CS228927B2 - Method of preparing fumaric acid - Google Patents

Method of preparing fumaric acid Download PDF

Info

Publication number: CS228927B2
Authority: CS; Czechoslovakia
Prior art keywords: fumaric acid; maleic acid; hours; phase; isomerization
Prior art date: 1981-05-18

Application number

CS823602A

Other languages

Czech (cs)

English (en)

Inventor

Francesco Benedetti

Ezio Polacco

Angelo Celli

Original Assignee

Italiana Carbochimica

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.)

1981-05-18

Filing date

1982-05-17

Publication date

1984-05-14

1982-05-17 Application filed by Italiana Carbochimica filed Critical Italiana Carbochimica

1984-05-14 Publication of CS228927B2 publication Critical patent/CS228927B2/cs

Links

VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 title claims abstract description 55
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 title claims abstract description 45
239000001530 fumaric acid Substances 0.000 title claims abstract description 27
238000000034 method Methods 0.000 title claims abstract description 22
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 18
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 18
239000011976 maleic acid Substances 0.000 claims abstract description 18
238000006317 isomerization reaction Methods 0.000 claims abstract description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
230000003647 oxidation Effects 0.000 claims abstract description 7
238000007254 oxidation reaction Methods 0.000 claims abstract description 7
229930195733 hydrocarbon Natural products 0.000 claims abstract description 5
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 5
239000003643 water by type Substances 0.000 claims abstract description 4
238000010438 heat treatment Methods 0.000 claims description 17
239000000047 product Substances 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 11
239000013078 crystal Substances 0.000 claims description 8
238000005406 washing Methods 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 5
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
239000002912 waste gas Substances 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
239000000706 filtrate Substances 0.000 claims description 2
238000001914 filtration Methods 0.000 abstract description 13
238000002425 crystallisation Methods 0.000 abstract description 9
230000008025 crystallization Effects 0.000 abstract description 9
239000012535 impurity Substances 0.000 abstract description 8
238000001035 drying Methods 0.000 abstract description 6
238000004090 dissolution Methods 0.000 abstract description 4
239000004215 Carbon black (E152) Substances 0.000 abstract description 3
239000012467 final product Substances 0.000 abstract description 3
230000008030 elimination Effects 0.000 abstract description 2
238000003379 elimination reaction Methods 0.000 abstract description 2
239000007789 gas Substances 0.000 abstract description 2
238000004042 decolorization Methods 0.000 abstract 1
238000001953 recrystallisation Methods 0.000 abstract 1
238000009997 thermal pre-treatment Methods 0.000 abstract 1
230000009466 transformation Effects 0.000 abstract 1
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
238000000926 separation method Methods 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
238000010586 diagram Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
238000007605 air drying Methods 0.000 description 3
235000010233 benzoic acid Nutrition 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229940078552 o-xylene Drugs 0.000 description 3
238000011085 pressure filtration Methods 0.000 description 3
FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
239000003245 coal Substances 0.000 description 2
238000002485 combustion reaction Methods 0.000 description 2
238000002845 discoloration Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000009776 industrial production Methods 0.000 description 2
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
229930192627 Naphthoquinone Natural products 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
239000001273 butane Substances 0.000 description 1
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
229940018557 citraconic acid Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000003226 decolorizating effect Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
238000012432 intermediate storage Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
150000002791 naphthoquinones Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
238000012856 packing Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000004053 quinones Chemical class 0.000 description 1
239000002994 raw material Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000005201 scrubbing Methods 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
239000002351 wastewater Substances 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
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton

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)
Treating Waste Gases (AREA)

CS823602A 1981-05-18 1982-05-17 Method of preparing fumaric acid CS228927B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT21766/81A IT1167537B (it)	1981-05-18	1981-05-18	Procedimento per la produzione di acido fumarico partendo da acque di lavaggio di gas esausti provenienti da ossidazione di idrocarburi

Publications (1)

Publication Number	Publication Date
CS228927B2 true CS228927B2 (en)	1984-05-14

Family

ID=11186557

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS823602A CS228927B2 (en)	1981-05-18	1982-05-17	Method of preparing fumaric acid

Country Status (12)

Country	Link
JP (1)	JPS5823641A (fr)
AU (1)	AU8380482A (fr)
BE (1)	BE893184A (fr)
BR (1)	BR8202862A (fr)
CS (1)	CS228927B2 (fr)
DE (1)	DE3213142A1 (fr)
FR (1)	FR2505822B1 (fr)
GB (1)	GB2098612B (fr)
HU (1)	HU188168B (fr)
IT (1)	IT1167537B (fr)
YU (1)	YU103882A (fr)
ZA (1)	ZA823068B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5929255A (en) *	1996-07-11	1999-07-27	Bp Amoco Corporation	Process for coproducing fumaric acid and maleic anhydride

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1321416A (fr) *	1961-06-16	1963-03-22	Scient Design Co	Procédé de préparation d'acide maléique de grande pureté

1981
- 1981-05-18 IT IT21766/81A patent/IT1167537B/it active
1982
- 1982-04-08 DE DE19823213142 patent/DE3213142A1/de not_active Withdrawn
- 1982-05-04 ZA ZA823068A patent/ZA823068B/xx unknown
- 1982-05-14 BE BE0/208088A patent/BE893184A/fr not_active IP Right Cessation
- 1982-05-14 FR FR8208461A patent/FR2505822B1/fr not_active Expired
- 1982-05-14 GB GB8214088A patent/GB2098612B/en not_active Expired
- 1982-05-17 YU YU01038/82A patent/YU103882A/xx unknown
- 1982-05-17 BR BR8202862A patent/BR8202862A/pt unknown
- 1982-05-17 CS CS823602A patent/CS228927B2/cs unknown
- 1982-05-17 HU HU821555A patent/HU188168B/hu unknown
- 1982-05-18 JP JP57084683A patent/JPS5823641A/ja active Pending
- 1982-05-18 AU AU83804/82A patent/AU8380482A/en not_active Abandoned

Also Published As

Publication number	Publication date
GB2098612A (en)	1982-11-24
FR2505822A1 (fr)	1982-11-19
ZA823068B (en)	1983-03-30
AU8380482A (en)	1982-11-25
BR8202862A (pt)	1983-04-26
FR2505822B1 (fr)	1985-09-06
GB2098612B (en)	1985-07-10
BE893184A (fr)	1982-08-30
DE3213142A1 (de)	1982-12-09
JPS5823641A (ja)	1983-02-12
IT8121766A0 (it)	1981-05-18
IT1167537B (it)	1987-05-13
HU188168B (en)	1986-03-28
YU103882A (en)	1985-04-30

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