EP0332002B2 - Utilisation de copolymères sélectionnés d'esters d'acides acryliques ou/et méthacryliques, comme agents modifiant l'écoulement dans des pétroles et fractions (II) de pétroles riches en paraffine - Google Patents

Utilisation de copolymères sélectionnés d'esters d'acides acryliques ou/et méthacryliques, comme agents modifiant l'écoulement dans des pétroles et fractions (II) de pétroles riches en paraffine Download PDF

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Publication number
EP0332002B2
EP0332002B2 EP89103385A EP89103385A EP0332002B2 EP 0332002 B2 EP0332002 B2 EP 0332002B2 EP 89103385 A EP89103385 A EP 89103385A EP 89103385 A EP89103385 A EP 89103385A EP 0332002 B2 EP0332002 B2 EP 0332002B2
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EP
European Patent Office
Prior art keywords
copolymers
flow
methacrylic acid
alcohol
esters
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP89103385A
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German (de)
English (en)
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EP0332002B1 (fr
EP0332002A2 (fr
EP0332002A3 (en
Inventor
Wolfgang Dr. Ritter
Claudia Meyer
Wolfgang Zöllner
Claus-Peter Dr. Herold
Stephan Dr. Von Tapavicza
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BASF Personal Care and Nutrition GmbH
Original Assignee
Henkel AG and Co KGaA
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes
    • C10L10/14—Use of additives to fuels or fires for particular purposes for improving low temperature properties
    • C10L10/16—Pour-point depressants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/192—Macromolecular compounds
    • C10L1/195—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/196—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1963—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S507/00—Earth boring, well treating, and oil field chemistry
    • Y10S507/927—Well cleaning fluid
    • Y10S507/929—Cleaning organic contaminant
    • Y10S507/93—Organic contaminant is asphaltic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S507/00—Earth boring, well treating, and oil field chemistry
    • Y10S507/927—Well cleaning fluid
    • Y10S507/929—Cleaning organic contaminant
    • Y10S507/931—Organic contaminant is paraffinic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T137/00—Fluid handling
    • Y10T137/0318—Processes
    • Y10T137/0391—Affecting flow by the addition of material or energy

Definitions

  • auxiliaries which are also referred to as paraffin inhibitors and are generally prepared by polymerizing olefinic unsaturated compounds which contain at least partially unbranched saturated hydrocarbon chains with at least 18 carbon atoms.
  • DE-A-2 264 328 describes the use of copolymers of acrylic and / or methacrylic esters of higher alcohols or alcohol cuts with at least 16 carbon atoms in the alcohol residue as additives for crude oils and petroleum fractions to reduce their flow properties.
  • the copolymers of DE-A-2 264 328 obviously do not contain any free acrylic acid or methacrylic acid.
  • Example 1 of DE-A-2 264 328 expressly uses equimolar amounts of alcohol and acrylic acid.
  • DE-PS 30 31 900 describes copolymers of n-alkyl acrylates with at least 16 carbon atoms in the alcohol residue and maleic anhydride with molar ratios of n-alkyl acrylate to maleic anhydride from 20 1 to 1:10. Compounds of this type are said to be used as crystallization inhibitors for paraffin-containing crude oils. Examples shown numerically relate to the use of corresponding copolymers in the molar ratio of the acrylic acid ester to maleic anhydride in the range from 1: 1 to 8: 1. Crude oils with intrinsic pour points below 20 ° C. are predominantly used.
  • a table of values deals with India crude oil, which is known to be a particularly paraffin-rich starting material (disruptive paraffin content 15%) and has an intrinsic pour point of 33 ° C.
  • the optimum effectiveness of the copolymers used in this publication with regard to reducing the pour point on this starting material is at the molar ratio of acrylic acid ester / maleic anhydride of 4: 1.
  • the lowest pour points set here are at 12 ° C. If the proportion of maleic anhydride in the copolymer is further reduced, then the pour points of the India crude oil thus added rise again with the addition of the same amount (cf. in particular Table 2 of the cited literature reference).
  • JP-A-59 108 095 teaches the use of homo-, co- and / or graft polymers of monomers selected from long-chain ⁇ -olefins, unsaturated carboxylic acids and alkyl esters of unsaturated carboxylic acids to delay the phase separation in hydrocarbon mixtures, the solids as a suspension or other additives Form of liquids of higher polarity included.
  • a solution to the pour point depression problem is not disclosed or suggested.
  • the teaching of the present invention is based on knowledge. that a particularly effective lowering of the hardening temperatures - determined according to the known methods of pour point and / or pour point determination - as well as an effective improvement in the flow behavior can be obtained just in the temperature range just above the lowered pour points if the copolymer types described below in detail from acrylic and / or methacrylic acid esters of higher alcohols and free acrylic acid and / or methacrylic acid are used in limited amounts as comonomers for the purpose of lowering the pour point.
  • copolymers of acrylic and / or methacrylic acid esters of higher alcohols or alcohol cuts with at least 16 carbon atoms in the alcohol residue and 0.5 to 15% by weight, based on the copolymer weight, of free acrylic acid and / or methacrylic acid as Additive for crude oils and petroleum fractions containing paraffins and / or asphaltenes to lower their pour point or solidification point and improve the flow properties, especially in the temperature range just above the solidification point.
  • the teaching of the invention characterized in that copolymers based on esters from alcohols or alcohol cuts with predominantly 18 to 24 C atoms are used, the content of C 22 and higher alcohols of which is at least 45% by weight.
  • Particularly suitable copolymers of the type mentioned contain, together with the acrylic and / or methacrylic acid esters of higher alcohols or alcohol cuts, 1 to 10% by weight of the free acids mentioned.
  • the most important copolymers of the type used in accordance with the invention contain acrylic acid and / or methacrylic acid as comonomers in the copolymer shown above in amounts of about 1.5 to 5.0% by weight. All these percentages by weight relate to the copolymer weight.
  • the additives of the invention which lower the pour point and improve the flow properties of the treated oils or oil fractions can very advantageously be used in general for crude oils or petroleum fractions of any origin. Their use is particularly helpful in the problems described at the beginning of the paraffin-rich crude oils and / or petroleum fractions with their own pour points above 20 ° C and in particular above 25 ° C.
  • the use of the pour point improvers according to the invention in only limited quantities makes it possible to lower the pour points to values below 15 ° C. and preferably to values below 10 ° C. even with these feedstocks. This is possible even if the starting or.
  • the self-pour points of the oils or oil fractions are at 30 ° C or above.
  • pour point improvers it is thus possible, by adding conventional amounts of the pour point improvers, to obtain pour points in the range from about 0 to 8 ° C. even with extremely paraffin-rich starting materials. This ensures trouble-free handling of these crude oils and oil fractions under normal everyday conditions. In particular, it is ensured that lines, distributors and the like which are guided under water can be operated without problems.
  • the weight percentages given here relate to the content of C 22 alcohol - and possibly higher alcohols - in the alcohol mixture that was used for the production of the acrylate components
  • the application concentration of the pour point improver according to the invention is in the conventional range and is, for example, 20 to 1000 ppm, with amounts in the range from 100 to 500 ppm being preferred.
  • the pour point improvers are expediently used in suitable solvents. Details on this and on the preparation of the copolymers can be found in the relevant prior art, for example in DE-PS 30 31 900 already cited.
  • the alcohols or alcohol cuts used for the production of the acrylate components can be of native or synthetic origin. Alcohol cuts with a predominant proportion of components with at least 22 carbon atoms, but at the same time also minor amounts of alcohol components in the range C 16 to C 20 , are the preferred starting materials.
  • the two acrylate ester mixtures A and B are used, which differ in the C chain distribution of the fatty alcohol mixture used for the acrylic acid esterification.
  • the two types of acrylate are characterized as follows: Table 1 C chain distribution of fatty alcohol /% C 16 C 18 C 20 C 22 Acrylate A 16.3 22.9 10.7 46.9 Acrylate B 1.5 8.6 15.2 68.8
  • Two types of processes are used to produce the acrylate / acrylic acid copolymers, the batch process and the feed process.
  • the monomers, initiator and solvent are weighed into a three-necked flask.
  • the batch is evacuated for 10 ⁇ 1 min and the vacuum is released again with 99.999% nitrogen.
  • the batch is heated to 90 ° C. and kept at this temperature.
  • the entire reaction is carried out under inert conditions.
  • the start of the reaction manifests itself in a temperature rise to 93 to 96 ° C.
  • the mixture is kept at 90 ° C ⁇ 1 ° C for 3 h. After this time, the mixture is cooled to room temperature within 45 minutes and the product is filled.
  • Toluene is used as the solvent here and in the subsequent feed process.
  • the polymerization initiator used is dibenzoyl peroxide or azoisobutyronitrile as indicated below.
  • the mixing ratio of solvent to monomer mixture is 1: 1 (parts by weight).
  • the monomers are dissolved in toluene in the desired mixing ratio at 45 to 50 ° C. and the solution is then cooled to 25 ° C.
  • the initiator is also used in solution in toluene. About 20% of the monomer solution determined per batch is placed in a reactor. The reactor is flushed three times with nitrogen and heated to 90 ° C. while stirring under a gentle stream of N 2 . The initiator solution is now metered in so that the total metering time is 2.5 hours.
  • a temperature increase occurs 20 minutes after the initiator has been added.
  • the temperature is kept at 90 ⁇ 3 ° C by cooling the reactor jacket.
  • the remaining monomer solution is metered into the reactor in such a way that the total metering time is 2 h.
  • the temperature is kept at 90 ⁇ 3 ° C throughout the reaction time.
  • the reaction mixture is then kept at the same temperature for a further 60 min.
  • the reaction product is then cooled and filled at 30 ° C.
  • Examples 1 to 12 according to the invention are summarized in Table 2 below.
  • the type of acrylate monomers A or B used is assigned to the respective example and the percentage (% by weight) of acrylic acid in the monomer mixture for the preparation of the pour point depressant is given.
  • the flow improver was produced by the batch process and in examples 2 to 12 by the feed process.
  • Table 2 finally shows the specific viscosity of the copolymer solutions prepared in each case.
  • the viscosity is measured using an Ubbelohde viscometer, capillary 1, ⁇ 0.63 mm.
  • the measured toluene solutions are 3% solutions in toluene. The measurement is carried out at 20 ° C after a temperature adjustment of 10 min.
  • Table 2 contains the pour point values which were obtained when the pour point improvers according to the invention were added to an India crude (Bombay crude oil) in accordance with the following working instructions.
  • the pour point was determined in accordance with ASTM D 97-66 and DIN 51597 as follows:
  • the pour point of the untreated Bombay crude oil is 30 ° C according to this determination method.
  • the technical advantage of the flow improver according to the invention can be seen from this.
  • the pump pressure that has to be applied to start up a pipeline filled with cooled crude oil is 48 times after 2 hours and still 20 times after working according to the teaching of the invention for the market product that has also been tested.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Emergency Medicine (AREA)
  • Health & Medical Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Lubricants (AREA)
  • Polymerisation Methods In General (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Claims (6)

  1. Utilisation de copolymères à base d'esters d'acide acrylique et/ou d'acides méthacryliques et d'alcools supérieurs ou de coupes d'alcools ayant au moins 16 atomes de carbone dans le radical alcool et de 0,5 à 15 % en, poids - rapporté au poids de copolymère - en acide acrylique libre et/ou acide méthacrylique en tant qu'agent d'addition pour des huiles brutes ou des fractions pétrolières contenant des paraffines et/ou de l'asphaltine, en vue de l'abaissement de leur point de solidification ou d'écoulement et de l'amélioration des propriétés d'écoulement, en particulier dans une zone de températures un peu au-dessus du point de solidification,
       caractérisée en ce que,
       on utilise des copolymères à base d'esters provenant d'alcools ou coupes d'alcools avec principalement 18 à 24 atomes de carbone, dont la teneur en alcools en C22 et en alcools supérieurs constitue au moins 45 % en poids.
  2. Utilisation selon la revendication 1,
       caractérisée en ce que,
       sont utilisés les copolymères du type indiqué avec des teneurs en acides libres dans la zone d'environ 1 à 10 % en poids, de préférence dans la zone de 1,5 à 5 % en poids, rapporté au poids de copolymère.
  3. Utilisation selon les revendications 1 et 2,
       caractérisée en ce que,
       les agents améliorant l'écoulement dans des huiles ou des fractions d'huile riches en paraffines avec des points d'écoulement particuliers au-dessus de 20°C, en particulier au-dessus de 25°C entrent en action et en ce que de préférence avec cela les points d'écoulement sont abaissés à des valeurs en dessous de 15°C, en particulier en dessous de 10°C.
  4. Utilisation selon les revendications 1 à 3,
       caractérisée en ce que,
       sont utilisés des copolymères à base d'esters d'alcools ou de coupes d'alcools, dont la teneur en alcools en C22 et en alcools supérieurs, se situe au-dessus de 50 % en poids.
  5. Utilisation selon les revendications 1 à 4,
       caractérisée en ce que,
       l'on met en oeuvre des copolymères à base d'esters d'acide acrylique avec des alcools ou des coupes d'alcools supérieurs du type mentionné et d'acide acrylique libre.
  6. Utilisation selon les revendications 1 à 5,
       caractérisée en ce que,
       l'on met en oeuvre les agents qui améliorent l'écoulement en quantités qui vont d'environ 20 à 1 000 ppm et pour cela de préférence dissous dans des solvants.
EP89103385A 1988-03-07 1989-02-27 Utilisation de copolymères sélectionnés d'esters d'acides acryliques ou/et méthacryliques, comme agents modifiant l'écoulement dans des pétroles et fractions (II) de pétroles riches en paraffine Expired - Lifetime EP0332002B2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3807395A DE3807395A1 (de) 1988-03-07 1988-03-07 Verwendung ausgewaehlter copolymertypen der acryl- und/oder methacrylsaeureester als fliessverbesserer in paraffinreichen erdoelen und erdoelfraktionen (ii)
DE3807395 1988-03-07

Publications (4)

Publication Number Publication Date
EP0332002A2 EP0332002A2 (fr) 1989-09-13
EP0332002A3 EP0332002A3 (en) 1990-03-28
EP0332002B1 EP0332002B1 (fr) 1992-04-15
EP0332002B2 true EP0332002B2 (fr) 1997-05-02

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EP89103385A Expired - Lifetime EP0332002B2 (fr) 1988-03-07 1989-02-27 Utilisation de copolymères sélectionnés d'esters d'acides acryliques ou/et méthacryliques, comme agents modifiant l'écoulement dans des pétroles et fractions (II) de pétroles riches en paraffine

Country Status (11)

Country Link
US (1) US5039432A (fr)
EP (1) EP0332002B2 (fr)
JP (1) JPH01287393A (fr)
AU (1) AU611265B2 (fr)
BR (1) BR8901034A (fr)
CA (1) CA1327538C (fr)
DE (2) DE3807395A1 (fr)
DK (1) DK110789A (fr)
MX (1) MX171036B (fr)
NO (1) NO176413C (fr)
TR (1) TR24478A (fr)

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Publication number Publication date
US5039432A (en) 1991-08-13
DE3807395A1 (de) 1989-09-21
DK110789D0 (da) 1989-03-07
AU3102589A (en) 1989-09-07
JPH01287393A (ja) 1989-11-20
NO176413C (no) 1995-03-29
DK110789A (da) 1989-09-08
AU611265B2 (en) 1991-06-06
EP0332002B1 (fr) 1992-04-15
EP0332002A2 (fr) 1989-09-13
NO890938D0 (no) 1989-03-06
BR8901034A (pt) 1989-10-24
MX171036B (es) 1993-09-27
CA1327538C (fr) 1994-03-08
NO176413B (no) 1994-12-19
DE58901132D1 (de) 1992-05-21
EP0332002A3 (en) 1990-03-28
NO890938L (no) 1989-09-08
TR24478A (tr) 1991-10-11

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