CN106316990A - Method for recycling epoxycyclohexane and n-pentanol from light oil - Google Patents
Method for recycling epoxycyclohexane and n-pentanol from light oil Download PDFInfo
- Publication number
- CN106316990A CN106316990A CN201610695923.2A CN201610695923A CN106316990A CN 106316990 A CN106316990 A CN 106316990A CN 201610695923 A CN201610695923 A CN 201610695923A CN 106316990 A CN106316990 A CN 106316990A
- Authority
- CN
- China
- Prior art keywords
- oxa
- bicyclo
- amyl alcohol
- light oil
- recovery
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
-
- 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
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
-
- 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
-
- 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
- C07C29/88—Separation; Purification; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification of at least one compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/24—Synthesis of the oxirane ring by splitting off HAL—Y from compounds containing the radical HAL—C—C—OY
- C07D301/26—Y being hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method for recycling epoxycyclohexane and n-pentanol from light oil, comprising: acquiring light oil; mixing the light oil and an alkali, reacting at 0-50 DEG C for 0.5-5 hours to obtain a mixed liquid; rectifying the mixed liquid to obtain a light component containing epoxycyclohexane and n-pentanol and a heavy component containing hydroxyaldehyde condensate; subjecting the light component containing epoxycyclohexane and n-pentanol to separation and purification to obtain epoxycyclohexane and n-pentanol; in the above method, the light oil and the alkali are mixed, aldehyde impurities in the light oil such as hexanal and cyclopentanecarboxaldehyde are subjected to hydroxyaldehyde condensation reaction to generate high-boiling-point material, and the high-boiling-point material is rectified such that the content of hexanal and epoxycyclohexane is less than 0.5% and even less than 0.2%, the hexanal and cyclopentanecarboxaldehyde side reaction is under control, and the recycle rate and refining concentration of the cyclohexane and n-pentanol are further increased.
Description
Technical field
The present invention relates to chemical field, particularly relate to reclaim 7-oxa-bicyclo[4.1.0 and the method for n-amyl alcohol from light oil.
Background technology
During air oxidation of cyclohexane prepares Ketohexamethylene, generate principal product Ketohexamethylene and also have boiling point lower than it simultaneously
Plurality of impurities, account for the 1% of Ketohexamethylene total amount, be referred to as " light oil " in industry.Light oil component is more complicated, has twenty or thirty kind
Composition, main 7-oxa-bicyclo[4.1.0, the n-amyl alcohol of 25%, the raw material hexamethylene of remaining 5% and the product Ketohexamethylene of 15% containing about 40%,
Other component be Hexalin, cyclopentanol, 2-amylalcohol, butanol, hexanal, cyclopenta formaldehyde and toluene etc. (mainly boiling point 80 DEG C ~
Material between 165 DEG C).Whole nation Ketohexamethylene total amount about 3,000,000 tons at present, corresponding light oil is more than 20,000 tons, to group in light oil
Point content is high and added value is high 7-oxa-bicyclo[4.1.0 and n-amyl alcohol recycle, and have great economic and social benefit.
Traditional method reclaiming 7-oxa-bicyclo[4.1.0 and n-amyl alcohol from light oil has: first pass through after rectification " leaves out the beginning and the end "
Retain midbarrel (three sections of extractions will be divided by boiling point material between 80 DEG C ~ 165 DEG C, be divided into 80 DEG C ~ 127 DEG C, 128 DEG C ~
145 DEG C and 146 DEG C ~ 165 DEG C three fraction section), the major constituent of this middle boiling range 128 DEG C ~ 145 DEG C is 7-oxa-bicyclo[4.1.0 and positive penta
Alcohol (both sums about 85%), then go out the 7-oxa-bicyclo[4.1.0 of 99% and the n-amyl alcohol of 99% by chemical bond physics Methods For Purification.
Although said method achieves reclaims the fine chemical product such as 7-oxa-bicyclo[4.1.0 and n-amyl alcohol from light oil, but by
Containing the impurity such as hexanal and cyclopenta formaldehyde in the component that boiling range is 128 DEG C ~ 145 DEG C, contact with hydrochloric acid at 7-oxa-bicyclo[4.1.0
Ring-opening reaction in there is multiple side reaction, as n-amyl alcohol and 7-oxa-bicyclo[4.1.0 generation ring-opening reaction, hexanal occur with n-amyl alcohol
Aldolisation, cyclopenta formaldehyde and n-amyl alcohol generation aldolisation etc., cause 7-oxa-bicyclo[4.1.0 and n-amyl alcohol recovery yield and
Refined concentration all cannot improve further.
