Demulsification additive composition, method of use thereof, and method of demulsification

Abstract

To provide a demulsification additive composition for demulsification of water-in-oil emulsion caused by wash water in the crude oil.SOLUTION: A demulsification additive composition comprises: at least one demulsifier including an oxyalkylated alkyl phenol formaldehyde resin or an oxyalkylated condensation product of at least one alkyl phenol and formaldehyde; a compound selected from the group consisting of glyoxal, neutralized glyoxal, an ethylene glycol derivative of glyoxal, and a mixture thereof; and phosphoric acid.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a demulsifying additive composition for the demulsification of water-in-oil emulsions.

[0002] In particular, the present invention relates to a demulsifier additive composition for the demulsification of water-in-oil emulsions resulting from the mixing of wash water with crude oil, more particularly in the desalter unit of a refinery.

[0003] Even more particularly, the present invention relates to a demulsifier additive composition for breaking down water-in-oil emulsions resulting from the mixing of wash water with crude oil in a desalter unit of a refinery, wherein said demulsifier additive composition comprises: (a) one or more demulsifiers; (b) a compound selected from the group consisting of glyoxal, neutralized glyoxal, and mixtures thereof; and (c) further contains phosphoric acid.

[0004] In one embodiment, the present invention relates to a method for demulsifying water-in-oil emulsions, particularly water-in-oil emulsions resulting from the mixing of wash water with crude oil, more particularly water-in-oil emulsions resulting from the mixing of wash water with crude oil, in a desalter unit of a refinery, using the demulsifier additive composition according to the present invention.

[0005] In another embodiment, the present invention relates to a method of using the demulsifier additive composition according to the present invention for demulsifying water-in-oil emulsions, particularly water-in-oil emulsions resulting from the mixing of wash water with crude oil, more particularly water-in-oil emulsions resulting from the mixing of wash water with crude oil, in a desalter unit of a refinery. [Background technology]

[0006] Water-in-oil emulsions are formed in various industrial activities, which causes substantial losses of various industrial components, such as making it difficult to separate oil. Particularly in the crude oil refining industry, wash water is mixed with crude oil in the desalting unit of the refinery, forming water-in-oil emulsions, so there is a need to break the water-in-oil emulsions.

[0007] Currently, water-in-oil emulsions resulting from mixing of the wash water with crude oil are broken by adding demulsifiers to the wash water. Summary of the Invention [Problem to be solved by the invention]

[0008] Since a large amount of demulsifier is used and it is used continuously in the processing of crude oil, there is a problem that the cost of processing crude oil increases significantly.

[0009] Another problem is that demulsifiers are expensive and therefore substantially increase the cost of processing crude oil.

[0010] More importantly, the demulsifiers currently used are condensation products of nonylphenol, and there is currently a demand to reduce consumption of nonylphenol in view of its cost and adverse environmental impact.

[0011] Therefore, there is a need to reduce, if not completely eliminate, the amount of demulsifier required so that the above-mentioned problems with the use of demulsifiers can be minimized without compromising or sacrificing the industrial output of the crude oil processing unit. [Means for solving the problem]

[0012] Thus, the present invention provides the following: i) an improved and effective demulsifying additive composition for the demulsification of water-in-oil emulsions; and ii) a method of using the demulsifying additive composition of the present invention for demulsifying a water-in-oil emulsion, and iii) A method for demulsification of water-in-oil emulsions by using the demulsifying additive composition of the present invention, thereby providing a solution to the above existing industrial problems.

[0013] Therefore, the main object of the present invention is to i) an emulsion-breaking additive composition for breaking down water-in-oil emulsions, in particular water-in-oil emulsions resulting from the mixing of wash water with crude oil, more particularly water-in-oil emulsions resulting from the mixing of wash water with crude oil, in a desalter unit of a refinery; The purpose of this project is to provide

[0014] Therefore, another object of the present invention is to ii) A method for demulsifying water-in-oil emulsions, particularly water-in-oil emulsions resulting from the mixing of wash water with crude oil, more particularly water-in-oil emulsions resulting from the mixing of wash water with crude oil, in a desalter unit of a refinery using the demulsifier additive composition of the present invention; The purpose of this project is to provide

[0015] Therefore, another object of the present invention is to iii) use of the demulsifier additive composition of the present invention for demulsifying water-in-oil emulsions, particularly water-in-oil emulsions resulting from the mixing of wash water with crude oil, more particularly water-in-oil emulsions resulting from the mixing of wash water with crude oil, in a desalter unit of a refinery; The purpose of this project is to provide

