IL199054A - Method of purifying beta-phenylethyl alcohol - Google Patents
Method of purifying beta-phenylethyl alcoholInfo
- Publication number
- IL199054A IL199054A IL199054A IL19905409A IL199054A IL 199054 A IL199054 A IL 199054A IL 199054 A IL199054 A IL 199054A IL 19905409 A IL19905409 A IL 19905409A IL 199054 A IL199054 A IL 199054A
- Authority
- IL
- Israel
- Prior art keywords
- tower
- phenylethyl alcohol
- liquid
- boiling point
- rectification tower
- Prior art date
Links
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 title claims description 87
- 238000000034 method Methods 0.000 title claims description 22
- 238000000605 extraction Methods 0.000 claims description 24
- 239000003513 alkali Substances 0.000 claims description 22
- 238000009835 boiling Methods 0.000 claims description 20
- 238000004821 distillation Methods 0.000 claims description 17
- 238000005406 washing Methods 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 13
- 238000000746 purification Methods 0.000 claims description 11
- 238000000622 liquid--liquid extraction Methods 0.000 claims description 10
- 238000000638 solvent extraction Methods 0.000 claims description 10
- 239000002304 perfume Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 229940067107 phenylethyl alcohol Drugs 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229940100595 phenylacetaldehyde Drugs 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000010692 aromatic oil Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- -1 for example Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/84—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by extractive distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
METHOD OF PURIFYING β-PHENYLETHYL ALCOHOL Sumitomo Chemical Company, Limited SPECIFICATION METHOD OF PURIFYING β-PHENYLETHYL ALCOHOL Technical Field The present invention relates to a method of purifying β-phenylethyl alcohol. More particularly, the present invention relates to a method of purifying β-phenylethyl alcohol, being characterized in that off-odor components produced in a purification tower can be selectively separated and removed from β-phenylethyl alcohol, to obtain high purity of β-phenylethyl alcohol having excellent aromatic odor for perfume, only by a simple operation and with good efficiency, without requiring complicated apparatuses and operations.
Background Art β-phenylethyl alcohol is a valuable substance which is used as a rose perfume widely in washing agents, cosmetics and the like, and in use thereof, products having high purity and excellent in aromatic odor are required. In general, when impurities performing an effect on the original aromatic odor are present even in trace amount in a perfume component, a product value lowers remarkably, thus, a method of purification thereof is particularly paid to attention, In particular, there is a problem that in a purification tower for purifying the final product, off-odor components, phenylacetaldehyde and styrene are produced by oxidation and dehydration reactions of β-phenylethyl alcohol at high temperatures, and mixed into the product. As - 1 - ' 2 19905472" catalysts for theee reactions, organic acids, alkal i ne ca talysis or example. 6od i um hydroxide), air a nd the li ke n re me nt ioned. As a method for purifying β-phenylethyl alcohol reported until now, a method is known for carrying out purification after separation of these cata lyst components by simple distillation in the upstream of a purification tower (Japanese Patent Application Laid pen (JP-A) No. 62-286939). However, these methods have defects and have problematic points as an industrial means. That is, in a simple distillation method, when the operation pressure of a purification tower is negative, there is no effect on suppression of an oxidation reactiou of β-phenylethyl alcohol due to air leaked in trace amount through a flange portion or the like of the apparatus. Further, a new distillation equipment in the upstream of a purification tower is required, leading also to an economical disadvantage.
Disclosure of the Invention Under such conditions, the present invention has an ohject. of providing a method of purifying β-phenylethyl alcohol, being characterized in that off odor components produced in a puriOcation tower can' be selectively separated a nd removed from β-phenylethyl alcohol, to obtain high purity β-phenylethyl alcohol having excellent aromatic odor for perfume, only by a simple operation and with good efficiency, without requiring complicated a ppa ratuses and operations.
That is, the present invention relates to a method of purifying 0-phenylethy] alcohol in which β-phenylethyl alcohol to be purified is fed to a rectification tower, to obiain β-phenylethyl alcohol purified as a side cut^ wherein the side cut position is 5 to 20% from the head of the rectification tower based on the total theoretical stage number.
Brief Explanation of Drawing Fig. 1 is a schematic view showing flow of the present invention. Description of Marks · 1. feeding tube (for crude β- henylethyl alcohol) 2. heavy component separating tower 3. drainage tube 4. drainage tube . alkali washing tank 6. feeding tube (for sodium hydroxide) 7. alkali discharge water 8. drainage tube 9. extraction distillation tower . drainage tube 11. feeding tube (for extraction solvent (A)) 12. liquid-liquid extraction tower 13. feeding tube (for extraction solvent (B)) 14. drainage tube . feeding tube 16. rectification tower 17. product 18. drainage tube 19. drainage tube Best Modes for Carrying Out the Invention β-phenylethyl alcohol to be purified in the present invention is not particularly restricted, and for example, those obtained via the following steps are mentioned.
Heavy component separating step: a step of separating heavy components from crude β-phenylethyl alcohol Alkali washing step: a 6tep of bringing the liquid separated from heavy components in the heavy component separating step into contact with an alkali aqueous solution Light boiling point component separating step: a step of subjecting the liquid obtained in the alkali washing step to extraction distillation and liquid-liquid extraction to separate light boiling point components, and feeding the liquid separated from the light boiling point components to the rectification tower The heavy component separating step is a step of separating heavy components from crude β-phenylethyl alcohol. As crude β-phenylethyl alcohol, those obtained from, for example, a method by hydrogen reduction of styrene oxide, a method by reaction of benzene and ethylene oxide, a method by hydrogen reduction of phenylacetic acid, a method by oxidation reaction of an aromatic hydrocarbon compound, and the like can be used.
The alkali washing step is a step of bringing the liquid separated from heavy components in the heavy component separating step into contact with an alkali aqueous solution. As the alkali aqueous solution, for example, ammonia water, sodium hydroxide water and the like can be used, and preferable from the standpoint of easiness of handling is a sodium hydroxide aqueous solution. The alkali concentration of the alkali aqueous solution is ' - usually about 1 to 50 wt%. For alkali washing, it may be advantageous, to be brief, that crude β-phenylethyl alcohol is mixed and contacted with an alkali aqueous solution, then, subjected to oil-water separation. The temperature in washing is usually room temperature (ca. 20*C) to 100°C, and the amount of the alkali aqueous solution to be used is 5 to 50 parts by weight with respect to 100 parts by weight of β-phenylethyl alcohol.
The light boiling point component separating step is a step of subjecting the liquid obtained in the alkali washing step to extraction distillation and liquid-liquid extraction to separate light boiling point components, and feeding the liquid separated from the light boiling point components to a rectification tower of the present invention. As the extraction solvent (A) used in extraction distillation, a mixed liquid of water and 1,2-propanediol can be used from the standpoint of efficiency of removal of light boiling point components. Regarding the mixing formulation of the mixed liquid, the weight ratio of water to 1,2-propanediol is preferably V9 to 7:3. Extraction distillation is carried out under conditions of reduced pressure, a temperature of 50 to 200" C and a reflux ratio of 0.1 to 50, and an extraction eolvent (A) of high volatility and low boiling point components flow from the tower head and β-phenylethyl alcohol separated from light boiling point components is drained from the tower bottom. In liquid-liquid extraction, light boiling point components contained in the extraction solvent (A) after use in extraction distillation are extracted with other extraction solvent (B). As the extraction solvent (B) used in liquid-liquid extraction, aromatic oils are preferably used. As the aromatic oil, for example, benzene, toluene and xylene are preferably mentioned. The extraction solvent (A) purified in liquid-liquid extraction is preferably re-ueed in extraction distillation from the standpoint of economical use of the solvent and reduction of cost for post-treatment of the used solvent.
The present invention has a maximum feature in which β-phenylethyl alcohol to be purified is fed to a rectification tower, and β-phenylethyl alcohol purified as a side cut is obtained utilizing a difference of boiling point between β-phenylethyl alcohol and off-odor components produced in the rectification tower. By this, the above-described problem to be solved by the present invention can be solved. That is, in the case of recovery of β-phenylethyl alcohol from the tower head of a rectification tower not by the present invention, removal of offodor components produced in the rectification tower is insufficient.
As the side cut position, any positions other than the rectification tower head can be adopted, however, it is advantageous to approximate the position to the tower bottom since the separation ratio of off-odor components produced in the rectification tower decreases at positions nearer to the tower head and increases at positions nearer to the tower bottom. In contrast, the separation ratio of off-odor components of high boiling point not produced in a rectification tower lowers at positions nearer to the tower bottom, thus, it is preferable that the side cut position is 5 to 20% from the head of the rectification tower based on the total theoretical stage number. As the rectification tower, there can be used distillation towers such as a porous plate tower, bubble tower, packed tower and the like usually used. The operation conditions of the rectification tower include usually a tower head pressure of 0 to 101.3 kPa (absolute pressure) and a tower bottom temperature of 100 to 250°C. Particularly, it is preferable that the tower head pressure is 0 to 50 kPa (absolute pressure) and the tower bottom temperature is 150 to 200°C and it is more preferable that the tower head pressure is 0.01 to 50 kPa (absolute pressure) from the standpoint of the specific volatility of the separated component and the temperature of heat 60urce of re 'boiler.
In the present invention, it is preferable that the fraction obtained from the head of a rectification column is recycled to the above -described light boiling point component separating step from the standpoint of capability of suppression of loss of β-phenylethyl alcohol in tower head components. The position for recycle can be any position in the light boiling point component separating step, and preferable is an extraction distillation tower feed line from the standpoint of extraction efficiency. p-phenylethyl alcohol obtained by the present invention is one from which off-odor components have been highly removed, and thus can be used optimally in a perfume component application.
EXAMPLES The present invention will be illustrated by examples below, Example 1 Crude β-phenylethyl alcohol having a content of P'phenylethyl alcohol of 67.1 wt°/o was fed at a rate of 425.4 kg/hr through a feeding tube (1) disposed at the 12-th stage counted from the tower head of a heavy component c separating tower (2) and a liquid from which heavy components had been separated by distillation was drained at a rate of 310.9 kg/hr through a drainage tube (4). The heavy component separating tower (2) had a stage number of 33, and a tower head pressure of 29.3 kPa and a reflux ratio of 3.9. Crude β-phenylethyl alcohol after the heavy component separating step was fed to an alkali washing tank (5), and simultaneously, an alkali water having a concentration of sodium hydroxide of 25 wt% was fed through a feeding tube (6) at a rate of 62.9 kg/hr to the alkali washing tank (5). The alkali washing tank (5) used a reactor equipped inside a rotation blade for improving washing efficiency and was operated at a temperature of 80°C under atmospheric pressure. Crude β-phenylethyl alcohol after the alkali washing step was fed at a rate of 302.9 kg/hr through a drainage tube (8) to the tower head portion of an extraction distillation tower (9), meanwhile, a mixed liquid of water and 1,2-propanediol (weigh ratio l'l) as an extraction solvent purified in a liquid-liquid extraction tower (12) was fed at a rate of 378.6 kg/hr through a feeding tube (11) disposed at the 50 th stage counted from the tower head. The extraction distillation tower (9) had a stage number of 62, and a tower head pressure of 18.7 kPa and a reflux ratio of 5.2. Light boiling point components were fed, together with water and 1,2-propanediol, to the tower head part of the liquid-liquid extraction tower (12) at a rate of 443.9 kg/hr through a drainage tube (10) from the tower head of the extraction distillation tower (9), and mixed in contact with toluene fed to the tower bottom part at a rate of 264.6 kg hr through a feeding tube (13), then, drained through a drainage tube (14). The liquid-liquid extraction tower (12) had a stage number of 100, and a tower head pressure of 437.8 kPa. Crude β-phenylethyl alcohol from which light boiling point components had been separated was fed from the tower bottom of the extraction distillation tower (9) at a rate of 267.6 kg/hr through a feeding tube (15) disposed at the 56-th stage counted from the tower head of a rectification tower (16). A product β-phenylethyl alcohol was purified at a rate of 208.3 kg/hr as a side cut from a drainage tube (17) disposed at the 6-th stage counted from the tower head of a product tower (16). Off-odor components produced in the rectification tower were recycled at a rate of 30 kg/hr to the extraction distillation tower (9) through a drainage tube (18). Here, the rectification tower had a stage number of 90, and a tower head pressure of 29.3 kPa, a tower bottom temperature of 195.5°C and a reflux ratio of 8.3. β-phenylethyl alcohol obtained here had a purity of 99.7 wt%, and had concentrations of phenylacetaldehyde and styrene produced in the rectification tower of 42 ppm by weight and 0.2 ppm by weight, respectively, thus, was a product manifesting no uncomfortable off odor and having a quality suitable for perfume application.
Comparative Example 1 β-phenylethyl alcohol was drained from the tower head of the rectification tower (16) under the same operation conditions of the respective steps excepting that in the rectification tower (16). β-phenylethyl alcohol obtained here showed mixing of phenylacetaldehyde and styrene produced in the rectification tower at concentrations of 212 ppm by weight and 37 ppm by weight, respectively, thus, was a product manifesting uncomfortable off odor and having a quality not suitable for perfume application.
Industrial Applicability 9 - · The present invention can provide a method of purifying β-phenylethyl alcohol, being characterized in that offodor components produced in a rectification tower can be selectively separated and removed from β-phenylethyl alcohol, to obtain high purity 3'phenylethyl alcohol having excellent aromatic odor for perfume, only by a simple operation and with good efficiency, without requiring complicated apparatuses and operations.
Claims (5)
1. A method of purifying β-phenylethyl alcohol, comprising feeding 6- phenylethyl alcohol to be purified to a rectification tower, to obtain β-phenylethyl alcohol purified as a side cut, wherein the side cut position is S to 20% from the head of the rectification tower based on the total theoretical stage number.
2. The purification method according to Claim 1 , wherein the operation conditions of the rectification tower include a tower head pressure of 0 to 101.3kPa (absolute pressure) and a tower bottom temperature of 100 to 250°C.
3. The purification method according to Claim 1 or 2, wherein the 6-phenylethyl alcohol to be purified is one which is obtained via the following steps: heavy component separating step: a step of separating heavy components from crude 6-phenylethyl alcohol, alkali washing step: a step of bringing the liquid separated from heavy components in the heavy component separating step into contact with an alkali aqueous solution, then, performing oil-water separation to obtain an oil layer, and light boiling point component separating step: as step of subjecting the liquid obtained in the alkali washing step to extraction distillation and liquid-liquid extraction to separate ligh boiling point components, and feeding the liquid separated from the light boiling point components to the rectification tower as described in claim 1.
4. The purification method according to Claim 3, wherein the fraction obtained from the tower head of the rectification tower is recycled to said light boiling point component separating step. 199054/4
5. β-phenylethyl alcohol, obtained by the purification method according to any one of Claims 1 to 4, for use in a perfume component. FOR THE" Djs€S¾¾fiak Hesf& Partners
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007008886A JP5003172B2 (en) | 2007-01-18 | 2007-01-18 | Purification method of β-phenylethyl alcohol |
| PCT/JP2008/050925 WO2008088074A1 (en) | 2007-01-18 | 2008-01-17 | METHOD FOR PURIFICATION OF β-PHENYLETHYL ALCOHOL |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL199054A true IL199054A (en) | 2012-06-28 |
Family
ID=39636069
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL199054A IL199054A (en) | 2007-01-18 | 2009-06-01 | Method of purifying beta-phenylethyl alcohol |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP5003172B2 (en) |
| CN (1) | CN101583584B (en) |
| IL (1) | IL199054A (en) |
| WO (1) | WO2008088074A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104529700A (en) * | 2014-12-05 | 2015-04-22 | 上海化工研究院 | Purification method for beta-phenylethyl alcohol prepared by bio-fermentation |
| JP7669674B2 (en) | 2020-12-01 | 2025-04-30 | 住友ベークライト株式会社 | Method for purifying cyclic compounds |
| CN117088756A (en) * | 2023-08-21 | 2023-11-21 | 万华化学集团股份有限公司 | A method for recovering 2-phenylethanol from heavy oil in styrene production process |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL190870C (en) * | 1979-10-16 | 1994-10-03 | Sumitomo Chemical Co | Method for purifying crude beta-phenethyl alcohol. |
| US4400558A (en) * | 1981-04-17 | 1983-08-23 | Atlantic Richfield Company | Recovery of 2-phenylethanol |
| JP3858512B2 (en) * | 1999-04-07 | 2006-12-13 | 住友化学株式会社 | Purification method of β-phenylethyl alcohol |
| SG82692A1 (en) * | 1999-04-07 | 2001-08-21 | Sumitomo Chemical Co | Method for purifying beta-phenylethyl alcohol |
| JP3846101B2 (en) * | 1999-04-08 | 2006-11-15 | 住友化学株式会社 | Purification method of β-phenylethyl alcohol |
| JP2004182848A (en) * | 2002-12-03 | 2004-07-02 | Sumitomo Chem Co Ltd | Method for adjusting benzyl alcohol content in phenethyl alcohol for flavoring |
-
2007
- 2007-01-18 JP JP2007008886A patent/JP5003172B2/en not_active Expired - Fee Related
-
2008
- 2008-01-17 CN CN2008800024263A patent/CN101583584B/en not_active Expired - Fee Related
- 2008-01-17 WO PCT/JP2008/050925 patent/WO2008088074A1/en not_active Ceased
-
2009
- 2009-06-01 IL IL199054A patent/IL199054A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008174482A (en) | 2008-07-31 |
| CN101583584B (en) | 2013-03-13 |
| JP5003172B2 (en) | 2012-08-15 |
| WO2008088074A1 (en) | 2008-07-24 |
| CN101583584A (en) | 2009-11-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |