IL38340A - Process for the manufacture of 2-chloroethane-phosphonic acid - Google Patents
Process for the manufacture of 2-chloroethane-phosphonic acidInfo
- Publication number
- IL38340A IL38340A IL38340A IL3834071A IL38340A IL 38340 A IL38340 A IL 38340A IL 38340 A IL38340 A IL 38340A IL 3834071 A IL3834071 A IL 3834071A IL 38340 A IL38340 A IL 38340A
- Authority
- IL
- Israel
- Prior art keywords
- chloroethane
- hydrogen chloride
- phosphonic acid
- acid
- pressure
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 title description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 81
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 37
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 6
- 238000003776 cleavage reaction Methods 0.000 claims description 6
- 230000007017 scission Effects 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 14
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 12
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 10
- XXIDKSWYSYEFAG-UHFFFAOYSA-N 1-chloro-2-[2-chloroethoxy(2-chloroethyl)phosphoryl]oxyethane Chemical compound ClCCOP(=O)(CCCl)OCCCl XXIDKSWYSYEFAG-UHFFFAOYSA-N 0.000 description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- LUVCTYHBTXSAMX-UHFFFAOYSA-N tris(2-chloroethyl) phosphite Chemical compound ClCCOP(OCCCl)OCCCl LUVCTYHBTXSAMX-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- QBSWHWLQSRONOM-UHFFFAOYSA-N 1-[bis(2-chloroethoxy)phosphoryl]-1-chloroethane Chemical compound ClCCOP(=O)(C(Cl)C)OCCCl QBSWHWLQSRONOM-UHFFFAOYSA-N 0.000 description 1
- SEHJHHHUIGULEI-UHFFFAOYSA-N 2-hydroxyethylphosphonic acid Chemical compound OCCP(O)(O)=O SEHJHHHUIGULEI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KKQCMAJELBNKNV-UHFFFAOYSA-N ClCCOP(O)=O.ClCC Chemical compound ClCCOP(O)=O.ClCC KKQCMAJELBNKNV-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000010517 secondary reaction 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702061610 DE2061610C (de) | 1970-12-15 | Verfahren zur Herstellung von 2 Chlorathanphosphonsaure | |
| DE19712134346 DE2134346C (de) | 1971-07-09 | Verfahren zur Herstellung von 2 Chlor athanphosphonsaure | |
| DE19712148549 DE2148549C3 (de) | 1971-09-29 | 1971-09-29 | Verfahren zur Herstellung von 2-Chlorathanphosphonsaure |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL38340A0 IL38340A0 (en) | 1972-02-29 |
| IL38340A true IL38340A (en) | 1974-10-22 |
Family
ID=27183043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL38340A IL38340A (en) | 1970-12-15 | 1971-12-13 | Process for the manufacture of 2-chloroethane-phosphonic acid |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS594440B1 (fr) |
| BE (1) | BE776735A (fr) |
| CA (1) | CA942316A (fr) |
| CH (1) | CH569031A5 (fr) |
| CS (1) | CS167336B2 (fr) |
| FR (1) | FR2118579A5 (fr) |
| GB (1) | GB1373513A (fr) |
| IL (1) | IL38340A (fr) |
| IT (1) | IT943888B (fr) |
| NL (1) | NL7116981A (fr) |
| RO (1) | RO60363A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1085870A (fr) * | 1976-12-20 | 1980-09-16 | Robert J. Kiesel | Preparation d'acide haloalkylphosphonique |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL41275A (en) * | 1967-04-27 | 1973-10-25 | Gen Aniline & Film Corp | Process for producing beta-haloethyl-phosphonic acids |
-
1971
- 1971-12-08 CS CS8549A patent/CS167336B2/cs unknown
- 1971-12-10 NL NL7116981A patent/NL7116981A/xx unknown
- 1971-12-10 GB GB5746971A patent/GB1373513A/en not_active Expired
- 1971-12-10 CH CH1812071A patent/CH569031A5/xx not_active IP Right Cessation
- 1971-12-13 IT IT32311/71A patent/IT943888B/it active
- 1971-12-13 IL IL38340A patent/IL38340A/en unknown
- 1971-12-14 CA CA130,083A patent/CA942316A/en not_active Expired
- 1971-12-14 FR FR7144825A patent/FR2118579A5/fr not_active Expired
- 1971-12-14 RO RO69049A patent/RO60363A/ro unknown
- 1971-12-14 JP JP46100789A patent/JPS594440B1/ja active Pending
- 1971-12-15 BE BE776735A patent/BE776735A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT943888B (it) | 1973-04-10 |
| GB1373513A (en) | 1974-11-13 |
| FR2118579A5 (fr) | 1972-07-28 |
| CA942316A (en) | 1974-02-19 |
| NL7116981A (fr) | 1972-06-19 |
| JPS594440B1 (fr) | 1984-01-30 |
| CS167336B2 (fr) | 1976-04-29 |
| IL38340A0 (en) | 1972-02-29 |
| CH569031A5 (fr) | 1975-11-14 |
| RO60363A (fr) | 1976-06-15 |
| BE776735A (fr) | 1972-06-15 |
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