CN100369946C - Chain extender, its preparation method and application - Google Patents
Chain extender, its preparation method and application Download PDFInfo
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- CN100369946C CN100369946C CNB2005101303445A CN200510130344A CN100369946C CN 100369946 C CN100369946 C CN 100369946C CN B2005101303445 A CNB2005101303445 A CN B2005101303445A CN 200510130344 A CN200510130344 A CN 200510130344A CN 100369946 C CN100369946 C CN 100369946C
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Abstract
The present invention discloses a chain extender, a preparation method and the application thereof. The chain extender is a random copolymer which is composed of structural units represented by formulae I, II and III and with the molar ratio of 1: (0.01 to 0.04): (0.01 to 0.09) and has the weight average molecular weight of 600 to 2800. The structural formula structural formulae of I, II and III are disclosed in the specification. The chain extender of the present invention can be widely used for preparing various demulsifier substances.
Description
Technical field
The present invention relates to a kind of chainextender and preparation method thereof and application.
Background technology
Crude oil at first makes its water ratio up to standard through joint station or treatment plant's dehydration after oil well produced, could outer be passed to refinery refining processing.At present, for oil increasing precipitation, realize the stable yields volume increase of crude oil high moisture period during domestic most of oil field has entered, polymer displacement of reservoir oil tech has become chemical flooding and has improved one of dominant technology of recovery ratio, and has obtained huge technology, economic and social benefit.Meanwhile, the existence of polymkeric substance has increased the difficulty of crude oil demulsification dehydration, particularly to the viscous crude of high gum asphaltic content, adopts hydrophobic associated polymer as oil-displacing agent, and the breaking emulsion and dewatering difficulty of its extraction crude oil is just bigger.
The crude oil demulsifier of present commercial applications, polyethers has occupied the share of absolute majority, and in the polyethers emulsion splitter, major part is after utilizing initiator and oxyethane and propylene oxide reaction, improve the molecular weight of emulsion splitter again by chainextender, realize the performance synergy of emulsion splitter.In development, production and the application of crude oil demulsifier, about the existing great mass of data report in aspects such as initiator, raw material type, polymerization methods and synthetic method.It is less that yet the research work of the chainextender aspect of one of important source material is paid close attention to, in emulsion splitter is synthetic, the chemical reagent of chainextender many commodities in useization, as: CN1544117A uses linking agents (chainextender) such as tolylene diisocyanate and Vanadium Pentoxide in FLAKES, EP0141585 and DE3319788 use chainextenders such as tolylene diisocyanate and organosilicon, CN1101238C uses tolylene diisocyanate and multi-aryl polyisocyanate chainextender, (Speciality Petrochemicals such as Gong Huijuan, 2000,4:1-4) use tolylene diisocyanate and many alkylenes polyisocyanates chainextender, (petroleum journal (refining of petroleum) such as Xu Jiaye, 2002,18 (2): 48-52) use the hexanodioic acid chainextender, WOP9213933A1 uses tetrapropylene succinyl oxide chainextender, in addition, also has diprotic acid, dimer (fatty acid) yl, dibasic acid anhydride etc.This shows that the polyfunctional group class chainextender of specialized designs synthetic macromolecule amount is rare report still, corresponding crude oil demulsifier research is not seen and is delivered.
Summary of the invention
The purpose of this invention is to provide a kind of new chainextender.
Chainextender provided by the present invention is the structural unit of being represented by following formula I, formula II and formula III, and with 1: 0.01-0.04: the weight-average molecular weight that the mol ratio of 0.01-0.09 is formed is the random copolymers of 600-2800; The structural formula of formula I, formula II and formula III is as follows:
Formula I formula II formula III
R among the formula I
1Expression H or CH
3, R
2Expression CH
3Or C
4H
9
Another object of the present invention provides the preparation method of above-mentioned chainextender.
The method of the above-mentioned chainextender of preparation provided by the present invention, form by following step:
1) be 1 with mol ratio: the acrylate of 0.01-0.12 and hydroxyethyl methylacrylate are dissolved in toluene or dimethylbenzene, add the dibenzoyl peroxide of 0.02-0.6% of described acrylate and hydroxyethyl methylacrylate total mass or following any chain-transfer agent of 1-9% of azo-bis-isobutyl cyanide and described acrylate and hydroxyethyl methylacrylate total mass: Resorcinol, phenol, antioxidant 1010, Virahol or mercaptoethanol, at 70-100 ℃ of copolyreaction 2-6 hour, obtain the multipolymer of acrylate and hydroxyethyl methylacrylate;
2) adding in the acrylate that obtains in step 1) and the multipolymer of hydroxyethyl methylacrylate is the phosphorus tribromide of described hydroxyethyl methylacrylate mole number 1/3rd, 90-110 ℃ following bromine substitution reaction 4-8 hour, 90 ℃ of underpressure distillation promptly get chainextender.
The present invention specifically provides following five kinds of preferred preparation chainextender methods:
First method is: in the described method, described acrylate is a methyl acrylate, and the mol ratio of described methyl acrylate and hydroxyethyl methylacrylate can be 1: 0.03; Described dibenzoyl peroxide can be 0.12% of described methyl acrylate and hydroxyethyl methylacrylate total mass; Described chain-transfer agent is a Resorcinol, and described Resorcinol is 2% of described methyl acrylate and a hydroxyethyl methylacrylate total mass; Described copolyreaction temperature can be 90 ℃, and the copolyreaction time can be 4 hours, and 100 ℃ of bromine substitution reaction times can be 4 hours.
Second method is: in the described method, described acrylate is a butyl acrylate, and the mol ratio of described butyl acrylate and hydroxyethyl methylacrylate can be 1: 0.04; Described dibenzoyl peroxide can be 0.07% of described butyl acrylate and hydroxyethyl methylacrylate total mass; Described chain-transfer agent is a Virahol, and described Virahol is 9% of described butyl acrylate and a hydroxyethyl methylacrylate total mass; Described copolyreaction temperature can be 80 ℃, and the copolyreaction time can be 6 hours, and 95 ℃ of bromine substitution reaction times can be 5 hours.
The third method is: in the described method, described acrylate is a butyl methacrylate, and the mol ratio of described butyl methacrylate and hydroxyethyl methylacrylate can be 1: 0.10; Described dibenzoyl peroxide can be 0.2% of described butyl methacrylate and hydroxyethyl methylacrylate total mass; Described chain-transfer agent is a phenol, and described phenol is 3% of described butyl methacrylate and hydroxyethyl methylacrylate total mass; Described copolyreaction temperature can be 75 ℃, and the copolyreaction time can be 5 hours, and 90 ℃ of bromine substitution reaction times can be 7 hours.
The 4th kind of method is: in the described method, described acrylate is a methyl methacrylate, and the mol ratio of described methyl methacrylate and hydroxyethyl methylacrylate can be 1: 0.08; Described dibenzoyl peroxide can be 0.5% of described methyl methacrylate and hydroxyethyl methylacrylate total mass; Described chain-transfer agent is a mercaptoethanol, and described mercaptoethanol is 2% of described methyl methacrylate and a hydroxyethyl methylacrylate total mass; Described copolyreaction temperature can be 100 ℃, and the copolyreaction time can be 2 hours, and 105 ℃ of bromine substitution reaction times can be 4 hours.
The 5th kind of method is: in the described method, described acrylate is a methyl methacrylate, and the mol ratio of described methyl methacrylate and hydroxyethyl methylacrylate can be 1: 0.12; Described dibenzoyl peroxide can be 0.42% of described methyl methacrylate and hydroxyethyl methylacrylate total mass; Described chain-transfer agent is a mercaptoethanol, and described mercaptoethanol is 4% of described methyl methacrylate and a hydroxyethyl methylacrylate total mass; Described copolyreaction temperature can be 95 ℃, and the copolyreaction time can be 3 hours, and 90 ℃ of bromine substitution reaction times can be 8 hours.
The synthetic required raw material of chainextender of the present invention conveniently is easy to get, and preparation technology is simple; But the requirement of the molecular weight of chainextender, reactive behavior side group amount and structure based on crude emulsion splitter and adjusting arbitrarily, and its dosage is few, polyethers emulsion splitter with its preparation has the advantages that molecular weight is high and the degree of branching is reasonable, preparation technology is simple, consumption is few, cost is low, be specially adapted to the efficient breaking emulsion and dewatering of viscous crude association polymer repelling crude oil, can effectively solve the problem that the viscous crude association polymer drives extraction dehydrating of crude oil difficulty.In addition, this chainextender also can be used for the preparation of other polymer flooding crude oil demulsifier and non-polymer repelling crude oil emulsion splitter.
