DE2108487A1 - Functional, styrofoam tnaryl phosphate liquid - Google Patents

Description

February 18, 1971 ■ Pg / Ii.

Stauffer Chemical Company, Dobbs Perry, N.Y, 10522 / USA

"Functional j styrenated triaryl phosphate

liquid"

The invention relates to a method according to which in a closed hydraulic system that is an effective kenge of a styrenated phenyl (isopropylphenyl) phosphate, pressure is transmitted.

Functional fluids which are suitable for use in i hydraulic systems that require a combination of properties that are often in the z. The funds currently available will not be achieved. One of the properties required for safe and satisfactory work at low temperatures is a low pour point. Other important properties that hydraulic fluids should have are high viscosity and a flat viscosity-temperature curve, i.e. a high viscosity index that allows the fluid to move over a wide temperature range.

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area to remain functional. One of the main features which are required for hydraulic fluids, which are either used in industry, mining or Used in the military field, the lowest possible flammability. Other desirable qualities such products have a relatively high boiling point and low susceptibility to oxidation. Furthermore, they shouldn't have a corrosive effect.

It is known that the viscosity index of hydraulic fluids decreases with increasing proportions of cyclic fluids Compounds contain, (cf. Murphy and coworkers, Industrial and Engineering Chemistry, Volume 42, page 2415; Bried et al, Industrial and Engineering Chemistry, Volume 39, page 484 and the references contained therein). Products that contain a high proportion of aromatics are therefore usually less than hydraulic fluids suitable. It is also known that benzyl compounds are mostly too sensitive to attack by are free radicals. Oxygen and other reactive substances attack a benzyl residue. Styrenated compounds should therefore, as expected, have low oxidation stability and should therefore not be used as hydraulic fluids be suitable.

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It has now been found that new styrenated phenyl bis (isopropylphenyl) phosphates are suitable as hydraulic fluids and surprisingly have the properties mentioned above which are necessary for the advantageous use of these products. More specifically, these phosphates have a high viscosity ranging from about 800 to about 1200 "Saybolt Universal Seconds" (SUS) Ό, -. ~ 38 ⁰ C. Further, they have in this viscosity range as compared to commercially available liquids a relatively high viscosity index. Furthermore, these phosphates show

(pour point)

points / below -17 »8 ⁰ C and high self-ignition points in the range from 482 to 593 C.

The phosphates used in the process according to the invention are new styrenated phenyl bis (isopropylphenyl) phosphates of the following formula:

Il

CH ₃ CHCH ₃

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in which η is a number above 0 and below 1 and m are a number from 1 to 2 inclusive.

The products according to the invention can be prepared in a two-step process be prepared: (a) Phosphorus trichloride is made with styrenated phenol or a styrenated phenol mixture reacted in the presence of a Lewis acid catalyst and (b) the reaction product with isopropylated Phenol or an isopropylated phenol mixture reacted. The procedure is as follows:

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/ CH

OH + POCl ₃

Lewis acid catalyst

CH3CHCH3

I + (3-n)

catalyst

OH

Il

CH 3 CH CH 3

3-n

+ ("3-n) HCl

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where η is a number above 0 and below 1 and ra are a number from 1 to 2 inclusive.

Steps (a) and (b) can be carried out sequentially or simultaneously, but the reaction will preferred in two stages because it allows better control of the η values for the hydraulic fluids according to the invention are essential.

The inventive reaction is in the presence of a Lewis acid catalyst running. The expression “Lewis acid catalyst” includes such inorganic compounds understood, which are strong electron pair acceptors. Such compounds are well known. For example, iron, aluminum, zinc and magnesium chloride, molybdenum pentachloride and tin tetrachloride are suitable and boron trifluoride. The Lewis acid catalyst is the reaction mixture in amounts of about 0.1 to 5.0 wt .- ί and preferably added in the amount of 0.05 to 2 wt.

The for the production of the hydraulic fluids according to the invention The styrenated phenols used are commercially available mixtures of a relatively large amount of styrenated Phenol and minor amounts of phenol and distyrenated phenol. You can also implement styrene with dirch

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-T-

Phenol at elevated temperatures in the presence of catalysts can be synthesized. The isopropylated phenols are also commercially available, usually as Mixtures consisting of a large amount of o-, m- and p-isopropylphenols exist and still smaller amounts of 2,6-diisopropylphenol, 2,4-diisopropylphenol, triisopropylphenol and phenol.

The ratio of the isopropylphenyl building blocks to the styrenic |

based phenyl building blocks must be kept within certain limits so that the hydraulic fluids the above obtain desired properties. The ratio should be greater than 2: 1, i.e. η less than 1, so that liquids whose viscosities are in the desired range from 900 to about 1200 S.U.S. lie. Therefore should normally less than 1 mole of styrenated phenol or a styrenated phenol mixture per mole of phosphorus oxyhalide used in stage (a) and at least 2 moles of isopropylphenol or an isopropylphenol mixture in stage (b) will.

The reaction temperature should be maintained in the range of 20 to about 300 ⁰ C and preferably from 100 to about 200 ⁰ C.

The response time is usually in the range of 4 to 20 hours. Shorter reaction times are obtained when working at higher temperatures.

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The styrenated phenyl-bis-cisopropylpheriyl-phosphate esters are characterized by having desirable, unusually high viscosities and viscosity indices. this is quite surprising as they contain a high proportion of cyclic structures in the molecule, which is normally how mentioned above, lower viscosity indices can be expected. I-an should therefore assume that functional triaryl phosphate fluids on the basis of tricresyl and trixylyl phosphates have higher viscosity indices than styrenated phenyl bis (isopropylphenyl) phosphates of the present invention, surprisingly, however the compounds according to the invention have higher viscosity indices than those of the triaryl phosphates.

The styrenated triaryl phosphates according to the invention can either alone or in a mixture with an anti-corrosion agent ^ Defoamers and various additives that are described in the literature can be used. For economic Reasons can be the functional fluids of the invention with inexpensive petroleum oils and / or polychloroaromatic Compounds, especially polychlorobenzenes and polychlorobiphenylene, are mixed.

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Find the products of the process of the invention e.g. in closed hydraulic systems such as compressors, hydraulic elevators, hydraulic conveyor baskets, brake systems, Basic oxygen furnace, injection molding machines, leveling devices or servo controls Use. The use takes place in such a way that the on the phosphates at a certain point of the Hydraulic system pressure exerted by the phosphates at j

every other point of the hydraulic system is transmitted.

example 1

A 2 liter Pyrex 3-neck flask was fitted with a thermometer, reflux condenser, dropping funnel and magnetic stirrer. The reflux condenser was through a T-tube with a nitrogen line and an aqueous hydrochloric acid reservoir connected; 163.4 g of phosphorus oxychloride and 195 £ Commercial styrenated phenol of the following "

Composition entered: 21.4 % phenol, 57.8% monostyrenated phenol, 15.3 % diatyrenated phenol and 5.3 % trlstyrenated phenol. While stirring at a moderate speed, nitrogen was blown over the reaction silencer. Then 2: _; Kagnesiumciilorld quickly entered the reactor. The temperature

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- ίο -

was slowly increased from 25 to 100 ^° C. over a period of about 1 hour and then maintained for about 4 hours.

During this time 1 KoI hydrochloric acid collected in the receiver. Subsequently, within 40 Iiin. at a temperature of 108 to 117 ^° C., 268 g of commercially available isopropylated phenol were introduced dropwise into the reactor.

The phenol mixture had the following composition:

85 ö _3% 0-, m- and p-isomers of isopropylphenol, 3.8% 2,6-diisopropylphenol, 9.6% 2,4-Diisopropylpher.ol and triisopropyl $ 1. The temperature was gradually increased to IbO ⁰ C and maintained until about 1.9 LoI hydrochloric acid had been collected in the receiver. Then the reaction mixture was placed in a 1 1 still and low-boiling substances at I87 ⁰ C within 1 hr.

distilled off at 0.50 mm Hg. The crude product was drip-

- τ

as registered in a container cm x ^{3 0} C contained the 500 a well-stirred 1 $ strength caustic solution of oO and stirred. 1 hr. The phases were then separated using a separating funnel. The Ätzalkaliwäsche was repeated three times at 60 ⁰ C and then the reaction product was washed with a 1 £ strength phosphoric acid solution. The product was then washed with water and distilled to dryness with 1 l of benzene. The benzene was removed by distillation at 42 ^° C. and 200 mm Hg. The cloudy product was filtered through a bed of Fuller's earth ^{at about 0 ° -70 ° C.}

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Then the product is analyzed. The results are the Table I can be found.

Example 2

The procedure of Example 1 was repeated. The results can also be found in Table I below.

• Table I

Example I Example II

S.ü.S. (Saybolt Universal Second)

37.8 ⁰ C

UMR Γΐοΐ Styrophenyl pro
Moles of phosphate

Si'uresahl mg KOH / 3

1.029

1.087

3 < 1.0 <1 _} o 0.14 0 , 56 1.5571 1 , 5580 1.11 1 , 11 example

The procedure described in Example 1 was repeated. According to the NMR analysis, the product contained about 0.7 styrophenyl groups per molecule. The product was compared with the hydraulic fluid available under the trade name "Fyrquel 1000" from the Stauffer Chemical Company of New York and having the same viscosity range. The results of the comparison are shown in Table II.

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Styrophenyl bis (isopropylphenyl) phosphate

"Pyrquel 1000"

Viscosity at 37.8 ⁰ C (SUS)

Viscosity at 98.9 ⁰ G viscosity index pour point ⁰ C

1009.9

61.23

-47
-20.6

1000

51.6 -216 -1.1

From Table II it can be seen that the inventive Products exhibit superior viscosity indices and pour points when used with commercially available hydraulic fluids of the same Viscosity range can be compared.

The liquids according to the invention are also favorable Properties when used with a Vickers 104 capsule pump be tested. When tested, these liquids give viscosity, Coloring and neutralization characteristics equal to or superior to commercially available hydraulic fluids are.

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Claims (2)

Claims 1. Method of transferring pressure in a hydraulic System, characterized in that an effective amount of a phosphate ester in the hydraulic system the following formula: CH ₃ CHCH ₃ in eier η a number greater than 0 and less than 1 and m is a number from 1 to 2 inclusive, further exerts pressure on the phosphate ester at some point in the system, and so that it transfers the pressure through the system and the phosphate ester. 2. The method according to claim 1, characterized in that η is a number from 0.5 to 0.9 inclusive. 109837M477 BATH ORIGINAL 3 · / Puncture fluid muddy, which is an effective Amount of a phosphate ester of the following formula CH ₃ Ί T O- 9 W. in which η is a number greater than 0 and less than 1 and m is a number from 1 to 2 inclusive. 109837/1477 BATH ORIGINAL