CN1634815A - Process for preparing multi-alkyl cyclopentane - Google Patents
Process for preparing multi-alkyl cyclopentane Download PDFInfo
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- CN1634815A CN1634815A CN 200310122460 CN200310122460A CN1634815A CN 1634815 A CN1634815 A CN 1634815A CN 200310122460 CN200310122460 CN 200310122460 CN 200310122460 A CN200310122460 A CN 200310122460A CN 1634815 A CN1634815 A CN 1634815A
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- CN
- China
- Prior art keywords
- cyclopentadiene
- alkyl
- described preparation
- alkane
- many
- 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
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title claims abstract description 14
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims abstract description 33
- -1 C12 alkane Chemical class 0.000 claims abstract description 26
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 7
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 7
- 239000003085 diluting agent Substances 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 17
- 238000010790 dilution Methods 0.000 claims description 13
- 239000012895 dilution Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 5
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 10
- 208000012839 conversion disease Diseases 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- 238000001816 cooling Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- 238000013019 agitation Methods 0.000 description 7
- 238000005303 weighing Methods 0.000 description 7
- SEETZWBREGLMAN-UHFFFAOYSA-N 1-decylcyclopenta-1,3-diene Chemical compound CCCCCCCCCCC1=CC=CC1 SEETZWBREGLMAN-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- TZARQKAQCWAVDR-UHFFFAOYSA-N 1-(11-methyldodecyl)cyclopenta-1,3-diene Chemical compound C(CCCCCCCCCC(C)C)C1=CC=CC1 TZARQKAQCWAVDR-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The present invention relates to a method for preparing multi-alkyl cyclopentane by hydrogenation of multi-alkyl cyclopentadiene. The multi-alkyl cyclopentadiene is diluted by c6 to C12 alkane and mixed with amorphous state nickel catalyst in a high-pressure reaction kettle, then it is hydrogenated under a hydrogen pressure of 3-20 MPa and a temperature of 50-200 DEG C, wherein the usage amount of the amorphous state nickel is 0.1 to 10% of multi-alkyl cyclopentadiene alkane diluent by weight. The method adopts a cheap and high efficient catalyst, as a result, high reaction conversion rate which is near to the prior art is obtained, while the reaction cost is reduced.
Description
Technical field
The present invention relates to by the method for many alkyl cyclopentadiene by the hydrogenation preparing multi-alkyl cyclopentane.
Background technology
Multi-alkyl cyclopentane is a kind of approaching monomolecular compound, has very low volatility and saturated vapor pressure, and good high temperature performance and lubricity can directly be used as high-performance special lubricant base oil, blend component or lubricant additive.
By the method for many alkyl cyclopentadiene by the hydrogenation preparing multi-alkyl cyclopentane is known.
US 4,929, and 782 disclose a kind of preparation method, this method is that to adopt supported palladium be catalyzer, adopts alkane solvent or without solvent, hydrogen pressure is at 3-20MPa, temperature of reaction is selected in 75-200 ℃ of scope, can obtain multi-alkyl cyclopentane by many alkyl cyclopentadiene hydrogenation.
Above-mentioned preparation method can obtain very high reaction conversion ratio, but loaded palladium catalyst costs an arm and a leg, and causes reaction cost very high.
Summary of the invention
The purpose of this invention is to provide a kind of by the method for many alkyl cyclopentadiene by the hydrogenation preparing multi-alkyl cyclopentane, this method can reduce reaction cost by adopting a kind of inexpensive and catalyzer efficiently when obtaining the high reaction conversion ratio close with prior art.
The preparation method of multi-alkyl cyclopentane provided by the invention comprises:
With many alkyl cyclopentadiene with the dilution of C6-C12 alkane after, and with the amorphous nickel catalyst mix after, put into autoclave, feed hydrogen, at hydrogen pressure is 3-20MPa, and temperature is under 50 ℃-200 ℃ the condition hydrogenation reaction to take place, and collects the product multi-alkyl cyclopentane.
Said many alkyl cyclopentadiene are the mixtures that contains the cyclopentadiene of 2-4 alkyl, wherein the weight content of dialkyl cyclic pentadiene, trialkyl cyclopentadiene and tetraalkyl cyclopentadiene is about 10-15%, 70-90% and 0-20%, alkyl wherein is positive structure or the isomery alkyl of C5-C24, as positive decyl, isotridecyl, eicosyl etc.
Many alkyl cyclopentadiene can be bought from market or make by oneself according to disclosed document, for example, can prepare in accordance with the following methods: heat adding in the reaction flask that agitator, separating funnel, prolong, water trap, thermometer are housed after the positive structure of C5-C24 or isomery alcohol, solid potassium hydroxide and the dicyclopentadiene mixing.When no longer including water generates in the water trap, stopped reaction.After reaction product washing, drying, filtration, obtain many alkyl cyclopentadiene.
Said alkane as thinner is C6-C12 normal paraffin, isoparaffin or naphthenic hydrocarbon, preferred hexanaphthene, normal heptane and naphthane.The Dilution ratio of alkane and many alkyl cyclopentadiene (extent of dilution) is 1-50: 100 (quality), preferably 5-30: 100.
Wherein the consumption of amorphous nickel is the 0.1-10% of many alkyl cyclopentadiene alkane diluent weight, preferably 0.8-3%.
Reaction conditions is that hydrogen pressure is 3-20MPa, is preferably 3-8MPa, and temperature of reaction is 50 ℃-200 ℃, and the best is 120 ℃-190 ℃.Reaction times is 5-30 hour, preferably 15-20 hour.After reaction is finished,, take out material, filter, remove thinner, obtain the sintetics multi-alkyl cyclopentane the reactant cooling.
The invention is characterized in and selected a kind of inexpensive and catalyzer-amorphous nickel efficiently, compare with the preparation method of noble metal catalysts such as existing working load palladium, advantage is to greatly reduce reaction cost when obtaining the high reaction conversion ratio close with the preparation method of noble metal catalysts such as working load palladium; And compare with the preparation method of existing use Raney's nickel catalyst, reaction conversion ratio improves.
Embodiment
Embodiment 1
It is 10% solution that will be many (dialkyl group 10.2%, trialkyl 70.6%, tetraalkyl 19.2%) positive decyl cyclopentadiene (self-control) and normal heptane is made into extent of dilution.Put into autoclave after this solution of weighing 200g and the 3.6g amorphous nickel catalyst mix, feed hydrogen and reach 5MPa, under good agitation condition, be heated to 155 ℃, react stopped reaction after 20 hours until hydrogen pressure.Material is taken out in question response thing cooling back, removes after filtering and desolvates, and obtains the positive decyl pentamethylene of sintetics many (containing two, three and four), and reaction conversion ratio reaches more than 95%.
Embodiment 2
It is 15% solution that will be many (dialkyl group 10.2%, trialkyl 70.6%, tetraalkyl 19.2%) positive decyl cyclopentadiene (self-control) and naphthane is made into extent of dilution.Put into autoclave after this solution of weighing 200g and the 3.6g amorphous nickel catalyst mix, feed hydrogen and reach 5MPa, under good agitation condition, be heated to 155 ℃, react stopped reaction after 20 hours until hydrogen pressure.Material is taken out in question response thing cooling back, removes after filtering and desolvates, and obtains the positive decyl pentamethylene of sintetics many (containing two, three and four), and reaction conversion ratio reaches more than 95%.
Embodiment 3
It is 10% solution that (dialkyl group 15.8%, trialkyl 84.2%) the isotridecyl cyclopentadiene (self-control) of will be many and normal heptane are made into extent of dilution.Put into autoclave after this solution of weighing 200g and the 3.6g amorphous nickel catalyst mix, feed hydrogen and reach 5MPa, under good agitation condition, be heated to 165 ℃, react stopped reaction after 20 hours until hydrogen pressure.Material is taken out in question response thing cooling back, removes after filtering and desolvates, and obtains sintetics many (containing two, three) isotridecyl pentamethylene, and reaction conversion ratio reaches more than 95%.
Embodiment 4
It is 20% solution that (dialkyl group 15.8%, trialkyl 84.2%) the isotridecyl cyclopentadiene (self-control) of will be many and naphthane are made into extent of dilution.Put into autoclave after this solution of weighing 200g and the 5g amorphous nickel catalyst mix, feed hydrogen and reach 6MPa, under good agitation condition, be heated to 165 ℃, react stopped reaction after 20 hours until hydrogen pressure.Material is taken out in question response thing cooling back, removes after filtering and desolvates, and obtains sintetics many (containing two, three) isotridecyl pentamethylene, and reaction conversion ratio reaches more than 95%.
Embodiment 5
It is 10% solution that (dialkyl group 11.6%, trialkyl 88.4%) the eicosyl cyclopentadiene (self-control) of will be many and naphthane are made into extent of dilution.Put into autoclave after this solution of weighing 200g and the 3.6g amorphous nickel catalyst mix, feed hydrogen and reach 5.5MPa, under good agitation condition, be heated to 185 ℃, react stopped reaction after 20 hours until hydrogen pressure.Material is taken out in question response thing cooling back, removes after filtering and desolvates, and obtains sintetics many (containing two, three) eicosyl pentamethylene, and reaction conversion ratio reaches more than 95%.
Comparative example 1
It is 10% solution that will be many (dialkyl group 10.2%, trialkyl 70.6%, tetraalkyl 19.2%) positive decyl cyclopentadiene and normal heptane is made into extent of dilution.This solution of weighing 200g with put into autoclave after 3g loaded palladium catalyst (wherein palladium content is 0.75%) mixes, feed hydrogen and reach 5MPa until hydrogen pressure, under good agitation condition, be heated to 155 ℃, react stopped reaction after 20 hours.Material is taken out in question response thing cooling back, removes after filtering and desolvates, and obtains the positive decyl pentamethylene of sintetics many (containing two, three and four).
Comparative example 2
It is 10% solution that will be many (dialkyl group 10.2%, trialkyl 70.6%, tetraalkyl 19.2%) positive decyl cyclopentadiene and normal heptane is made into extent of dilution.This solution of weighing 200g with put into autoclave after the 3.6g Raney's nickel catalyst mixes, feed hydrogen and reach 5MPa until hydrogen pressure, heating is 155 ℃ under good agitation condition, reacts stopped reaction after 20 hours.Material is taken out in question response thing cooling back, removes after filtering and desolvates, and obtains the positive decyl pentamethylene of sintetics many (containing two, three and four).
Table 1 the present invention and the existing comparison of making the technology of catalyzer with supported palladium
Catalyst agent consumption product bromine covalent reaction thing transformation efficiency catalyzer price per ton
/ %/g (Br) (100g)
-1/ %/unit
Supported palladium is urged about 1.5 0.1 99.5 200 ten thousand
Change agent
About amorphous nickel 1.8 0.1 99.5 20 ten thousand
Catalyzer
The comparison of the technology of table 2 the present invention and usefulness Raney's nickel catalyst
Catalyst agent consumption product bromine covalent reaction thing transformation efficiency
/％ /g(Br)·(100g)
-1 /％
Amorphous nickel 1.8 0.1 99.5
Catalyzer
Raney's nickel 1.8 1.3 93.8
Catalyzer
Claims (10)
1. the preparation method of a multi-alkyl cyclopentane comprises:
With many alkyl cyclopentadiene with the dilution of C6-C12 alkane after, and with the amorphous nickel catalyst mix after, put into autoclave, feed hydrogen, at hydrogen pressure is 3-20MPa, and temperature is under 50 ℃-200 ℃ the condition hydrogenation reaction to take place, and collects the product multi-alkyl cyclopentane.
2. according to the described preparation method of claim 1, it is characterized in that said many alkyl cyclopentadiene are the mixtures that contain the cyclopentadiene of 2-4 alkyl, alkyl wherein is positive structure or the isomery alkyl of C5-C24.
3. according to the described preparation method of claim 2, it is characterized in that the content of dialkyl cyclic pentadiene, trialkyl cyclopentadiene and tetraalkyl cyclopentadiene is respectively 10-15%, 70-90% and 0-20% in said many alkyl cyclopentadiene.
4. according to the described preparation method of claim 1, it is characterized in that said alkane as thinner is hexanaphthene, normal heptane or naphthane.
5. according to the described preparation method of claim 1, it is characterized in that the Dilution ratio of alkane and many alkyl cyclopentadiene is 1-50: 100.
6. according to the described preparation method of claim 5, it is characterized in that the Dilution ratio of alkane and many alkyl cyclopentadiene is 5-30: 100.
7. according to the described preparation method of claim 1, it is characterized in that wherein the consumption of amorphous nickel is the 0.1-10% of many alkyl cyclopentadiene alkane diluent weight.
8. according to the described preparation method of claim 7, it is characterized in that wherein the consumption of amorphous nickel is the 0.8-3% of many alkyl cyclopentadiene alkane diluent weight.
9. according to the described preparation method of claim 1, it is characterized in that hydrogen pressure is 3-8MPa, temperature of reaction is 120 ℃-190 ℃.
10. according to the described preparation method of claim 1, it is characterized in that the reaction times is 5-30 hour.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200310122460 CN1247496C (en) | 2003-12-25 | 2003-12-25 | Process for preparing multi-alkyl cyclopentane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200310122460 CN1247496C (en) | 2003-12-25 | 2003-12-25 | Process for preparing multi-alkyl cyclopentane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1634815A true CN1634815A (en) | 2005-07-06 |
| CN1247496C CN1247496C (en) | 2006-03-29 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200310122460 Expired - Lifetime CN1247496C (en) | 2003-12-25 | 2003-12-25 | Process for preparing multi-alkyl cyclopentane |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1247496C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102976883A (en) * | 2012-11-26 | 2013-03-20 | 金骄特种新材料（集团）有限公司 | Preparation method of bio-based polyalkyl cyclopentane synthetic oil |
| CN107573205A (en) * | 2017-10-27 | 2018-01-12 | 濮阳市联众兴业化工有限公司 | One kind is without naphthalene nucleus pentane production method |
| CN109053351A (en) * | 2018-08-29 | 2018-12-21 | 河南省君恒实业集团生物科技有限公司 | A kind of production technology using cyclopentadiene synthetic lubricant fluid |
-
2003
- 2003-12-25 CN CN 200310122460 patent/CN1247496C/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102976883A (en) * | 2012-11-26 | 2013-03-20 | 金骄特种新材料（集团）有限公司 | Preparation method of bio-based polyalkyl cyclopentane synthetic oil |
| CN102976883B (en) * | 2012-11-26 | 2015-06-24 | 金骄特种新材料（集团）有限公司 | Preparation method of bio-based polyalkyl cyclopentane synthetic oil |
| CN107573205A (en) * | 2017-10-27 | 2018-01-12 | 濮阳市联众兴业化工有限公司 | One kind is without naphthalene nucleus pentane production method |
| CN109053351A (en) * | 2018-08-29 | 2018-12-21 | 河南省君恒实业集团生物科技有限公司 | A kind of production technology using cyclopentadiene synthetic lubricant fluid |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1247496C (en) | 2006-03-29 |
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