Embodiment
Experimental technique among the following embodiment if no special instructions, is ordinary method.
Embodiment 1, weight-average molecular weight are the preparation of 1160 chainextender.
With toluene is solvent, methyl acrylate and hydroxyethyl methylacrylate are rendered in the there-necked flask by 1: 0.03 mol ratio, mechanical stirring, 2% the chain-transfer agent Resorcinol that adds 0.12% initiator dibenzoyl peroxide of methyl acrylate and hydroxyethyl methylacrylate total mass and methyl acrylate and hydroxyethyl methylacrylate total mass, 90 ℃ were reacted 4 hours, can obtain the multipolymer of methyl acrylate and hydroxyethyl methylacrylate; Adding in multipolymer is the phosphorus tribromide of hydroxyethyl methylacrylate mole number 1/3rd, mechanical stirring, and 100 ℃ of reactions 4 hours, 90 ℃ of underpressure distillation 2 hours promptly get the random copolymers chainextender.Wherein: the mol ratio of methyl acrylate, hydroxyethyl methylacrylate and methacrylic acid bromine ethyl ester structural unit is 0.9: 0.015: 0.01, and the weight-average molecular weight of this chainextender is 1160.
Embodiment 2, weight-average molecular weight are the preparation of 2580 chainextender.
With dimethylbenzene is solvent, butyl acrylate and hydroxyethyl methylacrylate are rendered in the there-necked flask by 1: 0.04 mol ratio, mechanical stirring, 9% the chain-transfer agent Virahol that adds 0.07% initiator dibenzoyl peroxide of butyl acrylate and hydroxyethyl methylacrylate total mass and butyl acrylate and hydroxyethyl methylacrylate total mass, 80 ℃ were reacted 6 hours, can obtain the multipolymer of butyl acrylate and hydroxyethyl methylacrylate; Adding in this multipolymer is the phosphorus tribromide of hydroxyethyl methylacrylate mole number 1/3rd, mechanical stirring, and 95 ℃ of reactions 5 hours, 90 ℃ of underpressure distillation 2 hours promptly get the random copolymers chainextender.Wherein: the mol ratio of butyl acrylate, hydroxyethyl methylacrylate and methacrylic acid bromine ethyl ester is 0.82: 0.014: 0.02, and the weight-average molecular weight of this chainextender is 2580.
Embodiment 3, weight-average molecular weight are the preparation of 1430 chainextender.
With toluene is solvent, butyl methacrylate and hydroxyethyl methylacrylate are rendered in the there-necked flask by 1: 0.10 mol ratio, mechanical stirring, 3% the chain-transfer agent phenol that adds 0.2% initiator dibenzoyl peroxide of butyl methacrylate and hydroxyethyl methylacrylate total mass and butyl methacrylate and hydroxyethyl methylacrylate total mass, 75 ℃ were reacted 5 hours, can obtain the multipolymer of butyl methacrylate and hydroxyethyl methylacrylate; Adding in multipolymer is the phosphorus tribromide of hydroxyethyl methylacrylate mole number 1/3rd, mechanical stirring, and 90 ℃ of reactions 7 hours, 90 ℃ of underpressure distillation 3 hours promptly get the random copolymers chainextender.Wherein: the mol ratio of butyl methacrylate, hydroxyethyl methylacrylate and methacrylic acid bromine ethyl ester structural unit is 0.93: 0.024: 0.056, and the weight-average molecular weight of this chainextender is 1430.
Embodiment 4, weight-average molecular weight are the preparation of 710 chainextender.
