CN111848326B - Industrial treatment method for recovering pentamethyl indane - Google Patents
Industrial treatment method for recovering pentamethyl indane Download PDFInfo
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- CN111848326B CN111848326B CN202010704421.8A CN202010704421A CN111848326B CN 111848326 B CN111848326 B CN 111848326B CN 202010704421 A CN202010704421 A CN 202010704421A CN 111848326 B CN111848326 B CN 111848326B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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Abstract
The invention relates to an industrial treatment method for recovering pentamethyl indane, which comprises the steps of rectifying and recovering galaxolide to obtain pentamethyl indane, slowly adding the pentamethyl indane into an oxidant/strong acid system, carrying out oxidation reaction with the oxidant/strong acid system at a certain temperature, reducing the temperature to a certain temperature after reaction, adding a certain amount of alkali liquor for neutralization, standing for layering, recovering manganese dioxide precipitated in an aqueous phase, adding a certain amount of water into the pentamethyl indane, washing, and finally obtaining the pentamethyl indane. The method improves the conversion rate of pentamethyl indane, reduces the production cost, greatly improves the production efficiency, simultaneously realizes the optimization of reaction efficiency and material utilization rate in the whole production flow, and increases the economic benefit of enterprises.
Description
The technical field is as follows:
the invention belongs to the technical field of chemical production, and relates to an industrial treatment method for recovering pentamethyl indane.
The background art comprises the following steps:
galaxolide (the name of english: galaxolide) was the first synthetic musk developed successfully in the 60 s by the international perfumery and fragrance company (IFF). The molecular weight is 258.4, the boiling point is 129 ℃ (107 Pa), the chemical name is 1,3,4,6,7, 8-hexahydro-4, 6,7, 8-hexamethylcyclopenta-gamma-2-benzopyran, the musk fragrance is strong and durable, and the costustoot fragrance is accompanied, so the musk fragrance and the costustoot fragrance are widely used in industries such as cosmetics, soap essence and the like.
Pentamethyl indane is used as an intermediate product of galaxolide, and the main industrial route at present is that alpha-methyl styrene and isoamylene react to generate pentamethyl indane under the condition that phosphoric acid is used as a catalyst, then the pentamethyl indane and epoxy propane perform Friedel-crafts alkylation reaction to obtain hexamethyl indane alcohol, and the hexamethyl indane alcohol reacts with methylal to obtain the galaxolide product.
However, in the industrial production of galaxolide, the problems of low reaction conversion rate and yield and the like exist in the friedel-crafts alkylation reaction of pentamethyl indan and propylene oxide, nearly 40% of pentamethyl indan does not participate in the reaction, so pentamethyl indan must be recovered in the rectification and purification process of galaxolide, but the yield of the recovered pentamethyl indan and the friedel-crafts alkylation reaction of propylene oxide is lower, and therefore an industrial treatment method for recovering pentamethyl indan is developed.
The invention content is as follows:
the invention aims to overcome the defect that the existing recovered pentamethyl indane has low yield in Friedel-crafts alkylation reaction with propylene oxide, and develops an industrial treatment method for recovering pentamethyl indane.
In the invention, 1) the galaxolide is rectified and recycled to obtain pentamethyl indan which is slowly added into an oxidant/strong acid system; the recovered pentamethyl indane is subjected to oxidation reaction with an oxidant/strong acid system at a certain temperature; 2) And cooling to a certain temperature after reaction, adding a certain amount of alkali liquor for neutralization, standing for layering, recovering manganese dioxide precipitated in the water phase, and adding a certain amount of water into the pentamethyl indane phase for washing to obtain the pentamethyl indane.
The acid for providing the strong acid system in the step 1) is sulfuric acid, and the concentration is 20-50%.
The oxidant selected in the step 1) is manganese dioxide.
The mass ratio of manganese dioxide to the recovered indane solution in the step 1) is 1:40-60.
The reaction temperature in the step 2) is controlled between 50 and 85 ℃.
In the step 2), the concentration of the alkali liquor is controlled to be 5-10%, and the molar ratio of the alkali liquor to the sulfuric acid is 1.2-1.5.
The invention has the advantages that:
1. the conversion rate of pentamethyl indane is improved, the production cost is reduced, and the production efficiency is greatly improved.
2. The reaction efficiency and the material utilization rate of the whole production flow are optimized, and the economic benefit of enterprises is obviously increased.
Description of the drawings:
FIG. 1 is a schematic process flow diagram of the present invention
Specific implementation method (see fig. 1):
1. 500kg of clear water is added into a 5000L indane recovery reaction kettle, stirring is started, 100kg of concentrated sulfuric acid (with the concentration of 98%) is slowly added, and the phenomena of heat release and smoking are controlled.
2. 2000kg of the recovered pentamethylindan solution (containing the solution) was slowly addedRectification processOrganic alcohols difficult to separate from pentamethylindan include chloropropanol, hexaMethyl indanol, etc.) and 50kg of manganese dioxide as an oxidant, starting steam to heat, raising the temperature in the kettle to 80 ℃, and keeping the temperature for two hours.
3. Closing steam, naturally cooling to 40 ℃, adding 500kg of 5% sodium hydroxide solution (carrying out neutralization reaction with sulfuric acid to enable reaction liquid to be alkaline) into the indane recycling reaction kettle, stirring for 1 hour, standing for 1 hour, naturally layering the mixed solution, discharging the lower-layer manganese dioxide/alkali liquid mixed liquid phase, introducing the manganese dioxide/alkali liquid mixed liquid into a centrifugal machine, centrifuging out excessive manganese dioxide, and using the excessive manganese dioxide for the next batch of reaction.
4. And (3) leaving the pentamethyl indane phase obtained in the upper layer in an indane recovery reaction kettle, adding 500kg of clear water, stirring for 1 hour, standing for 1 hour for natural layering, discharging the water phase in the lower layer, placing the indane phase in the upper layer in a standing tank to obtain the processed pentamethyl indane, and detecting the main peak content by gas chromatography to be more than 88%.
The foregoing is illustrative of the preferred embodiments of the present invention, and is not to be construed as limiting thereof in any way; those skilled in the art can make numerous possible variations and modifications to the present teachings, or modify equivalent embodiments to equivalent variations, without departing from the scope of the present teachings, using the methods and techniques disclosed above. Therefore, any simple modification, equivalent replacement, equivalent change and modification made to the above embodiments according to the technical essence of the present invention are still within the scope of the protection of the technical solution of the present invention.
Claims (4)
1. An industrial treatment method for recovering pentamethyl indane is characterized by comprising the following steps:
1) Rectifying and recovering galaxolide to obtain pentamethyl indane solution, slowly adding the pentamethyl indane solution into an oxidant/strong acid system, and carrying out oxidation reaction on the pentamethyl indane solution and the oxidant/strong acid system at a certain temperature;
2) Cooling to a certain temperature after reaction, adding a certain amount of alkali liquor for neutralization, standing for layering, recovering manganese dioxide precipitated in an aqueous phase, and adding a certain amount of water into the pentamethyl indane phase for washing to obtain pentamethyl indane finally;
the acid for providing the strong acid system in the step 1) is sulfuric acid, the concentration is 20-50%, and the selected oxidant is manganese dioxide.
2. An industrial process for the recovery of pentamethylindan according to claim 1, wherein the mass ratio of manganese dioxide to the recovered indane solution is 1:40-60.
3. The industrial process for recovering pentamethyl indane according to claim 1, wherein the oxidation reaction temperature in step 1) is controlled between 50-85 ℃.
4. The industrial process for recovering pentamethyl indane according to claim 1, wherein the concentration of alkali solution in step 2) is controlled to be 5-10%, and the molar ratio of alkali solution to sulfuric acid is 1.2-1.5.
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| CN202010704421.8A CN111848326B (en) | 2020-07-21 | 2020-07-21 | Industrial treatment method for recovering pentamethyl indane |
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| CN111848326B true CN111848326B (en) | 2023-03-10 |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113185487B (en) * | 2021-04-28 | 2022-09-23 | 安徽金轩科技有限公司 | Production process of Jiale musk |
| CN114014741A (en) * | 2021-11-17 | 2022-02-08 | 安徽金轩科技有限公司 | Industrial impurity removal method for recovering indane waste liquid from galaxolide |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4315951A (en) * | 1979-08-03 | 1982-02-16 | International Flavors & Fragrances Inc. | Flavoring with indane alkanols and tricyclic isochromans |
| US5034562A (en) * | 1990-06-08 | 1991-07-23 | Phillips Petroleum Company | Acid-sulfolance catalyzed production of cyclic alkylated compounds |
| CN108586420A (en) * | 2018-02-05 | 2018-09-28 | 杭州更蓝生物科技有限公司 | A kind of green synthesis process of Jiale muskiness |
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2020
- 2020-07-21 CN CN202010704421.8A patent/CN111848326B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4315951A (en) * | 1979-08-03 | 1982-02-16 | International Flavors & Fragrances Inc. | Flavoring with indane alkanols and tricyclic isochromans |
| US5034562A (en) * | 1990-06-08 | 1991-07-23 | Phillips Petroleum Company | Acid-sulfolance catalyzed production of cyclic alkylated compounds |
| CN108586420A (en) * | 2018-02-05 | 2018-09-28 | 杭州更蓝生物科技有限公司 | A kind of green synthesis process of Jiale muskiness |
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