CN1295068A - Dealcoholizing and refining method for epoxy cyclohexane recovered from cyclohexane oxide as side product - Google Patents
Dealcoholizing and refining method for epoxy cyclohexane recovered from cyclohexane oxide as side product Download PDFInfo
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- CN1295068A CN1295068A CN 99115635 CN99115635A CN1295068A CN 1295068 A CN1295068 A CN 1295068A CN 99115635 CN99115635 CN 99115635 CN 99115635 A CN99115635 A CN 99115635A CN 1295068 A CN1295068 A CN 1295068A
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Abstract
The method of the present invention features that in the condition of certain temperature and the presence of 0.3-1% alkali catalyst alcohol impurities in epoxy cyclohexane to be refined are subjected to addition reaction with epoxy cyclohexane to produce high boiling point dialkyloxy-cyclohexane, and the epoxy cyclohexane is further rectified to obtain pure epoxy cyclohexane product with 99 % oven purity and containing no alcohol impurity essentially.
Description
The present invention relates to a kind of alcohols impurity of tasting product by the epoxy hexamethylene that reclaims in the cyclohexane oxidation by product that removes, thereby epoxy hexane content in the product is increased to method more than 98% by 90-95%.
Produce in pimelinketone, the hexalin technology at cyclohexane oxidation, the a certain amount of lightweight oil of while by-product, wherein epoxy cyclohexane content is the 10-40% of lightweight oil total amount, presses the method that Chinese patent CN-1180702A introduces, and recyclable content is the epoxy cyclohexane product of 90-95%.By analysis, research, we have confirmed that the impurity in this product is mainly C
5Alcohols impurity accounts for about 80% of total impurities.
The content of the present invention's research is to adopt simple process, removes the C in the former epoxy cyclohexane product
5Alcohols impurity is increased to epoxy cyclohexane content in the product more than 98%.
Domestic do not have as yet at present produce the report of content at the high purity epoxy cyclohexane product more than 98.And abroad, normally be starting raw material with the tetrahydrobenzene.Through hydrolysis and oxidation, epoxidation processes is produced high-purity epoxy cyclohexane.Japanese Patent JP5130060 has introduced the different methods that reclaims epoxy cyclohexane from the cyclohexane oxidation by product respectively with JP509528, but the recovery epoxy cyclohexane product purity of its report only is respectively 81% and 94.7%.
The object of the present invention is to provide and a kind ofly produce the method for purity greater than 99% epoxy cyclohexane product by the cyclohexane oxidation byproduct.
The present invention is achieved in that the method for introducing by CN-1180702A earlier, makes content and be 90～95% thick epoxy cyclohexane product.Then:
(1). thoroughly remove the trace water in the thick epoxy cyclohexane product;
(2). carry out addition reaction under the following conditions: basic catalyst (sodium hydroxide or potassium hydroxide) add-on is 0.3%～1% (wt) of material total amount; Temperature of reaction: 130～135 ℃ (during normal pressure), 150～160 ℃ (during pressurization); Reaction times: 3 hours (under the normal pressure), 0.5～1 hour (during pressurization); The material steam that reaction process produces by condenser condenses after total reflux return reactor.
(3). after reaction finishes, cooling reaction solution to 50～80 ℃, then mechanically as filter or chemistry in and mode remove basic catalyst.
(4). take continuously or the batch fractionating mode, control reflux ratio 1～3: 1 is collected 129～132 ℃ of fractions during atmospheric distillation; (0.066mpa vacuum tightness) collects 95～100 ℃ of fractions during decompression.Can obtain content greater than 98% epoxy cyclohexane product.
Embodiment (1). get the thick epoxy cyclohexane 700g that removes minor amount of water, through gas Chromatographic Determination, sample contains epoxy cyclohexane 90.1%, C
5Alcohols impurity is: Pentyl alcohol 5.5%, cyclopentanol 3.1% add above-mentioned raw materials and 3.5g sodium hydroxide in the 1000ml there-necked flask.The described processing condition of by specification: under normal pressure and 133～134 ℃ of conditions, total reflux reaction 3 hours, reaction solution is through cooling post neutralization sodium hydroxide, again through being interrupted rectifying, collect 129～132 ℃ of fraction 567.7g, through gas Chromatographic Determination, epoxy cyclohexane content is 99.1% in the product, and its epoxy cyclohexane total recovery is 89.2%.
Embodiment (2). get and embodiment (1) same materials 700g, in the 1000ml2.0mpa autoclave, add 3g potassium hydroxide.The described processing condition of by specification, under 0.4mpa pressure and 155 ± 1 ℃ of conditions, reacted 45 minutes, reaction solution is after cooling, mechanical filter is removed catalyzer, adopt then and be interrupted the rectifying mode, and under reduced pressure (0.066mpa vacuum tightness), collect 95～100 ℃ of fractions, obtain product 562.5g, through gas Chromatographic Determination, epoxy cyclohexane content is 99.2% in the product, and the epoxy cyclohexane total recovery is 88.4%.
Claims (5)
1, a kind of epoxy cyclohexane product dealcoholysis of reclaiming from cyclohexane oxidation by product method of re-refining mainly is made of addition catalyzed reaction and two parts of conventional distillation, it is characterized in that:
1). (epoxy cyclohexane content is 90～95% to epoxy cyclohexane product that will be to be re-refined, alcohols impurity 4～8%) at normal pressure～0.5mpa, temperature of reaction is 130～160 ℃, and under 0.3%～1.0% (wt) basic catalyst (as sodium hydroxide or potassium hydroxide) existence condition, stirring reaction 0.5～3 hour.Reaction solution after filtration or the neutralization, to remove basic catalyst;
2). adopt continuously or interruption rectifying, control of reflux ratio is 1～2: 1, collect 129～132 ℃ of fractions; Or be decompressed to 0.066mpa vacuum tightness, and control of reflux ratio is 1～3: 1, collect 95～100 ℃ of fractions, and obtain epoxy cyclohexane content greater than 98% product.
2, method according to claim 1 is characterized in that: addition reaction neutral and alkali catalyzer optimal addn is 0.4%～0.6 (wt) of material total amount.
3, method according to claim 1 is characterized in that: the optimal reaction temperature in the normal pressure addition reaction is 133 ± 1 ℃, and the optimal reaction temperature in the 0.4mpa compressive reaction is 155 ± 1 ℃.
4, method according to claim 1 is characterized in that: after reaction finishes, adopt filter or in and mode remove catalysts.
5, method according to claim 1 is characterized in that: during atmospheric distillation, cutting top temperature is that 129～132 ℃ fraction section is high-purity epoxy cyclohexane product of re-refining; When rectification under vacuum (0.066mpa vacuum tightness), pushing up cutting prod fraction between warm 95～100 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 99115635 CN1295068A (en) | 1999-11-08 | 1999-11-08 | Dealcoholizing and refining method for epoxy cyclohexane recovered from cyclohexane oxide as side product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 99115635 CN1295068A (en) | 1999-11-08 | 1999-11-08 | Dealcoholizing and refining method for epoxy cyclohexane recovered from cyclohexane oxide as side product |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1295068A true CN1295068A (en) | 2001-05-16 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 99115635 Pending CN1295068A (en) | 1999-11-08 | 1999-11-08 | Dealcoholizing and refining method for epoxy cyclohexane recovered from cyclohexane oxide as side product |
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| CN (1) | CN1295068A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103003255A (en) * | 2010-07-14 | 2013-03-27 | 陶氏环球技术有限责任公司 | Process and assembly for producing alkylene oxides and glycol ethers |
| CN103508982A (en) * | 2012-06-21 | 2014-01-15 | 中国石油化工股份有限公司 | Method for separation recovery of cyclohexene oxide from cyclohexanone by-product light oil |
| 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 |
-
1999
- 1999-11-08 CN CN 99115635 patent/CN1295068A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103003255A (en) * | 2010-07-14 | 2013-03-27 | 陶氏环球技术有限责任公司 | Process and assembly for producing alkylene oxides and glycol ethers |
| US9169226B2 (en) | 2010-07-14 | 2015-10-27 | Dow Global Technologies Llc | Process and assembly for producing alkylene oxides and glycol ethers |
| US9273019B2 (en) | 2010-07-14 | 2016-03-01 | Dow Global Technologies Llc | Process and assembly for producing alkylene oxides and glycol ethers |
| CN103003255B (en) * | 2010-07-14 | 2016-10-05 | 陶氏环球技术有限责任公司 | For producing method and the complete set of equipments of alkylene oxide and glycol ethers |
| US9822087B2 (en) | 2010-07-14 | 2017-11-21 | Dow Global Technologies Llc | Assembly for producing alkylene oxides and glycol ethers |
| CN103508982A (en) * | 2012-06-21 | 2014-01-15 | 中国石油化工股份有限公司 | Method for separation recovery of cyclohexene oxide from cyclohexanone by-product light oil |
| 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 |
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| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
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