[0016] It is therefore an object of the present invention to provide a demulsifier additive composition, preferably for demulsifying water-in-oil emulsions resulting from the mixing of wash water with crude oil in the desalter unit of a refinery, more preferably for demulsifying water-in-oil emulsions resulting from the mixing of wash water with crude oil, in order to reduce the amount of demulsifiers currently used, more preferably for reducing the amount of nonylphenols or condensation products of nonylphenols, which are demulsifiers currently used in the desalter unit of a refinery, thereby reducing processing costs and the associated adverse environmental impacts.

[0017] Other objects and advantages of the present invention will become more apparent from the following description, taken in conjunction with the examples which are not intended to limit the scope of the invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0018] With the objective of overcoming the above industrial problems of the prior art and achieving the above objects of the present invention, the present inventors have: (a) one or more demulsifiers (which may be referred to as component (a)); (b) a compound (which may be referred to as component (b)) selected from the group consisting of glyoxal, neutralized glyoxal, glyoxal derivatives, and mixtures thereof; (c) further comprising phosphoric acid (which may be referred to as component (c)); It has been surprisingly and unexpectedly found that a composition further comprising:

[0019] The present inventors also discovered a combination of component (a), component (b) and component (c), A composition consisting of a combination of component (a) and component (b), and A composition comprising a combination of component (a) and component (c); It has also been surprisingly and unexpectedly found that the composition of the present invention comprising substantially improves demulsification efficiency.

[0020] Furthermore, glyoxal and neutralized glyoxal are cheaper than demulsifiers, thereby further substantially reducing the cost of processing crude oil.

[0021] Accordingly, the present invention relates to a demulsifier additive composition for the demulsification of water-in-oil emulsions resulting from wash water in crude oil, said composition comprising: (a) one or more demulsifiers (component (a)); (b) a compound (component (b)) selected from the group consisting of glyoxal, neutralized glyoxal, glyoxal derivatives and mixtures thereof; (c) Further, it contains phosphoric acid (component (c)).

[0022] The present inventors further discovered that, in the composition comprising a combination of component (a) and component (b), or a combination of component (a), component (b) and component (c), component (b) has the following: Glycolic acid; Glyoxylic acid; Citric acid; or Maleic anhydride; and wherein said component (c) comprises phosphoric acid, it has been found that the composition does not improve the demulsification efficiency of the composition consisting of component (a) of the present invention.

[0023] Thus, in one embodiment of the present invention, the composition comprises: Glycolic acid; Glyoxylic acid; Citric acid; or Maleic anhydride; does not contain one or more of the following:

[0024] In the present invention, the neutralized glyoxal is a glyoxal with a pH of neutral to basic. The inventors have observed that glyoxal is very acidic and may cause corrosion. Therefore, by neutralizing the glyoxal to a pH of neutral to basic, the corrosion of the crude oil processing unit is avoided and the demulsification efficiency of the demulsifier is further improved.

[0025] In the present invention, the neutralized glyoxal is obtained by neutralizing glyoxal with an amine or an alkaline medium.

[0026] In the present invention, the amine may include or comprise triethanolamine (TEA).

[0027] In the present invention, the alkaline medium may include or contain aqueous sodium hydroxide.

[0028] In the present invention, neutralized glyoxal may also include or include neutralized derivatives of glyoxal. Therefore, the terms "neutralized glyoxal" and "neutralized derivatives of glyoxal" in the present invention have the same meaning unless otherwise specified.

[0029] In the present invention, neutral to basic pH includes a pH of from about 7 to about 12.

[0030] In the present invention, glyoxal derivatives may include or comprise methanol, ethanol, butanol, or ethylene glycol derivatives of glyoxal, or mixtures thereof.

[0031] In a preferred embodiment of the present invention, the demulsifier is one of the following i) to vii): i) nonylphenol, amylphenol, and formaldehyde; ii) nonylphenol, butylphenol, and formaldehyde; iii) nonylphenol and formaldehyde; iv) amylphenol and formaldehyde; v) butylphenol and formaldehyde; vi) alkylphenols and formaldehyde; and vii) mixtures thereof; The oxyalkylenated condensation products of

[0032] In a preferred embodiment of the present invention, the demulsifier is one of the following i) to vii): i) cardanol, nonylphenol and amylphenol, and formaldehyde; ii) cardanol, nonylphenol and butylphenol, and formaldehyde; iii) cardanol, nonylphenol and formaldehyde; iv) cardanol, amylphenol and formaldehyde; v) Cardanol, butylphenol and formaldehyde; vi) cardanol, alkylphenols and formaldehyde; and vii) mixtures thereof; The oxyalkylenated condensation products of

[0033] In a preferred embodiment of the present invention, the demulsifier is one of the following i) to vii): i) oxyalkylated nonylphenol and amylphenol formaldehyde copolymers; ii) oxyalkylated nonylphenol and butylphenol formaldehyde copolymers; iii) oxyalkylated nonylphenol formaldehyde polymers; iv) oxyalkylated amylphenol formaldehyde polymers; v) oxyalkylated butylphenol formaldehyde polymers; vi) oxyalkylated alkylphenol formaldehyde polymers; and vii) Mixtures thereof The compound is selected from the group consisting of:

[0034] In a preferred embodiment of the present invention, the demulsifier is one of the following i) to vii): i) Oxyalkylated cardanol, nonylphenol and amylphenol, and formaldehyde copolymers; ii) oxyalkylated cardanol, nonylphenol and butylphenol, and formaldehyde copolymers; iii) oxyalkylated cardanol, nonylphenol and formaldehyde polymers; iv) oxyalkylated cardanol, amylphenol and formaldehyde polymers; v) oxyalkylated cardanol, butylphenol and formaldehyde polymers; vi) oxyalkylated cardanol, alkylphenol and formaldehyde polymers; and vii) Mixtures thereof The compound may be selected from the group including:

[0035] In a preferred embodiment of the present invention, the oxyalkylation product is an ethylene oxide derivative, a propylene oxide derivative, a butylene oxide derivative, or a mixture thereof. In a preferred embodiment of the present invention, the oxyalkylation product is an oxyalkylated copolymer, an oxyalkylated polymer, or an oxyalkylated resin. In a preferred embodiment of the present invention, the oxyalkylation product is a base-catalyzed oxyalkylated copolymer, a base-catalyzed oxyalkylated polymer, or a base-catalyzed oxyalkylated resin of one or more of the above phenolic compounds (i.e., cardanol, nonylphenol, butylphenol, amylphenol, alkylphenol) and formaldehyde. In a preferred embodiment of the present invention, the oxyalkylation product is an oxyalkylated phenol-formaldehyde resin, an oxyalkylated phenol-formaldehyde polymer, or an oxyalkylated phenol-formaldehyde copolymer.

[0036] In one embodiment of the invention, the phenolic reactant includes an alkylphenol containing an alkyl group. According to one of the embodiments of the invention, the alkyl group contains from about 1 to about 20 carbon atoms. In one embodiment of the invention, there may be substitution of butyl, amyl, nonyl, hexyl, octyl, isooctyl, decyl, or dodecyl groups.

[0037] It should be noted that the term "copolymer" means a polymer made from two different phenols and the term "polymer" means a polymer made from one phenol, and that resin is intended to encompass polymers and copolymers.

[0038] In one embodiment of the present invention, the reaction of an alkylphenol formaldehyde resin with an alkylene oxide forms a high molecular weight oxyalkylated alkylphenol formaldehyde resin.

[0039] In one embodiment of the invention, the alkylene oxide comprises ethylene oxide, propylene oxide, butylene oxide, or a mixture thereof, preferably, the alkylene oxide comprises ethylene oxide, propylene oxide, or a mixture thereof.

[0040] In a preferred embodiment of the present invention, the molecular weight of the demulsifier of the present invention may be about 1,000 to about 20,000 daltons, preferably about 2,000 to about 15,000 daltons, and more preferably about 2,000 to about 10,000 daltons, as measured by gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent.

[0041] In one embodiment of the present invention, the average molecular weight of the demulsifier of the present invention may be about 1,000 to about 2,000 daltons, preferably about 2,000 to about 15,000 daltons, and more preferably about 2,000 to about 15,000 daltons, as measured by gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent.

[0042] According to the invention, the composition may be prepared, depending on the nature of the water-in-oil emulsion to be treated: Component (a) ranges from about 99.1% to about 0.1% by weight of the total composition; Component (b) ranges from about 0.1% to about 99.1% by weight of the total composition; and Component (c) ranges from about 0.1% to about 99.1% by weight of the total composition; Includes.

[0043] It is noted that in the present invention, the additive composition can be added to the crude oil phase or to the desalter where the wash water is mixed with the crude oil to form a water-in-oil emulsion.

[0044] It should also be noted that the scope of the present invention is not limited by crude oil or wash water.

[0045] Thus, in another embodiment, the present invention relates to a method for demulsifying a water-in-oil emulsion, particularly a water-in-oil emulsion resulting from the mixing of wash water with crude oil, more particularly a water-in-oil emulsion resulting from the mixing of wash water with crude oil, in a desalter unit of a refinery, wherein the water-in-oil emulsion formed by the mixing of wash water in crude oil is treated with the demulsifier additive composition according to the present invention.

[0046] Thus, in yet another embodiment, the present invention also relates to a method of using the demulsifier additive composition of the present invention to demulsify water-in-oil emulsions, particularly water-in-oil emulsions resulting from the mixing of wash water with crude oil, more particularly water-in-oil emulsions resulting from the mixing of wash water with crude oil, in a desalter unit of a refinery, wherein the demulsifier additive composition of the present invention is added to the water-in-oil emulsion formed due to the mixing of wash water in the crude oil. The scope of the present invention is not limited by the amount of the demulsifier additive composition of the present invention added, as long as it is added in an amount sufficient to demulsify the water-in-oil emulsion.

[0047] The present invention will now be illustrated by the following examples, which are not intended to limit the scope of the invention, but are merely included to illustrate the advantages of the invention over the prior art. EXAMPLES

[0048] The following examples were carried out under the following conditions: PED No 1315 Crude: Raw Crude API: 28.1 Wash water: 5% (HMEL, ID443), pH-8.1 Mixing temperature: 550℃ Mixing time: 2 minutes Temperature: 130℃ Voltage: 3KV for 8 minutes

[0049] In the following examples, the following compositions were tested for demulsifying efficiency: 1. Component (a) is a demulsifier which is a 50% active nonylphenol formaldehyde ethoxylate resin (or it can be a base catalyzed nonylphenol formaldehyde resin). 2. Component (b) of the present invention is glyoxal or neutralized glyoxal, where the glyoxal is neutralized with triethanolamine (TEA). 3. Component (c) of the present invention is phosphoric acid; 4. The comparative ingredients can be selected from glycolic acid, glyoxylic acid, citric acid, and maleic anhydride, which in the following experiments are identified as follows and taken at 14% by weight DM (demineralized water). The comparative component (b1) is glycolic acid (40%); The comparative component (b2) is glyoxylic acid (40%); The comparative component (b3) is citric acid (40%); The comparative component (b4) is maleic anhydride (40%). 5. The comparative composition does not include the combination of components (b) and (c) of the present invention. The "blank" contains no additives.

[0050] [Table 1]

[0051] In Table I above, a dosage of "10+3" indicates that the additive contains 10 ppm of component (a) and 3 ppm of comparative component (b1), and so on. However, in Table 1 above, "the composition" contains 10 ppm of component (a) and 3 ppm of [component (b) + component (c)], where [component (b) + component (c)] contains component (b), which is glyoxal (40%), and component (c), which is H3PO4 (85%), in DM (demineralized water) water, in a mass ratio of 14 / 0.43 / 85.57.

[0052] As can be seen from Table I above, the efficiency of the composition of the present invention was 84% ​​compared to 56% or 74% for the comparative compositions.

[0053] [Table 2]

[0054] In Table II above, the dosage "10+3" indicates that the additive contains 10 ppm of component (a) and 3 ppm of a second component, i.e., Comparative Component (b1), Comparative Composition (B), Comparative Component (b2), Comparative Composition (C), Comparative Component (b3), Comparative Composition (D), Comparative Component (b4), Comparative Composition (E).

[0055] In Tables I and II above, the various ingredients have the following compositions: Component (a) is a 50% active nonylphenol formaldehyde ethoxylate resin (oxyalkylated condensation product). Component (b) contains glyoxal (40%) in 14% DM water. Component (c) contains H3PO4 (85%) in 0.43% DM water. In addition to component (a), the composition comprises component (b), which is glyoxal (40%) in DM water, and component (c), which is H3PO4 (85%), in a weight ratio of 14 / 0.43 / 85.57. The comparative component (b1) is glycolic acid (40%) in 14% DM water. Comparative composition (B) comprises comparative component (b1), which is glycolic acid (40%) in DM water, and component (c), which is H3PO4 (85%), in a weight ratio of 14 / 0.43 / 85.57. Comparative component (b2) is glyoxylic acid (40%) in 14% by weight DM water. Comparative composition (C) comprises comparative component (b2), which is glyoxylic acid (40%), and component (c), which is H3PO4 (85%), in DM water in a weight ratio of 14 / 0.43 / 85.57. Comparative component (b3) is citric acid (40%) in 14% by weight DM water. Comparative composition (D) comprises comparative component (b3), which is citric acid (40%), and component (c), which is H3PO4 (85%), in DM water in a weight ratio of 14 / 0.43 / 85.57. Comparative component (b4) is maleic anhydride (40%) in 14% by weight DM water. Comparative composition (E) comprises comparative component (b4), which is maleic anhydride (40%), and component (c), which is H3PO4 (85%) in DM water, in a weight ratio of 14 / 0.43 / 85.57.

[0056] As can be seen from Table II above, all comparative compositions have an efficiency of only 56% or 60%.

[0057] [Table 3]

[0058] In Table III, the mixing time was 2 minutes and the mixing temperature was 55° C. Component (b) is 0.9 ppm glyoxal (40%) in DM water and 0.9 ppm component (c) contains 0.87 ppm glyoxal (40%) in DM water and 0.03 ppm H3PO4 (85%) [i.e., 97% by weight glyoxal (40%) and 3% by weight H3PO4 (85%) in DM]; component (a) is 50% by weight active ethoxylated nonylphenol cardanol formaldehyde resin, which is an ethoxylated condensation product of 90% by weight nonylphenol and 10% by weight cardanol.

[0059] As can be seen from Table III above, the compositions of the present invention have an efficiency of 90% whereas the comparative compositions have an efficiency of 56% or 74%.

[0060] [Table 4]

[0061] In Table IV, the mixing time was again 2 minutes and the mixing temperature was again 55°C. Component (b) is 0.9 ppm of glyoxal (40%) in DM water. The 0.9 ppm of component (c) contains 0.846 ppm of glyoxal (40%) in DM and 0.054 ppm of H3PO4 (85%) [i.e., 84% by weight of glyoxal (40%) and 6% by weight of H3PO4 (85%) in DM]. Component (a) is a 50% active ethoxylated nonylphenol para-tertiary amyl phenol formaldehyde resin, which is an ethoxylated condensation product of 50% by weight nonylphenol and 50% by weight para-tertiary amyl phenol.

[0062] As can be seen from Table IV above, the efficiency of the composition of the present invention was 84% ​​whereas the efficiency of the comparative compositions was either 60% or 74%.

[0063] [Table 5]

[0064] In Table V, the mixing time was again 2 minutes and the mixing temperature was again 55°C. Component (b) is 1.2 ppm of glyoxal (40%) in DM water. The 1.2 ppm of component (c) contains 1.164 ppm of glyoxal (40%) in DM and 0.036 ppm of H3PO4 (85%) [i.e., 97% by weight of glyoxal (40%) and 3% by weight of H3PO4 (85%) in DM]. Component (a) is a 50% active ethoxylated nonylphenol para-tertiary butylphenol formaldehyde resin, which is an ethoxylated condensation product of 90% by weight nonylphenol and 10% by weight para-tertiary butylphenol.

[0065] As can be seen from Table IV above, the composition of the present invention exhibits an efficiency of 84% versus 56% or 74% for the comparative compositions.

[0066] In the above examples, the present additive compositions and prior art or comparative additive compositions were added to water-in-oil emulsions of water and crude oil formed after mixing of the water and crude oil.

[0067] The above experimental results confirm the above-mentioned surprising and unexpected technical advantages of the present invention. In particular, these experiments demonstrate the surprising and unexpected technical advantages of the present additive composition comprising component (a), inventive component (b) and inventive component (c).

[0068] As used herein, the term "about" is not intended to broaden the scope of the claimed invention, but is used only to encompass acceptable experimental error in the field of the invention.

Claims

1. 1. A demulsifying additive composition comprising: (a) at least one demulsifier comprising an oxyalkylated alkylphenol formaldehyde resin or an oxyalkylated condensation product of at least one alkylphenol with formaldehyde; and (b) a compound selected from the group consisting of glyoxal, neutralized glyoxal, ethylene glycol derivatives of glyoxal, and mixtures thereof; and (c) Phosphoric acid Including, Wherein the oxyalkylated alkylphenol formaldehyde resin includes oxyalkylated alkylphenol formaldehyde polymer and oxyalkylated alkylphenol formaldehyde copolymer; and The pH of the neutralized glyoxal is in the range of neutral to basic glyoxal. Demulsifying additive composition.

