RU2297997C2 - Способ получения дикарбоновых кислот - Google Patents
Способ получения дикарбоновых кислот Download PDFInfo
- Publication number
- RU2297997C2 RU2297997C2 RU2004132831/04A RU2004132831A RU2297997C2 RU 2297997 C2 RU2297997 C2 RU 2297997C2 RU 2004132831/04 A RU2004132831/04 A RU 2004132831/04A RU 2004132831 A RU2004132831 A RU 2004132831A RU 2297997 C2 RU2297997 C2 RU 2297997C2
- Authority
- RU
- Russia
- Prior art keywords
- oxidation
- catalyst
- cyclohexane
- cyclohexyl hydroperoxide
- hydroperoxide
- Prior art date
Links
- 150000001991 dicarboxylic acids Chemical class 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title abstract description 8
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 60
- 230000003647 oxidation Effects 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 47
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 42
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000001301 oxygen Substances 0.000 claims abstract description 18
- 239000007789 gas Substances 0.000 claims abstract description 14
- 239000012429 reaction media Substances 0.000 claims abstract description 13
- 238000000926 separation method Methods 0.000 claims abstract description 8
- 239000007800 oxidant agent Substances 0.000 claims abstract description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 13
- 239000012074 organic phase Substances 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 150000002576 ketones Chemical class 0.000 claims description 9
- 239000008346 aqueous phase Substances 0.000 claims description 8
- 239000007791 liquid phase Substances 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
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- 238000011282 treatment Methods 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
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- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims description 2
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- 238000010908 decantation Methods 0.000 claims description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 2
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- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 239000011572 manganese Substances 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract description 50
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract description 3
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- 235000011037 adipic acid Nutrition 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 16
- 150000007513 acids Chemical class 0.000 description 14
- 150000001735 carboxylic acids Chemical class 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000004215 Carbon black (E152) Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 9
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- 238000004458 analytical method Methods 0.000 description 8
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- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 6
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- 239000007787 solid Substances 0.000 description 4
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- 125000000217 alkyl group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
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- 229910052735 hafnium Inorganic materials 0.000 description 3
- 239000002638 heterogeneous catalyst Substances 0.000 description 3
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- 239000000047 product Substances 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910052684 Cerium Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
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- 238000002474 experimental method Methods 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- 238000007210 heterogeneous catalysis Methods 0.000 description 2
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
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- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
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- UVWPNDVAQBNQBG-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-icosafluorononane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UVWPNDVAQBNQBG-UHFFFAOYSA-N 0.000 description 1
- USPWUOFNOTUBAD-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(trifluoromethyl)benzene Chemical compound FC1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F USPWUOFNOTUBAD-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical class CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- YWBMNCRJFZGXJY-UHFFFAOYSA-N 1-hydroperoxy-1,2,3,4-tetrahydronaphthalene Chemical compound C1=CC=C2C(OO)CCCC2=C1 YWBMNCRJFZGXJY-UHFFFAOYSA-N 0.000 description 1
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- ZDFKSZDMHJHQHS-UHFFFAOYSA-N 2-tert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC=CC=C1C(O)=O ZDFKSZDMHJHQHS-UHFFFAOYSA-N 0.000 description 1
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- 150000003624 transition metals Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical class CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical class CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/14—Adipic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/21—Dicarboxylic acids containing twelve carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0204332A FR2838122B1 (fr) | 2002-04-08 | 2002-04-08 | Procede de fabrication d'acides carboxyliques |
| FR0204332 | 2002-04-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2004132831A RU2004132831A (ru) | 2005-07-20 |
| RU2297997C2 true RU2297997C2 (ru) | 2007-04-27 |
Family
ID=28052180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004132831/04A RU2297997C2 (ru) | 2002-04-08 | 2003-03-28 | Способ получения дикарбоновых кислот |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP1492754B1 (enExample) |
| JP (1) | JP4434751B2 (enExample) |
| KR (1) | KR100641623B1 (enExample) |
| CN (1) | CN100341837C (enExample) |
| AT (1) | ATE413372T1 (enExample) |
| AU (1) | AU2003232303A1 (enExample) |
| BR (2) | BRPI0308954C8 (enExample) |
| DE (1) | DE60324536D1 (enExample) |
| ES (1) | ES2315520T3 (enExample) |
| FR (1) | FR2838122B1 (enExample) |
| RU (1) | RU2297997C2 (enExample) |
| TW (1) | TWI334863B (enExample) |
| UA (1) | UA77771C2 (enExample) |
| WO (1) | WO2003084913A2 (enExample) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU97120888A (ru) * | 1996-12-12 | 1999-10-27 | Рон-Пуленк Фибер э Резэн Энтермедиат | Способ получения дикислот из промывных вод продуктов окисления циклогексана |
| US6037491A (en) * | 1997-07-25 | 2000-03-14 | Rpc Inc. | Methods and devices for controlling hydrocarbon oxidations to respective acids by adjusting the solvent to hydrocarbon ratio |
| US6129875A (en) * | 1998-02-19 | 2000-10-10 | Rpc Inc. | Process of separating catalyst from oxidation mixtures |
| US6232495B1 (en) * | 1998-02-09 | 2001-05-15 | Rpc Inc. | Methods for treating cobalt catalyst in oxidation mixtures resulting from oxidation of hydrocarbons to dibasic acids |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE757061A (fr) * | 1969-10-06 | 1971-04-05 | Rhone Poulenc Sa | Procede d'obtention d'acide adipique |
| JPS52931B1 (enExample) * | 1970-06-27 | 1977-01-11 | ||
| GB9113343D0 (en) * | 1991-06-20 | 1991-08-07 | Shell Int Research | Catalytic oxidation of hydrocarbons |
| US5321157A (en) * | 1992-09-25 | 1994-06-14 | Redox Technologies Inc. | Process for the preparation of adipic acid and other aliphatic dibasic acids |
| DE69609940T4 (de) * | 1996-01-13 | 2002-05-29 | Council Of Scientific And Industrial Research, Neu Delhi | Verfahren zur Herstellung von Adipinsäure |
| FR2757154B1 (fr) * | 1996-12-12 | 2000-01-14 | Rhone Poulenc Fibres | Procede de preparation de diacides a partir des eaux de lavage des produits d'oxydation du cyclohexane |
| DE19941315A1 (de) * | 1999-08-31 | 2001-03-01 | Bayer Ag | Selektivoxidation von Kohlenwasserstoffen |
-
2002
- 2002-04-08 FR FR0204332A patent/FR2838122B1/fr not_active Expired - Fee Related
-
2003
- 2003-03-28 UA UA20041008177A patent/UA77771C2/uk unknown
- 2003-03-28 RU RU2004132831/04A patent/RU2297997C2/ru not_active IP Right Cessation
- 2003-03-28 DE DE60324536T patent/DE60324536D1/de not_active Expired - Lifetime
- 2003-03-28 ES ES03745809T patent/ES2315520T3/es not_active Expired - Lifetime
- 2003-03-28 CN CNB038099713A patent/CN100341837C/zh not_active Expired - Fee Related
- 2003-03-28 JP JP2003582112A patent/JP4434751B2/ja not_active Expired - Fee Related
- 2003-03-28 AU AU2003232303A patent/AU2003232303A1/en not_active Abandoned
- 2003-03-28 BR BRPI0308954D patent/BRPI0308954C8/pt unknown
- 2003-03-28 AT AT03745809T patent/ATE413372T1/de not_active IP Right Cessation
- 2003-03-28 EP EP03745809A patent/EP1492754B1/fr not_active Expired - Lifetime
- 2003-03-28 KR KR1020047016123A patent/KR100641623B1/ko not_active Expired - Fee Related
- 2003-03-28 BR BRPI0308954A patent/BRPI0308954B8/pt not_active IP Right Cessation
- 2003-03-28 WO PCT/FR2003/000984 patent/WO2003084913A2/fr not_active Ceased
- 2003-04-07 TW TW092107885A patent/TWI334863B/zh not_active IP Right Cessation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU97120888A (ru) * | 1996-12-12 | 1999-10-27 | Рон-Пуленк Фибер э Резэн Энтермедиат | Способ получения дикислот из промывных вод продуктов окисления циклогексана |
| US6037491A (en) * | 1997-07-25 | 2000-03-14 | Rpc Inc. | Methods and devices for controlling hydrocarbon oxidations to respective acids by adjusting the solvent to hydrocarbon ratio |
| US6232495B1 (en) * | 1998-02-09 | 2001-05-15 | Rpc Inc. | Methods for treating cobalt catalyst in oxidation mixtures resulting from oxidation of hydrocarbons to dibasic acids |
| US6326455B2 (en) * | 1998-02-09 | 2001-12-04 | Rpc Inc. | Methods for treating cobalt catalyst in oxidation mixtures resulting from oxidation of hydrocarbons to dibasic acids |
| US6129875A (en) * | 1998-02-19 | 2000-10-10 | Rpc Inc. | Process of separating catalyst from oxidation mixtures |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100341837C (zh) | 2007-10-10 |
| FR2838122B1 (fr) | 2004-05-21 |
| BRPI0308954B8 (pt) | 2016-10-11 |
| ES2315520T3 (es) | 2009-04-01 |
| RU2004132831A (ru) | 2005-07-20 |
| AU2003232303A1 (en) | 2003-10-20 |
| BRPI0308954C8 (pt) | 2017-03-21 |
| FR2838122A1 (fr) | 2003-10-10 |
| TWI334863B (en) | 2010-12-21 |
| JP4434751B2 (ja) | 2010-03-17 |
| EP1492754A2 (fr) | 2005-01-05 |
| DE60324536D1 (enExample) | 2008-12-18 |
| JP2005522474A (ja) | 2005-07-28 |
| KR100641623B1 (ko) | 2006-11-06 |
| UA77771C2 (en) | 2007-01-15 |
| AU2003232303A8 (en) | 2003-10-20 |
| WO2003084913A8 (fr) | 2004-06-10 |
| BR0308954B1 (pt) | 2013-11-19 |
| TW200306300A (en) | 2003-11-16 |
| EP1492754B1 (fr) | 2008-11-05 |
| WO2003084913A2 (fr) | 2003-10-16 |
| ATE413372T1 (de) | 2008-11-15 |
| KR20040111498A (ko) | 2004-12-31 |
| BR0308954A (pt) | 2005-01-04 |
| CN1649818A (zh) | 2005-08-03 |
| WO2003084913A3 (fr) | 2004-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20150329 |