CN104231197A - Amido omodified phenolic resin and preparation method thereof - Google Patents

Amido omodified phenolic resin and preparation method thereof Download PDF

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Publication number
CN104231197A
CN104231197A CN201410454096.9A CN201410454096A CN104231197A CN 104231197 A CN104231197 A CN 104231197A CN 201410454096 A CN201410454096 A CN 201410454096A CN 104231197 A CN104231197 A CN 104231197A
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omodified
amido
phenolic resin
phenol
phenolic
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CN104231197B (en
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魏强
杜大委
李支文
郭海军
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CNOOC Energy Technology and Services Ltd
CNOOC Tianjin Oilfield Chemical Co Ltd
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China National Offshore Oil Corp CNOOC
CNOOC Energy Technology and Services Ltd
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Abstract

The invention discloses amido omodified phenolic resin and a preparation method thereof. The preparation method of the amido omodified phenolic resin comprises the following steps: firstly, enabling phenol compounds and one part of aldehyde compounds to generate phenolic aldehyde compounds under the action of an acid catalyst; then, adding sequentially vinyl amine compounds and the rest of aldehyde compounds to react, thereby finally obtaining the amido omodified phenolic resin, wherein the molar ratio of the phenol compounds to the aldehyde compounds to the vinyl amine compounds is 1.00 to (1.00-2.80) to (0.15-2.50). The preparation method has the advantage that an intramolecular mixing technology is adopted to integrate a plurality of benzene rings with a plurality of reactive hydrogen structures into an initiator molecule, namely molecules of the amido omodified phenolic resin; an aromatic structure and a plurality of reactive hydrogen atoms are provided in the molecular structure of the amido omodified phenolic resin at the same time, so that the amido omodified phenolic resin can be used as an initiator for an aromatic multi-branched emulsion breaker for oil field raw oil dehydration and refinery plant raw oil dehydration and desalination.

Description

A kind of amino modified resol and preparation method thereof
Technical field
The present invention relates to a kind of amino modified resol for the preparation of emulsion splitter initiator and preparation method thereof, belong to Petroleum Processing Technology field.
Background technology
In crude production, crude oil normally water-in-oil or O/w emulsion form exist, water and be dissolved in the process such as production, transport, refining of electrolytical existence wherein to crude oil and have extremely adverse influence, therefore must be down to former Water in oil within acceptable scope by breakdown of emulsion or dehydration.At present, breakdown of emulsion or dewatering comprise gravity (or centrifugal force) settling process, heat treating process, electric field treatment method and chemical demulsification method, and the chemical demulsification rule reaching crude oil demulsification or dehydration by adding chemical demulsifier in emulsion of crude oil is the most frequently used and most effective means.People to the research of chemical demulsification method very early, develop a large amount of emulsion splitters.Current, most widely used emulsion splitter is mainly based on the polyethers of Pluronic F-127 polycyclic oxypropylene copolymer.This type of emulsion splitter is using the compound containing reactive hydrogen as " initiator ", at effect and the segmented copolymer carrying out ring-opening polymerization with oxyethane, propylene oxide and obtain respectively of ring opening catalyst.Generally speaking, the emulsion splitter performance having different initial polyethers is different.Wherein comparatively speaking, the polyether demulsification agent taking resol as initiator is very fast to the rate of water loss of the light crude emulsion containing less pitch, and the polyether demulsification agent being initiator with amino modified phenolic compound is then very fast to the emulsion of crude oil rate of water loss containing more pitch.The application that this two classes emulsion splitter all industrially obtains.But this two classes emulsion splitter all exists the narrow shortcoming of adaptability, this brings certain restriction to applying of this two types product, particularly in the oil field that some individual well production fluids differ greatly.Take phenol-amine resin as the product advantage that the polyether type demulsifying agent of initiator has then gathered this two type, namely racemosus structure is had in their molecular structure, there is aromatic structure again, therefore such emulsion splitter not only has that rate of water loss is fast, the feature of less developer, also have the wide scope of application, crude oil production fluid that is more to bituminous and that contain paraffin more all has good treatment effect.What Chinese patent CN201310683689, CN201310347875, CN201210581160, CN201210115016, CN201110108168, CN200710010069, CN200610057168, CN200610057168, CN200310105425 and CN200310105425 reported is all this take phenol-amine resin as the polyether demulsification agent of initiator.But report in these patents with phenol-amine resin to be that the shortcoming of the polyether demulsification agent of initiator is in their molecular structure general only containing an aromatic group, that is, the aromaticity of this emulsion splitter molecule is very low.And according to modern breakdown of emulsion Theory and applications experience, when the oleophilic group of emulsion splitter and emulsifying agent have similar structure and molecular weight is close, the effect of breakdown of emulsion is often better.The emulsifying agent that in crude oil, content is at most, emulsifying capacity is the strongest is bituminous matter, and bituminous matter is a kind of polynuclear compound of aromaticity, its molecular weight about hundreds of between thousands of.Therefore with regard to similarity, conventional phenol-amine resin obviously and asphaltene molecules structurally there is notable difference, this also just limits applying more widely with the conventional phenol-amine resin polyether demulsification agent that is initiator.
Summary of the invention
In order to overcome above-mentioned the deficiencies in the prior art, the invention provides a kind of novel amino modified resol and preparation method thereof, there is in the molecular structure of this amino modified resol two or more aromatic structure and multiple reactive hydrogen atom simultaneously, structurally more similar with bituminous matter, can be used as the initiator of the hyper-branched emulsion splitter of aromaticity of crude oil dehydration and refinery's dehydrate and desalt of crude oil.
Amino modified resol provided by the present invention, has the novel amido modified phenolic resins of formula I structure.
Wherein n is the positive integer of 0 ~ 6; P, q are the positive integers of 1-5, R 1, R 2and R 3to be carbonatoms be 1 ~ 9 alkyl, also can be-CH 2nH (CH 2cH 2nH) kh, wherein k is the positive integer of 1-5, and k, p and q can be the same or different, R 1, R 2and R 3can be the same or different; R 4hydrogen atom or methyl.
Amino modified resol of the present invention first under the effect of an acidic catalyst, generates novolak products by phenolic compound and the aldehyde compound of a part, and then add vinyl-amine compounds successively and remaining aldehyde compound carries out modified-reaction; The mol ratio of phenolic compound, aldehyde compound and vinyl-amine compounds is 1.00:(1.00-2.80): (0.15-2.50).
In amino modified resol of the present invention, for the synthesis of aldehyde compound be preferably formaldehyde or acetaldehyde.
In amino modified resol of the present invention, for the synthesis of phenolic compound be preferably in phenol, p-methyl phenol, p-tert-butylphenol, paraoctyl phenol, nonylphenol one or more.
In amino modified resol of the present invention, for the synthesis of vinyl-amine compounds be preferably in quadrol, diethylenetriamine, triethylene tetramine, tetraethylene pentamine or five ethene hexamines one or more.
In amino modified resol of the present invention, for the synthesis of an acidic catalyst be preferably in sulfuric acid, oxalic acid, phosphoric acid, Phenylsulfonic acid, p-methyl benzenesulfonic acid one or more.
The preparation method of amino modified resol of the present invention, first generate novolak products by aldehyde compound back flow reaction 2h-6h under the effect of an acidic catalyst of phenolic compound and 50% ~ 80% molar weight, and then add vinyl-amine compounds and remaining aldehyde compound successively in 60 DEG C-110 DEG C reaction 2h-8h, the target product finally obtained.
The invention has the advantages that and adopt hybrid technology in molecule, multiple phenyl ring and multiple reactive hydrogen structural integrity are entered in the molecule of a starter molecules and amino modified resol, there is in the molecular structure of this amino modified resol aromatic structure and multiple reactive hydrogen atom simultaneously, can be used as the initiator of the hyper-branched emulsion splitter of aromaticity of crude oil dehydration and refinery's dehydrate and desalt of crude oil.
Embodiment
Embodiment 1
Electric stirring is being housed, in the there-necked flask of thermometer and prolong, add the phenol of 94.0g, the formaldehyde solution of the 38%-40% of 38.5g, open and stir, the catalyst sulfuric acid of 0.2g is added after phenol dissolves completely, slowly be warming up to system backflow, after reaction 2h, stop heating, the quadrol of 240.0g is added when temperature is down to below 45 DEG C, stir, then at 45 DEG C, drip the formaldehyde solution of the 38%-40% of 307.7g, 60 DEG C of reaction 8h are warmed up to after dropwising, last at 135 DEG C, reduce pressure under 202Pa the water steamed in system, obtain target quadrol modified phenolic resins, its average formula is such as formula shown in II.
Embodiment 2
Electric stirring is being housed, in the there-necked flask of thermometer and prolong, add the nonylphenol of 22.0g, the formaldehyde solution of the 38%-40% of 67.3g, open and stir, add the catalyzer tosic acid of 2.5g, slowly be warming up to system backflow, after reaction 3h, be warming up to 135 DEG C, reduce pressure the 2h that dewaters under 202Pa, stop heating and vacuumize, the diethylenetriamine of 30.0g is added when temperature is down to below 100 DEG C, stir, then at 80 DEG C, drip the formaldehyde solution of the 38%-40% of 21.0g, dropwise rear insulation 80 DEG C reaction 4h, last at 135 DEG C, reduce pressure under 202Pa the water steamed in system, obtain target diethylenetriamine modification resol in the ninth of the ten Heavenly Stems, its average formula is as shown in formula III.
Embodiment 3
Electric stirring is being housed, in the there-necked flask of thermometer and prolong, add the p-tert-butylphenol of 150.0g, the formaldehyde solution of the 38%-40% of 57.7g, open and stir, add the catalyzer oxalic acid of 5g, slowly be warming up to backflow, 2g oxalic acid is added again after reaction 3h, continue reaction 1h, stop heating, the triethylene tetramine of 73.1g is added when temperature is down to below 45 DEG C, stir, then at 45 DEG C, drip the formaldehyde solution of the 38%-40% of 38.5g, 70 DEG C of reaction 6h are warmed up to after dropwising, last at 135 DEG C, reduce pressure under 202Pa the water steamed in system, obtain target triethylene tetramine modification tert butyl phenolic resin, its average formula is such as formula shown in IV.
Embodiment 4
Electric stirring is being housed, in the there-necked flask of thermometer and prolong, add the p-tert-butylphenol of 75.0g, the nonylphenol of 110.0g, the formaldehyde solution of the 38%-40% of 38.5g, open and stir, add the catalyzer phosphoric acid of 1.0g, slowly be warming up to system backflow, the oxalic acid adding 1.0g after reaction 3h continues reaction 1h, stop heating, the tetraethylene pentamine of 189.0g is added when temperature is down to below 45 DEG C, stir, then at 45 DEG C, drip the formaldehyde solution of the 38%-40% of 76.9g, 80 DEG C of reaction 4h are warmed up to after dropwising, last at 135 DEG C, reduce pressure under 202Pa the water steamed in system, obtain target tetraethylene pentamine modification tertiary butyl nonylphenolic resin, its average structure is such as formula shown in V.
Embodiment 5
Electric stirring is being housed, in the there-necked flask of thermometer and prolong, add the paraoctyl phenol of 206.3g, the formaldehyde solution of the 38%-40% of 51.5g, open and stir, the catalyzer p-methyl benzenesulfonic acid of 2.0g is added after phenol dissolves completely, slowly be warming up to system backflow, add 1g oxalic acid after reaction 4h and continue reaction 1h, stop heating, the five ethene hexamines of 126.6g are added when temperature is down to below 45 DEG C, stir, then at 45 DEG C, drip the formaldehyde solution of the 38%-40% of 40% of 51.5g, 80 DEG C of reaction 4h are warmed up to after dropwising, last at 130 DEG C, reduce pressure under 202Pa the water steamed in system, obtain target five ethene hexamine modification octyl phenolic, its average structure is such as formula shown in VI.