Therefore, find a kind of recovery 7-oxa-bicyclo[4.1.0 and method of n-amyl alcohol from light oil, make hexanal and cyclopenta first
Aldehyde side reaction is controlled, reclaims yield with raising 7-oxa-bicyclo[4.1.0 further and n-amyl alcohol and refined concentration becomes the heat that people study
Point.
Summary of the invention
Based on this, it is necessary to for the problem in background technology, it is provided that a kind of reclaim from light oil 7-oxa-bicyclo[4.1.0 and
The method of n-amyl alcohol, makes hexanal and cyclopenta formaldehyde side reaction controlled, to improve 7-oxa-bicyclo[4.1.0 and n-amyl alcohol recovery further
Yield and refined concentration.
A kind of recovery 7-oxa-bicyclo[4.1.0 and method of n-amyl alcohol from light oil, comprises the following steps:
Obtain light oil, containing 7-oxa-bicyclo[4.1.0, n-amyl alcohol, hexanal and cyclopenta formaldehyde in described light oil；
Described light oil and alkali are mixed, reacts 0.5 ~ 5 hour at 0 ~ 50 DEG C, obtain mixed liquor；
By described mixed liquor rectification, obtain containing 7-oxa-bicyclo[4.1.0 and the light component of n-amyl alcohol and the restructuring containing aldol condensate
Point；
The described light component containing 7-oxa-bicyclo[4.1.0 and n-amyl alcohol is carried out separating-purifying, obtains 7-oxa-bicyclo[4.1.0 and n-amyl alcohol.
Wherein in an embodiment, mix after the step of described acquisition light oil and by described light oil and alkali
Before step, further comprising the steps of:
Described light oil is carried out rectification, obtains the fraction that boiling range is 128 DEG C ~ 145 DEG C.
Wherein in an embodiment, the addition of described alkali is the 0.1% ~ 1% of described light oil quality.
Wherein in an embodiment, described alkali is sodium hydroxide, calcium hydroxide or potassium hydroxide.
Wherein in an embodiment, the described light component containing 7-oxa-bicyclo[4.1.0 and n-amyl alcohol is carried out separating-purifying,
Obtain the step of 7-oxa-bicyclo[4.1.0 and n-amyl alcohol particularly as follows:
Mix described containing 7-oxa-bicyclo[4.1.0 and the light component of n-amyl alcohol, hydrochloric acid and saline, carry out open loop at-20 DEG C ~ 130 DEG C
Reaction, obtains containing 2-chloro Hexalin and the oil water mixture of n-amyl alcohol；
The described oil water mixture containing 2-chloro Hexalin and n-amyl alcohol is carried out separating-purifying, respectively obtains 2-chloro hexamethylene
Alcohol and n-amyl alcohol；
Described 2-chloro Hexalin and liquid caustic soda are mixed, carries out ring-closure reaction at 90 DEG C ~ 130 DEG C, respectively obtain 7-oxa-bicyclo[4.1.0
And circulating brine；
Described for part circulating brine is used as after 20 DEG C ~ 80 DEG C flash distillations the saline needed for described ring-opening reaction.
Wherein in an embodiment, 7-oxa-bicyclo[4.1.0 and salt in the described light component containing 7-oxa-bicyclo[4.1.0 and n-amyl alcohol
In acid, the mol ratio of hydrogen chloride is 1:1.01 ~ 1:10.
Wherein in an embodiment, the concentration of described saline is 18% ~ 22%.
Wherein in an embodiment, described liquid caustic soda is aqueous sodium carbonate or sodium hydrate aqueous solution.
Wherein in an embodiment, the concentration of described circulating brine is 22% ~ 25%.
Wherein in an embodiment, described 2-chloro Hexalin is 1:1 ~ 1:1.1 with the mol ratio of alkali in liquid caustic soda.
Above-mentioned 7-oxa-bicyclo[4.1.0 and the method for n-amyl alcohol of reclaiming from light oil, first mixes light oil and alkali, makes lightweight
The aldehyde type impurities generation aldol reactions such as hexanal in oil and cyclopenta formaldehyde, generate high boiling substance, then by rectification, make
Obtaining in the light component containing 7-oxa-bicyclo[4.1.0 and n-amyl alcohol, the content of hexanal and cyclopenta formaldehyde is even less than less than 0.5%
0.2%, make hexanal and cyclopenta formaldehyde side reaction controlled, improve hexamethylene and the recovery yield of n-amyl alcohol further and refine dense
Degree.
Detailed description of the invention
Understandable for enabling the above-mentioned purpose of the present invention, feature and advantage to become apparent from, the concrete reality to the present invention below
The mode of executing is described in detail.Elaborate a lot of detail in the following description so that fully understanding the present invention.But
The present invention can implement to be much different from alternate manner described here, and those skilled in the art can be without prejudice to this
Doing similar improvement in the case of bright intension, therefore the present invention is not limited by following public being embodied as.
A kind of recovery 7-oxa-bicyclo[4.1.0 and method of n-amyl alcohol from light oil, comprises the following steps:
S110, acquisition light oil.
Wherein, containing 7-oxa-bicyclo[4.1.0, n-amyl alcohol, hexanal and cyclopenta formaldehyde in light oil.
S120, above-mentioned light oil and alkali are mixed, react 0.5 ~ 5 hour at 0 ~ 50 DEG C, obtain mixed liquor.
Wherein, the addition of alkali is the 0.1% ~ 1% of light oil quality.
Preferably, alkali is sodium hydroxide, calcium hydroxide or potassium hydroxide.
The aldehyde type impurities generation aldol reactions such as hexanal in light oil, cyclopenta formaldehyde, generate high boiling substance.
Preferably, after step S110 and before step S120, above-mentioned from light oil, reclaim 7-oxa-bicyclo[4.1.0 and just
The method of amylalcohol is further comprising the steps of:
Light oil is carried out rectification, obtains the fraction that boiling range is 128 DEG C ~ 145 DEG C.
S130, by above-mentioned mixed liquor rectification, obtain contracting containing 7-oxa-bicyclo[4.1.0 and the light component of n-amyl alcohol with containing aldol
The heavy constituent of compound.
In the light component containing 7-oxa-bicyclo[4.1.0 and n-amyl alcohol that above-mentioned mixed liquor rectification is obtained, hexanal and cyclopenta first
The content of aldehyde is even less than 0.2% less than 0.5%.
S140, the above-mentioned light component containing 7-oxa-bicyclo[4.1.0 and n-amyl alcohol is carried out separating-purifying, obtain 7-oxa-bicyclo[4.1.0
And n-amyl alcohol.
Concrete, the above-mentioned light component containing 7-oxa-bicyclo[4.1.0 and n-amyl alcohol is carried out separating-purifying, obtains epoxy hexamethylene
The step of alkane and n-amyl alcohol comprises the following steps:
S1401, by above-mentioned containing 7-oxa-bicyclo[4.1.0 and the light component of n-amyl alcohol, hydrochloric acid and saline mixing, enter at-20 DEG C ~ 130 DEG C
Row ring-opening reaction, respectively obtains containing 2-chloro Hexalin and the oil water mixture of n-amyl alcohol.
Concrete, the hydrogen chloride in 7-oxa-bicyclo[4.1.0 and hydrochloric acid in the above-mentioned light component containing 7-oxa-bicyclo[4.1.0 and n-amyl alcohol
Carry out ring-opening reaction at-20 DEG C ~ 130 DEG C, obtain 2-chloro Hexalin.
Owing to containing certain water yield in hydrochloric acid, easily there is hydrolytic side reactions in 7-oxa-bicyclo[4.1.0.Add finite concentration saline
Can effectively suppress hydrolysis.
In the present embodiment, brine strength is 18% ~ 22%.
7-oxa-bicyclo[4.1.0 and the mol ratio of hydrogen chloride in hydrochloric acid in the above-mentioned light component containing 7-oxa-bicyclo[4.1.0 and n-amyl alcohol
For 1:1.01 ~ 1:10.
By 7-oxa-bicyclo[4.1.0 and hcl reaction being generated the 2-chloro Hexalin of higher (＞ 200 DEG C), pass through
It can be separated by rectification with the n-amyl alcohol of relatively low boiling (138 DEG C), thus reclaims n-amyl alcohol.
