CN105367802A - Polyether modified phenyl hydrogen-containing silicone oil and preparation method thereof - Google Patents
Polyether modified phenyl hydrogen-containing silicone oil and preparation method thereof Download PDFInfo
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- CN105367802A CN105367802A CN201510816208.5A CN201510816208A CN105367802A CN 105367802 A CN105367802 A CN 105367802A CN 201510816208 A CN201510816208 A CN 201510816208A CN 105367802 A CN105367802 A CN 105367802A
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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Abstract
The invention relates to polyether modified phenyl hydrogen-containing silicone oil and a preparation method thereof. According to the invention, under nitrogen protection, an isopropyl alcohol solution of chloroplatinic acid, the phenyl hydrogen-containing silicone oil and polyether are added in a reaction vessel, the above components are subjected to a reaction for 7-10 hours at temperature of 100-130 DEG C to obtain the polyether modified phenyl hydrogen-containing silicone oil; wherein, a mol ratio of phenyl hydrogen-containing silicone oil to polyether is 1:(1-1.3). According to the invention, platinum is employed as a catalyst, the provided preparation method realizes good performance of the modified silicone oil, and the method for the hydrogen-containing silicone oil has the advantages of simple operation, low cost and high efficiency, a purpose of large-scale production requirement can be satisfied, the employed hydrogen-containing silicone oil can save preparation steps and can reach the purpose of enhancing thermostability of polysiloxane.
Description
Technical field
The present invention relates to the emulsion splitter of viscous crude on oil field, be specifically related to a kind of polyether-modified phenyl hydrogen-containing silicon oil and preparation method thereof.
Background technology
Organic silicon surfactant is a kind of novel surfactant along with organosilicon type material grows up, the traditional carbochain type tensio-active agent of Si-O-Si Link Ratio in its structural backbone has stronger hydrophobic interaction, and thus it has the excellent capillary ability of reduction.Wherein study the most extensively, product category maximum surely belong to organic silicon modified by polyether tensio-active agent, it is widely used in the fields such as cosmetics additive, urethane suds-stabilizing agent, fabric finishing agent, defoamer, emulsion splitter and coating.
The topmost synthetic method of polyether modified silicon oil utilizes the addition reaction of silicon with hydrogen between Si-H key and unsaturated double-bond, and the catalyzer used is the title complex of precious metal mostly, as platinum, rhodium, palladium, ruthenium etc.Siloxane-Oxyalkylene Copolymers is that raw material reacts by selecting to have compared with the polyethers of strongly hydrophilic and the strong polysiloxane of hydrophobicity, thus in polysiloxane molecule, introduce obtained polyethers one silicone copolymers of polyether segment, and then pass through the ratio of both adjustments, reach the tensio-active agent with certain HLB value, be used further to the breakdown of emulsion of crude oil on oil field.
Viscosity of Heavy Crude Oil is large and containing interface active agents such as a large amount of colloidal bitumens.Colloid, bituminous matter are the complex mixtures of the compound composition of configurations, and its molecule basic structure, centered by the condensed aromatic hydrocarbon that forms by multiple aromatic nucleus, connects some naphthenic rings, aromatic nucleus around.If synthesis has the emulsion splitter of aromatic group, it has on oil-water interfacial film and even in crude oil and well dissolves diffustivity, thus embodies the advantage that dewatering speed is fast, dehydration rate is high.Tan Guorong etc. compare the demulsification performance of the dissimilar polyether type demulsifying agent of different block, and result shows that diblock polyether demulsification agent dewatering is more excellent.If synthesis not only had a polymeric monomer of diblock polyethers containing aromatic structure, then by its common modification containing hydrogen silicone oil, then can synthesizing new thick oil demulsifier.
Chinese patent CN200610113793 reports that a kind of heavy crude reservoir is poly-drives rear Produced Liquid dehydration demulsifying agent and preparation method thereof, two kinds of tensio-active agents are prepared in this invention first respectively, then two kinds of tensio-active agents, N-ethylperfluoro octyl group sulphonamide Soxylat A 25-7 are placed in reactor successively, a kind of dry agent is obtained after reacting for some time at a certain temperature, finally this dry agent is placed in mixture still and slowly drips water, obtain heavy crude reservoir and gather repelling crude oil demulsifying agent for dehydration.Its breaking emulsion and dewatering effect is better than existing emulsion splitter, but there is complicated operation, the deficiency that material equipment cost is high.
Wang Ermeng, Guo Rui (Speciality Petrochemicals, 2014,31 (4): 5-8) with vinylformic acid and nonyl phenol polyoxyethylene polyoxypropylene ether for raw material, by the polyether ester surface-active macromonomer of esterification synthesis containing phenyl ring, diblock polyethers, then obtain by modified silicon oil the polysiloxane thick oil demulsifier that side chain contains aromatic ring structure, diblock polyethers.Though it is fast that this emulsion splitter reaches dewatering speed in the application of oil field breakdown of emulsion, the advantage that dehydration rate is high, this preparation process is complicated, and esterification condition is wayward, is not suitable for carrying out scale operation.
Summary of the invention
For overcoming the problems of the prior art, the object of the present invention is to provide a kind of polyether-modified phenyl hydrogen-containing silicon oil and preparation method thereof, the method adopts one kettle way, both operation steps was saved, also improve reaction efficiency, reduce production cost, be conducive to carrying out scale operation.
For achieving the above object, the present invention is realized by following technical proposals:
A kind of polyether-modified phenyl hydrogen-containing silicon oil, structural formula is as follows:
Wherein, R
1for-CH
3; R
3for-CH
2cH
2cH
2o (C
2h4O)
m(C
3h
6o)
nr
2, R
2for-H ,-CH
3,-C
2h
5or-C
3h
7; X, y, z is integer, and z is non-vanishing, and scope is 10 ~ 200; M, n are integer, and are 0 when m, n are different; M=0 ~ 40; N=0 ~ 30.
A preparation method for polyether-modified phenyl hydrogen-containing silicon oil, under nitrogen protection, adds in reactor by the aqueous isopropanol of Platinic chloride, phenyl hydrogen-containing silicon oil and polyethers, reacts 7 ~ 10h, obtain polyether-modified phenyl hydrogen-containing silicon oil at 100 ~ 130 DEG C; Wherein, the mol ratio of phenyl hydrogen-containing silicon oil, polyethers is 1:(1 ~ 1.3), the ratio of the quality of the aqueous isopropanol of Platinic chloride and phenyl hydrogen-containing silicon oil and polyethers total mass is (30 ~ 40) μ g:1g.
In described phenyl hydrogen-containing silicon oil, hydrogeneous mass percent is 0.1 ~ 0.5%, is 20 ~ 40% containing benzene mass percent, and viscosity is 10 ~ 30mpas, and refractive index is 1.50.
Described polyethers is allyl alcohol polyether, and structural formula is
Wherein, R
2for-H ,-CH
3,-C
2h
5or-C
3h
7; M=0 ~ 40; N=0 ~ 30; M, n are integer, and are 0 when m, n are different.
The mass concentration of the aqueous isopropanol of described Platinic chloride is 2%.
Compared with prior art, this technology has following useful technique effect:
The present invention adopts phenyl hydrogen-containing silicon oil to be raw material, route first telomerizes containing hydrogen silicone oil and drips styryl again and carry out modification compared to existing technology, have simple to operate and can the molecular weight distribution of effective control objectives product, obtain the good target product of performance, improve the purity of product.And phenyl hydrogen-containing silicon oil is than methyl-silicone oil or other modification containing hydrogen silicone oil, have better resistance to elevated temperatures, radiation resistance, lubricity and solubility property, working temperature is-50 DEG C ~ 250 DEG C.
The present invention adopts solventless method; and utilize nitrogen to do shielding gas; need to add a large amount of organic solvents in reaction process with prior art; react the complete post-processing step that also needs to remove solvent phase ratio; prior art makes the complicated process of preparation of organic modified polyorganosiloxane, cost higher and to environment, is unfavorable for large-scale industrial production.
