DE2007456A1 - Herstellung und Isolierung niederer aliphatiseher Säuren - Google Patents
Herstellung und Isolierung niederer aliphatiseher SäurenInfo
- Publication number
- DE2007456A1 DE2007456A1 DE19702007456 DE2007456A DE2007456A1 DE 2007456 A1 DE2007456 A1 DE 2007456A1 DE 19702007456 DE19702007456 DE 19702007456 DE 2007456 A DE2007456 A DE 2007456A DE 2007456 A1 DE2007456 A1 DE 2007456A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- acid
- water
- olefin
- mixture
- 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
- 125000001931 aliphatic group Chemical group 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 238000002955 isolation Methods 0.000 title claims description 7
- 239000003054 catalyst Substances 0.000 claims description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 26
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 23
- 238000004821 distillation Methods 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 16
- -1 aliphatic olefin Chemical class 0.000 claims description 13
- 239000011435 rock Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 46
- 239000000203 mixture Substances 0.000 description 43
- 239000000047 product Substances 0.000 description 40
- 150000001336 alkenes Chemical class 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 23
- 238000006277 sulfonation reaction Methods 0.000 description 18
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 16
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 13
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 13
- 150000001735 carboxylic acids Chemical class 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 238000010924 continuous production Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 241000158147 Sator Species 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- CLHYKAZPWIRRRD-UHFFFAOYSA-N 1-hydroxypropane-1-sulfonic acid Chemical compound CCC(O)S(O)(=O)=O CLHYKAZPWIRRRD-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000004028 organic sulfates Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- 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
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80025069A | 1969-02-18 | 1969-02-18 | |
| US80028969A | 1969-02-18 | 1969-02-18 | |
| ZA712189A ZA712189B (en) | 1969-02-18 | 1971-04-05 | Production and separation of lower aliphatic acids |
| FR7114809A FR2135729A5 (en) | 1969-02-18 | 1971-04-26 | Lower aliphatic acids - prepd and separated by a process allowing recycling of catalyst |
| BE766340A BE766340A (fr) | 1969-02-18 | 1971-04-27 | Procede perfectionne pour la synthese et l'isolement des acidesaliphatiques inferieurs. |
| NL7105799A NL7105799A (enrdf_load_stackoverflow) | 1969-02-18 | 1971-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2007456A1 true DE2007456A1 (de) | 1970-09-10 |
Family
ID=27543128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702007456 Pending DE2007456A1 (de) | 1969-02-18 | 1970-02-18 | Herstellung und Isolierung niederer aliphatiseher Säuren |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE766340A (enrdf_load_stackoverflow) |
| DE (1) | DE2007456A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2135729A5 (enrdf_load_stackoverflow) |
| NL (1) | NL7105799A (enrdf_load_stackoverflow) |
| ZA (1) | ZA712189B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4306101A (en) * | 1980-11-05 | 1981-12-15 | Shell Oil Company | Olefin hydration process |
| CA1223541A (en) * | 1985-01-09 | 1987-06-30 | Lawrence S. Kirch | Process for separating sulfuric acid and carboxylic acids |
-
1970
- 1970-02-18 DE DE19702007456 patent/DE2007456A1/de active Pending
-
1971
- 1971-04-05 ZA ZA712189A patent/ZA712189B/xx unknown
- 1971-04-26 FR FR7114809A patent/FR2135729A5/fr not_active Expired
- 1971-04-27 BE BE766340A patent/BE766340A/xx unknown
- 1971-04-28 NL NL7105799A patent/NL7105799A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7105799A (enrdf_load_stackoverflow) | 1972-10-31 |
| ZA712189B (en) | 1971-12-29 |
| FR2135729A5 (en) | 1972-12-22 |
| BE766340A (fr) | 1971-10-27 |
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