Embodiment 6
In the enamel reaction still of 5 sides, by nonyl phenol: the ratio of the amount of formaldehyde=1:0.85 feeds intake, add the nonylphenol of about 2.0 tons, the formaldehyde solution of 0.59 ton of 38%-40% from raw material scale tank.Start and stir, and the phosphoric acid adjust ph adding 30% is 1.0-2.0 scope.Progressively heat, stop heating when temperature in the kettle reaches about 80 DEG C.Owing to being thermopositive reaction, material temperature can rise to boiling automatically, 1h is kept after boiling balance, cool to 75 DEG C, add phosphoric acid again, the phosphoric acid consumption that front and back add for twice is 0.08% of nonylphenol quality, slowly be warming up to boiling again, maintain about 1h, cool to 50 DEG C, add the diethylenetriamine of 0.4 ton and the tetraethylene pentamine of 0.4 ton, the formaldehyde solution of the 38%-40% of 0.14 ton is dripped after stirring, after be warmed up to 110 DEG C reaction 3h, last at 135 DEG C, reduce pressure under 387Pa the water steamed in system, obtain target diethylenetriamine and triethylene tetramine modification nonylphenolic resin, its average structure is such as formula shown in VII.
Embodiment 7
Electric stirring is being housed, in the there-necked flask of thermometer and prolong, add the phenol of 94.0g, 55.5g 40% acetaldehyde solution, open and stir, the catalyzer Phenylsulfonic acid of 2.0g is added after phenol dissolves completely, slowly be warming up to system backflow, after reaction 6h, stop heating, the diethylenetriamine of 214g is added when temperature is down to below 45 DEG C, stir, then at 45 DEG C, drip the acetaldehyde solution of 40% of 220g, 100 DEG C of reaction 2h are warmed up to after dropwising, last at 130 DEG C, reduce pressure under 202Pa the water steamed in system, obtain target diethylenetriamine modified phenol acetaldehyde resin, its average formula is such as formula shown in VIII.
Embodiment 8
Electric stirring is being housed, in the there-necked flask of thermometer and prolong, add the p-tert-butylphenol of 75.0g, 46.0g phenol, the formaldehyde solution of the 38%-40% of 38.5g, open and stir, add the catalyzer tosic acid of 2.0g, slowly be warming up to system backflow, the oxalic acid adding 1.0g after reaction 2h continues reaction 1h, stop heating, the diethylenetriamine of 161.0g is added when temperature is down to below 45 DEG C, stir, then at 45 DEG C, drip the formaldehyde solution of the 38%-40% of 115.4g, 90 DEG C of reaction 4h are warmed up to after dropwising, last at 135 DEG C, reduce pressure under 202Pa the water steamed in system, obtain target diethylenetriamine modification tert.-butylbenzene phenolic group resol, its average formula is such as formula shown in IX.
Embodiment 9
Electric stirring is being housed, in the there-necked flask of thermometer and prolong, add 206.0g to octyl phenol, 91.6g 40% acetaldehyde solution, open and stir, add the catalyzer tosic acid of 2.5g, slowly be warming up to system backflow, after reaction 3h, be warming up to 135 DEG C, reduce pressure the 2h that dewaters under 202Pa, stop heating and vacuumize, the diethylenetriamine of 36.0g is added when temperature is down to below 100 DEG C, stir, then at 80 DEG C, drip the acetaldehyde solution of 40% of 36.7g, dropwise rear insulation 80 DEG C reaction 4h, last at 135 DEG C, reduce pressure under 202Pa the water steamed in system, obtain target diethylenetriamine modification octyl phenolic, its average formula is such as formula shown in X.
Embodiment 10
Electric stirring is being housed, in the there-necked flask of thermometer and prolong, add the p-tert-butylphenol of 75.0g, 46.0g phenol, the formaldehyde solution of the 38%-40% of 38.5g, open and stir, add the catalyzer phosphoric acid of 1.0g, slowly be warming up to system backflow, the oxalic acid adding 1.0g after reaction 2h continues reaction 1h, stop heating, the tetraethylene pentamine of 283.5g is added when temperature is down to below 45 DEG C, stir, then at 45 DEG C, drip the formaldehyde solution of the 38%-40% of 115.4g, 80 DEG C of reaction 4h are warmed up to after dropwising, last at 135 DEG C, reduce pressure under 202Pa the water steamed in system, obtain target tetraethylene pentamine modification tert-butyl phenol phenol novolacs, its average formula is such as formula shown in XI.
Embodiment 11
With the amino modified resol prepared in various embodiments of the present invention for initiator, according to initiator: propylene oxide: the quality of oxyethane=1:59:12 is than synthesizing polyether type emulsion splitter, each emulsion splitter title represents with " ' embodiment number '-polyethers ", and the effect of they and conventional polyether emulsion splitter AE6051 is contrasted, the crude oil production fluid for contrast experiment takes from the different offshore oilfield of China.
Contrast 1:
Table 1: oil sample is originated: SZ36-1 oil field temperature: 68 DEG C of oil samples are moisture: about 50% hybrid mode: hand 200 times
Contrast 2:
Table 2: oil sample is originated: WZ11-4 oil field temperature: 77 DEG C of oil samples are moisture: about 35% hybrid mode: hand 200 times
Can clearly find out from contrast table: the polyether demulsification agent effect adopting amino modified resol provided by the invention to prepare is better than conventional polyether emulsion splitter.

Claims (7)

1. an amino modified resol, is characterized in that having following structure:
Wherein n is the positive integer of 0 ~ 6; P, q are the positive integers of 1 ~ 5; R 1, R 2and R 3to be carbonatoms be 1 ~ 9 alkyl, or-CH 2nH (CH 2cH 2nH) kh, wherein k is the positive integer of 1 ~ 5; K, p or q are identical or different, R 1, R 2or R 3identical or different; R 4hydrogen atom or methyl.
2. the amino modified preparation method of phenolic resin of claim 1, it is characterized in that it is generated under catalyst action by phenolic compound, aldehyde compound and vinyl-amine compounds, the mol ratio of described phenolic compound, aldehyde compound and vinyl-amine compounds is 1.00:(1.00 ~ 2.80): (0.15 ~ 2.50), the quality of an acidic catalyst accounts for 0.02% ~ 5% of phenolic compound quality.
3. method according to claim 2, is characterized in that described aldehyde compound is formaldehyde or acetaldehyde.
4. method according to claim 2, is characterized in that described phenolic compound is one or more in phenol, p-methyl phenol, p-tert-butylphenol, paraoctyl phenol or nonylphenol.
5. method according to claim 2, is characterized in that described vinyl-amine compounds is one or more in quadrol, diethylenetriamine, triethylene tetramine, tetraethylene pentamine or five ethene hexamines.
6. method according to claim 2, is characterized in that described an acidic catalyst is one or more in sulfuric acid, oxalic acid, phosphoric acid, Phenylsulfonic acid or p-methyl benzenesulfonic acid.
7. method according to claim 2, it is characterized in that: first generate novolak products by aldehyde compound back flow reaction 2h ~ 6h under the effect of an acidic catalyst of phenolic compound and 50% ~ 80% molar weight, and then add vinyl-amine compounds and remaining aldehyde compound successively in 60 DEG C ~ 110 DEG C reaction 2h ~ 8h, the target product finally obtained.
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Cited By (11)

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CN105316028A (en) * 2014-12-28 2016-02-10 新疆科力新技术发展有限公司 Organic acid-polyether type dirty oil demulsifying agent and preparation method thereof
CN105885029A (en) * 2016-05-07 2016-08-24 中国海洋石油总公司 Polyether demulsifying agent based on hydramine-modified phenolic resin and synthesizing method thereof
CN107603403A (en) * 2017-10-10 2018-01-19 徐州赛欧电子科技有限公司 A kind of preparation method of novel antirust coating
CN107778474A (en) * 2016-08-31 2018-03-09 克拉玛依市天明化工有限责任公司 A kind of preparation method of high-efficient demulsifier
CN108641697A (en) * 2018-04-20 2018-10-12 黄智慧 A kind of preparation method of demulsifier
CN110387256A (en) * 2018-04-23 2019-10-29 盘锦富隆化工有限公司 A kind of poly- repelling crude oil low temperature rapid demulsifier and preparation method thereof
JP2021004270A (en) * 2019-06-25 2021-01-14 住友ベークライト株式会社 Phenol resin
CN112898205A (en) * 2021-01-12 2021-06-04 华东师范大学 Method for synthesizing benzimidazole by using carbon dioxide and o-phenylenediamine compound
CN113322095A (en) * 2021-07-01 2021-08-31 中海油天津化工研究设计院有限公司 Ultra-high temperature oil slurry settling agent and method for removing oil slurry ash content at ultra-high temperature
CN114316244A (en) * 2021-12-29 2022-04-12 滨化集团股份有限公司 Polymer flooding produced liquid demulsifier and preparation method thereof
CN114621105A (en) * 2020-12-10 2022-06-14 中国石油化工股份有限公司 Polymer-containing crude oil demulsifier and preparation method thereof

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CN105316028A (en) * 2014-12-28 2016-02-10 新疆科力新技术发展有限公司 Organic acid-polyether type dirty oil demulsifying agent and preparation method thereof
CN105885029A (en) * 2016-05-07 2016-08-24 中国海洋石油总公司 Polyether demulsifying agent based on hydramine-modified phenolic resin and synthesizing method thereof
CN107778474A (en) * 2016-08-31 2018-03-09 克拉玛依市天明化工有限责任公司 A kind of preparation method of high-efficient demulsifier
CN107778474B (en) * 2016-08-31 2020-07-07 克拉玛依市天明化工有限责任公司 Preparation method of efficient demulsifier
CN107603403A (en) * 2017-10-10 2018-01-19 徐州赛欧电子科技有限公司 A kind of preparation method of novel antirust coating
CN108641697A (en) * 2018-04-20 2018-10-12 黄智慧 A kind of preparation method of demulsifier
CN110387256B (en) * 2018-04-23 2021-11-19 盘锦富隆化工有限公司 Low-temperature rapid demulsifier for polymer flooding crude oil and preparation method thereof
CN110387256A (en) * 2018-04-23 2019-10-29 盘锦富隆化工有限公司 A kind of poly- repelling crude oil low temperature rapid demulsifier and preparation method thereof
JP2021004270A (en) * 2019-06-25 2021-01-14 住友ベークライト株式会社 Phenol resin
CN114621105A (en) * 2020-12-10 2022-06-14 中国石油化工股份有限公司 Polymer-containing crude oil demulsifier and preparation method thereof
CN112898205A (en) * 2021-01-12 2021-06-04 华东师范大学 Method for synthesizing benzimidazole by using carbon dioxide and o-phenylenediamine compound
CN112898205B (en) * 2021-01-12 2022-10-04 华东师范大学 Method for synthesizing benzimidazole by using carbon dioxide and o-phenylenediamine compound
CN113322095A (en) * 2021-07-01 2021-08-31 中海油天津化工研究设计院有限公司 Ultra-high temperature oil slurry settling agent and method for removing oil slurry ash content at ultra-high temperature
CN113322095B (en) * 2021-07-01 2023-08-04 中海油天津化工研究设计院有限公司 Ultrahigh-temperature slurry oil sedimentation agent and ultrahigh-temperature slurry oil ash removal method thereof
CN114316244A (en) * 2021-12-29 2022-04-12 滨化集团股份有限公司 Polymer flooding produced liquid demulsifier and preparation method thereof

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