GB691358A - Improvements in or relating to the production of unsaturated aliphatic phosphonamides - Google Patents
Improvements in or relating to the production of unsaturated aliphatic phosphonamidesInfo
- Publication number
- GB691358A GB691358A GB30293/49A GB3029349A GB691358A GB 691358 A GB691358 A GB 691358A GB 30293/49 A GB30293/49 A GB 30293/49A GB 3029349 A GB3029349 A GB 3029349A GB 691358 A GB691358 A GB 691358A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diallyl
- reacting
- radical
- phosphonamide
- unsaturated
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 11
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 9
- 229910021529 ammonia Inorganic materials 0.000 abstract 5
- -1 phosphonyl chloride Chemical class 0.000 abstract 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 5
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 150000001408 amides Chemical class 0.000 abstract 2
- OXLDKMFHLBAHLV-UHFFFAOYSA-N bis(prop-2-enyl) hydrogen phosphite Chemical compound C=CCOP(O)OCC=C OXLDKMFHLBAHLV-UHFFFAOYSA-N 0.000 abstract 2
- 238000007664 blowing Methods 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- 239000003607 modifier Substances 0.000 abstract 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 2
- 150000003141 primary amines Chemical class 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000005587 bubbling Effects 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000005260 corrosion Methods 0.000 abstract 1
- 230000007797 corrosion Effects 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 239000012530 fluid Substances 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 239000010687 lubricating oil Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 125000005541 phosphonamide group Chemical group 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 238000004078 waterproofing Methods 0.000 abstract 1
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 Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2412—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of unsaturated acyclic alcohols
-
- 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 Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
Abstract
Unsaturated aliphatic phosphonamides of the general formula <FORM:0691358/IV (b)/1> where Ru is an unsaturated C3-5 aliphatic radical; R1 is hydrogen, a C1-3 alkyl radical, a methylol radical or an unsaturated C3-5 aliphatic radical and R2 is hydrogen, an unsaturated C3-5 aliphatic radical or the radical <FORM:0691358/IV (b)/2> wherein m is a whole integer from 1 to 5 and R1 and Ru are as above defined, are prepared by condensing a di-substituted phosphonyl chloride of the general formula <FORM:0691358/IV (b)/3> where R is an unsaturated C3-5 radical with ammonia, an appropriate unsaturated primary or secondary amine having 3-5 carbon atoms in the unsaturated radical, a saturated C1-3 primary amine or an appropriate saturated C2-5 diamine and where the methylene or methylol compounds are desired, reacting the amides containing free amido hydrogen atoms with formaldehyde. In a modification, the phosphoryl chloride is formed in situ by reacting the corresponding phosphate (RO)2POH and at least one molecular proportion of carbon tetrachloride with the ammonia or amine. The compounds may be used as flame-proofing agents, water-proofing agents, coatings, plasticizers, lubricating oil modifiers, hydraulic fluid modifiers, corrosion inhibitors, insecticides and fungicides and as monomers or comonomers in polymerizations. In examples: (1) diallyl phosphonamide is prepared by reacting phosphorus oxychloride with allyl alcohol, dissolving the resulting diallyl phosphoryl chloride in toluene and bubbling ammonia therethrough, or (2) by reacting phosphorus trichloride with allyl alcohol (3 mols.) in toluene, blowing with air and then anhydrous ammonia to remove HCl, preparing a solution of the resulting phosphite in carbon tetrachloride with or without the addition of benzene or toluene and then introducing ammonia at -15 DEG to -20 DEG C. until alkaline; (4) N-methylol diallyl phosphonamide is prepared by reacting the product of (1) or (2) with aqueous formaldehyde at room temperature; (5) N : N1-methylene bis diallyl amido phosphate is produced by reacting diallyl phosphonamide with the product of (4) or by reacting formaldehyde with 2 mols. of diallyl phosphonamide; (6) N-allyl diallyl phosphonamide is prepared by reacting diallyl phosphite in carbon tetrachloride with excess of allyl amine; (7) N-diallyl phosphonamide is prepared from diallyl amine by the method of (6); (8) N : N1-ethylene bis-diallyl amido phosphate is prepared by reacting excess ethylene diamine with diallyl phosphite in carbon tetrachloride; (9) dipropargyl phosphonamide is prepared by reacting propargyl alcohol with phosphorus trichloride in carbon tetrachloride, removing HCl by air blowing and then passing in ammonia to form the desired amide. The Specification as open to inspection under Sect. 91 includes the production of phosphonamides of the above general formula wherein R1 may be a hydroxyalkyl radical of 1-3 carbon atoms and m is a small integer. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US691358XA | 1948-11-26 | 1948-11-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB691358A true GB691358A (en) | 1953-05-13 |
Family
ID=22086973
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB30293/49A Expired GB691358A (en) | 1948-11-26 | 1949-11-25 | Improvements in or relating to the production of unsaturated aliphatic phosphonamides |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB691358A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1006386B (en) * | 1954-11-05 | 1957-04-18 | J R Geigy A G , Basel (Schweiz) | Process for reducing the flammability of cellulosic material |
US2993776A (en) * | 1956-10-08 | 1961-07-25 | Monsanto Chemicals | Controlling vegetation |
US2993775A (en) * | 1956-10-08 | 1961-07-25 | Monsanto Chemicals | Method of controlling vegetation |
CN113980264A (en) * | 2021-11-30 | 2022-01-28 | 江苏钟山新材料有限公司 | Preparation method and application of flame-retardant polyether polyol |
-
1949
- 1949-11-25 GB GB30293/49A patent/GB691358A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1006386B (en) * | 1954-11-05 | 1957-04-18 | J R Geigy A G , Basel (Schweiz) | Process for reducing the flammability of cellulosic material |
US2993776A (en) * | 1956-10-08 | 1961-07-25 | Monsanto Chemicals | Controlling vegetation |
US2993775A (en) * | 1956-10-08 | 1961-07-25 | Monsanto Chemicals | Method of controlling vegetation |
CN113980264A (en) * | 2021-11-30 | 2022-01-28 | 江苏钟山新材料有限公司 | Preparation method and application of flame-retardant polyether polyol |
CN113980264B (en) * | 2021-11-30 | 2023-02-28 | 江苏钟山新材料有限公司 | Preparation method and application of flame-retardant polyether polyol |
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