DE1922043C3 - Process for the preparation of guanidine salts of carboxylic acids - Google Patents
Process for the preparation of guanidine salts of carboxylic acidsInfo
- Publication number
- DE1922043C3 DE1922043C3 DE1922043A DE1922043A DE1922043C3 DE 1922043 C3 DE1922043 C3 DE 1922043C3 DE 1922043 A DE1922043 A DE 1922043A DE 1922043 A DE1922043 A DE 1922043A DE 1922043 C3 DE1922043 C3 DE 1922043C3
- Authority
- DE
- Germany
- Prior art keywords
- guanidine
- carboxylic acids
- preparation
- reaction
- guanidine salts
- 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
Links
- 238000000034 method Methods 0.000 title claims description 10
- 150000002357 guanidines Chemical class 0.000 title claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 claims description 11
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 7
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 14
- 229910002092 carbon dioxide Inorganic materials 0.000 description 8
- 239000001569 carbon dioxide Substances 0.000 description 8
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 7
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 7
- 239000000344 soap Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- TVPCUVQDVRZTAL-UHFFFAOYSA-N 2-ethylhexanoyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC(=O)C(CC)CCCC TVPCUVQDVRZTAL-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- DNOSZYUZVCJLMM-UHFFFAOYSA-N carbamimidoylazanium;benzoate Chemical compound NC(N)=[NH2+].[O-]C(=O)C1=CC=CC=C1 DNOSZYUZVCJLMM-UHFFFAOYSA-N 0.000 description 1
- NDRMWPVNHDJUCA-UHFFFAOYSA-N carbamimidoylazanium;octadecanoate Chemical compound NC(N)=N.CCCCCCCCCCCCCCCCCC(O)=O NDRMWPVNHDJUCA-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NWADXBLMWHFGGU-UHFFFAOYSA-N dodecanoic anhydride Chemical compound CCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCC NWADXBLMWHFGGU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- DXTIKTAIYCJTII-UHFFFAOYSA-N guanidine acetate Chemical compound CC([O-])=O.NC([NH3+])=N DXTIKTAIYCJTII-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- WVJVHUWVQNLPCR-UHFFFAOYSA-N octadecanoyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCC WVJVHUWVQNLPCR-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Guanidinsalzen von Carbonsäuren durch Umsetzung von Guanidincarbonat mit den jeweiligen Säureanhydriden der entsprechenden Carbonsäuren. The invention relates to a process for the preparation of guanidine salts of carboxylic acids by reacting guanidine carbonate with the respective acid anhydrides of the corresponding carboxylic acids.
Bekanntlich sind Guanidinsalze beständiger als freies Guanidin. Da darüber hinaus bei technischen Verfahren zur Herstellung von Guanidin meistens Guanidinsalze anfallen, basieren bisherige Verfahren zur Herstellung von Guanidinseifen im wesentlichen auf der Umsetzung von Guanidinsalzen, vielfach Guanidincarbonat, mit den jeweiligen Fettsäuren. Bei der Umsetzung von Guanidincarbonat mit freien Fettsäuren wird neben CCh auch Wasser abgespalten. Die anschließende Trocknung solcher auf diesem Wege hergestellten Guanidinseifen muß mit großer Sorgfalt und erheblichem wirtschaftlichem Aufwand durchgeführt werden und stellt ein erhebliches Problem dar.It is known that guanidine salts are more stable than free guanidine. Since, in addition, with technical Processes for the production of guanidine mostly result from guanidine salts, based on previous processes for the production of guanidine soaps essentially on the implementation of guanidine salts, in many cases Guanidine carbonate, with the respective fatty acids. When implementing guanidine carbonate with free In addition to CCh, water is also split off fatty acids. The subsequent drying of such on this The guanidine soaps produced must be made with great care and considerable economic effort carried out and poses a significant problem.
Es wurde gefunden, daß man Guanidinsalze von Carbonsäuren in einfacher Weise leicht dadurch herstellen kann, daß man Guanidincarbonat mit Carbonsäureanhydriden in einem Temperaturbereich zwischen 50 und 200' C, jedoch oberhalb des Schmelzpunktes der jeweils eingesetzten Carbonsäureanhydride umsetzt.It has been found that guanidine salts of carboxylic acids can be easily prepared thereby in a simple manner can that you guanidine carbonate with carboxylic anhydrides in a temperature range between 50 and 200 ° C., but above the melting point of the carboxylic acid anhydrides used in each case implements.
Bei den Umsetzungen von Guanidincarbonat mit Carbonsäureanhydriden wird Kohlendioxid quantitativ freigesetzt. Da hierbei im Gegensatz zur Umsetzung mit Fettsäuren kein Reaktionswasser gebildet wird, kann man durch das erfindungsgemäße Verfahren von vornherein wasserfreie Guanidinseifen herstellen. Ein weiterer Vorteil dieses Verfahrens ist darin zu sehen, daß die Umsetzung von Guanidincarbonat mit Carbonsäureanhydriden in Abwesenheit von Lösungsmitteln durchgeführt werden kann, so daß, bezogen auf das eingesetzte Reaktionsvolumen, jeweils ein hoher Substanzaustrag an Guanidinseifen sichergestellt wird. Das bei der Umsetzung freigesetzte Kohlendioxid kann weiterer wirtschaftlicher Verwendung zugeführt werden.In the reactions of guanidine carbonate with carboxylic acid anhydrides, carbon dioxide becomes quantitative released. Since, in contrast to the reaction with fatty acids, no water of reaction is formed here one can use the process according to the invention from the outset to produce anhydrous guanidine soaps produce. Another advantage of this process is that the implementation of Guanidine carbonate can be carried out with carboxylic acid anhydrides in the absence of solvents can, so that, based on the reaction volume used, in each case a high substance discharge is ensured of guanidine soaps. The carbon dioxide released during the reaction can further be supplied to economic use.
Je nach eingesetztem Carbonsäureanhydrid tritt der Reaktionsbeginn bereits bei 60 bis 70° C ein. Die eigentliche Reaktion ist an dem starken Entweichen von Kohlendioxid deutlich zu erkennen. Nach beendeter CCh-Entwicklung ist die Reaktion praktisch beendet. In vielen Fällen wird durch ein nachträgliches Erhitzen eine klare Schmelze erhalten. Da die Umsetzungen in relativ kurzer Zeit und im stöchiometrischen Verhältnis durchgeführt werden, sst durch das erfindungsgemäße Verfahren eine sehr wirtschaftliche Herstellung von Guanidinseifen gegeben.Depending on the carboxylic acid anhydride used, the start of the reaction occurs as early as 60 to 70.degree. the The actual reaction can be clearly recognized by the strong escape of carbon dioxide. After finished The reaction is practically finished with CCh evolution. In many cases, a subsequent Heating obtained a clear melt. Since the reactions take place in a relatively short time and in the stoichiometric Ratio are carried out, sst a very economical by the process according to the invention Manufacture of guanidine soaps given.
Die Verfahrensprodukte eignen sich hervorragend als Gleit-, Trennmittel, Emulgatoren, als Zusätze zu Seifen und für viele andere Zwecke, für die häufig ίο auch Metallseifen eingesetzt werden.The process products are ideal as lubricants, release agents, emulsifiers, as additives Soaps and for many other purposes for which metallic soaps are often used.
Das Verfahren wird durch nachstehende "^.spiele näher erläutert:The procedure is followed by "^. Games explained in more detail:
54 g 2-Äthylhexansäureanhydrid und 36 g Guanidincarbonat werden in einem 500 ml Glasdreihalskolben unter Rühren auf etwa 100 bis ülO°C erhitzt. Nach Erreichen dieser Temperatur tritt die eigentliche Reaktion unter starkem Entweichen von Kohlendioxid ein. Nach dem Abklingen der CCh-Entwicklung wird die Reaktionsmischung nach etwa 35 Minuten auf etwa 145 bis 150° C erhitzt. Nach Erhalten einer klaren Schmelze wird das Reaktionsprodukt abgekühlt. Die Ausbeute an Guanidinoctoat beträgt 80,0 g.54 g of 2-ethylhexanoic anhydride and 36 g of guanidine carbonate are heated in a 500 ml glass three-necked flask with stirring to about 100 to 100 ° C. After this temperature has been reached, the actual reaction occurs with a strong escape of Carbon dioxide. After the CCh development has subsided, the reaction mixture becomes after about Heated to about 145 to 150 ° C for 35 minutes. After a clear melt has been obtained, the reaction product is cooled. The yield of guanidine octoate is 80.0 g.
18 g Guanidincarbonat und 38,2 g Laurinsäureanhydnd werden in einem 500 ml-Dreihaiskolben auf etwa 70° C erhitzt. Bei einet Temperatur von etwa 60° C tritt die eigentliche Reaktion unter starker CCh-Entwicklung ein. Nach dem Abklingen der CCh-Entwicklung wird das Reaktionsgemisch etwa 35 Minuten auf etwa 150° C erhitzt. Nach beendeter Reaktion wird eine klare Schmelze erhalten. Nach dem Abkühlen werden 51,5g Guanidinlautat erhalten. 18 g of guanidine carbonate and 38.2 g of lauric anhydride are placed in a 500 ml three-necked flask heated to about 70 ° C. At a temperature of around 60 ° C, the actual reaction occurs more strongly CCh development a. After the evolution of CCh has subsided, the reaction mixture becomes about Heated to about 150 ° C for 35 minutes. After the reaction has ended, a clear melt is obtained. To on cooling, 51.5 g of guanidine acetate are obtained.
18g Guanidincarbonat und 55,2 g Stearinsäureanhydrid werden in einem 500 ml-Dreihaiskolben unter Rühren auf etwa 70° C erhitzt. Nach Erreichen dieser Temperatur tritt unter starker Kohlendioxidentwicklung die eigentliche Reaktion ein. Nach Abklingen der Kohlendioxidentwicklung wird das Reaktionsgemisch etwa 45 Minuten auf 140 bis 150° C erhitzt. Nach beendeter Reaktion wird eine klare Schmelze erhalten. Nach dem Abkühlen werden 68,6 g Guanidinstearat erhalten.18 g guanidine carbonate and 55.2 g stearic anhydride are heated in a 500 ml three-necked flask with stirring to about 70 ° C. After reaching At this temperature, the actual reaction occurs with strong evolution of carbon dioxide. After subsiding the evolution of carbon dioxide, the reaction mixture is heated to 140 to 150 ° C. for about 45 minutes heated. After the reaction has ended, a clear melt is obtained. After cooling down 68.6 g of guanidine stearate were obtained.
5°5 °
18 g Guanidincarbonat und 22,6 g Benzoesäureanhydrid werden in einem 500 ml-Dreihalskolben unter Rühren auf etwa 1000C erhitzt. Nach Erreichen der Temperatur tritt unter Kohlendioxidentwicklung die eigentliche Reaktions ein. Nach Abklingen der Kohlendioxidentwicklung wird die Reaktionsmischung etwa 2 Stunden auf etwa 150 bis 160° C erhitzt. Nach dem Abkühlen werden 36,2 g Guanidinbenzoat erhalten.18 g of guanidine carbonate and 22.6 g of benzoic anhydride are heated to about 100 ° C. in a 500 ml three-necked flask with stirring. After the temperature has been reached, the actual reaction occurs with evolution of carbon dioxide. After the evolution of carbon dioxide has subsided, the reaction mixture is heated to about 150 to 160 ° C. for about 2 hours. After cooling, 36.2 g of guanidine benzoate are obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6808295A NL6808295A (en) | 1968-06-13 | 1968-06-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1922043A1 DE1922043A1 (en) | 1970-01-29 |
| DE1922043B2 DE1922043B2 (en) | 1974-08-22 |
| DE1922043C3 true DE1922043C3 (en) | 1975-05-07 |
Family
ID=19803883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1922043A Expired DE1922043C3 (en) | 1968-06-13 | 1969-04-30 | Process for the preparation of guanidine salts of carboxylic acids |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1922043C3 (en) |
| FR (1) | FR2010801A1 (en) |
| NL (1) | NL6808295A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024175245A1 (en) * | 2023-02-23 | 2024-08-29 | Thor Gmbh | Synergistic compositions containing guanidine |
-
1968
- 1968-06-13 NL NL6808295A patent/NL6808295A/xx unknown
-
1969
- 1969-04-30 DE DE1922043A patent/DE1922043C3/en not_active Expired
- 1969-05-23 FR FR6916939A patent/FR2010801A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2010801A1 (en) | 1970-02-20 |
| DE1922043A1 (en) | 1970-01-29 |
| DE1922043B2 (en) | 1974-08-22 |
| NL6808295A (en) | 1969-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |