CA1057766A - Anhydride separation process - Google Patents
Anhydride separation processInfo
- Publication number
- CA1057766A CA1057766A CA222,291A CA222291A CA1057766A CA 1057766 A CA1057766 A CA 1057766A CA 222291 A CA222291 A CA 222291A CA 1057766 A CA1057766 A CA 1057766A
- Authority
- CA
- Canada
- Prior art keywords
- absorbent
- anhydride
- maleic anhydride
- accordance
- absorber
- 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
- 150000008064 anhydrides Chemical class 0.000 title claims abstract description 35
- 238000000926 separation method Methods 0.000 title abstract description 8
- 239000002250 absorbent Substances 0.000 claims abstract description 76
- 230000002745 absorbent Effects 0.000 claims abstract description 76
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 38
- 239000006096 absorbing agent Substances 0.000 claims abstract description 34
- 238000010521 absorption reaction Methods 0.000 claims abstract description 26
- 239000008246 gaseous mixture Substances 0.000 claims abstract description 22
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 14
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000007788 liquid Substances 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 230000000694 effects Effects 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 22
- 230000003647 oxidation Effects 0.000 claims description 18
- 238000007254 oxidation reaction Methods 0.000 claims description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- JHNMPYMTHAMTJM-UHFFFAOYSA-N phenyl-(2,3,4,5-tetramethylphenyl)methanone Chemical class CC1=C(C)C(C)=CC(C(=O)C=2C=CC=CC=2)=C1C JHNMPYMTHAMTJM-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000007789 gas Substances 0.000 description 32
- 239000000047 product Substances 0.000 description 10
- 238000004821 distillation Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 269 2 Chemical class 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 229960002380 dibutyl phthalate Drugs 0.000 description 3
- 235000011087 fumaric acid Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910001868 water Inorganic materials 0.000 description 3
- ZSQCNVWYBBKUHS-UHFFFAOYSA-N (2,3-dimethylphenyl)-phenylmethanone Chemical compound CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1C ZSQCNVWYBBKUHS-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 239000002594 sorbent Substances 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- KTJWVFYKGHSIAS-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)propan-1-one Chemical class CCC(=O)C1=CC=CC(C)=C1C KTJWVFYKGHSIAS-UHFFFAOYSA-N 0.000 description 1
- GGMPTLAAIUQMIE-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobiphenyl Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=CC=CC=C1 GGMPTLAAIUQMIE-UHFFFAOYSA-N 0.000 description 1
- YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram 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
- 239000012530 fluid Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 150000002238 fumaric acids Chemical class 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- UKASIOIEWZDBIT-UHFFFAOYSA-N phenyl-(2,3,4-trimethylphenyl)methanone Chemical class CC1=C(C)C(C)=CC=C1C(=O)C1=CC=CC=C1 UKASIOIEWZDBIT-UHFFFAOYSA-N 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- 150000003071 polychlorinated biphenyls Polymers 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229940045605 vanadium Drugs 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C07C51/573—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Furan Compounds (AREA)
- Gas Separation By Absorption (AREA)
- Treating Waste Gases (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45248874A | 1974-03-18 | 1974-03-18 | |
| US55007075A | 1975-02-14 | 1975-02-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1057766A true CA1057766A (en) | 1979-07-03 |
Family
ID=27036787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA222,291A Expired CA1057766A (en) | 1974-03-18 | 1975-03-17 | Anhydride separation process |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5442962B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1057766A (enrdf_load_stackoverflow) |
| DE (1) | DE2510479C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2264812B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1443411A (enrdf_load_stackoverflow) |
| IT (1) | IT1034245B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1163975B (it) * | 1979-03-21 | 1987-04-08 | Ftalital Prod Chim Spec | Procedimento per separare in modo continuo anidride maleica da gas di processo |
| KR20140015418A (ko) | 2011-05-11 | 2014-02-06 | 헌츠만 페트로케미칼 엘엘씨 | 가스 스트림으로부터 말레산 무수물을 회수하기 위한 개량된 용매 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3850758A (en) * | 1973-07-02 | 1974-11-26 | Allied Chem | Purification of crude maleic anhydride by treatment with dimethylbenzophenone |
-
1975
- 1975-03-10 FR FR7507438A patent/FR2264812B1/fr not_active Expired
- 1975-03-11 DE DE19752510479 patent/DE2510479C3/de not_active Expired
- 1975-03-13 IT IT2122475A patent/IT1034245B/it active
- 1975-03-17 CA CA222,291A patent/CA1057766A/en not_active Expired
- 1975-03-18 JP JP3288375A patent/JPS5442962B2/ja not_active Expired
- 1975-03-18 GB GB1129475A patent/GB1443411A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2510479A1 (de) | 1975-09-25 |
| JPS5442962B2 (enrdf_load_stackoverflow) | 1979-12-17 |
| GB1443411A (en) | 1976-07-21 |
| DE2510479B2 (de) | 1979-01-18 |
| DE2510479C3 (de) | 1979-09-20 |
| JPS50131923A (enrdf_load_stackoverflow) | 1975-10-18 |
| FR2264812A1 (enrdf_load_stackoverflow) | 1975-10-17 |
| FR2264812B1 (enrdf_load_stackoverflow) | 1978-10-20 |
| IT1034245B (it) | 1979-09-10 |
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