CN116903490A - 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 PDFInfo
- Publication number
- CN116903490A CN116903490A CN202310776193.9A CN202310776193A CN116903490A CN 116903490 A CN116903490 A CN 116903490A CN 202310776193 A CN202310776193 A CN 202310776193A CN 116903490 A CN116903490 A CN 116903490A
- Authority
- CN
- China
- Prior art keywords
- glycosyl
- alkyl
- propylamine
- compound
- compound according
- 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.)
- Pending
Links
- -1 Glycosyl propylamine compound Chemical class 0.000 title claims abstract description 53
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 239000008396 flotation agent Substances 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 125000003147 glycosyl group Chemical group 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 16
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 15
- 238000001914 filtration Methods 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 13
- 238000001704 evaporation Methods 0.000 claims description 12
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 238000007599 discharging Methods 0.000 claims description 7
- 239000003112 inhibitor Substances 0.000 claims description 7
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 229930182470 glycoside Natural products 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 230000001988 toxicity Effects 0.000 abstract description 4
- 231100000419 toxicity Toxicity 0.000 abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 14
- 239000011707 mineral Substances 0.000 description 14
- 238000005188 flotation Methods 0.000 description 10
- 238000011161 development Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QLDHWVVRQCGZLE-UHFFFAOYSA-N acetyl cyanide Chemical compound CC(=O)C#N QLDHWVVRQCGZLE-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 231100000209 biodegradability test Toxicity 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229930182474 N-glycoside Natural products 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- JQJCSZOEVBFDKO-UHFFFAOYSA-N lead zinc Chemical compound [Zn].[Pb] JQJCSZOEVBFDKO-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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
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:
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 ℃, and the preferable reaction temperature is: 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: cyclohexane, 3-alkyl glycosyl oxygen radical propionitrile, raney-Ni catalyst and inhibitor NH3.H2O are added into a high pressure reaction vessel, N2 is used for replacement, stirring is carried out, after the temperature is raised to 60-90 ℃, H2 is introduced into the high pressure reaction vessel, after the reaction is carried out for 5-9H, discharging is carried out, and after hot filtration, the solvent is removed by reduced pressure distillation, thus obtaining the 3-alkyl glycosyl oxygen radical propylamine.
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 1.5-4.0 MPa, 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 was charged 150mL of cyclohexane, 10 g (25 mmol) of hexadecyl glycoside and 0.01 g of sodium hydroxide. After the raw materials are added, stirring is started, the mixture is heated to 60 ℃, then acrylonitrile 1.33 g (25 mmol) is added dropwise, after the acrylonitrile is added dropwise, the reaction is continued to 9h, after hot filtration, the temperature is reduced, and a rotary evaporator is used for evaporating the solvent, so that 3-hexadecyl glycosidoxy propionitrile is obtained.
150mL of cyclohexane, 10 g of 3-hexadecyl glycosidoxy propionitrile, 0.5. 0.5 g 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 reaction 5. 5 h, discharging, hot filtering, evaporating the solvent by a rotary evaporator to obtain the product 3-hexadecyl glycosidoxy propylamine, wherein the content is measured to be 91%.
Example 2: 3-N-methyl-N-dodecyl-glucamide oxypropylamine
In a 250ml flask were charged 150mL of cyclohexane, 10. 10 g (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 acrylonitrile 1.41 and g (26.5 mmol) are added dropwise, after the acrylonitrile is added dropwise, the reaction is continued for 7 h, 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, 10 g of 3-N-methyl-N-dodecyl glucose amidoxypropionitrile, 0.7 g of Raney-Ni catalyst and g of inhibitor NH are added into a high-pressure reaction kettle 3 ·H 2 O0.5 g, 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 7. 7 h, 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 was charged 150mL of cyclohexane, 10 g (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 acrylonitrile 1.72 and g (32.5 mmol) are added dropwise, after the acrylonitrile is added dropwise, the mixture is reacted for 5 h, 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, 10 g of 3-octaalkyl glucose amidoxypropionitrile, raney-Ni catalyst 1g and inhibitor NH are added into a high-pressure reaction kettle 3 ·H 2 O0.5 g, 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 3-octaalkyl glucose amide oxyPropylamine was measured at 90%.
Example 4: 3-dodecyl glycosidoxy propylamine
In a 250mL flask was charged 150mL of cyclohexane, 10 g (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 acrylonitrile 1.50 g (28.3 mmol) is added dropwise, after the acrylonitrile is added dropwise, the reaction is continued for 8 h, after hot filtration, the temperature is reduced, and a rotary evaporator is used for evaporating the solvent, so that 3-dodecyl glycosidoxy propionitrile is obtained.
150mL of cyclohexane, 10 g of 3-dodecyl glycosidoxy propionitrile, 0.8 g of Raney-Ni catalyst g and inhibitor NH are added into a high-pressure reaction kettle 3 ·H 2 O0.5 g, 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 8. 8 h, 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, 10 g (28.6 mmol) of N-methyl-N-deca-nylamide and 0.06g of sodium hydroxide. After the raw materials are added, stirring is started, the mixture is heated to 60 ℃, then acrylonitrile 1.52 g (28.6 mmol) is added dropwise, after the acrylonitrile is added dropwise, the reaction is continued for 6 h, after hot filtration, the temperature is reduced, and a rotary evaporator is used for evaporating the solvent, so that 3-N-methyl-N-decanyl glucose amide oxypropionitrile is obtained.
150mL of cyclohexane, 10 g of 3-N-methyl-N-decaalkyl glucose amidoxypropionitrile, 0.9 of Raney-Ni catalyst and g of inhibitor NH are added into a high-pressure reaction kettle 3 ·H 2 O0.5 g, N 2 3 substitutions. Stirring and heatingAfter the temperature reaches 75 ℃, H is introduced into the kettle 2 (pressure is 2 MPa), after reaction 6 h, discharging, hot filtering, evaporating the solvent by a rotary evaporator to obtain the product 3-N-methyl-N-decanyl glucose amidoxypropylamine, wherein the content is measured to be 93%.
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. Each time, 3 g minerals are weighed 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 5 min. 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:
| examples | Example 1 | Example 2 | Example 3 | Example 4 | Examples5 |
| Recovery/% | 96 | 98 | 95 | 96 | 97 |
Claims (10)
1. A glycosyl propylamine compound structure is shown in a structural general formula (II),
，
wherein m is selected from 8-14, n is selected from 7-15.
2. The glycosylpropylamine of claim 1, selected from the following compounds:
3-hexadecyl glycosidoxy-propylamine,
3-N-methyl-N-dodecyl-glucamide oxypropylamine,
3-octylamidooxypropylamine,
3-dodecylglycosidoxy-propylamine,
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, n is selected from 7-15.
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: cyclohexane, 3-alkyl glycosyl oxygen radical propionitrile, raney-Ni catalyst and inhibitor NH3.H2O are added into a high pressure reaction vessel, N2 is used for replacement, stirring is carried out, after the temperature is raised to 60-90 ℃, H2 is introduced into the high pressure reaction vessel, after the reaction is carried out for 5-9H, discharging is carried out, and after hot filtration, the solvent is removed by reduced pressure distillation, thus obtaining the 3-alkyl glycosyl oxygen radical propylamine.
5. The method for preparing glycosyl propylamine compound according to claim 4, which is characterized in that: the alkyl glycosyl compound is one or a combination of a plurality of N-methyl-N-alkyl glucamide, alkyl glucamide or alkyl glycoside.
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, preferably 1.0-1.1.
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, preferably 9-12:1.
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%, preferably 2-8% based on the mass of 3-alkyl glycosyloxy propionitrile.
10. Use of a glycosylpropylamine compound according to claim 1 as a flotation agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310776193.9A CN116903490A (en) | 2021-08-09 | 2021-08-09 | Glycosyl propylamine compound, preparation method and application thereof as flotation agent |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310776193.9A CN116903490A (en) | 2021-08-09 | 2021-08-09 | Glycosyl propylamine compound, preparation method and application thereof as flotation agent |
| CN202110907789.9A CN113603608B (en) | 2021-08-09 | 2021-08-09 | Glycosyl propylamine compound, preparation method and application thereof as flotation agent |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110907789.9A Division CN113603608B (en) | 2021-08-09 | 2021-08-09 | Glycosyl propylamine compound, preparation method and application thereof as flotation agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116903490A true CN116903490A (en) | 2023-10-20 |
Family
ID=78339970
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110907789.9A Active CN113603608B (en) | 2021-08-09 | 2021-08-09 | Glycosyl propylamine compound, preparation method and application thereof as flotation agent |
| CN202310776193.9A Pending CN116903490A (en) | 2021-08-09 | 2021-08-09 | Glycosyl propylamine compound, preparation method and application thereof as flotation agent |
| CN202310776194.3A Pending CN116903685A (en) | 2021-08-09 | 2021-08-09 | Glycosyl propylamine compound, preparation method and application thereof as flotation agent |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110907789.9A Active CN113603608B (en) | 2021-08-09 | 2021-08-09 | Glycosyl propylamine compound, preparation method and application thereof as flotation agent |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310776194.3A Pending CN116903685A (en) | 2021-08-09 | 2021-08-09 | Glycosyl propylamine compound, preparation method and application thereof as flotation agent |
Country Status (1)
| Country | Link |
|---|---|
| CN (3) | CN113603608B (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006010939A1 (en) * | 2006-03-09 | 2007-09-13 | Clariant International Limited | 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 |
-
2021
- 2021-08-09 CN CN202110907789.9A patent/CN113603608B/en active Active
- 2021-08-09 CN CN202310776193.9A patent/CN116903490A/en active Pending
- 2021-08-09 CN CN202310776194.3A patent/CN116903685A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN116903685A (en) | 2023-10-20 |
| CN113603608A (en) | 2021-11-05 |
| CN113603608B (en) | 2023-11-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108745197B (en) | Easily degradable gemini quaternary ammonium salt and preparation method thereof | |
| AU2012242041A1 (en) | Amine and diamine compounds and their use for inverse froth flotation of silicate from iron ore | |
| CN103084276B (en) | Preparation method of plant fatty acid diethanolamide ester soap compound collecting agent | |
| US10815337B2 (en) | Ether amine compounds and use thereof as flotation collector | |
| CN110357793A (en) | A kind of carboxylate oximation process | |
| US20140021104A1 (en) | Amine and diamine compounds and their use for inverse froth flotation of silicate from iron ore | |
| CN101475498B (en) | Preparation method of 3-dehydroabietylamine-2-hydroxypropyl trimethyl ammonium chloride | |
| CN110669019A (en) | Melamine derivative corrosion inhibitor and preparation method and application thereof | |
| CN108558679B (en) | Synthetic method of Parylene A precursor | |
| CN113603608B (en) | Glycosyl propylamine compound, preparation method and application thereof as flotation agent | |
| EP2524909B1 (en) | Preparation method of 4-aminomethylbenzoic acid | |
| CN113651709A (en) | Fatty amide propyl dimethyl tertiary amine and preparation method and application thereof | |
| CN103664652A (en) | Synthesis method of N, N, N', N'-tetrakis (2-hydroxyethyl)-ethylenediamine (THEEDA) | |
| CN108752217B (en) | Synthesis method of dolutegravir key intermediate 2, 4-difluorobenzylamine | |
| CN112175597A (en) | Well-flushing foam water shutoff agent and preparation method thereof | |
| CN101928222A (en) | Synthesis method of N, N, N', N'-tetraisopropyl ethylene diamine | |
| CN104888968B (en) | Preparation method of amphoteric collector for reverse flotation of phosphorite | |
| CN110813186A (en) | Quaternary ammonium salt surfactant based on kitchen waste oil and preparation method thereof | |
| CN109679631B (en) | Foam drainage agent composition for ultra-deep gas well, preparation method and application | |
| CN107674665B (en) | Foam drainage agent composition for ultra-deep gas well and preparation method and application thereof | |
| US2786869A (en) | Nu-trialkylcarbinyl-nu-(hydroxyethyl-polyoxyethyl) glycines | |
| CN103626721B (en) | A kind of method of coproduction N-methylmorpholine and two (2-dimethylaminoethyl) ether | |
| CN113648926A (en) | Cardanol cyclic carbonate ether nonionic surfactant and preparation method thereof | |
| CN113200872A (en) | Method for preparing 1, 8-p-menthane diamine by one-step method | |
| CN107056640B (en) | One kind is low to steep double salt-free imidazoline surfactants of alkyl and its synthetic method |
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 |