DE1148990B - Verfahren zur Herstellung von Carbonsaeuren aus Olefinen, Kohlenoxyd und Wasser - Google Patents
Verfahren zur Herstellung von Carbonsaeuren aus Olefinen, Kohlenoxyd und WasserInfo
- Publication number
- DE1148990B DE1148990B DEST14707A DEST014707A DE1148990B DE 1148990 B DE1148990 B DE 1148990B DE ST14707 A DEST14707 A DE ST14707A DE ST014707 A DEST014707 A DE ST014707A DE 1148990 B DE1148990 B DE 1148990B
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- water
- acid
- phosphoric acid
- acids
- 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
- 150000001336 alkenes Chemical class 0.000 title claims description 34
- 150000001735 carboxylic acids Chemical class 0.000 title claims description 32
- 238000000034 method Methods 0.000 title claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 31
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims description 17
- 229910002090 carbon oxide Inorganic materials 0.000 title claims description 7
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 64
- 239000003054 catalyst Substances 0.000 claims description 43
- 235000011007 phosphoric acid Nutrition 0.000 claims description 33
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 29
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 24
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- -1 cyclic olefins Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 238000000926 separation method Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 230000008021 deposition Effects 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 229940005657 pyrophosphoric acid Drugs 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 150000007513 acids Chemical class 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 11
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000010410 layer Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 208000001848 dysentery Diseases 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- ZOLLIQAKMYWTBR-MOLCZBCNSA-N (1z,5z,9z)-cyclododeca-1,5,9-triene Chemical compound C\1C\C=C/CC\C=C/CC\C=C/1 ZOLLIQAKMYWTBR-MOLCZBCNSA-N 0.000 description 1
- PRXPWGNCAMNYSN-UHFFFAOYSA-N 1,2,3,3a,4,5,5a,6,7,8,8a,8b-dodecahydroacenaphthylene-1-carboxylic acid Chemical class OC(=O)C1CC2CCCC3CCCC1C23 PRXPWGNCAMNYSN-UHFFFAOYSA-N 0.000 description 1
- MLYJAHYIPOXSRR-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalene-1-carboxylic acid Chemical compound C1CCCC2C(C(=O)O)CCCC21 MLYJAHYIPOXSRR-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 102100035593 POU domain, class 2, transcription factor 1 Human genes 0.000 description 1
- 101710084414 POU domain, class 2, transcription factor 1 Proteins 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- ZRYCZAWRXHAAPZ-UHFFFAOYSA-N alpha,alpha-dimethyl valeric acid Chemical compound CCCC(C)(C)C(O)=O ZRYCZAWRXHAAPZ-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- WFHKESPONQXPGD-UHFFFAOYSA-N epi-Khusinol Natural products CC(C)C1CCC(=C)C2C(O)CC(C)=CC12 WFHKESPONQXPGD-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000007704 transition Effects 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
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL108426D NL108426C (enExample) | 1959-01-26 | ||
| DEST14707A DE1148990B (de) | 1959-01-26 | 1959-01-26 | Verfahren zur Herstellung von Carbonsaeuren aus Olefinen, Kohlenoxyd und Wasser |
| GB113060A GB924297A (en) | 1959-01-26 | 1960-01-12 | Production of carboxylic acids from olefins, carbon monoxide and water |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEST14707A DE1148990B (de) | 1959-01-26 | 1959-01-26 | Verfahren zur Herstellung von Carbonsaeuren aus Olefinen, Kohlenoxyd und Wasser |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1148990B true DE1148990B (de) | 1963-05-22 |
Family
ID=7456436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEST14707A Pending DE1148990B (de) | 1959-01-26 | 1959-01-26 | Verfahren zur Herstellung von Carbonsaeuren aus Olefinen, Kohlenoxyd und Wasser |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1148990B (enExample) |
| GB (1) | GB924297A (enExample) |
| NL (1) | NL108426C (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020177733A1 (en) * | 2001-03-28 | 2002-11-28 | Ramzi Saleh | Manufacture of cyclic aliphatic acids and esters |
-
0
- NL NL108426D patent/NL108426C/xx active
-
1959
- 1959-01-26 DE DEST14707A patent/DE1148990B/de active Pending
-
1960
- 1960-01-12 GB GB113060A patent/GB924297A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB924297A (en) | 1963-04-24 |
| NL108426C (enExample) |
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