DE2340929A1 - Verfahren zur herstellung von maleinsaeureanhydrid - Google Patents
Verfahren zur herstellung von maleinsaeureanhydridInfo
- Publication number
- DE2340929A1 DE2340929A1 DE19732340929 DE2340929A DE2340929A1 DE 2340929 A1 DE2340929 A1 DE 2340929A1 DE 19732340929 DE19732340929 DE 19732340929 DE 2340929 A DE2340929 A DE 2340929A DE 2340929 A1 DE2340929 A1 DE 2340929A1
- Authority
- DE
- Germany
- Prior art keywords
- column
- water
- maleic acid
- alcohol
- monohydric alcohol
- 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.)
- Pending
Links
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 title claims description 32
- 238000004519 manufacturing process Methods 0.000 title description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 56
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 47
- 239000011976 maleic acid Substances 0.000 claims description 47
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid group Chemical group C(\C=C/C(=O)O)(=O)O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 29
- 238000004821 distillation Methods 0.000 claims description 28
- 238000006297 dehydration reaction Methods 0.000 claims description 26
- 230000018044 dehydration Effects 0.000 claims description 25
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 19
- 239000000047 product Substances 0.000 claims description 19
- 238000009835 boiling Methods 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000001530 fumaric acid Substances 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 238000011084 recovery Methods 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000006356 dehydrogenation reaction Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000002699 waste material Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- -1 η-butene Chemical compound 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- 239000005968 1-Decanol Substances 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012045 crude solution Substances 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/593—Dicarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/60—Maleic acid esters; Fumaric acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US283639A US3862147A (en) | 1972-08-25 | 1972-08-25 | Maleic anhydride process |
| GB5255974A GB1437898A (en) | 1972-08-25 | 1974-12-05 | Preparation of esters of maleic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2340929A1 true DE2340929A1 (de) | 1974-03-07 |
Family
ID=26267085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732340929 Pending DE2340929A1 (de) | 1972-08-25 | 1973-08-13 | Verfahren zur herstellung von maleinsaeureanhydrid |
Country Status (6)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3979443A (en) * | 1972-08-25 | 1976-09-07 | Petro-Tex Chemical Corporation | Process for the preparation of esters of maleic acid with monohydric alcohols |
| US4032458A (en) * | 1975-08-08 | 1977-06-28 | Petro-Tex Chemical Corporation | Production of 1,4-butanediol |
| DE3114320A1 (de) * | 1981-04-09 | 1982-10-28 | Hoechst Ag, 6000 Frankfurt | "verfahren zur herstellung von maleinsaeuredialkylestern" |
| GB8618888D0 (en) * | 1986-08-01 | 1986-09-10 | Davy Mckee Ltd | Process |
| US5840285A (en) * | 1991-12-11 | 1998-11-24 | Bernel Chemical Co., Inc | Dermatological compositions using a series of unusually safe esters as cosmetic emollients with unique and ideal physical properties |
| JP4628653B2 (ja) * | 2003-05-19 | 2011-02-09 | 株式会社日本触媒 | 無水マレイン酸の蒸留残渣の処理方法 |
| GB0325530D0 (en) | 2003-10-31 | 2003-12-03 | Davy Process Techn Ltd | Process |
| CN101314564A (zh) * | 2007-06-01 | 2008-12-03 | 上海焦化有限公司 | 马来酸二甲酯的制备方法 |
| CN112759568B (zh) * | 2019-11-01 | 2022-08-19 | 中国石油化工股份有限公司 | 处理含苯干气并制取顺酐的方法和装置 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3527677A (en) * | 1969-03-06 | 1970-09-08 | Goodrich Co B F | Process for dehydration of aqueous acrylic acid solutions by extractive - azeotropic distillation with 2-ethylhexanol or 2-ethylhexylacrylate |
-
1972
- 1972-08-25 US US283639A patent/US3862147A/en not_active Expired - Lifetime
-
1973
- 1973-07-19 CA CA176,830A patent/CA1009661A/en not_active Expired
- 1973-08-13 DE DE19732340929 patent/DE2340929A1/de active Pending
- 1973-08-24 JP JP48094503A patent/JPS4956916A/ja active Pending
- 1973-08-24 GB GB4015873A patent/GB1436879A/en not_active Expired
- 1973-08-24 FR FR7330848A patent/FR2196987B1/fr not_active Expired
-
1974
- 1974-12-05 GB GB5255974A patent/GB1437898A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2196987B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-05-13 |
| US3862147A (en) | 1975-01-21 |
| CA1009661A (en) | 1977-05-03 |
| FR2196987A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-22 |
| GB1437898A (en) | 1976-06-03 |
| GB1436879A (en) | 1976-05-26 |
| JPS4956916A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-06-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69502076T2 (de) | Verfahren zur Gewinnung von leichten Wertprodukten aus den Destillationsrückständen der Verfahren zur Herstellung von Acrylsäure und ihren Estern | |
| DE2629769C3 (de) | Verfahren zur Herstellung von reinem Methyl-tertiär-butyläther | |
| DE60001592T2 (de) | Verfahren zur Reinigung von (Meth)acrylsäure | |
| DE69301579T2 (de) | Verbessertes Verfahren zur Gleichzeitigen Herstellung von Propylenoxid und Styrolmonomer | |
| DE3150755A1 (de) | "verfahren zur abtrennung von methanol aus den bei der veraetherung von c(pfeil abwaerts)4(pfeil abwaerts) bis c(pfeil abwaerts)7(pfeil abwaerts)-isoolefinen mit methanol anfallenden reaktionsprodukten" | |
| DE2136396A1 (de) | Verfahren zur gewinnung wasserfreier acrylsaeure | |
| DE3809417A1 (de) | Verfahren zur kontinuierlichen veresterung von fettsaeuren | |
| DD147664A5 (de) | Verfahren zur gleichzeitigen herstellung von reinem methyl-tert.-butylether | |
| EP0790230A1 (de) | Verfahren zur kontinuierlichen Herstellung von Alkylestern der (Meth)acrylsäure | |
| WO1999050220A1 (de) | Verfahren zur herstellung von acrylsäure und acrylsäureestern | |
| EP1068174A1 (de) | Verfahren zur herstellung von acrylsäure und acrylsäureestern | |
| DE10251328A1 (de) | Extraktionsverfahren zur Gewinnung von Acrylsäure | |
| DE2340929A1 (de) | Verfahren zur herstellung von maleinsaeureanhydrid | |
| DE69736436T2 (de) | Reinigung der durch katalytische propylenoxidation erhaltene acrylsäure | |
| DE2400260C3 (de) | Verfahren zur Abtrennung von Methacrolein aus einer Gasreaktionsmischung | |
| DE2331722A1 (de) | Verfahren zur reinigung von 1,3-dioxolan | |
| DE1223826B (de) | Verfahren zur Gewinnung von wasser- und weitgehend ameisensaeurefreier Essigsaeure | |
| DE19709471A1 (de) | Verfahren zur Herstellung von (Meth)acrylsäure | |
| DE3131981A1 (de) | Verfarhen zur aufarbeitung von rohem, fluessigem vinylacetat | |
| DE885542C (de) | Verfahren zur Herstellung von Acrylsaeuremethylester | |
| DE2110031A1 (de) | Verfahren zur Abtrennung von Methacrolein | |
| DE2641134A1 (de) | Verfahren zur reinigung von aethylenglycol oder propylenglycol | |
| DE10224341A1 (de) | Verfahren zur Herstellung von Acrylsäure und/oder deren Ester sowie von Propionsäure und/oder deren Ester im Verbund | |
| DE2330235B2 (de) | Verfahren zur Gewinnung von Carbonsäureestern aus den Abfallsalzlösungen der Cyclohexanonherstellung | |
| WO2003095411A1 (de) | Verfahren zur herstellung von acrylsäure und/ oder deren ester sowie von propionsäure und/ oder deren ester im verbund |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |