GB744633A - N-alkyl-(or-aralkyl-) substituted alkylene polyamine methylene phosphonic acid compounds - Google Patents
N-alkyl-(or-aralkyl-) substituted alkylene polyamine methylene phosphonic acid compoundsInfo
- Publication number
- GB744633A GB744633A GB15525/53A GB1552553A GB744633A GB 744633 A GB744633 A GB 744633A GB 15525/53 A GB15525/53 A GB 15525/53A GB 1552553 A GB1552553 A GB 1552553A GB 744633 A GB744633 A GB 744633A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phosphonic acid
- methylene phosphonic
- alkyl
- acid
- aralkyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/3804—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se) not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3817—Acids containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se)
Abstract
The invention comprises as new products compounds having the formula: <FORM:0744633/IV(a)/1> wherein R is an alkyl or aralkyl group containing up to 18 carbon atoms; A is an alkyl or aralkyl group containing up to 18 carbon atoms, or -CH2.PO(OM)2; alkylene is -CH2CH2-, -CH(CH3)CH2- or -CH2.CH2 CH2-; n is 0, 1, 2, 3 or 4; and M is hydrogen, alkali metal, ammonium or alkyl-ammonium. The compounds may be obtained by dissolving a N-alkyl- (or -aralkyl-) substituted alkyleine polyamine in water containing sufficient caustic alkali to give a pH of from 10-11, heating the solution to a temperature of about 80-100 DEG C. and adding chloromethyl phosphonic acid disodium salt in an amount sufficient to substitute all the amino hydrogens present on the amine. The solution is then refluxed for about 10 hours or more. If the substituted alkylene polyamine is insoluble in water the reaction is carried out in absolute alcohol by dissolving the substituted alkylene polyamine in 5-10 times its volume of absolute ethanol and adding solid sodium hydroxide in a molar amount equivalent to the number of replaceable hydrogen atoms on the nitrogen atoms of the amine. An equal number of moles of chloromethyl phosphonic acid diethyl ester are then added while the solution is stirred and refluxed. The sodium chloride formed is filtered off, the ethanol removed by distillation and the substituted polyamine methylene phosphonic acid isolated by acid hydrolysis of the reaction product. The acids form metal chalate compounds with polyvalent metal ions such as those of Al, Ba, Ca, Pb. Typical examples of such metallic compounds are the barium compound of N,N1-dibenzyl ethylene diamine-N,N1-dimethylene phosphonic acid and the lead compound of N-octadecyl-ethylene diamine trimethylene phosphonic acid. Such metallic compounds may be prepared by dissolving the metal oxide, hydroxide, or carbonate in a solution of the organic alkyl- (or -aralkyl-) substituted alkylene polyamine methylene phosphonic acid. The residual charges on these metal derivatives may be neutralized by such salt forming groups as alkali metal and alkyl ammonium ions. N,N1-dibutyl ethylenediamine - N,N1 - dimethylenephosphonate ion is stated to be an effective deactivator of alkaline earth metal ions such as the magnesium ion. Examples are given for the production of: (1) N-butyl-ethylene diamine trimethylenephosphonic acid and its sodium salt; (2) dibenzyl ethylene diamine dimethylenephosphonic acid; (3) N-octadecyl diethylene triamine tri-(methylenephosphonic acid) and its sodium salt; (4) N,N1-dioctadecyl ethylene diamine di-(methylene phosphonic acid); (5) N,N1-dimethyl propylene diamine di-(methylene phosphonic acid); (6) the sodium salt of N,N1111-dibutyl tetraethylene pentamine penta-(methylene phosphonic acid), this salt is stated to be a sequestering agent with high capacity for combination with alkaline earth and heavy metal ions; (7) the sodium salt of N-monobutyl tetraethylene pentamine hexa-(methylene phosphonic acid) which is stated to have a greater affinity for alkaline earth metal ions than the compound (6); (8) N-monobenzyl trimethylene diamine tri-(methylene phosphonic acid); and (9) N,N1-dibutyl trimethylene diamine di-(methylene phosphonic acid). The products are stated to be valuable as detergents, metal carriers and as additives for lubricating oils. Specification 703,181 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US744633XA | 1952-06-06 | 1952-06-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB744633A true GB744633A (en) | 1956-02-08 |
Family
ID=22119688
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB15525/53A Expired GB744633A (en) | 1952-06-06 | 1953-06-05 | N-alkyl-(or-aralkyl-) substituted alkylene polyamine methylene phosphonic acid compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB744633A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1045373B (en) * | 1957-04-26 | 1958-12-04 | Hoechst Ag | Use of phosphonic acids |
EP0015818A1 (en) * | 1979-03-05 | 1980-09-17 | Oxysynthese | Stabilised aqueous solutions of hydrogen peroxide |
WO2001079215A1 (en) * | 2000-04-18 | 2001-10-25 | Dow Global Technologies Inc. | N?α, Nφ¿-DIALKYL AMINOMETHYLENEPHOSPHONIC ACIDS AND USE THEREOF |
-
1953
- 1953-06-05 GB GB15525/53A patent/GB744633A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1045373B (en) * | 1957-04-26 | 1958-12-04 | Hoechst Ag | Use of phosphonic acids |
EP0015818A1 (en) * | 1979-03-05 | 1980-09-17 | Oxysynthese | Stabilised aqueous solutions of hydrogen peroxide |
FR2450783A1 (en) * | 1979-03-05 | 1980-10-03 | Oxysynthese | STABILIZED AQUEOUS SOLUTIONS OF HYDROGEN PEROXIDE |
WO2001079215A1 (en) * | 2000-04-18 | 2001-10-25 | Dow Global Technologies Inc. | N?α, Nφ¿-DIALKYL AMINOMETHYLENEPHOSPHONIC ACIDS AND USE THEREOF |
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