CN106672914A - Solvent system in production of hydrogen peroxide working liquid by anthraquinone method - Google Patents
Solvent system in production of hydrogen peroxide working liquid by anthraquinone method Download PDFInfo
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- CN106672914A CN106672914A CN201510761617.XA CN201510761617A CN106672914A CN 106672914 A CN106672914 A CN 106672914A CN 201510761617 A CN201510761617 A CN 201510761617A CN 106672914 A CN106672914 A CN 106672914A
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- anthraquinone
- hydrogen
- production
- hydrogen peroxide
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- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims abstract description 50
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 32
- 150000004056 anthraquinones Chemical class 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 22
- 239000002904 solvent Substances 0.000 title abstract description 17
- 239000007788 liquid Substances 0.000 title abstract description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 23
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims description 26
- 239000012224 working solution Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 230000001590 oxidative effect Effects 0.000 claims description 19
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 9
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 abstract description 8
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- -1 hydrogen anthraquinone Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000008207 working material Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- HXQPUEQDBSPXTE-UHFFFAOYSA-N Diisobutylcarbinol Chemical compound CC(C)CC(O)CC(C)C HXQPUEQDBSPXTE-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical group CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- VVDZWMOQABVVHC-UHFFFAOYSA-N (1-methylcyclohexyl) acetate Chemical compound CC(=O)OC1(C)CCCCC1 VVDZWMOQABVVHC-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000004966 inorganic peroxy acids Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- VSURRQZMKWVYIC-UHFFFAOYSA-N n-ethyl-n-phenylbenzamide Chemical class C=1C=CC=CC=1N(CC)C(=O)C1=CC=CC=C1 VSURRQZMKWVYIC-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a solvent system in production of hydrogen peroxide working liquid by an anthraquinone method. The solvent system comprises the following components in percentage by volume: 50 to 80 percent, preferably 70 to 75 percent, of heavy aromatics, and 20 to 50 percent, preferably 25 to 30 percent, of 2-phenethyl alcohol. Compared with the heavy aromatic and trioctyl phosphate solvent system, the double-component solvent system has the advantages of improving the solubility of the anthraquinone and improving hydrogenation efficiency; and compared with the three-component system, the double-component solvent system has the advantages of simplifying constitution and reducing production cost, and has wide application prospect in production of hydrogen peroxide.
Description
Technical field
The present invention relates to the dicyandiamide solution in a kind of hydrogen dioxide solution production by anthraquinone process working solution.
Background technology
Hydrogen peroxide is a kind of important chemical products, is widely used in fields such as papermaking, chemical industry, food, environmental protection.Many valuable chemical products, such as inorganic peroxy acid and its salt, epoxides, organic peroxide and significant chemical reaction intermediate product can be prepared from hydrogen peroxide.Hydrogen peroxide has the selectivity more much higher than other oxidants as a kind of weaker oxidant, in organic synthesis.Hydrogen peroxide is used as bleaching agent in textile industry and paper-making industry, it is used as oxidant in chemical industry synthesis, it is used as disinfectant and bactericide in food and medicine industry, can be used to process toxic wastewater in terms of environmental protection, wherein processes at most and it is most useful that sulfide, cyanide and phenolic compound.Hydrogen peroxide can also be used to process poisonous fume, such as SO2, NO and H2S etc..Also it is used for the organic pollution oxidative degradation in water body.Hydrogen peroxide final reacting product itself is water, does not produce secondary pollution, is a kind of excellent green industry raw material and disinfectant.In recent years, as hydrogen peroxide is in environmental protection and the exploitation of other side new opplication, the demand of hydrogen peroxide increasingly increases.
Hydrogen peroxide preparation method mainly has：With carbon monoxide production peroxide passivation etc. in electrolysis, air cathode method, anthraquinone, hydrogen-oxygen direct synthesis technique, methyl-benzyl alcohol oxidizing process, isopropanol oxidation method, fuel cell method and the aqueous solution.Wherein, it is anthraquinone due to the advantages of its technology is advanced, production scale big, high degree of automation, cost and energy consumption are low, the three wastes are easy to improvement, there is greater advantage with respect to other methods.
In hydrogen dioxide solution production by anthraquinone process technique, working solution is mainly made up of the solvent of working material and dissolving working material.The production capacity of the property of solvent not only direct determination device, and to the efficiency of hydrogenation, oxidation and extracting operation process, the degraded of effective anthraquinone has considerable influence.Therefore, for the selection of solvent, typically require that it has strong to working material solvability, chemical stability is good, and the solubility in water and hydrogen peroxide is little, and, viscosity is little, low toxin with water stratification substantially.Under normal conditions, solvent is typically all and is formed by two kinds of organic solvent mixed preparings, a kind of solvent mainly as anthraquinone, it is another kind of mainly as
The solvent of hydrogen anthraquinone.Anthraquinone solvent mainly uses C in domestic hydrogen peroxide unit9Heavy aromatics, wherein isomers containing trimethylbenzene, the first and second benzene, propyl benzene and indenes etc.；Using the esters of higher aliphatic, organic acid or inorganic acid more than hydrogen anthraquinone solvent, industrial applications has trioctyl phosphate, diisobutyl carbinol (DIBC), methyl cyclohexanol acetate etc..At present relatively common dicyandiamide solution is heavy aromatics and trioctyl phosphate.
In order to improve the solubility of anthraquinone, also there is the working solution using three dicyandiamide solutions.CN1552618A discloses the organic solvent system in a kind of hydrogen peroxide production process, and it adopts C9~C10Aromatic hydrocarbons, trioctyl phosphate and 2- methylcyclohexyls acetate be working solution system, improve anthraquinone solubility, improve hydrogenation efficiency.CN101798065A discloses a kind of Working solution prescription for process for prepairng hydrogen peroxide by anthraquinone, and wherein solvent is consisted of：Heavy aromatics 65%～80%, trioctyl phosphate 5%～25%, N- phenyl N- ethyl benzamides 4.5%～17.8%, the solubility of working material is big, working solution medium density, and live load is big, reduces anthraquinone degradation rate.Although the anthraquinone solubility that three compositions system is improved, improves hydrogenation efficiency, the addition of third component also makes mixed solvent composition more complicated, while increased the production cost of hydrogen peroxide.
The content of the invention
For the deficiencies in the prior art, the invention provides the dicyandiamide solution in a kind of hydrogen dioxide solution production by anthraquinone process working solution.The working solution adopts two component solvent systems, with heavy aromatics compared with trioctyl phosphate dicyandiamide solution, improves anthraquinone solubility, improves hydrogenation efficiency, compared with three compositions system, simplifies composition, reduces production cost.
Dicyandiamide solution in the hydrogen dioxide solution production by anthraquinone process working solution of the present invention, the percent by volume of each component is in dicyandiamide solution：Heavy aromatics 50%～80%, preferably 70%～75%, 2 phenylethyl alcohol 20%～50%, preferably 25%～30%.
In the dicyandiamide solution of the present invention, described heavy aromatics is the C commonly used in hydrogen dioxide solution production by anthraquinone process9-C10Heavy aromatic solvent, density is 0.860-0.885g/cm3。
Present invention simultaneously provides a kind of working solution prepared by above-mentioned dicyandiamide solution, working solution carrier is alkyl-anthraquinone commonly used in the art, work liquid making method is known for those skilled in the art, wherein solubility of the 2- EAQs in working solution is 120～170 g/l, and the hydrogen effect of working solution is 8～10 g/l.
Using above-mentioned working solution, in the presence of a catalyst, with hydrogen by the anthraquinone alkyl derivative hydro-reduction in working solution, hydrogen anthraquinone is generated, then hydrogen peroxide is obtained Jing after air oxidation in oxidation reactor, while hydrogen anthraquinone reduction is anthraquinone derivative.
Working solution of the present invention is applied to during hydrogen dioxide solution production by anthraquinone process, and hydrogenation process process conditions are：Hydrogenation temperature is 30～80 DEG C, and hydrogenation pressure is 0.2～0.5MPa, and air speed is 1～30h-1, hydrogen liquor ratio is 1：1～300：1.Oxidizing process process conditions are：Oxidizing temperature is 30～70 DEG C, and oxidative pressure is 0.05～0.5MPa.
Compared with prior art, the present invention has following features：2 phenylethyl alcohol, with heavy aromatics mixed dissolution anthraquinone alkyl derivative, improves solubility of the anthraquinone in working solution as solvent, can be imitated with larger raising hydrogen, so as to improve production capacity, reduces production cost.
Specific embodiment
Effect and the effect of the present invention are further illustrated with reference to embodiment, but is not limited to following examples.
The present invention is to carry out hydrogenation using 10mL fixed-bed micro-reactors, and gained sample is carried out into oxidation 1 hour 50 DEG C using air after hydrogenation, then is extracted four times with separatory funnel, the content of detection wherein hydrogen peroxide.Hydrogen peroxide content detection adopts permanganimetric method.Catalyst is using the conventional Pd/Al for preparing2O3Catalyst.Catalyst particle size 0.4mm-0.5mm, pore volume 0.6cm3/g-0.7cm3/ g, specific surface area 150m2/g-180m2/ g, Pd content is 0.25%-0.35%.
Embodiment 1
With heavy aromatics：2 phenylethyl alcohol=75：25（Volume ratio）For the liquid medium that works, 2- EAQs solubility is 160 g/l.Hydrogenation temperature is 50 DEG C, and hydrogenation pressure is 0.25MPa, and air speed is 5h-1, hydrogen liquor ratio is 12：1.Oxidizing temperature is 50 DEG C, and oxidative pressure is 0.20MPa.Hydrogen effect is 9.23 g/l
Embodiment 2
With heavy aromatics：2 phenylethyl alcohol=50：50（Volume ratio）For the liquid medium that works, 2- EAQs solubility is 145 g/l.Hydrogenation temperature is 55 DEG C, and hydrogenation pressure is 0.30MPa, and air speed is 8h-1, hydrogen liquor ratio is 10：1.Oxidizing temperature is 55 DEG C, and oxidative pressure is 0.20MPa.Hydrogen effect is 8.24 g/l.
Comparative example 1
With heavy aromatics：Trioctyl phosphate=75：25（Volume ratio）For the liquid medium that works, 2- EAQs solubility is 129 g/l.Hydrogenation temperature is 55 DEG C, and hydrogenation pressure is 0.25 MPa, and air speed is 5h-1, hydrogen liquor ratio is 12：1.Oxidizing temperature is 50 DEG C, and oxidative pressure is 0.20MPa.Hydrogen effect is 7.20 g/l.
Comparative example 2
With heavy aromatics：Trioctyl phosphate=50：50（Volume ratio）For the liquid medium that works, 2- EAQs solubility is 98 g/l.Hydrogenation temperature is 55 DEG C, and hydrogenation pressure is 0.25 MPa, and air speed is 10h-1, hydrogen liquor ratio is 15：1.Oxidizing temperature is 50 DEG C, and oxidative pressure is 0.15 MPa.Hydrogen effect is 5.10 g/l.
Comparative example 3
Working solution is prepared according to embodiment in CN1552618A 3,2- EAQs solubility is 154 g/l.Hydrogenation temperature is 55 DEG C, and hydrogenation pressure is 0.25 MPa, and air speed is 5h-1, hydrogen liquor ratio is 12：1.Oxidizing temperature is 50 DEG C, and oxidative pressure is 0.20 MPa.Hydrogen effect is 8.32 g/l.
Claims (7)
1. the dicyandiamide solution in a kind of hydrogen dioxide solution production by anthraquinone process working solution, it is characterised in that：The percent by volume of each component is in dicyandiamide solution：Heavy aromatics 50%～80%, 2 phenylethyl alcohol 20%～50%.
2. according to the dicyandiamide solution described in claim 1, it is characterised in that：The percent by volume of each component is in dicyandiamide solution：Heavy aromatics 70%～75%, 2 phenylethyl alcohol 25%～30%.
3. according to the dicyandiamide solution described in claim 1 or 2, it is characterised in that：Described heavy aromatics is the C commonly used in hydrogen dioxide solution production by anthraquinone process9-C10Heavy aromatic solvent, density is 0.860-0.885g/cm3。
4. the working solution that prepared by the dicyandiamide solution described in a kind of claim 1 or 2, it is characterised in that：It is characterized in that：Solubility of the 2- EAQs in working solution is 120～170 g/l.
5. according to the working solution described in claim 4, it is characterised in that：The hydrogen effect of working solution is 8～10 g/l.
6. application of the working solution described in claim 4 in hydrogen dioxide solution production by anthraquinone process, hydrogenation process process conditions are：Hydrogenation temperature is 30～80 DEG C, and hydrogenation pressure is 0.2～0.5MPa, and air speed is 1～30h-1, hydrogen liquor ratio is 1：1～300：1.
7. according to the application described in claim 6, it is characterised in that：Oxidizing process process conditions are：Oxidizing temperature is 30～70 DEG C, and oxidative pressure is 0.05～0.5MPa.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510761617.XA CN106672914A (en) | 2015-11-11 | 2015-11-11 | Solvent system in production of hydrogen peroxide working liquid by anthraquinone method |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510761617.XA CN106672914A (en) | 2015-11-11 | 2015-11-11 | Solvent system in production of hydrogen peroxide working liquid by anthraquinone method |
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| CN106672914A true CN106672914A (en) | 2017-05-17 |
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| CN201510761617.XA Pending CN106672914A (en) | 2015-11-11 | 2015-11-11 | Solvent system in production of hydrogen peroxide working liquid by anthraquinone method |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2975033A (en) * | 1956-11-24 | 1961-03-14 | Fmc Corp | Process for preparation of hydrogen peroxide |
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2015
- 2015-11-11 CN CN201510761617.XA patent/CN106672914A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2975033A (en) * | 1956-11-24 | 1961-03-14 | Fmc Corp | Process for preparation of hydrogen peroxide |
Non-Patent Citations (2)
| Title |
|---|
| 华南理工大学无机化学教研室编: "《无机化学（第三版）》", 30 June 1994, 高等教育出版社 * |
| 辽宁省石油化学工业厅编: "《辽宁化工产品大全》", 31 December 1994, 辽宁科学技术出版社 * |
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Application publication date: 20170517 |