NO119081B - - Google Patents
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- Publication number
- NO119081B NO119081B NO15067263A NO15067263A NO119081B NO 119081 B NO119081 B NO 119081B NO 15067263 A NO15067263 A NO 15067263A NO 15067263 A NO15067263 A NO 15067263A NO 119081 B NO119081 B NO 119081B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- solvent
- water
- phase
- adipic acid
- Prior art date
Links
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 122
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 83
- 239000002904 solvent Substances 0.000 claims description 65
- 239000001361 adipic acid Substances 0.000 claims description 60
- 235000011037 adipic acid Nutrition 0.000 claims description 60
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 52
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 43
- 150000007513 acids Chemical class 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 239000001384 succinic acid Substances 0.000 claims description 34
- 239000012071 phase Substances 0.000 claims description 28
- 238000000926 separation method Methods 0.000 claims description 16
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 238000011084 recovery Methods 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims 1
- -1 cyclic alcohols Chemical class 0.000 description 14
- 230000003647 oxidation Effects 0.000 description 13
- 238000007254 oxidation reaction Methods 0.000 description 13
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 12
- 229910017604 nitric acid Inorganic materials 0.000 description 12
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 9
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 8
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 8
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 7
- 239000012452 mother liquor Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- ALVGHPMGQNBJRC-UHFFFAOYSA-N pentadecan-2-ol Chemical compound CCCCCCCCCCCCCC(C)O ALVGHPMGQNBJRC-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 5
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 238000001640 fractional crystallisation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ULIJUDULYQTGKI-UHFFFAOYSA-N 6-decoxy-6-oxohexanoic acid Chemical compound CCCCCCCCCCOC(=O)CCCCC(O)=O ULIJUDULYQTGKI-UHFFFAOYSA-N 0.000 description 3
- DYDCJEMYLPOPBS-UHFFFAOYSA-N 6-methylheptyl pentanoate Chemical compound CCCCC(=O)OCCCCCC(C)C DYDCJEMYLPOPBS-UHFFFAOYSA-N 0.000 description 3
- KDUGNDDZXPJVCS-UHFFFAOYSA-N 6-oxo-6-tridecoxyhexanoic acid Chemical compound CCCCCCCCCCCCCOC(=O)CCCCC(O)=O KDUGNDDZXPJVCS-UHFFFAOYSA-N 0.000 description 3
- LKSWDKHFKYWPAU-UHFFFAOYSA-N CCCCCCCCCCOC(=O)CCCC(O)=O Chemical compound CCCCCCCCCCOC(=O)CCCC(O)=O LKSWDKHFKYWPAU-UHFFFAOYSA-N 0.000 description 3
- RXTNIJMLAQNTEG-UHFFFAOYSA-N hexan-2-yl acetate Chemical compound CCCCC(C)OC(C)=O RXTNIJMLAQNTEG-UHFFFAOYSA-N 0.000 description 3
- XAPCMTMQBXLDBB-UHFFFAOYSA-N hexyl butyrate Chemical compound CCCCCCOC(=O)CCC XAPCMTMQBXLDBB-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Chemical class 0.000 description 3
- 239000011707 mineral Chemical class 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- ZJVMHPVIAUKERS-UHFFFAOYSA-N 2-hexylbutanedioic acid Chemical compound CCCCCCC(C(O)=O)CC(O)=O ZJVMHPVIAUKERS-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- RCYIBFNZRWQGNB-UHFFFAOYSA-N 2,6-dimethylheptan-1-ol Chemical compound CC(C)CCCC(C)CO RCYIBFNZRWQGNB-UHFFFAOYSA-N 0.000 description 1
- ACUZDYFTRHEKOS-SNVBAGLBSA-N 2-Decanol Natural products CCCCCCCC[C@@H](C)O ACUZDYFTRHEKOS-SNVBAGLBSA-N 0.000 description 1
- PJOLMBOMBNGLPQ-UHFFFAOYSA-N 4-hexoxy-4-oxobutanoic acid Chemical compound CCCCCCOC(=O)CCC(O)=O PJOLMBOMBNGLPQ-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- ACUZDYFTRHEKOS-UHFFFAOYSA-N decan-2-ol Chemical compound CCCCCCCCC(C)O ACUZDYFTRHEKOS-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 150000002311 glutaric acids Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- SEUYDDRXLZSABP-UHFFFAOYSA-N pentadecyl hexanoate Chemical compound CCCCCCCCCCCCCCCOC(=O)CCCCC SEUYDDRXLZSABP-UHFFFAOYSA-N 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23594562A | 1962-11-07 | 1962-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO119081B true NO119081B (en:Method) | 1970-03-23 |
Family
ID=22887494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO15067263A NO119081B (en:Method) | 1962-11-07 | 1963-11-02 |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE639662A (en:Method) |
| CH (1) | CH429691A (en:Method) |
| DE (1) | DE1468291A1 (en:Method) |
| GB (1) | GB982751A (en:Method) |
| LU (1) | LU44755A1 (en:Method) |
| NL (1) | NL300228A (en:Method) |
| NO (1) | NO119081B (en:Method) |
| SE (1) | SE312333B (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112441915A (zh) * | 2019-09-04 | 2021-03-05 | 中国石油化工股份有限公司 | 己二酸结晶精制工艺中结晶母液的处理方法 |
-
0
- NL NL300228D patent/NL300228A/xx unknown
- BE BE639662D patent/BE639662A/xx unknown
-
1963
- 1963-10-29 GB GB4270363A patent/GB982751A/en not_active Expired
- 1963-11-02 NO NO15067263A patent/NO119081B/no unknown
- 1963-11-05 DE DE19631468291 patent/DE1468291A1/de active Pending
- 1963-11-05 LU LU44755D patent/LU44755A1/xx unknown
- 1963-11-06 CH CH1362963A patent/CH429691A/fr unknown
- 1963-11-06 SE SE1223263A patent/SE312333B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE312333B (en:Method) | 1969-07-14 |
| CH429691A (fr) | 1967-02-15 |
| BE639662A (en:Method) | |
| DE1468291A1 (de) | 1969-05-29 |
| LU44755A1 (en:Method) | 1964-05-05 |
| NL300228A (en:Method) | |
| GB982751A (en) | 1965-02-10 |
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