With dimethylbenzene is solvent, methyl methacrylate and hydroxyethyl methylacrylate are rendered in the there-necked flask by 1: 0.08 mol ratio, mechanical stirring, 2% the chain-transfer agent mercaptoethanol that adds 0.5% initiator dibenzoyl peroxide of methyl methacrylate and hydroxyethyl methylacrylate total mass and methyl methacrylate and hydroxyethyl methylacrylate total mass, 100 ℃ were reacted 2 hours, can obtain the multipolymer of methyl methacrylate and hydroxyethyl methylacrylate; Adding in this multipolymer is the phosphorus tribromide of hydroxyethyl methylacrylate mole number 1/3rd, mechanical stirring, and 105 ℃ of reactions 4 hours, 90 ℃ of underpressure distillation 2 hours promptly get the random copolymers chainextender.Wherein: the mol ratio of methyl methacrylate, hydroxyethyl methylacrylate and methacrylic acid bromine ethyl ester structural unit is 0.78:0.022: 0.036, and the weight-average molecular weight of this chainextender is 710.
Embodiment 5, weight-average molecular weight are the preparation of 1090 chainextender.
With toluene is solvent, methyl methacrylate and hydroxyethyl methylacrylate are rendered in the there-necked flask by 1: 0.12 mol ratio, mechanical stirring, 4% the chain-transfer agent mercaptoethanol that adds 0.42% initiator dibenzoyl peroxide of methyl methacrylate and hydroxyethyl methylacrylate total mass and methyl methacrylate and hydroxyethyl methylacrylate total mass, 95 ℃ were reacted 3 hours, can obtain the multipolymer of methyl methacrylate and hydroxyethyl methylacrylate; Adding in this multipolymer is the phosphorus tribromide of hydroxyethyl methylacrylate mole number 1/3rd, mechanical stirring, and 90 ℃ of reactions 8 hours, 90 ℃ of underpressure distillation 2 hours promptly get the random copolymers chainextender.Wherein: the mol ratio of methyl methacrylate, hydroxyethyl methylacrylate and methacrylic acid bromine ethyl ester structural unit is 0.94: 0.016: 0.087, and the weight-average molecular weight of this chainextender is 1090.
Embodiment 6, prepare emulsion splitter with the chainextender of embodiment 4
With dimethylbenzene is solvent, add the initiator tetraethylene pentamine, the mean polymerisation degree that adds total mass then and be 100 times of quality of initiator is that 30 polyethylene oxide and mean polymerisation degree are that 19 poly(propylene oxide)s mix, wherein, mean polymerisation degree is that 30 polyethylene oxide and mean polymerisation degree are that the mass ratio of 19 poly(propylene oxide) is 1: 3; Add is that described mean polymerisation degree is that 6% sodium hydroxide of 30 polyethylene oxide quality is as catalyzer again, 130 ℃, pressure is 0.5MPa, react and obtained polyethers in 2.5 hours, the chainextender of preparation among polyethers and the embodiment 4 is even by 1: 0.10 mixed in molar ratio, and adding and the equimolar pyridine of chainextender, 90 ℃ were reacted 3 hours, vacuumize the back release, obtain crude oil demulsifier.
With above-mentioned emulsion splitter Bohai SZ 36-1 oil field association polymer repelling crude oil is dewatered, concrete grammar is as follows: add the above-mentioned emulsion splitter of 9mg in 100ml crude oil, mixing, left standstill 2 hours by 70 ℃; Other gets the heating crude oil to 70 ℃ that 100ml does not contain polymkeric substance, leaves standstill 2 hours as blank, and the result shows that neater through the crude oil water-oil interface that emulsion splitter was handled, water colour is more clear, and the dehydration rate of emulsion splitter is 88%; And blank does not have water-oil interface, and water colour muddiness, dehydration rate are 10%.
Embodiment 7, prepare emulsion splitter with the chainextender of embodiment 2
With toluene is solvent, add initiator nonyl phenol urea formaldehyde, the mean polymerisation degree that adds total mass then and be 200 times of quality of initiator is that 23 polyethylene oxide and mean polymerisation degree are 15 poly(propylene oxide), mix, wherein, mean polymerisation degree is that 23 polyethylene oxide and mean polymerisation degree are that the mass ratio of 15 poly(propylene oxide) is 1: 2; Add is that described mean polymerisation degree is that 11% potassium hydroxide of 23 polyethylene oxide quality is as catalyzer again, 123 ℃, pressure is 0.4MPa, react after 3.5 hours, obtain polyethers, the chainextender of preparation among polyethers and the embodiment 2 is even by 1: 0.07 mixed in molar ratio, and the pyridine of mole numbers such as adding and chainextender, 100 ℃ were reacted 1 hour, vacuumized the back release, obtained crude oil demulsifier.
