DE1570320A1 - Process for the production of oil-soluble condensation products - Google Patents
Process for the production of oil-soluble condensation productsInfo
- Publication number
- DE1570320A1 DE1570320A1 DE19651570320 DE1570320A DE1570320A1 DE 1570320 A1 DE1570320 A1 DE 1570320A1 DE 19651570320 DE19651570320 DE 19651570320 DE 1570320 A DE1570320 A DE 1570320A DE 1570320 A1 DE1570320 A1 DE 1570320A1
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- oil
- condensation products
- amount
- soluble condensation
- 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.)
- Pending
Links
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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G10/00—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only
- C08G10/02—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only of aldehydes
- C08G10/04—Chemically-modified polycondensates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
BADISGHE ANILIN- & SODA-PABRIK AG ι r ^7 n <■» η r»BADISGHE ANILIN- & SODA-PABRIK AG ι r ^ 7 n <■ »η r»
I 0 / U ο 2 I 0 / U ο 2
Dr. ExpL!Dr. ExpL!
Unsere Zeichen: O.Z. 24 015 Mi/Bö /Du Ludwigshafen/Rhein, den 6.12.1965Our symbols: O.Z. 24 015 Wed / Bo / Du Ludwigshafen / Rhine, December 6th, 1965
Verfahren zur Herstellung öllöslicher KondensationsprodukteProcess for the preparation of oil-soluble condensation products
Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung neuer öllöslicher Kondensationsprodukte auf der Grundlage von Dialkylbenzolen und Formaldehyd.The present invention relates to a method of manufacture new oil-soluble condensation products based on dialkylbenzenes and formaldehyde.
Es ist "bekannt, daß man durch Umsetzung von Dialkylbenzclen und Formaldehyd verhältnismäßig niedermolekulare Kondensationsprodukte erhält. Näheres hierzu ist dem zusammenfassenden Artikel "Über die Kondensation aromatischer Verbindungen mit Formaldehyd" in der Zeitschrift für Angewandte Chemie, 60 (1948), Seite 88 f zu entnehmen.-It is "known that by reacting dialkylbenzene and Formaldehyde is a relatively low molecular weight condensation product receives. For more information, see the summarizing article "About the condensation of aromatic compounds with formaldehyde" in the Zeitschrift für Angewandte Chemie, 60 (1948), page 88 f.
Es wurde nun gefunden, daß man hochwertige öllösliche Kondensationsprodukte auf der Grundlage von Dialkylbenzolen und Formaldehyd erhält, wenn manIt has now been found that high quality oil-soluble condensation products can be obtained obtained on the basis of dialkylbenzenes and formaldehyde if one
a) 1 Mol eines Dialkylbenzols, dessen Alkylgruppen bis zu je 20 C-Atome enthalten können, unda) 1 mole of a dialkylbenzene, the alkyl groups of which can contain up to 20 carbon atoms, and
b) 1,5 bis 6 Mol Formaldehyd oder einer entsprechenden Menge einer stickstofffreien Verbindung, die Formaldehyd abspalten kann,b) 1.5 to 6 moles of formaldehyde or a corresponding amount of a nitrogen-free compound which split off formaldehyde can,
-2--2-
009810/1599009810/1599
-2- O.Z. 24 015-2- O.Z. 24 015
bei Temperaturen zwischen 70 und 1800C, vorzugsweise zwischen und 12O0C, in an sich bekannter Weise mit Hilfe einer Säure als Katalysator miteinander umsetzt und das so erhaltene Reakticnsprodukt neutralisiert oder von der darin enthaltenen Säure durch Auswaschen befreit und danach mitat temperatures between 70 and 180 0 C, preferably between and 12O 0 C, in a known manner with the aid of an acid as a catalyst and neutralized the thus obtained Reakticnsprodukt or freed from the acid contained therein by washing out and then with
c) der 10-, bis 40-fachen, vorzugsweise 25- bis 35-fachen Gewichtsmenge, bezogen auf die Menge des aus den Komponenten (a) und (b) erhaltenen Produkts, Äthylenoxyd und/oder Propylenoxyd c) 10 to 40 times, preferably 25 to 35 times the amount by weight, based on the amount of the product obtained from components (a) and (b), ethylene oxide and / or propylene oxide
in an sich bekannter Weise umsetzt.implemented in a manner known per se.
Als Ausgangsverbindungen (a) eignen sich o-, m- und p-Dialkylbenzole wie die Xylole, Diäthylbenzole, Methyläthylbenzole, Diisopropylbenzole und Methylisopropylbenzole; neben diesen wohlfeilen Verbindungen kommen auch Verbindungen mit höheren Alkylresten in Betracht, z.B. p-Methylnonyl- und p-Methyldodecylbenzol.Suitable starting compounds (a) are o-, m- and p-dialkylbenzenes like the xylenes, diethylbenzenes, methylethylbenzenes, diisopropylbenzenes and methylisopropylbenzenes; In addition to these inexpensive compounds, compounds with higher alkyl radicals also come into play Consider, e.g., p-methylnonyl and p-methyldodecylbenzene.
Neben Formaldehyd als Verbindung (b) kommen 1,3,5-Trioxan, Paraformaldehyd und Dialkylformale mit 3 bis 7 C-Atomen in den Alkylgruppen in Betracht.In addition to formaldehyde as compound (b) there are 1,3,5-trioxane and paraformaldehyde and dialkyl formals with 3 to 7 carbon atoms in the alkyl groups into consideration.
Zur Herstellung der erfindungsgemäßen Verfahrensprodukte setzt man die Verbindungen (a) zunächst mit den Verbindungen (b) vorzugsweise in Gegenwart etwa äquimolarer Mengen Schwefelsäure (bezogen auf (a)) und dann mit den Verbindungen (c) um, und zwar gewünschtenfalls unter Schutzgasatmosphäre. In allen Fällen kannTo prepare the products of the process according to the invention, compounds (a) are preferably initially mixed with compounds (b) in the presence of approximately equimolar amounts of sulfuric acid (based on (a)) and then with the compounds (c), namely if desired under a protective gas atmosphere. In all cases it can
009810/1599
BAD009810/1599
BATH
-3- O.Z. 24 015-3- O.Z. 24 015
man hierbei von Mischungen verschiedener Verbindungen (a), (b) bzw. (c) ausgehen, wobei es im Falle der Komponente (c) besonders vorteilhaft ist, nacheinander etwa gleiche Mengen von Äthylen- und Propylenoxyd zu verwenden.mixtures of different compounds (a), (b) and (c) are used as a starting point, in the case of component (c) particularly it is advantageous to use approximately equal amounts of ethylene and propylene oxide one after the other.
Zweckmäßigerweise nimmt man die Umsetzung mit der Komponente (c) unter einem Druck von etwa 2 bis 20 atü mit Hilfe von Ätzalkalien wie Kaliumhydroxyd als Polymerisationsinitiatoren in Gegenwart eines inerten Lösungsmittels, z.B. eines aromatischen Kohlenwasserstoffs wie Benzol, Xylol oder Diisopropylbenzol vor. Diese Lösungsmittel werden nach der Reaktion größtenteils wieder abgedampft und gewünschtenfalls durch schwer flüchtige oleophile Lösungsmittel wie Mono- oder Dirnethylnaphthalin ersetzt.Appropriately, one takes the implementation with component (c) under a pressure of about 2 to 20 atmospheres with the help of caustic alkalis such as potassium hydroxide as a polymerization initiator in the presence of an inert solvent such as an aromatic hydrocarbon such as benzene, xylene or diisopropylbenzene. Most of these solvents are evaporated off again after the reaction and, if desired, replaced by low-volatility oleophilic solvents such as mono- or dimethylnaphthalene.
Die Verfahrensprodukte sind öllöslich und filmbildend. Sie haben durchschnittliche Molekulargewichte zwischen 600 und 2500 und eignen sich hervorragend als Lackbindemittel, Bindemittel für Papier-Btreichmassen und vor allem als Erdölemulsionsspalter für asphaltbasische .Öle.The products of the process are oil-soluble and film-forming. They have average molecular weights between 600 and 2500 and are suitable excellent as a lacquer binder, binder for paper coatings and above all as a petroleum emulsion breaker for asphalt-based oils.
Die Emulsionsspalter dienen dazu, das im Rohöl vorhandene Salzwasser und die Salzkriställchen zu entfernen. Hierin zeigen sie sich herkömmlichen Emulsionsspaltern für asphaltbasische Öle, z.B. solchen aus den veneztelischen Feldern, überlegen.The emulsion breakers are used to remove the salt water present in the crude oil and remove the salt crystals. In this they show consider conventional emulsion breakers for asphalt-based oils, e.g. those from the Venezuelan fields.
-A--A-
0 0 9 8 10/1599
BAD ORIGINAL0 0 9 8 10/1599
BATH ORIGINAL
-4- Q.JZ. 24-4- Q.JZ. 24
8lO g (5 mol) m-Diisopropylbenzol werden in einem Rührgefäß mit 75O g einer 4O#igen Pormaldehydlösung («»10 mol) versetzt. Unter Rühren werden diese? Lösung 800 g konzentrierte Schwefelsäure derart zugegeben, daß die Sumpftemperatur 70 0C nicht übersteigt. Nach vollständiger Zugabe der Schwefelsäure wird die Lösung noch 2 Stunden auf etwa 105 bis 110 0C erhitzt, wonach das so erhaltene Harz in 2 1 m-Diisopropylbenzol gelöst wird.810 g (5 mol) of m-diisopropylbenzene are mixed with 750 g of a 40 # strength formaldehyde solution («» 10 mol) in a stirred vessel. While stirring are these? Solution 800 g of concentrated sulfuric acid was added such that the bottom temperature does not exceed 70 0 C. After all of the sulfuric acid has been added, the solution is heated to about 105 to 110 ° C. for a further 2 hours, after which the resin thus obtained is dissolved in 2 lm-diisopropylbenzene.
In einem Autoklaven wird diese Lösung mit 50 g KOH-Pulver versetzt und auf 170 0C erhitzt, wonach man bei dieser Temperati«? portionsweise 12 kg Propylenoxyd und anschließend 11,2 kg Äthylenoxyd unter einem Druck von 5 bis 10 atü einpreßt.50 g of KOH powder are added to this solution in an autoclave and the mixture is heated to 170 ° C., after which it is carried out at this temperature. In portions 12 kg of propylene oxide and then 11.2 kg of ethylene oxide under a pressure of 5 to 10 atmospheres.
Nach dem Erkalten wird das braune, dickflüssige Produkt von Diisopropylbenzol befreit und mit einem Gemisch von und Dimethylnaphthalin auf etwa das doppelte VolunpnAfter cooling, the brown, viscous product is freed from diisopropylbenzene and mixed with a mixture of and dimethylnaphthalene to about double the volume
Die Wirkung als Erdölemulsionsspalter veranschaulicht f@ljgeiider VersuchsThe effect as a petroleum emulsion breaker is illustrated by f @ ljgeiider Attempt
Man versetzt 400 g eines Venezuela-Rohöles, das pro T«?jp§ 228 g Kochsalz enthielt, bei 80 0C mit 40 mg der Lösung des Ferfahrensproduktes (Wirkstoffgehalt etwa 20 mg) und mit 40 ml Wasser, rührt 50 min bei 97 °C, füllt das Gemisch in einen gereinigten graduierten Standzylinder und läßt die wäßrige Phase bei 80 0C sieh von der ölphase abtrennen. Nach t Minuten haben sich, wie die folgende Tabelle zeigt, jeweils insgesamt χ ml des Wassers vom öl abge-Is added to 400 g of a Venezuelan crude oil, the pro T '? Jp§ 228 g of common salt contained at 80 0 C with 40 of the solution of the Ferfahrensproduktes mg (active ingredient content is about 20 mg) and 40 ml of water, stirred for 50 min at 97 ° C, filling the mixture into a clean graduated measuring cylinder and allowing the aqueous phase at 80 0 C check to separate from the oil phase. After t minutes, as the following table shows, a total of χ ml of the water has separated from the oil.
. -5-009810/1599 . -5-009810 / 1599
BAD ORIGiNAtBATH ORIGINAL
-5- O.Z. 24 015-5- O.Z. 24 015
schieden. Die entsprechenden Werte y für den Blindversuch sind im Vergleich dazu in der nächsten Spalte aufgeführt:divorced. The corresponding values y for the blind test are in This is compared in the next column:
t [min] χt [min] χ
O 10 20 30 40 50 60O 10 20 30 40 50 60
0098107159900981071599
Claims (1)
BAD ORtGINAU 009810/1599
BAD ORtGINAU
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB0084862 | 1965-12-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1570320A1 true DE1570320A1 (en) | 1970-03-05 |
Family
ID=6982631
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19651570320 Pending DE1570320A1 (en) | 1965-12-07 | 1965-12-07 | Process for the production of oil-soluble condensation products |
Country Status (5)
Country | Link |
---|---|
AT (1) | AT267864B (en) |
BE (1) | BE690418A (en) |
DE (1) | DE1570320A1 (en) |
FR (1) | FR1503363A (en) |
GB (1) | GB1102218A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19916945C1 (en) * | 1999-04-15 | 2000-10-05 | Clariant Gmbh | Aromatic aldehyde resins and their use as emulsion breakers |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4082728A (en) * | 1976-08-23 | 1978-04-04 | The Standard Oil Company | Xylene-formaldehyde resin compositions and process |
-
1965
- 1965-12-07 DE DE19651570320 patent/DE1570320A1/en active Pending
-
1966
- 1966-11-29 BE BE690418D patent/BE690418A/xx unknown
- 1966-12-06 GB GB5451066A patent/GB1102218A/en not_active Expired
- 1966-12-07 AT AT1130266A patent/AT267864B/en active
- 1966-12-07 FR FR86453A patent/FR1503363A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19916945C1 (en) * | 1999-04-15 | 2000-10-05 | Clariant Gmbh | Aromatic aldehyde resins and their use as emulsion breakers |
Also Published As
Publication number | Publication date |
---|---|
GB1102218A (en) | 1968-02-07 |
AT267864B (en) | 1969-01-27 |
BE690418A (en) | 1967-05-29 |
FR1503363A (en) | 1967-11-24 |
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