DE1618383B1 - Verfahren zur Herstellung von 2-Chloräthanphosphonsäureestern - Google Patents
Verfahren zur Herstellung von 2-ChloräthanphosphonsäureesternInfo
- Publication number
- DE1618383B1 DE1618383B1 DE19671618383 DE1618383A DE1618383B1 DE 1618383 B1 DE1618383 B1 DE 1618383B1 DE 19671618383 DE19671618383 DE 19671618383 DE 1618383 A DE1618383 A DE 1618383A DE 1618383 B1 DE1618383 B1 DE 1618383B1
- Authority
- DE
- Germany
- Prior art keywords
- phosphite
- phosphonic acid
- acid esters
- vinyl chloride
- calculated
- 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- Withdrawn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 description 7
- IFVRMHVMSSPQLZ-UHFFFAOYSA-N P(O)(O)=O.ClCC Chemical class P(O)(O)=O.ClCC IFVRMHVMSSPQLZ-UHFFFAOYSA-N 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 6
- -1 halogen olefins Chemical class 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- HDIBKVVPMJKRGL-UHFFFAOYSA-N bis(2-ethylhexyl) hydrogen phosphite Chemical compound CCCCC(CC)COP(O)OCC(CC)CCCC HDIBKVVPMJKRGL-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- ZHRXESWHJGMKCX-UHFFFAOYSA-N bis(2-ethylbutyl) hydrogen phosphite Chemical compound CCC(CC)COP(O)OCC(CC)CC ZHRXESWHJGMKCX-UHFFFAOYSA-N 0.000 description 3
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 3
- XFUSKHPBJXJFRA-UHFFFAOYSA-N dihexyl hydrogen phosphite Chemical compound CCCCCCOP(O)OCCCCCC XFUSKHPBJXJFRA-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- RJODUASCKGDMQK-UHFFFAOYSA-N diethoxy(sulfanylidene)phosphanium Chemical compound CCO[P+](=S)OCC RJODUASCKGDMQK-UHFFFAOYSA-N 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- LLWDULGXUFLRGH-UHFFFAOYSA-N propan-2-yloxy(propan-2-ylsulfanyl)phosphinous acid Chemical compound CC(C)OP(O)SC(C)C LLWDULGXUFLRGH-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- SUECSNHTRZOIOQ-UHFFFAOYSA-N 1lambda2-plumbirane Chemical compound [Pb].C=C SUECSNHTRZOIOQ-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- ZPEIXKMOUCYBEB-UHFFFAOYSA-N 4-hydroxy-1,3,2,4-dioxathiaphosphetane Chemical compound S1OP(O1)O ZPEIXKMOUCYBEB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- QQZRSVQBPZQBLO-UHFFFAOYSA-N CC(C)(C)OOCC#N Chemical compound CC(C)(C)OOCC#N QQZRSVQBPZQBLO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241001508691 Martes zibellina Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- PDAVOLCVHOKLEO-UHFFFAOYSA-N acetyl benzenecarboperoxoate Chemical compound CC(=O)OOC(=O)C1=CC=CC=C1 PDAVOLCVHOKLEO-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical compound CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 description 1
- OOSPDKSZPPFOBR-UHFFFAOYSA-N butyl dihydrogen phosphite Chemical compound CCCCOP(O)O OOSPDKSZPPFOBR-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NFORZJQPTUSMRL-UHFFFAOYSA-N dipropan-2-yl hydrogen phosphite Chemical compound CC(C)OP(O)OC(C)C NFORZJQPTUSMRL-UHFFFAOYSA-N 0.000 description 1
- 125000005670 ethenylalkyl group Chemical group 0.000 description 1
- KDHCZGZBCHMXSU-UHFFFAOYSA-N ethoxy(ethylsulfanyl)phosphinous acid Chemical compound CCOP(O)SCC KDHCZGZBCHMXSU-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Substances CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KCRLWVVFAVLSAP-UHFFFAOYSA-N octyl dihydrogen phosphite Chemical compound CCCCCCCCOP(O)O KCRLWVVFAVLSAP-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- AFJBCLKQBNVDDC-UHFFFAOYSA-N propylsulfanylphosphonous acid Chemical compound CCCSP(O)O AFJBCLKQBNVDDC-UHFFFAOYSA-N 0.000 description 1
- 102000055501 telomere Human genes 0.000 description 1
- 108091035539 telomere Proteins 0.000 description 1
- 210000003411 telomere Anatomy 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent 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)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0051763 | 1967-03-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1618383B1 true DE1618383B1 (de) | 1971-10-07 |
Family
ID=7104886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671618383 Withdrawn DE1618383B1 (de) | 1967-03-09 | 1967-03-09 | Verfahren zur Herstellung von 2-Chloräthanphosphonsäureestern |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3600475A (enExample) |
| JP (1) | JPS5118417B1 (enExample) |
| AT (1) | AT280312B (enExample) |
| BE (1) | BE711999A (enExample) |
| CH (1) | CH496027A (enExample) |
| DE (1) | DE1618383B1 (enExample) |
| FR (1) | FR1558691A (enExample) |
| GB (1) | GB1216108A (enExample) |
| NL (1) | NL159673B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4108889A (en) * | 1976-11-19 | 1978-08-22 | The Procter & Gamble Company | Preparing alkane phosphonic acids and intermediates |
| JP4666093B2 (ja) | 2009-03-13 | 2011-04-06 | ユニマテック株式会社 | ポリフルオロアルキルホスホン酸エステルの製造法 |
| EP2452945B1 (en) * | 2009-07-10 | 2014-07-30 | Unimatec Co., Ltd. | Polyfluoroalkylphosphonic acid esters and processes for production of same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2957931A (en) * | 1949-07-28 | 1960-10-25 | Socony Mobil Oil Co Inc | Synthesis of compounds having a carbonphosphorus linkage |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2559754A (en) * | 1950-06-29 | 1951-07-10 | Du Pont | Fluoroalkanephosphonic compounds |
| US3064030A (en) * | 1958-06-18 | 1962-11-13 | Monsanto Chemicals | Method of preparing vinyl and substituted vinyl phosphonates by dehydro-halogenation |
-
1967
- 1967-03-09 DE DE19671618383 patent/DE1618383B1/de not_active Withdrawn
-
1968
- 1968-03-04 NL NL6803034.A patent/NL159673B/xx not_active IP Right Cessation
- 1968-03-07 CH CH336768A patent/CH496027A/de not_active IP Right Cessation
- 1968-03-07 US US711181A patent/US3600475A/en not_active Expired - Lifetime
- 1968-03-07 AT AT224068A patent/AT280312B/de not_active IP Right Cessation
- 1968-03-09 JP JP43015171A patent/JPS5118417B1/ja active Pending
- 1968-03-11 FR FR1558691D patent/FR1558691A/fr not_active Expired
- 1968-03-11 GB GB01759/68A patent/GB1216108A/en not_active Expired
- 1968-03-11 BE BE711999D patent/BE711999A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2957931A (en) * | 1949-07-28 | 1960-10-25 | Socony Mobil Oil Co Inc | Synthesis of compounds having a carbonphosphorus linkage |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1558691A (enExample) | 1969-02-28 |
| AT280312B (de) | 1970-04-10 |
| GB1216108A (en) | 1970-12-16 |
| NL159673B (nl) | 1979-03-15 |
| CH496027A (de) | 1970-09-15 |
| US3600475A (en) | 1971-08-17 |
| JPS5118417B1 (enExample) | 1976-06-09 |
| NL6803034A (enExample) | 1968-09-10 |
| BE711999A (enExample) | 1968-09-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |