CN113603608B - Glycosyl propylamine compound, preparation method and application thereof as flotation agent - Google Patents

Glycosyl propylamine compound, preparation method and application thereof as flotation agent Download PDF

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Publication number
CN113603608B
CN113603608B CN202110907789.9A CN202110907789A CN113603608B CN 113603608 B CN113603608 B CN 113603608B CN 202110907789 A CN202110907789 A CN 202110907789A CN 113603608 B CN113603608 B CN 113603608B
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glycosyl
alkyl
propylamine
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CN113603608A (en
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张海
刘洋
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Shandong Fusite Oil Technology Co ltd
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Shandong Fusite Oil Technology Co ltd
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Priority to CN202310776194.3A priority patent/CN116903685A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D1/00—Flotation
    • B03D1/001—Flotation agents
    • B03D1/004—Organic compounds
    • B03D1/01—Organic compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D2201/00—Specified effects produced by the flotation agents
    • B03D2201/02—Collectors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B03—SEPARATION OF SOLID MATERIALS USING LIQUIDS OR USING PNEUMATIC TABLES OR JIGS; MAGNETIC OR ELECTROSTATIC SEPARATION OF SOLID MATERIALS FROM SOLID MATERIALS OR FLUIDS; SEPARATION BY HIGH-VOLTAGE ELECTRIC FIELDS
    • B03D—FLOTATION; DIFFERENTIAL SEDIMENTATION
    • B03D2203/00—Specified materials treated by the flotation agents; specified applications
    • B03D2203/02—Ores
    • B03D2203/04—Non-sulfide ores

Abstract

The invention discloses a glycosyl propylamine compound structure, which is shown in a structural general formula (I), a structural general formula (II) or a structural general formula (III), and also discloses a preparation method of the glycosyl propylamine compound structure and application of the glycosyl propylamine compound structure serving as a flotation agent. The molecular structure of the compound contains glycosyl, so that the toxicity of the product can be greatly reduced; and the molecular structure is also provided with easily degradable amide bond and ether bond, thus the biodegradability of the product can be greatly improved.

Description

Glycosyl propylamine compound, preparation method and application thereof as flotation agent
Technical Field
The invention relates to glycosyl propylamine compounds, a preparation method and application thereof as a flotation agent, and belongs to the field of mineral flotation agents.
Background
The mining industry is closely related to various fields such as daily life, industrial demand and the like of people, and is an essential basic industry for sustainable development of national economy. With the rapid development of social economy, the demands of mineral resources are increased, and the phenomena of mineral resource impurity, fineness, deficiency and the like are continuously aggravated, so that the difficulty of mineral extraction is increased. The flotation technology is the mineral separation technology with the most widely applied and development potential at present due to the advantages of high separation efficiency, strong adaptability and the like. In the ore dressing of metal oxide ores, nonmetallic ores and the like, the amine compounds have good use effects in the aspects of separating silicate from phosphate ores, separating potassium sodium salt from potassium sodium salt, separating mineral from quartz from iron oxide ores, separating silicate from silicate, separating silicate from silicic acid and other minerals from mica, separating lead zinc oxide ores and the like.
Most of the amine flotation agents commonly used at present are prepared from non-renewable resources such as petroleum, coal and the like, and have the problems of toxicity, difficult degradation and the like, so that sustainable development is not facilitated, serious harm is caused to the environment, animals, plants and the like, and development of low-toxicity and high-degradation amine flotation agent products prepared from natural renewable resources has important significance for sustainable development of mineral flotation processes. At present, glycosyl amine compounds prepared by using glycosyl products as raw materials are not reported.
Disclosure of Invention
The invention aims to provide glycosyl propylamine compounds, a preparation method and application thereof as a flotation agent.
The invention provides a glycosyl propylamine compound structure, which is shown as a structural general formula (I), a structural general formula (II) or a structural general formula (III),
wherein m is selected from 8-14, n is selected from 7-15.
The glycosylpropylamines according to the invention are preferably selected from the following compounds:
numbering device Structure name Structural formula
1 3-hexadecyl glycosidoxy propylamine Example 1
2 3-N-methyl-N-dodecyl-glucamide oxypropylamine Example 2
3 3-octyl amidooxypropylamine Example 3
4 3-dodecyl glycosidoxy propylamine Example 4
5 3-N-methyl-N-decanyl-glucamide oxypropylamine Example 5
The invention provides a preparation method of glycosyl propylamine compounds, which has the reaction route as follows,
wherein m is selected from 8-14, n is selected from 7-15.
The invention provides a preparation method of glycosyl propylamine compounds, which adopts glucamide/alkyl glycoside as raw material, and firstly reacts with acrylonitrile under the condition of taking solid alkali as a catalyst to obtain alkyl glycosyl propionitrile; then, hydrogenation reaction is carried out under the condition of Raney-Ni (Raney nickel) as a catalyst, so as to synthesize a novel propylamine compound containing alkyl glycosyl. Because the molecular structure of the product contains glycosyl, the toxicity of the product can be greatly reduced; the molecular structure of the product is also provided with easily degradable amide bond and ether bond, the biodegradability of the product can be greatly improved, and the product can be used as an excellent substitute for alkyl propylamine compounds in the aspects of mineral check and daily washing.
The invention provides a preparation method of glycosyl propylamine compounds, which comprises the following reaction steps:
step one: cyclohexane, alkyl glycosyl compound and solid base catalyst according to the mass ratio (8-15): 1: (0.5-5 mill) adding into a container, slowly adding acrylonitrile, reacting for 5-9h, thermally filtering, cooling, and evaporating solvent to obtain 3-alkyl glycosyl oxypropionitrile.
Wherein the alkyl glycosyl compound is one or a combination of a plurality of N-methyl-N-alkyl glucamide, alkyl glucamide or alkyl glycoside.
Wherein the solid base catalyst is one or two of sodium hydroxide and potassium hydroxide.
Wherein the reaction temperature is 40-80 ℃, preferably: 50-65 ℃.
Wherein, the acrylonitrile is added dropwise. Preferably, the mixture is added dropwise at a constant speed.
Wherein the molar ratio of acrylonitrile to alkyl glycosyl compound is 0.9-1.3, preferably 1.0-1.1.
Step two: adding cyclohexane, 3-alkyl glycosyl oxypropionitrile, raney-Ni catalyst and inhibitor NH3.H2O into a high-pressure reaction vessel, replacing with N2, stirring, heating to 60-90 ℃, introducing H2 into the high-pressure reaction vessel, reacting for 5-9H, discharging, hot filtering, and distilling under reduced pressure to remove solvent to obtain the 3-alkyl glycosyl oxypropylamine.
Wherein: the mass ratio of cyclohexane to 3-alkyl glycosyloxy propionitrile is 8-13:1, preferably 9-12:1.
wherein: raney-Ni catalyst is used in an amount of 2-12wt%, preferably 2-8% based on the mass of 3-alkyl glycosyloxy propionitrile.
Wherein: nitrogen substitution is required, preferably 3 times, before flushing with hydrogen.
Wherein: the reaction temperature is 60-90 ℃, preferably 70-85 ℃.
Wherein: the reaction pressure is 1.5-4.0MPa, preferably 1.8-3.5MPa.
Preferably: the content of the 3-alkyl glycosyl oxypropylamine of the product is calculated according to the determination method of total amine, primary amine, secondary amine and tertiary amine in national standard GB/T15045-2013 fatty alkyl dimethyl tertiary amine, and the purity of the product is more than 90%.
The invention provides an application of glycosyl propylamine compounds as a flotation agent.
Compared with the prior art, the invention has the following advantages:
1. the glycosyl is derived from renewable resources, can replace non-renewable resources such as petroleum, coal and the like, and increases the sustainable development of amine products.
2. The amine products after glycosyl is added have better biocompatibility, lower toxicity, good biodegradability and more environmental protection.
3. Current common amine collectors have poor solubility in water and must be neutralized with acid to increase their solubility in water. But not as high as better, higher neutralization may increase the solubility of the flotation agent, but may impair the flotation behavior. After glycosyl groups are introduced into the molecules, the water solubility of the molecules can be increased, neutralization by acid is not needed, the operation procedure is greatly reduced, and the use cost is reduced.
4. The compound has a good floatation effect on minerals, and can be used as a high-efficiency floatation agent.
Detailed Description
Example 1: 3-hexadecyl glycosidoxy propylamine
In a 250mL flask were charged 150mL of cyclohexane, 10g (25 mmol) of hexadecyl glycoside and 0.01g of sodium hydroxide. After the raw materials are added, stirring is started, the mixture is heated to 60 ℃, then 1.33g (25 mmol) of acrylonitrile is added dropwise, after the acrylonitrile is added dropwise, the reaction is continued for 9 hours, after hot filtration, the temperature is reduced, and a rotary evaporator is used for evaporating the solvent, so that the 3-hexadecyl glycosidoxy propionitrile is obtained.
150mL of cyclohexane, 10g of 3-hexadecyl glycosidoxy propionitrile, 0.5g of Raney-Ni catalyst and inhibitor NH are added into a high-pressure reaction kettle 3 ·H 2 O0.5 g with N 2 3 substitutions. Stirring is started, after the temperature is raised to 75 ℃, H is introduced into the kettle 2 (pressure: 2 MPa), after 5 hours of reaction, discharging, after hot filtration, evaporating the solvent by a rotary evaporator to obtain a product 3-Cetyl glycosidoxypropylamine content was determined to be 91%.
Example 2: 3-N-methyl-N-dodecyl-glucamide oxypropylamine
In a 250ml flask were charged 150ml of cyclohexane, 10g (26.5 mmol) of N-methyl-N-dodecylglucamide and 0.05g of sodium hydroxide. After the raw materials are added, stirring is started, the mixture is heated to 55 ℃, then 1.41g (26.5 mmol) of acrylonitrile is added dropwise, after the acrylonitrile is added dropwise, the reaction is continued for 7 hours, after hot filtration, the temperature is reduced, and a rotary evaporator is used for evaporating the solvent, so that the 3-N-methyl-N-dodecyl glucose amide oxypropionitrile is obtained.
150mL of cyclohexane, 10g of 3-N-methyl-N-dodecyl glucose amide oxypropionitrile, 0.7g of Raney-Ni catalyst and an inhibitor NH are added into a high-pressure reaction kettle 3 ·H 2 O0.5 g with N 2 3 substitutions. Stirring is started, after the temperature is raised to 75 ℃, H is introduced into the kettle 2 (pressure is 2.5 MPa), after 7h of reaction, discharging, hot filtering, evaporating the solvent by a rotary evaporator to obtain the product 3-N-methyl-N-dodecyl glucose amidoxypropylamine, wherein the content is measured to be 93%.
Example 3: 3-octyl glucamide oxypropylamine
In a 250mL flask were charged 150mL of cyclohexane, 10g (32.5 mmol) of octaalkyl glucamide and 0.1g of sodium hydroxide. After the raw materials are added, stirring is started, the mixture is heated to 50 ℃, then 1.72g (32.5 mmol) of acrylonitrile is added dropwise, after the acrylonitrile is added dropwise, the reaction is continued for 5 hours, after hot filtration, the temperature is reduced, and a rotary evaporator is used for evaporating the solvent, so that the 3-octaalkyl glucose amide oxypropionitrile is obtained.
150mL of cyclohexane, 10g of 3-octaalkyl glucose amide oxypropionitrile, 1g of Raney-Ni catalyst and an inhibitor NH are added into a high-pressure reaction kettle 3 ·H 2 O0.5 g with N 2 3 substitutions. Stirring is started, after the temperature is raised to 75 ℃, H is introduced into the kettle 2 (pressure is 2 MPa), after 9h of reaction, discharging, hot filtering, evaporating the solvent by a rotary evaporator to obtain the product 3-octaalkyl glucose amidoxypropylamine, wherein the content is measured to be 90%.
Example 4: 3-dodecyl glycosidoxy propylamine
In a 250mL flask were charged 150mL of cyclohexane, 10g (28.3 mmol) of dodecyl glycoside and 0.08g of sodium hydroxide. After the raw materials are added, stirring is started, the mixture is heated to 60 ℃, then 1.50g (28.3 mmol) of acrylonitrile is added dropwise, after the acrylonitrile is added dropwise, the reaction is continued for 8 hours, after hot filtration, the temperature is reduced, and a rotary evaporator is used for evaporating the solvent, so that the 3-dodecyl glycosidoxy propionitrile is obtained.
150mL of cyclohexane, 10g of 3-dodecyl glycosidoxy propionitrile, 0.8g of Raney-Ni catalyst and inhibitor NH are added into a high-pressure reaction kettle 3 ·H 2 O0.5 g with N 2 3 substitutions. Stirring is started, after the temperature is raised to 75 ℃, H is introduced into the kettle 2 (pressure is 2.5 MPa), after reaction for 8 hours, discharging, hot filtering, evaporating the solvent by a rotary evaporator to obtain the product 3-dodecyl glycosidoxypropylamine, wherein the content is determined to be 95%.
Example 5: 3-N-methyl-N-decanyl-glucamide oxypropylamine
In a 250ml flask were charged 150mL of cyclohexane, 10g (28.6 mmol) of N-methyl-N-decanyl-glucamide and 0.06g of sodium hydroxide. After the raw materials are added, stirring is started, the mixture is heated to 60 ℃, then 1.52g (28.6 mmol) of acrylonitrile is added dropwise, after the acrylonitrile is added dropwise, the reaction is continued for 6 hours, after hot filtration, the temperature is reduced, and a rotary evaporator is used for evaporating the solvent, so that the 3-N-methyl-N-decaalkyl glucose amide oxypropionitrile is obtained.
150mL of cyclohexane, 10g of 3-N-methyl-N-decaalkyl glucamide oxypropionitrile, 0.9g of Raney-Ni catalyst and an inhibitor NH are added into a high-pressure reaction kettle 3 ·H 2 O0.5 g with N 2 3 substitutions. Stirring is started, after the temperature is raised to 75 ℃, H is introduced into the kettle 2 (pressure is 2 MPa), after the reaction is carried out for 6 hours, discharging is carried out, after hot filtration, a rotary evaporator evaporates the solvent, and the product 3-N-methyl-N-decanyl glucose amidoxypropylamine is obtained, and the content is measured to be 93 percent.
Experimental example 1:
the results of the biodegradability test of the samples prepared according to the above examples according to the national standard GB/T15818-2018 (surfactant biodegradability test method) are shown in the following table:
experimental example 2:
and detecting the mineral flotation effect of the prepared sample by taking quartz ore as a sample. The specific flotation experimental method comprises the following steps: the single mineral flotation experiment was performed on an XFG hanging-cell flotation machine with a spindle speed of 1230r/min. 3g of minerals are weighed each time and put into a 40mL flotation tank, 30mL distilled water is added, a certain amount of flotation agent solution is added after size mixing lmin, stirring is carried out for 3min, and flotation is carried out for 5min. And respectively drying and weighing the foam product and the product in the tank, and calculating the recovery rate.
According to the above method, the results of the mineral flotation performance test for the samples prepared in the above examples are shown in the following table:

Claims (10)

1. a glycosyl propylamine compound structure is shown in a structural general formula (I),
，
wherein m is selected from 8-14.
2. The glycosylpropylamine of claim 1, selected from the following compounds:
3-N-methyl-N-dodecyl-glucamide oxypropylamine,
3-N-methyl-N-decanyl glucamide oxypropylamine.
3. The process for the preparation of glycosylpropylamines according to claim 1, which comprises the following steps:
，
wherein m is selected from 8-14.
4. The process for the preparation of glycosylpropylamines according to claim 1, comprising the following reaction steps:
step one: cyclohexane, alkyl glycosyl compound and solid base catalyst according to the mass ratio (8-15): 1: (0.5-5 mill) adding into a container, then slowly adding acrylonitrile, reacting for 5-9h, thermally filtering, cooling, and evaporating solvent to obtain 3-alkyl glycosyl oxypropionitrile;
step two: adding cyclohexane, 3-alkyl glycosyl oxypropionitrile, raney-Ni catalyst and inhibitor NH into a high-pressure reaction vessel 3 ·H 2 O, N 2 Replacing, stirring, heating to 60-90 ℃, and introducing H into the high-pressure reaction vessel 2 After 5-9h, discharging, hot filtering, and distilling under reduced pressure to remove the solvent to obtain the 3-alkyl glycosyloxypropylamine.
5. The method for preparing glycosyl propylamine compound according to claim 4, which is characterized in that: the alkyl glycosyl compound is N-methyl-N-alkyl glucamide.
6. The method for preparing glycosyl propylamine compound according to claim 4, which is characterized in that: the solid base catalyst is one or two of sodium hydroxide and potassium hydroxide.
7. The method for preparing glycosyl propylamine compound according to claim 4, which is characterized in that: the molar ratio of acrylonitrile to alkyl glycosyl compound is 0.9-1.3.
8. The method for preparing glycosyl propylamine compound according to claim 4, which is characterized in that: the mass ratio of cyclohexane to 3-alkyl glycosyloxy propionitrile is 8-13:1.
9. the method for preparing glycosyl propylamine compound according to claim 4, which is characterized in that: raney-Ni catalyst is used in an amount of 2-12wt% based on the mass of 3-alkyl glycosyl oxypropionitrile.
10. Use of a glycosylpropylamine compound according to claim 1 as a flotation agent.
CN202110907789.9A 2021-08-09 2021-08-09 Glycosyl propylamine compound, preparation method and application thereof as flotation agent Active CN113603608B (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007101575A1 (en) * 2006-03-09 2007-09-13 Clariant International Ltd Flotation reagent for silicates
CN104803862A (en) * 2015-04-03 2015-07-29 广东省石油化工研究院 Synthetic method of ether amine flotation agent

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007101575A1 (en) * 2006-03-09 2007-09-13 Clariant International Ltd Flotation reagent for silicates
CN104803862A (en) * 2015-04-03 2015-07-29 广东省石油化工研究院 Synthetic method of ether amine flotation agent

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