HU196418B - Process for producing dialkyl-esters of 3-oxo-butyl-phosphonic acids - Google Patents
Process for producing dialkyl-esters of 3-oxo-butyl-phosphonic acids Download PDFInfo
- Publication number
- HU196418B HU196418B HU833332D HU333283D HU196418B HU 196418 B HU196418 B HU 196418B HU 833332 D HU833332 D HU 833332D HU 333283 D HU333283 D HU 333283D HU 196418 B HU196418 B HU 196418B
- Authority
- HU
- Hungary
- Prior art keywords
- reaction
- dialkyl
- ester
- phosphorous acid
- mesityl oxide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- ABKXUYUUYQOJJV-UHFFFAOYSA-N 3-oxobutylphosphonic acid Chemical class CC(=O)CCP(O)(O)=O ABKXUYUUYQOJJV-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 claims abstract description 19
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 claims abstract description 19
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000002148 esters Chemical class 0.000 claims description 24
- 239000011734 sodium Substances 0.000 claims description 20
- 229910052708 sodium Inorganic materials 0.000 claims description 20
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- -1 sodium ester Chemical class 0.000 claims description 3
- 239000000203 mixture Substances 0.000 abstract description 8
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 5
- 150000001298 alcohols Chemical class 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 150000001983 dialkylethers Chemical class 0.000 abstract 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 3
- 230000003993 interaction Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000012467 final product Substances 0.000 description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- MOMJYWJXUNIBGJ-UHFFFAOYSA-N 4-dimethoxyphosphoryl-4-methylpentan-2-one Chemical compound COP(=O)(OC)C(C)(C)CC(C)=O MOMJYWJXUNIBGJ-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 238000001030 gas--liquid chromatography Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- DLQDGVZAEYZNTG-UHFFFAOYSA-N dimethyl hydrogen phosphite Chemical compound COP(O)OC DLQDGVZAEYZNTG-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CMSWHGFRLICZCA-UHFFFAOYSA-N trihydroxy(dimethyl)-$l^{5}-phosphane Chemical compound CP(C)(O)(O)O CMSWHGFRLICZCA-UHFFFAOYSA-N 0.000 description 2
- WYDXRBHQQRMGTL-UHFFFAOYSA-N 3-methyl-1-(2,4,6-trimethylphenyl)but-2-en-1-one Chemical compound CC(C)=CC(=O)c1c(C)cc(C)cc1C WYDXRBHQQRMGTL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- IYGMJRCUQOOENU-UHFFFAOYSA-N oxaphosphole Chemical class C1=COP=C1 IYGMJRCUQOOENU-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/SU1983/000049 WO1985002849A1 (en) | 1983-12-21 | 1983-12-21 | Process for obtaining dialkyl ethers of 3-oxo-butyl phosphonic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT38363A HUT38363A (en) | 1986-05-28 |
| HU196418B true HU196418B (en) | 1988-11-28 |
Family
ID=21616826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU833332D HU196418B (en) | 1983-12-21 | 1983-12-21 | Process for producing dialkyl-esters of 3-oxo-butyl-phosphonic acids |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS61500785A (ja) |
| CH (1) | CH667095A5 (ja) |
| DE (1) | DE3390565C2 (ja) |
| GB (1) | GB2160872B (ja) |
| HU (1) | HU196418B (ja) |
| WO (1) | WO1985002849A1 (ja) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200906844A (en) * | 2007-06-08 | 2009-02-16 | Albemarle Corp | Process for making dihydrocarbyl hydrocarbonphosphonates |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2612513A (en) * | 1950-08-25 | 1952-09-30 | Monsanto Chemicals | Preparation of diesters of aliphatic oxophosphonic acids |
-
1983
- 1983-12-21 DE DE19833390565 patent/DE3390565C2/de not_active Expired
- 1983-12-21 CH CH3700/85A patent/CH667095A5/de not_active IP Right Cessation
- 1983-12-21 GB GB08520308A patent/GB2160872B/en not_active Expired
- 1983-12-21 HU HU833332D patent/HU196418B/hu not_active IP Right Cessation
- 1983-12-21 WO PCT/SU1983/000049 patent/WO1985002849A1/ru active Application Filing
- 1983-12-21 JP JP84502862A patent/JPS61500785A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE3390565T1 (de) | 1985-12-12 |
| GB2160872B (en) | 1987-05-07 |
| CH667095A5 (de) | 1988-09-15 |
| DE3390565C2 (de) | 1988-01-14 |
| HUT38363A (en) | 1986-05-28 |
| JPS61500785A (ja) | 1986-04-24 |
| GB2160872A (en) | 1986-01-02 |
| GB8520308D0 (en) | 1985-09-18 |
| WO1985002849A1 (en) | 1985-07-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |