SU243616A1 - Method of producing sulfate phosphonates - Google Patents
Method of producing sulfate phosphonatesInfo
- Publication number
- SU243616A1 SU243616A1 SU1239281A SU1239281A SU243616A1 SU 243616 A1 SU243616 A1 SU 243616A1 SU 1239281 A SU1239281 A SU 1239281A SU 1239281 A SU1239281 A SU 1239281A SU 243616 A1 SU243616 A1 SU 243616A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- phosphonates
- bis
- calculated
- found
- formula
- Prior art date
Links
- GWFHMIQULJFCNC-UHFFFAOYSA-N OP(O)=O.OS(O)(=O)=O Chemical class OP(O)=O.OS(O)(=O)=O GWFHMIQULJFCNC-UHFFFAOYSA-N 0.000 title 1
- -1 2,2-bis- (vinylsulfonyloxy-2, 6-dichlorophenyl) -propane Chemical compound 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- AQSJGOWTSHOLKH-UHFFFAOYSA-N Phosphite Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- LQHYUUBBIJGBNR-UHFFFAOYSA-L OS(=O)(=O)P([O-])([O-])=O Chemical class OS(=O)(=O)P([O-])([O-])=O LQHYUUBBIJGBNR-UHFFFAOYSA-L 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- VTWRFRVMKPWCFL-UHFFFAOYSA-N diethyl phosphite Chemical compound CCOP([O-])OCC VTWRFRVMKPWCFL-UHFFFAOYSA-N 0.000 description 1
- RFLXPWJUUKBPJG-UHFFFAOYSA-N dipropyl phosphite Chemical compound CCCOP([O-])OCCC RFLXPWJUUKBPJG-UHFFFAOYSA-N 0.000 description 1
- 230000000855 fungicidal Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к способу получени неописанных сульфофосфонатов общей формулы ;RO)2PCH2CH2S020-Ar-OSO2CH2CH2P(OR)2 IIII Оо где R - алкил, арил, Аг - арилен. .С1 1) (C H OlaPCHjCHjgOjO ОС1The invention relates to a process for the preparation of undescribed sulfophosphonates of the general formula; RO) 2PCH2CH2S020-Ar-OSO2CH2CH2P (OR) 2 IIII Oo where R is alkyl, aryl, Ar is arylene. .C1 1) (C H OlaPCHjCHjgOjO OS1
получают из смеси 0,005 г-моль 2,2-бис-(винилсульфонилокси-2 ,6-дихлорфенил) - пропана, 0,012 г-моль дибутилфосфита и 0,001 г-моль насыщенного раствора метилата натри в метаноле , которую кип т т в 70 мл ксилола з течение 8 час. Реакционную массу промывают раствором соды, затем водой, сушат над сульфатом натри , отгон юг растворитель и получают продукт в виде масл нистой жидкости. Выход 73,0%; df 1,2552; по 1,5041.obtained from a mixture of 0.005 g-mole of 2,2-bis- (vinylsulfonyloxy-2, 6-dichlorophenyl) -propane, 0.012 g-mol of dibutylphosphite and 0.001 g-mol of a saturated solution of sodium methylate in methanol, which is boiled in 70 ml of xylene h for 8 hours The reaction mass is washed with a solution of soda, then with water, dried over sodium sulfate, the solvent is distilled off and a product is obtained in the form of an oily liquid. Yield 73.0%; df 1.2552; at 1.5041.
При сто нии вещество кристаллизуетс (т. пл. 133-135°С из спирта). Найдено, %: С1 15,64; Р 6,32; S 7,04.Upon standing, the substance crystallizes (mp pl. 133-135 ° C from alcohol). Found,%: C1 15.64; P 6.32; S 7.04.
СззНз4С14О12Р252.SzzNz4S14O12R252.
Вычислено, %: С1 15,22; Р 6,64; S 6,86. Пример 2. Соединение формулы Указанные соединени могут быть получены взаимодействием бис- (винилсульфонил) -фенола с диалкил (арил) фосфитами в присутствии щелочных катализаторов, например алкогол тов щелочных металлов, в среде органического растворител , например ксилоле. Процесс ведут при температуре 120-145°С. Полученные соединени могут быть использованы в качестве фунгицидов. Пример 1. Соединение формулы OSOaCHoCHjPfOC Hgla получают аналогично примеру 1 из 0,01 г-моль бис-(винилсульфонил)-гидрохинона и 0,22 гмоль дибутилфосфита. Выход 61,9%; df 1,1182; п2о 1,4480; найдено MRo 162,51; вычислено MR 160,39. 3) (CjH OgPCHjCH SOgO получают в услови х примера 1 из 0,015 г-моль 2,2-бис-(винилсульфонилокси-2,6 - дибромфенил )-пропана и 0,033 г-моль дипропилфосфита . Выход 95,5%; т. пл. 187-188°С (из спирта ). С1 4) (СгН5С)2РСНгСН28020 ОС1Calculated,%: C1 15.22; P 6.64; S 6.86. Example 2. Compound of Formula These compounds can be prepared by reacting bis (vinylsulfonyl) phenol with dialkyl (aryl) phosphites in the presence of alkaline catalysts, for example, alkali metal alkoxides, in an organic solvent, for example xylene. The process is conducted at a temperature of 120-145 ° C. The compounds obtained can be used as fungicides. Example 1. A compound of the formula OSOaCHoCHjPfOC Hgla is prepared analogously to example 1 from 0.01 gm mol of bis- (vinylsulfonyl) -hydroquinone and 0.22 gmol dibutyl phosphite. Yield 61.9%; df 1.1182; p2o 1.4480; found MRo 162.51; calculated MR 160.39. 3) (CjH OgPCHjCH SOgO is obtained under the conditions of Example 1 from 0.015 gmol of 2,2-bis- (vinylsulfonyloxy-2,6-dibromophenyl) propane and 0.033 gmol dipropylphosphite. Yield 95.5%; mp. 187-188 ° C (from alcohol). C1 4) (CrH5C) 2PCNgSN28020 OC1
получают аналогично примеру 1 из 0,02 г-моль 2,2-бис-(винйлсульфонилокси-2,6 - дихлорфенил )-пропана и 0,044 г-моль диэтилфосфита. Выход 75,7%, т. пл. 164-165°С (из спирта).was prepared as in Example 1, from 0.02 gmol of 2,2-bis- (vinylsulfonyloxy-2,6-dichlorophenyl) propane and 0.044 gmol of diethylphosphite. Output 75.7%, so pl. 164-165 ° C (from alcohol).
получают аналогично предыдущему из 0,01 г-моль 2,2-бис-(винилсульфонил-2,6-дихлорфенил )-пропана и 0,022 г-моль дифеиилфосфита . Выход 96,5%, т. пл. 90-9ГС (из спирта).similarly to the previous one, they are obtained from 0.01 g mol of 2,2-bis- (vinylsulfonyl-2,6-dichlorophenyl) propane and 0.022 g mol of dipheiyl phosphite. The output of 96.5%, so pl. 90-9GS (from alcohol).
Найдено, %: С1 13,91; Р 5,82; S 6,84.Found,%: C1 13.91; P 5.82; S 6.84.
С4зНз8С14О12Р282.С4зНз8С14О12Р282.
Вычислено, %: С1 14,00; Р 6,12; S 6,32.Calculated,%: C1 14.00; P 6.12; S 6.32.
Предмет изобретени Subject invention
Способ получени сульфофосфонатов общей формулыThe method of producing sulfophosphonates of the general formula
Найдено, %: С1 17,48; Р 7,14; S 7,99.Found,%: C1 17.48; P 7.14; S 7.99.
C27H38Cl4Oi2P2S2.C27H38Cl4Oi2P2S2.
Вычислено, %: С1 17,32; Р 7,57; S 7,82. Пример 5. Соединение формулыCalculated,%: C1 17.32; P 7.57; S 7.82. Example 5. The compound of the formula
С1C1
СНзSNS
OSOaCHsCHsPfOCgHsla OSOaCHsCHsPfOCgHsla
I он. С1, ОI he. C1, O
15 (RO)2PCH2CH2SO2O-Аг-CSO2CH2CH2P(OR),15 (RO) 2PCH2CH2SO2O-Ar-CSO2CH2CH2P (OR),
где R - алкил, арил, Аг - арилен.where R is alkyl, aryl, Ar - Allen.
отличающийс тем, что бис-(винилсульфончл)фенолы подвергают взаимодействию с диалкил (арил) фосфитами в присутствии щелочных катализаторов, например алкогол тов щелочных металлов, в среде органического растворител , например, ксилоле, и процесс ведут при температуре 120-145°С с последующим выделением полученного продукта известным способом. Найдено, %: Р 9,38; S 8,86. C2eH480i2P2S2. Вычислено, %: Р 9,14; S 9,44. П Р и м е Р 3. Соединение формулы С-( /-0§О СН2СНгР(ОСзН7)2 СНз ,о Найдено, %: Вг 30,78; Р 5,42; S 6,36. Сз1Н4бВГ4012Р252. Вычислено, %: Вг 30,31; Р 5,87; S 6,06. Пример 4. Соединение формулы 0802СН2СНгР{ОСгН5)2 С1Оcharacterized in that bis- (vinylsulfonyl) phenols are reacted with dialkyl (aryl) phosphites in the presence of alkaline catalysts, for example, alkali metal alcoholates, in an organic solvent, for example xylene, and the process is carried out at a temperature of 120-145 ° C, followed by the selection of the obtained product in a known manner. Found,%: P 9.38; S 8,86. C2eH480i2P2S2. Calculated,%: P 9,14; S 9.44. EXAMPLE 3. Compound of the formula C- (/ -0§О CH2CHNR (OSSN7) 2 CH3, o Found,%: Br 30.78; P 5.42; S 6.36. Cz1H4bVG4012R252. Calculated,% : Br 30.31; P 5.87; S 6.06. Example 4. Compound of the formula 0802СН2СНгР {ОСгН5) 2 С1О
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU243616A1 true SU243616A1 (en) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4059432A (en) * | 1974-05-27 | 1977-11-22 | Mitsubishi Petrochemical Co., Ltd. | Plant growth regulator |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4059432A (en) * | 1974-05-27 | 1977-11-22 | Mitsubishi Petrochemical Co., Ltd. | Plant growth regulator |
| US4059431A (en) * | 1974-05-27 | 1977-11-22 | Mitsubishi Petrochemical Co., Ltd. | Plant growth regulator |
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