DE2404776C2 - Verfahren zur Herstellung von β-Alkoxy-buttersäurealkylestern - Google Patents
Verfahren zur Herstellung von β-Alkoxy-buttersäurealkylesternInfo
- Publication number
- DE2404776C2 DE2404776C2 DE2404776A DE2404776A DE2404776C2 DE 2404776 C2 DE2404776 C2 DE 2404776C2 DE 2404776 A DE2404776 A DE 2404776A DE 2404776 A DE2404776 A DE 2404776A DE 2404776 C2 DE2404776 C2 DE 2404776C2
- Authority
- DE
- Germany
- Prior art keywords
- allyl
- butyric acid
- mol
- acid alkyl
- alkoxy
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 19
- -1 allyl halide Chemical class 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims description 4
- HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000011734 sodium Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- FASUFOTUSHAIHG-UHFFFAOYSA-N 3-methoxyprop-1-ene Chemical group COCC=C FASUFOTUSHAIHG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000006315 carbonylation Effects 0.000 description 2
- 238000005810 carbonylation reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- RJUIDDKTATZJFE-NSCUHMNNSA-N (e)-but-2-enoyl chloride Chemical compound C\C=C\C(Cl)=O RJUIDDKTATZJFE-NSCUHMNNSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001448862 Croton Species 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 description 1
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- OKOSPWNNXVDXKZ-UHFFFAOYSA-N but-3-enoyl chloride Chemical compound ClC(=O)CC=C OKOSPWNNXVDXKZ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000009838 combustion analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- AVVCQNALUKIMSP-UHFFFAOYSA-N ethyl 3-ethoxybutanoate Chemical compound CCOC(C)CC(=O)OCC AVVCQNALUKIMSP-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UJBNVYLBVGMXPI-UHFFFAOYSA-N methyl 2-methoxybutanoate Chemical compound CCC(OC)C(=O)OC UJBNVYLBVGMXPI-UHFFFAOYSA-N 0.000 description 1
- GITITJADGZYSRL-UHFFFAOYSA-N methyl but-3-enoate Chemical compound COC(=O)CC=C GITITJADGZYSRL-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture 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
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2404776A DE2404776C2 (de) | 1974-02-01 | 1974-02-01 | Verfahren zur Herstellung von β-Alkoxy-buttersäurealkylestern |
| US05/544,022 US3980697A (en) | 1974-02-01 | 1975-01-24 | Butyric acid esters |
| GB397975A GB1472515A (en) | 1974-02-01 | 1975-01-29 | Process for the production of beta-alkoxy butyric acid alkyl esters |
| BE152814A BE824908A (fr) | 1974-02-01 | 1975-01-29 | Procede de preparation d'esters alkyliques d'acides beta-alcoxybutyriques |
| JP50012950A JPS50106921A (en, 2012) | 1974-02-01 | 1975-01-30 | |
| IT47929/75A IT1029410B (it) | 1974-02-01 | 1975-01-30 | Procedimento per la produzione di beta alcossi butirrati alchilici |
| FR7502923A FR2259808B1 (en, 2012) | 1974-02-01 | 1975-01-30 | |
| NL7501179A NL7501179A (nl) | 1974-02-01 | 1975-01-31 | Werkwijze voor het bereiden van (beta)-alkoxyboter- lkylester. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2404776A DE2404776C2 (de) | 1974-02-01 | 1974-02-01 | Verfahren zur Herstellung von β-Alkoxy-buttersäurealkylestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2404776A1 DE2404776A1 (de) | 1975-08-21 |
| DE2404776C2 true DE2404776C2 (de) | 1983-01-27 |
Family
ID=5906301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2404776A Expired DE2404776C2 (de) | 1974-02-01 | 1974-02-01 | Verfahren zur Herstellung von β-Alkoxy-buttersäurealkylestern |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3980697A (en, 2012) |
| JP (1) | JPS50106921A (en, 2012) |
| BE (1) | BE824908A (en, 2012) |
| DE (1) | DE2404776C2 (en, 2012) |
| FR (1) | FR2259808B1 (en, 2012) |
| GB (1) | GB1472515A (en, 2012) |
| IT (1) | IT1029410B (en, 2012) |
| NL (1) | NL7501179A (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090081154A1 (en) * | 2006-06-15 | 2009-03-26 | Hiscox William C | Attractant composition for yellowjackets |
| JP5663765B2 (ja) * | 2010-09-08 | 2015-02-04 | 株式会社Moresco | ２塩基酸エステル化合物および該化合物を含む潤滑油基油組成物 |
| US9783520B2 (en) | 2014-05-16 | 2017-10-10 | P2 Science, Inc. | Macrocyclic compounds, polymers, and methods for making same |
| CA2959532C (en) | 2014-08-29 | 2020-03-10 | P2 Science, Inc. | Polyethers, polyamines, polythioethers, and methods for making same |
| JP7665178B2 (ja) | 2017-07-31 | 2025-04-21 | ピー２・サイエンス・インコーポレイテッド | ポリエーテル誘導体、その使用および製造方法 |
| CA3093127A1 (en) | 2018-03-07 | 2019-09-12 | P2 Science, Inc. | Polyether derivatives, uses, and methods of making the same |
| CN113454055B (zh) * | 2019-01-17 | 2024-07-05 | 凯托利皮克斯治疗有限责任公司 | 生产包含基于羟基羧酸的甘油酯的结构单元的脂质的方法 |
| AU2021231700C1 (en) | 2020-03-05 | 2025-01-23 | P2 Science, Inc. | Cosmetic compositions comprising polyether polymers |
| US12209069B2 (en) | 2021-05-17 | 2025-01-28 | P2 Science, Inc. | Fatty acid terpene alcohol esters |
| US12215120B1 (en) | 2021-05-17 | 2025-02-04 | P2 Science, Inc. | Terpene O-glycosides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3338961A (en) * | 1964-01-30 | 1967-08-29 | Ethyl Corp | Promoted catalytic carbonylation of allylic halides |
| US3457299A (en) * | 1968-03-28 | 1969-07-22 | Ethyl Corp | Process for preparing carboxylates from olefin halides and carbon monoxide |
| US3636082A (en) * | 1969-01-03 | 1972-01-18 | Du Pont | Carbonylation of organic halides with metallic alcoholates |
-
1974
- 1974-02-01 DE DE2404776A patent/DE2404776C2/de not_active Expired
-
1975
- 1975-01-24 US US05/544,022 patent/US3980697A/en not_active Expired - Lifetime
- 1975-01-29 GB GB397975A patent/GB1472515A/en not_active Expired
- 1975-01-29 BE BE152814A patent/BE824908A/xx unknown
- 1975-01-30 JP JP50012950A patent/JPS50106921A/ja active Pending
- 1975-01-30 IT IT47929/75A patent/IT1029410B/it active
- 1975-01-30 FR FR7502923A patent/FR2259808B1/fr not_active Expired
- 1975-01-31 NL NL7501179A patent/NL7501179A/xx not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2404776A1 (de) | 1975-08-21 |
| FR2259808A1 (en, 2012) | 1975-08-29 |
| GB1472515A (en) | 1977-05-04 |
| JPS50106921A (en, 2012) | 1975-08-22 |
| US3980697A (en) | 1976-09-14 |
| NL7501179A (nl) | 1975-08-05 |
| FR2259808B1 (en, 2012) | 1978-06-23 |
| BE824908A (fr) | 1975-05-15 |
| IT1029410B (it) | 1979-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |