US3907815A
Expired / Lapsed
US
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Process for preparing phosphorothioates and phenylphosphonothioates
Assignee: Dow Chemical Co
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Filing: 1973-05-21
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Granted: 1975-09-23
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Expires: 1993-05-21
Abstract
Abstract Mixtures of (1) a quaternary ammonium salt(s) and (2) 1,4diazabicyclo(2.2.2)octane are novel catalysts in the process of reacting an alkali metal phenate, pyridinate or pyrimidinate with an 0,0-dialkyl phosphorochloridothioate or 0-alkyl phenylphosphonochloridothioate to produce the corresponding phosphorothioates and phenylphosphonothioates. The process is conducted under alkaline conditions in a liquid reaction medium. As an example, 0,0-diethyl O-(3,5,6-trichloro-2-pyridyl)phosphorothioate is prepared in excellent yields and purity by reacting sodium 3,5,6-trichloropyridinate with 0,0-diethyl phosphorochloridothioate in a stirred methylene chloride-water reaction medium in the presence of a catalytic amount of benzyltriethylammonium chloride and 1,4diazabicyclo(2.2.2)octane.
Inventors
- 👤 Lorraine M Kroposki
- 👤 Masao Yoshimine
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 19:51
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/40; C07F9/4071; C07F9/4084; B; B01; B01J; B01J31/00; B01J31/02; B01J31/0234; B01J31/0235; B01J31/0237; B01J31/0239; C07D; C07D487/00; C07D487/02; C07D487/08; C07F9/06; C07F9/16; C07F9/165; C07F9/18; C07F9/547; C07F9/553; C07F9/576; C07F9/58; C07F9/645; C07F9/6509; C07F9/650952
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
11 words
IN THE PROCESS OF PREPARING A COMPOUND CORRESPONDING TO THE FORMULA
Claim 2
Dependent Claim
11 words
IN THE PROCESS OF PREPARING A COMPOUND CORRESPONDING TO THE FORMULA
Claim 3
Dependent Claim
112 words
The process defined in claim 1 wherein (1) is a quaternary ammonium salt of the formula R1''R2''R3''R4''N A , wherein R1''-R4'' are each independently hydrocarbyl groups of from 1 to about 12 carbon atoms, or R1'' is joined with R2'' to form a 5- or 6-membered heterocyclic ring wherein one member of said heterocyclic ring is a quaternized nitrogen atom, a second member of said heterocyclic ring is an atom of carbon or a non-adjacent atom of nitrogen, oxygen or sulfur, and the remaining members of said heterocyclic ring are carbon atoms; and A is a neutralizing anion; said quaternary ammonium salt having a maximum carbon content of about 31 carbon atoms.
Claim 4
Dependent Claim
18 words
The process defined in claim 2 wherein (1) is benzyltrimethylammonium chloride or bromide, or benzyltriethylammonium chloride or bromide.
Claim 5
Dependent Claim
11 words
The process defined in claim 3 wherein (1) is benzyltriethylammonium chloride.
Claim 6
Dependent Claim
21 words
The process defined in claim 1 wherein the mole ratio of (1) to (2) is from about 1:20 to about 20:1.
Claim 7
Dependent Claim
16 words
The process defined in claim 5 wherein said ratio is from about 1:2 to about 2:1.
Claim 8
Dependent Claim
32 words
The process defined in claim 1 wherein the combined amount of (1) and (2) is from about 0.25 to about 20 mole percent, based on the combined moles of (a) and (b).
Claim 9
Dependent Claim
23 words
The process defined in claim 7 wherein the combined amount of (1) and (2) is from about 0.5 to about 2 mole percent.
Claim 10
Dependent Claim
26 words
The process defined in claim 1 wherein said process is conducted in an agitated two-phase solvent system consisting of an inert water-immiscible organic liquid and water.
Claim 11
Dependent Claim
9 words
The process defined in claim 1 wherein R is
Claim 12
Dependent Claim
14 words
The process defined in claim 10 wherein R1 and R2 are methyl or ethyl.
Claim 13
Dependent Claim
18 words
The process defined by claim 10 wherein (1) is benzyltrimethylammonium chloride or bromide or benzyltriethylammonium chloride or bromide.
Claim 14
Dependent Claim
11 words
The process defined in claim 12 wherein (2) is benzyltriethylammonium chloride.
Claim 15
Dependent Claim
26 words
The process defined in claim 13 wherein said process is conducted in an agitated two-phase solvent system consisting of an inert water-immiscible organic liquid and water.
Claim 16
Dependent Claim
40 words
The process defined in claim 14 wherein (a) is sodium O-3,5, 6-trichloro-2-pyridinate and (b) is O,O-diethyl phosphorochloridothioate; said two-phase solvent system is a mixture of methylene chloride and water; and the reaction temperature is from about 40* to about 60*C.
References Cited (Backward Citations)
US3244586A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-09-22 | 1979-03-24 | 1979-09-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-09-22 | 1983-03-24 | 1983-09-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-09-22 | 1987-03-24 | 1987-09-23 | $7700.00 | Window Closed / Lapsed |