic acid: 4.5%

[0102] water (H 2 O): 78.3%

[0103] Other: 10.57%

[0104] Step 2: Concentration of water extract

[0105] Next, this extract was concentrated under the condition of 13KPa to obtain a concentrate with the following composition.

[0106] 6-Hydroxycaproic acid: 28.66%

[0107] Adipic acid: 23.80%

[0108] h 2 O: 2.0%

[0109] Step 3: Esterification

[0110] 700 g / h of the tower bottom liquid (the above-mentioned concentrate) and 700 g / h of methanol obtained in step 2 were continuously supplied to a reaction tank (gas-liquid reaction tan...

Embodiment 2

[0143] Part of the bottom liquid obtained in Step 4 and Step 6 of Example 1 was purified by distillation under the following conditions, and a fraction containing methyl adipate and methyl 6-hydroxyhexanoate as main components was obtained from the top of the tower . The acid value at this time was 0.1 mgKOH / g.

[0144] Distillation unit: sulzer labopacking (27 units)

[0145] Distillation conditions: 5 Torr, 105°C at the top of the tower, 190°C at the bottom of the tower

[0146] The pre-reduction of the catalyst in step 8 was performed in the same manner except that the above-mentioned purified methyl ester was used as a solvent, and the subsequent hydrogenation reaction was carried out in the same manner as in step 9. The results at this time are shown in Table 1. In addition, Table 5 shows the results of measuring the crystallite size of copper (0) in this catalyst by XRD.

Embodiment 3

[0152] Process A: Oxidation of cyclohexane and extraction with water

[0153] Cyclohexane was oxidized at 160° C. and 1 MPa, and extracted with water at 160° C. and 1 MPa to obtain a carboxylic acid mixture having the following composition.

[0154]

[0155] Valeric acid: 0.2%

[0156] Caproic acid: 0.03%

[0157] Succinic acid: 0.2%

[0158] 6-Hydroxycaproic acid: 5.5%

[0159] Glutaric acid: 0.7%

[0160] Adipic acid: 4.5%

[0161] water (H 2 O): 78.3%

[0162] Other: 10.57%

[0163] Step B: Concentration of water extract

[0164] Next, this extract was concentrated under the condition of 13KPa to obtain a concentrate with the following composition.

[0165] 6-Hydroxycaproic acid: 28.66%

[0166] Adipic acid: 23.80%

[0167] h 2 O: 2.0%

[0168] Process C: Esterification process

[0169] 500 g of the above-mentioned concentrate and 500 g of the filtrate of the hydrogenation reaction solution in step 9 of Example 1 were placed in a 1 L flask, and the tempe...

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Abstract

An objective is to provide a process for preparing 1,5-pentanediol and / or 1,6-hexanediol comprising esterifying, with an alcohol such as methanol, ethanol, butanol, or 1,6-hexanediol, a mixture of carboxylic acids such as glutaric acid, adipic acid and 6-hydroxycaproic acid which are a by-product in preparation of cyclohexanone by oxidation of cyclohexane with oxygen or an oxygen-containing gas; and hydrogenating the resulting esterified product in the presence of a copper-containing catalyst, which process is an industrially suitable process for preparing 1,5-pentanediol and / or 1,6-hexanediolin a high yield while controlling deterioration of the catalyst. The above objective is achieved by hydrogenating the esterified product with a catalyst obtained by prereducing a copper-containing catalyst in an alcohol having an acid value (AV) of 0.5 mg KOH / g or less or an ester having an acid value (AV) of 0.5 mg KOH / g or less.

Description

technical field [0001] The present invention relates to a kind of manufacture method of 1,5-pentanediol and / or 1,6-hexanediol, more particularly, relate to a kind of 1,5-pentanediol and / or A method for producing 1,6-hexanediol. Background technique [0002] As a method for producing 1,6-hexanediol, it is known to oxidize cyclohexane to generate carboxylic acid compounds such as adipic acid and hydroxycaproic acid as described in Patent Document 1, and to dissolve the carboxylic acid compound with ethanol, A method of producing 1,6-hexanediol by esterifying alcohols such as butanol and 1,6-hexanediol, and hydrogenating the resulting esterified product in the presence of a catalyst. In addition, in this production method, 1,5-pentanediol can be co-produced. [0003] In the above-mentioned production method of 1,6-hexanediol, when the esterified product having a high acid value (AV value) is hydrogenated, the catalyst deteriorates and the conversion rate of 1,6-hexanediol dec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/149
CPCB01J23/72B01J23/80B01J35/006C07C67/08C07C29/149B01J37/18B01J35/393B01J2235/15C07C31/20C07C69/44C07C69/42C07C69/675
Inventor 井伊宏文蔵藤敏雄河村嘉树
Owner UBE IND LTD