SU451702A1 - The method of obtaining eight-membered heterocyclic organophosphorus compounds - Google Patents
The method of obtaining eight-membered heterocyclic organophosphorus compoundsInfo
- Publication number
- SU451702A1 SU451702A1 SU1893113A SU1893113A SU451702A1 SU 451702 A1 SU451702 A1 SU 451702A1 SU 1893113 A SU1893113 A SU 1893113A SU 1893113 A SU1893113 A SU 1893113A SU 451702 A1 SU451702 A1 SU 451702A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- membered heterocyclic
- organophosphorus compounds
- obtaining
- triethanolamine
- heterocyclic organophosphorus
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- -1 heterocyclic organophosphorus compounds Chemical class 0.000 title claims description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 244000007853 Sarothamnus scoparius Species 0.000 description 1
- KCIAQDIRYXMSCO-UHFFFAOYSA-N acetic acid phenylmethanol propan-2-one Chemical compound CC(C)=O.CC(O)=O.OCC1=CC=CC=C1 KCIAQDIRYXMSCO-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- GJWAEWLHSDGBGG-UHFFFAOYSA-N hexylphosphonic acid Chemical compound CCCCCCP(O)(O)=O GJWAEWLHSDGBGG-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000013522 vodka Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к области фосфорорганической ХИМИИ, а именно к способу получени новых восьмичленных гетероциклических фосфорорганических соединений общей формулы odH2(JH2 Н-СНзСНзОН (I) .сн/ где R - алкил Сб-СиЭти соединени могут найти применение в качестве смачивающих, антисептических, очищающих средств, флотореагентов, ингибиторов коррозии, а также активной основы в косметических И МОЮЩИХ КОМПОЗИЦИЯХ. Предлагаемый способ получени соединений формулы (I) основан на известном способе получени гетероциклических соединений фосфора взаимодействием дигалоидангидридов фосфоновых КИСЛОТ с аминоспиртами в присутствии пиридина И заключаетс в том, что дихлорангидриды соответствующих алкилфосфоновых КИСЛОТ подвергают взаимодействию с триэтаноламином в среде органического растворител , например хлороформа. Дихлорангидрид алкилфосфоновой кислоты И триэтаноламин желательно использовать в соотношении 1 : 3 соответственно. Целевые продукты выдел ют при помощи хроматографической колонки, заполненной ОКИСЬЮ алюмини . Они представл ют собой светло-коричневые густые масла, растворимые в воде, низщих спиртах, галоидуглеводородах И нерастворимые в эфире. Чистоту продукта контролируют тонкослойной хроматографией на окиси алюмини в системе толуол - этанол (9 : 1) и бензол - метанол - ацетон - уксусна кислота (70 : 20 : :5:5). Про витель - пары йода. Строение полученных продуктов доказано данными элементного анализа, ИК-спектров, масс- И ЯМР-спектров. В ИК-спектрах найдены полосы, соответствующие колебани м Р-О-С (1050 см-), Р 0 (1230 см-1), Р-С (940, 780 см-) и ОН (3350-3340 см-1) св зей. Пример. Диэтил-р,р - (Ы-этокси)-гексилфосфонат . В трехгорлую колбу, снабженную мещалкой , обратным ХОЛОДИЛЬНИКОМ и капельной воронкой , помещают 44,7 г (0,3 моль) сухого, перегнанного триэтаноламина в 50 мл сухого хлороформа. К этому раствору в течение 2,5 час прикапывают 20,3 г (0,1 моль) дихлоракгидрида гексилфосфоновой кислоты в 30 мл хлороформа. Реакционную смесь оставл ютThis invention relates to the field of organophosphorus CHEMISTRY, in particular, to a method for producing new eight-membered heterocyclic organophosphorus compounds of the general formula odH2 (JH2 H-CH3CH2OH (I) sn / R) alkyl C.C. , flotation reagents, corrosion inhibitors, as well as an active base in cosmetic AND WASHING COMPOSITIONS. The proposed method for producing compounds of formula (I) is based on the known method of producing heterocyclic compounds of phospho and by the interaction of phosphonic ACID dihalogen anhydrides with amino alcohols in the presence of pyridine, I conclude that the corresponding alkyl alkylphosphonic ACID dichlorohydrides are reacted with triethanolamine in an organic solvent, for example chloroform. using a chromatographic column filled with OXIDE aluminum. They are light brown thick oils, soluble in water, lower alcohols, halohydrocarbons, and insoluble in ether. The purity of the product is controlled by thin-layer chromatography on alumina in the system toluene - ethanol (9: 1) and benzene - methanol - acetone - acetic acid (70: 20:: 5: 5). About the vodka - iodine vapor The structure of the obtained products was proved by the data of elemental analysis, IR spectra, and mass and NMR spectra. In the IR spectra, bands corresponding to oscillations Р-О-С (1050 cm-), Р 0 (1230 cm-1), Р-С (940, 780 cm-) and ОН (3350-3340 cm-1) were found. communications Example. Diethyl-p, p - (Y-ethoxy) -hexylphosphonate. 44.7 g (0.3 mol) of dry, distilled triethanolamine in 50 ml of dry chloroform are placed in a three-necked flask equipped with a broom, a reverse REFRIGERATOR and an addition funnel. 20.3 g (0.1 mol) of hexylphosphonic acid dichlorohydride in 30 ml of chloroform are added dropwise to this solution for 2.5 hours. The reaction mixture is left
fc , . 4 fc,. four
на ночь. Затем отфильтров1 в1|э jSbi.atocv, {выход 90,3% от теории) диэтил-р,р-(Ы-этолую соль триэтаноламина (. l76 - lJ7,Cj); кси)-гексилфосфоната.for the night. Then, filters 1 B1 | e jSbi.atocv, {yield 90.3% of theory) diethyl-p, p- (L-etoloy triethanolamine salt (. L76 - lJ7, Cj); xi) -hexylphosphonate.
нромывают ее хлороформом, а из фильтратаСоединени , приведенные в таблице, полупосле удалени растворител выдел ют 25,3 гчены в аналогичных услови х. Выходы и данные элементарного анализа днэтил-;, -(М-этокси)-алкилфосфонатов общей формулы /ОСНзСИгч в-р(;к-сн2СН25н (Ч цЧш.сн / blot it with chloroform, and from the filtrate of the Compounds in the table, half-after removal of the solvent, 25.3 grams are isolated under the same conditions. The outputs and the data of elemental analysis of dethyl- ;, - (M-ethoxy) -alkylphosphonates of the general formula / OCHZSigch in-p (; c-sn2CH25n (H ccshsn /
Предмет изобретени Subject invention
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1893113A SU451702A1 (en) | 1973-03-12 | 1973-03-12 | The method of obtaining eight-membered heterocyclic organophosphorus compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1893113A SU451702A1 (en) | 1973-03-12 | 1973-03-12 | The method of obtaining eight-membered heterocyclic organophosphorus compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU451702A1 true SU451702A1 (en) | 1974-11-30 |
Family
ID=20545341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1893113A SU451702A1 (en) | 1973-03-12 | 1973-03-12 | The method of obtaining eight-membered heterocyclic organophosphorus compounds |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU451702A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5348670A (en) * | 1990-05-18 | 1994-09-20 | The Elco Corporation | Phosphorous amine lubricant additives |
-
1973
- 1973-03-12 SU SU1893113A patent/SU451702A1/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5348670A (en) * | 1990-05-18 | 1994-09-20 | The Elco Corporation | Phosphorous amine lubricant additives |
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