CN103145618A - Method for cogeneration of caprolactam and ammonium sulfate - Google Patents
Method for cogeneration of caprolactam and ammonium sulfate Download PDFInfo
- Publication number
- CN103145618A CN103145618A CN2013100840781A CN201310084078A CN103145618A CN 103145618 A CN103145618 A CN 103145618A CN 2013100840781 A CN2013100840781 A CN 2013100840781A CN 201310084078 A CN201310084078 A CN 201310084078A CN 103145618 A CN103145618 A CN 103145618A
- Authority
- CN
- China
- Prior art keywords
- ammonium sulfate
- caprolactam
- ammonia
- sulfonate
- hexanolactam
- 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.)
- Granted
Links
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims abstract description 154
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 title claims abstract description 91
- 229910052921 ammonium sulfate Inorganic materials 0.000 title claims abstract description 91
- 235000011130 ammonium sulphate Nutrition 0.000 title claims abstract description 91
- 238000000034 method Methods 0.000 title claims abstract description 41
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 100
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 50
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 43
- 239000007788 liquid Substances 0.000 claims description 19
- 238000006386 neutralization reaction Methods 0.000 claims description 19
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims description 18
- 238000006237 Beckmann rearrangement reaction Methods 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 30
- 239000012452 mother liquor Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 32
- 239000013078 crystal Substances 0.000 description 27
- 239000000047 product Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 208000005156 Dehydration Diseases 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000007670 refining Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 210000003608 fece Anatomy 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 239000010871 livestock manure Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- RSPWPAYFBOWLKA-UHFFFAOYSA-N cyclohexane;formic acid Chemical compound OC=O.C1CCCCC1 RSPWPAYFBOWLKA-UHFFFAOYSA-N 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000004134 energy conservation Methods 0.000 description 2
- VGYYSIDKAKXZEE-UHFFFAOYSA-L hydroxylammonium sulfate Chemical compound O[NH3+].O[NH3+].[O-]S([O-])(=O)=O VGYYSIDKAKXZEE-UHFFFAOYSA-L 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000006146 oximation reaction Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229910000978 Pb alloy Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- HEPLMSKRHVKCAQ-UHFFFAOYSA-N lead nickel Chemical compound [Ni].[Pb] HEPLMSKRHVKCAQ-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000000618 nitrogen fertilizer Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN201310084078.1A CN103145618B (en) | 2013-03-15 | 2013-03-15 | Method for cogeneration of caprolactam and ammonium sulfate |
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CN201310084078.1A CN103145618B (en) | 2013-03-15 | 2013-03-15 | Method for cogeneration of caprolactam and ammonium sulfate |
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CN103145618A true CN103145618A (en) | 2013-06-12 |
CN103145618B CN103145618B (en) | 2014-06-18 |
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CN201310084078.1A Active CN103145618B (en) | 2013-03-15 | 2013-03-15 | Method for cogeneration of caprolactam and ammonium sulfate |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110240495A (en) * | 2019-07-16 | 2019-09-17 | 湖北金湘宁化工科技有限公司 | A kind of method of caprolactam and phosphoric acid coproducing ammonium |
CN111960894A (en) * | 2020-08-26 | 2020-11-20 | 山西绿丰肥业有限公司 | Water-soluble fertilizer capable of quickly improving nutrients of crops and preparation method thereof |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108341763B (en) * | 2018-04-24 | 2020-12-01 | 河北美邦工程科技股份有限公司 | Caprolactam crystallization and purification method |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3859278A (en) * | 1972-12-11 | 1975-01-07 | Stamicarbon | Process for separating lactams |
US3907781A (en) * | 1973-06-26 | 1975-09-23 | Stamicarbon | Process for recovery of {68 -caprolactam from a reaction mixture of {68 -caprolactam and sulphuric acid |
US3937789A (en) * | 1965-01-21 | 1976-02-10 | Snia Viscosa Societa' Nazionale Industria Applicazioni Viscosa S.P.A. | Process for the neutralization of acid solutions of caprolactam |
US4138472A (en) * | 1976-11-10 | 1979-02-06 | Basf Aktiengesellschaft | Process for obtaining coarsely crystalline pure ammonium sulfate |
WO2000066561A1 (en) * | 1999-04-29 | 2000-11-09 | Dsm N.V. | Process for the preparation of caprolactam |
JP2010163319A (en) * | 2009-01-16 | 2010-07-29 | Ube Ind Ltd | Method for producing ammonium sulfate |
-
2013
- 2013-03-15 CN CN201310084078.1A patent/CN103145618B/en active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3937789A (en) * | 1965-01-21 | 1976-02-10 | Snia Viscosa Societa' Nazionale Industria Applicazioni Viscosa S.P.A. | Process for the neutralization of acid solutions of caprolactam |
US3859278A (en) * | 1972-12-11 | 1975-01-07 | Stamicarbon | Process for separating lactams |
US3907781A (en) * | 1973-06-26 | 1975-09-23 | Stamicarbon | Process for recovery of {68 -caprolactam from a reaction mixture of {68 -caprolactam and sulphuric acid |
US4138472A (en) * | 1976-11-10 | 1979-02-06 | Basf Aktiengesellschaft | Process for obtaining coarsely crystalline pure ammonium sulfate |
WO2000066561A1 (en) * | 1999-04-29 | 2000-11-09 | Dsm N.V. | Process for the preparation of caprolactam |
JP2010163319A (en) * | 2009-01-16 | 2010-07-29 | Ube Ind Ltd | Method for producing ammonium sulfate |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110240495A (en) * | 2019-07-16 | 2019-09-17 | 湖北金湘宁化工科技有限公司 | A kind of method of caprolactam and phosphoric acid coproducing ammonium |
CN111960894A (en) * | 2020-08-26 | 2020-11-20 | 山西绿丰肥业有限公司 | Water-soluble fertilizer capable of quickly improving nutrients of crops and preparation method thereof |
Also Published As
Publication number | Publication date |
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CN103145618B (en) | 2014-06-18 |
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TR01 | Transfer of patent right |
Effective date of registration: 20160921 Address after: 310000, room 532, 325 Shiqiao Road, Xiacheng District, Zhejiang, Hangzhou Patentee after: Hangzhou Xiangyun Chemical Co.,Ltd. Address before: 274500 west section of 38 Road, Dongming County, Shandong, Heze Patentee before: DONGMING TIANJUN CHEMICAL Co.,Ltd. |
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EE01 | Entry into force of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20130612 Assignee: Zhongshi Chemical Construction Co.,Ltd. Suzhong branch Assignor: Hangzhou Xiangyun Chemical Co.,Ltd. Contract record no.: X2021320000085 Denomination of invention: A method for CO production of caprolactam and ammonium sulfate Granted publication date: 20140618 License type: Common License Record date: 20210930 |
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EE01 | Entry into force of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20130612 Assignee: HUBEI SANNING CHEMICAL Co.,Ltd. Assignor: Hangzhou Xiangyun Chemical Co.,Ltd. Contract record no.: X2021420000048 Denomination of invention: A method for CO production of caprolactam and ammonium sulfate Granted publication date: 20140618 License type: Common License Record date: 20211230 |
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TR01 | Transfer of patent right | ||
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Effective date of registration: 20220929 Address after: 310012 Room 813, Building 5, No. 1, Xiyuan 8th Road, Xihu District, Hangzhou, Zhejiang Patentee after: Hangzhou Yihong Chemical Technology Co.,Ltd. Address before: Room 325, No. 532, Shiqiao Road, Xiacheng District, Hangzhou, Zhejiang 310000 Patentee before: Hangzhou Xiangyun Chemical Co.,Ltd. |
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EE01 | Entry into force of recordation of patent licensing contract | ||
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Application publication date: 20130612 Assignee: Hubei Jinxiangning Chemical Technology Co.,Ltd. Assignor: Hangzhou Yihong Chemical Technology Co.,Ltd. Contract record no.: X2022420000124 Denomination of invention: A method for co production of caprolactam and ammonium sulfate Granted publication date: 20140618 License type: Common License Record date: 20221109 |
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EC01 | Cancellation of recordation of patent licensing contract | ||
EC01 | Cancellation of recordation of patent licensing contract |
Assignee: Hubei Jinxiangning Chemical Technology Co.,Ltd. Assignor: Hangzhou Yihong Chemical Technology Co.,Ltd. Contract record no.: X2022420000124 Date of cancellation: 20240529 |
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EE01 | Entry into force of recordation of patent licensing contract | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20130612 Assignee: Hubei Jinxiangning Chemical Technology Co.,Ltd. Assignor: Hangzhou Yihong Chemical Technology Co.,Ltd. Contract record no.: X2024330000093 Denomination of invention: A method for co production of caprolactam and ammonium sulfate Granted publication date: 20140618 License type: Common License Record date: 20240530 |