Owing to being that main naturally occurring emulsifying agent exists mainly with bituminous matter, colloid in crude oil, bituminous matter material is made up of the aromatic condensed ring of complexity and side chain.Colloid also has similar chemical structure.Therefore according to the similar principle mixed, in emulsion splitter molecule, the demulsification that aryl can improve emulsion splitter is introduced.Polysiloxane thermostability is relevant with several factors, easily by the restriction of condition, and on its molecular chain, introduces the object that phenyl can reach raising polysiloxane thermostability.And the introducing of polyethers can increase its wetting ability in the present invention.Siloxane-Oxyalkylene Copolymers (i.e. phenyl hydrogen-containing silicon oil) has water-soluble and oil soluble concurrently, and be easy to regulate, this analog copolymer is all very stable in very wide pH value range, even if (reduction and bleaching) result of use is still good under high concentration basic condition.It had both had every excellent properties of traditional siloxane series products, as high-low temperature resistant, anti-aging, hydrophobic, electrical isolation, low surface tension etc., there is again the special propertys such as lubrication, soft effect, good spreadability and the emulsifying stability that polyether segment provides simultaneously, modified tensio-active agent is carried out to polyether modified siloxane again there is more excellent effect.This type of tensio-active agent has become a kind of silicone products that application quantity is maximum, kind is maximum.Therefore, the advantage both the present invention combines, utilizes polyether-modified phenyl hydrogen-containing silicon oil, obtains one and have better demulsification, and use range is wider, the tensio-active agent that condition is harsher.
The present invention directly adopts polyether-modified phenyl hydrogen-containing silicon oil, and raw material is simple, and becomes to produce cost low.This method utilizes the reaction principle of Si―H addition reaction to react, and principle is simple, mild condition, therefore easy to process, cost is low, be easy to industrialization.
Further, the present invention adopts the methyl blocking polyether in allyl alcohol polyether, other END CAPPED GROUP used compared to existing technology, because end position allyl group participates in Si―H addition reaction, the other end is the methyl of inertia, greatly reduces the generation of side reaction, is beneficial to the organosilicon product of synthesis special purpose.Due to terminal hydroxyl reactive hydrogen carried out hydrosilation reaction by methyl substituted time, eliminate the reaction of hydroxyl and si-h bond, significantly reduce the viscosity of product and add effective content, improve the quality of polyether modified silicon oil, package stability is better, is especially suitable for the composite of the product growing and exist in product the complex conditions such as hydrolysis those storage periods.
Accompanying drawing explanation
Fig. 1 is synthetic route chart of the present invention.
Fig. 2 is the infrared spectrogram of the product that the present invention obtains.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in further details, but is not limited to practical range of the present invention.
The invention provides a kind of polyether-modified phenyl hydrogen-containing silicon oil, its structural formula is as follows:
Wherein, R
1for-CH
3; R
3for-CH
2cH
2cH
2o (C
2h4O)
m(C
3h
6o)
nr
2, R
2for-H ,-CH
3,-C
2h
5or-C
3h
7; X, y, z is integer, and z is non-vanishing, and scope is 10 ~ 200; M, n are integer, and are 0 when m, n are different; M=0 ~ 40; N=0 ~ 30.
See Fig. 1; the preparation method of above-mentioned polyether-modified phenyl hydrogen-containing silicon oil is: add in reactor by phenyl hydrogen-containing silicon oil, polyethers and catalyzer (aqueous isopropanol of Platinic chloride); reactor hollow gas drive is walked and protective reaction system by logical nitrogen; stirring is warming up to 100 ~ 130 DEG C; 7 ~ 10h is reacted at 100 ~ 130 DEG C; after reaction terminates, be cooled to room temperature, obtain polyether-modified phenyl hydrogen-containing silicon oil.In Fig. 1, the value of x, y, z and m, n determines according to the viscosity of phenyl hydrogen-containing silicon oil and the molecular weight of material.
Further illustrate below by specific embodiment that the present invention will be described.
Phenyl hydrogen-containing silicon oil in embodiments of the invention is colourless transparent liquid, and hydrogeneous mass percent is 0.1 ~ 0.5%, is 20 ~ 40% containing benzene mass percent, and viscosity is 10 ~ 30mpas (25 DEG C), and refractive index is 1.50.
In embodiments of the invention, catalyzer is the aqueous isopropanol that mass concentration is the Platinic chloride of 2%, and the ratio of catalyzer and phenyl hydrogen-containing silicon oil and polyethers total mass is 30 ~ 40 μ g:1g
Embodiment 1
Under nitrogen protection; by 100g phenyl hydrogen-containing silicon oil, (hydrogeneous mass percent is 0.5%; be 20% containing benzene mass percent; viscosity is 25mpas), 750g allyl alcohol polyether and 0.0255g catalyzer; add in the 250mL four-hole bottle of band thermometer, agitator; be warming up to 100 DEG C under stirring, and react 7h at this temperature.Then, Temperature fall, to room temperature, obtains polyether-modified phenyl hydrogen-containing silicon oil.
Embodiment 2
Under nitrogen protection; by 100g phenyl hydrogen-containing silicon oil, (hydrogeneous mass percent is 0.5%; be 20% containing benzene mass percent; viscosity is 25mpas), 825g allyl alcohol polyether and 0.02775g catalyzer; add in the 250mL four-hole bottle of band thermometer, agitator; be warming up to 110 DEG C under stirring, and react 8h at this temperature.Then, Temperature fall, to room temperature, obtains polyether-modified phenyl hydrogen-containing silicon oil.
Embodiment 3
Under nitrogen protection; by 100g phenyl hydrogen-containing silicon oil, (hydrogeneous mass percent is 0.5%; be 20% containing benzene mass percent; viscosity is 25mpas), 900g allyl alcohol polyether and 0.03g catalyzer; add in the 250mL four-hole bottle of band thermometer, agitator; be warming up to 120 DEG C under stirring, and react 9h at this temperature.Then, Temperature fall, to room temperature, obtains polyether-modified phenyl hydrogen-containing silicon oil.
Embodiment 4
Under nitrogen protection; by 100g phenyl hydrogen-containing silicon oil, (hydrogeneous mass percent is 0.5%; be 20% containing benzene mass percent; viscosity is 25mpas), 975g allyl alcohol polyether and 0.03225g catalyzer; add in the 250mL four-hole bottle of band thermometer, agitator; be warming up to 130 DEG C under stirring, and react 10h at this temperature.Then, Temperature fall, to room temperature, obtains polyether-modified phenyl hydrogen-containing silicon oil.
Embodiment 5
A kind of preparation method of polyether-modified phenyl hydrogen-containing silicon oil, under nitrogen protection, by phenyl hydrogen-containing silicon oil, (in phenyl hydrogen-containing silicon oil, hydrogeneous mass percent is 0.1%, be 30% containing benzene mass percent, viscosity is 15mpas, and refractive index is 1.50) and catalyzer add in reactor, stirring is warming up to 105 DEG C, and after reacting 10h at this temperature, naturally reduce temperature of reaction to room temperature, obtain polyether-modified phenyl hydrogen-containing silicon oil; Wherein, the mol ratio of phenyl hydrogen-containing silicon oil and polyethers is 1:1, and the ratio of the quality of catalyzer and phenyl hydrogen-containing silicon oil and vinyl carbinol total mass is 30 μ g:1g, the aqueous isopropanol of catalyzer to be mass concentration the be Platinic chloride of 2%.
Embodiment 6
A kind of preparation method of polyether-modified phenyl hydrogen-containing silicon oil, under nitrogen protection, by phenyl hydrogen-containing silicon oil, (in phenyl hydrogen-containing silicon oil, hydrogeneous mass percent is 0.2%, be 40% containing benzene mass percent, viscosity is 20mpas, and refractive index is 1.50) and catalyzer add in reactor, stirring is warming up to 115 DEG C, and after reacting 9h at this temperature, reduce temperature of reaction to room temperature, obtain polyether-modified phenyl hydrogen-containing silicon oil; Wherein, the mol ratio of phenyl hydrogen-containing silicon oil and polyethers is 1:1.1, and the quality of catalyzer is the ratio of phenyl hydrogen-containing silicon oil and allyl alcohol polyether total mass is 40 μ g:1g, the aqueous isopropanol of catalyzer to be mass concentration the be Platinic chloride of 2%.
Embodiment 7
A kind of preparation method of polyether-modified phenyl hydrogen-containing silicon oil, under nitrogen protection, by phenyl hydrogen-containing silicon oil, (in phenyl hydrogen-containing silicon oil, hydrogeneous mass percent is 0.3%, be 25% containing benzene mass percent, viscosity is 10mpas, and refractive index is 1.50) and catalyzer add in reactor, stirring is warming up to 120 DEG C, and after reacting 8h at this temperature, reduce temperature of reaction to room temperature, obtain polyether-modified phenyl hydrogen-containing silicon oil; Wherein, the mol ratio of phenyl hydrogen-containing silicon oil and polyethers is 1:1.2, and the quality of catalyzer is the ratio of phenyl hydrogen-containing silicon oil and allyl alcohol polyether total mass is 35 μ g:1g, the aqueous isopropanol of catalyzer to be mass concentration the be Platinic chloride of 2%.
Embodiment 8
A kind of preparation method of long chain alkyl modified phenyl hydrogen-containing silicon oil, under nitrogen protection, by phenyl hydrogen-containing silicon oil, (in phenyl hydrogen-containing silicon oil, hydrogeneous mass percent is 0.4%, be 35% containing benzene mass percent, viscosity is 30mpas, and refractive index is 1.50) and catalyzer add in reactor, stirring is warming up to 130 DEG C, and after reacting 7h at this temperature, reduce temperature of reaction to room temperature, obtain polyether-modified phenyl hydrogen-containing silicon oil; Wherein, the mol ratio of phenyl hydrogen-containing silicon oil and polyethers is 1:1.3, and the quality of catalyzer is the ratio of phenyl hydrogen-containing silicon oil and allyl alcohol polyether total mass is 32 μ g:1g, the aqueous isopropanol of catalyzer to be mass concentration the be Platinic chloride of 2%.
Represent the infrared spectrum of raw material see Fig. 2, a, b represents the infrared spectrum of product, 2156cm
-1place is the Si-H charateristic avsorption band of raw material (phenyl hydrogen-containing silicon oil), and product corresponding position absorption peak disappears, and illustrates that Si-H participates in reaction; Product is at 1642cm
-1there is faint C=C charateristic avsorption band in place, because content of polyether is more in raw material; 3513cm
-1place is-OH stretching vibration absorption peak; 2988cm
-1place is-CH
3stretching vibration absorption peak; 2950cm
-1~ 2870cm
-1the C-H stretching vibration peak at place broadens, and is to be caused by a large amount of methylene radical contained in the polyethers be introduced on containing hydrogen silicone oil chain; 1725 places be allyl alcohol polyether exist isomerization reaction produce C=O cause; 1595cm
-1, 1457cm
-1place is the skeleton peak of phenyl ring; 1373cm
-1place is C-H flexural vibration peak in-CH2-; 1260cm
-1place is Si-CH
3in-CH
3flexural vibration peak.This confirms that phenyl hydrogen-containing silicon oil and polyethers there occurs graft reaction.
Preparation method of the present invention is simple, and easy to operate, and the material prepared by the method, and owing to being that main naturally occurring emulsifying agent exists mainly with bituminous matter, colloid in crude oil, bituminous matter material is made up of the aromatic condensed ring of complexity and side chain.Colloid also has similar chemical structure.Therefore according to the similar principle mixed, in emulsion splitter molecule, the demulsification that aryl can improve emulsion splitter is introduced.Polysiloxane thermostability is relevant with several factors, easily by the restriction of condition, and on its molecular chain, introduces the object that phenyl can reach raising polysiloxane thermostability.And the introducing of polyethers can increase its wetting ability.Siloxane-Oxyalkylene Copolymers has water-soluble and oil soluble concurrently, and is easy to regulate, and this analog copolymer is all very stable in very wide pH value range, even if (reduction and bleaching) result of use is still good under high concentration basic condition.It had both had every excellent properties of traditional siloxane series products, as high-low temperature resistant, anti-aging, hydrophobic, electrical isolation, low surface tension etc., there is again the special propertys such as lubrication, soft effect, good spreadability and the emulsifying stability that polyether segment provides simultaneously, modified tensio-active agent is carried out to polyether modified siloxane again there is more excellent effect.This type of tensio-active agent has become a kind of silicone products that application quantity is maximum, kind is maximum.Therefore, the advantage both the present invention combines, utilizes polyether-modified phenyl hydrogen-containing silicon oil, obtains one and have better demulsification, and use range is wider, the tensio-active agent that condition is harsher.
Above content is in conjunction with concrete preferred implementation further description made for the present invention; can not assert that the specific embodiment of the present invention is only limitted to this; for general technical staff of the technical field of the invention; without departing from the inventive concept of the premise; some simple deduction or replace can also be made, all should be considered as belonging to the present invention by submitted to claims determination scope of patent protection.
Claims (5)
1. a polyether-modified phenyl hydrogen-containing silicon oil, is characterized in that, structural formula is as follows:
Wherein, R
1for-CH
3; R
3for-CH
2cH
2cH
2o (C
2h4O)
m(C
3h
6o)
nr
2, R
2for-H ,-CH
3,-C
2h
5or-C
3h
7; X, y, z is integer, and z is non-vanishing, and scope is 10 ~ 200; M, n are integer, and are 0 when m, n are different; M=0 ~ 40; N=0 ~ 30.
2. the preparation method of a polyether-modified phenyl hydrogen-containing silicon oil as claimed in claim 1, it is characterized in that, under nitrogen protection, the aqueous isopropanol of Platinic chloride, phenyl hydrogen-containing silicon oil and polyethers are added in reactor, at 100 ~ 130 DEG C, react 7 ~ 10h, obtain polyether-modified phenyl hydrogen-containing silicon oil; Wherein, the mol ratio of phenyl hydrogen-containing silicon oil, polyethers is 1:(1 ~ 1.3), the ratio of the quality of the aqueous isopropanol of Platinic chloride and phenyl hydrogen-containing silicon oil and polyethers total mass is (30 ~ 40) μ g:1g.
3. the preparation method of a kind of polyether-modified phenyl hydrogen-containing silicon oil according to claim 2, it is characterized in that, in described phenyl hydrogen-containing silicon oil, hydrogeneous mass percent is 0.1 ~ 0.5%, is 20 ~ 40% containing benzene mass percent, viscosity is 10 ~ 30mpas, and refractive index is 1.50.
4. the preparation method of a kind of polyether-modified phenyl hydrogen-containing silicon oil according to claim 2, is characterized in that, described polyethers is allyl alcohol polyether, and structural formula is
Wherein, R
2for-H ,-CH
3,-C
2h
5or-C
3h
7; M=0 ~ 40; N=0 ~ 30; M, n are integer, and are 0 when m, n are different.
5. the preparation method of a kind of polyether-modified phenyl hydrogen-containing silicon oil according to claim 2, is characterized in that, the mass concentration of the aqueous isopropanol of described Platinic chloride is 2%.
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| CN105778107A (en) * | 2016-03-15 | 2016-07-20 | 陕西科技大学 | Oil-soluble demulsifier and preparation method thereof |
| CN106800656A (en) * | 2016-12-06 | 2017-06-06 | 天诺光电材料股份有限公司 | A kind of giant electro-rheological liquid high temperature resistant polyether modified silicon oil and preparation method thereof |
| CN108164709A (en) * | 2017-12-25 | 2018-06-15 | 上海氟聚化学产品股份有限公司 | A kind of preparation method of polyether-modified chain alkyl phenyl silicone oil |
| CN109021243A (en) * | 2018-06-25 | 2018-12-18 | 陕西科技大学 | A kind of long chain fluorine-containing Arrcostab and polyethers are modified the preparation method of phenyl hydrogen-containing silicon oil altogether |
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