With above-mentioned emulsion splitter Bohai SZ 36-1 oil field association polymer repelling crude oil is dewatered, concrete grammar is as follows: add the above-mentioned emulsion splitter of 9mg in 100ml crude oil, 70 ℃, mixing left standstill 2 hours, other gets the heating crude oil to 70 ℃ that 100ml does not contain polymkeric substance, leave standstill 2 hours as blank, the result shows, and is neater through the crude oil water-oil interface that emulsion splitter was handled, water colour is clear, and the dehydration rate of emulsion splitter is 80%; And blank does not have water-oil interface, and the muddy dehydration rate of water colour is 10%.
Embodiment 8, prepare emulsion splitter with the chainextender of embodiment 5
With toluene is solvent, add initiator five ethene hexamines, the mean polymerisation degree that adds total mass then and be 260 times of quality of initiator is that 23 polyethylene oxide and mean polymerisation degree are 38 poly(propylene oxide), mix, wherein, mean polymerisation degree is that 23 polyethylene oxide and mean polymerisation degree are that the mass ratio of 38 poly(propylene oxide) is 1: 1.5; Add is that described mean polymerisation degree is that 4% potassium hydroxide of 23 polyethylene oxide quality is as catalyzer again, 115 ℃, pressure is 0.3MPa, react after 4 hours, obtain polyethers, the chainextender of preparation among polyethers and the embodiment 5 is even by 1: 0.12 mixed in molar ratio, and the pyridine of mole numbers such as adding and chainextender, 100 ℃ were reacted 1.5 hours, vacuumized the back release, obtained crude oil demulsifier.
With above-mentioned emulsion splitter Bohai SZ 36-1 oil field association polymer repelling crude oil is dewatered, concrete grammar is as follows: add the above-mentioned emulsion splitter of 8mg in 100ml crude oil, 70 ℃, mixing left standstill 2 hours, other gets 100ml heating crude oil to 70 ℃, leave standstill 2 hours as blank, the result shows, and is neat through the crude oil water-oil interface that emulsion splitter was handled, water colour is more clear, and the dehydration rate of emulsion splitter is 78%; And blank does not have water-oil interface, and water colour muddiness, dehydration rate are 10%.
Claims (8)
1. a chainextender is the structural unit of being represented by following formula I, formula II and formula III, and with 1: 0.01-0.04: the weight-average molecular weight that the mol ratio of 0.01-0.09 is formed is the random copolymers of 600-2800; The structural formula of formula I, formula II and formula III is as follows:
Formula I formula II formula III;
R among the formula I
1Expression H or CH
3, R
2Expression CH
3Or C
4H
9
2. the preparation method of a chainextender, be made up of following steps:
1) be 1 with mol ratio: the acrylate of 0.01-0.12 and hydroxyethyl methylacrylate are dissolved in toluene or the dimethylbenzene, add the dibenzoyl peroxide of 0.02-0.6% of described acrylate and hydroxyethyl methylacrylate total mass or following any chain-transfer agent of 1-9% of azo-bis-isobutyl cyanide and described acrylate and hydroxyethyl methylacrylate total mass: Resorcinol, phenol, antioxidant 1010, Virahol or mercaptoethanol, at 70-100 ℃ of copolyreaction 2-6 hour, obtain the multipolymer of acrylate and hydroxyethyl methylacrylate;
2) adding in the acrylate that obtains in step 1) and the multipolymer of hydroxyethyl methylacrylate is the phosphorus tribromide of described hydroxyethyl methylacrylate mole number 1/3rd, 90-110 ℃ following bromine substitution reaction 4-8 hour, 90 ℃ of underpressure distillation promptly get chainextender.
3. method according to claim 2 is characterized in that: described acrylate is a methyl acrylate, and the mol ratio of described methyl acrylate and hydroxyethyl methylacrylate is 1: 0.03; Described dibenzoyl peroxide is 0.12% of described methyl acrylate and a hydroxyethyl methylacrylate total mass; Described chain-transfer agent is a Resorcinol, and described Resorcinol is 2% of described methyl acrylate and a hydroxyethyl methylacrylate total mass; Described copolyreaction temperature is 90 ℃, and the copolyreaction time is 4 hours; Described bromine substitution reaction temperature is 100 ℃, and the bromine substitution reaction time is 4 hours.
