DE2406058C2 - Verfahren zur Herstellung von Allylester^ - Google Patents
Verfahren zur Herstellung von Allylester^Info
- Publication number
- DE2406058C2 DE2406058C2 DE2406058A DE2406058A DE2406058C2 DE 2406058 C2 DE2406058 C2 DE 2406058C2 DE 2406058 A DE2406058 A DE 2406058A DE 2406058 A DE2406058 A DE 2406058A DE 2406058 C2 DE2406058 C2 DE 2406058C2
- Authority
- DE
- Germany
- Prior art keywords
- copper
- butene
- diol
- carbon atoms
- isomerization
- 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
- -1 allyl ester Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 10
- 239000010949 copper Substances 0.000 claims description 10
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(i) oxide Chemical compound [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 4
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 229960004643 cupric oxide Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 9
- 238000006317 isomerization reaction Methods 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 4
- 229910052751 metal Inorganic materials 0.000 claims 4
- 239000002184 metal Substances 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 150000001880 copper compounds Chemical class 0.000 claims 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 239000000194 fatty acid Substances 0.000 claims 2
- 229930195729 fatty acid Natural products 0.000 claims 2
- 150000004665 fatty acids Chemical class 0.000 claims 2
- 150000002736 metal compounds Chemical class 0.000 claims 2
- 239000010970 precious metal Substances 0.000 claims 2
- 241000251468 Actinopterygii Species 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 239000005749 Copper compound Substances 0.000 claims 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000001879 copper Chemical class 0.000 claims 1
- XYNZKHQSHVOGHB-UHFFFAOYSA-N copper(3+) Chemical class [Cu+3] XYNZKHQSHVOGHB-UHFFFAOYSA-N 0.000 claims 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 229910000510 noble metal Inorganic materials 0.000 claims 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 150000003058 platinum compounds Chemical class 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 239000008262 pumice Substances 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 239000004575 stone Substances 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- VUIWJRYTWUGOOF-UHFFFAOYSA-N 2-ethenoxyethanol Chemical compound OCCOC=C VUIWJRYTWUGOOF-UHFFFAOYSA-N 0.000 description 1
- 150000004808 allyl alcohols Chemical class 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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)
- Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2406058A DE2406058C2 (de) | 1974-02-08 | 1974-02-08 | Verfahren zur Herstellung von Allylester^ |
| BE153057A BE825179A (fr) | 1974-02-08 | 1975-02-04 | Procede de preparation d'esters allyliques substitues |
| FR7503573A FR2260559B1 (enrdf_load_stackoverflow) | 1974-02-08 | 1975-02-05 | |
| CH137375A CH593231A5 (enrdf_load_stackoverflow) | 1974-02-08 | 1975-02-05 | |
| GB5242/75A GB1487274A (en) | 1974-02-08 | 1975-02-07 | Manufacture of substituted allyl esters |
| NLAANVRAGE7501501,A NL179904C (nl) | 1974-02-08 | 1975-02-07 | Werkwijze voor het katalytisch isomeriseren van gesubstitueerde allylesters. |
| JP50015907A JPS5934693B2 (ja) | 1974-02-08 | 1975-02-08 | 置換アルリルエステルの製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2406058A DE2406058C2 (de) | 1974-02-08 | 1974-02-08 | Verfahren zur Herstellung von Allylester^ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2406058B1 DE2406058B1 (de) | 1975-02-20 |
| DE2406058C2 true DE2406058C2 (de) | 1975-10-02 |
Family
ID=5906950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2406058A Expired DE2406058C2 (de) | 1974-02-08 | 1974-02-08 | Verfahren zur Herstellung von Allylester^ |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5934693B2 (enrdf_load_stackoverflow) |
| BE (1) | BE825179A (enrdf_load_stackoverflow) |
| CH (1) | CH593231A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2406058C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2260559B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1487274A (enrdf_load_stackoverflow) |
| NL (1) | NL179904C (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2840125A1 (de) * | 1978-09-15 | 1980-04-03 | Basf Ag | Verfahren zur herstellung von carbonsaeureestern des beta -formyl-crotylalkohols mittels einer allylumlagerung |
| DE2854154A1 (de) | 1978-12-15 | 1980-07-03 | Basf Ag | Verfahren zur herstellung von vinylglykolestern |
| DE10117065A1 (de) | 2001-04-05 | 2002-10-10 | Basf Ag | Verfahren zur Herstellung von C5-Acetat |
-
1974
- 1974-02-08 DE DE2406058A patent/DE2406058C2/de not_active Expired
-
1975
- 1975-02-04 BE BE153057A patent/BE825179A/xx not_active IP Right Cessation
- 1975-02-05 CH CH137375A patent/CH593231A5/xx not_active IP Right Cessation
- 1975-02-05 FR FR7503573A patent/FR2260559B1/fr not_active Expired
- 1975-02-07 GB GB5242/75A patent/GB1487274A/en not_active Expired
- 1975-02-07 NL NLAANVRAGE7501501,A patent/NL179904C/xx not_active IP Right Cessation
- 1975-02-08 JP JP50015907A patent/JPS5934693B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL179904B (nl) | 1986-07-01 |
| CH593231A5 (enrdf_load_stackoverflow) | 1977-11-30 |
| JPS5168515A (enrdf_load_stackoverflow) | 1976-06-14 |
| GB1487274A (en) | 1977-09-28 |
| JPS5934693B2 (ja) | 1984-08-24 |
| NL179904C (nl) | 1986-12-01 |
| BE825179A (fr) | 1975-08-04 |
| FR2260559B1 (enrdf_load_stackoverflow) | 1978-02-03 |
| DE2406058B1 (de) | 1975-02-20 |
| NL7501501A (nl) | 1975-08-12 |
| FR2260559A1 (enrdf_load_stackoverflow) | 1975-09-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |