CA1131248A - Methode de preparation d'acides organiques - Google Patents

Methode de preparation d'acides organiques

Info

Publication number: CA1131248A
Authority: CA; Canada
Prior art keywords: acetone; water; mixture; insoluble; soluble
Prior art date: 1979-09-26
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

Application number

CA336,394A

Other languages

English (en)

Inventor

Edward T. Sabourin

Johann G.D. Schulz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Gulf Research and Development Co

Original Assignee

Gulf Research and Development Co

Priority date (The priority date 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 date listed.)

1979-09-26

Filing date

1979-09-26

Publication date

1982-09-07

1979-09-26 Application filed by Gulf Research and Development Co filed Critical Gulf Research and Development Co

1979-09-26 Priority to CA336,394A priority Critical patent/CA1131248A/fr

1982-09-07 Application granted granted Critical

1982-09-07 Publication of CA1131248A publication Critical patent/CA1131248A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 7
150000007524 organic acids Chemical class 0.000 title abstract description 5
235000005985 organic acids Nutrition 0.000 title abstract description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 64
239000000203 mixture Substances 0.000 claims abstract description 29
239000002253 acid Substances 0.000 claims abstract description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 23
150000007513 acids Chemical class 0.000 claims abstract description 23
229910017604 nitric acid Inorganic materials 0.000 claims abstract description 23
239000007787 solid Substances 0.000 claims abstract description 20
238000006243 chemical reaction Methods 0.000 claims abstract description 18
239000002002 slurry Substances 0.000 claims abstract description 13
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 11
229910001882 dioxygen Inorganic materials 0.000 claims abstract description 11
239000002798 polar solvent Substances 0.000 claims abstract description 11
239000003245 coal Substances 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims description 13
238000000926 separation method Methods 0.000 claims description 6
239000003077 lignite Substances 0.000 claims description 3
238000001035 drying Methods 0.000 claims 1
238000001914 filtration Methods 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000003575 carbonaceous material Substances 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
229960003903 oxygen Drugs 0.000 description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
239000011593 sulfur Substances 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
229910052753 mercury Inorganic materials 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000000243 solution Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000000463 material Substances 0.000 description 3
MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001491 aromatic compounds Chemical class 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
229910010272 inorganic material Inorganic materials 0.000 description 2
239000011147 inorganic material Substances 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000002904 solvent Substances 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000036366 Sensation of pressure Diseases 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000002802 bituminous coal Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
230000000875 corresponding effect Effects 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
125000003367 polycyclic group Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000003476 subbituminous coal Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA336,394A 1979-09-26 1979-09-26 Methode de preparation d'acides organiques Expired CA1131248A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA336,394A CA1131248A (fr)	1979-09-26	1979-09-26	Methode de preparation d'acides organiques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA336,394A CA1131248A (fr)	1979-09-26	1979-09-26	Methode de preparation d'acides organiques

Publications (1)

Publication Number	Publication Date
CA1131248A true CA1131248A (fr)	1982-09-07

Family

ID=4115223

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA336,394A Expired CA1131248A (fr)	1979-09-26	1979-09-26	Methode de preparation d'acides organiques

Country Status (1)

Country	Link
CA (1)	CA1131248A (fr)

1979
- 1979-09-26 CA CA336,394A patent/CA1131248A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-09-07	MKEX	Expiry

Publication	Publication Date	Title
US4052448A (en)	1977-10-04	Organic acids and process for preparing same
CA1111624A (fr)	1981-11-03	Procede d'obtention industrielle d'hydroxyde d'aluminium grossier
CA1149303A (fr)	1983-07-05	Traitement de la houille
CA1207751A (fr)	1986-07-15	Traitement des humus
US3998756A (en)	1976-12-21	Preparation of activated carbonaceous material from sewage sludge and sulfuric acid
US4239613A (en)	1980-12-16	Deashed coal from nitric acid oxidation of aqueous coal slurry
US4640761A (en)	1987-02-03	Process for preparing pitch
CA1131248A (fr)	1982-09-07	Methode de preparation d'acides organiques
US4195186A (en)	1980-03-25	Process for preparing organic acids
US4195185A (en)	1980-03-25	Process of preparing organic acids
EP0026244B1 (fr)	1983-10-19	Préparation d'un mélange d'acides polycarboxyliques aromatiques polycycliques, soluble dans l'acétone mais insoluble dans l'eau
US2809938A (en)	1957-10-15	Activatable chars, activated carbons, and process for preparing the same
US4150040A (en)	1979-04-17	Aromatic anhydrides
EP0026245B1 (fr)	1984-05-16	Préparation d'un mélange d'acides aromatiques polycycliques et polycarboxyliques, soluble dans l'acétone et dans l'eau, et mélange ainsi obtenu
US4334084A (en)	1982-06-08	Organic acids and process for preparing same
US4382146A (en)	1983-05-03	Organic acids and process for preparing same
Brockman	1955	The preparation of dicyanodiacetylene
CA1140588A (fr)	1983-02-01	Methode de preparation d'acides organiques
CA1078774A (fr)	1980-06-03	Methode de fabrication d'une matiere charbonneuse
US4011254A (en)	1977-03-08	Process for the purification of diaminomaleonitrile
US4384134A (en)	1983-05-17	Process for preparing organic acids
GB1563451A (en)	1980-03-26	Nitro-substituted polyaromatic polycarboxylic acid compositions and processes for their preparation from coal based materials
JPS5822070B2 (ja)	1983-05-06	石炭系重質油の精製方法
SU997441A1 (ru)	1983-10-23	Способ получени жидкого топлива
EP0156051B1 (fr)	1987-06-10	Procédé pour la production de charbon en forme de poudre