CS195860B1 - Process for preparing propionic and/or succinic acid - Google Patents
Process for preparing propionic and/or succinic acid Download PDFInfo
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- CS195860B1 CS195860B1 CS141476A CS141476A CS195860B1 CS 195860 B1 CS195860 B1 CS 195860B1 CS 141476 A CS141476 A CS 141476A CS 141476 A CS141476 A CS 141476A CS 195860 B1 CS195860 B1 CS 195860B1
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- Prior art keywords
- succinic acid
- hydrogen
- acid
- propionic acid
- propionic
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 title claims description 44
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 title claims description 26
- 235000019260 propionic acid Nutrition 0.000 title claims description 22
- 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 title claims description 22
- 239000001384 succinic acid Substances 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000003054 catalyst Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 238000004508 fractional distillation Methods 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000012907 honey Nutrition 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- KSBBJJYULNAYMC-UHFFFAOYSA-N [Rh].[In] Chemical class [Rh].[In] KSBBJJYULNAYMC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Predmetom vynálezu je sposob výroby kyseliny propiónovej a/alebo jantárovej hydrogenáciou kyseliny maleínovej alebo jej funkčných derivátov na hydrogenačných katalyzátoroch.The present invention provides a process for the production of propionic acid and / or succinic acid by hydrogenating maleic acid or its functional derivatives on hydrogenation catalysts.
Kyselina propiónová sa vyrába priamo, připadne sa izoluje z reakČných produktov viacerých syntéz, kde je vedíajším produktom.Propionic acid is produced directly, or is isolated from the reaction products of several syntheses, where it is a by-product.
Jeden zo známých spósobov výroby kyseliny propiónovej je oxidácia uhlovodíkov. Tu sa získává popři kyselme octovej ako hlavnom produkte, spolu s dalšími vedlejšími produktami, hlavně estermi a ketónmi (Kliniec J., Nowicki B., Nosek J.: Chemik 1975, 213). Ako surovina sa používajú uhlovodíky C3 až Ce, ktoré sa oxidujú pri tlakuOne known method for producing propionic acid is the oxidation of hydrocarbons. It is obtained here along with acetic acid as the main product, along with other by-products, mainly esters and ketones (Kliniec J., Nowicki B., Nosek J .: Chemik 1975, 213). The hydrocarbons C3 to Ce, which are oxidized under pressure, are used as feedstock
3,5 až 7,0 MPa, pri teplote 160 až 200 °C. Produkty obsahujú do 10 % kyseliny propiónovej a mravčej. Keď sa vychádza pri oxidácii z naftových frakcií, pri 200 °C a 5,0 MPa sa získá produkt, ktorý obsahuje 10 % kyseliny propiónovej [Schwerdtel W.: Hydrocarbon Processing 118 (1970)]. V deliacom stupni tohto procesu sa používá 13 destilačných kolón. Hlavným produktom je kyselina propiónová pri syntéze z etylénu hydroformyláciou, kde sa však v prvom stupni získá propiónaldehyd, ktorý sa oxiduje v ďalšej části na kyselinu propiónovú (jap.3.5 to 7.0 MPa, at a temperature of 160 to 200 ° C. The products contain up to 10% propionic acid and formic acid. Starting from the naphtha fraction of oxidation, a product containing 10% propionic acid is obtained at 200 ° C and 50 bar (Schwerdtel W .: Hydrocarbon Processing 118 (1970)). In the separation step of this process, 13 distillation columns are used. The main product is propionic acid in the synthesis from ethylene by hydroformylation; however, in the first step, propionaldehyde is obtained, which is oxidized in the next step to propionic acid (jap.
pat. 1386 [1973J). Pri hydroformylácii etylénu sa používajú tlaky okolo 20,0 MPa (200 atm). Karbonylácia etylénu sa móže prevádzať aj za přítomnosti karbonylov niklu (NSR pat. 2 133 349) pri teplote 285°C. Ako katalyzátory možno použit aj komplexy ródia a india (NSR pat. 2 310 808), pričom sa pracuje pri teplote 195 °C a tlaku okolo 5,0 MPa.U.S. Pat. 1386 [1973]. Pressures of about 200 atm are used for ethylene hydroformylation. The carbonylation of ethylene can also be carried out in the presence of nickel carbonyl (NSR Pat. 2,133,349) at 285 ° C. Rhodium-indium complexes (NS Pat. No. 2,310,808) can also be used as catalysts at a temperature of 195 ° C and a pressure of about 5 bar.
