DE2755278A1 - Verfahren zur herstellung von halogenphosphorsaeure - Google Patents
Verfahren zur herstellung von halogenphosphorsaeureInfo
- Publication number
- DE2755278A1 DE2755278A1 DE19772755278 DE2755278A DE2755278A1 DE 2755278 A1 DE2755278 A1 DE 2755278A1 DE 19772755278 DE19772755278 DE 19772755278 DE 2755278 A DE2755278 A DE 2755278A DE 2755278 A1 DE2755278 A1 DE 2755278A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- water
- cepa
- hcl
- acid
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 36
- 239000002253 acid Substances 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 239000011541 reaction mixture Substances 0.000 claims description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 9
- 239000012071 phase Substances 0.000 claims description 7
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 6
- 239000012433 hydrogen halide Substances 0.000 claims description 6
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 claims description 5
- -1 Haloalkyl phosphonate Chemical compound 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000005690 diesters Chemical class 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 50
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 50
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- NGADBMHGWDBFSS-UHFFFAOYSA-N 2-iodoethylphosphonic acid Chemical compound OP(O)(=O)CCI NGADBMHGWDBFSS-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- LUVCTYHBTXSAMX-UHFFFAOYSA-N tris(2-chloroethyl) phosphite Chemical compound ClCCOP(OCCCl)OCCCl LUVCTYHBTXSAMX-UHFFFAOYSA-N 0.000 description 2
- XXIDKSWYSYEFAG-UHFFFAOYSA-N 1-chloro-2-[2-chloroethoxy(2-chloroethyl)phosphoryl]oxyethane Chemical compound ClCCOP(=O)(CCCl)OCCCl XXIDKSWYSYEFAG-UHFFFAOYSA-N 0.000 description 1
- LHHMNJZNWUJFOC-UHFFFAOYSA-N 1-chloro-2-[2-chloroethoxy(ethenyl)phosphoryl]oxyethane Chemical compound ClCCOP(=O)(C=C)OCCCl LHHMNJZNWUJFOC-UHFFFAOYSA-N 0.000 description 1
- MCCNUUMBDXCUJZ-UHFFFAOYSA-N 1-fluoro-2-[2-fluoroethoxy(2-fluoroethyl)phosphoryl]oxyethane Chemical compound FCCOP(OCCF)(=O)CCF MCCNUUMBDXCUJZ-UHFFFAOYSA-N 0.000 description 1
- NLAFDAIUYHCRGU-UHFFFAOYSA-N 2-chloroethoxy(2-chloroethyl)phosphinic acid Chemical compound ClCCP(=O)(O)OCCCl NLAFDAIUYHCRGU-UHFFFAOYSA-N 0.000 description 1
- BLZGAOUANQHLFT-UHFFFAOYSA-N 2-fluoroethoxy(2-fluoroethyl)phosphinic acid Chemical compound C(CF)OP(=O)(CCF)O BLZGAOUANQHLFT-UHFFFAOYSA-N 0.000 description 1
- ZHNLTTJSGOZSMN-UHFFFAOYSA-N 2-fluoroethylphosphonic acid Chemical compound OP(O)(=O)CCF ZHNLTTJSGOZSMN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000218642 Abies Species 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- UQLLWWBDSUHNEB-CZUORRHYSA-N Cefaprin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CSC1=CC=NC=C1 UQLLWWBDSUHNEB-CZUORRHYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001358279 Malaya Species 0.000 description 1
- 244000070406 Malus silvestris Species 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 239000004063 acid-resistant material Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 235000021015 bananas Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229940081090 cefa Drugs 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 238000005303 weighing 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)]
- C07F9/3804—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
-
- 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)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
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 |
|---|---|---|---|
| US75279676A | 1976-12-20 | 1976-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2755278A1 true DE2755278A1 (de) | 1978-06-29 |
Family
ID=25027881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772755278 Withdrawn DE2755278A1 (de) | 1976-12-20 | 1977-12-12 | Verfahren zur herstellung von halogenphosphorsaeure |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5377017A (fr) |
| BE (1) | BE860496A (fr) |
| BR (1) | BR7707294A (fr) |
| CA (1) | CA1085870A (fr) |
| DE (1) | DE2755278A1 (fr) |
| FR (1) | FR2374329A1 (fr) |
| GB (1) | GB1592265A (fr) |
| IL (1) | IL53081A (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986000903A1 (fr) * | 1984-07-18 | 1986-02-13 | Nitrokémia Ipartelepek | Esters de l'acide 2-chloro-ethyl-phosphonique et agents de regulation de la croissance des plantes contenant ces esters en tant qu'ingredients actifs |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1074420C (zh) * | 1999-10-08 | 2001-11-07 | 常熟市农药厂 | 70%－80%液体2－氯乙基膦酸的制备方法 |
| JP4514779B2 (ja) | 2007-09-28 | 2010-07-28 | 株式会社クレブ | 防寒手袋 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3787486A (en) * | 1969-10-17 | 1974-01-22 | Gaf Corp | Preparation of haloethane phosphonic acids |
| CS167336B2 (fr) * | 1970-12-15 | 1976-04-29 | Hoechst Ag | |
| US3808265A (en) * | 1971-03-26 | 1974-04-30 | Gaf Corp | Preparation of 2-haloethylphosphonic acid |
| DE2156284C3 (de) * | 1971-11-12 | 1980-08-07 | Hoechst Ag, 6000 Frankfurt | Herstellung von 2-Chloräthanphosphonsäure |
-
1977
- 1977-09-27 CA CA287,599A patent/CA1085870A/fr not_active Expired
- 1977-10-09 IL IL53081A patent/IL53081A/xx unknown
- 1977-10-31 BR BR7707294A patent/BR7707294A/pt unknown
- 1977-11-04 BE BE182356A patent/BE860496A/fr unknown
- 1977-11-08 FR FR7733655A patent/FR2374329A1/fr not_active Withdrawn
- 1977-11-11 GB GB47119/77A patent/GB1592265A/en not_active Expired
- 1977-12-12 DE DE19772755278 patent/DE2755278A1/de not_active Withdrawn
- 1977-12-20 JP JP15250077A patent/JPS5377017A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986000903A1 (fr) * | 1984-07-18 | 1986-02-13 | Nitrokémia Ipartelepek | Esters de l'acide 2-chloro-ethyl-phosphonique et agents de regulation de la croissance des plantes contenant ces esters en tant qu'ingredients actifs |
Also Published As
| Publication number | Publication date |
|---|---|
| IL53081A (en) | 1981-05-20 |
| BE860496A (fr) | 1978-05-05 |
| FR2374329A1 (fr) | 1978-07-13 |
| BR7707294A (pt) | 1978-08-01 |
| GB1592265A (en) | 1981-07-01 |
| JPS5377017A (en) | 1978-07-08 |
| IL53081A0 (en) | 1977-12-30 |
| CA1085870A (fr) | 1980-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |