CA1101880A - Manufacture of acetals - Google Patents
Manufacture of acetalsInfo
- Publication number
- CA1101880A CA1101880A CA279,396A CA279396A CA1101880A CA 1101880 A CA1101880 A CA 1101880A CA 279396 A CA279396 A CA 279396A CA 1101880 A CA1101880 A CA 1101880A
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- alcohol
- aldehyde
- chr
- column
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
- 150000001241 acetals Chemical class 0.000 title claims description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 47
- 238000000034 method Methods 0.000 claims abstract description 39
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 26
- 150000001299 aldehydes Chemical class 0.000 claims description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 20
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 claims description 17
- SEPQTYODOKLVSB-UHFFFAOYSA-N 3-methylbut-2-enal Chemical compound CC(C)=CC=O SEPQTYODOKLVSB-UHFFFAOYSA-N 0.000 claims description 14
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- CFWIJHYMQMETJN-UHFFFAOYSA-N 3-methyl-1,1-bis(3-methylbut-2-enoxy)but-2-ene Chemical compound CC(C)=CCOC(C=C(C)C)OCC=C(C)C CFWIJHYMQMETJN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 238000007599 discharging Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 239000007858 starting material Substances 0.000 abstract description 13
- -1 aliphatic aldehydes Chemical class 0.000 abstract description 6
- 239000013543 active substance Substances 0.000 abstract description 2
- 150000004808 allyl alcohols Chemical class 0.000 abstract description 2
- 239000004033 plastic Substances 0.000 abstract description 2
- 229920003023 plastic Polymers 0.000 abstract description 2
- 239000011782 vitamin Substances 0.000 abstract description 2
- 235000013343 vitamin Nutrition 0.000 abstract description 2
- 229940088594 vitamin Drugs 0.000 abstract description 2
- 229930003231 vitamin Natural products 0.000 abstract description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 11
- 150000001298 alcohols Chemical class 0.000 description 11
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 10
- 238000006359 acetalization reaction Methods 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 2
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 2
- VEEFADFWCHSFIU-UHFFFAOYSA-N 3-methylbut-3-enal Chemical compound CC(=C)CC=O VEEFADFWCHSFIU-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
- WCASXYBKJHWFMY-UHFFFAOYSA-N crotyl alcohol Chemical compound CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000011552 falling film Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QXQQCYKFELYFGP-UHFFFAOYSA-N (2-methyl-4-oxobut-2-enyl) acetate Chemical compound CC(=O)OCC(C)=CC=O QXQQCYKFELYFGP-UHFFFAOYSA-N 0.000 description 1
- YUPLKMBETLTBOZ-UHFFFAOYSA-N 1,1-bis(2-methylprop-2-enoxy)but-2-ene Chemical compound CC(=C)COC(C=CC)OCC(C)=C YUPLKMBETLTBOZ-UHFFFAOYSA-N 0.000 description 1
- ZQAYBCWERYRAMF-UHFFFAOYSA-N 1-methoxy-3-methylbutane Chemical compound COCCC(C)C ZQAYBCWERYRAMF-UHFFFAOYSA-N 0.000 description 1
- WGECXQBGLLYSFP-UHFFFAOYSA-N 2,3-dimethylpentane Chemical compound CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 1
- ACWQBUSCFPJUPN-UHFFFAOYSA-N 2-methylbut-2-enal Chemical compound CC=C(C)C=O ACWQBUSCFPJUPN-UHFFFAOYSA-N 0.000 description 1
- OEFHASHQBKCDRV-UHFFFAOYSA-N 2-propan-2-ylbut-2-enal Chemical compound CC=C(C=O)C(C)C OEFHASHQBKCDRV-UHFFFAOYSA-N 0.000 description 1
- HIRRVCGCROZFLZ-UHFFFAOYSA-N 3,7-dimethyl-1-(3-methylbut-2-enoxy)octa-2,6-diene Chemical compound CC(C)=CCCC(C)=CCOCC=C(C)C HIRRVCGCROZFLZ-UHFFFAOYSA-N 0.000 description 1
- 229930008411 3,7-dimethylocta-2,6-dien-1-ol Natural products 0.000 description 1
- UATRONWBYDQKSQ-UHFFFAOYSA-N 3-methyl-1-(3-methylbut-2-enoxy)but-2-ene Chemical compound CC(C)=CCOCC=C(C)C UATRONWBYDQKSQ-UHFFFAOYSA-N 0.000 description 1
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 1
- HGZHXGDXKCVYFS-UHFFFAOYSA-N 4-methoxy-2-methylbut-2-enal Chemical compound COCC=C(C)C=O HGZHXGDXKCVYFS-UHFFFAOYSA-N 0.000 description 1
- BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical compound C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
-
- 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
- C07C69/73—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 unsaturated acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2625074.8 | 1976-06-04 | ||
| DE2625074A DE2625074C3 (de) | 1976-06-04 | 1976-06-04 | Verfahren zur Herstellung von Acetalen |
| DEP2714590.0 | 1977-04-01 | ||
| DE2714590A DE2714590C2 (de) | 1977-04-01 | 1977-04-01 | Verfahren zur Herstellung von Acetalen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1101880A true CA1101880A (en) | 1981-05-26 |
Family
ID=25770533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA279,396A Expired CA1101880A (en) | 1976-06-04 | 1977-05-30 | Manufacture of acetals |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4133836A (enExample) |
| JP (1) | JPS52148009A (enExample) |
| CA (1) | CA1101880A (enExample) |
| CH (1) | CH631147A5 (enExample) |
| FR (1) | FR2353512A1 (enExample) |
| GB (1) | GB1576852A (enExample) |
| NL (1) | NL190579C (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2656604B1 (fr) * | 1990-01-03 | 1992-03-20 | Rhone Poulenc Sante | Procede de preparation du citral. |
| US5804702A (en) * | 1996-02-14 | 1998-09-08 | Southwest Sciences Incorporated | Process for reducing interfering signals in optical measurements of water vapor |
| DE10044352A1 (de) | 2000-09-07 | 2002-03-21 | Basf Ag | Kontinuierliches Verfahren zur Herstellung von Acetalen |
| CN104788295B (zh) * | 2015-03-19 | 2016-08-31 | 万华化学集团股份有限公司 | 一种3-甲基-2-丁烯-1-醛二异戊烯基缩醛的制备方法 |
| BR112020017125A2 (pt) | 2018-02-28 | 2020-12-22 | Kuraray Co., Ltd | Composição para remoção de compostos contendo enxofre |
| CN109438196B (zh) * | 2018-11-05 | 2021-08-17 | 山东新和成维生素有限公司 | 一种制备2,2-二甲氧基丙烷的方法 |
| CN114516786B (zh) * | 2020-11-19 | 2023-05-26 | 万华化学集团股份有限公司 | 一种光催化制备柠檬醛中间体的方法 |
| CN115141090B (zh) * | 2021-03-29 | 2024-05-17 | 中国石油化工股份有限公司 | 一种烯醛的制备方法 |
| CN113979843A (zh) * | 2021-09-23 | 2022-01-28 | 国药集团威奇达药业有限公司 | 一种直接催化裂解制备烯基醚的方法 |
| CN113999093B (zh) * | 2021-09-23 | 2024-08-09 | 国药集团威奇达药业有限公司 | 一种制备缩醛的方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2691049A (en) * | 1954-10-05 | Process fob the production of | ||
| US2573678A (en) * | 1951-11-06 | Preparation and pyrolysis of satu | ||
| US2800513A (en) * | 1957-07-23 | Manufacture of trialkoxyalkanes | ||
| US2501144A (en) * | 1947-12-19 | 1950-03-21 | Hercules Powder Co Ltd | Unsaturated aldehydes and preparation thereof |
| US2848500A (en) * | 1957-01-28 | 1958-08-19 | Du Pont | Preparation of purified formaldehyde |
| SU121443A1 (ru) * | 1958-10-22 | 1958-11-30 | Д.М. Винокуров | Способ получени формалей |
| FR1444800A (fr) * | 1965-05-24 | 1966-07-08 | Electrochimie Soc | Procédé de préparation d'alpha-allylaldéhydes |
| US3819720A (en) * | 1972-08-16 | 1974-06-25 | Union Carbide Corp | Substituted tetramethoxy derivatives |
| CH597128A5 (enExample) * | 1973-03-12 | 1978-03-31 | Hoffmann La Roche | |
| US3978092A (en) * | 1973-05-14 | 1976-08-31 | Teijin Limited | Process for the preparation of unsaturated carbonyl compounds |
-
1977
- 1977-05-25 NL NL7705771A patent/NL190579C/xx not_active IP Right Cessation
- 1977-05-30 CA CA279,396A patent/CA1101880A/en not_active Expired
- 1977-05-31 US US05/801,561 patent/US4133836A/en not_active Expired - Lifetime
- 1977-06-01 CH CH672077A patent/CH631147A5/de not_active IP Right Cessation
- 1977-06-02 GB GB23378/77A patent/GB1576852A/en not_active Expired
- 1977-06-03 FR FR7717146A patent/FR2353512A1/fr active Granted
- 1977-06-03 JP JP6490877A patent/JPS52148009A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1576852A (en) | 1980-10-15 |
| NL7705771A (nl) | 1977-12-06 |
| FR2353512B1 (enExample) | 1981-02-20 |
| JPS6229419B2 (enExample) | 1987-06-25 |
| US4133836A (en) | 1979-01-09 |
| NL190579C (nl) | 1994-05-02 |
| CH631147A5 (de) | 1982-07-30 |
| JPS52148009A (en) | 1977-12-08 |
| NL190579B (nl) | 1993-12-01 |
| FR2353512A1 (fr) | 1977-12-30 |
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