CN106432710B - Polyethers gucosamine and preparation method and the purposes as gasoline cleaning agent host agent - Google Patents

Polyethers gucosamine and preparation method and the purposes as gasoline cleaning agent host agent Download PDF

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CN106432710B
CN106432710B CN201610781248.5A CN201610781248A CN106432710B CN 106432710 B CN106432710 B CN 106432710B CN 201610781248 A CN201610781248 A CN 201610781248A CN 106432710 B CN106432710 B CN 106432710B
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gucosamine
polyethers
polyethenoxy ether
benzenyls
chloro
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CN106432710A (en
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钟亮
陈雪
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TIANJIN YUETAI PETRO-CHEMICAL TECHNOLOGY Co Ltd
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TIANJIN YUETAI PETRO-CHEMICAL TECHNOLOGY Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
    • C08G65/33396—Polymers modified by chemical after-treatment with organic compounds containing nitrogen having oxygen in addition to nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/234—Macromolecular compounds
    • C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
    • C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C)
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G2650/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterized by the type of post-polymerisation functionalisation
    • C08G2650/04—End-capping
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2270/00—Specifically adapted fuels
    • C10L2270/02—Specifically adapted fuels for internal combustion engines
    • C10L2270/023—Specifically adapted fuels for internal combustion engines for gasoline engines

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Detergent Compositions (AREA)

Abstract

Purposes the invention discloses polyethers gucosamine and preparation method and as gasoline cleaning agent host agent, polyethers gucosamine are shown in Formulas I：

Description

Polyethers gucosamine and preparation method and the purposes as gasoline cleaning agent host agent
Technical field
The present invention relates to a kind of polyethers gucosamines as gasoline cleaning agent host agent, further relate to the system of polyethers gucosamine Preparation Method.
Background technology
Gasoline incomplete combustion in engine can form hard and viscous carbon distribution, so as to influence automobile driving speed and gasoline Efficiency of combustion, and environmental pollution can be caused, shorten service life of aeroengine.It is added in motor petrol at present effective peace and quiet Agent is the effective ways for improving automobile engine performance, controlling pollutant emission.
Marketable gasolines detersive host agent mainly has polyisobutylene amine and polyetheramine, generally using amino as polar group. Polar group can started by closely being combined in the form of single-point or multiple spot the effects that hydrogen bond, Van der Waals force, acid-base neutralization On machine sedimentary particle surface, weaken deposit and the suction-operated of parts metal surface, thus the deposition generated Object is peeled off from metal surface.
Polyetheramine has good dispersion, washing, solubilising and deacidification as gasoline cleaning agent host agent, therefore obtains It is widely applied.Polyetheramine is a kind of polyoxyalkylene hydrocarbon compound blocked by primary amine groups or secondary amine, conventional synthesis process Mostly using polyether polyol as raw material, then polyetheramine obtained by amination.The difference for the alkyl radical structure that is connected according to end amido, polyethers Amine can be divided into aromatic series and aliphatic poly ether amines (CN200710191281.3, CN201010517664.7), according to amino group The middle substituted number of hydrogen atom is divided into as primary amine groups, secondary amine and tertiary amine groups polyetheramine, aminated compounds can be monoamine or Polyamines.These aminated compounds generally all have certain toxicity, and production process can cause certain environmental pollution, may after burning Indefinite noxious material can be generated.
Non-toxic to humans, easily biological-degradable, the green surfactant small to ecological environmental pollution are developed in recent years It is a development trend of current fine chemicals.Gucosamine is made using the extensive natural materials chitin in source as raw material. Glucose amine surfactants have good emulsibility, surface-active and biocompatibility, are a kind of environmental-friendly tables Face activating agent will not generate noxious material after burning.In addition gucosamine adsorption capacity is strong, has especially for metal ion Absorption sequestering power well goes carbon remover ability using what this characteristic can improve polyetheramine.
Invention content
The purpose of the present invention is overcome the deficiencies of the prior art and provide a kind of polyethers gucosamine.
Second object of the present invention is to provide a kind of preparation method of polyethers gucosamine.
Third object of the present invention is to provide a kind of purposes of polyethers gucosamine as gasoline cleaning agent host agent.
Technical scheme of the present invention is summarized as follows：
A kind of polyethers gucosamine, shown in Formulas I：
Wherein：N is the natural number of one of 10-21.
A kind of preparation method of polyethers gucosamine, includes the following steps：
(1) amido protecting of gucosamine：
Aminoglucose hydrochloride (II) reacts generation N- benzylideneaminos glucose (III) with benzaldehyde；
(2) preparation of chloro polyethers：
Polyethenoxy ether (IV) and epoxychloropropane (V) reaction generation chloro polyethenoxy ether (VI)；
(3) N- benzylideneaminos glucose and chloro polyethenoxy ether react：
In the reactor, in proportion, 10-20g chloros polyethenoxy ether (VI) is added in, is heated to 70-110 DEG C, is added in solid Body sodium hydroxide or solid potassium hydroxide are catalyst, add in N- benzylideneaminos glucose (III), react 3-6 hours, remove Water layer is removed, is filtered to remove unreacted hydrogen sodium oxide molybdena or oxygen potassium oxide, N- benzylideneaminos glucose (III) uses volumetric concentration Ethanol water for 5%-20% washs, and separates organic layer, obtains O-6- polyethenoxy ether-N- benzylideneamino glucose (VII)；
The solid sodium hydroxide or solid potassium hydroxide, N- benzylideneaminos glucose (III) and chloro polyoxy third The molar ratio of alkene ether (VI) is (1-3):(1.1-1.3):1；
(4) reduction of amino
In proportion, 10-20g O-6- polyethenoxy ether-N- benzylideneaminos glucose (VII) is added in into 200- In hydrochloric acid-ethanol solution of 400ml0.3-0.5M, 12-24h is stirred to react, adjusts pH=7-8, water layer is removed and separates organic layer, The ethanol water for being 5%-20% with volumetric concentration washs, and revolving obtains polyethers gucosamine (I), reaction equation is：
Wherein：N is the natural number of one of 10-21.
A kind of purposes of polyethers gucosamine as gasoline cleaning agent host agent.
Polyethers gucosamine prepared by the present invention, there are one amino and multiple hydroxyls, there is very strong absorption carbon distribution effect, Under the collective effect of polyethers has, be conducive to the package removing to soot particles；Gucosamine has metal surface stronger absorption to make With being easily formed more firm cleaning protective film；As a result of amido protecting, reaction process high selectivity, by-product is few； Reaction condition is mild, easily operated；Gucosamine is as biological products, and environmental pollution is small, and prepared polyethers gucosamine is also The good surfactant of biocompatibility can be used as to be applied to other aspects.
Specific embodiment
The embodiment that the present invention is more optimized by following reaction condition, is described in further detail, but is carried out in the technology of example Appearance is illustrative, should not limit to protection scope of the present invention according to this.
Embodiment 1
A kind of preparation method of polyethers gucosamine, includes the following steps：
(1) amido protecting of gucosamine (reaction document has been reported)：
In 0 DEG C of ice-water bath, 2gNaOH is dissolved in 100ml distilled water, then adds in 10g aminoglucose hydrochlorides (II) (46mmol) dissolves, and adds in 6g (51mmol) benzaldehyde, reacts 1h, is filtered, washed, dries, obtain white solid N- benzene Methene amido glucose (III) 12g；
(2) preparation of chloro polyethers (reaction document has been reported)：
Polyethers (n=17) 20g (20mmol) that molecular weight is 1000 is added in reactor, 70 DEG C is warming up to, adds in 0.04g butters of tin (catalyst amount is the 1/500 of polyethers), stir lOmin, add 2.22g epoxychloropropane (24mmol) is warming up to 100 DEG C, reacts 2 hours, after reaction wash reactant, separate organic layer, and then organic layer revolves Steam to obtain chloro polyethenoxy ether (VI) 21g；
(3) N- benzylideneaminos glucose and chloro polyethenoxy ether react：
In the reactor, 20g chloros polyethenoxy ether (VI) (18.3mmol) is added in, is heated to 90 DEG C, 1.46g is added in and consolidates Body sodium hydroxide (36.6mmol) is catalyst, and it is small to react 4 for 5.76gN- benzylideneaminos glucose (III) (22mmol) When, water layer is removed, is filtered to remove unreacted hydrogen sodium oxide molybdena, N- benzylideneaminos glucose (III) is 10% with volumetric concentration Ethanol water washing, separate organic layer, obtain O-6- polyethenoxy ether-N- benzylideneaminos glucose (VII) 19.3g；IR (KBr, v/cm-1)：3510(vOH), 3004 (vCOC), 2992 (vCH), 1650 (vN=C), l593 (vC=C), 1454 (vCH2), l340 (vCH), 1260 (vOH), l070 ((vCOC), l015 (vCOC), 870 (vCOC), 759,691 (vC=CH)；
Mole of the solid sodium hydroxide, N- benzylideneaminos glucose (III) and chloro polyethenoxy ether (VI) Than being 1:2:1.2；
(4) reduction of amino
10g O-6- polyethenoxy ether-N- benzylideneaminos glucose (VII) (7.6mmol) is added in into 300ml 0.4M Hydrochloric acid-ethanol solution in, be stirred to react 18h, add in sodium hydroxide and adjust pH=8, remove water layer and separate organic layer, use volume A concentration of 10% ethanol water washing, revolving obtain polyethers gucosamine (I) 8.6g.Product point is understood through chemical analysis Son amount 1255, amine value 0.7mmol/g, chloride ion content is less than 1%.IR (KBr, v/cm-1)：3500(vOH), 3000 (vCOC), 2990(vCH), 1520 (vCN), 1440 (vCH2), l320 (vCH), 1250 (vOH), l030 ((vCOC), 850 (vCOC)。
Wherein：N is 17.
Embodiment 2
A kind of preparation method of polyethers gucosamine, includes the following steps：
(1) amido protecting of gucosamine：
With 1 step of embodiment (1)
(2) preparation of chloro polyethers：
Polyethers (n=10) 12g (20mmol) that molecular weight is 600 is added in reactor, 70 DEG C is warming up to, adds in 0.04g butters of tin (catalyst amount is the 1/500 of polyethers), stir lOmin, add 2.04g epoxychloropropane (22mmol) is warming up to 100 DEG C, reacts 2 hours, after reaction wash reactant, separate organic layer, and then organic layer revolves Steam to obtain chloro polyethenoxy ether (VI) 13g；
(3) N- benzylideneaminos glucose and chloro polyethenoxy ether react：
In the reactor, 10g chloros polyethenoxy ether (VI) (14.5mmol) is added in, is heated to 70 DEG C, 0.58g is added in and consolidates Body sodium hydroxide is catalyst (14.5mmol), adds in 4.18gN- benzylideneaminos glucose (III) (15.95mmol).Instead It answers 3 hours, removes water layer, be filtered to remove unreacted hydrogen sodium oxide molybdena, N- benzylideneaminos glucose (III) uses volumetric concentration Ethanol water for 5% washs, and separates organic layer, obtains O-6- polyethenoxy ether-N- benzylideneaminos glucose (VII) 10.5g；
Mole of the solid sodium hydroxide, N- benzylideneaminos glucose (III) and chloro polyethenoxy ether (VI) Than being 1:1.1:1；
(4) reduction of amino
10g O-6- polyethenoxy ether-N- benzylideneaminos glucose (VII) is added in hydrochloric acid-second of 200ml 0.3M In alcoholic solution, 12h is stirred to react, adjusts pH=7, water layer is removed and separates organic layer, with the ethanol water that volumetric concentration is 5% Washing, revolving, obtains polyethers gucosamine (I) 8.3g.
Embodiment 3
A kind of preparation method of polyethers gucosamine, includes the following steps：
(1) amido protecting of gucosamine：
With 1 step of embodiment (1)
(2) preparation of chloro polyethers：
Polyethers (n=21) 24g (20mmol) that molecular weight is 1200 is added in reactor, 70 DEG C is warming up to, adds in 0.04g butters of tin (catalyst amount is the 1/500 of polyethers), stir lOmin, add 2.4g epoxychloropropane (26mmol) is warming up to 100 DEG C, reacts 2 hours, after reaction wash reactant, separate organic layer, and then organic layer revolves Steam to obtain chloro polyethenoxy ether (VI) 24.5g；
(3) N- benzylideneaminos glucose and chloro polyethenoxy ether react：
In the reactor, 20g chloros polyethenoxy ether (VI) (15.5mmol) is added in, is heated to 110 DEG C, adds in 1.86g Solid potassium hydroxide is catalyst (46.5mmol), adds in 5.29g N- benzylideneaminos glucose (III) (15.5mmol) (20.2mmol) reacts 6 hours, removes water layer, be filtered to remove unreacted oxygen potassium oxide, N- benzylideneamino glucose (III), it is washed with the ethanol water that volumetric concentration is 20%, separates organic layer, obtain O-6- polyethenoxy ether-N- benzene methylenes Base Glucosamine (VII) 18.9g；
The solid sodium hydroxide or solid potassium hydroxide, N- benzylideneaminos glucose (III) and chloro polyoxy third The molar ratio of alkene ether (VI) is 3:1.3:1；
(4) reduction of amino
20g O-6- polyethenoxy ether-N- benzylideneaminos glucose (VII) is added in hydrochloric acid-second of 400ml 0.5M It in alcoholic solution, is stirred to react for 24 hours, adjusts pH=8, remove water layer and separate organic layer, it is water-soluble with the ethyl alcohol that volumetric concentration is 20% Liquid washs, and revolving obtains polyethers gucosamine (I) 17.2g,
Embodiment 4
Gasoline cleaning agent is made by mass percentage of following raw materials：
The polyethers gucosamine (I) 60% that respectively prepared by Example 1,2,3 in three parts of samples, then all adds antioxygen Agent (T501) 2%, antirust agent (commercially available T703) 2%, corrosion inhibitor (commercially available T551) 1%, cosolvent (methanol) 35% mix Close uniform gasoline cleaning agent 1, gasoline cleaning agent 2 and gasoline cleaning agent 3.
The gasoline cleaning agent modulated is added to according to 300ppm amounts in commercially available 92# gasoline, is advised according to GB/T19230.4 Deposit generation rate of descent on fixed experimental method simulated automotive intake valve, according to high temperature thermogravimetric analysis, simulated automotive starts The residual rate of 500 DEG C of machine combustion chamber or more.After tested, simulation inlet valve deposits rate of descent reaches, and is warmed with 500 DEG C or more high Weight analysis, simulated combustion room deposit increment variation, declines than presently commercially available detersive, and experimental result is shown in Table 1.
Table 1
Antioxidant is selected from the mixture of one or more of commercially available T501, T502, T531, T534；
Antirust agent is selected from the mixture of one or more of commercially available T703, T706, T747, SP-80, SP-85 composition；
Corrosion inhibitor is selected from the mixture of one or both of commercially available T551, T561 composition；
Cosolvent is selected from one or more of commercially available aromatic naphtha, solvent naphtha, methanol, ethyl alcohol, butanol, isooctanol composition Mixture.

Claims (3)

1. a kind of polyethers gucosamine, it is characterized in that shown in Formulas I：
Wherein：N is the natural number of one of 10-21.
2. a kind of preparation method of polyethers gucosamine described in claim 1, it is characterized in that including the following steps：
(1) amido protecting of gucosamine：
Aminoglucose hydrochloride (II) reacts generation N- benzenyls Glucosamine (III) with benzaldehyde；
(2) preparation of chloro polyethers：
Polyethenoxy ether (IV) and epoxychloropropane (V) reaction generation chloro polyethenoxy ether (VI)；
(3) N- benzenyls Glucosamine and chloro polyethenoxy ether react：
In the reactor, in proportion, 10-20g chloros polyethenoxy ether (VI) is added in, is heated to 70-110 DEG C, adds in solid hydrogen Sodium oxide molybdena or solid potassium hydroxide are catalyst, add in N- benzenyls Glucosamine (III), are reacted 3-6 hours, remove water Layer, is filtered to remove unreacted hydrogen sodium oxide molybdena or potassium hydroxide, N- benzenyls Glucosamine (III) is with volumetric concentration The ethanol water washing of 5%-20%, separates organic layer, obtains O-6- polyethenoxy ether-N- benzenyl Glucosamines (VII)；
The solid sodium hydroxide or solid potassium hydroxide, N- benzenyls Glucosamine (III) and chloro polyethenoxy ether (VI) molar ratio is (1-3):(1.1-1.3):1；
(4) reduction of amino
In proportion, 10-20g O-6- polyethenoxy ether-N- benzenyls Glucosamines (VII) are added in into 200-400ml0.3- In hydrochloric acid-ethanol solution of 0.5M, 12-24h is stirred to react, adjusts pH=7-8, water layer is removed and separates organic layer, it is dense with volume The ethanol water washing for 5%-20% is spent, revolving obtains polyethers gucosamine (I), reaction equation is：
Wherein：N is the natural number of one of 10-21.
3. a kind of purposes of the polyethers gucosamine described in claim 1 as gasoline cleaning agent host agent.
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WO2013050487A1 (en) * 2011-10-05 2013-04-11 Arkema France Polyhydroxyl - substituted amino compounds, polymers containing, and their use
CN103710060A (en) * 2013-12-25 2014-04-09 济南开发区星火科学技术研究院 Preparation method for compound diesel cleansing agent
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CN105647600A (en) * 2016-02-01 2016-06-08 陕西延长石油能源科技有限公司 Composite high-cleanness fuel oil additive and preparation method thereof

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