CN107445796B - Method for co-producing dimethyl benzyl alcohol and 1, 2-pentanediol - Google Patents
Method for co-producing dimethyl benzyl alcohol and 1, 2-pentanediol Download PDFInfo
- Publication number
- CN107445796B CN107445796B CN201710722825.8A CN201710722825A CN107445796B CN 107445796 B CN107445796 B CN 107445796B CN 201710722825 A CN201710722825 A CN 201710722825A CN 107445796 B CN107445796 B CN 107445796B
- Authority
- CN
- China
- Prior art keywords
- pentanediol
- reaction
- cumene hydroperoxide
- dimethyl benzyl
- benzyl alcohol
- 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.)
- Active
Links
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
- C07C29/09—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
- C07C29/106—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 of oxiranes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
-
- 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)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The application provides a method for coproducing dimethylbenzyl alcohol and 1, 2-pentanediol, which comprises the following steps: carrying out epoxidation reaction on 1-pentene and cumene hydroperoxide under the action of an epoxidation catalyst to obtain a reaction solution containing 1, 2-cyclopentane epoxide and dimethyl benzyl alcohol; separating the reaction liquid to obtain 1, 2-epoxy pentane and dimethyl benzyl alcohol; carrying out hydrolysis reaction on 1, 2-epoxypentane and water under the action of a hydrolysis catalyst, and rectifying to obtain the 1, 2-pentanediol. The method for co-producing the dimethyl benzyl alcohol and the 1, 2-pentanediol takes the 1-pentene and the cumene hydroperoxide as raw materials to co-produce the dimethyl benzyl alcohol and the 1, 2-pentanediol, the process is simple, the synthesis cost is low, no wastewater is generated in the synthesis process, the selectivity of the dimethyl benzyl alcohol is over 90 percent, and the selectivity of the 1, 2-pentanediol is over 80 percent.
Description
Technical Field
The invention relates to the field of chemical industry, in particular to a method for co-producing dimethyl benzyl alcohol and 1, 2-pentanediol.
Background
The 1, 2-pentanediol is an important fine chemical product and has wide application. More than about 80% of 1, 2-pentanediol is used in the production of propiconazole globally, and more than 90% of 1, 2-pentanediol is used in the production of propiconazole domestically. In addition, the 1, 2-pentanediol is used as an excellent humectant, an antibacterial agent and a solubilizer, and can effectively improve the hydrolysis resistance of the sunscreen product. The research shows that the 1, 2-pentanediol can reduce the particle size of the emulsion, is beneficial to the stability of the emulsion, can reduce the sticky feeling caused by adding a polymer in the formula, is beneficial to forming the formula with finer appearance, and is suitable for a plurality of cosmetics. In addition, due to the use of multiple purification steps in the production process of the 1, 2-pentanediol, the 1, 2-pentanediol does not contain ethylene oxide, peroxide and unsaturated short-chain fatty acid with potential irritation, and is a really effective multifunctional skin and hair care product raw material.
The traditional synthesis methods of 1, 2-pentanediol mainly comprise a Grignard method, a peroxyacid method and a furfural hydrogenation method. The grignard process suffers from the high price of magnesium metal and produces a large amount of inorganic salts as by-products. The peroxyacid method does not need to use a catalyst, the process flow is simpler, but the process produces sodium formate with low added value as a byproduct, the yield of the whole process is lower, the price of the amylene is too high, the cost is high, and the influence is greatly limited by the byproduct. The furfural hydrogenation method is theoretically the shortest route and the lowest price of raw materials, and the synthesized product has high naturalness and is very popular in the field of daily chemicals, but the coproducts are very many, the hydrogen pressure is higher, and the safety of the synthesis process is lower.
At present, in the industry, the dimethyl benzyl alcohol is mainly prepared by the reduction reaction of cumene hydroperoxide and sodium sulfite, a large amount of sodium sulfate aqueous solution is generated as a byproduct in the reaction process, the atom economic benefit is poor, the wastewater is difficult to treat, and the product concentration is influenced in the crystallization process of the dimethyl benzyl alcohol.
Therefore, it is urgent to find a method for co-producing dimethylbenzyl alcohol and 1, 2-pentanediol, which has the advantages of simple process, low synthesis cost, high product selectivity and no waste water generation.
Disclosure of Invention
Accordingly, there is a need to provide a method for co-producing dimethylbenzyl alcohol and 1, 2-pentanediol, which has the advantages of simple process, low synthesis cost, high product selectivity and no waste water generation, in order to solve the problems in the background art.
A method for coproducing dimethylbenzyl alcohol and 1, 2-pentanediol, comprising the steps of:
carrying out epoxidation reaction on 1-pentene and cumene hydroperoxide under the action of an epoxidation catalyst to obtain a reaction solution containing 1, 2-cyclopentane epoxide and dimethyl benzyl alcohol;
separating the reaction liquid to obtain 1, 2-epoxy pentane and dimethyl benzyl alcohol;
and (3) carrying out hydrolysis reaction on the 1, 2-epoxypentane and water under the action of a hydrolysis catalyst, and rectifying to obtain the 1, 2-pentanediol.
In one embodiment, the 1-pentene is prepared by the following process:
and (3) carrying out dehydration reaction on the 1-pentene under the action of a dehydration catalyst to obtain the 1-pentene.
In one embodiment, the epoxidation catalyst is a salt compound of a transition metal, the transition metal is molybdenum, tungsten, vanadium or titanium, and the salt compound is naphthenate, 2-ethyl hexanoate or acetylacetone.
In one embodiment, the hydrolysis catalyst is a lewis acid.
In one embodiment, the dehydration catalyst is concentrated sulfuric acid, alumina, super-strong solid acid, or heteropoly acid.
In one embodiment, the molar ratio of the 1-pentene to the cumene hydroperoxide is 1-40: 1, and the epoxidation reaction is carried out under the following reaction conditions: the temperature is 20-200 ℃.
In one embodiment, the cumene hydroperoxide is pure cumene hydroperoxide or cumene hydroperoxide containing an organic solvent selected from at least one of cumene, toluene, ethylbenzene and xylene.
In one embodiment, the molar ratio of the water to the 1, 2-epoxypentane is 0.1-30: 1.
In one embodiment, the reaction conditions of the hydrolysis reaction are: the temperature is-50 ℃ to 150 ℃.
In one embodiment, the reaction conditions of the dehydration reaction are: the temperature is 200-400 ℃.
The method for co-producing the dimethyl benzyl alcohol and the 1, 2-pentanediol takes the 1-pentene and the cumene hydroperoxide as raw materials to co-produce the dimethyl benzyl alcohol and the 1, 2-pentanediol, the process is simple, the synthesis cost is low, no wastewater is generated in the synthesis process, the selectivity of the dimethyl benzyl alcohol is over 90 percent, and the selectivity of the 1, 2-pentanediol is over 80 percent.
Detailed Description
The present invention will be described in detail with reference to the following embodiments in order to make the aforementioned objects, features and advantages of the invention more comprehensible. In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein, but rather should be construed as broadly as the present invention is capable of modification in various respects, all without departing from the spirit and scope of the present invention.
A method for coproducing dimethylbenzyl alcohol and 1, 2-pentanediol, comprising the steps of:
s110, carrying out dehydration reaction on the 1-pentanol under the action of a dehydration catalyst to obtain the 1-pentene.
Wherein the dehydration catalyst is 98% concentrated sulfuric acid, alumina, super-strong solid acid or heteropoly acid.
The reaction conditions of the dehydration reaction are as follows: the temperature is 200-400 ℃.
Preferably, the reaction conditions of the dehydration reaction are: the temperature is 290-330 ℃.
It is understood that in other embodiments, the 1-pentene may be prepared by other methods, as long as the 1-pentene is obtained.
S120, carrying out epoxidation reaction on the 1-pentene and cumene hydroperoxide under the action of an epoxidation catalyst to obtain a reaction solution containing the 1, 2-cyclopentane epoxide and dimethyl benzyl alcohol.
Wherein the molar ratio of the 1-pentene to the cumene hydroperoxide is 1-40: 1. Preferably, the molar ratio of 1-pentene to cumene hydroperoxide is 4 to 10: 1.
The epoxidation catalyst is a salt compound of transition metal, the transition metal is molybdenum (Mo), tungsten (W), vanadium (V) or titanium (Ti), and the salt compound is naphthenate, 2-ethyl hexanoate or acetylacetone salt.
Preferably, the epoxidation catalyst is a molybdenum salt of 2-ethylhexanoic acid or a molybdenum salt of acetylacetone.
The reaction conditions for the epoxidation reaction were: the temperature is 20-200 ℃.
Preferably, the reaction conditions of the epoxidation reaction are: the temperature is 80-130 ℃.
The cumene hydroperoxide is either pure cumene hydroperoxide or cumene hydroperoxide containing an organic solvent.
When the cumene hydroperoxide is cumene hydroperoxide containing an organic solvent, the organic solvent is at least one selected from the group consisting of cumene, toluene, ethylbenzene and xylene.
S130, separating the reaction liquid to obtain the 1, 2-epoxy pentane and dimethyl benzyl alcohol.
Specifically, the method for separating the reaction solution comprises the following steps: rectifying the reaction liquid, collecting fractions at 85-95 ℃ to obtain 12-epoxypentane, and collecting fractions at 200-205 ℃ to obtain dimethylbenzyl alcohol.
S140, carrying out hydrolysis reaction on the 1, 2-epoxypentane and water under the action of a hydrolysis catalyst, and rectifying to obtain the 1, 2-pentanediol.
Wherein the molar ratio of the water to the 1, 2-epoxypentane is 0.1-30: 1. Preferably, the molar ratio of the water to the 1, 2-epoxypentane is 1-10: 1.
The hydrolysis catalyst is a lewis acid.
The reaction conditions of the hydrolysis reaction are as follows: the temperature is-50 ℃ to 150 ℃.
Preferably, the reaction conditions of the hydrolysis reaction are: the temperature is 0-70 ℃.
The method for co-producing the dimethyl benzyl alcohol and the 1, 2-pentanediol takes the 1-pentene and the cumene hydroperoxide as raw materials to co-produce the dimethyl benzyl alcohol and the 1, 2-pentanediol, the process is simple, the synthesis cost is low, no wastewater is generated in the synthesis process, the selectivity of the dimethyl benzyl alcohol is over 90 percent, and the selectivity of the 1, 2-pentanediol is over 80 percent.
The following are specific examples.
Example 1
Epoxidation reaction is carried out on a cumene solution of 1-pentene and 60% cumene hydroperoxide (the molar ratio of 1-pentene to cumene hydroperoxide is 2: 1) under the action of molybdenum salt of 2-ethyl hexanoic acid at 90 ℃ to obtain a reaction solution containing 1, 2-cyclopentane epoxide and dimethyl benzyl alcohol. And rectifying the reaction liquid to respectively obtain 1, 2-epoxy pentane and dimethyl benzyl alcohol.
Carrying out hydrolysis reaction on 1, 2-epoxypentane and water at the molar ratio of 1:10 at-10 ℃ under the action of boron trifluoride, and rectifying to obtain 1, 2-pentanediol.
The conversion rate of cumene hydroperoxide was calculated to be 99.0%, the selectivity of 1, 2-pentanediol was calculated to be 86.3%, and the selectivity of dimethylbenzyl alcohol was calculated to be 90.6%.
Example 2
Epoxidation reaction is carried out on a cumene solution of 1-pentene and 60% cumene hydroperoxide (the molar ratio of 1-pentene to cumene hydroperoxide is 6: 1) under the action of 2-ethylhexylate tungsten salt at 110 ℃, so as to obtain a reaction liquid containing 1, 2-cyclopentane epoxide and dimethyl benzyl alcohol. And rectifying the reaction liquid to respectively obtain 1, 2-epoxy pentane and dimethyl benzyl alcohol.
Carrying out hydrolysis reaction on 1, 2-epoxypentane and water in a molar ratio of 1:5 at 30 ℃ under the action of boron trifluoride, and rectifying to obtain 1, 2-pentanediol.
The conversion of cumene hydroperoxide was calculated to be 99.5%, the selectivity to 1, 2-pentanediol was calculated to be 83.3%, and the selectivity to dimethylbenzyl alcohol was calculated to be 94.3%.
Example 3
Epoxidation reaction is carried out on a cumene solution of 1-pentene and 50% cumene hydroperoxide (the molar ratio of 1-pentene to cumene hydroperoxide is 10: 1) at 130 ℃ under the action of acetylacetone molybdenum salt to obtain a reaction solution containing 1, 2-cyclopentane epoxide and dimethylbenzyl alcohol. And rectifying the reaction liquid to respectively obtain 1, 2-epoxy pentane and dimethyl benzyl alcohol.
Carrying out hydrolysis reaction on 1, 2-epoxy pentane and water in a molar ratio of 1:20 at 100 ℃ under the action of fluoboric acid, and rectifying to obtain the 1, 2-pentanediol.
The conversion rate of cumene hydroperoxide was calculated to be 99.9%, the selectivity of 1, 2-pentanediol was calculated to be 89.5%, and the selectivity of dimethylbenzyl alcohol was calculated to be 97.8%.
Example 4
Epoxidation reaction is carried out on a toluene solution of 1-pentene and 50% cumene hydroperoxide (the molar ratio of 1-pentene to cumene hydroperoxide is 10: 1) under the action of acetylacetone molybdenum salt at 130 ℃ to obtain a reaction liquid containing 1, 2-cyclopentane epoxide and dimethylbenzyl alcohol. And rectifying the reaction liquid to respectively obtain 1, 2-epoxy pentane and dimethyl benzyl alcohol.
Carrying out hydrolysis reaction on 1, 2-epoxy pentane and water with a molar ratio of 1:20 at 50 ℃ under the action of fluoboric acid, and rectifying to obtain 1, 2-pentanediol.
The conversion of cumene hydroperoxide was calculated to be 99.0%, the selectivity to 1, 2-pentanediol was calculated to be 83.4%, and the selectivity to dimethylbenzyl alcohol was calculated to be 95.2%.
Example 5
Epoxidation reaction is carried out on 1-pentene and 50% cumene hydroperoxide xylene solution (the molar ratio of 1-pentene to cumene hydroperoxide is 10: 1) under the action of acetylacetone molybdenum salt at 130 ℃, and reaction liquid containing 1, 2-cyclopentane epoxide and dimethyl benzyl alcohol is obtained. And rectifying the reaction liquid to respectively obtain 1, 2-epoxy pentane and dimethyl benzyl alcohol.
Carrying out hydrolysis reaction on 1, 2-epoxy pentane and water with a molar ratio of 1:20 at 50 ℃ under the action of fluoboric acid, and rectifying to obtain 1, 2-pentanediol.
The conversion of cumene hydroperoxide was calculated to be 98.7%, the selectivity to 1, 2-pentanediol was calculated to be 84.6%, and the selectivity to dimethylbenzyl alcohol was calculated to be 96.8%.
Example 6
Epoxidation reaction is carried out on 1-pentene and cumene hydroperoxide with the molar ratio of 10:1 under the action of acetylacetone molybdenum salt at 120 ℃ to obtain reaction liquid containing 1, 2-cyclopentane epoxide and dimethyl benzyl alcohol. And rectifying the reaction liquid to respectively obtain 1, 2-epoxy pentane and dimethyl benzyl alcohol.
Carrying out hydrolysis reaction on 1, 2-epoxy pentane and water in a molar ratio of 15:1 at 60 ℃ under the action of fluoboric acid, and rectifying to obtain the 1, 2-pentanediol.
The conversion of cumene hydroperoxide was calculated to be 97.9%, the selectivity to 1, 2-pentanediol was calculated to be 82.6%, and the selectivity to dimethylbenzyl alcohol was calculated to be 93.3%.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (9)
1. A method for coproducing dimethylbenzyl alcohol and 1, 2-pentanediol is characterized by comprising the following steps:
carrying out epoxidation reaction on 1-pentene and cumene hydroperoxide under the action of an epoxidation catalyst to obtain reaction liquid containing 1, 2-cyclopentane epoxide and dimethyl benzyl alcohol, wherein the epoxidation catalyst is a salt compound of transition metal, the transition metal is molybdenum and tungsten, and the salt compound is 2-ethyl hexanoate or acetylacetone salt;
separating the reaction liquid to obtain 1, 2-epoxy pentane and dimethyl benzyl alcohol;
and (3) carrying out hydrolysis reaction on the 1, 2-epoxypentane under the action of a hydrolysis catalyst, and rectifying to obtain the 1, 2-pentanediol.
2. The method of claim 1 for co-producing dimethylbenzyl alcohol and 1, 2-pentanediol, wherein the 1-pentene is prepared by:
and (3) carrying out dehydration reaction on the 1-pentanol under the action of a dehydration catalyst to obtain the 1-pentene.
3. The method for co-producing dimethylbenzyl alcohol and 1, 2-pentanediol of claim 1, wherein the hydrolysis catalyst is a lewis acid.
4. The method of claim 2, wherein the dehydration catalyst is 98% concentrated sulfuric acid, alumina, super strong solid acid or heteropoly acid.
5. The method for co-producing dimethylbenzyl alcohol and 1, 2-pentanediol according to claim 1, wherein the molar ratio of 1-pentene to cumene hydroperoxide is 1-40: 1, and the epoxidation reaction is performed under the following reaction conditions: the temperature is 20-200 ℃.
6. The method for co-producing dimethylbenzyl alcohol and 1, 2-pentanediol as claimed in claim 1, wherein the cumene hydroperoxide is pure cumene hydroperoxide or cumene hydroperoxide containing an organic solvent selected from at least one of cumene, toluene, ethylbenzene and xylene.
7. The method for co-producing dimethylbenzyl alcohol and 1, 2-pentanediol as claimed in claim 1, wherein the molar ratio of the water to the 1, 2-cyclopentane oxide is 0.1-30: 1.
8. The method for co-producing dimethylbenzyl alcohol and 1, 2-pentanediol as claimed in claim 1, wherein the reaction conditions of the hydrolysis reaction are: the temperature is-50 ℃ to 150 ℃.
9. The method for co-producing dimethylbenzyl alcohol and 1, 2-pentanediol as claimed in claim 2, wherein the reaction conditions of the dehydration reaction are: the temperature is 200-400 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710722825.8A CN107445796B (en) | 2017-08-22 | 2017-08-22 | Method for co-producing dimethyl benzyl alcohol and 1, 2-pentanediol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710722825.8A CN107445796B (en) | 2017-08-22 | 2017-08-22 | Method for co-producing dimethyl benzyl alcohol and 1, 2-pentanediol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107445796A CN107445796A (en) | 2017-12-08 |
| CN107445796B true CN107445796B (en) | 2020-07-28 |
Family
ID=60492957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710722825.8A Active CN107445796B (en) | 2017-08-22 | 2017-08-22 | Method for co-producing dimethyl benzyl alcohol and 1, 2-pentanediol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107445796B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108002977B (en) * | 2018-01-15 | 2020-12-04 | 台州泰捷化工科技有限公司 | Method for coproducing chemical products dimethylbenzyl alcohol and 1, 2-pentanediol |
| CN108129259B (en) * | 2018-01-15 | 2019-12-24 | 南京黛丽雅科技有限公司 | Catalyst and method for preparing chemical product 1, 2-pentanediol by catalysis of catalyst |
| CN110283046A (en) * | 2019-07-31 | 2019-09-27 | 新乡市巨晶化工有限责任公司 | A kind of preparation method of 1,2- pentanediol |
| CN110698436B (en) * | 2019-11-05 | 2021-01-26 | 北京水木滨华科技有限公司 | Synthetic method of aliphatic epoxy compound |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102010293A (en) * | 2010-11-02 | 2011-04-13 | 云南大学 | Method for catalyzing and synthesizing 1, 2-pentanediol by using titanium silicalite |
| CN102295625A (en) * | 2010-06-24 | 2011-12-28 | 中国石油化工股份有限公司 | Method for producing 1,2-epoxy cyclohexane and alpha, alpha-dimethyl benzyl alcohol |
| CN103539762A (en) * | 2012-07-12 | 2014-01-29 | 中国石油化工股份有限公司 | Method for producing epoxypropane by propylene epoxidation |
| CN106831309A (en) * | 2015-12-03 | 2017-06-13 | 中国石油化工股份有限公司 | The method that n-amyl alcohol is dehydrated n-pentene processed |
-
2017
- 2017-08-22 CN CN201710722825.8A patent/CN107445796B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102295625A (en) * | 2010-06-24 | 2011-12-28 | 中国石油化工股份有限公司 | Method for producing 1,2-epoxy cyclohexane and alpha, alpha-dimethyl benzyl alcohol |
| CN102010293A (en) * | 2010-11-02 | 2011-04-13 | 云南大学 | Method for catalyzing and synthesizing 1, 2-pentanediol by using titanium silicalite |
| CN103539762A (en) * | 2012-07-12 | 2014-01-29 | 中国石油化工股份有限公司 | Method for producing epoxypropane by propylene epoxidation |
| CN106831309A (en) * | 2015-12-03 | 2017-06-13 | 中国石油化工股份有限公司 | The method that n-amyl alcohol is dehydrated n-pentene processed |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107445796A (en) | 2017-12-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107445796B (en) | Method for co-producing dimethyl benzyl alcohol and 1, 2-pentanediol | |
| US2668180A (en) | Preparation of aryldialkyl peroxides | |
| DE60133557T2 (en) | CLEANING GLYCOL | |
| CN101704711B (en) | Method for preparing 1,2-diol compound by using catalytic hydration of epoxide | |
| DE2148637A1 (en) | Process for the production of catalysts and their use for the production of oxirane compounds | |
| US9029578B2 (en) | Method for preparation of anhydrosugar alcohols | |
| US2978464A (en) | Epoxtoahon of cyclododecatriene | |
| CN106146299B (en) | The method for producing acetic acid esters and ethylene glycol | |
| CN103664520B (en) | The method of Virahol is prepared in a kind of propylene hydration reaction | |
| CN101973837B (en) | Method for purifying beta-pinene | |
| CN108002977B (en) | Method for coproducing chemical products dimethylbenzyl alcohol and 1, 2-pentanediol | |
| DE1518967C3 (en) | Process for the production of styrenes | |
| CN107216240B (en) | Synthesis method of octoxy glycerol | |
| US3232996A (en) | Purification of butynediol | |
| CN111253343B (en) | Method for preparing styrene oxide by using metal-free catalyst | |
| CN109160892B (en) | Method for preparing 3-methylthio propanol by catalytic hydrogenation | |
| CN108129259B (en) | Catalyst and method for preparing chemical product 1, 2-pentanediol by catalysis of catalyst | |
| DE703226C (en) | ||
| DE1210777B (en) | Process for the production of epichlorohydrin | |
| DE965696C (en) | Process for the preparation of esters of glycol mono- (oxymethyl) ethers | |
| DE869063C (en) | Process for the preparation of ª ‡ -alkyl-3, 4-dichlorostyrenes | |
| GB1415427A (en) | Process for obtaining high-purity cyclopentene | |
| Kijeński et al. | Polyhydroxy alcohols as hydrogen donors in catalytic transfer reduction of carbonyl groups over MgO | |
| CN115959981A (en) | Production method and production system of hydratropic aldehyde/hydratropic alcohol | |
| DE1543026A1 (en) | Process for the production of glycerin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for 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: 20190221 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. Applicant after: Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences Address before: 414000 Changde Company, run by the Department of Caprolactam Business, Wangyue Road, Yueyang City, Hunan Province Applicant before: Changde Chemical Industry Co., Ltd., Yueyang Applicant before: Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences |
|
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CP03 | Change of name, title or address | ||
| CP03 | Change of name, title or address |
Address after: 414000 room 217, No. 111, yingpanling Road, Yueyang Economic and Technological Development Zone, Yueyang City, Hunan Province Patentee after: Changde Xincai Technology Co.,Ltd. Patentee after: Qingdao Institute of bioenergy and process, Chinese Academy of Sciences Address before: 414000 Room 209, 111 Yingpanling Road, Yueyang Economic and Technological Development Zone, Yueyang City, Hunan Province (office only) Patentee before: Yueyang Changde Environmental Technology Co.,Ltd. Patentee before: Qingdao Institute of bioenergy and process, Chinese Academy of Sciences |