IL31362A - אלמימות של חומצות זרחניות ביס- הלואלקיליות - Google Patents
אלמימות של חומצות זרחניות ביס- הלואלקיליותInfo
- Publication number
- IL31362A IL31362A IL31362A IL3136269A IL31362A IL 31362 A IL31362 A IL 31362A IL 31362 A IL31362 A IL 31362A IL 3136269 A IL3136269 A IL 3136269A IL 31362 A IL31362 A IL 31362A
- Authority
- IL
- Israel
- Prior art keywords
- bis
- acid
- phosphonic acid
- anhydride
- beta
- Prior art date
Links
- -1 haloalkyl phosphonic acid Chemical compound 0.000 title description 6
- 239000002253 acid Substances 0.000 claims description 20
- 150000008064 anhydrides Chemical class 0.000 claims description 17
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 25
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- CNGZUJQPNVPPCJ-UHFFFAOYSA-N 1-chloroethylphosphonic acid Chemical compound CC(Cl)P(O)(O)=O CNGZUJQPNVPPCJ-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- ZFFPZOJIBMKDGH-UHFFFAOYSA-N 2-chloropropylphosphonic acid Chemical compound CC(Cl)CP(O)(O)=O ZFFPZOJIBMKDGH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- IFVRMHVMSSPQLZ-UHFFFAOYSA-N P(O)(O)=O.ClCC Chemical compound P(O)(O)=O.ClCC IFVRMHVMSSPQLZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 150000003009 phosphonic acids Chemical class 0.000 description 2
- 229940005657 pyrophosphoric acid Drugs 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- 238000000954 titration curve Methods 0.000 description 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- AATNZNJRDOVKDD-UHFFFAOYSA-N 1-[ethoxy(ethyl)phosphoryl]oxyethane Chemical compound CCOP(=O)(CC)OCC AATNZNJRDOVKDD-UHFFFAOYSA-N 0.000 description 1
- AQKIXTCXLQZFMW-UHFFFAOYSA-N 1-[hexoxy(hexyl)phosphoryl]oxyhexane Chemical compound CCCCCCOP(=O)(CCCCCC)OCCCCCC AQKIXTCXLQZFMW-UHFFFAOYSA-N 0.000 description 1
- UPFSQTGEVLHCIQ-UHFFFAOYSA-N 2-[propan-2-yl(propan-2-yloxy)phosphoryl]oxypropane Chemical compound CC(C)OP(=O)(C(C)C)OC(C)C UPFSQTGEVLHCIQ-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- BXJCEULFBLJODE-UHFFFAOYSA-N 2-chloroethyl dihydrogen phosphite Chemical compound OP(O)OCCCl BXJCEULFBLJODE-UHFFFAOYSA-N 0.000 description 1
- ZWZVADPGMCQWNU-UHFFFAOYSA-N CC(COP(O)=O)Cl Chemical compound CC(COP(O)=O)Cl ZWZVADPGMCQWNU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005600 alkyl phosphonate group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 231100000508 hormonal effect Toxicity 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-O oxonium Chemical compound [OH3+] XLYOFNOQVPJJNP-UHFFFAOYSA-O 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- LUVCTYHBTXSAMX-UHFFFAOYSA-N tris(2-chloroethyl) phosphite Chemical compound ClCCOP(OCCCl)OCCCl LUVCTYHBTXSAMX-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3895—Pyrophosphonic acids; phosphonic acid anhydrides
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70074368A | 1968-01-26 | 1968-01-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31362A0 IL31362A0 (en) | 1969-03-27 |
| IL31362A true IL31362A (he) | 1972-10-29 |
Family
ID=24814694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31362A IL31362A (he) | 1968-01-26 | 1969-01-03 | אלמימות של חומצות זרחניות ביס- הלואלקיליות |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3600435A (he) |
| JP (1) | JPS543934B1 (he) |
| CH (1) | CH509763A (he) |
| DE (1) | DE1815999C3 (he) |
| FR (1) | FR2000815A1 (he) |
| GB (1) | GB1224591A (he) |
| IL (1) | IL31362A (he) |
| MY (1) | MY7200087A (he) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1950100B2 (de) * | 1969-10-04 | 1976-12-02 | Bayer Ag, 5090 Leverkusen | Verwendung von 2-chloraethan-(thiono)- phosphonsaeureamido-verbindungen zur beeinflussung des pflanzenwachstums |
| US4401454A (en) * | 1969-10-24 | 1983-08-30 | Union Carbide Corporation | Growth regulation methods |
| US3879188A (en) * | 1969-10-24 | 1975-04-22 | Amchem Prod | Growth regulation process |
| US3876412A (en) * | 1970-08-13 | 1975-04-08 | Purdue Research Foundation | Pyrophosphate treatment of sweet corn |
| US4240819A (en) * | 1972-01-28 | 1980-12-23 | Union Carbide Agricultural Products, Inc. | Method for the inhibition of plant growth |
| US4129588A (en) * | 1973-09-07 | 1978-12-12 | The United States Of America As Represented By The Secretary Of Agriculture | Selective manufacture of anhydrous modifications of methyl phosphonic acid and use thereof in making pure methyl phosphonic acid and salts thereof |
| US4106923A (en) * | 1975-11-10 | 1978-08-15 | Monsanto Company | Phosphonomethyl glycine ester anhydrides, herbicidal composition containing same and use thereof |
| DE2758580A1 (de) * | 1977-12-29 | 1979-07-05 | Hoechst Ag | Verfahren zur herstellung von phosphin- und phosphonsaeure-anhydriden |
| DE10361832A1 (de) * | 2003-12-30 | 2005-07-28 | Celanese Ventures Gmbh | Protonenleitende Membran und deren Verwendung |
| DE10361932A1 (de) * | 2003-12-30 | 2005-07-28 | Celanese Ventures Gmbh | Protonenleitende Membran und deren Verwendung |
| US7435841B2 (en) | 2004-03-10 | 2008-10-14 | Rhodia Inc. | Preparation of halohydrocarbyl phosphonic acid diesters |
-
1968
- 1968-01-26 US US700743A patent/US3600435A/en not_active Expired - Lifetime
- 1968-12-20 DE DE1815999A patent/DE1815999C3/de not_active Expired
- 1968-12-23 CH CH1915968A patent/CH509763A/de not_active IP Right Cessation
-
1969
- 1969-01-03 IL IL31362A patent/IL31362A/he unknown
- 1969-01-23 GB GB3789/69A patent/GB1224591A/en not_active Expired
- 1969-01-24 FR FR6901394A patent/FR2000815A1/fr not_active Withdrawn
- 1969-01-25 JP JP563569A patent/JPS543934B1/ja active Pending
-
1972
- 1972-12-30 MY MY87/72A patent/MY7200087A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL31362A0 (en) | 1969-03-27 |
| GB1224591A (en) | 1971-03-10 |
| JPS543934B1 (he) | 1979-02-28 |
| DE1815999C3 (de) | 1978-06-08 |
| DE1815999A1 (de) | 1969-08-21 |
| MY7200087A (en) | 1972-12-31 |
| FR2000815A1 (he) | 1969-09-12 |
| DE1815999B2 (de) | 1977-10-06 |
| CH509763A (de) | 1971-07-15 |
| US3600435A (en) | 1971-08-17 |
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