S1402, the above-mentioned oil water mixture containing 2-chloro Hexalin and n-amyl alcohol is carried out separating-purifying, respectively obtain
2-chloro Hexalin and n-amyl alcohol.
Wherein, the method for separating-purifying is particularly as follows: will carry out containing the oil water mixture of 2-chloro Hexalin and n-amyl alcohol
Oil-water separation, obtains aqueous phase and containing 2-chloro Hexalin and the oil phase of n-amyl alcohol；By above-mentioned containing 2-chloro Hexalin and just
The oil phase of amylalcohol carries out rectification and purification, respectively obtains 2-chloro Hexalin and n-amyl alcohol, aqueous phase outer venting wastewater treatment equipment.
S1403, above-mentioned 2-chloro Hexalin and liquid caustic soda are mixed, carry out ring-closure reaction at 90 DEG C ~ 130 DEG C, respectively obtain
7-oxa-bicyclo[4.1.0 and circulating brine.
Wherein, liquid caustic soda is aqueous sodium carbonate or sodium hydrate aqueous solution.In 2-chloro Hexalin and liquid caustic soda alkali mole
Ratio is 1:1 ~ 1:1.1.
Concrete, the alkali in 2-chloro Hexalin and liquid caustic soda carries out ring-closure reaction at 90 DEG C ~ 130 DEG C, respectively obtains epoxy
Hexamethylene and circulating brine.
In the present embodiment, the concentration of circulating brine is 22% ~ 25%.
S1404, above-mentioned for part circulating brine is used as after 20 DEG C ~ 80 DEG C flash distillations the saline needed for above-mentioned ring-opening reaction.
Owing to step S1401 ~ S1404 is a continuous process, the concentration of the circulating brine that ring-closure reaction obtains can be increasingly
Height, if fully recovering, certainly will cause brine system concentration to rise, and therefore uses the mode of part reuse, makes ring-opening reaction institute
The brine strength needed maintains 18% ~ 22% all the time, process stabilizing.
It is appreciated that the method by the above-mentioned light component containing 7-oxa-bicyclo[4.1.0 and n-amyl alcohol carries out separating-purifying is not limited to
Step S1401 described above ~ S1404, in other embodiments, it is also possible to the method using other separating-purifyings, only
Want 7-oxa-bicyclo[4.1.0 and n-amyl alcohol to be respectively obtained to reclaim.
Above-mentioned 7-oxa-bicyclo[4.1.0 and the method for n-amyl alcohol of reclaiming from light oil, first mixes light oil and alkali, makes lightweight
The aldehyde type impurities generation aldol reactions such as hexanal in oil and cyclopenta formaldehyde, generate high boiling substance, then by rectification, make
Obtaining in the light component containing 7-oxa-bicyclo[4.1.0 and n-amyl alcohol, the content of hexanal and cyclopenta formaldehyde is even less than less than 0.5%
0.2%, make hexanal and cyclopenta formaldehyde side reaction controlled, improve hexamethylene and the recovery yield of n-amyl alcohol further and refine dense
Degree.
Embodiment described above only have expressed the several embodiments of the present invention, and it describes more concrete and detailed, but also
Therefore the restriction to the scope of the claims of the present invention can not be interpreted as.It should be pointed out that, for those of ordinary skill in the art
For, without departing from the inventive concept of the premise, it is also possible to make some deformation and improvement, these broadly fall into the guarantor of the present invention
Protect scope.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.
Claims (10)
1. one kind is reclaimed 7-oxa-bicyclo[4.1.0 and the method for n-amyl alcohol from light oil, it is characterised in that comprise the following steps:
Obtain light oil, containing 7-oxa-bicyclo[4.1.0, n-amyl alcohol, hexanal and cyclopenta formaldehyde in described light oil；
Described light oil and alkali are mixed, reacts 0.5 ~ 5 hour at 0 ~ 50 DEG C, obtain mixed liquor；
By described mixed liquor rectification, obtain containing 7-oxa-bicyclo[4.1.0 and the light component of n-amyl alcohol and the restructuring containing aldol condensate
Point；
The described light component containing 7-oxa-bicyclo[4.1.0 and n-amyl alcohol is carried out separating-purifying, obtains 7-oxa-bicyclo[4.1.0 and n-amyl alcohol.
Recovery 7-oxa-bicyclo[4.1.0 and the method for n-amyl alcohol from light oil the most according to claim 1, it is characterised in that institute
After stating the step of acquisition light oil and by further comprising the steps of before the step of described light oil and alkali mixing:
Described light oil is carried out rectification, obtains the fraction that boiling range is 128 DEG C ~ 145 DEG C.
Recovery 7-oxa-bicyclo[4.1.0 and the method for n-amyl alcohol from light oil the most according to claim 1 and 2, its feature exists
In, the addition of described alkali is the 0.1% ~ 1% of described light oil quality.
Recovery 7-oxa-bicyclo[4.1.0 and the method for n-amyl alcohol from light oil the most according to claim 1 and 2, its feature exists
In, described alkali is sodium hydroxide, calcium hydroxide or potassium hydroxide.
Recovery 7-oxa-bicyclo[4.1.0 and the method for n-amyl alcohol from light oil the most according to claim 1 and 2, its feature exists
In, the described light component containing epoxy hexamethylene and n-amyl alcohol is carried out separating-purifying, obtains the step of 7-oxa-bicyclo[4.1.0 and n-amyl alcohol
Rapid particularly as follows:
Mix described containing 7-oxa-bicyclo[4.1.0 and the light component of n-amyl alcohol, hydrochloric acid and saline, carry out open loop at-20 DEG C ~ 130 DEG C
Reaction, obtains containing 2-chloro Hexalin and the oil water mixture of n-amyl alcohol；
The described oil water mixture containing 2-chloro Hexalin and n-amyl alcohol is carried out separating-purifying, respectively obtains 2-chloro hexamethylene
Alcohol and n-amyl alcohol；
Described 2-chloro Hexalin and liquid caustic soda are mixed, carries out ring-closure reaction at 90 DEG C ~ 130 DEG C, respectively obtain 7-oxa-bicyclo[4.1.0
And circulating brine；
Described for part circulating brine is used as after 20 DEG C ~ 80 DEG C flash distillations the saline needed for described ring-opening reaction.
Recovery 7-oxa-bicyclo[4.1.0 and the method for n-amyl alcohol from light oil the most according to claim 5, it is characterised in that institute
Stating 7-oxa-bicyclo[4.1.0 in the light component containing 7-oxa-bicyclo[4.1.0 and n-amyl alcohol is 1:1.01 ~ 1 with the mol ratio of hydrogen chloride in hydrochloric acid:
10。
Recovery 7-oxa-bicyclo[4.1.0 and the method for n-amyl alcohol from light oil the most according to claim 6, it is characterised in that institute
The concentration stating saline is 18% ~ 22%.
Recovery 7-oxa-bicyclo[4.1.0 and the method for n-amyl alcohol from light oil the most according to claim 6, it is characterised in that institute
Stating liquid caustic soda is aqueous sodium carbonate or sodium hydrate aqueous solution.
Recovery 7-oxa-bicyclo[4.1.0 and the method for n-amyl alcohol from light oil the most according to claim 6, it is characterised in that institute
The concentration stating circulating brine is 22% ~ 25%.
Recovery 7-oxa-bicyclo[4.1.0 and the method for n-amyl alcohol from light oil the most according to claim 6, it is characterised in that
Described 2-chloro Hexalin is 1:1 ~ 1:1.1 with the mol ratio of alkali in liquid caustic soda.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610695923.2A CN106316990A (en) | 2016-08-22 | 2016-08-22 | Method for recycling epoxycyclohexane and n-pentanol from light oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610695923.2A CN106316990A (en) | 2016-08-22 | 2016-08-22 | Method for recycling epoxycyclohexane and n-pentanol from light oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106316990A true CN106316990A (en) | 2017-01-11 |
Family
ID=57743435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610695923.2A Pending CN106316990A (en) | 2016-08-22 | 2016-08-22 | Method for recycling epoxycyclohexane and n-pentanol from light oil |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106316990A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106977372A (en) * | 2017-04-18 | 2017-07-25 | 上海五伦化工科技有限公司 | A kind of preparation method of secondary alcohol |
| CN113816928A (en) * | 2021-10-29 | 2021-12-21 | 岳阳昌德环境科技有限公司 | Clean production method for recovering and purifying cyclohexene oxide from oxidized light oil |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101225077A (en) * | 2007-12-14 | 2008-07-23 | 岳阳昌德化工实业有限公司 | Novel ring-opening reaction method for process of recovering cyclohexene oxide from light oil |
| CN103130751A (en) * | 2011-11-29 | 2013-06-05 | 中国石油化学工业开发股份有限公司 | Method for separating cyclohexene oxide and n-amyl alcohol |
-
2016
- 2016-08-22 CN CN201610695923.2A patent/CN106316990A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101225077A (en) * | 2007-12-14 | 2008-07-23 | 岳阳昌德化工实业有限公司 | Novel ring-opening reaction method for process of recovering cyclohexene oxide from light oil |
| CN103130751A (en) * | 2011-11-29 | 2013-06-05 | 中国石油化学工业开发股份有限公司 | Method for separating cyclohexene oxide and n-amyl alcohol |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106977372A (en) * | 2017-04-18 | 2017-07-25 | 上海五伦化工科技有限公司 | A kind of preparation method of secondary alcohol |
| CN113816928A (en) * | 2021-10-29 | 2021-12-21 | 岳阳昌德环境科技有限公司 | Clean production method for recovering and purifying cyclohexene oxide from oxidized light oil |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104892666B (en) | A kind of preparation method of high-purity phosphoric acid tributyl | |
| CN104926690B (en) | The recovery process for purification and device of acetonitrile in a kind of synthesis for Ceftriaxone Sodium | |
| CN106396163A (en) | Method for comprehensive treatment and recycling of ammonium sulfate wastewater of rare-earth smelting | |
| CN106316990A (en) | Method for recycling epoxycyclohexane and n-pentanol from light oil | |
| CN109607623B (en) | Simplified utilization process of titanium white waste acid | |
| RU2708204C1 (en) | Method of producing potassium sulphate from potassium chloride and sulfuric acid | |
| JP2017109993A (en) | Method for producing dichloropropanol | |
| CN1745913A (en) | Recovering treatment of hydrated hydrazine by-product saline-alkali by urea method | |
| CN105947984A (en) | Production process for recycling and producing anhydrous hydrogen fluoride from high-concentration wastewater containing fluoride | |
| CN110950736B (en) | Process for preparing alcohol substance by hydrolyzing metal organic product | |
| CN104557517A (en) | Comprehensive treatment process for waste sodium citrate mother solution | |
| CN114436883B (en) | Method for recovering N, N-dimethylacetamide from multi-element solution system | |
| CN114249704B (en) | Preparation method of alkylene oxide | |
| CN111848453B (en) | Production process and production line of 4-methyl-2' -cyanobiphenyl | |
| CN106892479A (en) | A kind of method that oxalic acid and hydrochloric acid are reclaimed in the waste water from rare earth oxalate precipitate | |
| CN101613311B (en) | System and method for reclaiming hexanolactam from rearrangement mixture | |
| CN106316895B (en) | A kind of resource utilization method of H soda acids liquation | |
| CN113861007A (en) | Method for treating distillation residue of 2-chloro-6-fluorobenzaldehyde | |
| CN107188785B (en) | Resource utilization method of 2, 4-diaminobenzene sulfonic acid and salt production wastewater | |
| CN106316992A (en) | Method and apparatus for recycling epoxycyclohexane and n-pentanol from light oil | |
| CN112898113A (en) | Method for recycling polyolefin catalyst waste liquid | |
| CN110921630A (en) | Method for preparing hydrogen chloride by resolving hydrochloric acid | |
| CN116063150B (en) | Method for recycling chloroethane and solvent thereof in production of alpha-ethylfuranmethanol | |
| CN104630877B (en) | Method for preparing calcium sulfate dihydrate whisker from tin smelting waste residues | |
| EP2769970B1 (en) | Process for purifying hydrocarbons |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| TA01 | Transfer of patent application right | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20190307 Address after: 414000 Room 209, 111 Yingpanling Road, Yueyang Economic and Technological Development Zone, Yueyang City, Hunan Province (office only) Applicant after: Yueyang Changde Environmental Technology Co., Ltd. Address before: 414000 Department of Caprolactam Business, Wangyue Road, Yueyang City, Hunan Province 618 Applicant before: Changde Chemical Industry Co., Ltd., Yueyang |
|
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170111 |