2. 2. The demulsifying additive composition of claim 1, wherein the neutralized glyoxal has a pH of 7 to 12.

3. The demulsifier is i) nonylphenol, amylphenol, and formaldehyde; ii) nonylphenol, butylphenol, and formaldehyde; iii) nonylphenol and formaldehyde; iv) amylphenol and formaldehyde; v) butylphenol and formaldehyde; vi) alkylphenols and formaldehyde, and vii) mixtures thereof; 3. The demulsifying additive composition of claim 1 or 2, wherein the oxyalkylated condensation products of

4. The demulsifier is i) cardanol, nonylphenol, amylphenol, and formaldehyde; ii) cardanol, nonylphenol, butylphenol, and formaldehyde; iii) cardanol, nonylphenol and formaldehyde; iv) cardanol, amylphenol and formaldehyde; v) cardanol, butylphenol and formaldehyde; vi) cardanol, an alkylphenol and formaldehyde, or vii) mixtures thereof; The demulsifying additive composition of any one of claims 1 to 3, wherein the oxyalkylated condensation products of

5. The demulsifying additive composition of any one of claims 1 to 4, wherein the oxyalkyl is a derivative of ethylene oxide, propylene oxide, or a mixture thereof.

6. The demulsifier may be selected from the group consisting of: i) copolymers of oxyalkylated nonylphenol and amylphenol formaldehyde; ii) copolymers of oxyalkylated nonylphenol and butylphenol formaldehyde; iii) Polymers of oxyalkylated nonylphenol and formaldehyde; iv) polymers of oxyalkylated amylphenol and formaldehyde; v) polymers of oxyalkylated butylphenol and formaldehyde; vi) polymers of oxyalkylated alkylphenols and formaldehyde; and vii) mixtures thereof; The demulsifying additive composition of any one of claims 1 to 5, selected from the group consisting of:

7. The demulsifier is i) copolymers of oxyalkylated cardanol, nonylphenol and amylphenol, and formaldehyde; ii) copolymers of oxyalkylated cardanol, nonylphenol and butylphenol, and formaldehyde; iii) Polymers of oxyalkylated cardanol, nonylphenol and formaldehyde; iv) Polymers of oxyalkylated cardanol, amylphenol and formaldehyde; v) Polymers of oxyalkylated cardanol, butylphenol and formaldehyde; vi) polymers of oxyalkylated cardanol, alkylphenols and formaldehyde; and vii) mixtures thereof; The method according to any one of claims 1 to 6, wherein the compound is selected from the group consisting of:

8. The composition may be prepared according to the nature of the water-in-oil emulsion to be treated. component (a) is from 99.1% to 0.1% by weight of the total composition; Component (b) is from 0.1% to 99.1% by weight of the total composition; and Component (c) is 0.1% to 99.1% by weight of the total composition; The demulsifying additive composition according to any one of claims 1 to 7.

9. 9. The demulsifier additive composition of claim 1, wherein the molecular weight of the demulsifier is in the range of 1,000 to 20,000 Daltons as measured by gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent.

10. below, (i) glycolic acid, (ii) glyoxylic acid, (iii) citric acid, and (iv) maleic anhydride, The demulsifying additive composition of any one of claims 1 to 9, which does not comprise

11. 1. A method for demulsifying a water-in-oil emulsion, comprising treating the water-in-oil emulsion with a demulsifying additive composition, the demulsifying additive composition comprising: (a) at least one demulsifier comprising an oxyalkylated alkylphenol formaldehyde resin or an oxyalkylated condensation product of at least one alkylphenol with formaldehyde; and (b) a compound selected from the group consisting of glyoxal, neutralized glyoxal, ethylene glycol derivatives of glyoxal, and mixtures thereof; and (c) Phosphoric acid Including, Wherein, the oxyalkylated alkylphenol formaldehyde resin includes oxyalkylated alkylphenol formaldehyde polymer and oxyalkylated alkylphenol formaldehyde copolymer; method.

12. A method for demulsifying a water-in-oil emulsion, comprising treating the water-in-oil emulsion with the demulsifying additive composition according to any one of claims 1 to 10.

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