4. method according to claim 2 is characterized in that: described acrylate is a butyl acrylate, and the mol ratio of described butyl acrylate and hydroxyethyl methylacrylate is 1: 0.04; Described dibenzoyl peroxide is 0.07% of described butyl acrylate and a hydroxyethyl methylacrylate total mass; Described chain-transfer agent is a Virahol, and described Virahol is 9% of described butyl acrylate and a hydroxyethyl methylacrylate total mass; Described copolyreaction temperature is 80 ℃, and the copolyreaction time is 6 hours; Described bromine substitution reaction temperature is 95 ℃, and the bromine substitution reaction time is 5 hours.
5. method according to claim 2 is characterized in that: described acrylate is a butyl methacrylate, and the mol ratio of described butyl methacrylate and hydroxyethyl methylacrylate is 1: 0.10; Described dibenzoyl peroxide is 0.2% of described butyl methacrylate and a hydroxyethyl methylacrylate total mass; Described chain-transfer agent is a phenol, and described phenol is 3% of described butyl methacrylate and hydroxyethyl methylacrylate total mass; Described copolyreaction temperature is 75 ℃, and the copolyreaction time is 5 hours; Described bromine substitution reaction temperature is 90 ℃, and the bromine substitution reaction time is 7 hours.
6. method according to claim 2 is characterized in that: described acrylate is a methyl methacrylate, and the mol ratio of described methyl methacrylate and hydroxyethyl methylacrylate is 1: 0.08; Described dibenzoyl peroxide is 0.5% of described methyl methacrylate and a hydroxyethyl methylacrylate total mass; Described chain-transfer agent is a mercaptoethanol, and described mercaptoethanol is 2% of described methyl methacrylate and a hydroxyethyl methylacrylate total mass; Described copolyreaction temperature is 100 ℃, and the copolyreaction time is 2 hours; Described bromine substitution reaction temperature is 105 ℃, and the bromine substitution reaction time is 4 hours.
7. method according to claim 2 is characterized in that: described acrylate is a methyl methacrylate, and the mol ratio of described methyl methacrylate and hydroxyethyl methylacrylate is 1: 0.12; Described dibenzoyl peroxide is 0.42% of described methyl methacrylate and a hydroxyethyl methylacrylate total mass; Described chain-transfer agent is a mercaptoethanol, and described mercaptoethanol is 4% of described methyl methacrylate and a hydroxyethyl methylacrylate total mass; Described copolyreaction temperature is 95 ℃, and the copolyreaction time is 3 hours; Described bromine substitution reaction temperature is 90 ℃, and the bromine substitution reaction time is 8 hours.
8. the application of the described chainextender of claim 1 in the preparation emulsion splitter.
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| DE102009019179A1 (en) * | 2009-04-28 | 2010-11-11 | Clariant International Ltd. | Alkoxylated (meth) acrylate polymers and their use as crude oil emulsion breakers |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989001507A1 (en) * | 1987-08-19 | 1989-02-23 | Pennzoil Products Company | Methacrylate pour point depressants and compositions |
| EP0635561A2 (en) * | 1993-07-23 | 1995-01-25 | Rohm And Haas Company | Copolymer useful as viscosity index improving additive for hydraulic fluid |
| EP0979834A2 (en) * | 1998-08-10 | 2000-02-16 | Ethyl Corporation | (Meth) acrylate copolymers having excellent low temperature properties |
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2005
- 2005-12-12 CN CNB2005101303445A patent/CN100369946C/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989001507A1 (en) * | 1987-08-19 | 1989-02-23 | Pennzoil Products Company | Methacrylate pour point depressants and compositions |
| EP0635561A2 (en) * | 1993-07-23 | 1995-01-25 | Rohm And Haas Company | Copolymer useful as viscosity index improving additive for hydraulic fluid |
| EP0979834A2 (en) * | 1998-08-10 | 2000-02-16 | Ethyl Corporation | (Meth) acrylate copolymers having excellent low temperature properties |
Non-Patent Citations (1)
| Title |
|---|
| 乳化原油破乳剂. 赵福麟.石油大学学报（自然科学版），第18卷第增刊期. 1994 * |
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