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EP0074592A2 - Bisamides, procédés pour leur préparation et leur utilisation - Google Patents

Bisamides, procédés pour leur préparation et leur utilisation Download PDF

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Publication number
EP0074592A2
EP0074592A2 EP82108171A EP82108171A EP0074592A2 EP 0074592 A2 EP0074592 A2 EP 0074592A2 EP 82108171 A EP82108171 A EP 82108171A EP 82108171 A EP82108171 A EP 82108171A EP 0074592 A2 EP0074592 A2 EP 0074592A2
Authority
EP
European Patent Office
Prior art keywords
formula
bis
oder
group
hydrogen
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.)
Withdrawn
Application number
EP82108171A
Other languages
German (de)
English (en)
Other versions
EP0074592A3 (fr
Inventor
Werner Dr. Ritschel
Helmut Dr. Diery
Martin Dr. Hille
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0074592A2 publication Critical patent/EP0074592A2/fr
Publication of EP0074592A3 publication Critical patent/EP0074592A3/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G33/00—Dewatering or demulsification of hydrocarbon oils
    • C10G33/04—Dewatering or demulsification of hydrocarbon oils with chemical means

Definitions

  • the task of a demulsifier is to break the emulsion at the lowest possible application concentration and, in this separation process, to achieve complete water separation without expenditure or with minimal additional heat, and to reduce the salt content to a minimum.
  • the quality criteria for delivered crude oil are the residual salt content and the water content.
  • the crude oils have different compositions depending on their provinces and the natural emulsion stabilizers in the oil have a complicated and differentiated chemical structure, so that splitters have to be developed for each one. Due to different funding and processing conditions, the demands placed on a demulsifier are even more diverse. By constantly opening up new and changing the production conditions of older oil fields, the development of optimal demulsifiers for the respective purpose remains an acute task.
  • the compounds of the above formula are prepared by firstly using a dimerized fatty acid of the formula II with a compound of formula III condensed to a compound of formula IV, this compound of the formula IV optionally reacted with ethylene oxide and / or propylene oxide or butylene oxide, the reaction product obtained with an acid of the formula V. esterified and then optionally neutralized or quaternized.
  • Preferred dimerized fatty acids are the products which are commercially available under the names (R) Fripol 1010, (R) pripol 1022 and Fatty Acid 7002. See also RW Johnson in "Fatty acids" These products can also contain parts of trimeric or higher condensed fatty acids. For example, Pr ip ol L022 20% contains trimeric shares and p r ip ol 1010 only about 3%.
  • the dimerized fatty acids are first condensed with two moles of a compound of formula III.
  • Such compounds are, for example, aminoethylethanolamine, diethanolamine., Propylene diamine, alkyl propylene diamine, ethylene diamine, diethylene triamine, triethylene tetramine, tetramethylene pentamine, pentaethylene hexamine, mixed ethylene / propylene polyamines such as 3- (2-aminoethyl) aminopropylamine, N, N'-bis- (3 ) ethylenediamine.
  • the condensation can take place without solvent in the melt of the reactants or in the presence of an inert solvent at the boiling point of the solvent.
  • the solvent used here is preferably toluene or xylene, which also serves to remove the water of reaction formed.
  • the bisamide of formula IV formed in this condensation can then be alkoxylated by known methods, preferably in the presence of a basic catalyst such as sodium methylate or sodium hydroxide.
  • a basic catalyst such as sodium methylate or sodium hydroxide.
  • Preferred alkylene oxides are ethylene oxide, but also mixtures of ethylene oxide with propylene oxide or butylene oxide.
  • oxyalkylation products or the bisamides of the formula IV are then esterified with one or more carboxylic acids of the formula V.
  • C a -C 22 fatty acids are preferably used as carboxylic acids.
  • the quantitative ratio between carboxylic acids and bisamides of the formula IV or its oxyalkylation products can be chosen so that one or more acyl groups are present in the ester.
  • the esterification can be carried out with pure carboxylic acids of the formula V or with mixtures of various such carboxylic acids. Analogous to the first stage, the reaction can also be carried out in the melt of the reactants are at temperatures of approx. 160 - 180 ° C or in an inert solvent as described above.
  • alkylating reagents such as e.g. Methyl chloride, benzyl chloride, dimethyl sulfate or trimethyl phosphate, preferably at temperatures of 60 - 70 ° C in a lower alcohol or in toluene.
  • the products obtained in this way are very suitable for demulsifying crude oil emulsions both in the quaternized and in the partially or non-quaternized or neutralized form.
  • These crude oil emulsion products are added in a concentration of 2 to 400, preferably 5 to 50 ppm, either in undiluted form or as solutions which are diluted in a ratio of up to 1: 200 with an organic solvent.
  • R means the alkyl skeleton of a dimerized fatty acid with 34 carbon atoms.
  • the bisamide IVd is heated in a distillation apparatus with 500 g (2 mol) of tallow fatty acid until 35 ml of H 2 O have been distilled off. Then 1030 g of isobutanol are added and 120 g (2 mol) of glacial acetic acid are added dropwise at 60.degree. The acetate is obtained as a 50% solution in isobutanol.
  • the compounds of the invention of raw b lemulsionen shown at the usual conditions in the oil fields and amounts used.
  • the demulsifiers were injected as 50% isobutanolic solutions with microdosing devices.
  • the emulsified water is separated in conical, calibrated, stopper-closable glasses and the amount of emulsion used is 100 em 3 each.
  • the amounts of emulsion water separated in certain times are given in%.
  • the absolute water content of the emulsions was determined according to Dean-Stark by means of preliminary tests.
  • the dosing quantity of the demulsifiers, the absolute water content of the emulsion, the separation temperature and the origin of the emulsion are listed in the individual tables.
  • the corrosion-inhibiting action of the compounds according to the invention is determined by the weight loss of test coupons with a surface area of 20 cm 2 in 20% sodium chloride solution over 6 hours at 60 ° C. A stream of carbon dioxide constantly bubbles through the stirred, saline solution. Table 4 shows the inhibitory activity in%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
EP82108171A 1981-09-10 1982-09-04 Bisamides, procédés pour leur préparation et leur utilisation Withdrawn EP0074592A3 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3135832 1981-09-10
DE19813135832 DE3135832A1 (de) 1981-09-10 1981-09-10 Bisamide, verfahren zu deren herstellung und deren verwendung

Publications (2)

Publication Number Publication Date
EP0074592A2 true EP0074592A2 (fr) 1983-03-23
EP0074592A3 EP0074592A3 (fr) 1984-03-21

Family

ID=6141287

Family Applications (1)

Application Number Title Priority Date Filing Date
EP82108171A Withdrawn EP0074592A3 (fr) 1981-09-10 1982-09-04 Bisamides, procédés pour leur préparation et leur utilisation

Country Status (6)

Country Link
US (1) US4536339A (fr)
EP (1) EP0074592A3 (fr)
JP (1) JPS5857348A (fr)
BR (1) BR8205283A (fr)
DE (1) DE3135832A1 (fr)
NO (1) NO823067L (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1865013A1 (fr) * 2006-06-09 2007-12-12 Air Products and Chemicals, Inc. Compositions d'agent durcissables en polyamide
US7655736B2 (en) 2006-06-09 2010-02-02 Air Products And Chemicals, Inc. Polyamide curative from substituted amine mixture and dimer fatty acid or ester

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4946625A (en) * 1989-03-27 1990-08-07 Siltech Inc. Particulate defoaming compositions
US7105628B2 (en) 2002-08-27 2006-09-12 Acushnet Company Compositions for golf equipment
DE10109845A1 (de) * 2001-03-01 2002-09-05 Basf Ag Emulgatoren, insbesondere auf Basis von Polyisobutylenaminen
US7098274B2 (en) 2002-08-27 2006-08-29 Acushnet Company Compositions for golf equipment
US7014574B2 (en) * 2002-07-15 2006-03-21 Acushnet Company Compositions for golf balls
US7138477B2 (en) * 2002-08-27 2006-11-21 Acushnet Company Compositions for golf equipment
US7138476B2 (en) 2002-08-27 2006-11-21 Acushnet Company Compositions for golf equipment
US7138475B2 (en) 2002-08-27 2006-11-21 Acushnet Company Compositions for golf equipment
US7105623B2 (en) 2002-08-27 2006-09-12 Acushnet Company Compositions for golf equipment
US7157545B2 (en) * 2002-08-27 2007-01-02 Acushnet Company Compositions for golf equipment
US7378483B2 (en) 2002-08-27 2008-05-27 Acushnet Company Compositions for golf equipment
US7115703B2 (en) 2002-08-27 2006-10-03 Acushnet Company Compositions for golf equipment
US7101951B2 (en) 2002-08-27 2006-09-05 Acushnet Company Compositions for golf equipment
US7253245B2 (en) 2004-06-02 2007-08-07 Acushnet Company Compositions for golf equipment
US7253242B2 (en) 2004-06-02 2007-08-07 Acushnet Company Compositions for golf equipment
US7276570B2 (en) 2004-06-02 2007-10-02 Acushnet Company Compositions for golf equipment
US7256249B2 (en) 2004-06-02 2007-08-14 Acushnet Company Compositions for golf equipment
US7265195B2 (en) 2004-06-02 2007-09-04 Acushnet Company Compositions for golf equipment
US20070287808A1 (en) * 2006-06-09 2007-12-13 Gamini Ananda Vedage Polyamide curing agent compositions
US7745501B2 (en) * 2006-06-22 2010-06-29 Momentive Performance Materials Inc. Method for demulsifying
US8030363B2 (en) 2008-01-25 2011-10-04 Momentive Performance Materials Inc. Polyorganosiloxane demulsifier compositions and methods of making the same

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3308076A (en) * 1961-07-28 1967-03-07 Interchem Corp Polyamides produced from polyepoxides, dimeric fatty acids and polyamines
FR2180481B1 (fr) * 1972-04-18 1974-12-20 Raffinage Cie Francaise
US4072641A (en) * 1975-10-28 1978-02-07 Kraftco Corporation Polyamide resins and method for manufacture
US4344861A (en) * 1980-01-15 1982-08-17 Uop Inc. Bis-amides as corrosion inhibitors

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1865013A1 (fr) * 2006-06-09 2007-12-12 Air Products and Chemicals, Inc. Compositions d'agent durcissables en polyamide
US7655736B2 (en) 2006-06-09 2010-02-02 Air Products And Chemicals, Inc. Polyamide curative from substituted amine mixture and dimer fatty acid or ester
US8293863B2 (en) 2006-06-09 2012-10-23 Air Products And Chemicals, Inc. Polyamide curative from substituted amine and dimer fatty acid or ester

Also Published As

Publication number Publication date
EP0074592A3 (fr) 1984-03-21
JPS5857348A (ja) 1983-04-05
DE3135832A1 (de) 1983-03-24
NO823067L (no) 1983-03-11
US4536339A (en) 1985-08-20
BR8205283A (pt) 1983-08-16

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Effective date: 19840525

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18W Application withdrawn

Withdrawal date: 19850517

RIN1 Information on inventor provided before grant (corrected)

Inventor name: DIERY, HELMUT, DR.

Inventor name: RITSCHEL, WERNER, DR.

Inventor name: HILLE, MARTIN, DR.