CA2247991A1 - Process for preparing 1,6 hexane diol with a level of purity over 99 % - Google Patents
Process for preparing 1,6 hexane diol with a level of purity over 99 %Info
- Publication number
- CA2247991A1 CA2247991A1 CA002247991A CA2247991A CA2247991A1 CA 2247991 A1 CA2247991 A1 CA 2247991A1 CA 002247991 A CA002247991 A CA 002247991A CA 2247991 A CA2247991 A CA 2247991A CA 2247991 A1 CA2247991 A1 CA 2247991A1
- Authority
- CA
- Canada
- Prior art keywords
- mixture
- cyclohexane
- hexane diol
- distillation stage
- cyclohexane diols
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical class OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 238000004821 distillation Methods 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000003809 water extraction Methods 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a process for the preparation of 1,6 hexane diol from a carboxylic acid mixture containing adipic acid, 6-hydroxy caproic acid and, in small quantities, 1,4 cyclohexane diols. Said mixture is obtained as a by-product of the oxidation of cyclohexane into cyclohexanone/ cyclohexanol by water extraction of the reaction mixture. Said process involves esterification of the acids and hydrogenation. According to this process (a) the monocarboxylic acids and the dicarboxylic acids contained in the aqueous dicarboxylic acid mixture are reacted with a low-molecular alcohol to form the corresponding carboxylic acid esters; (b) the excess alcohol and low-boiling agents of the resultant esterification mixture are released in a first distillation stage; (c) separating into an ester fraction substantially free of 1,4 cyclohexane diols and a fraction containing at least the greater part of the 1,4 cyclohexane diols is carried out from the bottom product in a second distillation stage; (d) the ester fraction substantially free of 1,4 cyclohexane diols is catalytically hydrogenated; and (e) in a pure distillation stage 1,6 hexane diol is extracted from the hydrogenated discharge in a known manner.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1996107955 DE19607955A1 (en) | 1996-03-01 | 1996-03-01 | Economical production of pure 1,6-hexane-diol from by-product of oxidation of cyclohexane |
| DE19607955.1 | 1996-03-01 | ||
| DE19647348.9 | 1996-11-15 | ||
| DE1996147348 DE19647348A1 (en) | 1996-11-15 | 1996-11-15 | Economical production of pure 1,6-hexane-diol from by-product of oxidation of cyclohexane |
| PCT/EP1997/000980 WO1997031882A1 (en) | 1996-03-01 | 1997-02-28 | Process for preparing 1,6 hexane diol with a level of purity over 99 % |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2247991A1 true CA2247991A1 (en) | 1997-09-04 |
| CA2247991C CA2247991C (en) | 2006-06-27 |
Family
ID=36647292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002247991A Expired - Fee Related CA2247991C (en) | 1996-03-01 | 1997-02-28 | Process for preparing 1,6 hexane diol with a level of purity over 99 % |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2247991C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107337579A (en) * | 2017-08-29 | 2017-11-10 | 华陆工程科技有限责任公司 | A kind of method of serialization circulation liquid-phase hydrogenatin production hexylene glycol |
| CN113683483A (en) * | 2021-06-07 | 2021-11-23 | 浙江博聚新材料有限公司 | Production method and device of high-purity 1, 6-hexanediol |
-
1997
- 1997-02-28 CA CA002247991A patent/CA2247991C/en not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107337579A (en) * | 2017-08-29 | 2017-11-10 | 华陆工程科技有限责任公司 | A kind of method of serialization circulation liquid-phase hydrogenatin production hexylene glycol |
| CN107337579B (en) * | 2017-08-29 | 2024-04-12 | 华陆工程科技有限责任公司 | Method for producing hexanediol by continuous circulating liquid phase hydrogenation |
| CN113683483A (en) * | 2021-06-07 | 2021-11-23 | 浙江博聚新材料有限公司 | Production method and device of high-purity 1, 6-hexanediol |
| US11492316B1 (en) | 2021-06-07 | 2022-11-08 | Zhejiang Boju New Materials Co., Ltd. | Production method and production device of high-purity 1,6-hexanediol |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2247991C (en) | 2006-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130228 |