Uvedené spósoby přípravy kyseliny propiónovej majú určité nevýhody v tom, že oxidáciou uhlovodíkov sa obyčajne připraví zmes organických kyslíkatých látok, ktorá sa ťažko dělí pre blízké body varu zložiek. Iné spósoby přípravy kyseliny propiónovej sú selektívne/ pracuje sa však pri vysokých tlakoch, náročnou a zložitou technológiou a spravidla viacstupňovou technológiou.The above processes for the preparation of propionic acid have some disadvantages in that the oxidation of hydrocarbons usually produces a mixture of organic oxygen species which is difficult to separate for near boiling points of the components. Other methods for the preparation of propionic acid are selective / however, they are operated at high pressures, demanding and complex technology, and generally multi-stage technology.
Podía tohto vynálezu sa spósob výroby kyseliny propiónovej a/alebo maleínovej a/ /alebo jej funkčných derivátov, s výhodou z maleínanhydridu, ako východiskových surovin uskutocňuje tak, že sa východiskové suroviny hydrogenujú v prúde vodíku alebo plynu obsahujúceho vodík, pri teplote 100 až 330 °C, s výhodou 180 až 280 °C, na hydrogenačných katalyzátoroch, pri objemovej rýchlosti od 90 do 450 h_1, pričom molárny poměr vodíka k privádzanej východiskové] surovině je od 5:1 do· 50 : 1 a zo vzniknu195860 tého reakčného produktu sa známým spósobom, s výhodou frakčnou destilácíou, oddělí kyselina propiónová a/alebo jantarová.According to the present invention, the process for producing propionic acid and / or maleic acid and / or functional derivatives thereof, preferably maleic anhydride, as starting materials is carried out by starting the raw materials in a stream of hydrogen or hydrogen-containing gas at a temperature of 100 to 330 ° C, preferably 180-280 ° C, on hydrogenation catalysts at a space velocity of from 90 to 450 h _1, wherein the molar ratio of hydrogen to the supplied starting] raw material is from 5: 1 to · 50: 1 and from vzniknu195860 th reaction product in a known manner, preferably by fractional distillation, separates propionic acid and / or succinic acid.
Východiskovou surovinou pri postupe podlá tohto vynálezu može byť kyselina maleínová alebo jej deriváty, a to najma maleínanhydrid a estery kyseliny maleínovej. Ako hydrogenačné katalyzátory sa osvědčili najma katalyzátory vhodné pre hydrogenáciu karhonylových skupin v molekule. Takými sú napr.: Cu na kremeline, NiO na kremeline, katalyzátor typu Cu—Zn—Cr, Raney med a pod. Vhodným rozpúšťadlom východiskových surovin je χ-butyrolaktón.The starting material in the process of the invention may be maleic acid or derivatives thereof, in particular maleic anhydride and maleic acid esters. In particular, catalysts suitable for the hydrogenation of carboxyl groups in a molecule have proved to be suitable as hydrogenation catalysts. These are, for example: Cu on silica, NiO on silica, Cu-Zn-Cr catalyst, Raney honey and the like. A suitable solvent for the starting materials is χ-butyrolactone.
Kyselina propiónová je významný výrobok pre polnohospodárstvo a medziprodukt róznych syntéz v chemickom priemysle. Výhodou postupu podlá tohto vynálezu je maximálně využitie východiskových surovin pri aplikácií hydrogenačných katalyzátorov.Propionic acid is an important product for agriculture and the intermediate product of various syntheses in the chemical industry. The advantage of the process according to the invention is the maximum utilization of the starting materials in the application of hydrogenation catalysts.
Příklad 1Example 1
Konštantná hydrogenačná aparatúra (reaktor o priemere 25 mm) sa naplní 100 ml katalyzátore (48 % Cu na kremeline). Katalyzátor sa před zavedením nástreku suroviny najskór zalhrieva 1 hodinu v prúde dusíka (100 Ni. lkat._1. h”1)- a redukuje dusíkovodíkovou zmesou pri 100 až 300 °C po dobu 6 hodin, pričom sa obsah vodíka v zmesi postupné zvyšuje, obsah dusíka znižuje. Nad náplň katalyzátore sa vloží inertná náplň. Do systému po vyhriatí v prúde vodíka pri 220 °C sa nastrekuje maleínanhydrid rozpuštěný v χ-butyrolaktóne (1:1) tak, aby sa dosiahlo zataženie maleínanhydridu 0,92 mól. lkal _1 . h_1 a objemová rýchlosť 20,7 h'1. Vodík sa prepúšťa v molárnom nadbytku k maleínanhydridu 30 : 1. Reakčný produkt pozostávajúci z pár reakčného produktu sa schladí, pričom skondenzuje kvapalný podiel. V produkte sa získá kyselina propiónová vo výťažku 20,7 % hmotnostných, χ-butyrolaktónu 22,9 % hmotnostných, kyselina jantárová 41,6 % hmotnostných. Z reakčného produktu sa destilačne vyizoluje kyselina propiónová a χ-butyrolaktón, V destilačnom zvyšku sa získá kyselina jantárová.A constant hydrogenation apparatus (25 mm diameter reactor) was charged with 100 mL of catalyst (48% Cu on silica). The catalyst prior to introducing the feed raw material is first zalhrieva 1 hour in flowing nitrogen (100 l. L cat. _1. H "1) - and reduces hydrazoic mixture at 100-300 ° C for 6 hours while hydrogen content in the mixture gradually increased , reduces the nitrogen content. An inert charge is placed over the catalyst bed. After heating in a stream of hydrogen at 220 ° C, the maleic anhydride dissolved in χ-butyrolactone (1: 1) is injected to obtain a loading of maleic anhydride of 0.92 mol. l kal _1 . h 1 and a space velocity of 20.7 hr 'first Hydrogen is passed in a molar excess to 30: 1 maleic anhydride. The reaction product consisting of the reaction product vapor is cooled while condensing the liquid portion. In the product, propionic acid is obtained in a yield of 20.7% by weight, χ-butyrolactone 22.9% by weight, succinic acid 41.6% by weight. Propionic acid and χ-butyrolactone are isolated by distillation from the reaction product. Succinic acid is obtained in the distillation residue.
Příklad 2Example 2
Použijú sa podmienky ako v příklade 1 s tým rozdielom, že sa pracuje pri teplote 240 °C a molárnom pomere vodík : maleínanhydridu 15:1. Získá sa výťažok kyseliny propiónovej 24,3 %, χ-butyrolaktónu 32,3 % a kyseliny jantárovej 26,1 %. Reakčný produkt ešte obsahoval malé množstvo n-butanolu, n-propanolu, kyseliny maslovej a vody.The conditions as in Example 1 were used except that the temperature was 240 ° C and the molar ratio of hydrogen: maleic anhydride was 15: 1. Yields of propionic acid 24.3%, χ-butyrolactone 32.3% and succinic acid 26.1% are obtained. The reaction product still contained small amounts of n-butanol, n-propanol, butyric acid and water.
Příklad 3Example 3
Pracuje sa obdobným postupom ako je popísané v příklade 1. Teplota 260 °C, molárny poměr vodík : maleínanhydridu 20 : 1. Kyselina prop?iónová sa získá vo výťažku 26,0 percent, χ-butyrolaktón 42,8 %, kyselina jantárová 14,1 %.The procedure is similar to that described in Example 1. Temperature 260 ° C, 20: 1 hydrogen: maleic anhydride molar ratio. Propionic acid is obtained in a yield of 26.0 percent, χ-butyrolactone 42.8%, succinic acid 14, 1%.
Příklad 4Example 4
Pracuje sa na obdobnoiu zariadení ako je popísané v příklade 1. Ako^ katalyzátor sa použije NiO/SiOz a hydrogenuje sa maleínanhydrid rozpuštěný v χ-butyrolaktóne (50 % rozbor). Pri teplote 280 °C a zatažení katalyzátore 1 mól. lkat.-1 · h_1 sa získá produkt s obsahom 11 % kyseliny propiónovej, 65 % χ-butyrolaktónu a 12 '% kyseliny jantárovej. P :· í k 1 a d 5.......... ........Work is carried out in a similar manner to that described in Example 1. NiO / SiO 2 is used as the catalyst and the maleic anhydride dissolved in β-butyrolactone is hydrogenated (50% assay). At a temperature of 280 ° C and a catalyst loading of 1 mol. l cat . -1 · h _1 product was obtained containing 11% propionic acid, 65% of χ-butyrolactone and 12 '% succinic acid. P: · k 1 ad 5 .......... ........
Do trubkového prietočného reaktora naplněného katalyzátorom Cu—Zn—Cr typu, ktorý sa aktivuje v prúde vodíka pri 100 až 280 °C po dobu 7 hodin, sa nastrekuje monobutylester kyseliny maleínovej rýchlosťou 0,9 mól. lkat._1. ih_1 pri teplote reaktora 300 °C. Reakčný produkt sa kondenzuje a analyzuje. Obsahuje 17,3 % kyseliny propiónovej, 38,6 % χ-butyrolaktónu a 14,6 % kyseliny jantárovej. Z reakčného produktu sa vyizoluje kyselina jantárová o obsahu čistej látky 93,5 % hmotnostných.A monobutyric acid ester was injected at a rate of 0.9 mol into a tubular flow reactor filled with a Cu-Zn-Cr catalyst of the type which was activated in a stream of hydrogen at 100 to 280 ° C for 7 hours. l ka t. _1 . 1 at a reactor temperature of 300 ° C. The reaction product was condensed and analyzed. It contains 17.3% propionic acid, 38.6% χ-butyrolactone and 14.6% succinic acid. Succinic acid having a pure content of 93.5% by weight is isolated from the reaction product.
P r í k 1 a d 6Example 6
Postupuje sa podlá příkladu 1 s tým, že sa použije Raney med ako katalyzátor. Do reaktora sa nastrekuje maleínanhydrid rozpuštěný v χ-butyrollaktóne (60 % rozbor). Pri teplote na katalyzátore 255 °C sa získá reakčná zmes o obsahu 14,8 % 'kyseliny propiónovej, 43,8 % χ-butyrolaktónu a 22,5 % kyseliny jantárovej.The procedure of Example 1 was followed using Raney honey as the catalyst. Maleic anhydride dissolved in χ-butyrollactone (60% assay) was injected into the reactor. At a catalyst temperature of 255 ° C, a reaction mixture of 14.8% propionic acid, 43.8% β-butyrolactone and 22.5% succinic acid was obtained.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS141476A CS195860B1 (en) | 1976-03-04 | 1976-03-04 | Process for preparing propionic and/or succinic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS141476A CS195860B1 (en) | 1976-03-04 | 1976-03-04 | Process for preparing propionic and/or succinic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195860B1 true CS195860B1 (en) | 1980-02-29 |
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ID=5348443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS141476A CS195860B1 (en) | 1976-03-04 | 1976-03-04 | Process for preparing propionic and/or succinic acid |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS195860B1 (en) |
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1976
- 1976-03-04 CS CS141476A patent/CS195860B1/en unknown
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