CN112409147A - Method for preparing aldehyde or ketone by cracking acetylene still residual liquid - Google Patents
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
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Abstract
The invention provides a method for preparing aldehyde or ketone by cracking acetylization kettle residual liquid, which is characterized in that metal ions, cyanide ions and polyether are added into a system, the reverse reaction of acetylization is realized at high temperature to obtain aldehyde or ketone substances, the by-products of the acetylization reaction are comprehensively utilized, the aldehyde or ketone substances are recovered, the production cost is reduced, and the benefit is improved.
Description
Technical Field
The invention relates to the field of fine chemical engineering, and particularly relates to a method for preparing aldehyde or ketone by cracking acetylene still residual liquid.
Background
Alkynol is an important fine chemical product, and the main synthesis method is that ketone or aldehyde is used as raw material and is obtained through ethynylation reaction. The ethynylation reagent is mainly acetylene gas or acetylene format reagent, and the acetylene gas has low price and cost advantage. The production of VE, vitamin a, carotenoid intermediates, flavours and other products involves ethynylation. The mainstream process for ethynylation is the use of acetylene gas as the ethynylation agent.
The linear structure of acetylene ensures that the selectivity of the ethynylation reaction is higher, and the main byproduct is an acetylene glycol substance formed by the secondary ethynylation of the raw material. Generally, the mass content of the alkynediol product in the crude ethynylation product is not high, but after the crude product is rectified or distilled, the concentration content of the alkynediol is increased, the crude product is reddish brown or black, has high viscosity, cannot be directly discharged to the environment, and generally needs to be incinerated. This not only causes waste of resources, but also brings environmental protection pressure.
A process for the preparation of ketone mixtures from acetylenic diols is reported in the patent CN200680036353 filed by the company tesleman. In a process for preparing dehydrolinalool and dehydroisophytol, acetylenic diol is converted into the starting ketone compound by cleavage using a basic catalyst, the molar ratio of catalyst to acetylenic diol being carried out in the range from 1:10 to 1:30, the temperature being 80 to 100 ℃, 50mbar to atmospheric pressure.
The application patent CN200610118590 of China petrochemical company reports that 6-methyl-5-heptene-2-ketone alkynediol in waste liquid for producing dehydrolinalool is depolymerized by using alkali solution to obtain 6-methyl-5-heptene-2-ketone, oil-water separation is carried out on the depolymerization reaction product, the alkali solution is recycled and reused, the oil phase material is distilled by using water vapor to obtain crude 6-methyl-5-heptene-2-ketone, then the crude 6-methyl-5-heptene-2-ketone is decompressed, rectified and purified, and the overhead fraction at 72-74 ℃ is collected to obtain refined 6-methyl-5-heptene-2-ketone. 75-80 Kg of refined methyl heptenone product can be obtained from every 100Kg of waste liquid.
However, the existing scheme has obvious disadvantages, firstly, the acetylene still waste liquid has complex components, the waste liquid needs to be pretreated to remove high boiling point substances in the prior art, and distillation or rectification and other modes such as reduced pressure distillation, reduced pressure rectification or steam distillation are usually adopted. So as to obtain mixed liquid with higher content of alkynediol, but simultaneously increase energy consumption and improve process requirements. Secondly, the waste liquid at the bottom of the ethynylation tower has high viscosity and poor fluidity, and the prior art uses an inorganic alkaline aqueous solution as a catalyst, so that the mass transfer of oil and water phases is poor, and the reaction rate is limited.
Disclosure of Invention
The invention aims to solve the technical problems and provides a method for preparing aldehyde or ketone by cracking acetylization kettle residual liquid, which aims to realize the following purposes:
1. metal ions and cyanide ions are added into waste liquid in the acetylene tower kettle, the reverse reaction of the acetylene reaction is directly realized at high temperature to obtain aldehyde or ketone substances, the reaction rate is high, and the recovery rate is high. Polyether is added to reduce the viscosity of the system, improve the solubility of metal ions in the system and promote the reaction. Rectifying to obtain high-purity aldehyde or ketone substances.
2. The polyether is efficiently recovered by regulating and controlling the temperature.
The invention provides a method for preparing aldehyde or ketone by cracking acetylization kettle residual liquid, which is used for preparing aldehyde or ketone by cracking the acetylization kettle residual liquid under the catalysis of metal ions and cyanide ions.
In the invention, the residual liquid of the ethynylation kettle is a byproduct of the ethynylation reaction, namely a reaction byproduct containing an acetylene glycol substance with a structure shown in formula II, which is obtained by carrying out the ethynylation reaction twice on a ketone or aldehyde compound with the structure shown in formula I;
wherein R is1、R2Each independently is hydrogen or hydrocarbyl, and R1、R2Not both hydrogen, preferably a branched or straight chain C1-C20 alkyl or alkenyl group.
In the invention, the main component of the ethynylation kettle residual liquid is acetylene glycol substances which are by-products of the ethynylation reaction, high-concentration acetylene glycol substances exist in the tower bottom liquid after rectification or distillation treatment in the production process, the mass concentration of the acetylene glycol substances in the tower bottom liquid is 30-95%, and the materials are red brown or black viscous liquid.
Further, the ketone or aldehyde compounds include, but are not limited to, acetone, 6-methyl-5-hepten-2-one, 6-methyl-2-heptanone, geranylacetone, tetrahydrogeranylacetone, phytone, and the like, the corresponding structural formulas of which are as follows:
the acetylene glycol substances contained in the corresponding by-products are: acetonynediol, 6-methyl-5-hepten-2-one alkynediol, 6-methyl-2-heptone alkynediol, geranylacetone alkynediol, tetrahydrogeranylacetone alkynediol, phytone alkynediol, and the like, having the following structural formula:
in the invention, the metal ions are preferably cuprous ions, silver ions and mercury ions, the metal salt compound is added into the ethynylation kettle residual liquid to provide the metal ions, and the metal salt compound added into the ethynylation kettle residual liquid is copper, silver or mercury salt, such as cuprous chloride, silver nitrate, mercury nitrate and the like. The amount of the metal salt compound added is 0.01-10 percent of the mass of the residual liquid of the ethynylation kettle, and preferably 0.05-2 percent.
In the present invention, the cyanide ion may be introduced by adding a cyanide-containing compound, such as sodium cyanide, potassium cyanide, mercury cyanide, and the like. The amount of the cyanide-containing compound added is 0.01-10%, preferably 0.1-4% of the mass of the residual liquid of the ethynylation kettle.
The metal ions and cyanide ions can also be obtained by directly adding metal cyanides, such as cuprous cyanide, silver cyanide, mercury cyanide and the like. The amount of the added metal cyanide is 0.01 to 10 percent of the mass of the residual liquid of the ethynylation kettle, and preferably 0.05 to 2 percent.
The combined action of metal ions and cyanide ions in the metal cyanide promotes the cracking of acetylene still residual liquid, the metal ions and acetylene bond electron cloud act to polarize acetylene bonds and promote the breaking of carbon-carbon bonds (the covalent bond is formed by the carbon atoms 1 and 2) between acetylene bond carbon atoms (the carbon atom 2 is marked in the structural formula) and carbon atoms connected with hydroxyl groups (the carbon atom 1 is marked in the structural formula), but the single metal ions and acetylene bond electron cloud act insufficiently to efficiently break the carbon-carbon bonds, after the cyanide ions are added into a system, the linear structure of the cyanide ions is beneficial to efficiently and highly selectively attacking the carbon atoms connected with the hydroxyl groups, the polarity of the carbon-carbon bonds is weakened, and the combined action of the metal ions and the cyanide ions is efficiently and directionally attacked to promote the breaking of the carbon-carbon bonds.
In the invention, in the cracking reaction of the acetylization kettle residual liquid, the reaction temperature is 60-250 ℃, the preferable temperature is 90-180 ℃, the reaction time is 0.1-24 h, the preferable time is 2-8 h, and the reaction pressure (absolute pressure) is 0.1-101 KPa.
In the invention, polyether is added in the cracking reaction of the acetylene still residual liquid, and the polyether is added in the system, so that the solubility of metal ions in the tower still waste liquid can be improved, and the viscosity of the system can be reduced. The polyether is polyalcohol polymer, and can be selected from one or more of polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyoxypropylene triol, polyoxypropylene hexaol, etc., such as polyethylene glycol-4000, polyethylene glycol-6000, polypropylene glycol-4000, etc. The amount of the added polyether substance is 10 to 500 percent of the mass of the residual liquid of the ethynylation kettle, preferably 25 to 200 percent.
In the invention, the alkynediol in the residual liquid of the ethynylation kettle is subjected to the reverse ethynylation reaction to produce the ketone or aldehyde compound, the ketone or aldehyde compound is separated by a rectification method, the high-purity ketone or aldehyde compound is obtained at the tower top, and heavy components of tar and polyether are taken at the tower bottom.
In the invention, heavy components of tar and polyether are taken from the tower bottom, and polyether can be recovered through temperature regulation. Since polyether has a property of cloud point, polyether exhibits lipophilicity at a temperature higher than the cloud point, and polyether exhibits hydrophilicity at a temperature lower than the cloud point, and polyether can be separated by utilizing this property.
In the invention, the specific method for recovering polyether comprises the steps of adding pure water into a tower kettle, cooling, enabling polyether to enter a water phase after the temperature is reduced to be below the cloud point of polyether, and separating and layering the liquid and the water phase to obtain the polyether aqueous solution. Heating the polyether water solution to above the cloud point, starting layering, keeping the temperature, separating out an organic phase, and recovering the polyether.
The invention has the positive effects that:
firstly, the acetylene tower kettle rectification waste liquid which is originally treated as the waste liquid is fully utilized, ketone or aldehyde compounds with economic value are recovered, the reverse reaction of the acetylene reaction can be realized by matching metal ions and cyanide ions, the reaction feasibility is high, the operation is simple, and the kettle residual liquid recovery rate is high.
Secondly, polyether is added to promote the reaction rate to be improved, the fluidity is increased, and the difficulty in model selection of industrial equipment is reduced.
And moreover, the polyether is recovered through temperature regulation, so that the operation is simple and the method is suitable for actual production.
Detailed Description
The process of the present invention will be further illustrated by the following examples, but the present invention is not limited to the examples listed, but also includes any other known variations within the scope of the claims of the present invention.
The analysis method comprises the following steps:
gas chromatograph: agilent7820A, column HP-5(30 m.times.320. mu.m.times.0.25 μm), injection port temperature: 120 ℃; the split ratio is 50: 1; carrier gas flow: 1.5 ml/min; temperature rising procedure: keeping at 40 deg.C for 1min, heating to 90 deg.C at 10 deg.C/min for 0min, heating to 160 deg.C at 5 deg.C/min for 0min, heating to 280 deg.C at 30 deg.C/min for 6 min. Detector temperature: 280 ℃.
Cuprous chloride, 99 w%, welfare technologies ltd;
99 w% of mercuric nitrate, lark technologies ltd;
silver nitrate, 99 w%, welfare technologies ltd;
the mass content of 2-methyl-3-butyne-2-ol in the acetone ethynylation rectification residual liquid is 2.5 percent, the mass content of acetone acetylenediol is 61.9 percent, and the other components are mainly polymer impurities.
3, 7-dimethyl-6-octen-1-alkynyl-3-ol, 6-methyl-5-hepten-2-one alkynediol and polymer impurities are mainly contained in the 6-methyl-5-hepten-2-one ethynylation rectification residual liquid, wherein the mass content of the 3, 7-dimethyl-6-octen-1-alkynyl-3-ol is 3.1%, and the mass content of the 6-methyl-5-hepten-2-one alkynediol is 57.1%.
The mass content of the dehydroisophytol in the residual liquid of the acetylized rectification of the phytone is 5.5 percent, the mass content of the phytone acetylenic diol is 67.1 percent, and the other components are mainly polymer impurities.
Example 1
Acetone recovery
The number of theoretical plates of the rectifying tower is 5, 2000g of acetone ethynylation rectifying residual liquid, 1g of mercury nitrate, 2g of sodium cyanide and 1000g of polyethylene glycol-4000 are added into the tower kettle. The condenser at the top of the tower uses 10 ℃ chilled water as a refrigerant, and the reboiler at the bottom of the tower controls the temperature at the bottom of the tower and controls the temperature in the kettle to be 90-92 ℃. The operation was carried out at atmospheric pressure with a reflux ratio of 3: 1. 1032.8g of overhead fraction is collected after 6h, and the components are sampled and detected: the content of acetone is 99.31%, the content of 2-methyl-3-butyn-2-ol is 0.68%, and the content of others is 0.01%.
Polyether recovery
Taking out the tower bottom liquid of the rectifying tower, adding 1000g of pure water, mixing, cooling, stopping mixing after the temperature is reduced to room temperature, separating a lower-layer water phase after obvious layering occurs in standing, and obtaining 1985.7g of the water phase.
Stirring the separated water phase, heating to 90 ℃, stopping stirring, keeping the temperature, standing for obvious layering, separating an upper organic phase, and obtaining 989.2g of an organic phase. The polyether content in the organic phase was 99.2%.
Example 2
6-methyl-5-hepten-2-one recovery
The number of theoretical plates of the rectifying tower is 5, 2000g of 6-methyl-5-heptene-2-ketone ethynylation rectifying residual liquid, 2g of cuprous chloride, 4g of mercuric cyanide and 500g of polyethylene glycol-6000 are added into the tower bottom. The condenser at the top of the tower uses circulating water of 20 ℃ as a refrigerant, and the reboiler at the bottom of the tower controls the temperature at the bottom of the tower and controls the temperature in the kettle to be 125-127 ℃. The operation was carried out at 10KPa, reflux ratio 3: 1. 1068.3g of overhead fraction is collected in 8h, and the components are sampled and detected: the content of 6-methyl-5-hepten-2-one was 99.27%, the content of 3, 7-dimethyl-6-octen-1-ynyl-3-ol was 0.71%, and the other was 0.02%.
Polyether recovery
Taking out the tower bottom liquid of the rectifying tower, adding 800g of pure water, mixing, cooling, stopping mixing after the temperature is reduced to room temperature, separating a lower-layer water phase after obvious layering occurs in standing, and obtaining 1286.2g of the water phase.
Stirring the separated water phase, heating to 100 ℃, stopping stirring, keeping the temperature, standing for obvious layering, separating an upper organic phase to obtain 485.7g of an organic phase. The polyether content in the organic phase was 99.5%.
Example 3
6-methyl-5-hepten-2-one recovery
The number of theoretical plates of the rectifying tower is 5, 2000g of 6-methyl-5-heptene-2-ketone ethynylation rectifying residual liquid, 40g of cuprous nitrate, 80g of potassium cyanide and 2000g of polypropylene glycol-4000 are added into the tower bottom. The condenser at the top of the tower uses 10 ℃ chilled water as a refrigerant, and the reboiler at the bottom of the tower controls the temperature at the bottom of the tower and controls the temperature in the kettle to be 125-127 ℃. The operation was carried out at 10KPa, reflux ratio 3: 1. 1071.1g of overhead fraction is collected in 8h, and the components are sampled and detected: the content of 6-methyl-5-hepten-2-one was 99.31%, the content of 3, 7-dimethyl-6-octen-1-ynyl-3-ol was 0.67%, and the other was 0.02%.
Polyether recovery
Taking out the tower bottom liquid of the rectifying tower, adding 2000g of pure water, mixing, cooling, stopping mixing after the temperature is reduced to room temperature, separating a lower-layer water phase after obvious layering occurs in standing, and obtaining 3976.1g of the water phase.
Stirring the separated water phase, heating to 100 ℃, stopping stirring, keeping the temperature, standing for obvious layering, separating an upper organic phase to obtain 1989.2g of an organic phase. The polyether content in the organic phase was 99.1%.
Example 4
Phytone recovery
The number of theoretical plates of the rectifying tower is 5, 2000g of phytone acetylized rectification residual liquid, 100g of mercury nitrate, 2g of sodium cyanide and 4000g of polyethylene glycol-4000 are added into the tower kettle. The condenser at the top of the tower uses 10 ℃ chilled water as a refrigerant, and the reboiler at the bottom of the tower controls the temperature at the bottom of the tower and controls the temperature in the kettle to be 151-152 ℃. The operation was carried out at 0.2KPa, reflux ratio 3: 1. And collecting 1051.1g of overhead fraction after 12h, and sampling to detect the content of components: the phytone content is 99.52%, the dehydroisophytol content is 0.45% and the others are 0.03%.
Polyether recovery
Taking out the tower bottom liquid of the rectifying tower, adding 2000g of pure water, mixing, cooling, stopping mixing after the temperature is reduced to room temperature, separating a lower-layer water phase after obvious layering occurs in standing, and obtaining 5989.1g of the water phase.
Stirring the separated water phase, heating to 100 ℃, stopping stirring, keeping the temperature, standing for obvious layering, separating an upper organic phase to obtain 3985.2g of an organic phase. The polyether content in the organic phase was 99.3%.
Example 5
Phytone recovery
The number of theoretical plates of the rectifying tower is 5, 2000g of phytolynized rectification residual liquid, 10g of mercuric cyanide and 1000g of polyethylene glycol-4000 are added into the tower bottom. The condenser at the top of the tower uses 10 ℃ chilled water as a refrigerant, and the reboiler at the bottom of the tower controls the temperature at the bottom of the tower and controls the temperature in the kettle to be 151-152 ℃. The operation was carried out at 0.2KPa, reflux ratio 4: 1. And (3) collecting 1046.2g of overhead fraction in 16h, sampling and detecting the content of components: the phytone content is 99.61%, the dehydroisophytol content is 0.36%, and the others are 0.03%.
Polyether recovery
Taking out the tower bottom liquid of the rectifying tower, adding 1000g of pure water, mixing, cooling, stopping mixing after the temperature is reduced to room temperature, separating a lower-layer water phase after obvious layering occurs in standing, and obtaining 1987.2g of the water phase.
Stirring the separated water phase, heating to 100 ℃, stopping stirring, keeping the temperature, standing for obvious layering, separating an upper organic phase to obtain 984.9g of an organic phase. The polyether content in the organic phase was 99.2%.
Comparative example 1
Acetone recovery
The number of theoretical plates of the rectifying tower is 5, 2000g of acetone ethynylation rectifying residual liquid, 2g of copper acetylide and 1000g of polyethylene glycol-4000 are added into the tower bottom. The condenser at the top of the tower uses 10 ℃ chilled water as a refrigerant, and the reboiler at the bottom of the tower controls the temperature at the bottom of the tower and controls the temperature in the kettle to be 90-92 ℃. The operation was carried out at atmospheric pressure with a reflux ratio of 3: 1. No fraction is collected at the top of the tower after 6h of reaction, and the components are sampled and detected at the bottom of the tower: the mass content of the 2-methyl-3-butyne-2-ol is 0.76 percent, the mass content of the acetone acetylene glycol is 59.11 percent, and the mass content of the other components is 40.13 percent.
Claims (9)
1. The method for preparing aldehyde or ketone by cracking the acetylene still residual liquid is characterized by comprising the following steps: and (3) cracking the residual liquid of the ethynylation kettle under the catalysis of metal ions and cyanide ions to prepare aldehyde or ketone.
2. The method according to claim 1 or 2, wherein the ethynylation kettle residual liquid is a reaction byproduct of ethynylation reaction, which is a reaction byproduct of a ketone or aldehyde compound with a structure shown in formula I and containing an acetylene glycol substance with a structure shown in formula II;
wherein R is1、R2Each independently is hydrogen or hydrocarbyl, and R1、R2Not both hydrogen, preferably a branched or straight chain C1-C20 alkyl or alkenyl group;
preferably, the ketone or aldehyde compound includes, but is not limited to, acetone, 6-methyl-5-hepten-2-one, 6-methyl-2-heptanone, geranylacetone, tetrahydrogeranylacetone, phytone;
preferably, the acetylene glycol contained in the corresponding by-product is: acetonynediol, 6-methyl-5-hepten-2-one alkynediol, 6-methyl-2-heptone alkynediol, geranylacetone alkynediol, tetrahydrogeranylacetone alkynediol, phytone alkynediol, and the like;
preferably, the mass concentration of the alkynediol substances in the ethynylation kettle residual liquid is 30-95%.
3. The method according to claims 1-2, wherein the metal ions are preferably cuprous ions, silver ions, mercury ions, preferably the metal ions are introduced by adding metal salt compounds; the metal salt compounds added into the waste liquid of the ethynylation tower are copper, silver or mercury salts, preferably cuprous chloride, silver nitrate and mercury nitrate;
preferably, the amount of the metal salt compound added is 0.01 to 10 percent of the mass of the ethynylation kettle residual liquid, and more preferably 0.05 to 2 percent.
4. A process according to claims 1-3, characterized in that the cyanide ions are introduced by adding cyanide-containing compounds, preferably sodium cyanide, potassium cyanide, mercury cyanide; preferably, the amount of the cyanide-containing compound added is 0.01-10%, preferably 0.1-4% of the mass of the acetylene tower kettle waste liquid.
5. The method according to claim 1 or 2, characterized in that the metal ions, cyanide ions, can also be obtained by direct addition of metal cyanides, preferably cuprous cyanide, silver cyanide, mercury cyanide. The amount of the added metal cyanide is 0.01 to 10 percent of the mass of the residual liquid of the ethynylation kettle, and preferably 0.05 to 2 percent.
6. The method according to any one of claims 1 to 5, wherein the reaction temperature of the cracking reaction of the ethynylation kettle residual liquid is 60-250 ℃, preferably 90-180 ℃, the reaction time is 0.1-24 h, preferably 2-8 h, and the reaction pressure is 0.1-101 KPa.
7. The method according to any one of claims 1 to 6, wherein a polyether is added into the cracking reaction system of the ethynylation kettle residual liquid, the polyether is selected from one or more of polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyoxypropylene triol and polyoxypropylene hexaol, and the amount of the polyether is 10 to 500 percent, preferably 25 to 200 percent of the mass of the ethynylation kettle residual liquid.
8. The method as claimed in any one of claims 1 to 7, wherein the acetylenic diol in the ethynylation still residue is subjected to a reverse ethynylation reaction to produce ketone or aldehyde compounds, the ketone or aldehyde compounds are separated by rectification, the high-purity ketone or aldehyde compounds are obtained at the top of the tower, and heavy components of tar and polyether are taken from the bottom of the tower.
9. The method of claim 8, wherein the heavy tar and polyether are separated and recovered from the bottom of the tower by temperature control.
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| CN114133316A (en) * | 2021-11-16 | 2022-03-04 | 万华化学集团股份有限公司 | Dehydroisophytol, and preparation method and application thereof |
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| CN101277918A (en) * | 2005-09-29 | 2008-10-01 | 帝斯曼知识产权资产管理有限公司 | Cleavage of alkynediols |
| CN110467519A (en) * | 2019-09-16 | 2019-11-19 | 万华化学集团股份有限公司 | A kind of Ethynylation process |
| CN110511127A (en) * | 2019-09-16 | 2019-11-29 | 万华化学集团股份有限公司 | A method of alpha-alcohol ketone is prepared using ethynylation by-product |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101277918A (en) * | 2005-09-29 | 2008-10-01 | 帝斯曼知识产权资产管理有限公司 | Cleavage of alkynediols |
| CN110467519A (en) * | 2019-09-16 | 2019-11-19 | 万华化学集团股份有限公司 | A kind of Ethynylation process |
| CN110511127A (en) * | 2019-09-16 | 2019-11-29 | 万华化学集团股份有限公司 | A method of alpha-alcohol ketone is prepared using ethynylation by-product |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114133316A (en) * | 2021-11-16 | 2022-03-04 | 万华化学集团股份有限公司 | Dehydroisophytol, and preparation method and application thereof |
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